What Are We Optimizing For?

A question I couldn’t shake after EconoMe.

Something felt off at EconoMe this year, and I haven’t been able to stop thinking about it.

If you’re not familiar, EconoMe is one of the largest gatherings of people pursuing financial independence. About five hundred of us descend on a college campus, talk money and life all day, and then stay up way too late in the hotel lobby drinking hard seltzer and eating popcorn and gummy worms.

It’s a special community. The people in it changed my life.

I’ve been pursuing FI since 2015. I’ve made the spreadsheets, devoured Your Money or Your Life and The Simple Path to Wealth, and attended many in-person events. In 2023, after going to my first CampFI, I took a three-month sabbatical. I went back to work for six months, then left again to take a full gap year. Those decisions came directly from what I jokingly refer to as the “bad influence” (and support) of this community.

So this isn’t an outsider critique. This is me, from the inside, asking a question I can’t seem to shake:

What are we optimizing for?

Last year at CampFI Mid-Atlantic, a friend of mine gave a talk about building friendships in the FI community. One of her slides said, “You are my people.” That sentiment struck a chord with me because I had come to that same realization myself.

At my first CampFI, it felt like I was finally surrounded by people who saw the world the way I did. People who wore the same rose-tinted glasses. People who understood that the default path isn’t the only path, and that you don’t have to work until 65 and hope you have enough time and health left to enjoy life.

That weekend, I walked around sharing my numbers and asking near-perfect strangers, “Do you think I have enough saved to take a month off?” And people kept saying, “Of course you do. Take three months. Take a year.” I was like… what? Who are these people?

That was the energy. That was the magic. People encouraging each other to go for it, to be bold, to take action.

This year at EconoMe, the vibe felt different.

I went to a breakout session on Coast FI led by Jess and Corey from The Fioneers. I was excited. I thought, this is where my people will be. The ones who are actually using this money to design their lives right now.

They walked us through a case study about a guy they called Roger. Early 30s. About $400k invested. A 43% savings rate. On track to overshoot his FI number by a wide margin if he stayed the course. But Roger was feeling burnt out and wanted to take time away from work to recover, maybe travel a little.

The question was simple: Is Roger in a good financial position to take a gap year?

People reluctantly agreed that yes, he was. The numbers and projections seemed strong enough. But it wasn’t an enthusiastic yes. It was cautious. Qualified. Full of hesitation.

Then they asked a second question: If you were Roger, would you take the gap year?

We did a show of hands. And I just sat there, stunned.

Because most people wouldn’t do it.

Even with the math clearly working in his favor. Even with a massive margin of safety. Even in a room full of people who chose to attend a talk about Coast FI, they still couldn’t give themselves permission.

I remember thinking, what is going on here?

Who are these people?

Did we read a different playbook?

You’ve done the work. You’ve built the wealth. And you still don’t feel allowed to use it?

At the end, the presenters revealed that “Roger” was actually Steve, and he was sitting among us in the audience. He did take the gap year. It turned into three years. And he was about to return to work in the same industry.

He was fine. More than fine.

But that wasn’t the moment that stayed with me the most.

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The next day, eleven of us gathered for lunch to remember our friend Sean. We sat around a long table at the Elephant Walk Indian Bar and Grill, a little awkward at first, and then very quickly not.

Some people had known Sean for over a decade. Others had only met him briefly at recent FI gatherings. But as we went around sharing stories, a few themes kept coming up. He was warm. Funny. Fully himself.

We talked about how he had inspired us, listened to us, showed up so fully for his people and his pup. We promised to carry on his spirit of adventure in our own lives.

I met Sean in 2024 at CampFI Mid-Atlantic after I gave a talk about my sabbatical. While most people wanted to talk about logistics, how I negotiated my leave of absence or rented out my house, Sean walked up and said, “Let’s talk bags.”

I knew immediately that he was my kind of people.

I know attending his first CampFI was what finally gave Sean the confidence to retire early. He went in May. By July, he had left his job and was traveling full time.

That’s the kind of community I believe we can be. One that supports each other in making bold moves, not just safe ones.

Sean and I became fast friends, a quiet support system for each other while we were both solo traveling. We commiserated over faulty eSIMs and bouts of loneliness, the challenge of making new friends on the road, and the strange in-between feeling of building a life that doesn’t follow the script.

One night I encouraged him to get out of his shell and go out and meet new people. He replied, “I don’t like humans.”

A few hours later: “Okay, I took your advice and talked to humans and had a much better night.”

That was him. Honest. Self-aware. Willing to try.

He once said to me, “I only wish I’d done this sooner.”

In my eyes, Sean had done everything right. He saved. He invested. He hit his FI number. And with the support of this community, he reached the point where he felt ready to live differently.

And he did. Boldly and unapologetically.

And then he died.

Less than two years after he retired early. He was only 48.

So I keep coming back to this question:

What are we optimizing for?

Because from where I’m sitting, it feels like a lot of people in this community are optimizing for certainty. For the safest possible version of an already safe plan. For a number that was meant to give them freedom, but has somehow become the thing keeping them stuck.

I think a lot of people are afraid to trust the process. Afraid to trust themselves.

And I get it. There is comfort in spreadsheets. In projections. In knowing that if you stay the course, everything should work out.

But life does not offer that kind of certainty.

People die young. Parents get scammed. You can do everything right and things will still not go as planned.

At the conference, I kept hearing people joke about suffering from ‘One More Year Syndrome.’ Going to the same breakout session year after year, knowing they could stop working, and still not doing it.

It’s worn like a badge of honor. Like it’s just part of the process.

But at some point, it stops being funny.

This community is white knuckling their net worth projections, so focused on reaching a point of complete certainty that they will not run out of money.

I think we should be more afraid of running out of time.

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This community taught me to think differently about money. It also taught me, at least at one point, to think differently about how I live. To ask bolder questions. To take the trip. To take the break. To stop waiting for permission.

If something unexpected were to happen to you this year, and your FI friends gathered to remember you next March, what would they say?

That you were careful? Disciplined? Always just ‘one more year’ away?

Or, that you lived life on your own terms. Boldly. Unapologetically.

So I’m asking now:

If financial independence is supposed to give us freedom, why are so many of us afraid to use it?

Because the math is not the hard part.

Believing you’re allowed to use the freedom is.

And if you’ve been asking yourself some version of this question too… you might be my people.

And Sean, if you can read this, I still think the Osprey 40L with a separate 24L day pack is the way to go.