The Weightiness Every Leader Knows

You aren’t alone. One of the defining experiences of being a startup founder was the heaviness I carried at every waking hour. Now I see it in every other founder I speak with.

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In late December 2018, we were a month or two into a process to sell the company we had started 7 years prior. Our preferred buyer was Australia-based, so with 24-hours noticed we made the 16-hour flight from Los Angeles to Melbourne. My head of engineering, head of product, my wife, our 6-year-old son, and me. Quite a crew.

After a few days of intense diligence in Melbourne, my family and I planned to spend a long weekend in Sydney to rest and explore before making the flight home for the holidays.

The first day in Sydney, with my family taking mid-afternoon naps in the other room, I had an experience I will never forget. What happened was my first experience after 7 years of the weight lifting.

The weight of leading an early-stage company had become such an ever-present force upon me in life that I rarely sensed its existence.

I felt the results:

• The sleeplessness at 3 AM several nights a week

• The rushing thoughts

• The certainty a threat was present to the business or to my life even when none was

• The inability to listen earnestly even to a close friend over dinner

• The looking backward at the end of each passing year with the sad feeling I’d not been present in my own life

I am one year out now from being a CEO. And I am still amazed at the difference it has made in my experience of my own life to set down that weight.

Yet we need leaders willing to carry that weight. In this time of crises more than ever.

I spend my time now coaching other founders as they find their own way to shouldering the weight in their own work and lives. And I wish I had easy fixes; I don’t.

I know together is infinitely better than alone. Together with a coach. Together with a therapist. Together with your cofounders, your team, your friends, your partner, anyone you trust with whom you can share the ups and downs. And share you must. Great leaders cannot and must not lead alone.

I know taking care of your mind and body pays wondrous dividends. For me, that means meditation and working out.

I know rest is paramount. 8 hours a night of sleep. Weekends off.

But there are no easy fixes. The only way I know to carry the weight is simply to carry the weight.

My gratitude and admiration to those of you who find yourselves carrying such weight today. To our entrepreneurs and to our business and civic leaders. Thank you.



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