47 Is the Dream. 48 Is the Plan. 49 Is the Cushion.

I've been thinking a lot about retirement lately.

Not because I hate my job. I actually like what I do. I enjoy solving problems, working with people, and figuring out how to make things better.

But I've spent a good portion of my adult life chasing the next thing. Another degree, another promotion, another opportunity, another move.

And now? I'm starting to wonder what happens when I stop chasing.

My retirement date has been February 4, 2030. My 48th birthday.

I've got the spreadsheets. I've got ProjectionLab. I've got a savings plan. I've even thought about how I'll access my money before traditional retirement age.

Pretty impressive planning, right?

Except there's one small problem.

I like odd numbers.

So I started thinking, maybe I should retire in 2031. I'd be 49. Another year of saving, another year of investment growth, and a little more breathing room.

That sounds reasonable.

But then I thought, why not 47? I do love the number 7!

February 4, 2029.

Wait. That's basically tomorrow.

LOL.

And that's how I arrived at my newest retirement strategy:

47 is the dream. 48 is the plan. 49 is the cushion.

The Money Part

I work in finance. I like numbers. I like spreadsheets. I really like watching my investment accounts grow.

I also apparently like spending money renovating a townhouse. That part wasn't exactly in the original financial plan. :(

But the renovations are nearly finished, and I'm ready to get back to saving.

My goal is to put away another $50,000 a year on top of my retirement contributions and what my employer contributes.

I'm not counting bonuses. I'm not banking on some magical investment return. I just want to save as much as I reasonably can over the next few years.

I've worked hard to get here, and I want to finish what I started.

But something funny has happened as I've gotten closer to financial independence.

I'm starting to realize that figuring out the money might actually be easier than figuring out what comes next.

Okay, So What Am I Going to Do All Day?

This is where things get interesting.

For years, I've had a schedule. Work, workouts, responsibilities, errands, repeat.

And while I love the idea of not having to work, I also know myself.

I'm not someone who wants to sit around doing nothing.

I want to work out without rushing. I want to walk Harvey, my infamous pitbull mix. I want to travel, explore Colorado, write, read, and maybe even become one of those people who casually goes to a coffee shop on a Tuesday afternoon.

I also want to try things I've never done before.

Maybe gymnastics. More hiking. Learning something completely unrelated to healthcare finance.

Or maybe I'll do some consulting. I like solving problems. I'm just not sure I need to do it 40-plus hours a week forever.

The funny thing is that I have all these ideas, but I don't have a clear picture of what retirement actually looks like.

And for someone who likes a plan, that's a little uncomfortable.

There's Another Part to This

I've also been thinking about who I'll share this next chapter with.

I've done a lot on my own.

I've moved across states, built a career, bought homes, renovated homes, and created a pretty good life for myself.

But I don't necessarily want to do everything alone forever.

I'd love to find someone who wants to go on adventures, take weekend trips, watch football, or just hang out on the couch.

Someone who feels like home.

And then there's Harvey.

He's been my sidekick through multiple states, different jobs, and plenty of life changes.

When I think about retirement, I sometimes wonder how old he'll be by then and what our lives will look like.

I don't particularly enjoy thinking about that.

He's here now, usually requiring a walk, food, or some other form of attention. And I'm grateful for that.

But it's another reminder that life doesn't stand still while I'm busy planning for the future.

I can project my investments through 2050.

I have absolutely no idea what my personal life will look like in three years.

Wouldn't it be nice if ProjectionLab had a companionship tab?

Am I Just Creating Another Goal?

This is the question I've been asking myself lately.

I've spent so much of my life working toward something.

And now I've created another finish line.

February 4, 2030.

But what happens if I reach that date and decide I want to keep working?

What happens if the market has a bad year?

What happens if I meet someone, want to move, or decide to do something completely different?

Am I going to feel like I failed because I didn't retire on the exact date I picked years earlier?

I hope not.

Because the entire point of financial independence is having options.

Not creating another obligation.

Maybe I retire at 47. Maybe it's 48. Maybe I stay until 49.

Maybe I end up doing something part-time because I enjoy it.

I don't know.

And I'm trying to become more comfortable saying that.

The Years Between Now and Then

Here's what I don't want to do.

I don't want to spend the next three years staring at my investment balances, waiting for my real life to begin.

I want to enjoy my house now that I've spent a small fortune fixing it up.

I want more adventures with Harvey.

I want to keep exploring Colorado, visit my friends in Ohio, make new friends, go on dates when I feel like it, and try things that make me a little nervous.

I want to keep saving aggressively, too.

Because I genuinely enjoy it.

But I don't want to wake up in 2030 and realize I spent the last few years so focused on retiring that I forgot to enjoy being 44, 45, 46, and 47.

That's not exactly the point of Retire Toward.

So What's the Plan?

For now, I'm sticking with my three-number strategy.

47 is the dream.

48 is the plan.

49 is the cushion.

And if I change my mind again next week, well, that wouldn't exactly be surprising.

The money will keep growing. I'll keep saving. I'll keep updating my spreadsheets.

But I'm also going to keep living.

Because I've realized something:

I don't want to spend my life preparing for a life I haven't started living yet.

And maybe that's what Retire Toward is really about.

Not just figuring out when I can stop working.

But figuring out what makes me excited to get up in the morning, whether I'm working or not.

Preferably with a cup of coffee, Harvey nearby, and someone who wants to come along for the ride.

Build the money. Build the life.

Don't just retire from something. Retire toward something.

The Road to 2030: Building a Life Beyond the Spreadsheet

Financial independence at 48, 44 Colorado adventures, and learning that there's more to life than a really good budget.

I have a confession.

I love budgets.

And spreadsheets.

Especially spreadsheets.

Give me a problem, a blank Excel workbook, and a cup of coffee, and I'll happily disappear for a few hours.

I like building systems. Finding efficiencies. Creating something sustainable. Taking a big, messy problem and turning it into something manageable.

It's what I do professionally.

Unfortunately, it's also what I do personally.

Financial independence? There's a spreadsheet.

Retirement? Several spreadsheets.

Moving to Colorado? You better believe there was a plan.

Having fun?

Well, naturally, I created a list of 44 adventures to complete before 2030.

Because apparently, I can't even enjoy myself without establishing performance metrics.

At least I'm consistent.

February 4, 2030. Mark Your Calendars.

That's my 48th birthday.

And, if all goes according to plan, the day I make full-time employment optional.

I say if all goes according to plan because, at this point in my life, I've learned that the universe finds that phrase absolutely hilarious.

I've changed jobs. Moved across the country. Bought a house. Started over.

More than once.

And somehow, despite all those changes, I've managed to build a career I'm proud of and a financial foundation that gives me choices.

Here's the thing.

I don't hate working.

I actually like my career. If we're calling it that.

I like solving problems. I like building teams and improving systems. I like being challenged.

What I don't particularly love is the idea that I have to keep working for another 15 or 20 years simply because that's what people are supposed to do.

Who decided 65 was the magic number, anyway?

And why am I supposed to wait until then to enjoy a Tuesday morning?

My best health is now. I want to experience it all while I can.

I want to wake up without an alarm. Drink my coffee without checking emails. Take Harvey, my 11-year-old pit mix, for a long walk without mentally calculating how many minutes I have before my next meeting.

I want more time with people I love, especially those who may not have decades left.

Because the older I get, the more I realize something.

Money can compound.

Time cannot.

And I don't want to spend all of mine working toward a life I keep postponing.

The First Million: A Milestone and a Moment of Reflection

In January 2026, I crossed $1 million in net worth.

One. Million. Dollars.

It was a milestone I'd spent years working toward.

Saving. Investing. Making decisions that weren't always particularly exciting in the moment.

No secret inheritance. No winning lottery ticket. No cryptocurrency miracle.

Just years of building a financial foundation.

And when I finally reached that milestone, I was proud.

But I was also surprisingly hesitant to share it.

Money is a funny thing.

Sometimes people celebrate your accomplishments. Sometimes they make jokes, minimize them, or turn them into a competition.

And I found myself wondering why something I'd worked so hard for felt so difficult to talk about.

I honestly can't even remember exactly who I told. Maybe an old colleague who had become a mentor and friend.

On my birthday, I put on my headphones and wrote about the journey.

The work. The decisions. The setbacks. The years of showing up and building something for myself.

I was proud of what I'd accomplished.

But I was also a little sad that I didn't feel I had many people I could comfortably share the news with.

And that experience reminded me of something.

Financial success doesn't automatically create a fulfilling life.

The money gave me options.

It gave me confidence.

It gave me the freedom to imagine a different future.

But it couldn't replace connection, relationships, or the simple joy of sharing a meaningful moment with someone.

I had spent years learning how to build financial security.

Now I wanted to be just as intentional about building a life.

The Next Goal: Financial Independence by 48

Of course, being the goal-oriented person I am, I still have another number in mind.

Because apparently, reaching one milestone simply means it's time to update the spreadsheet.

My goal is $2 million in net worth by February 4, 2030.

Ideally, that means approximately $1.7 million in financial assets, with the remainder in net home equity.

And before anyone gets too excited about the real estate portion, let's clarify something.

Home equity is the value of your house minus what you owe on the mortgage.

You don't get to count the house and conveniently forget the debt.

I know. Disappointing.

Also, a house may contribute to your net worth, but it doesn't exactly pay for groceries unless you're planning to sell the kitchen.

So the financial assets are the important part of the retirement equation.

Can I reach $2 million by 2030?

Maybe.

Could the stock market have a complete emotional breakdown in 2029?

Absolutely.

I can control my contributions, spending, and investment decisions.

I cannot control whether Wall Street wakes up in a bad mood.

That's why I'm focused on progress, not perfection.

The goal gives me direction.

The plan gives me a framework.

And the ability to pivot gives me some sanity.

Well, most days.

The Five-Year Bridge: Because Apparently You Can't Just Retire Whenever You Feel Like It

Now we're getting to the nerdy stuff.

Stay with me.

If I retire at 48, much of my retirement savings will still be sitting in accounts with rules about when and how I can withdraw the money.

Which seems a little rude, considering it's my money.

But okay, IRS. Let's play.

One strategy I'm exploring is a Roth conversion ladder.

Here's the simplified version.

During retirement, when my income may be lower, I can gradually convert money from traditional retirement accounts into a Roth IRA.

I'll generally owe income taxes on those conversions.

But if I plan carefully, I may be able to make those conversions at more favorable tax rates than during my highest-earning years.

The catch?

Converted taxable amounts generally have a five-tax-year waiting period before I can withdraw them without a conversion-related early-distribution penalty.

So I need accessible money to support myself while I establish the ladder.

Enter my five-year bridge.

Not a literal bridge.

Although I do live in Colorado, and I'm sure I could find one with spectacular mountain views.

I'm talking about enough accessible savings and investments to cover approximately five years of living expenses while I start converting retirement funds.

After that, eligible conversions could begin supporting future spending while I continue managing the ladder through the years before age 59½.

Sounds simple, right?

Well, except for taxes, healthcare, investment returns, inflation, withdrawal rules, and the small matter of actually knowing how much money I plan to spend.

Minor details.

This is why I have spreadsheets.

And why I probably need more coffee.

The $50,000 Question: Have I Become Too Good at Saving?

Here's where things get interesting.

I've been considering contributing $50,000 a year to my taxable brokerage account until retirement.

That's a significant amount of money.

And my first instinct is to figure out how to make it happen.

Because saving is what I do.

I save. I invest. I automate. I optimize.

I have spent years building habits that make financial progress feel almost automatic.

But recently I caught myself asking a question I wasn't expecting.

What if I don't actually need to save that much?

Excuse me?

Who said that?

Certainly not the finance lady with 14 tabs open in Excel.

But it's a legitimate question.

I already have a taxable investment portfolio. I already contribute to retirement accounts. I already have a financial foundation.

So instead of blindly choosing another savings target, I'm working backward.

How much do I actually need to live on?

How much should I budget for healthcare?

What will my taxes look like?

How much should remain invested?

How much should I hold in cash so I'm not forced to sell stocks during a market downturn?

One idea I'm exploring is having approximately $60,000 in cash or cash equivalents available when I retire, with additional taxable investments supporting the rest of my bridge.

But neither that amount nor the $50,000 annual contribution is finalized.

I'm still working through the math.

And here's the really uncomfortable part.

Maybe the smartest financial decision isn't always to save more.

Maybe it's to recognize when I've saved enough for a particular goal.

Maybe it's to take the trip.

Buy the ticket.

Sign up for the class.

Or spend a random weekend in the mountains without calculating what that money could have earned over the next 20 years.

I know.

Revolutionary thinking from someone who works in finance.

Please respect my privacy during this difficult transition.

Meanwhile, I Moved to Colorado and Decided to Have a Life

In March 2026, I moved to Colorado.

New job.

New home.

New neighborhood.

New people.

A whole new chapter.

Because apparently, moving across the country in your mid-40s sounded like a perfectly reasonable way to shake things up.

And you know what?

It was.

I've spent a lot of my life building my career, creating financial security, and figuring out how to get to the next milestone.

But I also want to build a life that feels full right now.

Not in 2030.

Not at 65.

Now.

Which brings me to another one of my slightly ridiculous projects.

The Colorado Years: 44 Adventures Before 2030.

Why 44?

Because I was 44 when I moved to Colorado and decided to start this chapter.

Forty-four adventures to celebrate the age when I chose to shake things up.

Yes, I created a list.

Yes, I'm tracking my progress.

I know. I have a problem.

But I love this project.

I've ridden the Pikes Peak Cog Railway, attended my first CU Buffs football game, and experienced my first Colorado Avalanche game.

Three adventures down.

Forty-one to go.

Some will be big.

Some will be small.

Some will probably involve me discovering that I'm not nearly as coordinated as I think I am.

But that's okay.

I want to try things.

I want to be strong. Healthy. Curious. Brave.

I want to make new friends, deepen existing relationships, laugh more, and continue becoming someone I genuinely enjoy being.

I want to be my best physically, mentally, and emotionally.

And I don't want to wait until retirement to get there.

Because imagine reaching financial independence only to realize you've spent years neglecting everything else that makes life worth living.

That's not retirement.

That's just a really well-funded identity crisis.

The Life Portfolio (Yes, I Made Another Portfolio)

Somewhere along the way, I realized I was managing my financial investments with incredible discipline.

But was I investing the same energy into my actual life?

My health?

My friendships?

My relationships?

My happiness?

My sense of adventure?

Not always.

So I started thinking about those things as my Life Portfolio.

And yes, I'm aware that I've turned personal fulfillment into an asset allocation exercise.

At this point, it's a personality trait.

But I like the concept.

Financial wealth gives us resources.

Physical health gives us the ability to use them.

Relationships give us people to share experiences with.

Curiosity gives us reasons to keep exploring.

And time gives us the opportunity to put it all together.

I want all of it.

Not just the money.

Talking About Money on the Internet. What Could Possibly Go Wrong?

I've debated how much of this journey to share.

Money is personal.

And the FIRE—Financial Independence, Retire Early—community can be an interesting place.

There are people with tremendous experience and valuable insights.

There are also people who are still figuring things out, which is perfectly fine.

But sometimes it's hard to tell who's sharing a proven strategy and who's sharing an enthusiastic theory with a really attractive spreadsheet.

And as someone who loves a spreadsheet, I know how convincing those can look.

I want to learn from people who have actually navigated early retirement.

I want to ask questions.

Challenge assumptions.

Understand the tax implications.

And figure out what works for my circumstances.

I'm not here to pretend I've mastered all of it.

Quite the opposite.

I'm here to share what I'm learning.

My goals.

My progress.

My decisions.

My mistakes.

And, of course, my pivots.

There will be pivots.

I am practically a professional pivoter at this point.

What I won't be doing is publishing every account balance, every transaction, or a detailed map of my personal finances.

Because sharing my journey is one thing.

Giving the entire internet a guided tour of my financial underwear drawer is another.

Let's maintain a little mystery.

What Happens If I Change My Mind?

Here's another confession.

I might not stop working entirely in 2030.

I know. Plot twist.

Maybe I'll do consulting.

Maybe I'll work on projects that interest me.

Maybe I'll write more.

Maybe I'll discover an opportunity I can't imagine today.

Or maybe I'll decide that I love waking up, drinking coffee, walking Harvey, working out, and having absolutely nowhere I need to be.

That sounds pretty fantastic, too.

The important thing is that I want to have the choice.

Not work because I need the paycheck.

Work because I want to.

Or don't.

That's the dream.

Retiring Toward Something

When I first started planning for financial independence, I thought the hardest part would be accumulating the money.

Save enough.

Invest consistently.

Reach the number.

Done.

But now I'm beginning to think the harder part might be figuring out what I actually want my life to look like once I get there.

What does an ordinary Tuesday look like?

Who am I spending it with?

What am I learning?

Where am I going?

What am I doing that makes me excited to get out of bed?

Those questions are much harder to answer than a compound interest calculation.

And believe me, I've tried putting them in Excel.

So here's where I am.

I'm working toward $2 million.

I'm building a five-year bridge.

I'm exploring a Roth conversion ladder.

I'm trying to determine how much I actually need to save.

And somewhere in between all of that, I'm trying to build a life full of experiences, meaningful relationships, good health, and ordinary joy.

I'm not throwing away the spreadsheet.

Let's not get carried away.

But I'm finally recognizing something.

The spreadsheet is supposed to support my life. My life isn't supposed to support the spreadsheet.

So here's to the road to 2030.

The financial goals.

The adventures.

The mistakes.

The lessons.

The inevitable pivots.

And maybe, just maybe, learning to spend a little money without immediately calculating its future value.

Baby steps.

Because I'm not trying to retire from my life.

I'm trying to build a life I can't wait to retire toward.

And I have every intention of enjoying the journey.

This is my personal financial journey, not financial or tax advice. Financial goals, projections, tax rules, and personal circumstances can change. I'm sharing my process, not prescribing a plan for anyone else.

Some Days You Get Flowers. Some Days You Get Poop.

On unexpected kindness, dumpster fires, and finding joy when life goes sideways.

I've had a couple of days.

You know the kind.

The kind where you leave work wondering how you managed to maintain your composure when every fiber of your being wanted to scream.

The kind where you replay conversations in your head, question decisions, and wonder how you're going to navigate whatever fresh disaster tomorrow has in store.

The kind where you think:

What. The. Actual. Fuck.

And then you go home.

And your dog poops on your brand-new carpet.

Because apparently, the universe has a sense of humor.

The People Who Show Up

I've been thinking a lot about relationships lately.

Not just romantic relationships. Friendships. Colleagues. The people who make up our lives.

And something I've noticed is that the people who show up for you aren't always the people you expect.

Sometimes the people you thought you were closest to aren't there when you need them.

And that's a strange feeling.

You start questioning things.

How did we get here?

When did this relationship change?

Was I imagining how close we were?

It's not necessarily that anyone did something terrible. Sometimes people just don't show up in the ways you thought they would.

And it can be surprisingly disappointing.

But here's the other side of that.

Sometimes the people you least expect are the ones who remind you what genuine kindness looks like.

Monday was rough.

Really rough.

And a friend invited me over for dinner.

Now, this is not someone with an abundance of free time. Quite the opposite.

But somehow, in the middle of an incredibly busy life, this person made time for me.

Made me dinner.

Listened while I complained.

And complained.

And probably complained some more.

No judgment. No expectation that I needed to be cheerful or entertaining. No requirement to have everything figured out.

Just dinner, conversation, and someone willing to listen.

And you know what?

Sometimes that's everything.

The problems didn't magically disappear.

I still had to go back to work the next day.

But for a few hours, I didn't have to carry all of it by myself.

And Then There Were Flowers

Tuesday wasn't much better.

In fact, by the end of the second day, I was feeling pretty overwhelmed.

And then flowers arrived.

From another friend.

Someone who knew I'd been having a difficult couple of days and decided to do something thoughtful.

Flowers.

That's it.

No elaborate speech. No grand gesture. Just a little reminder that someone was thinking about me.

And it completely brightened my day.

It's funny how something so simple can change your mood.

A few flowers can't fix a difficult work situation.

But they can make you smile in the middle of one.

And sometimes that's exactly what you need.

A Meeting of the Minds. Sort Of.

Earlier that afternoon, following a particularly rough meeting, I had another call scheduled.

Naturally, my computer speakers decided this was the perfect time to stop working.

So I had to join from my phone.

Excellent.

Because when your professional life is already feeling slightly chaotic, nothing says I've got this under control quite like technology refusing to cooperate.

But the two colleagues on the call were hilarious.

We joked about the situation.

We laughed.

And for a few minutes, I forgot how frustrated I'd been.

It was a meeting of the minds.

Or at least a meeting of one phone, two functioning speakers, and three people trying to get through the day.

And one of those colleagues even offered to find time to help me work through some of the craziness happening at work.

Again, someone making time.

Someone recognizing that I could use a little help.

Someone showing up.

And I started noticing a pattern.

The people who made these difficult days better weren't necessarily the people I would have expected.

They were simply the people who showed up.

With dinner.

With flowers.

With laughter.

With their time.

Cue Cinderella

Now, you'd think that after two difficult days, the universe might decide I'd had enough.

Perhaps a peaceful evening.

A nice workout.

A little time to myself.

HAHAHAHA.

No.

I walked downstairs to work out.

And there it was.

Dog poop.

Lots of it.

On my brand-new carpet.

The carpet I had just paid to have installed.

The carpet that was supposed to make my newly renovated house feel beautiful and finished.

POOP.

Cue Cinderella.

Except Cinderella was not singing to woodland creatures.

Cinderella was swearing.

A lot.

Out came the OxiClean.

Then the Hoover floor spray.

Then Nature's Miracle.

At one point, I was fairly certain I had enough cleaning products on that carpet to qualify as a small chemical laboratory.

And there I was.

On my hands and knees.

Scrubbing dog poop.

With gloves on, of course.

After two of the most frustrating workdays I'd had in a while.

Living the dream.

Bibbidi-bobbidi-POOP.

And because apparently cleaning the carpet wasn't enough, I also ordered a Little Green Machine.

Nothing says I've really made it in life quite like an emergency carpet-cleaner purchase.

But here's the thing.

After the swearing, scrubbing, spraying, and online shopping...

I still worked out.

Mindset Is Everything. Even When You're Pissed.

I've spent a lot of time thinking about mindset.

About resilience.

About being 1% better.

About building habits and routines that support the life I want.

And sometimes I think we make all of that sound far more glamorous than it actually is.

We imagine resilience as some beautiful moment of personal growth.

Someone standing on a mountaintop, looking into the distance, having a profound realization about life.

Meanwhile, I'm standing in my basement holding a bottle of Nature's Miracle and wondering whether my dog has personally declared war on my carpet.

Not exactly inspirational-poster material.

But maybe that's the point.

Mindset isn't about being happy when things go wrong.

It's not about pretending a terrible day was wonderful.

And it's certainly not about being grateful for dog poop.

It's about flexibility.

It's about recognizing that things aren't going according to plan and deciding what you're going to do next.

I wanted to work out.

Instead, I had to clean the carpet.

So I cleaned the carpet.

I swore.

I got frustrated.

I ordered a carpet cleaner.

And then I worked out.

Not because I was feeling particularly enlightened.

But because I wasn't going to let one more ridiculous thing derail something important to me.

Sometimes being 1% better isn't about doing something extraordinary.

Sometimes it's simply returning to the plan after life interrupts it.

Two Things Can Be True

Here's what struck me as I walked Harvey the next morning.

The past two days were hard.

Really hard.

And yet, when I started thinking about them, I realized they were also filled with some genuinely wonderful moments.

Someone made me dinner.

Someone sent me flowers.

Someone made me laugh.

Someone offered to help.

And somewhere in the middle of all that, my dog pooped on the carpet.

Two things can be true.

You can have a terrible day and still experience something wonderful.

You can be disappointed by people you thought would show up and deeply grateful for the ones who did.

You can be frustrated, overwhelmed, and angry while still recognizing the kindness around you.

You can love your dog and seriously question his judgment.

And you can believe in the importance of a positive mindset while occasionally swearing like a sailor.

Maybe the goal isn't to eliminate the hard days.

Maybe it's to get better at noticing that the hard days aren't the whole story.

Finding Joy in the Dumpster Fire

When I started Retire Toward, I was thinking about financial independence.

Building enough money to create options.

Building a life I wouldn't want to retire away from.

But building a wonderful life doesn't mean every day is going to be wonderful.

Some days, everything seems to be moving toward a full-blown dumpster fire.

Work gets complicated. Relationships disappoint you. Your carefully planned evening turns into an unexpected date with a bottle of Nature's Miracle.

And yet, somewhere in the middle of all that chaos, life surprises you.

Someone makes you dinner.

Someone sends flowers.

Someone makes you laugh when you desperately need it.

Someone makes time for you when they barely have any to spare.

None of those things puts out the dumpster fire.

But they remind you that not everything is burning.

And maybe that's what I've been reminded of this week.

Don't let everything that's going wrong blind you to the unexpected joy that's still happening.

I don't know what the next few days at work will bring. Hopefully a couple of them involve working remotely in sweatpants.

But I do know there are good people in my life. People who show up in ways I didn't expect.

And there are moments worth appreciating, even when everything else feels overwhelming.

Sometimes those moments are small.

Sometimes they're unexpected.

And sometimes they're exactly what you need.

Because building a wonderful life isn't about eliminating the dumpster fires.

It's about building a life where you can still find joy in the middle of one.

And if all else fails?

Buy a Little Green Machine.

Because some days you get flowers.

And some days you get literal poop.

Retire Toward. Not Away.

Someone You Can Exhale With

Finding the extraordinary in ordinary moments.

Every once in a while, someone comes into your life who completely disrupts your expectations.

Not because they're perfect.

Not because they check every box.

But because there's something about them that just feels different.

I've been dating. A lot. More than I want to admit.

Enough to have collected some entertaining stories, a few questionable experiences, and more than a handful of moments where I've wondered if being single might actually be the better option.

And then there's him.

The man who might just ruin all the men after him.

Not intentionally, of course. He probably doesn't even know he's doing it.

But once you've experienced a certain kind of connection, it's difficult to pretend that something less feels like enough.

It's Not About the Grand Gestures

He's successful. Intelligent. Confident. The kind of man who can walk into a room and command attention without demanding it.

He's also incredibly kind and thoughtful.

He listens. Really listens.

He asks questions. He challenges my thinking. He offers perspectives I hadn't considered.

And the conversation flows effortlessly.

I could talk to him for hours.

But what gets me isn't his success or his confidence.

It's the little things.

Because sometimes, when the day just plain sucks, you need someone to bitch to while they make you dinner.

Someone who listens to your frustrations and doesn't feel the need to fix everything.

Someone who lets you be yourself. Not the polished, professional version of yourself who spends the day solving problems, making decisions, and keeping everything moving forward.

Just you.

Maybe you've had a little too much wine. Maybe you've complained about the same thing three times. Maybe tomorrow you'll wake up and realize none of it was quite as catastrophic as it seemed.

But tonight, you just need someone to listen.

And there's something incredibly comforting about that.

Then there are the other evenings.

The ones where you watch a documentary that really makes you think. Where you share conversations about life, people, and the world around you.

And eat chicken fingers so terrible they probably wouldn't even qualify as dog food.

And then there are the completely ridiculous moments.

Like when your workout coach announces, halfway through a Monday glute workout, that you're officially "done with butt stuff."

Yes. Butt stuff.

Naturally, I found this hilarious.

And naturally, I had to share it.

What started as an innocent comment about a glute workout somehow became the running joke of the evening. The kind where you keep finding ways to bring it back into the conversation, and every time, it's just as funny as the first.

We laughed. And laughed some more.

Over butt stuff.

Because apparently, we're twelve.

And I loved every minute of it.

Not exactly the stuff of romantic movies.

But somehow, those are the moments that stick with you.

The ordinary ones.

The ridiculous ones.

The ones where you're simply enjoying another person's company.

And maybe that's what makes them extraordinary.

The Man Who Raises the Bar

Here's the thing about meeting someone like him.

He changes what you notice.

After spending time with someone who makes conversation feel effortless, you notice when you're carrying the entire conversation on a first date.

After being with someone who is genuinely curious about your thoughts, you notice when someone never asks a question.

After experiencing kindness, affection, and genuine connection, you realize how often you've accepted less.

There's something incredibly attractive about a man who can be confident and gentle at the same time.

Someone who makes you feel wanted without making you feel pressured.

Someone who makes an ordinary evening feel extraordinary simply by being thoughtful.

It's not that other men suddenly become less interesting.

It's that your understanding of what connection can feel like has changed.

And once you know, you know.

You can't unknow it.

The Problem With the Checklist

Of course, there's a catch.

There always seems to be a catch.

He has a complicated life. A history. Responsibilities. Commitments.

And I have a life I've worked very hard to create.

A life built around independence, adventure, freedom, and the ability to decide what comes next.

On paper, we don't necessarily make sense.

In fact, if I were creating a checklist of everything I thought I wanted in a partner, he would probably fail a few important categories.

Which is both wonderful and slightly terrifying.

Because I've learned that chemistry and compatibility aren't always the same thing.

You can have an extraordinary connection with someone whose life doesn't quite fit yours.

And recognizing that doesn't make the connection any less extraordinary.

But perhaps the bigger realization is that I've spent so much time thinking about what I want in a partner that I haven't always stopped to consider how I want to feel with one.

And those are two very different things.

Someone Who Feels Like Home

I've spent a lot of my life building a home.

Not just the physical kind, with walls and furniture and a mortgage, but a life that feels like mine.

I've moved across the country. Started over. Built a career. Created new routines. Made new friends. Learned to embrace change and find happiness in my own company.

I've worked hard to create a life that I genuinely love.

And I'm proud of that.

But somewhere along the way, I've realized something.

I'm not looking for someone to complete my life. I'm looking for someone who feels like home.

Someone whose presence makes the world a little quieter.

Someone I can laugh with, be vulnerable with, and simply exist beside.

Someone who makes me feel safe, wanted, understood, and cared for.

Someone who doesn't require me to be impressive, accomplished, entertaining, or constantly moving toward the next big thing.

Someone who lets me just be me.

Because sometimes it's just nice to share a little bit of your world with someone else.

Not every evening needs to be an adventure.

Not every conversation needs to be profound.

And not every moment needs to be a lesson in personal growth.

Sometimes I just want to sit beside someone, laugh about the absurdities of life, and enjoy being together.

No expectations. No performance. No need to be anything other than who we are.

I've realized that I don't need someone to give me a wonderful life.

I already have one.

I just want someone who makes sharing it feel wonderful, too.

Recognizing My Own Patterns

Here's where the story gets a little more complicated.

He's exactly the kind of man I've always been attracted to.

Accomplished. Intelligent. Charismatic.

And, if I'm being completely self-aware, perhaps a little complicated.

I recognize the pattern.

I've lived it before.

There's something about a man with a big life that draws me in. Someone with ambition, confidence, and a world of his own.

But I've also learned that having an incredible connection with someone doesn't necessarily mean there's room for you in that world.

That's the part I'm still figuring out.

Because I don't want to spend my life chasing moments of connection with people who can't offer consistency.

I want both.

The butterflies and the reliability.

The chemistry and the companionship.

The independence and the intimacy.

And I don't think wanting all of those things is asking too much.

But I also don't need to have all the answers today.

Sometimes it's okay to enjoy a connection without immediately trying to determine where it will lead.

The Beauty of Being Able to Exhale

Maybe the lesson isn't about finding the perfect man.

Maybe it's about recognizing that perfection was never the goal.

We all come with histories, responsibilities, fears, and complications.

We all have pieces of our lives that don't fit neatly into someone else's expectations.

And sometimes the most remarkable people arrive wrapped in circumstances we never would have chosen.

That doesn't make them wrong.

It makes them human.

I don't know what the future holds with him.

And for once, I'm not particularly interested in trying to figure it all out tonight.

What I do know is that I enjoy him.

I enjoy our conversations. Our laughter. The quiet moments. The affection.

I appreciate his kindness and thoughtfulness.

I appreciate having someone in my life who reminds me how wonderful genuine connection can feel.

And perhaps most importantly, I appreciate being able to just be myself.

The ambitious version.

The adventurous version.

The occasionally frustrated, slightly over-served-on-wine version.

All of it.

Because I've spent so much of my life moving forward, setting goals, solving problems, and figuring out what's next.

And sometimes, it's just nice to stop.

To sit beside someone.

To share a little bit of your world.

To feel completely comfortable in your own skin.

To exhale.

Maybe he'll be part of my life for a season.

Maybe he'll be part of something much longer.

I don't know.

And that's okay.

Maybe he'll even convince me to drink milk.

No way. Never.

Because not every meaningful connection needs an immediate destination.

Some people enter your life to stay.

Some enter your life to teach you something.

And some simply remind you what you've been looking for all along.

Maybe he isn't the man who ruins all the men after him.

Maybe he's the man who reminds me what home is supposed to feel like.

Because maybe finding someone who feels like home isn't about finding someone perfect.

Maybe it's about finding someone you can exhale with.

Retire Toward. Not Away.

Resilience: Apparently, This Wasn't the Plan

Or: How I Got Really Good at Starting Over

If there's one thing I've learned in my forty-something years on this planet, it's that life rarely goes according to plan.

At least not MY plan.

I've had some pretty good plans.

Excellent plans, actually.

Well-researched. Financially responsible. Occasionally accompanied by spreadsheets.

And then life comes along and says:

LOL. NO.

I wanted to be an air traffic controller.

That didn't work out.

I went to Oklahoma, gave it everything I had, and failed.

Not the inspirational kind of failure where you immediately discover your true calling and ride off into the sunset.

The ugly kind.

The crying-for-hours-in-the-car kind.

The moving-on-to-your-sister's-couch kind.

The what the fuck am I supposed to do now? kind.

So I got a job working in a photobooth.

Not exactly the career trajectory I'd envisioned.

But eventually, I found my way into a university job.

And then another opportunity.

And graduate school.

And leadership positions.

And different states.

Different people.

Different versions of myself.

Some of those transitions were exciting.

Some were heartbreaking.

Some were decisions I made because staying was easier, but I knew it wasn't right.

And some were decisions made for me.

But here's what I've started to realize.

Resilience isn't always bouncing back.

Sometimes it's sitting on your sister's couch with absolutely no idea what comes next.

Sometimes it's walking away from a job that looks wonderful on paper but feels terrible in your gut.

Sometimes it's being the oldest beginner in the room.

Sometimes it's admitting that the plan you've spent years pursuing isn't the plan you want anymore.

And sometimes it's getting up the next morning, making coffee, and figuring out one small thing you can do.

Not because you're fearless.

But because life keeps moving.

And eventually, so do you.

The Four-Year Rule

I have a theory. And like most of my theories, it started with me making a fairly dramatic life decision and then trying to explain it afterward.

What if we treated living somewhere new the way we treat college?

Four years. A new place. New people. New experiences. A chance to learn something about yourself.

And at the end? You decide whether you want to stay.

Charlottesville Was Basically College

I left Columbus, Ohio, after about a decade. I had a career, friends, routines, and a life that looked perfectly reasonable from the outside.

Then I took a fellowship in Charlottesville, Virginia. I'd never even visited before accepting the job. Naturally, I decided moving there was a great idea.

New city. New job. New people. I figured I'd give it a shot.

I learned a lot. I met people I never would have met otherwise. Some of them are still part of my life. And eventually, I realized I was ready for another chapter.

About four years later, I moved to Colorado.

Apparently, I'd graduated from Charlottesville.

The Four-Year Rule

We send people off to college for four years and expect them to grow, explore, make friends, try new things, and figure out who they are.

Why couldn't we approach a new city the same way?

Four years to explore. To build a routine. To find your coffee shop. To make friends. To get lost, then learn your way around. To try things you might never have tried if you'd stayed where everything was familiar.

And then you get to ask: Do I want another four years here?

You can stay. You can leave. You can split your time between two cities. You can change your mind.

You're not failing if you leave. You're graduating.

My Colorado Experiment

Now I'm in Colorado, and I'm thinking about what I want this chapter to look like before 2030.

I don't want to spend my time here only working, running errands, and saying I should really go see that place someday.

So I'm giving myself a project: 36 experiences in 36 months. A reason to get out, explore, try something new, and collect a few stories along the way.

Some will be big adventures. Some will probably involve me being terrible at something in public. That's fine. I have experience with that.

The point isn't to squeeze every possible activity out of Colorado. It's to actually live here while I'm here.

You Don't Have to Know the Ending

Maybe I'll move back to Columbus. Maybe I'll split my time. Maybe I'll discover something I haven't even considered yet.

I don't have to decide the ending before I've lived the chapter.

That's the part I like about the four-year rule. It makes a move feel less like a forever decision and more like an invitation.

Go. Learn. Meet people. Build a life. See what happens.

And when the four years are up?

You get to choose what comes next.

It's Always the People

I went back to Columbus for a long weekend and managed to schedule approximately 47 social engagements in three days.

By Sunday, my sleep was a disaster, my stomach was staging a protest, and I desperately needed a nap.

Apparently, I now need a vacation to recover from visiting my friends.

But here's the thing.

I wasn't there for the restaurants. Or the shopping. Or even the football.

I was there for the people.

The people I've known for 15 years. The people I worked with a lifetime ago. The people going through hard things. The people who are genuinely happy when something good happens to me.

And the people I can sit with and do absolutely nothing.

One afternoon was bagels, Starbucks, and hanging around while someone watched sports. Nothing extraordinary. No elaborate plans. No life-changing adventure.

And it was lovely.

I had brunch with a former coworker I've known since 2011. We don't see each other often, but somehow we pick up exactly where we left off.

Another friend and I caught up about life, work, and everything in between. Years have passed. Jobs have changed. We've all gotten older. Rude, frankly.

But the conversations still feel familiar.

That's what struck me about this trip.

Some people enter your life completely by accident. A job. A random introduction. Maybe even a dating app. LOL.

You have absolutely no idea what role they're going to play.

And then, years later, they're still there.

Not necessarily talking every day. Not always living in the same city. But when you see each other, there's no performance required.

You can just be yourself.

I've spent years thinking about retirement in terms of numbers. Savings rates. Investment balances. How many more years until I can stop working?

And those things matter. I'm not abandoning my spreadsheets. Let's not get crazy.

But this weekend reminded me that I've been building another kind of wealth all along.

Relationships.

People who listen. People who make me laugh. People who tell me what I need to hear. People who are genuinely happy for me.

People who feel like home.

Maybe that's what retiring toward something actually means.

Not just having enough money to leave work.

Having enough freedom to spend ordinary Tuesdays with extraordinary people.

Or even completely ordinary people who happen to be extraordinary to you.

Because at the end of the day, it's not really about where I live, what I do, or how much money I've saved.

It's the people. It's always the people.

Sometimes You Have to Promote Yourself

There were about 15 pairs of identical black shoes under her desk.

They weren't really my style.

There was also a fish tank. Boxes everywhere. And when the woman who managed our medical supplies retired, I got a much closer look at our inventory room.

Powdered gloves ordered for a provider who had left years earlier.

Expired supplies.

And more varieties of bandages than any reasonable human being could possibly need.

Welcome to a university health center.

I fucking loved that place.

I landed there during a big university reorganization after my boss left. I was making about $42,000 as a fiscal officer. I picked up the health center and became a Business Manager making about $55,000.

The health center was roughly a $21 million operation.

Family medicine. Women's health. Pharmacy. Lab. Radiology. Dental.

My degree was in accounting, so I understood the numbers. Now I had to learn healthcare—insurance billing, revenue cycle, fee schedules, vendors, pharmacy inventory, capital equipment and an approximately $8 million building renovation.

So I learned it.

I've always thought businesses are a little like ice cream.

Different flavors. Same basic ingredients.

The health center was just a new flavor.

And the people were freaking hilarious.

We had Talk Like a Pirate Day. We bubble-wrapped someone's office. People stole things from my office and left ransom notes.

Someone came back from PTO to a sign that said:

TAKE A SEAT.

There were something like 200 chairs in their office.

This was apparently how responsible adults operated a $21 million healthcare business.

😂

Fine. I'll Get the Master's.

Eventually, I was told that not having a master's degree was holding me back.

One small problem with that argument:

My former boss had made around $90,000.

He didn't have a master's degree.

Cool.

Fine. I'll get the master's.

I enrolled in a 13-month Master of Business Operational Excellence program while working full time.

I went because I needed the credential.

But it changed the way I thought about work.

Accounting taught me to understand the numbers.

Operational Excellence taught me to see the system behind the numbers.

Which brings us back to those powdered gloves.

For my master's project, I tackled our medical supply inventory.

Instead of asking who screwed it up, I started asking why the process allowed it to happen.

Did we really need roughly 300 different supply items? Could we standardize? Buy in bulk? Negotiate better contracts? Stop every department from ordering its own stuff?

We cut roughly 300 items to fewer than 100.

We standardized supplies, negotiated contracts, established minimums and maximums, used FIFO, and built a student team to replenish everything.

The system worked without me standing there holding it together.

That became one of my career philosophies:

Learn the business.

Improve the system.

Make it sustainable.

Then go find the next problem.

Eventually, the next problem was my career.

Perfect. Now It's Time to Go.

I had taken on a more complicated operation.

I had learned healthcare.

I had improved systems.

And now I had the master's degree I had been told I needed.

I was making about $55,000 and wanted the next promotion.

The organization didn't particularly want to give it to me.

So I pushed.

Eventually, I became a Business Manager 2 and went from roughly $55,000 to $74,000.

My working title before?

Business Manager.

My working title after?

Business Manager.

Perfect.

Now it's time to go.

I started looking.

My next job paid in the low $90,000s.

Bye, old department.

😂

And here's the part that matters:

I loved the health center.

I loved the people. I loved the work. I learned an enormous amount there.

Leaving doesn't mean the chapter was bad.

Sometimes you can love a job and still realize you've learned what you came to learn.

Over time, my career philosophy became pretty simple:

Year one: Learn it.
Year two: Improve it.
Year three: Make it take less of your time.

Still learning and growing?

Stay.

Done learning?

NEXT.

An organization gets to decide what it's willing to pay you.

It gets to decide whether it's willing to promote you.

It does not get to decide what you're worth.

Sometimes you have to promote yourself.

Build the money. Build the life.

I Failed Out of Air Traffic Control School

On the way to Oklahoma to become an air traffic controller, I ended up stranded on the side of the freeway with my sister, a 2001 Lexus IS, and what appeared to be a pile of birdseed in my lap.

It was actually everything-bagel seasoning.

This distinction did not make the situation look any better.

We had left Cleveland with Bialy's (the BEST) everything bagels for the roughly 15-hour drive to Oklahoma, where I was headed to the FAA Academy.

At some point, the car stopped cooperating.

Then a cop pulled over.

Not just a cop.

Possibly the hottest cop I had ever seen.

Naturally.

He asked what was wrong.

My sister and I basically responded:

We don't know.

Then giggled like idiots.

He popped the hood. I went to get the little stick that held the hood up.

It rolled underneath the car.

So now I'm lying down on the side of the freeway trying to retrieve it when Hot Cop tells me to get up because everyone driving past is going to think he's making me do push-ups.

Excellent.

Eventually he drove us to get gas.

He was apparently headed to a shooting range, because I climbed into the back seat and my sister was in the front seat of the car and there were rifles sitting next to me.

Then his wife called.

And somewhere in all of this, I stood up and discovered that the everything-bagel seeds had collected in my lap and were now falling off me like I'd been sitting in a pile of birdseed.

This was how I began my exciting new career in air traffic control.

Things were going great.

Why Not Try?

I'd been working as an accountant for about six years.

I was making around $39,000, and I wanted to try something different.

For some reason, government work fascinated me. Maybe I'd watched too much X-Files.

I even took the FBI agent test once.

Didn't exactly crush that one.

Apparently Special Agent Scully and I were not destined to become coworkers. But, I would have been open to a secret romance with Agent Fox Mulder.

Then I found air traffic control.

I took an eight-hour test in Baltimore.

I studied.

I got accepted to the Academy.

And unlike applying for another accounting job, there wasn't really a way to casually try this out.

I had to quit my job.

Move to Oklahoma.

Go all in.

Put all my eggs in one basket.

So I did.

Why not try?

Oklahoma Was Fucking Wild

I lived in Mustang, Oklahoma.

And the Academy was mentally exhausting.

All day, your brain was on.

Learning. Practicing. Simulating. Trying to understand everything happening around you and make the right decision quickly.

And then we'd get out of class.

Apparently the appropriate response to intense federal aviation training was absolute chaos.

There were parties.

Lots of drinking.

People were away from their spouses and, let's just say, some of them appeared to be temporarily single and on the prowl.

There was a bar where everyone would be dancing and then the dance floor would suddenly clear for:

LIVE BULL RIDING.

Inside the bar.

Because Oklahoma.

My classmates once convinced me to put bar glasses in my purse when we went to a bar.

One of the married guys in my class called me one night to come pick him up from a questionable situation.

So I did.

I was having a fucking blast.

And then I discovered perhaps Oklahoma's greatest contribution to civilization.

SUPER TARGET.

I had never been to a Super Target.

It had an Einstein Bros. Bagels inside.

HEAVEN.

Apparently bagels were an important supporting character in this period of my life.

Our instructor even made biscuits and sausage gravy one day.

I tried it.

Still not a fan.

😂

And then there was the earthquake.

I Have Seen Movies

We're sitting in class one day when the fucking building starts shaking.

EARTHQUAKE.

I immediately grabbed the desk.

Everyone else seemed bizarrely calm about this development.

Excuse me?

I have seen movies.

Buildings crumble.

My instinct was not:

Let's remain seated and see where this goes.

My instinct was:

GET THE FUCK OUT OF THE BUILDING AND SAVE YOURSELF.

Apparently this was not the approved response.

So I stayed.

The ceiling did not collapse.

I did not die.

Everyone else was fine.

I still think they were wrong.

Next time, I'm getting the fuck out.

😂

It was exhausting.

It was ridiculous.

It was fun.

I had built a whole little life in Oklahoma.

And I really thought it was about to become my actual life once I went to my assigned airport in Maumee, Ohio.

Then I failed.

Apparently I Don't Speak Midwestern

The simulators and I had some issues.

They were supposedly set to recognize a Midwestern dialect.

I am from Ohio.

Apparently I did not learn the approved Midwest dialect.

For whatever reason, the simulator had a particularly difficult time recognizing my A sound.

Like the A in apple.

Which is a weird problem to discover after you've quit your job and moved 15 hours away to become an air traffic controller.

I also wasn't talking to enough planes.

Turns out that's somewhat important.

Then came the final evaluation.

Sudden death.

I landed a simulated airplane on another airplane.

In my defense:

Bro should have taken off.

He did not.

And that was it.

I washed out.

The Drive Home

Air traffic control was one of the hardest career failures I've ever experienced.

I think part of it was because I had gone all in.

There was no old job waiting for me.

No backup plan.

I had put all my eggs in one basket.

And then dropped the fucking basket.

My best friend came to Oklahoma and drove me home.

Another roughly 15-hour drive.

But it couldn't have felt more different from the drive there.

On the way out, I'd had my sister, everything bagels, Hot Cop and an entire future waiting for me.

On the way home, I cried.

For hours.

The rain on my face lasted for hours as she drove.

I had no job.

I didn't have my own place to go home to.

I ended up on my sibling's couch.

And I felt like a failure.

Everyone else's life seemed to keep moving.

Mine felt like it had stopped.

And I don't remember having someone who could tell me exactly how to put it back together.

People cared about me.

My best friend literally drove 15 hours home with me.

But nobody could rebuild this for me.

I had to be the rock for myself.

Apparently this would become a recurring theme in my life.

Me, amping me up.

😂

It's funny now.

It wasn't funny then.

I Tried to Go Back

I wasn't ready to let it go.

I took flying lessons in Cleveland.

In winter.

Because apparently I enjoy making difficult things even more difficult.

My instructor, Tony, was a badass who had flown in horrible conditions.

Then someone pointed out that if something happened to Tony while we were in the air, I would have to land the plane.

This was concerning information.

I also discovered that I could get spectacularly airsick in a tiny airplane.

At one point I was sitting there clutching a garbage bag.

Eventually, I had to accept something I didn't want to accept.

I wasn't going back.

Sometimes resilience means trying again.

Sometimes it means accepting that you're not getting the ending you wanted.

And finding another one.

$36,000 and a Room From Craigslist

There was no dramatic comeback.

In January, I got a job working for a photobooth company.

I found this deeply embarrassing.

Then a friend told me the university was a good place to work.

So I applied.

I drove to the interview from the photobooth job in my Honda.

No air conditioning.

Traffic.

Rerouted.

Late.

Sweaty.

Obviously, they hired me.

😂

On March 15, 2011—the Ides of March—I started my new job making about $36,000.

Less than I'd been making before I left for Oklahoma.

And it felt like a million bucks.

I packed my stuff into my car and rented a room I found on Craigslist from a woman who worked as a nurse at the university.

That was the comeback.

A $36,000 job.
A room in someone else's house.
A car full of my stuff.

Nothing about it looked particularly impressive.

But my life was moving again.

There Is No Straight Line

It's easy to look backward and make a career look intentional.

Mine certainly wasn't.

There was a giant fucking hole in the middle where I quit my job, moved 15 hours away, discovered Super Target, survived an earthquake, failed out of air traffic control school, cried all the way home, worked for a photobooth company and rented a room from a stranger.

The line only looks obvious when you already know where it ends.

I didn't know.

I just kept finding the next thing.

Looking back now, I'm glad I went to Oklahoma.

I'm glad I tried.

I'm glad I lived in Mustang.

I'm glad I met those crazy people.

I'm glad I experienced the Academy.

I'm glad I discovered Super Target and its Einstein Bros. Bagels.

I'm even glad I tried flying afterward.

It was a great experience.

It just didn't have the ending I wanted.

Failing at something doesn't erase the experience of trying it.

I got to have that chapter.

Then I had to build another one.

And another one.

And another one.

Apparently I've spent a lot of my life standing in my own corner yelling:

YOU CAN FUCKING DO THIS.

Maybe that's not the worst thing air traffic control taught me.

Build the money. Build the life.

The Best $70 I Ever Spent

I have spent $70 on some truly stupid shit in my life.

This was not one of those times.

Although, technically, I didn't even know I had spent it.

Years ago, when I was a college student, I worked for the university. Student employees were supposed to sign paperwork opting out of the state pension system.

Apparently I screwed that up.

Thank God.

I worked enough that somehow about $70 of my student wages ended up in OPERS, Ohio's public employee retirement system.

I completely forgot about it.

Nearly two decades later, that $70 came back to save my ass.

I cannot stay another month.

By 2021, I had spent almost ten years working in Ohio's public university system.

Nine years and eleven months.

And I was done.

Not maybe I should start looking around done.

Done done.

The work situation had become so bad that when I called OPERS to talk about rolling my pension out, I told them:

“The situation here is dire. I cannot stay another month.”

This presented a problem.

OPERS had different refund provisions based on years of qualified service. At more than five but less than ten years, the additional refund amount was 33% of eligible contributions.

At ten years, it jumped to 67%.

And there I was.

Nine years. Eleven months.

Of course I was.

The financially sensible thing seemed obvious: suck it up for one more month.

Except I didn't want one more month.

I wanted out.

Then OPERS found College Me.

While I was talking with the OPERS representative, they noticed something in my history.

Apparently, I had paid into OPERS years earlier when I was a student employee.

I vaguely remembered the whole thing.

Student workers had paperwork to sign so we wouldn't contribute to the pension.

Apparently I didn't.

Or didn't do it correctly.

Or worked too much.

Who knows.

But there it was.

That tiny contribution from a college job I'd almost completely forgotten about.

And it gave me the service I needed to get over the ten-year mark.

College Me had accidentally done Future Me a solid.

I didn't have to survive another month.

And instead of falling into the 33% additional-refund tier, I had crossed the threshold for 67%.

All because of roughly $70 that had disappeared from some college paycheck years earlier.

I wanted control of the money.

I had already decided I didn't want to leave the pension where it was.

By then, I had spent years learning more about investing. I'd read about pension returns. I'd sat through conversations about the insurance-type investments associated with my retirement money.

And I kept thinking:

Why don't I just put this in Vanguard and buy index funds?

Nothing fancy.

Nothing exotic.

I wanted simple investments I understood and control over where my money was invested.

So when I left, I rolled roughly $115,000 into Vanguard.

That money became part of the portfolio I was slowly building toward financial independence.

And somewhere inside that six-figure rollover was the impact of one tiny, completely forgettable financial accident from years earlier.

About $70.

Ask one more question.

I'd love to tell you the lesson here is that 20-year-old me possessed extraordinary financial foresight.

She did not.

She apparently couldn't fill out her student employment paperwork correctly.

But there's another part of this story that wasn't an accident.

I called.

I asked questions.

I learned how the pension worked before I moved the money.

I understood that one month mattered.

And when I thought my only choices were stay in a terrible situation or leave money on the table, I kept asking until I understood what my actual options were.

That's something I've learned over and over with money:

You don't have to know everything.

But you need to know enough to ask another question.

Read the rules.

Call the person.

Check the old account.

Ask what counts.

Understand what happens before you move the money.

Sometimes the difference is enormous.

And sometimes it's hiding in $70 you accidentally invested in college.

Best $70 I ever spent.

Build the money. Build the life.

Plan for Paris.
Build for Tuesday.

When I picture retirement, I can picture Paris pretty easily.

Sitting at a sidewalk café. Drinking coffee. Wandering around with nowhere I need to be. Staying an extra week because I don't have to check how much PTO I have left.

I used to watch Emily in Paris, so obviously my retirement fantasy has excellent outfits and an unreasonable number of chocolate croissants.

I'm all for it.

Plan for Paris.

But retirement isn't going to be Paris every day.

Some days it's Cleveland, Ohio.

And honestly? That's kind of the point.

Retirement is full of boring Tuesdays.

We spend so much time preparing financially for retirement. How much do I need? What's my withdrawal strategy? When can I access my retirement accounts? How much should I have in cash? When can work become optional?

I've spent years thinking about those questions.

But once early retirement started feeling like something I might actually be able to do, another question started bothering me:

What am I actually going to do all day?

Not on the first day of retirement. Not during the trip to Paris. Not during the first glorious month when I don't have to open Outlook.

I'm talking about some random Tuesday three years later. No vacation. Nobody visiting. Nothing special happening.

What does that day look like? And will I like it?

The Boring Tuesday Test

Forget your retirement bucket list for a minute and picture a completely ordinary Tuesday.

What time do you wake up? Who are you having coffee with? How do you move your body? Do you have somewhere to go? Is there somebody you'd call just because? Is anyone expecting you somewhere? What are you learning? What are you looking forward to? Who are you having dinner with?

And what do you do at 2:00 in the afternoon when absolutely nobody needs anything from you?

That's the retirement day I'm interested in.

There are going to be an awful lot more Tuesdays than trips to Paris.

Who are your Tuesday people?

A good life isn't only about what you're doing. It's also about who you're doing the boring shit with.

Who are you walking with in your Hokas? Or, in my case, Vionics. I appreciate orthopedic support.

Who are you drinking your unnecessarily bougie coffee with? Who are you splitting a pint of Jeni's with? Who will watch Ted Lasso with you even though you've already seen it?

Who will wander around Costco with you eating free samples while you pretend you came only for the cheap gas?

Who are you going to the grocery store with? Who are you splitting half a cow with?

Yes. Apparently I've reached the stage of life where “Would I split a cow with this person?” is a legitimate measure of friendship.

We talk a lot about finding people to travel with, celebrate with and have adventures with. Those people matter.

But I also want people I can do absolutely nothing with. People I can text, “Going for a walk. Want to come?” People who make an ordinary dinner feel good. People I don't have to entertain.

Your Tuesday people.

A life that doesn't have to be extraordinary to feel good.

This may be what I'm really trying to build.

Not a life where every day is incredible. That sounds exhausting, actually.

Give me the cheap grocery-store flowers on the kitchen counter. A really good cup of coffee. A walk. A workout. Dinner with someone I love. A book I'm excited to read. Something I'm learning. Somewhere I belong. People I can laugh with.

Maybe nothing Instagram-worthy happens all day.

And I get into bed that night and think: That was a good day.

Not an extraordinary day. Not a productive day. Not a bucket-list day. A good one.

A life doesn't have to be extraordinary to feel good.

Start practicing retirement before you retire.

I don't want to work for years, build enough money to retire, shut my laptop one day and then ask: Okay. Now how do I build a life?

I want to start practicing that life now.

What do I already love doing that can come with me? What friendships do I want to deepen? What traditions could I start? Where do I want to belong? What hobbies do I want to try while I'm still terrible at them? How do I want to take care of my body? What gives me purpose outside of my job?

I think of these as retirement anchors.

Not obligations. I'm definitely not trying to escape a packed work calendar so I can create a color-coded 40-hour retirement calendar.

I want freedom. But I also want things that give my weeks rhythm.

Anchors, not obligations.

Work is doing more for us than we realize.

Work gives us a lot of things automatically: people, structure, problems to solve, places to be, casual conversations and a sense that we accomplished something.

Even if we can't wait to have more freedom, we're still going to lose some of that when work disappears.

Money can replace the paycheck. It can't automatically replace everything else.

That's why I'm building two portfolios: the financial portfolio that buys the freedom, and the life portfolio that gives the freedom shape.

Plan for Paris. Build for Tuesday.

I still want Paris.

I want the café. The chocolate croissant. The wandering. The adventures. The ridiculous stories I'll still be telling when I'm 80.

But I don't want to build a retirement that only feels good when something extraordinary is happening.

I want the coffee. The walks. The cheap flowers. The Costco runs. The dinners at home. The show we've already watched. The people I can call for absolutely no reason.

The boring Tuesdays.

Because maybe I've been thinking about ordinary life all wrong.

Doing boring shit with people you love is what makes life extraordinary.

So yes.

Plan for Paris. Build for Tuesday.

I Had Three $7,000 Problems

The first week of graduate school, I walked to my car crying.

We had spent the day on a gemba at a medical warehouse.

I understood approximately nothing.

They explained how the program worked. How we would be evaluated. How the grading worked.

And all I could think was:

What the fuck did I just sign up for?

I remember walking out that night thinking:

I failed today.

F.

Day one.

And, if I'm being completely transparent:

I didn't really like two members of my team either.

😂

One of my classmates saw me walking to my car.

“You can do this.”

I did not share his confidence.

This was going exceptionally well.

Get In. Do the Thing. Get the Fuck Out.

I hadn't ended up in graduate school accidentally.

Ten years earlier, in 2004, I had graduated from college with roughly $20,000 in student loan debt.

By 2014, I still had about $5,000–$6,000 left.

It wasn't crushing debt. But I was tired of looking at it.

And I knew one thing:

I wasn't taking out another student loan.

My employer offered a tuition benefit, which covered a significant portion of the program. The master's was an accelerated 13-month program, and after the benefit, my share was about $21,000.

Twenty-one thousand dollars sounded like a lot of money.

So I made it smaller.

The program had three major payment periods.

About $7,000 each.

Okay.

I didn't have a $21,000 problem.

I had three $7,000 problems.

That felt different.

The $50,000 Experiment

I have a habit of turning things into experiments. Usually it starts because I learn something, get curious and think: Why not try it?

First, there was a tiny house.

Early in my career, housing was one of my biggest expenses. So naturally, I decided I should learn something about real estate.

I got my real estate license. Not because I had some grand plan to become a real estate mogul. I just figured housing was probably going to be one of the biggest expenses of my life, so maybe I should understand how the whole thing worked.

I learned about equity. Appreciation. Mortgages. The economics of buying versus renting.

And I learned the old real estate advice: Buy the smallest house on the nicest street.

So I did. I bought a tiny house for about $94,000.

I owned it for roughly seven years. Eventually, I sold it and walked away with about $125,000 in proceeds.

More than I'd originally paid for the entire house.

That got my attention. So I invested the money.

Then I learned what money could do without me.

Somewhere along the way, I'd learned the basic rule of thumb that invested money could roughly double every seven years at certain long-term rates of return.

Obviously, that's not a guarantee. Markets don't politely double your money on a seven-year schedule.

But the concept fascinated me.

I looked at that roughly $125,000 and thought: That could theoretically become $250,000.

And I wouldn't have to earn the other $125,000. The money could do some of the work.

That was a pretty important realization for someone who had spent most of her life believing the way to make more money was to work more.

I'd been working since I was 15. I'd worked two jobs in college. I'd worked full time while going to graduate school full time.

I had gotten pretty good at doing the heavy lifting.

But what if I could eventually get the money to do more of it?

Why not $250,000?

I started wondering what would happen if I could deliberately get another $250,000 invested.

Not because $250,000 was some magical number. It just felt substantial enough to give compounding something meaningful to work with.

And I like simple math.

$250,000 divided by five years = $50,000 a year.

So I thought: Could I save $50,000 a year for five years?

I had no idea. But why not try?

This wasn't entirely new behavior for me. I'd bought a cheap little house because I learned something about real estate and thought, why not?

Years later, I went to graduate school while working full time and decided I wasn't taking out another student loan. I had about $21,000 of tuition to cover.

Three payments of roughly $7,000. Okay. Three $7,000 problems.

I figured it out.

And around the time I was dreaming up this latest experiment, I had done something considerably more dramatic.

I'd left a $133,000 CFO job for a $58,000 administrative fellowship.

I sold my house. I left the city. I moved to Charlottesville, Virginia—a place I had never even visited before accepting the job.

I figured I'd start over. New city. New job. New people. Maybe I'd meet someone and live happily ever after.

Four years later, I moved to Denver.

Apparently Charlottesville was basically college.

Not every experiment ends where you think it will.

So what counted as $50,000?

Once I decided to try this, I ran into a surprisingly annoying question. What exactly counted as saving $50,000?

403(b)? Roth IRA? HSA? Brokerage? Employer retirement contributions? Pre-tax? Post-tax?

I could have turned this into an incredibly complicated exercise. I didn't.

I wasn't trying to win the Personal Finance Olympics.

I wanted to get the big things mostly right. Use the retirement accounts available to me. Fund the Roth. Use the HSA. Put additional money into brokerage. Automate what I could. Then see how close I could get.

That was pretty much the system.

And still buy the damn coffee.

I have never been particularly interested in the version of financial independence where every $5 purchase needs to defend its existence.

I wasn't going to spend decades nickel-and-diming Current Me so Future Me could finally have a good time.

Actually, my coffee got bougier.

I now buy flash-frozen coffee that lives in my freezer and occasionally try to convince my friends that they need it too.

So no. I did not become a millionaire because I stopped buying coffee.

I wanted to get the big decisions right.

Earn more. Create a gap between what I earned and what I spent. Invest the gap. Give it time. Repeat.

And still buy the damn coffee.

It didn't go according to plan.

My actual spreadsheet is not a beautiful straight line.

One year, I had more than $60,000 going toward retirement and investments. Another year, the spreadsheet shows about $11,000.

But that $11,000 year wasn't some financial failure.

I was making $58,000. My rent alone was around $1,700–$1,800 a month. For comparison, the house I'd left had cost me somewhere around $800 a month all-in.

I was not living some glamorous high-savings-rate FIRE life. I was pretty much scraping by. And some of that $11,000 included employer retirement contributions.

But here's the important part: I had savings if I needed them.

I'd built financial security before I took the risk. And that meant I could tolerate a period when the monthly math wasn't particularly pretty.

I wasn't maximizing my savings rate. I was rebuilding my life.

The target served me.

This is probably the biggest thing I've learned looking back at the experiment.

I don't think the real goal was ever: Save exactly $50,000 every calendar year for five consecutive years.

Who cares?

The $50,000 was simply a target that helped me do something bigger: Get a meaningful amount of money working for Future Me.

Some years I could save more. Some years I couldn't. Sometimes money came from my paycheck. Sometimes I moved wealth I'd already accumulated—like the proceeds from selling a house—into investments. And sometimes I intentionally made a decision that caused my income to go down.

The spreadsheet wasn't the boss.

The target served me. I didn't serve the target.

Save for Future Me without nickel-and-diming Current Me.

Looking back, this may be the simplest description of my entire approach.

I wanted to do the financial heavy lifting while I had the income and ability to do it. I wanted money invested early enough that time and compounding could eventually help.

But I also wanted to live.

Travel. Eat good food. Buy ridiculous coffee. Try things. Change careers. Move somewhere I'd never visited. Start over if I needed to.

I didn't want to arrive at retirement with the largest possible portfolio and discover I'd spent decades waiting for my life to begin.

I was saving for Future Me without nickel-and-diming Current Me.

And maybe that's why the $50,000 experiment worked for me even when I didn't hit $50,000.

It wasn't really about the number. It was about building options. Building resilience. Building enough financial freedom that someday I wouldn't have to do all the heavy lifting myself.

And, occasionally, betting on myself just to see what happened.

Why not try?

That's pretty much how I got here.

Build the money. Build the life.

I Wasn't Trying to Retire in Five Years.
I Was Trying to Finish Saving for Retirement.

When I left to head to Virginia, I had roughly $115,000 from my pension that I rolled over and invested.

Then I sold my house and walked away with roughly $125,000.

So I had around $240,000 working for Future Me.

And I had a very simple plan.

$50,000 × 5

I thought: what if I could save another $250,000 over the next five years?

That's $50,000 a year.

If I could do that, I'd have roughly half a million dollars invested.

And in my head, that meant something very specific:

I could be done saving for retirement.

Not retire in five years.

Finish saving for retirement in five years.

Those are two very different things.

My Highly Sophisticated Retirement Math

Somewhere along the way, I'd learned the rough rule of thumb that invested money could double about every seven years at certain long-term rates of return.

Obviously, markets don't promise to double your money on schedule. It's a shortcut, not a guarantee.

But the idea fascinated me.

If $500,000 had decades to grow...

What if I didn't need to keep throwing huge amounts of new money at retirement forever?

What if I could do the heavy lifting early and then let time do more of the work?

That was the experiment.

It Was a Mentality

I wasn't trying to create the world's most precise financial plan.

I wanted a target.

I wanted a target to hit, not where to cut.

I didn't want to spend my life deciding whether I was allowed to buy coffee or whether I needed to live on rice and beans so Future Me could have the largest possible pile of money.

I wanted saving to be simple.

Maximize the pretax accounts. Put money in the brokerage account. Invest the house proceeds. Automate what I could.

Then live my life.

I work in finance. I know what a budget is.

And I also know something people sometimes forget:

Budgets are just forecasts.

Actuals don't always equal Budget.

Things change.

Life changes.

So the forecast changes.

The target gave me direction. It didn't get to run my life.

Then I Moved to Virginia

Which was convenient, because then I completely blew up the forecast.

I left a CFO job making around $133,000 and moved to Charlottesville for an administrative fellowship making around $58,000.

There was no universe where I was going to save $50,000 that year.

Okay.

New forecast.

I had just sold my house and invested the proceeds.

So I decided I'd save what I could and keep going.

I didn't decide the entire plan had failed because one year didn't match the spreadsheet.

That's the mentality I wanted.

Keep moving in the direction.

I Wasn't Trying to Retire Early

This is the funny part.

At the beginning, I wasn't trying to retire early.

I figured I'd save aggressively for five years, get retirement handled, and then move on to the next financial goal.

Maybe save for another house.

Maybe spend more.

Maybe just stop thinking about retirement so much.

Except I kept saving.

And the money kept growing.

And then work started changing the equation.

Then Work Changed the Equation

I like working.

I like solving problems. Building things. Improving systems. Learning something new.

What I don't like is sacrificing my health, time and sanity because somebody else can't manage a workplace.

And after enough difficult jobs and managers, I started seeing my investments differently.

They weren't just money for 65-year-old me.

They were options for right-now me.

Money meant I could leave.

Take a pay cut.

Move across the country.

Try something new.

Say no.

Start over.

The number wasn't just buying retirement anymore.

It was buying freedom.

What Was the Money Actually For?

That's the question that eventually led me here.

I spent years learning how to earn more, save more and invest more.

And I'm glad I did.

But I don't want money for the sake of having money.

I want my time back.

I want ordinary mornings walking my dog.

I want hobbies I'm terrible at.

I want people I love.

I want coffee and books and dinners and ridiculous little adventures.

I want to walk my nephew to school.

I want to do boring shit with people I love.

That original five-year experiment was supposed to help me finish saving for retirement.

Instead, it helped me understand what I was really saving for.

I wasn't just funding retirement.

I was buying back my future Tuesdays.

Build the money. Build the life.

I Left a $133,000 CFO Job for a $58,000 Fellowship

On paper, I was doing pretty well. I was a CFO. I was making about $133,000 a year. I owned a house. This was supposed to be success. Except I wasn't sleeping.

The job was eating me alive.

I joined a nursing school during COVID.

About two months in, I realized something in the financials didn't make sense. The accounts receivable balance was way too high. Based on the number of students we had and what an individual student could reasonably owe, the math simply didn't work.

So I started digging. And digging. And digging.

At first, I hoped whatever was wrong might be $100,000. It took months to unravel. By around month nine, the problem we'd identified was roughly $7.2 million.

Not exactly what I had envisioned for my exciting new CFO job.

The finance person who had handled much of this work for years had abruptly left. There were boxes. Records. Years of history I hadn't been there for.

I was trying to reconstruct what had happened while simultaneously becoming the person responsible for explaining it.

At one point, I remember thinking: If I drive past her house and there's a yacht in the backyard, at least I'll finally know where all the money went.

To be clear, I did not uncover a yacht. I uncovered a giant financial mess.

Honestly, the yacht might have been easier.

Meanwhile, everything else was falling apart.

This was COVID. Enrollment was struggling. The school was losing money. We were cutting expenses everywhere.

I genuinely worried the school might close.

At one point, the coffee shop was losing money, so the obvious financial answer was: Close the coffee shop.

Except our building had 24/7 security because of the area we were in. We didn't have vending machines.

So I remember thinking: Okay...where exactly are the nursing students and employees supposed to get coffee? Or food?

This was apparently my life as CFO.

I wasn't optimizing some thriving organization. I was trying to keep things functioning while delivering one piece of bad financial news after another.

And because I was the CFO, I got to deliver it. To leadership. To the board. Over and over.

I thought I was going to get fired for doing my job.

That may have been the hardest part.

I was already carrying the stress of finding a massive financial problem almost immediately after arriving. At the same time, I was dealing with hospital-system leadership that made it very clear I wasn't particularly wanted.

I was humiliated on finance calls. My job felt threatened.

I once sat in my office listening to a senior finance leader in the office next door criticize the college, apparently unaware that I could hear the conversation.

I stopped sleeping.

Every day felt like I might get fired for doing the very job I'd been hired to do.

And then I turned 40.

Happy 40th birthday to me.

For my 40th birthday, I went to Nashville. I was on PTO.

Unfortunately, my birthday happened around month-end close. I was told I needed to join the finance call.

Fine.

I figured I'd log in, cover whatever was needed from the nursing school and get back to my birthday.

Nope.

I sat in my hotel room for the entire two-hour call.

Everyone else got to experience Nashville. I got month-end close.

Happy 40th birthday to me.

Looking back, there's something almost comical about it.

I had spent years climbing. I had the title. I had the salary. I had the house.

And on my 40th birthday, I was sitting in a Nashville hotel room on PTO, trapped on a finance call I didn't need to be on for two hours.

I knew it was time to go.

I didn't want to just run away.

I started applying for jobs. A lot of jobs. I interviewed.

I knew I needed to leave, but I didn't want to grab the first available escape hatch simply because I was miserable.

I wanted to move toward something, not just run from something.

Then my former university boss called me. She had been a reference for a job I'd just interviewed for.

I told her I didn't need it. That job didn't feel right.

Then she told me something completely different.

The current administrative fellow at her health system had dropped out, leaving a one-year opening. Would I want to fill it?

I didn't even really know what an administrative fellowship was.

And somewhere in my exhausted brain, I thought: Why the fuck not? Who cares?

There was no sophisticated career strategy. There was no five-year plan. I had absolutely no idea where a one-year fellowship would lead.

I just knew where I was wasn't working anymore.

So I said yes.

There was one small detail.

The fellowship paid about $58,000. I was making about $133,000.

That's a $75,000 pay cut.

CFO → Fellow

$133,000 → $58,000

Homeowner → Renter

Established life → I have absolutely no idea what I'm doing

And weirdly, I did it anyway.

Apparently Nashville and I had unfinished business.

Before the fellowship opportunity came up, I'd already agreed to another job interview. In Nashville.

So about a month later, even though I'd accepted the fellowship, I went to the interview I'd already committed to.

I didn't get the job.

But this time I actually got to experience Nashville instead of sitting in my hotel room on a finance call.

So I'm calling it a win.

Then I sold the house.

This is one of those decisions I could make sound very smart in hindsight.

It wasn't.

Everyone told me: Rent the house.

And I went back and forth. Maybe I should rent it. Maybe I should sell it. Maybe I'd hate Virginia. Maybe I'd come back. Maybe I'd never come back.

Who knew?

Even now, there are days when I think: I should have never sold that house.

Maybe financially, keeping it would have been the better decision. I'll never know.

But at the time, I was leaving. I didn't know where my life was going next, and I decided to sell.

That decision would eventually become connected to another experiment in my life—investing the proceeds, thinking about compounding and asking what would happen if I could deliberately get more money working for Future Me.

But I didn't know any of that yet.

At the time, I was mostly thinking: What the fuck did I just do?

I had never even been to Charlottesville.

This part gets better.

I accepted a job in Charlottesville, Virginia without ever having visited Charlottesville.

Then I rented an apartment there. Sight unseen.

Finding one wasn't particularly easy because I also had a big pit mix coming with me, and not every apartment wanted my crazy dog.

Eventually, I found a tiny two-bedroom, two-bath apartment that would take us.

Perfect.

Except then the move became a complete shit show.

My stuff wasn't arriving when it was supposed to. I stayed in Columbus longer than planned. Plans changed.

At one point, I was basically trying to beat my own belongings to Virginia so I could meet the movers that morning.

And because apparently major life transitions in my world require additional complications, there was also a crack in my car's AC condenser.

Of course there was.

So there I was.

I'd left a $133,000 CFO job. Sold my house. Taken a $58,000 fellowship. Rented an apartment I'd never seen. In a city I'd never visited. With a crazy dog. While trying to beat a moving truck to Virginia.

This was going great.

Eventually, my stuff showed up.

The movers deposited my former life into my tiny apartment.

A friend from Columbus had moved to Richmond and drove over to help me unpack and throw things away.

And eventually, there I was. In Virginia. A fellow. Not a CFO. Making $58,000. Surrounded by boxes. Still trying to shake off everything I'd just been through.

And wondering, more than once: What the fuck did I do?

That's the part we leave out of “bet on yourself.”

We usually tell these stories backward.

Once we know how everything turned out, we make our old decisions sound much more confident than they actually were.

We say: I took a leap. I chose myself. I bet on myself.

And I did.

But betting on myself did not mean I knew I'd made the right decision.

I questioned it constantly.

I didn't know what job I'd have after the fellowship. I didn't know where I'd live. I didn't know whether selling my house was smart. I didn't know whether cutting my salary by $75,000 was going to look completely insane a year later.

I didn't know whether any of this would work.

What I knew was that staying wasn't working anymore.

And somewhere underneath all the fear and second-guessing was something else I'd learned about myself:

I'd rebuilt before.

If this didn't work, I'd figure out something else.

Sometimes you bet on yourself.

Not because you know you're going to win. Not because everything is going to work out exactly as planned.

And definitely not because the movers will arrive on time and your air conditioning will work.

Sometimes you bet on yourself because certainty isn't coming.

You make the best decision you can with the information you have. Then you deal with what happens next.

Maybe you sell the house you should have kept. Maybe you take the job that leads somewhere completely unexpected. Maybe the plan changes. Maybe you change.

You figure out the next thing. Then the next thing. Then the next thing.

I didn't know it at the time, but leaving that CFO job would change the direction of my career, my finances and eventually my life.

But that's not why I did it.

I did it because I knew I couldn't keep living the life I had built just because it looked successful on paper.

I was 40. I had the title. I had the salary. I had the house.

And I was miserable.

So I blew some of it up.

Why the fuck not?

Sometimes you just bet on yourself.

Build the money. Build the life.

1% Better

Direction, not perfection.

I have apparently been telling myself to get 1% better every day for years.

I know this because I found the receipts.

They're everywhere in my old notebooks.

Written next to investment balances. Job applications. Workouts. Guitar practice. Food. Houses. Moving. Bad days. Really bad Mondays.

And approximately seventeen different plans for my life.

Apparently Past Me really liked arrows.

Get job → buy house → move → save → invest → buy another house → retire.

Easy.

😂

Except life doesn't move in a straight line just because you drew an arrow.

Direction, Not Perfection

For a long time, I think I treated 1% better like another goal.

Do the workout. Eat perfectly. Save more. Make more. Get promoted. Read the book. Fix the problem. Optimize the spreadsheet. Keep going.

And if I wasn't moving forward fast enough?

I was really good at beating myself up about that too.

I'm a recovering perfectionist.

I used to think getting better meant doing everything right.

Now I think it means moving in the right direction.

Sometimes 1% better is adding another $100 to an investment account.

Sometimes it's swinging the kettlebell.

Sometimes it's starting the workout when you really don't feel like doing the workout.

Sometimes it's going back to archery even though you're still very much a beginner.

Sometimes it's writing something and hitting publish before you've edited the personality out of it.

Sometimes it's calling someone you love.

Sometimes it's resting.

Sometimes it's having more fun.

Sometimes it's trying a new Jeni's flavor because life cannot possibly be entirely about retirement accounts and protein.

Sometimes Better Means Stopping

And sometimes 1% better happens at work.

Maybe we fix the process.

Maybe we delete the god-awful VLOOKUP formula that nobody understands.

Maybe we don't even know how to fix the problem yet.

We just finally look at each other and say:

Houston, we have a problem.

That counts too.

Because identifying the problem is movement.

And then sometimes?

We stop at 4:00.

The problem will still be there tomorrow.

We work at a university, after all.

Nobody needs us performing emergency spreadsheet surgery at 7:30 p.m.

That might actually be the biggest change for me.

I spent a lot of my life believing that better required more.

More work. More discipline. More money. More achievement. More optimization.

Now I'm starting to think better sometimes means enough.

Enough work for today.

Enough money to create choices.

Enough exercise to make my body stronger.

Enough planning to know the direction.

And enough space left in my life for the people and things I actually want all of this for.

I'm still ambitious.

I'm still going to save and invest.

I'm still going to swing the heavier kettlebell.

I'm still probably going to make a spreadsheet.

Obviously.

But I'm not trying to build a perfect life anymore.

I'm trying to build one that's moving in the right direction.

1% better.
Not perfect.
Just forward.

And preferably together.

Because doing it with people you love makes the whole damn thing worth it.

The Million Dollars Wasn't the Goal

On January 11, 2026, I wrote this in my journal:

IT HAS HAPPENED.
$1 MILLION NET WORTH.

Underlined.

Boxed.

Very dramatic.

I had been working toward this for more than 20 years.

I started my first real job in 2004 making $33,000.

I couldn't even invest in the retirement plan my first year.

Eventually, I started saving.

Then investing.

Then saving more.

At one point, I decided I was going to save $50,000 a year.

Why?

Because I had a goal:

$1 million.

And somehow, after years of jobs, raises, a master's degree, moving, houses, a massive pay cut, more jobs and a truly unreasonable number of Vanguard transactions...

I DID IT.

One. Million. Dollars.

Surely I stopped to appreciate this enormous accomplishment.

Maybe opened champagne?

Called someone?

Bought myself something ridiculous?

Took the rest of the day off?

No.

Do you know what I wrote DIRECTLY UNDERNEATH IT?

Next 5 years → assets.

😂

FOR FUCK'S SAKE, LIBBY.

Can we enjoy anything?

Apparently not.

Congratulations. Here Is Your Next Assignment.

This is apparently how my brain works.

Hit goal.

✓

Great.

NEXT.

Get the degree.

✓

Get the promotion.

✓

Save $50K.

✓

Hit $1M.

✓

Excellent work, everyone.

Now let's buy some houses.

😂

I had spent twenty years climbing this giant financial mountain, got to the top, looked around for approximately six seconds and apparently thought:

Cute. Where's the next mountain?

And there's nothing wrong with another goal.

I love goals.

I love plans.

I love spreadsheets.

I especially love a spreadsheet where I can change one assumption and convince myself I can retire six months earlier.

This is recreation for me.

But going through my old journals made me notice something.

There were two completely different plans happening on the same pages.

There was the money plan:

Save. Invest. Hit $1M. Buy assets. Retire.

And then there was this other random pile of stuff:

Learn guitar. Try archery. Play golf. Get stronger. Read. Travel. See friends. Move closer to family. Walk the dog. Find someone to do life with. Eat good food. Have fun.

Basically:

Money Plan: extremely organized.

Life Plan: vibes.

😂

Okay, But Then What?

Here's the problem.

Eventually the spreadsheet is going to say I can retire.

And I fully intend to believe the spreadsheet because I probably made it.

But then what?

Monday will be amazing.

No alarm. No meetings. No email. No one asking me why a number doesn't tie.

I'M FREE.

Tuesday?

Still pretty exciting.

Maybe Costco.

But eventually it's going to be some random Tuesday in February.

And that's the day I'm interested in.

What am I doing?

Who am I with?

What gets me out of bed?

What am I learning?

Who am I helping?

Who am I texting:

Costco?

Because I absolutely refuse to spend decades building financial independence only to arrive there and think:

Well, shit. Now what?

Apparently I Was Building Two Things

I thought I was building wealth.

And I was.

But those notebooks make it pretty obvious I was also trying to build a life.

I just didn't realize those were supposed to be the same project.

That's what has changed for me.

I'm still saving.

I'm still investing.

I'm still going to make spreadsheets.

Obviously.

We're not throwing away civilization.

But I'm also building the other side now.

Call your friend.

Walk the dog.

Swing the kettlebell.

Go to archery.

Try the thing you're terrible at.

Write something.

Go somewhere new.

Eat the Jeni's.

Have the boring Tuesday.

And for God's sake, when you accomplish something you've worked toward for twenty years:

Maybe take twelve minutes before creating the next five-year plan.

I'm working on that one.

1% better.

Because the million dollars wasn't actually the goal.

The life was.