Greg Scheinman, 52: The Midlife Man

What is important to you? What is really important, and what is your vision of it for your future? It turns out that doing less, and doing it better, is part of how we get there. For so much of life, we can end up just churning: lots of action but very little real movement or purpose. Greg Scheinman has walked the talk about how to change his life, how to understand what is of value to him, and to only focus on the things that he feels will bring him life satisfaction. But this wisdom has been hard won, with the big learnings coming from failure and pain. 

He believes that to lead others, it is less important to tell than to show. He feels that if others see him doing something, it can open a window of imagination of what could be possible for them. His focus is singular: midlife men—although, unsurprisingly, about a third of the inquiries he receives are from women…who are looking to find help for the men in their lives. 

How old are you?
Fifty-two.

Where are you from and where are you currently based?
Born and raised in Great Neck, Long Island; college at the University of Michigan; and living in Houston for 23 years (where my wife is from). 

Are you married? Kids? 
Married going on 25 years to Kate, and we have two sons: Auden, 21, a junior at CU Boulder in business school, and Harper, 18, a senior in high school who will be going to Loyola Marymount University in Los Angeles for graphic design next year.

What is your mission with “The Midlife Male”? 
To help men live happier, healthier, wealthier, stronger, longer, and have more fun in middle age. I call it “mastering the middle”. The middle is messy, but it’s also the sweet spot. I’m really just trying to take all that I have learned and continue to learn and share it with as many men as possible so that they can make better choices in life. Because, when you make better choices the majority of the time, the majority of your life gets better. It’s that simple.  We’re doing this through our weekly newsletter, podcast, community and retreats. We have overcomplicated and over-indexed so much as men and there’s been so much negativity around midlife and masculinity in general that I just want to flip the switch on all of that. We have this opportunity to stop seeing aging as something to fear and start seeing it as something aspirational.  

What were you doing before? 
In my 20s I was in the film business and produced a few independent films that if you’re up late enough at night or browsing Netflix you can find. In my 30s I started a children’s sports video company called Team Baby Entertainment; we were kind of the baby Einstein of the sports world and went from selling DVDs out of the trunk of my car to selling the company to former Disney CEO Michael Eisner. I then bottomed out, personally and professionally, struggled with imposter syndrome, alcohol, my health, confidence, money, and didn’t have another big idea; so, I did the opposite of what everyone thought I was going to do and went into the insurance business. I became a partner in a firm, which grew to over 200 people and was acquired in 2020, and I cashed out and was pretty much shown the door. 

Why the change? 
I was unhappy for too long. What I found was that chasing authenticity where authenticity doesn’t exist is exhausting…. And I was exhausted. I needed to redefine and redesign what success really was. I was good at whatever I did, and from the outside looking in, everything was great, but I didn’t feel that way. So, when COVID hit and we’re selling the firm, I was 47 years old—the same age as when my father had passed away—and reached this tipping point where I could either get my sh-t together and make the next phase of my life my best phase, or I could squander it all. Which one sounds better: one or two? The answer’s obvious, and now I ask myself that question every day. We all know the right answers. It’s doing it that’s hard. That’s what I focus on now. Doing less, better and with more focus. So I went on a three-year journey to interview the highest performing middle-aged men in the world and find out how they were living, what they were doing, and asked them to share their wisdom and experience with me. Then I applied what I was learning, wrote about it every week, and these interviews and newsletters became my book. I was able to develop my five rules (find these in my book and my FREE “How to maximize midlife guide” that you get when you subscribe to our newsletter), 6 F’s (family, fitness, finance, food, fashion, + fun), and one question to transform my entire life by the time I turned 50.    

What are Greg Scheinman’s goals? 
I actually don’t have goals per se. Yeah, there are things I want to do, reach, and achieve, but I’ve learned to set standards over goals. If I adhere to my standards every day, then whatever goals or metrics for success, happiness, health, wealth, and for my family that I have will be inevitable. I have what I call my Midlife Action Plan (MAP), and it has everything laid out in detail: my standards for each area of my life; what I put on my body, in my body, earn, where and how I spend my time. So all I really have to do is wake up each morning and follow it. I’ve now written these with hundreds of men. It’s interesting—with guys, you can ask them for their business plans, KPIs, quarterly reviews, accounting reports, and pretty much anything business related and they can whip it out. Ask them for their life plan, and they don’t have one.  

How do you reframe someone’s view of midlife and make them optimistic about what can be?
You can’t just tell them. That’s why I’m really not into all the motivation and woo-woo that’s out there. You have to show them—in real life and in real-time. Live and lead by example. And you need to be relatable, credible, and then you can be aspirational. They need to feel like what they’re seeing is not only possible for them, but highly probable. I’m 52, a husband, father, have businesses to run, tuitions, cars and a mortgage to pay for; so, if I can do it, so can they. I’m not remarkable in any way, and I don’t say that to be self-deprecating but, rather, to show that yes, you can prioritize your health, family, climb a mountain, make new friends, pick back up that hobby you put down 20 years ago because I’m living proof of that. I wasn’t doing half the stuff I’m doing now in my 30s and much of my 40s; and while I love and get to do a lot of public speaking now, what’s most effective is the actual doing and the showing, not the telling. Plus, it’s much more fun. 

Do you have a different coaching approach for men in midlife versus women in midlife?
I only coach men. Everything I do is for midlife men, by midlife men. This is who I am and what I know—not trying to be everything to everyone or be shallow and wide. I prefer to be narrow and deep. I want my coach to be a man who’s older and wiser, has older kids, more money, better health, etc. so he can help me see where the puck is going. Same for my trainer, nutritionist, financial advisor, etc. My team is composed of people who are ahead of me.  The men I coach are accomplished, and we’re all very similar. What’s interesting is that around 30% of the inquiries I receive and subscribers we get are midlife females. They want the men in their lives to be better: their husbands, fathers, ex-husbands who they have to co-parent with for the rest of their lives, work colleagues, etc. They want to help; they’re interested, engaged, and open-minded. While I only coach men, and Midlife Male is a lifestyle brand for midlife men, so much of our content, principles, and stories are not age or gender specific. There’s a lot of value for everyone and I hear that a lot from women and younger men, and I really appreciate it. But yes, our community, retreats, and my clients are men 40 to 60-ish only. 

What are your thoughts on retirement?
I used to think about retirement all the time when I was going through the conformity, complacency, and redundancy of corporate life. Now, I don’t think about it at all. I feel like I’m just now getting warmed up and finally operating at the intersection of personal passion and professional expertise. This is the hardest I’ve worked in my life, but it’s filling my tank rather than draining it. I define wealth as getting to do what I want, when I want, with who I want, for as long as I want and I’m almost there, so why would I stop? I was lying in bed with our son the other night—we’re very lucky that he still likes to come downstairs, climb onto our bed and watch TV with us—and I showed him a message I’d just gotten from a guy that I’d reached out to asking to interview him, and he said yes. This is a man very different from myself, which is what makes him interesting to me, and I was telling our son how grateful I feel now to get to do what I’m doing and that we attract and repel exactly what we deserve. As I’ve changed my life, and he’s old enough to have seen what I’ve gone through, all these amazing new opportunities and people have come in. I don’t know if I believe in retirement anymore because there’s always something I want to be working on. There’s a quote I love that says, “You don’t stop playing because you get old, you get old because you stop playing,” and I have it printed on the back of my stationery as a reminder. You may retire from being the CEO of your company, but you’ll always be the CEO of your own life. 

From speaking to all of your incredible guests on your podcast, what is one piece of advice or wisdom that sticks with you?
Slow down. Run your own race. Slow is smooth, smooth is fast. What sticks with me about all these guys is that they never seem to be in a rush. They’re never frantically multitasking. They’re present. They’re intentional. They have a rhythm and cadence that instills confidence. I really aspire to that. I’m not naturally wired that way.

What does a day in your life look like?
I’m up at 6 a.m. every morning without an alarm clock. I joke that my morning routine is “hydrate, urinate, caffeinate”. I then read, write, and do outreach. Next, I work out around 8 a.m. I do three personal and three professional things per day. That’s it. I’ve found that to be my bandwidth. I write them down each morning. I’m like a golden retriever—throw the ball and I’ll bring it back—so I need to know what to do, and I’ll do it. Most days, the three personal things are exactly the same: walk my dogs, workout, sauna/cold plunge. My work day is 10 to 4. I write the newsletter on Mondays and keep most of my open meeting space on Monday, see clients on Tuesday through Thursdays, and record podcasts and speaking business on Fridays. I work from home now, so I take frequent breaks throughout the day. We aim for family dinners three times a week, as our younger son is a senior in high school. I’m usually in bed by 9 and asleep by 10. When I’m traveling, I try to keep as much of the same routine as possible. 

What’s your diet like?
I don’t diet. For me, nutrition is a lifestyle. I don’t count calories or macros or restrict myself of anything if I really want it. I keep it 80/20: 80% of the time I eat clean (chicken, fish, steak, fruits, vegetables, good carbs and fats, eggs, greek yogurt, rice, lots of water). My wife is an amazing cook, and I pretty much grill everything. I don’t drink alcohol anymore. I do like non-alcoholic beer now, which I never used to. The other 20% of the time, I’ll eat what I want. I enjoy those In-N-Out burgers and pizza dates with my sons.  We bought this Ooni pizza oven and it’s a game changer. We make healthy pizzas now all the time. I take 5 grams of creatine, a multivitamin, omega-3s every day. I’ll also have protein shakes during the day. I get my bloodwork done every 90 days so I know where I stand. I eat a lot for my size, and if you follow me on Instagram, you’ll see most of my meals.  

What about your fitness routine?
I’m 5’9, 175 lbs. and <10% body fat. I want to feel good, look good, and perform well. So, I reverse engineer back from that. I train five times during the week, three weekdays and both weekend days, for around 60 to 90 minutes. Personally, I find it easier to train on weekends so those are my harder workouts. I lift weights three times a week, mostly using an app called LADDER. I box every Friday with a trainer and use an app called ErgZone for much of my cardio, as it’s non-impact using rower, skier, and bike. These days, I also walk/ruck frequently and do yoga. I go on feel, so when I need more rest days or variety, I just adapt. Sundays I have a group over and we train in my garage gym and backyard. It’s something I really look forward to. I’m more focused on sustainability and longevity, so I see a physical therapist weekly and do a lot of mobility exercises pre-post workouts. I enjoy physical experiences and have done the 29029 Everesting challenge the past three years, HYROX, and walked 52 miles for my 52nd birthday. I’m also very transparent that I started on TRT at 49.  

What are your 3 life nonnegotiables?
My family, my fitness, and my finances. If I had to pick a fourth, it would be fun—because what’s the point of any of this if we’re not enjoying the ride? 

Connect With Greg:
Midlife Male
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