I’ve come to the conclusion that the absolute worst hell for me would be retiring. Since I started working at WEBC radio in Duluth, at age 13, I’ve always had to do something that felt extraordinary. I left radio at age 20 to become partners in a high-profile Minneapolis talent-management agency; left that agency six years later to start my own talent-management agency; married one of the prettiest/smartest girls in the Twin Cities; moved to Montana; built one of the largest independent telephone companies in the state; traveled all seven continents; became a multi-award-winning author; a popular college speaker; and have been running Encante Entertainment, a 16-year-old talent agency that specializes in the college market.

I’m now at the point in life where I don’t owe a penny to anyone, and Deb (still pretty and smart all these years later) and I have enough in savings that we don’t ever need to work again. Yet today, I’m both pissed and depressed that I lost an opportunity to put a cherry atop my careers.

Two months ago, someone posted on a string below one of my posts a video of a song performed by a young woman. She was the complete package of amazing vocals, songwriting, musicianship, and looks. (Please don’t ask the name of the musician, as I wish to keep that confidential.) I did some research on the woman and sent her a friendly email of encouragement. She responded in kind, and we began exchanging emails.

Then I found out that she was looking for an agent and a manager. The agent part I could handle, as that’s something I do now. But a manager? It had been many years since I’d managed anyone, and the music business had changed a lot.

Then I thought of all the careers I learned and excelled at. If I could build a successful telephone company and college speaking career without prior knowledge, certainly I could catch up on the ins-and-outs of talent management in the digital age. All it took me was two days of studying to feel comfortable enough to return to talent management—and be one hell of a manager.

So my talks with the female musician got serious. She was currently touring outside of the United States, so we had to communicate via emails, phone calls, and video calls. When she finally said “yes” to management, I had to come up with a new management contract, as my previous contract didn’t include today’s digital technologies. I solved that problem by buying an Artist Management Agreement from a music attorney.

I was so fucking excited! I felt like I was in my 20s again, when I was one of the top young talent managers in the country. The main difference was that my life experiences since then would make me an even better manager. I had no doubt that I could make the woman a bona fide star within a few years. Doing so would mean giving up my book writing, but I was willing to do that.

After issuing the contract, the woman had some objections to the terms, which I had to explain and/or volunteer to change. Before long, we appeared to have all the contract issues settled.

A few days later, she sent me some additional changes. I looked over the changes, agreed they were fair, and reissued the contract. She responded with an excited email, stating that she would send the agreement back via DocuSign in the morning.

Then she disappeared for two days.

As you’ve surely guessed, everything fell apart. I know there was another manager (who managed multiple major acts) who was also trying to sign her, but I thought I had won that battle. The actual reason is still unknown to me. The bottom line is that the email she sent me ripped my heart out.

So now it’s a week later, and I still feel sick about what happened. Yeah, I didn’t get that “cherry on top,” but each day I feel a bit better, and I’m back writing the novel I had put aside.

Who knows? Perhaps someday that woman will realize that she could have had one of the most dedicated, talented, hard-working, honest managers in the business all to herself—and she blew it. If that happens, and I’m not in the middle of some other adventure, I will be open to picking up where we left off.

And if there is another artist/band out there looking for management that blows me away, I still might return to my cherished roots. Managing just one more artist/band would be such a grand adventure! But if that doesn’t happen, I will be just fine. I’m in the midst of an extraordinary journey through life, and one major disappointment can’t change that.