I was sitting in my home office on a Tuesday afternoon with a blank editor open and nothing in my head.
Not nothing as in "I'm stuck on a hard problem." Nothing as in the well was dry. The thing that used to make me lean forward at my desk, the puzzle of figuring out how systems fit together, how teams could move faster, how the architecture should evolve ... it wasn't there. I wasn't frustrated. I wasn't angry. I was just empty.
And I felt terrible about it. Because the job was good.
The pay was great. The team was talented. The work was interesting on paper. The company treated people well. I had autonomy, flexibility, and the kind of role most engineers would look at from the outside and think "what's the problem?"
That's exactly what made it so hard to name.
Bad Jobs Give You a Villain
I've had bad jobs. Most engineers have. The kind where the problem is obvious. Toxic manager. Unreasonable deadlines. No growth. Broken culture. You can point at the thing that's wrong and say "that's why I need to leave."
Bad jobs are painful but they're clear. The exit has a reason. You tell your friends, your family, yourself a clean story. "The place was broken. I left." Everyone nods. Makes sense.
You don't feel guilty leaving a bad job. You feel relieved.
Good Jobs Give You Guilt
The drain that comes from a good job you've outgrown is different. There's no villain. There's no broken culture. There's no obvious thing to point at.
There's just this quiet flatness that shows up one Monday and never leaves. You stop being excited about the problems. You stop learning at the rate you used to. You start operating on autopilot because you've solved every category of problem this role will ever give you.
And then the guilt arrives.
You look at the compensation and think "people would kill for this salary." You look at your team and think "these are genuinely good people." You look at your work-life balance and think "I have no right to complain."
So you don't complain. You just slowly disappear into the role. You keep delivering. You keep showing up. But the version of you that shows up is smaller than the version that started. Less curious. Less engaged. Less likely to volunteer for the room you don't belong in yet.
I've watched this happen to engineers I lead. And the pattern is always the same. The ones in bad situations come to me and say "I need to talk about something." The ones in golden handcuffs don't come to me at all. Because they've convinced themselves the problem is them, not the job.
The 2pm Test
It was 2pm on a Tuesday and I couldn't write a single line of code.
Not because the problem was hard. Because I didn't care about the problem. And for someone who's been coding since 13, who built a career on the energy that comes from solving things, not caring was the scariest signal I'd ever felt.
I tried to push through it. Told myself it was a phase. Told myself everyone has slow weeks. Told myself the problem was discipline, not direction.
But discipline wasn't the issue. I could still grind through work. I could still deliver. I could still show up to meetings and sound engaged and hit my commitments. The output looked fine from the outside.
The inside was hollowing out.
How to Diagnose It
I've had this conversation with enough engineers now to know there's a pattern to how the realization forms. It usually takes three questions.
Remove the Compensation from the Equation
I had an engineer once who was clearly disengaged. Solid performer. Always delivered. But the spark was gone and everyone on the team could see it. In our one-on-one I asked him "if every company paid the same, offered the same title, the same PTO ... would you still choose to be here?" He stared at the table for a long time. That silence was the answer.
Most people have never separated what they earn from why they stay. "I can't leave, I make $280K." But that's not a reason to stay. That's a reason you're afraid to evaluate whether you should.
Think About the Last Time You Were Genuinely Excited
Not satisfied. Not productive. Excited. The kind where you lose track of time. Where you're sketching architecture on a napkin at dinner. Where you wake up and the first thing in your head isn't your calendar, it's the problem you were working on yesterday.
I remember what that felt like. Staring at a commerce platform migration, figuring out how to make two systems talk to each other when neither one was built for it. Midnight on a Thursday and I didn't want to stop. That energy is the signal. When it's gone, pay attention. If you can't remember the last time you felt it, the handcuffs are tighter than you think.
Are You Staying Because You Want to or Because Leaving Feels Wasteful
This is the one that cuts deepest. Because it forces you to separate desire from sunk cost. "I've been here four years. I have equity vesting. I built this team. Walking away from all of that feels like throwing it away."
None of that is a reason to stay. All of it is a reason you feel trapped. And there's a massive difference between choosing to be somewhere and feeling unable to leave.
If all three answers make you uncomfortable, the handcuffs are on.
What I've Learned Leading Through This
I sit down with every person on my team and ask where they want to be in 10 years. I wrote about this in my post on mentoring people, not engineers. That question exists partly for this exact situation.
Because when someone tells me they want to be a VP of Engineering, and I watch them slowly disengage over six months, I can name what I'm seeing. "You told me you want to lead a larger org. The work you're doing right now stopped challenging you three months ago. Let's talk about that."
That conversation is hard. Especially when the person is a strong performer. Especially when losing them would hurt the team. But keeping someone in a role that's shrinking them isn't leadership. It's hoarding.
The best leaders I've worked for didn't just develop me for the role I was in. They developed me for the role I was headed toward. Even when that role wasn't at their company. Even when helping me grow meant helping me leave.
I've tried to do the same. Sometimes that means finding a new challenge internally. A harder project. A different scope. A lateral move that reignites the curiosity. Sometimes it means having the honest conversation that the next chapter isn't here.
Both of those are acts of leadership. Pretending the disengagement isn't happening is not.
The Part Nobody Talks About
Here's the thing about golden handcuffs. The lock isn't on the door. It's in your head.
Every time the thought surfaces ... "maybe I've outgrown this" ... the guilt pushes it back down. You're not allowed to want more when you already have so much. You're not allowed to feel restless when the job is objectively good. You're not allowed to leave when people around you would love to have what you have.
Eventually I had to be honest with myself. That 2pm Tuesday wasn't a bad week. It was a ceiling. The question is whether you can break through it where you are or whether breaking through means going somewhere else. I'd pushed as hard as I could push in that role. The ceiling wasn't going to move. So I did.
The skill isn't avoiding ceilings. Every person at every job will hit one. The skill is recognizing it early enough that you leave while you're still growing instead of after you've spent years shrinking.
The Hardest Career Move
The hardest career move isn't leaving a bad job. Everyone understands that. The story is clean. The villain is obvious. The decision makes itself.
The hardest career move is leaving a good one that's slowly making you invisible to yourself.
I know because I almost waited too long. And I know because of what happened after I left. The first week at the new role I felt like a completely new person. Every question felt fresh. Every problem sparked the curiosity I thought I'd lost. The wonder and excitement I assumed had faded with age ... they hadn't gone anywhere. They were just suffocating in a role that had stopped feeding them.
That's what I want every engineer reading this to understand. The energy isn't gone. You didn't lose it. You just stopped putting yourself in rooms that demand it.
If you're reading this and something landed, ask yourself the three questions. Remove the money. Find the last time you were excited. Figure out if you're staying by choice or by default.
The answers might confirm that you're exactly where you should be. Good. Stay and recommit with clarity.
But if the answers make you uncomfortable, don't let guilt talk you out of what you already know.
I write daily about engineering leadership at jonoherrington.com.
Top comments (14)
I understand this on a small scale. My new job takes a lot of my time. The last time I was excited was when I went sniffing in some new software I had no experience in and got myself into a mess. But for 3 days, it was quite exciting. I wish I had time for that again.
That’s a real signal. Not that you need to leave … but that something in your current setup isn’t creating space for curiosity anymore.
Most people don’t lose interest in building. They lose the environment that lets them explore.
The question isn’t “do I still love this?” It’s “when was the last time I had room to?”
✨️🦄
Really interesting perspective!
I like that you’re not pushing the whole “your job has to be your passion” narrative, but instead talking about meaning and how a job fits into your life.
I’ve actually been in that kind of situation before — a job where I could probably have stayed until retirement. Everything looked good on paper, but something just felt… off. I eventually decided to leave, and I’m really glad I did. It took a couple of steps (and yes, some not-so-great roles along the way), but I finally landed in a place where I genuinely feel good.
Now, when I think about changing jobs, it would have to be a really amazing offer to even consider it 😉
But who knows — especially with how unpredictable the market is these days, I guess we’ll see.
That “something feels off” is the part most people try to ignore. On paper, golden handcuffs look like success … good pay, stability, strong team. But the signal isn’t the job. It’s the misalignment.
The longer you stay in it, the more you start optimizing your life around something that doesn’t actually fit.
Glad you listened to that early. Most people don’t until it gets loud.
Can really relate.
My internship experience made me almost consider dropping development career as a whole. Turns out, not every company is like my previous firm was. Learnt some of key red flags when it comes to joining a company and the biggest of the red flag is Ego of the management and potential nepotism in the chain of command.
That experience will sharpen your instincts fast.
A bad environment can make you question the entire path … when it’s really just the wrong system. Ego at the top usually shows up everywhere else. Decisions get slower, feedback gets filtered, and growth gets limited. The hard part is separating “this career isn’t for me” from “this environment isn’t for me.”
Sounds like you figured that out early.
Similar here. Spent the last 10 years building and maintaining a B2B system. There were a lot of interesting problems to solve but today "it just works", the new features rarely require new technologies or intellectual challenges. Last week we had a strange slowdown issue, solving this provided more excitement and required more thinking than months of "normal" development before. But the job, the people, the management, the stability, etc are OK. So I couldn't explain a job change with anything else that "I'm usually bored".
This is such a real spot to be in.
“Everything is fine” is actually what makes it hard. There’s no clear reason to leave… just a slow drift. Those random hard problems lighting you up again is usually the signal.
The question I always come back to is
am I coasting more often than I’m stretching? That’s usually the tell.
This really resonates. The "excitement signal" you describe — where you stop looking forward to Monday — is something I've noticed maps almost perfectly to when I started building side projects outside my day job. I work as a principal architect at a performance marketing company, and the role is great, but the most alive I've felt professionally in years was when I started building a financial data platform from scratch on nights and weekends.
What struck me about your framing is the guilt angle. There's this weird cultural expectation that if you're well-compensated, you should be grateful and stay put. But compensation doesn't fix the ceiling problem. I've found that the antidote isn't necessarily quitting — it's having something outside the golden cage that reminds you what genuine creative momentum feels like. For me that's been programmatic SEO, shipping digital products, and solving problems where I own the entire stack from idea to deployment.
The scariest part isn't leaving — it's realizing you've been comfortable so long that you forgot what growth felt like. Great piece.
This hit close to home. You've articulated something I've felt but couldn't quite name especially the distinction between leaving a bad job (easy to justify) versus leaving a good one that's quietly shrinking you. The 2pm Test' is going to stick with me. Thanks for writing this.
You nailed the distinction. Leaving a bad job is obvious. Leaving a “good” one that’s shrinking you is the harder call.
Glad the 2pm test landed. That one tends to stick.
Appreciate you taking the time to write this.
When the challenge is gone and everything has been stable for a while, its easy to start feeling 'not sharp'! Well written
This is exactly it. Stability feels good… until it starts dulling you. That “not sharp” feeling is usually the first signal people ignore too long.
Appreciate you calling that out.
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