Opening Scene
I was four years into a career in acupuncture when I realized I hadn’t enjoyed a single Tuesday in about eight months.
Not the Mondays -- Mondays are supposed to be hard. Not the big events, the conferences, the moments where you’re ON and everything clicks. Those were still good. I’m talking about the regular day. The 2 PM appointment. The drive home. The feeling of the thing when nobody’s watching.
I had all the evidence that it was working. Revenue was up. Clients liked me. I was good at it. I’d spent years getting certified, building a practice, becoming the person who does this thing. And if you’d asked me “is it going well?” I would have said yes, because I was averaging in the highlights.
But the typical day had already turned.
I didn’t leave for another year.
What I Thought Was True
I thought momentum was proof. If something is still moving, it’s still working. The trend is your friend -- in careers, in relationships, in habits, in the stories you tell yourself about who you are.
And there’s something to that. Consistency matters. Showing up matters. You don’t quit the thing just because Tuesday was hard.
But I had this assumption underneath all of it that I never examined out loud: that the longer something had been going, the more evidence I had that it was right. Like duration was validation. Like the fact that I’d been doing it for four years meant I should do it for a fifth.
That’s backwards, it turns out. Or at least, it’s backwards past a certain point.
Here’s the thing about assumptions. You don’t know you have them until something slaps you. And even then, your brain goes looking for the counter-argument because it’s more comfortable to be uncertain than to be wrong. That’s not a career thing. That’s just how humans work.
What I Discovered
I’ve been running data analysis on some stuff recently -- different context, doesn’t matter -- and I found a pattern that I can’t stop thinking about.
When you measure the average outcome of something, it can look great. Positive, healthy, fine. But the average is lying to you, because a few incredible moments are pulling the number up while most of the regular moments have already gone negative.
The average Tuesday looks fine if you had one amazing Tuesday, even if the rest of them sucked.
There’s a different number that tells you the truth. Not the average -- the typical. What does the MIDDLE outcome look like? Not the best, not the worst. The one you’d get if you just showed up on a random day and measured.
And what I found -- across a huge dataset, hundreds of thousands of observations -- is that there’s a point where the average still looks great but the typical outcome has already turned negative. The highlight reel is carrying the whole story while the day-to-day has quietly deteriorated.
The gap between the average and the typical is where people get stuck.
You stay in the job because the average includes that one project last quarter that reminded you why you started.
You stay in the relationship because the average includes the vacation where everything felt right.
You stay in the habit because the average includes the one week where it actually worked.
But the typical Tuesday? You already know what that feels like.
The Framework
So here’s what I kept thinking about, because my brain does this thing where it won’t stay in one lane.
(IT’S CALLED ADHD!!!)
I kept thinking about smoking.
I smoked for years. And the thing about quitting smoking isn’t the physical part. That’s over in a week. The thing about quitting smoking is that you have to stop being a smoker. That’s an identity shift. And identity shifts are the hardest thing a person can do, because your brain has built an entire operating system around who you think you are.
I was a smoker. Then I was a person who doesn’t smoke. Same body. Different operating system.
I was an acupuncturist. Then I was a keynote speaker. Same person. Different operating system.
The reason we don’t leave -- the real reason, underneath the practical stuff -- is that leaving means admitting that the version of yourself you’ve been running is due for an update. And that feels like failure even when it’s actually growth.
I don’t know who first said “sunk cost fallacy” in a way that actually changed behavior, because knowing the name of the thing doesn’t make it easier to act. Understanding it intellectually doesn’t make your nervous system feel it. You can read about sunk costs and still stay in the thing for another eighteen months.
But here’s what I’ve noticed. Three signals. If two of three are showing up, it’s time to at least check the exit.
One: The highlights are carrying the story. You’re averaging in the best moments -- the one great week, the one amazing conversation, the one time it all clicked -- and those are masking what the typical day looks like now. The highlight reel is doing all the work.
Two: You’re in rare air. Almost nobody sustains what you’re sustaining. That doesn’t make you special -- it makes you an outlier, and outliers don’t have trend lines. When you’re doing something that almost nobody does for this long, at this intensity, with this level of diminishing returns, you’re not in a trend anymore. You’re in an extreme.
Three: You need it more than you’re evaluating it. This one’s the killer. You’re not staying because it’s good. You’re staying because leaving feels like admitting something. You’ve stopped asking “is this working?” and started defending why it should be working.
That third one is the one that gets people.
Check-ins
Head Check: Where in your life right now is the highlight reel doing all the work? Not the best version -- the typical Tuesday. What does that feel like?
Heart Check: Is there something you’re holding onto because it was good, and you’re having trouble separating what it WAS from what it IS?
Gut Check: If you couldn’t tell anyone why you stayed -- no explanation, no justification, no story -- would you still stay?
I want to be careful here because this framework can be used badly.
“It’s time to leave” is not a permission slip to quit everything uncomfortable. Discomfort is not deterioration. Difficulty is not the same as decline. You know? Some of the best things in my life looked terrible in the middle. Marriage. Comedy. Building a business. The middle is supposed to be hard.
The difference is whether the middle is hard because you’re growing or hard because you’ve stopped growing and you’re just... maintaining a version of yourself that’s already peaked.
I think about this with dog training, weirdly. (Everything connects for me, I can’t help it.) When you’re training a dog, there’s a phase where the dog knows the command but chooses not to do it. That looks like regression. It’s actually progress -- the dog is testing the boundary, which means the dog understands there IS a boundary. The difficult middle is part of the process.
But there’s a different phase where the dog has learned the command, performs it reliably, and you’re still running the same drill. That’s not training anymore. That’s habit. And habit without purpose is just repetition wearing a costume.
I told you about the acupuncture thing. Here’s the part I usually leave out.
I knew at month four. Not month eighteen. Month four. Something felt off. The typical hour with a patient had a quality to it that I couldn’t name but could feel -- a flatness that wasn’t exhaustion and wasn’t boredom, exactly. More like I was doing a good impression of someone who loved this.
And I was GOOD at it. Four treatments and no more neck pain for 9 months. I’m still blown away by that.
That’s what made it hard. Being good at something you don’t love is one of the most effective traps there is, because everyone around you is confirming that you’re in the right place. The external feedback says stay.
PLUS YOU SPENT 4 YEARS AND 6 FIGURES ON THIS DEGREE!
The internal signal says something else.
It took me years to trust the internal signal. And honestly? I’m still working on that.
The insurance gig was the same way. I was selling, I was successful, the numbers were right. And the typical Tuesday felt like wearing a suit that fit perfectly but belonged to someone else.
Incidentally, I can always look back and see when I was betraying myself, because I was wearing clothes that weren’t me. I was trying to be someone else. And I looked really, really stupid.
Now here’s the part I don’t totally know the answer to.
There’s a version of this where the “check your exits” idea is a decision-making tool, and there’s a version where it’s a life philosophy, and I’m not sure they’re the same thing.
In some contexts you can define the exit cleanly. The data is clear. The typical outcome has turned. You go.
In life it’s messier. The metrics are fuzzier. You don’t have hundreds of thousands of observations of your marriage or your career to run statistics on.
What you have is the feeling of a Tuesday.
And I think that’s actually enough if you’re honest about it. Not the best day. Not the justification story. The Tuesday.
What’s your typical Tuesday feel like?
The Framework (really this time, I went sideways there)
Look, I’m not saying “leave everything that’s hard.” That’s not the point. The point is: there IS a threshold. The threshold is earlier than you think. And the feeling of momentum -- “this is still working” -- is not evidence that you’re still in the healthy part of the run.
The opportunities that FEEL most alive are sometimes the ones where
most of the opportunity has already passed.
The career that FEELS most established is sometimes the one where
you’ve already gotten everything it had to give you.
The identity that FEELS most solid is sometimes the one most overdue
for an update.
This is annoying. I hate that this is true. It means the comfortable feeling is partially a warning sign.
It doesn’t mean you always leave. It means you CHECK.
Cuz sometimes it’s comfortable and it’s sustainable.
The check is three questions.
What does the typical day look like?
Am I staying because it’s good or because leaving is hard?
If I stripped out the best memories, would the average still clear my bar?
You don’t have to leave. You just have to look at the typical day honestly.
Permission / Question
Here’s what I want to leave you with.
I stayed in acupuncture for a year after I knew. I stayed in insurance for longer than that. Not because I didn’t see it -- because leaving meant becoming someone else, and becoming someone else is the scariest thing a person can do, even when the someone else is better.
Every major good thing in my life came after an exit that felt like failure at the time. Every single one. The speaking career. The marriage that fills me with joy everyday. The version of me that can stand in front of a crowd of 50 to 2,500 people and be honest instead of performing.
(Well, I perform, but I’m not lying. I’m just trying to kick ass.)
None of that exists if I stay in the thing that was “pretty much kinda working.”
So here’s the question, and I’m genuinely asking, not rhetorical-question-as-motivational-poster asking:
What are you still in -- a job, a habit, a way of thinking about yourself -- where the highlights are carrying the story but the typical Tuesday has already turned?
You don’t have to answer to me. You don’t have to answer to anyone.
But I think you probably already know which one it is.