Greg Scheinman on Breaking Out of the Midlife Blues

You can be successful without feeling happy or fulfilled. You can achieve a meaningful outcome without being able to simply pause and enjoy the moment. And outward appearances can signal that you have it all figured out, while internally you can find yourself feeling like the best years are behind you.  

For those of us who are achievement-oriented, we’ve probably experienced all of these feelings at one time or another. I’ve shared my own challenges with mortgaging my joy for the illusion of happiness on the other side of achievement, only to feel let down or immediately return to the pressure of another self-imposed expectation of another desired outcome.

That’s precisely why I so thoroughly enjoyed my initial conversation with Greg Scheinman on his podcast, and reached back out for a followup conversation. Greg is the founder and CEO of Midlife Ventures and the online website, podcast and newsletter Midlife Male. He’s definitely a kindred spirit and his insight is now a source of inspiration to millions! 

“I found myself at 47, the same age as when my father died, really struggling for who I was. As a husband, as a father, as a provider, I wasn’t taking great care of my health,” Greg told me recently. “I was over-indexed at work. I had chased the salary-title-success thing for all it was worth, and the ROI or, as I say, the ‘return on life,’ really wasn’t there.

“I wanted to change how I was going to operate,” he continues. “I could either squander these opportunities and effectively lose my life, like my father did. Or I could pour rocket fuel on it and make this next phase of life my best phase.”

Greg is a performance coach, best-selling author, and speaker on life after 40 and personal transformation. He’s a multi-time founder and CEO, including of Team Baby Entertainment, which he sold to former Disney CEO Michael Eisner. He has enjoyed success — and learned how to find purpose beyond fleeting achievements.

Embracing Who You Are

Nobody wants to look stupid in front of other people. But when we live this way, trying to avoid something bad, we enter a cycle of fear and fakeness. As Greg puts it, “Chasing authenticity where authenticity doesn’t exist is exhausting.”

When we’re frozen by fear, we don’t act with conviction. We don’t live according to our values, we don’t chase our dreams, and we fail to live authentic, fulfilling lives. The alternative, as Greg discovered, is to gradually embrace who you are.

“I said to myself that day, ‘What would happen if I just started making the better decision the majority of the time?’” Greg says. “What would happen if I just started trusting my gut a little bit? And if I started making the better decision the majority of the time, my belief was that the majority of my life would start getting better.”

This doesn’t require a massive reinvention or a public declaration. All it requires is believing that you can start to be yourself and become better, a little bit at a time. No matter where you are in your life. “It’s a constant work in progress,” Greg says. “And you have to start embracing and enjoying that process.”

The Power of Community and Connection

Community and connection are two areas I’ve deliberately focused on in recent years, including through my work with ImpactEleven. There’s no limit to the ways in which you can enrich your life through your community — work, family, faith, hobbies, and more. The important thing is cultivating a variety of healthy relationships, especially as we enter midlife. 

Unfortunately, too many men are struggling in their relationships and in their health. They’re feeling badly about their finances and about their relationships. (And they may not have that many relationships. Thirty years ago, most American men had at least six close friends. Now, half as many men have six friends, and 15 percent of men have no close friends, up dramatically since 1990.) 

The pressure to conform amplifies these struggles. There’s a certain way you’re supposed to live your life: go to the right school, get the right job, and start a beautiful family with kids who go to the right schools and get the right jobs. 

“The next thing you know,” Greg says, “you wake up 5, 10, 15, 20 years down the road. And you’re like, ‘How did I get here? This is not what I thought it was going to be.’”

Social media doesn’t help. It’s all too easy to look at what everyone is posting on Instagram and feel like we’re failing, that we can’t possibly live up to what our peers seem to be accomplishing. 

Greg has literally created a community to address this crisis, along with a book, website, podcast, and more. “The mission is to stop seeing aging as something to fear, and start seeing it as something aspirational,” he says. “Stop thinking and living like our best days are behind us and start living and acting and loving like they’re in front of us. Because they are, you know, lifetimes.” 

Embracing the Middle as the Sweet Spot

There are 53 million middle-aged men in America. That’s a massive audience looking for help, hoping to see that there’s so much more to achieve and enjoy. “We are going to change the way midlife is looked at so you can stop seeing midlife as a crisis and start seeing it as an opportunity,” Greg says.

This statement reframes how we think about midlife from a downside to a chance for growth and reinvention. Midlife is your halftime reflection. It’s your time to strategize, to decide what you’re going to do with the rest of your life and how you’ll measure success. 

“When you come out of that locker room for the second phase of your life, you have to have a plan, what I call a ‘midlife action plan’” or MAP, Greg says. “And if you don’t know where you’re going, you are never going to get there.”

This message isn’t coming from a guy who’s unfamiliar with life’s ups and downs himself. He has experienced alcoholism, anxiety, and depression. Greg’s message is that you can start from wherever you are. He started from a feeling of being stuck, even though on the outside, it looked like he had an ideal life. “I was in the messy middle. But the middle is also the sweet spot that I found,” he says. “And it’s like, how do we clean up some of the mess? And how do we ultimately master the middle?”

How You Can Embrace This Moment

Greg’s story is a powerful lesson that every phase of our lives is a powerful opportunity, especially midlife. I’m reminded that we can sometimes over-index on that one key relationship, whether that’s our partner or our family of origin. And we‌ miss out on being inspired by people who are like-minded, who can push us forward and hold us accountable. 

At one point in my life, I was missing that connection. I was hungry for it. And now that I have those connections, I couldn’t imagine living without them. So if you haven’t found what you’re looking for yet, don’t lose hope.

As Greg reminded me, “Anything and everything you want is possible. It exists. And it’s highly, highly probable that you’re going to be successful when you find what works for you. You are not an outlier. You are not alone.”

Read More personal growth

And join our email community to receive bi-weekly insights with actionable tips and videos, new research, and inspiration and ideas for cultivating growth in business and life.