The challenges and opportunities of midlife can be surprising. Some see this time as one of crisis, some see it as an exciting new chapter, and many find themselves faced with circumstances that they hadn’t planned for. Author and entrepreneur Matt Ross hopes to help fellow midlifers navigate the journey.
Ross worked in New York City radio before pivoting to the education space, where he transformed music education company School of Rock from a five-location startup into a worldwide powerhouse and founded art-centric One River School, now operating across six states. His new book, “Grow or Fold: Transform Yourself in Midlife and Beyond,” draws on both his business experience and the realizations he came to while navigating the many personal challenges of midlife.
The Epoch Times: Many people are surprised by the challenges that pop up in midlife. What misconceptions have you found that people have about this stage of life, and what are they often unprepared for?
Matt Ross: I think people get so in the weeds on all of the day-to-day obligations and challenges that they stop working on having a clearly defined long-term plan for themselves. Then they often wake up, unprepared for the future and frustrated that the clock is starting to tick.
The Epoch Times: In a recent talk you gave at WILDx, you pinpointed the common experience of “a midlife moment,” a sort of fork in the road at which one might “grow or fold.” What did that moment look like in your own life and how did you recognize it for the pivotal moment it was?
Mr. Ross: At 50 years old, I was struggling with a multitude of very complex issues, none of which were the result of my doing. All four of our parents were dying and declining, I was having health issues, my two older brothers were lost to addiction, I sold a business and was out of work, and my 16-year-old nonverbal son with autism was institutionalized. This was my grow or fold moment.
The Epoch Times: When you realized that you needed to take action, what was the first practical step you took that began to make a difference?
Mr. Ross: I had a novel idea: Treat myself like a business. I had always been really good at creating vision and strategy for companies, but never really applied that same skill set to building a short-term, mid-term, and long-term plan for myself. This process allowed me to step back and create my vision plan with 10 goals for 10 years and then to get into the trenches and start to deal with the most critical issues first to pave the way to work on long-term things.
The Epoch Times: You’ve enjoyed a successful career in business, specifically focused on music and art education. Did you find that your entrepreneurial talents or creative passions benefited you through navigating your midlife moment and beyond?
Mr. Ross: Absolutely. The benefit to me was that I had always built a very resilient sensibility. Entrepreneurs often look at problems as opportunities redirected. Once I was able to treat myself like I was a business, then it was about doing all the things I was trying to do and relying on my instincts.

Courtesy Matt Ross
The Epoch Times: Looking back, how is your life different now from your “midlife moment”?
Mr. Ross: It’s going to sound really strange, but I’ve never been happier and it feels even weird to say that. I have the life I’ve always dreamed of at 65 years old and the battle scars to show that I fought the fight in the trenches. I didn’t come for money, and I had a dysfunctional household, but God blessed me with some intuition, street smarts, work ethic, and perseverance. As I reflect on where I am, I couldn’t be more proud.
The Epoch Times: Is there anything you wish you would have known earlier about the midlife years?
Mr. Ross: Yes. Slow down. Ask more questions. When I was stressed out, I spent a lot of time worrying and didn’t know how to turn the switch off. I would’ve gotten some more assistance earlier from mental health professionals and others to help me better understand how to work on the challenges I was facing and to deal with the uncontrollables.
The Epoch Times: What do you believe are the keys to thriving in this season of life?
Mr. Ross: We’ve got to dream a little bit. We’ve got one life to live—what do you want it to look like? It starts with framing where you are by taking inventory, understanding where you want to get to by dreaming and building a vision plan, and then creating a strategy to achieve it.
The Epoch Times: What do you hope readers take away from your book “Grow or Fold: Transform Yourself in Midlife and Beyond”?
Mr. Ross: That the life that you want is achievable. It comes down to taking personal responsibility, becoming truly self-aware about who you are, what you’re good at, and where you need help, and then building the plan to maximize your health and happiness. The gap between fair and good is small. The gap between good and great is very large, and if you want a special life, you’ve got to be willing to put the time and effort into the planning process.







