You Don't Have to Optimize Everything

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🎧 Audio Version Available

Prefer to listen? I recorded an audio version of this piece. There’s also a short reflection at the end.

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I have a small but annoying problem when it comes to writing emails at work.

I tend to overthink them. A lot.

What should be a quick note often turns into several minutes of drafting, revising, and reconsidering. Is the tone right? Could this sentence be misinterpreted? Is that word precise enough, or will it create confusion?

At one point it became almost compulsive. Even the simplest messages required multiple passes before I felt comfortable hitting send.

Eventually I realized something: more tinkering wasn’t getting me closer to a perfect email. It was just consuming time and attention.

So I tried an experiment. I wrote the message once, gave it a quick glance, and sent it.

Guess what? No one cared.

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Once I noticed it with email, I started seeing the same pattern everywhere else.

It got me wondering about how we think about work and careers.

We spend an enormous amount of energy trying to optimize everything. The perfect job. The perfect title. The perfect sequence of moves that will position us for whatever comes next. We analyze opportunities from every possible angle, worrying about how each decision might affect our trajectory five or ten years down the road.

Should I take this role or wait for something better?

Will this company look good on my resume?

Does this title signal progress, or will it look like a lateral move?

If I stay here another year, will I miss a bigger opportunity somewhere else?

At some point it starts to resemble the email problem.

We keep rewriting the message in our heads, convinced that if we just think a little harder, analyze a little longer, we’ll arrive at the perfectly optimized choice.

But most of the time, the world doesn’t work that way.

Careers aren’t precision machines where every move determines the final outcome. They’re far messier than that. Timing matters. Other people’s decisions matter. Entire industries shift. Companies rise and fall. Roles evolve in ways no one could have predicted when you first accepted them.

In other words, the difference between the “perfect” decision and the merely good one is often far smaller than we imagine.

And the cost of trying to optimize everything can be surprisingly high.

You end up carrying a constant low-grade tension. Every decision feels like it has enormous stakes. Every opportunity has to be evaluated not just for what it is, but for what it might signal, unlock, or prevent somewhere down the road.

It’s exhausting.

At some point, you realize something similar to what I discovered with email: more analysis isn’t necessarily getting you closer to a perfect answer. It’s just consuming time and mental energy.

Sometimes a good decision is… good enough.

You take the role that seems interesting right now. You work with people you respect. You try to do the job well. And then you see what happens next.

Most careers, when you look back at them years later, don’t resemble carefully optimized plans. They look more like a series of reasonable decisions made under uncertainty.

A job that seemed like a small step turns out to open unexpected doors.

A role you thought would be temporary becomes surprisingly meaningful.

An opportunity you almost didn’t take ends up shaping the next decade of your life.

None of that was optimized in advance.

It was discovered along the way.

That doesn’t mean decisions don’t matter. Of course they do. Thoughtfulness is valuable. Planning has its place.

But there’s a difference between being thoughtful and trying to optimize every variable.

Life rarely reveals the “best” path in advance. Most of the time we’re making reasonable decisions with incomplete information, then discovering what they meant only later. The story of a career tends to make sense in hindsight, but almost never while you’re in the middle of it.

Which means the pressure we put on ourselves to perfectly engineer the future is often misplaced.

Sometimes it’s enough to choose the option that seems interesting right now. Work with people you respect. Do the job well. Stay curious about what might come next.

Then let the rest unfold.

Sometimes it’s enough to write the email, give it a quick glance, and hit send.

Careers, it turns out, work a lot the same way.

-Scott