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

As part of my continuing Transitions to You 3.0 Series, I interviewed Ray to hear his story. 

 Ray started his career in the large-corporate world, added a couple of gigs with smaller companies, and after a dozen years of working for others, he founded a company which he led for 11 years. Ray sold his business eight years ago, at the age of 45, and today is the sales and business development leader for a company where he has no ownership interest. 

Much like Jake, who I wrote about last month, here, Ray was burned-out after the sale. 

“The guys who acquired my company were hardcore, high motor people. Because I had an earn-out, I was spending all my time protecting my customers and my employees. It was exhausting. I managed to stay twelve of the fifteen months of my agreement.

I had a two-year non-compete, which at the time seemed onerous and, in retrospect, was a gift. 

I remember reading a lot and reacquainting myself with what was going on in the world. It turned out to be a sabbatical year. I had already decided I was not ready to start another business. I planned to work for someone else for a while and figure it out. I didn’t realize how hard it would be to find something because of where I was in my life and wellbeing.”

Ray hired a life coach shortly before he exited the acquiring company. The coach told him he was “suffering from PTSD and should see a therapist.” Ray chose not to go the therapy route, but he committed to coaching and learned a ton from it. 

With the help of assessments, coaching helped Ray understand his style and his strengths. He learned to use this knowledge to choose what would be next and develop a life plan.  

“I spent time re-establishing my health, my brand, and discovering what I enjoyed. I starting blogging, got more into music, joined a band, doing things I hadn’t done in a long time. I had some repair work to do with my family, and I got busy doing it. While I had been there for all the ball games, etc., I was rarely mentally present. I was fortunate to have this second chance to be there for real.”

On the business side, Ray began consulting with startups. Consulting enabled Ray to stay in the game, but he soon realized it wasn’t for him. He missed going to an office and having colleagues.

His work with the coach helped him see that starting a business wasn’t for him, at least not right away. Together they looked at various paths along several dimensions, and entrepreneurship had too many red lights. Ray was fearful of the toll it might take on his family, again, and didn’t want that or the financial risk.

He ultimately settled on sales management. His first gig was a practice run, not the best fit, but it got him accustomed to working for someone else again. 

When I asked him if he still had the itch to start another business, he responded, 

“Entrepreneurship is in my blood. I’ve always been around it. I aspired to it because of my dad, who was an inventor and a successful business owner. I also had grandparents and an uncle who were successful entrepreneurs.

I’ve learned so much from the first time and working with others. I am torn, I don’t want the stress of running my own business and the risk to my relationships with my wife and kids. Maybe a side hustle? I feel as though my entrepreneurial journey went unfinished.”

Here are the learnings Ray shared: 

#1 on selling your business

  • Be prepared for the huge distraction the sale will be and the fallout afterward, the aftermath, even in the best of circumstances it is going to be a life change. 
  • Hire a coach 
  • Take time off, allow yourself time to get your perspective back – The further away I get from my company, the more I see how I made small things matter to my psyche. I had to relearn the philosophy I wanted to live by, “when something maddening happens – ask yourself if this is going to matter in an hour, in a day, in a week, in a month in a year.”

If you decide to work for someone else:

  • Be prepared for how your perspective needs to change from being an employer to an employee
  • Get a first gig. I got better at being an employee the second time. 
  • Be selective about your manager and the corporate culture. The first time I focused solely on choosing an interesting business model. The second time I focused on culture as my number one requirement, and I was lucky to find a manager that valued my contribution.
  • Recognize that when you are an employee, managing up is at least as, if not more important, than managing down. 

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

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