Life is like a record album composed of songs to form the whole. From age 24 to 40, I had been playing the song “Entrepreneur.” I set a goal when I was 25 to one day found a tech company and take it public by the time I was 40. Fifteen years later, I achieved that goal—my ultimate BHAG or “Big Hairy Audacious Goal.” Only a few friends, my parents, and my wife knew about this very personal BHAG, and society expected me to keep singing the same song over and over again. This was natural, expected even; I had become typecast, like an actor that keeps playing the same role. But as I wrote about in my “Time Is Money or Is Money Time” post, I was determined to step back and think deeply about my next move after being the CEO of Bazaarvoice. I didn’t want to just set the same goal all over again. I knew I wanted to help entrepreneurs. I had always enjoyed doing so while I was at Bazaarvoice and Coremetrics, but I had done so very sparingly due to the time constraints. I had love in my heart for Austin, Texas, and thought I should do my part, along with many others like Josh Baer of Capital Factory, to help our scene evolve. So I jumped into that part of the arena but in a more “grandfatherly” role as opposed to being the actual “man in the arena.”

Changing my song from “Entrepreneur” to I guess what I would call “Startup Catalyst” was tougher than you may think. Your mind gets into a groove; it becomes accustomed to running a program. My body and mind had been programmed for a tremendous onslaught of activity. Building Bazaarvoice alongside a great team, taking a company from $0 to over $100 million in sales in six years and going through the initial public offering gauntlet was no cakewalk. It was exhausting but also exhilarating at the same time. So my mind started to play tricks on me. It wanted me to go back to the same groove, to what it had been used to. To put it mildly, there were some days when, at the age of 41, I woke up thinking that I should dive back into the arena as an entrepreneur. I had all of the capabilities and experience to be there. What was I waiting for?

It took me awhile to realize that the most powerful antidote to this feeling was to “lean in” more. I was not only starting to enjoy helping entrepreneurs more via Hurt Family Investments, I also enjoyed being a very involved parent. I attend more field trips for our children than most dads, and I’m a better husband. My wife Debra had invested in me for so long, and it was time to help her more too. It was time to exercise more, invest more time in my diet and getting more educated on nutrition, and take trips with friends and vacation with my family. I took my first daddy-daughter trip, my first son-parent trip, and other trips that I’ve always thought about but never had the time to really act on.

In short, it’s hard work to play a new song on your record album of life. It takes a lot of personal determination, not unlike the determination it takes to quit your job, found a new venture and become an entrepreneur in the first place. Last week, I was on the phone with the co-founder of a very large retailer, one you would all know, who had long since moved on. I told him about my journey at age 41, and he agreed that it is one of the most difficult things one can do. He also changed his song and faced many of the same moments of doubt that I did. The more successful the entrepreneur, the more society is expecting you to keep belting out the same song.

"Life is like a record album composed of songs to form the whole." What song are you playing?

“Life is like a record album composed of songs to form the whole.” What song are you playing?

If you keep at it, eventually the societal pressures will die down as people start to see that not only you are sticking with the new tune, but those around you can tell that you are genuinely enjoying the music. This is what I noticed. And you can’t fake it. Either you love the song you are singing on the record of life or you don’t.

Days removed from my 43rd birthday, I can now tell you that the work is really worth it. But it requires a lot of determination and mental perseverance. You have to give it enough time, and eventually the new tune starts sounding really, really good. I learned just how good shortly after I turned 42, right after receiving the biggest kick in the gut I had ever experienced. You can read my “Was 42 the Answer to My Life, Universe and Everything?” post to learn more. It changed my perspective forever. I love my new song “Startup Catalyst,” and you can read more about why in my “What I Love about Angel Investing” post.

I guess the question you may still be asking is whether I will ever start a company again? The answer is probably. I am an entrepreneur at my core, and Hurt Family Investments is indeed a way of practicing entrepreneurship. Having enjoyed “Startup Catalyst” for the past two years I can tell you that if I do start another company, I’ll do it very differently from before. If I become an entrepreneur again, I’ll do it in a way where I can still enjoy the mosaic of activities that I’ve gotten used to. I’ll do it in a way that honors this new tune. I’ll probably have colleagues work alongside me from the start. One, or more, may even be the CEO or COO from the beginning. I’ll probably do it in the spirit of the book Small Giants, which explores a more evolved way of thinking about entrepreneurship. It is one of the best business books I’ve ever read, and I read it when I was 42 years old.

I would love to hear about how you have handled big life transitions, both the good and the bad, and what advice you have to offer others to change their song on the record of life.

Editor’s note: The original version of this post appeared on Brett’s Lucky7 blog Feb. 14, 2015—the day he turned 43 years old.



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