The worst career advice I ever received

By Nick Caldwell

Today I had coffee with a mentee and he said something which brought an old buried memory back to the surface. He said, “If I want to be a manager then I have to wait until my boss or another manager leaves.” I paused for a moment, recalling all the times I’ve heard an aspiring manager say these exact words. I wanted to just tell him, “There are so many opportunities out there, why wait?” But instead I, shared this story of the worst career advice I’ve ever received.

The year was 2011, I was a line-level engineering manager and had been working in the same product group at Microsoft for 9 years since the start of my career. I had a friend, Paul, who’d also been working with me as a peer for several years.

Things weren’t looking good in our organization. Almost every week someone left, product strategy changed bi weekly, and no one was certain which way was up or down. Yet we floated on. I was tasked with several questionable projects and generally kept myself and my reports shielded, but underneath a thin veneer I was afraid. Later, I’d learn to understand what was going on (upper-management, politics, etc). But at the time I was an uninformed junior manager and it simply felt like chaos.

For the first time in a long time, I began exploring employment options elsewhere. I managed to line up a risky but interesting management role on a new project team in a totally different part of Microsoft. Having worked in one team for near a decade I wasn’t sure if I should make the switch. I knew all the ropes, my co-workers felt like family, and my manager loved me.

I went to Paul and asked for his advice. He told me, “Stay! When all of these other people leave there will be a power vacuum, open positions, and you’ll be able get promoted quickly.

His opinion felt logical and staying would certainly be less risky. I didn’t immediately reject the thought. At the same time, was that really how I wanted to rise up the ranks? After grappling with the decision for a week, I took the leap of faith and left the team I’d been with for almost a decade.

The new project was immensely difficult, and I worked as hard as ever to grow the team and bring the product MVP to life. Within 6 months I was promoted to a position that gave me 30 engineers to manage. The product caught fire and 2 years later I was leading a team of 150. A year later I switched roles began work as an executive leader.

Paul stayed behind. To this day he is still in that team in the exact same role. We do keep in touch and whenever we talk the conversation eventually makes its way around to him wanting to switch and do something new. Paul doesn’t like the product he works on or the teammates he works with all that much. “They aren’t innovative.” He doesn’t have other obligations that would hold him back. I ask him why he stays, and he talks about needing the right opportunity. “You got lucky when you left,” he says. So we talk a lot about finding opportunity, the future, and risk, and luck. I love those talks and always come away feeling personally inspired.

Yet, I think Paul will stay a while longer. And I sometimes wonder what my career would have been like if I’d taken his advice. It’s better to look forward.

“If I want to be a manager then I have to wait until my boss or another manager leaves.” Fundamentally, I believe differently and I left my mentee with the following observations.

Chaos isn’t a ladder to climb. It’s unwise to manage your career through the randomness of the universe, decisions made by other people, and org chart Brownian motion. Even when your manager, company, and peers have your best wishes in mind, you still must manage your own career with intent. Owning your career means have a picture in mind of what you want to do and proactively looking for opportunities which fill the canvas.

No opportunity will be perfect. This is the scary part — tradeoffs. There will always be new people to meet and skills to learn. You might need to give up mastery in a technology and become a student again. You may need to trade off pay for potential — everyone working at a startup implicitly makes that call. Your commute might suck. Your work life balance might suck. Maybe the workplace isn’t as diverse as you’d want. Perhaps the Chief Architect doesn’t agree with your tabs vs spaces world view. Maybe a million other things. But if you have a long-term career plan based on piecing together the right skills and experiences, it becomes easy to assess how any new role fits into the big picture.

Finally, comfort is a beautiful garden but careers won’t grow there. For me: it took 9 years to figure this out. For Paul: I’m optimistic he’ll realize it someday and I’ll keep checking in. For you: if there’s a move you’re hesitating to make, I hope you’ll look past fear, imperfection, and comfort to take the leap. We work in an amazing field, technology. The opportunities are vast, the rewards greater, and there are no wrong decisions to make, save one. Standing still.

rock on
-nick