Authentic &


Matt Douglas, Founder and CEO of Sincere Corporation

How to Know When It Is Time to Walk Away

Note: This is the second in a series about the University of Rochester Stingers — a group I founded in the fall of 1994. The first part of the series is called “University of Rochester Stingers: My First Start-up.

Part III: You gotta know when to fold them, know when to walk away….

Stress can do crazy things to your body. I learned that lesson the hard way in early December of 1995. I was sick — and not just run-of-the-mill sick. I had a very bad case of pneumonia, and I was absolutely miserable. I spent a few nights in the Student Health Center, and if I didn’t recover in 48 hours, I was going to have to leave school. Thankfully, it never came to that, but I was down and out for more than a week.

At the heart of my stress was the Stingers, the a capella trombone group that I had founded in September of 1994. I longed to have control over the group and fulfill the vision that I had started, but every rehearsal and every interaction with the people in the group was a battle. Cliques had formed (for example Orlando Q., John H. and Bob G. didn’t talk to anyone else and met privately) and my vision was no longer important to the organization. I fought hard — but without the authority to impact change, I was not part of the solution. I was part of the problem.

I learned an important lesson through this realization. The personal characteristic of “self-awareness” is one of the most valuable. People who have the ability to see themselves as others see them are the people that get farthest in life and in business. Are you a person that doesn’t like hearing an audio recording of your own voice?  Do you cringe when you see a picture of yourself? How comfortable are you at looking directly at yourself in the mirror? If you have trouble with any of these questions, I’d encourage you to spend some time getting to know yourself. After all, if other people have to look at you and listen, shouldn’t you try to understand what they see and hear?

As I pondered the new year of 1996, I saw myself as a frustrated founder who needed to turn his attention to his impending graduation. Some say that college “by definition is about transition” and I was about to enter one of the most tumultuous periods of my life. Within a few short months, I’d be saying goodbye to my college years, and making decisions that would impact the rest of my life (that’s not overly dramatic: the decisions I made in the months after college set me down a path that had an impact on my life to this day).

So, as I took a break from school in late December of 1995, I composed a heart-felt and soul-searching letter. It remains to this day, one of the hardest letters I’ve ever had to write. I was acutely aware of the importance of this letter on my personal development, and I wrote and re-wrote sections with the hopes that this letter would be read by future University of Rochester students. It was going to be a living memory of that important time in my life, and I wanted to get it right.

I finished writing the letter on New Year’s Day 1996, and printed out a copy for each member of the group to give to them when school started again in a few weeks. Then I saved a copy for myself, which I still keep in my original Stingers folder. Here is my Stingers resignation letter, word for word:

Dear Current and Future Stingers,

This is a letter to inform you that I am resigning from the position of President and will no longer be an active member of the Stingers.

I have spent many hours thinking about this decision and feel that this is the best recourse for me to take. The reasons for this are far too many to describe in a few paragraphs but I want to give you just a taste.

Many of you may not know, but I ended up last semester with a very bad case of pneumonia and I was not able to take my finals. This ended a semester in which I was very unhappy and had no time to take care of myself, mentally or physically. This is the foremost reason I am leaving, to focus on taking care of myself, and to plan for my rapidly approaching future.

All of you know how difficult last semester was for the group. Central to the problem was my trying to lead a group that was not what I had desired or envisioned. I want to leave behind a brief description of what I thought the Stingers would be:

The Stingers would be a trombone group in the tradition of the a capella groups on campus. The idea was basically to take their idiom and apply it to a trombone. Popular music would be 99% of the focus. The group would occasionally play with a rhythm section. The pieces would be memorized (eventually). The group would be entertainment-geared – not just music. The group would be loose and fun. 

Unfortunately for me, the members that are in the group now do not have the same vision as I do, and this is the main source for most of the conflicts that have led to my decision. I leave this description behind in the hopes that someday my ideas will come to fruition. One only needs to look at the first sentence of the description to understand my idea. I still and always will feel that it is an excellent idea.

I care very much for the group and urge the group to forge ahead in whichever direction you may choose. I will make myself available to help in this transition period. The Stingers must build on their strengths and continue to entertain the U of R community. Keep the traditions going – the Slide Show, the scrapbook; these are all good things.

It saddens me to say goodbye, but the time has come to pass on the torch, so to speak. I will have many good memories of what we have all built from scratch, and the individuality of each of you.

I want to leave you with the philosophy that I started the group on from day 1. I would rather see 6 enthusiastic, committed members in the group than 12 mediocre-committed members in the current and future Stingers. Remember that always, and never settle for mediocrity.

Sincerely yours,
Matt Douglas

If you’re the founder of a group or company, one of the hardest decisions that you’ll ever have to make is to know when it’s time to walk away. If you’re currently in this situation, I encourage you to spend a few minutes literally looking and talking to yourself in the mirror. Be honest. Is it time to walk away? If you’re no longer part of the solution, you’re likely part of the problem. Know thyself.

©2024 Matt Douglas