When I sat down to write this week’s newsletter I realized I’d left my notebook upstairs in my office. So I ran up to get it, as it contains all my ideas and thoughts from the week.

I grabbed the notebook and turned to head back down. As I did, I caught my 1989 Fender American Telecaster looking at me, as if it was saying “Play me.”

I felt this gravitational pull between my notebook (“work”) and my guitar (“play”), and for a moment I was conflicted.  It was 2 o’clock on a Wednesday, I had a flight out the next night, and there was work to be done. Now’s not the time to be taking a guitar break.

Except that, well… It was exactly the right time for a guitar break.

What I needed was 15 minutes sitting on that stool, Fender twin amp on stomp, tele in my hands and noodling on some bluesy riff that I’ll never get quite right. The more I muck it up, the better it actually sounds.

I’ve learned that the happiest times, most content times and most creative times often turn into the most productive times, because you’re giving yourself what you need.

This is not to be confused with allowing yourself to become distracted, loss of focus or even laziness. Instead, it’s giving yourself permission to lean into those moments where you can recharge, refresh and re-align your energy.

I also don’t have anything to prove. That’s a relatively new revelation.

I spent a lot of time thinking I did. That I had to prove to everyone but myself that I was successful.

“Look at me.”

“See what I’m doing, where I’m going, who I’m going with, what I’m making, lifting, eating, wearing…”

The irony is that I still showcase that all week long, but now it’s not because I’m trying to prove anything to anyone. What I’m meant to be doing is not only reflecting on my life in middle age, but also documenting my experiences as they come.

I want to challenge myself and other men on the notion of what success looks like.

What I see most is conformity, stagnation, anxiety, self-induced stress, poor health and all these things you’ve acquired that you’re attached to, but don’t actually need.

The truth is a lot of the men I hear from have “won,” but they don’t realize it – and they’re certainly not living like it.

I was one of them.

It’s gotten me thinking quite a bit about ambition.

On ambition

Men are often ensnared in a relentless pursuit dictated by society’s traditional yardsticks of success: higher salaries, prestigious titles and notable achievements.

However, midlife is a unique time to reevaluate what ambition and success truly signify and how we can redefine these concepts on our terms, especially men navigating the complexities of aging, without succumbing to the fear of societal judgment.

The conventional paradigm of ambition has long dictated a narrow path to success, marked by external validations of wealth and status.

Case in point: Last week, The Wall Street Journal ran this article that was sent to me by 16 different men!

These Professionals Aren’t Retired, They Just Have Zero to Prove

To know whether how you perceive yourself is different from how you’re perceived by others, pay attention to what people send you, invite you to, don’t invite you to, talk to you about and choose to share with you.

In this article, we find compelling examples of high-performing men who have courageously stepped off the beaten path. These men have embraced an ambition not measured by their bank accounts or job titles, but rather by their happiness, fulfillment, and the delicate balance they maintain between work and life.

Their stories not only challenge the traditional metrics of success but also highlight a profound shift towards an ambition rooted in personal growth, self-discovery, and the pursuit of joy.

Stop associating ambition with “more”

Achieving more, having more, earning more, going after more. That’s what an ambitious man does – or so we’re taught.

But isn’t it equally ambitious to pursue total life wellness? To ambitiously chase doing less? To ambitiously maximize middle age, whatever that may look like to you?

The men featured in the article came, saw, conquered and moved on.

They knew when to say when.

They achieved their earlier ambitions in life, pivoted their ambitions to a much different metric for what success looks and feels like going forward, then ambitiously committed to living in that new way.

That takes an enormous amount of what Dana Cavalea calls the 3 C’s: clarity, conviction and confidence.

True ambition, particularly as it pertains to men in midlife, is an inward journey that transcends the materialistic accolades society often highlights.

It’s about aligning with one’s deepest values and desires, and having the audacity to pursue this personal vision of success.

This redefined ambition isn’t about lowering aspirations but about recognizing that the pinnacle of achievement lies in leading a fulfilling life—a life that reflects one’s truest self, not the expectations imposed by others.

Let ambition look different in middle age

Updating your midlife ambition shouldnt be frowned upon as making you feel any lesser of a man.  If anything, we should be praising, encouraging and supporting it. More often than not, men feel trapped to stay in jobs, careers, and the hustle and grind for far too long, only to end up with regret.

As I read the article I found myself nodding along. Yup, I get it.

There was the guy who left Wall Street, cashed in his chips at 44 and now gets to surf hundreds of days a year. The entrepreneur who exited and now gets to climb mountains in Colorado as often as he desires.

Outside of the men in the article, I’m working with a real estate executive. We’re planning his gap years now, as his kids are seven and nine years old. He no longer wants to or needs to commute to NYC every day to run his business.  He’s financially in a position to step away, reframe the quantity of deals he wants to be involved with and increase the quality of time he wants to spend with his wife and kids.

Another client sold his equity in his firm and moved with his wife out of NY and down to Florida.  With both kids in college, he was able to generate significant income from renting his NYC apartment and is able to happily rent a condo, walk to get coffee every morning in the sunshine and enroll in culinary classes.

Ambition is just as much about what we need to stop doing as it is about what we need to start doing and keep doing. It doesn’t always have to be extreme, either.

Midlife is a time for men to reassess their priorities, to recognize that genuine success is not quantified by societal benchmarks but by personal satisfaction, meaningful relationships, and contributions to the world. 

Let’s redefine ambition not as a pursuit of external validation, but rather as an endeavor to live authentically, rich in experiences that bring genuine joy and fulfillment.