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You’re Not Having Enough Fun (And It’s Your Fault)

Here’s the truth: fun doesn’t schedule itself. If you are not intentional about it, it doesn’t happen. I learned this the hard way. These days, I treat fun the same way I treat fitness, finances, family or any of the other 6Fs. It gets the same level of planning and priority. In fact, this topic is exactly what I talked about with Chip Conley on his podcast earlier this week.

On Monday I joined Conley, an entrepreneur, best-selling author, and founder of Modern Elder Academy, on his show The Midlife Chrysalis. Chip was one of the first men I reached out to six years ago, and he was gracious enough to guest on Midlife Male. Now he has launched his own podcast, and as far as I can tell, I’m guest number 19.

Looking at the list of guests before me - Rich Roll, who inspired me to change my life at 47, Sara Blakely, married to my midlife male man-crush Jesse Itzler, Scott Eastwood, son of Clint, Maria Shriver, John Mackey - it is validation that my work is being noticed. That feels good.

I have never been great at accepting compliments or feeling worthy, but I am getting better. I may not be as famous as Rich Roll or have sold as many books as Chip… yet. But I deserve to be in the conversation. My life résumé holds up. In many ways it is more relatable, credible, and aspirational. Men can see themselves in me, and I in them. I have done the work. And I am not close to done.

And neither are you.

Applied Wisdom

Here is one of the biggest lessons Chip and I discussed:

Success in midlife does not come from the acquisition of wisdom, it comes from the application of it.

Once I started setting personal standards, living with intention, and treating everything, including fun, with purpose and process, the payoffs got better in every area of my life. That is what I want to talk about today, using a recent trip of mine as an example, because it’s proof that having fun happens by design, not by default.

Doing Vegas by Design

Last week Kate and I were in Vegas to see The Eagles perform in The Sphere with tickets we bought over a year ago (planned, intentional fun, like I said). We booked a suite at the Palazzo in the Venetian because it is connected to The Sphere and we could walk right in without even stepping outside. It had been nine years since I was last in Vegas. 

I even Googled “How to tip and get an early check-in and upgrade” and followed the advice to a T. I prepared my $50 bill, waited until a host called me over, casually placed the fifty on the counter, not trying to hide it in any way, just left it there. I called the host by her name and smiled, asked if it would be possible to check in early and if an upgrade would be available, then I remained silent.

Noticing the bill, she asked me if I wanted change. I said no. She said thank you, took the bill off the counter, and told me she had our upgrade available with a great view of The Sphere.

I make all of our reservations in advance. Fun is in the planning. I scoped out all the restaurants in the hotel and nearby. We went to Milos for lunch Thursday, enjoyed the adults-only pool with no interest in crowds or loud music, Gjelina for dinner, and after dinner I lost $300 in about three minutes at the blackjack table where I sat down, proceeded to lose every hand, and reminded myself why I no longer enjoy gambling. Back in the room by 10 p.m., we spent a good 20 minutes just looking out our window, mesmerized by the moving images on The Sphere that rotate 24/7.

Wake-up is always 6 a.m. no matter where in the world I am, so Kate and I grabbed coffee, a light breakfast outdoors, and then walked the Strip for a few miles. This is the only time I will do that, when it is empty. There is a Canyon Ranch spa at the Venetian, so we went to the gym, followed by a facial for Kate and a stretch session for me. Showered and hungry, we went back to Milos.

Pool in the afternoon. Gjelina again for dinner. Then The Eagles at The Sphere, the most impressive venue I have ever seen. The highlight was Deacon Frey, Glenn’s son, singing Take It Easy in tribute to his father. As someone who lost his own father too young, I teared up.

I do not drink anymore. My vices are working out, coffee (now decaf), and the occasional mild THC gummy. This was the perfect night for it.

Why Fun Takes Work

Routine is fun. Discipline is fun. Planning is fun. Executing is fun. Having fun is work. And that is what men often overlook. I tried the opposite. For years. It was no fun. 

One theme in my coaching practice: men are not having enough fun, do not know how to, and struggle to bring it back. I want to fix that.

Road Trip to LA

It was our son’s birthday on 9/8. He is in Los Angeles, so naturally both Kate and I were like, “Road trip!”.  I planned it so that we would rent a Mustang convertible and drive from LV to LA via the iconic Route 66. While our Mustang was a 2025 and not a 1965, it sufficed. Photo op achieved, top back up.

We rolled into LA by 2 p.m. and picked up Harper. Could not be happier. He is tan, looks great, extremely happy, and settled in at school. I just love that kid. He wanted Stüssy clothing for his birthday and Jon & Vinny’s for an Italian dinner. Done and done.

Sunday we drove up to Malibu, but not before I got up and took an Orangetheory Fitness class. Are they the best? Far from it. Does it matter? No. I do the best I can wherever I am. This worked.

Fits: Alex Crane T-shirts, Levi’s vintage denim, Buck Mason chinos, New Balance 1906s, Havaianas flip-flops, Buck Mason blazer, Tom Ford glasses, Ray-Bans.

PCH up to Malibu, lunch at the Country Mart. Celebrity sighting: Howie Mandel and I both bought the same Double RL pants.

Back in LA, Kate booked massages at Den Mother. Robes, garden, fire pit, head-to-toe treatment. Then dinner at Gjelina again. Burrata pizza, cacio e pepe, chicken. Always great. Sit out back if you go.

Stayed at Hotel June. Sister to The Proper. Loved The Proper, but not paying $900 a night. Marriott points covered The June, one mile from Harper’s dorm. Perfect.

Back to Work, On Purpose

I booked our flight home late afternoon so I could accommodate my normal Monday MLM team call and the podcast appearance with Chip. I knocked out both, Kate went for a long walk, Harper had his morning classes, and then we picked him up for our obligatory lunch at In-N-Out Burger. My order is always a “Triple Single”: three burger patties, one slice of cheese. I pass on the fries.

As I write this I’m sitting in my usual 8C, what I call “poor man’s first class,” the aisle seat, first row right behind first class on the flight home.  Best seat on the plane, in my opinion. 

I used to fly home from trips and vacations feeling guilty, re-counting every dollar we spent, believing that the office and clients couldn’t survive without me, and worrying about the insurmountable amount of work that’s waiting for me when I got back and that I was being judged by colleagues and partners for taking time off in a world that rewards 24/7 hustle and grind.  In fact, I used to not take vacations or getaways much at all. 

I don’t live like that anymore. 

This is life by design, not default. I live my message with a clear heart and mind. I plan fun with intention.

This is what turning your F’s into A’s looks like. This is maximizing midlife.

It is not about the biggest or the most. It is not about tomorrow or excuses.

Do not be afraid to spend money on traveling and having fun. Be afraid of growing old and realizing the only place you ever went was to work.

In the short term, people regret their actions more than inactions. But in the long term, the inaction regrets stick around longer. – Tom Gilovich

Think about it.

In Health (and fun),

Midlife Male
52. Husband. Father. Entrepreneur. Coach. Student of the game.
Still walking the walk.

P.S., HERE ARE THREE WAYS I CAN HELP YOU TODAY:

1. Get One-on-One Coaching with me. Want more help? I coach a select few men one-on-one. It’s just you and me, talking it through, making a plan, and pushing you toward your next win. No pressure, just progress. Reach out—let’s make it happen, one step at a time. Book your call here.

2. Buy my bestselling book: The Midlife Male: A No-Bullsh*t Guide to Living Better, Longer, Happier, Healthier, and Wealthier and Having More Fun in Your 40s and 50s. Order the book here.

3. Book me for a speaking event: Looking for a speaker? I have helped hundreds of organizations and individuals who want to perform better, feel better, and get more out of their lives and careers. Contact me here.