Making Decisions at Crossroads

It’s been a week filled with many meetings, but I want to share two I had this morning at my favorite coffee shop in Cambridge.

I met with a current Harvard b-school student who is looking for a job. I then met with a b-school alumnus, who is on his second start-up and was wondering if he was doing the right thing as he watched his friends on more-typical corporate tracks climb the ranks.

I really relished these conversations as we brainstormed career options. Interestingly, both asked me at they end what they could do for me. “Actually,” I said, “there is something. Promise me right now that you will always follow your gut on career decisions. Don’t do things to seek the praise of others.”

I walked them through some of my career decisions and how the best ones were the contrarian ones: saying no to a private-equity firm, leaving a promotion offer at Bain & Co., saying no to working for Jeff Bezos at, and leaving a VC job to starts a new firm.

In each of those situations, I had people tell me that I was making the wrong decision. In each of those situations, however, I felt high conviction. And, in each of those situations, I was pretty scared.

I’ve found that “crossroads decisions” are the most difficult. You’re often choosing between two pretty good options, but very different ones. You can poll friends and family. You can seek mentors’ advice. But, in the end, you have to make the call. It is your life.

If you’re nearing such a decision, here’s one observation: the gut is always true. Whenever I’ve followed my gut, the decisions have later proven to be the right ones. Whenever I’ve overruled my gut, I’ve paid for it in spades.

But, what do you do if your gut hasn’t clearly spoken? My advice is this: make no decision. Hang out a bit, forge ahead and buy time.

Eventually, your gut will speak. Your inner being will develop conviction. Then, have the courage and confidence to follow it.


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