Listen to my recent appearance on the ‘On The Brink’ podcast here.

As part of my continuing series on transitions to You 3.0, I interviewed Jake to hear his story of two life transitions and what he learned from each.

Jake and his partner sold their first company in 1996. He was only 41 at the time, and while he wasn’t emotionally ready to move on, the market was starting to turn, and they knew it was the right time to sell. 

The process of selling the business absorbed his full attention, but the afternoon after the close, Jake went home ill-prepared for how he felt and with no idea what was next. 

“Before this, my biggest transactions were – car, marriage, house. I was an emotional wreck. I turned on the TV, sat down to watch and immediately knew that was not what I was going to do. But I was so exhausted, that I spun out. In retrospect, I was depressed. I’ve never been depressed before or since, so I didn’t understand what was happening. I was aimless for about three months.”

“The kind of coaching you do wasn’t available back then. If it were I would have started to think about actions before the end arrived. Working with you would have given me the confidence to trust myself, that something would happen.”

On the positive side, once Jake got himself moving, he and his previous partner started a new company.  

“Fast forward 20ish years later, when I sold my last company, I knew I had to work not to be blindsided by the ending. While I knew I had to devote my attention to the sale, I also knew I had to start looking around for what would be next. For me the looking around was enough, it gave me the confidence that something would happen, I didn’t have to know what it was.” 

When you get off the treadmill, your heart is racing – you need to walk around, slow it down, not stop and watch TV.

Today at 65, after walking around and exploring options for about a year, Jake has built a life portfolio. He is actively involved with entrepreneurs like himself. He coaches one or two directly, including his son, and he has taken a leadership role in evaluating and selecting candidates for an Angel Fund in which he invests. 

I asked Jake to share what he learned from these two transitions; here are the top 5 he shared:

  1. I was naive not to think about or worry about the future when I sold my first business 
  2. Come to terms with what you want next, think about which option is most appealing; starting or operating another business, helping other companies get where they want to be, learning something new or some combination of options
  3. Think about, when all is said and done, what do I want people to say about me
  4. Along the way, before an exit, make the changes you need to make to give yourself enough distance to objectively see, “your baby will be safe.”
  5. Focus on self-interest – secure my investments – active role – interesting volunteer work or other work that is a fit with my background

Let’s work together. You can learn more about my leadership coaching and peer advisory boards here. 

If you have a story you are willing to share in this blog or know someone who does; please contact me.