Bonuses hit. Jobs change. People move. Life accelerates. Most people are expected to figure it out alone.

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We did it fam! Finally had (by my definition) a true viral LinkedIn post.

And of course it wasn’t some thoughtful, highly intentional, motivating message about Habits or the value of financial advisors…

It was me, battling the flu over the holidays, and pissed off at all the “watch my 5am-9am routine” influencer garbage. Don’t get me wrong, I’m a big believer in routines and starting your mornings on the right foot, but the content online is insane these days.

There’s a moment I’ve seen over and over again where nothing is technically wrong, but everything feels off.

The job is solid. The income is predictable. The savings are moving in the right direction. From the outside, it looks like momentum. From the inside, it feels like you’re watching the same episode on repeat. Same meetings. Same paycheck cycle. Same plan you once worked really hard to build.

And then someone wakes up one morning and decides they’re done.

They quit a job they used to defend at dinner parties. They move cities with no real plan. They torch a relationship. They buy something wildly expensive or make a financial decision that makes zero sense relative to their values. Everyone around them is shocked. They call it impulsive. Reckless. A crisis.

But it almost never is.

Most of the time, it’s boredom that’s been quietly compounding for years.

Consistency keeps life stable, but boredom is often what pushes people to blow it up.

Early in our careers, consistency feels like winning.

A steady paycheck is relief. Automatic savings feels responsible. Watching debt disappear feels powerful. You’re building habits. You’re doing the right things. For a long time, more money genuinely improves your life. It buys flexibility. It reduces anxiety. It opens doors that used to feel permanently closed.

I don’t think people are wrong for chasing that. I chased it too.

But something changes once consistency stops being something you earn and starts being something you expect. Once your income, lifestyle, and trajectory feel locked in, the emotional reward disappears faster than the spreadsheet suggests it should.

Certainty is comforting until it becomes invisible. When you know exactly how next month looks, your brain starts craving friction. Not because you’re ungrateful. Because humans aren’t built to feel fulfilled by predictability alone.

This is where money decisions start getting weird.

People don’t usually make bad financial choices because they forgot the math. They make them because the math stopped giving them meaning. Predictable money starts getting used to create novelty instead of stability. Risk feels exciting again. Spending feels like agency. Big swings feel like proof you’re still alive.

From the outside, it looks irrational. From the inside, it feels like relief.

When money becomes boring, people start using it to manufacture feeling instead of alignment.

You see this most clearly in people who optimize too hard for the future.

I’ve spent a lot of time around folks deep in FIRE. The discipline is impressive. The tradeoffs are intentional. The logic is sound. But I’ve also seen the version nobody puts on Twitter.

Years of declining invitations. Skipping weddings. Passing on trips. Saying no to small joys because they don’t fit the plan. Life narrowed down to efficiency. Everything deferred to a later version of themselves who will finally have time.

And then that version arrives.

They’re financially independent. No boss. No calendar pressure. No real constraints. And suddenly the question they avoided for decades shows up uninvited. What do I actually like doing? Who am I when I’m not optimizing?

If you delay hobbies, friendships, curiosity, and identity long enough, money doesn’t fix that gap. It exposes it. You’re not free. You’re disoriented. Now the impulse isn’t to save more. It’s to scramble for meaning. To spend reactively. To chase intensity. To retroactively build a life that was put on pause.

This isn’t a knock on FIRE. It’s a reminder that consistency without texture doesn’t age well.

If you postpone living until the spreadsheet gives permission, don’t be surprised when freedom feels unfamiliar.

This is the paradox I keep circling back to.

We chase certainty because it feels like safety. We chase consistency because it feels like control. But once we have them, we often feel an urge to disrupt them. Not because we failed. Because the plan didn’t account for boredom.

Money is a tool. It was never meant to be the point. Early on, more of it solves real problems. Later on, the role changes. It becomes less about accumulation and more about alignment. But a lot of people never update the goal. They just keep repeating the same behaviors and wonder why they feel restless.

I see this with founders who sell a company and immediately feel untethered. Advisors who hit a comfortable book size and start questioning everything. Clients who “have enough” but can’t stop scanning for what’s next. I see it in myself too.

The mistake isn’t wanting stability. It’s pretending stability alone is enough.

Most overnight decisions aren’t actually overnight. They’re the result of ignoring small signals for a long time. Boredom. Restlessness. A sense that life has become overly optimized and under-lived. When those signals go unaddressed, they don’t disappear. They wait. And then they show up as something louder.

There’s no clean fix here. No tidy framework. Just a recognition that consistency is a tool, not a destination. And that certainty without intention turns into something brittle.

Money works best when it supports a life you’re actively engaged in, not one you’re endlessly preparing for.

The goal isn’t to eliminate consistency, it’s to make sure it doesn’t quietly push you toward decisions you’ll later pretend were spontaneous.

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