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Golden Handcuffs Don't Feel Like Handcuffs

Jono Herrington on March 18, 2026

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 pro...
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Anna Villarreal

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.

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Jono Herrington

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?”

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Anna Villarreal

✨️🦄

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Sylwia Laskowska

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.

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Jono Herrington

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.

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Redha Zidan

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.

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Jono Herrington

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.

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ferceg

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".

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Jono Herrington

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.

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Apex Stack

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.

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Harsh

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.

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Jono Herrington

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.

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Kanwal Oswal

When the challenge is gone and everything has been stable for a while, its easy to start feeling 'not sharp'! Well written

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Jono Herrington

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.