Startup CEO Second Edition Teaser: Thinking about Your Next Step

As part of the new section on Exits in the Second Edition of the book (order here), there’s a final chapter around you as CEO and thinking about what you do next. I’ll start this post by saying, while am really happy with where I am now (more to come on that!), I am not happy with the way I handled my own “next steps” after the Return Path exit. I did follow some of my own advice, but not enough of it. I jumped back into the fray way too quickly.

Some exits leave CEOs in a position of never having to work again – those are good in that they give you more time to think about what’s next and more options for what’s next, but no financial forcing function to do anything. Some CEOs want to work again in the same field, doing another startup or being hired to run a larger company or focusing on serving on boards and mentoring other CEOs. Some want to transition to a different kind of work entirely.

But no matter what your circumstances are, the most important thing you can do after selling your startup is to downshift and take time off. You probably haven’t done that in years, maybe decades. You may feel like you only have one gear – ON – but in fact, you can get into new patterns of life and take time to enjoy and appreciate things you may have neglected for years and do some of what Stephen Covey calls “Sharpen the saw.” Here’s an excerpt from the book about this:

The week after our deal closed, I made a list of everything I wanted to get done in my downtime. Once I got past everyone in my family rolling their eyes and saying things like “of course you have to use a spreadsheet to make a list about how to relax,” I realized there were three types of items on my list. One was personal or home admin tasks that I had either ignored or wanted to get ahead of. Two was home admin tasks that had fallen to Mariquita while I was working hard and felt like I should now take off her plate. Both of those feel – rightly so – like work, although they are all a far cry from actually working. But the third type of item on my list was “me” items, which included things like what kinds of books I wanted to read, how I wanted to take care of my physical well-being differently both short term and long term, and things like spending more time taking guitar lessons (something I’ve done on and off over the years) and stone sculpture lessons (something I’ve never done at all but that has always interested me greatly).

There’s more to thinking about your next step than just clearing your head, of course. You have to spend some cycles being reflective about the journey you just went on. Our senior team, including a couple long time alumni, gathered and did what I call the “ultimate post mortem,” reflecting on lessons learned over 20 years. I spent some time thinking about how to tell my story, what my own narrative was about the journey. And I came up with my framework for deciding what to do next – that checklist of the things I wanted and didn’t want in my next job, which is detailed in the book, and which I’ll talk about more in the weeks to come as we prepare for the public launch of our new company. But for now, this is the final teaser post I’ll write about the Second Edition of Startup CEO: A Field Guide to Scaling Up Your Business. Next week, though, I will write about the sequel my colleagues and I are writing at our new business.

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