Climbing Your Own Ladder

Define your growth by your own terms, not someone else's.

When it hits, the moment of clarity feels both sad and surprisingly hopeful. Often the vibrant human on my Zoom call has been climbing one of a few standard-issue tech ladders for many years by that point, ascending from associate to senior, from manager to director, from VP to founder/CEO. So when the moment arrives for them to poke their head above the clouds and look around, eyes squinting in the bright sun, it’s profoundly disorienting when they realize they’re on the wrong ladder.

Whoops! It happened to me too, albeit well short of the highest rungs. After being abruptly shown the door, first by my co-founder at my startup, and then again at Slack, it was clear the problem wasn’t them—it was me. It was the beginning of some long-overdue personal and professional development work that helped me find a whole new career as a coach, not to mention massively improve my marriage. But I didn’t know that then. All I knew was I felt like shit and urgently needed a new gig. Did I mention my wife was three months pregnant?

I know that doesn’t exactly sound like standing atop the ladder of tech achievement. The irony was that while I had hit rock bottom, my LinkedIn profile had never been riding higher. Barely anyone had left Slack at all at that point, so my inbox was full of people looking to learn whatever magic we’d conjured there. I had all the opportunities I’d dreamed of my whole career: VP Product roles at promising startups, advisory roles at VC firms, invitations to speak at conferences and be featured in First Round Review.

These opportunities gave me passing hits of energy and optimism, but none of it fundamentally made me feel any better. I’d been utterly rejected by two of my closest professional partners, and my romantic partnership was being strained by our soon-to-arrive son as well. I was standing on top of the ladder I’d been climbing all those years, but whatever I thought I’d find clearly wasn’t there. No pot of gold, just a lot of questions without easy answers.

Which brings me back to all those vibrant humans on my Zoom calls, asking those same questions:

I got the job I always wanted—now how do I avoid screwing it up?

I’m excelling at my job, but I still don’t feel happy or fulfilled—what am I missing?

We finally found product-market fit, but now things are getting harder, not easier. How do I avoid burnout when there’s no end in sight?

The answers to these questions are as unique as the people asking them, but they all start with throwing away that standard-issue tech ladder. Usually they picked it up much earlier in their career, back when all they wanted was safety and stability. So of course they climbed the ladder with the stamp of approval of their management, peers, and family—that approval counts for a lot! But it’s not everything. So instead of finding what they were looking for at the top of the ladder, most of them find what they have been missing instead. Sad, but surprisingly hopeful too.

So whose ladder are you climbing? What’s at the top, and how do you hope to feel when you arrive? If you don’t like your answers, it’s never too late to build your own ladder, to a destination only you can dream up. You get to decide which direction to grow.

Got questions on how to handle your own situation? Feel free to comment below or get in touch, happy to help. Subscribe now to get future letters right in your inbox.

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