“The best laid schemes o’ mice an’ men often go astray,” trans. from Robert Burns, 1786. (Image: Source)

Don’t overplan your career.

I met a young executive last week who is at a transition point in his career. He spent the last few years at two great companies — one that’s quite large and successful, and one that’s earlier and emerging. He has honed a set of skills, but wanted to take those skills into an entirely new industry. He asked me for advice in finding a fit in that new industry, and how he could reach his eventual goal. He then laid out a logical path to get there and asked for my thoughts on it.

While I’m impressed by thoughtful people who try to plan the next decade of their career moves, I gave him some contrary advice:

“Don’t overplan.”

The tendency amongst smart, ambitious people is to anticipate every contingency, especially when it comes to career planning. The challenge is that the best opportunities confront you serendipitously. Life makes your long-term roadmap 90% worthless. I’ve seen this time and time again amongst friends and colleagues. A few examples just from my business school class:

I am fairly certain that none of these folks, all of whom have high levels of career satisfaction, would have placed their current roles on a long-term roadmap.

Alternatively, I believe the best thing to do is check in with yourself every couple years. I call this process the “biennial checkin.” It’s a much more realistic way to approach your career and leaves open more options, especially those that would not have been on your roadmap previously. The checkin requires you ask yourself a few, simple questions:

If you’re a 4 out of 4, then it probably makes sense to continue to grow in your role. Once you drop into 2 or fewer of 4, then that should trigger a soft evaluation of your options. What you’ll find when you look around are many roles that you could never have planned out — especially in the technology industry, where things change so rapidly.

I hope that some of you will find this framework useful. I’d love to hear alternative ways that you’ve pressure tested changes in your own career. Leave a response below!

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Lightspeed Venture Partners

Lightspeed is a VC firm focused on accelerating disruptive innovations and trends in the enterprise and consumer sectors. Lightspeed has backed 350+ companies globally in the past two decades including Snap, Honest Co., GIPHY, Nest, Nutanix, AppDynamics and MuleSoft.

Alex Taussig

Written by

VC at Lightspeed. Consumer tech enthusiast. Partner to AWA Studios, Daily Harvest, Faire, Vector, Zola, thredUP, RentJuice/$Z, $TWOU, $CBLK. Reformed physicist.

Lightspeed Venture Partners

Lightspeed is a VC firm focused on accelerating disruptive innovations and trends in the enterprise and consumer sectors. Lightspeed has backed 350+ companies globally in the past two decades including Snap, Honest Co., GIPHY, Nest, Nutanix, AppDynamics and MuleSoft.