Choosing What Didn’t Make Sense (on Paper)

A lot of my drive back then was just wanting to prove I could do something different, but my friend Mason caught me off guard. We had this long conversation—half venting, half therapy—where he basically said, “You know you’re not scared of the work. You’re scared of looking like the guy who couldn’t cut it in the normal world.” That’s what clicked. Challenging the status quo isn’t just a logical decision. It’s an emotional one. I recognized I wasn’t blocked by skills—I was blocked by how it would feel to be seen trying something different and risking looking foolish.

So, if you’re in that spot—feeling stuck or restless—it probably isn’t your résumé holding things up. It’s the emotional math of what happens if you step off the obvious ladder.

The Gravity of Staying Put (and Why It’s Not About Skill)

Everyone feels it. The gravitational pull toward the “obvious” ladder. Culturally, it’s everywhere. Stay where the paycheck is predictable, stick with the titles people recognize, move in the direction that makes sense to your parents, your mentors, or that imaginary voice in your head that says don’t rock the boat. The tough part? Just because something is the “obvious” path doesn’t mean it’s the right one. I had to admit that what looked right on paper wasn’t right for me.

And the numbers bear out that inertia: Even when new options land right in front of you, 76% simply stayed put due to lack of time, apathy, and skepticism. Sometimes it’s easier to do nothing than to face all the unknowns at once.

What keeps smart people rooted in place isn’t usually lack of technical chops—it’s the storm of emotions that come with uncertainty. For me, it wasn’t “can I figure out Swift?” It was, “What if this doesn’t work and everyone sees me fail?” Fear of judgment showed up in ways I didn’t expect. Uncertainty hit harder: will the money last, will I regret not having that union card in five years, will my old colleagues think I got lost? And underneath all that, identity turbulence. If I don’t call myself ‘engineer at the plant’ anymore, what am I actually?

You can be excellent on paper and still feel completely thrown when the story you’ve told about yourself starts to bend. I wasn’t afraid of learning—I was afraid of who I’d be if it didn’t work. That’s where most engineers I coach get stuck—not the skills, but the emotional cost of flipping the script.

So let’s reframe courage for a minute. Courage isn’t recklessness. It’s not about tossing everything in the air and hoping it lands. Real courage is small, structured moves. A little push past the comfort zone, with a strategy you can live with.

Back when I was first seeing this, I didn’t call it “design thinking.” I mostly called it “winging it and hoping I didn’t regret it.”

Stick with me—next, I’ll show you the exact plan I use to try out new directions without burning bridges or needing a permission slip. This is how unconventional moves become safe enough to try, and you get to decide the next step.

Testing a New Direction to De-Risk Engineering Career Change (Without Burning Everything Down)

A 30-day sprint is all you need to learn more than months of circling the “what if?” question. For me, keeping experiments this tight and time-boxed let me move fast, gather real-world data, and adjust quickly before anything got high stakes. The point isn’t to flip your life upside down—just to chip away at inertia, day by day. When I lead engineering teams, we ship in short cycles for a reason. You get clarity in motion, not from waiting for confidence. Use the calendar to your advantage. It turns intention into momentum.

Start with exposure. This is where most people skip ahead, but it’s genuinely the lever that pries you out of your default assumptions. Block a couple of weeks, and line up 6–10 conversations with people living along alternative engineering paths outside your current ladder. No recruiters. No safe choices. Aim for the folks you’d never swap resumes with.

Last year, I reached out to a former avionics engineer-turned-woodworker, an indie SaaS founder, even a clinical researcher now building games. The big shift happens when you let their “logic” bump up against yours. It’s less about chasing their results, more about rewiring how you see what’s possible. I keep noticing: my confidence grows as soon as I hear concrete examples of how other people de-risked their own pivots. Turns out, the friction is rarely technical—it’s deciding what assumptions to keep or question. Listen for contradictions, and let them break up that inner monologue that says, “But this is just what people like me do.”

Somewhere in there, you realize these conversations aren’t all warm fuzzies or professional banter. I remember one call where the other person’s internet kept dropping out. We’d get halfway through a story about a failed side project, then—total silence, frozen mid-laugh. When the connection finally came back, she owned it, shrugged, and joked that her whole jump had gone like that: fits, starts, awkward pauses, then getting back to it. I thought about that later when I was wrestling with yet another app crash at 2 a.m. Not everything works the first time. Or the third.

Next, it’s all about small career experiments—emphasis on small. I learned faster by building tiny, often unfinished prototypes than by perfecting some big ambition in private. If you’re an engineer, think of it as running a test case—what’s the minimum you can build, ship, or join that teaches you something new about yourself or your fit? Grab a scoped freelance project off Upwork. Partner on a micro-collaboration for a nonprofit or open source. Commit five hours to an MVP and launch to a friend group.

The secret isn’t the project; it’s how clearly you define what question you’re trying to answer—is this kind of work energizing or draining? What’s the weirdest part of transitioning from a clean codebase to someone else’s messy repo, or from status meetings to async feedback? You’ll adapt faster shipping scrappy, low-pressure builds than waiting for the perfect entry point. Don’t let “all or nothing” sit in the way—one purposeful experiment teaches more than a semester’s worth of reading.

Safety nets turn wild ideas from reckless to reasonable, and they reduce risk during an engineering transition. Before I try anything beyond the edges, I always define my financial runway. How many missed paychecks, or hours off contract, can I stomach without sweating bullets? Write down clear guardrails—don’t let side experiments tank your main work, and always sketch a return path in case it isn’t what you hoped. Honestly, knowing I’ve got a fallback plan isn’t a sign I don’t believe in myself. It’s the reason I can push further out, knowing I’m not betting the farm every time I try something new.

Now, to avoid measuring yourself with someone else’s yardstick, define personal success and write down your personal success criteria. Pick three to five signals that actually matter to you: does this path give you more energy, deeper learning, a sense of traction, or autonomy day-to-day? Don’t fall for applause chasing or titles that sound good in the abstract. Signals like competence, autonomy, and belonging actually tie straight to how our motivation works at its core, according to Nature. These are the dials that matter far more than public perception in the long run. I care way more about how each day feels than how it’ll look on LinkedIn, and so do most people once they’re honest about it. Control, fit, and momentum always beat the default story.

Finally, get real about your time and who you let into the experiment. Physically block slots on your calendar or you’ll keep letting “real work” win. Pick the folks you actually want to tell (and those you don’t), and decide whether you need privacy or encouragement to stick to your 30-day plan. I check in with myself and someone I trust at least weekly—that rhythm makes course corrections obvious before things drift way off track.

Building Momentum (Without Burning Out)

Here’s how I keep a 30-day sprint from feeling like a moonshot. One new conversation each week, one micro-build (however messy), and one honest reflection—usually written, never polished. That’s it. Tiny, repeatable moves compound faster than you think, especially when you treat each as routine instead of heroic. I’ve noticed progress accelerates once I let the cadence be mechanical, almost boring, so showing up isn’t a debate. For what it’s worth, the most meaningful pivots I’ve made started with small, predictable steps that built into something real before I even knew it was happening. So don’t overcomplicate it—just loop the cycle: exposure, experiment, reflect, repeat.

For tools, I keep it simple. Calendar blocks keep the schedule visible and honest, and a quick decision log—nothing fancy, just dates, actions, stray reactions—captures what actually happened. Tacking a lightweight scorecard onto this makes it obvious if things are moving or stalling. Every week is basically just a learning loop to iterate on. I’ve used Notion, a physical notebook, even sticky notes—none of it matters as much as whether you check in regularly.

Peer judgment is the shadow that rarely vanishes. I handle it by sharing selectively. With people I trust to root for the process, not just the outcome. I frame this for myself (and anyone I loop in) as professional development, not a wild gamble. Honestly, I stopped over-explaining once I realized not everyone needs a status report. If you need reassurance: courage with real guardrails is responsible, not rash. Anyone worth your time will get that.

Quick tangent: the first shelf I hung after moving leaned like a question mark until I shimmed it. Proof that small course corrections beat starting over. It’s the same for careers.

Turning Evidence Into Action (and Keeping the Wheel Turning)

Decision day always comes around, even if you try to put it off. This is when I go back to the scorecard, stack my real signals against the questions I started with, and make a call. Am I doubling down, tweaking the approach, or pivoting entirely? No one’s going to appear and give you permission. That’s the point—owning your decision means trusting the evidence you’ve gathered, not the noise from everyone else’s opinions. Back after the Navy, I’d convinced myself there would be some moment when it all felt “clear.” Turns out, it’s always a bit of a guess.

If things flopped, your safety net did its job. Adjust the next experiment, keep what worked, scrap what didn’t. When something clicks, it’s time to nudge the boundaries. Stretch the experiment, sign a tiny contract, or negotiate for protected hours. Either way, you don’t have to overhaul your identity overnight—let it evolve at a pace that feels safe and real.

Here’s the truth: if nobody raises an eyebrow or asks, “Are you sure about this?” your choices probably aren’t bold enough. That friction is how you know you’re actually at the edge—take it as a signal, not a stop sign. The right kind of skepticism usually means you’re drifting off autopilot, which is exactly where growth happens.

Looking back, stepping out after the Navy taught me that courage—when you fence it in with tight constraints—is how control is built. Start your own 30-day test. Let fit and momentum have their shot, and you’ll find freedom comes not from chaos, but from a plan you’re willing to own. I’m still glad every day that I picked the path that felt right, not the one that made sense on someone else’s scorecard.

There are days when I still wonder what would’ve happened if I’d taken that union card. Maybe I wouldn’t have to check my health insurance so often, or explain weird app bugs to confused friends. But most days, the tradeoff still feels worth it. I haven’t figured out how to stop second-guessing everything, and maybe I never will. That’s just part of the job now.