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:

• A long-time private equity investor returns to his old firm to remain on partner track. Then is recruited to be COO of a startup. Then again into a similar role at another startup. Then starts a search fund and acquires a profitable business, where he is now CEO.
• A McKinsey vet works at hedge fund, doesn’t like it, goes back to McKinsey for a while. Then is recruited into an administrative position at one of the top asset managers in the world. Now reports to C-level executive and is running one of the fastest growing business units.
• A former product manager in Bay Area nearly drops out of school to work in animated film production, after an eye opening internship at a top studio. Ends up at a gaming company and rides the wave of growth, eventually reporting to the CEO directly. Walks away to risk it all on a new venture of her own.
• A former marketing manager at a CPG company joins a popular yoga studio chain to work in retail operations, but realizes her passion is for the practice of yoga itself. Begins to teach yoga on the side, and eventually leaves her job to start a business of her own — using yoga philosophy and practice to help executives achieve higher levels of performance and satisfaction.

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:

1. Do you love the thing you’re working on?
2. Do you admire the people you’re working with?
3. Are you learning and growing your skills?
4. Do you see an internal path for career progression?

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.

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