Why I Left My Engineering Leadership Role to Go All-In on Coaching
Thinking about a bold career move? Here’s what I learned leaving a steady engineering leadership role to go all-in on coaching—and why strategic clarity matters more than safety.
Two weeks ago, Friday was my last day at Smartpin. I’m now fully back to running my coaching business.
And after a week of being all in? It feels incredible. Just having the space to focus on my clients, on the work that actually lights me up, has already shifted something.
For two years, I’d been doing both: fractional engineering leadership at Smartpin while coaching engineering leaders in between. And I loved it. I got to use both sides of my brain. The strategic engineering side. The coaching, people-focused side. The Smartpin launch was incredibly rewarding: a hackathon project I started at Tile seven years ago finally came to life. Seeing that vision through felt amazing.
But somewhere in the last few months, I started tuning into something.
Running the team for the six months after launch was taking a lot of energy. And the more I leaned into coaching, the more I realized where my heart actually was.
Here’s the thing: my clients come to me with a pattern. They’re crushing execution but invisible to executives. Stuck playing whack-a-mole with fires. Scattered across too many priorities. Afraid to fully commit to what they actually want.
I realized I was doing a version of the same thing.
And honestly? Part of what kept me holding on was the same thing that keeps a lot of my clients holding on: the steady paycheck. Knowing exactly what’s coming in every month feels safe. Walking away from that, even when you know you’re building something meaningful, is terrifying. I had to do the work to trust that I could make this sustain itself. That the coaching business I’ve built over almost four years was real enough to go all in on again (even in today’s crazy world).
That’s the part no one talks about with bold career moves. It’s not just strategy. It’s fear. And doing it anyway.
In almost four years of coaching, I’ve had more impact in single conversations than I sometimes had in months of technical work. My clients are getting promoted. Building real influence. Landing head-of-engineering roles for the first time. Delegating effectively instead of staying stuck in the weeds. That’s the most meaningful work of my career. And I couldn’t do it justice while splitting my attention.
So I made the decision. But I wanted to close this chapter the right way. I led the Smartpin team onsite in Vancouver. We planned the roadmap for the first half of 2026 to set them up for the best possible chance of success. I celebrated in person with the team that I’d built. That felt powerful and complete.
And now? Things are already moving in ways that confirm it was the right call.
If you’re feeling stuck right now — maybe you’re crushing execution but no one sees it, or you’re overcommitted and can’t find a way out — I get it. I was just there. You don’t have to have it all figured out to reach out.
I’m opening up a few 1:1 coaching spots. I keep my client load intentionally small so we can go deep. Book a call at https://jossiehaines.com/meet, and we’ll figure out the right next steps together.
