Man, I saw that title pop up this morning, and it just hit me. “Is it time to switch jobs?” That question, right? It feels like the universe just throws it at you sometimes, regardless of what star sign you are. I’m not really into all that horoscope stuff, but let me tell you, when that feeling hits, you gotta pay attention. It happened to me a couple of years back. I was sitting pretty, or so I thought, cruising along.
The Concrete Wall I Hit
I was in this operations manager gig for maybe eight years at the same place. It was a big utility company. Good money, decent hours, the commute was short. Everything on paper said I should shut up and be grateful. People would always tell me how lucky I was to have that stability. But man, every Sunday afternoon, around four o’clock, that pit in my stomach just started bubbling up. It was like I was running on a treadmill that was stuck on the same low speed.
I’d hit the targets, push the buttons, sign the papers, and nothing changed. Nothing interesting, anyway. I wasn’t learning anything new. I was just maintaining this whole system that felt like it was built with duct tape and good intentions back in the nineties. My boss, bless his heart, kept talking about “maximizing synergistic throughput” and “leveraging core assets.” That kind of corporate junk talk that just makes your brain hurt.
- I felt stuck in the routine—my daily tasks were identical every single day.
- The company politics were getting thick enough to stir with a spoon. It was all about who was covering whose backside.
- I realized I hadn’t actually built anything new, zero growth, in maybe three and a half years.
I’d look at the younger guys coming in, all fired up about cloud migration and automation, and I just felt old, even though I was only 38. I was just patching leaks in the ceiling while everyone else was talking about building a new roof.

The Moment That Kicked Me Out The Door
It sounds stupid, but it was a planned vacation that went sideways. I took two weeks off, flew out with the family to visit my sister down in Florida, and I swore to myself I was going to unplug everything. No email, no calls, nothing. We were having a good time, finally relaxing.
On day five, though, my phone started buzzing. It was my direct report, totally panicking, sweating bullets. Turns out, the whole legacy system I was maintaining—the one I designed, the one they insisted was critical—went down because some new hire decided to “update” a critical script without telling anyone, and he broke the whole backend. They couldn’t fix it without me.
I spent an hour on the phone, standing out on a damp hotel balcony, walking this poor guy through the manual four-step reboot process. I was trying to talk over kids yelling, drinking a nasty warm coffee, and I was still working. That’s when it hit me: I was the system’s biggest single point of failure. I was the lock. They weren’t valuing me for my innovation; they were relying on me because I was the only fool who knew how the mess was wired. I hung up that call, walked inside, and my wife asked what was wrong. I just told her, “I’m done. We’re doing this. I’m moving on.”
Executing the Great Escape Plan
The first thing I did when I got back wasn’t updating my resume. Nah. I spent four weeks just networking like crazy. I bought coffee for anyone who had left my company in the last maybe seven years. I wanted the real dirt. I wanted to know where the good places were and, more importantly, where the bad places were that just looked shiny on LinkedIn. I didn’t care about titles.
- I talked to maybe twenty-five people. I asked them point-blank: “Are you learning something new today?” and “Do you actually respect your boss, or is he just a talking head?” Forget the salary talk first.
- I started hitting the books again. I didn’t waste time on some expensive online course. I just grabbed three massive textbooks on modern enterprise architecture and some basic scripting, stuff I hadn’t truly worked with since forever. I forced myself to read an hour every night, no excuses.
- Then came the resume part. I didn’t polish it; I re-wrote it. I threw out all the jargon. Instead of “optimized synergistic throughput,” I wrote “fixed the broken scheduling that saved the company $50,000 last quarter.” Real stuff that matters to the bottom line.
I was really careful about applications. I didn’t just blast them out everywhere. I applied to exactly four places over three months. I wanted jobs that scared me a little, ones where I knew I’d be forced to learn on the fly. The interviews were brutal. They could smell the complacency from my old job like I was wearing it. But I kept pushing back, telling them my story—that I wasn’t just looking for a chair to sit in, I was looking for a mountain to climb.
The New World Order
I finally landed at this smaller firm, total chaos, but the good, creative kind of chaos. I took a hit on the base salary, maybe 12% less than I was making, which my wife totally thought was insane. But the bonus structure was tied to new projects and innovation, not just keeping the lights on. That made all the difference. I’m working with systems I’ve never seen before. I’m actually failing things and having to start over, and my brain hurts when I leave the office, and that’s the best sign there is.
The best part? I was only there for eight months, and they pushed me into this specialized role they didn’t even know they needed until I showed them the gap. My old company? They finally hired four different people to do what I was doing, and they still call me sometimes asking for advice. I just look at the caller ID and laugh, hitting the reject button every time. Like my old man used to say, sometimes you just gotta kick the tires and see what falls off. If you’re asking yourself if it’s time to go, the answer, based on my mess, is probably yes. Stop asking the stars and start making your own move.
