When I left eBay in the summer of 2006, I had never not worked full time in my adult life. I had options available to me that I could only have imagined when I started my career: a wonderful wife and family who wanted more time with me, good career options (I sat on 5 boards at the time), and the economic freedom to do whatever I wanted with the rest of my life. However, I really struggled to get comfortable in this new situation.
I remember clearly attending an event at our club and sitting next to a gentleman who told me that every day he would come to the club to eat breakfast, read his paper, hit the driving range, then play a round of golf. Good for him, but I told my wife I could never spend my time like that. I also struggled mightily with the concept of taking money from savings as opposed to putting money in. I knew economically that we were covered, but I was unprepared for the emotional struggle of not contributing.
But in less than six months of unemployment (and a few months from our youngest child heading off to college), I returned to work at the end of 2006 as CEO of LiveOps.
My wife and I agreed that I would commit no more than 5 years to the new company. It is now 2011 and I have recently stepped down from my responsibilities as CEO of LiveOps.
Now that I’m “retired” again, I’m really excited about implementing a plan that has all the elements in it that I want this time. The inspiration came from a few places. First, when I was at LiveOps, we encouraged our Independent Agents to be CEO’s of their own destiny, where they would work on their own terms, every day. I was inspired by this message and committed to live by it in retirement. Second, I ran into Mitch Kapor. Mitch created Kapor Enterprises so that he can remain engaged with new startups while working when and how he wants.
I want to spend my time and energy in retirement on things that are highly engaging but not sticky (like being a CEO of a major company for five years)—except for my time with family, which I hope to get much more of. That is, I want to be engaged in things I’m passionate about but I don’t want to run them. I thought long and hard about what stage of company I most enjoyed and realized that helping early stage entrepreneurs is fascinating. I also wanted to stay in close contact with lots of people I had worked with over the years and so around a year ago I created the Webb Investment Network. On top of that, my foundation is up and running, I am in the process of signing a contract to write a book, and I’m looking forward to finally getting to all the travel that my wife and I had hoped to do over the years. First up, Australia and New Zealand early next year.
I am only a few weeks into this new world. It is less structured, by far, than the world I was just in. I am squatting in different places for office space, meeting in coffee shops, etc., but so far it has been exhilarating! I have already been to one getaway in Jackson Hole with my wife and we have others planned soon.
I am totally committed and excited about being in Retirement 2.0, where I felt lost in Retirement 1.0. I have been told that there are a lot of bets out there on how long I remain retired this time. I’ll happily take them up on it though because I don't think of myself as retired, but as the CEO of my own destiny. I am spending time on what I want, how I want, and with whom I want. It is a privilege to have such options and I can’t wait to embrace them.
Wish me luck!