Why big life transitions are so hard and why it is so worth it to keep at it

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 - "Big Hairy Audacious Goal"). Society didn't know about this very personal BHAG (only a few friends, my parents, and my wife did), and they expected me to keep playing the same song over and over again. This was natural, expected even. 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 post being the CEO of Bazaarvoice. I didn't want to just set the same goal all over again (i.e., "now I'll found a sixth company and take it public again"). I knew I wanted to help entrepreneurs - I had always enjoyed doing so while I was at Bazaarvoice or Coremetrics but I had done so very sparingly due to the time constraints that I had (managing high-growth ventures takes a lot of time). I had love in my heart for Austin 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" (a nod to Theodore Roosevelt's powerful speech in 1910). As far as becoming an entrepreneur again and going back to that song, I had to think very deeply about it.

Changing my song from "entrepreneur" to "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 non-stop onslaught of activity. Building Bazaarvoice - alongside a great, great team - from $0 to over $100 million in sales in six years and going through the IPO 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, where it had been used to operating. To put it mildly, there were some days when I was age 41 where I woke up thinking I was a loser now - that I should be back in the arena as an entrepreneur myself. That 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 and more via Hurt Family Investments, I also enjoyed the time to be a very involved parent (I'm at more field trips for our kids than most dads), be a better husband (Debra had invested in me for so long and it was time to help her more too), exercise more, and take some trips with friends and vacation in some bucket-list destinations with our kids and/or Debra (I took my first daddy-daughter trip, our 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 is very hard work to change to a new song on your record of life. It takes a lot of personal determination - not unlike the personal determination it takes to quit your job and found a new venture. 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 on his record of life and faced many of the same moments of doubt that I did. The more successful the entrepreneur, the harder it is as there are more eyes on you and the more society is expecting you to keep playing the same song.

He also shared with me the story of one of his friends (the founder of another retailer you would all know) who failed to make the switch on his record of life. He just couldn't get into the new song - his mind pulled him back to the old music. He let the voices of society pull him back. I think this happens quite often and most people don't talk about it (this is one of my motivations for writing this post). Whether it is a relationship that should have never happened or some other change - like a big career change - one that requires you to really change your tune - some people make it through that and emerge stronger on the other side, but I would bet that most fail people at it and go back to the same song as before. Change is very hard - who moved my cheese again?

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 they can tell that you are genuinely enjoying the music. This is what I noticed over time. And you can't fake it - either you are really loving the song you are playing on the record of life or you aren't (only you can really know the answer to that question and sometimes it requires a very deep level of reflection to figure it out).

Today on my 43rd birthday, I can now tell you that the work is really worth it. 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-years old, right after receiving the biggest kick in the gut I had ever experience (you can read my "Was 42 the answer to my life, universe, and everything?" post to learn more), and 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.

So I guess the question you may still be asking yourself is, "ok, great - so will you everstart 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 (but, again, in a "grandfatherly" way instead of in a "fatherly" way). Having worked so hard at enjoying "startup catalyst" for the past two years I can tell you that if I do I'll do it very differently than before. If I become an entrepreneur again, I'll do it in a way where I can still enjoy the mosaic of activities and impact that I've gotten used to. I'll do it in a way that honors this new tune. I'll probably have operators work alongside me from the beginning - they may even be the CEO from the beginning. I'll probably do it in the spirit of the book Small Giants, which I highly recommend you read as a more evolved way of thinking about entrepreneurship in general. 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. I recently met with the founders of #besomebody - they are all about being brave enough to change your song on the record of life.