Friends,
Like all of us, I’ve been on a journey the last two years. And I’m overdue on updating many of you on what I’ve been up to.
The pandemic marked my transition from gigs in menswear journalism and copywriting into life coaching. In January of 2020, I was able to transition to coaching men full-time, and establishing my practice has been a wild and rewarding adventure. I have worked with over 150 guys individually and in groups since then.
In hindsight, men’s coaching seemed like the next logical step in my evolution: I’ve always liked helping men live better lives. It’s how I ended up penning articles and essays for men’s mags like GQ, Esquire and Men’s Health. And now, with coaching, the veneer of the page is removed: I’m actually sitting one-on-one with men discussing their challenges, hopes and dreams.
Coming from a fashion background, I noticed early on that I tended to attract a certain clientele as a coach: Guys just like me. We were all perfectionists, all meticulous with our appearances, from our haircuts to our wardrobes to how we decorated our homes. We looked good. But behind the facade, our lack of self confidence was holding us back from being the men we knew we could be. We usually required a lot of external validation: from work, from women, from our social media followers - just to stay afloat.
In my men’s groups, we started calling ourselves “nice guys,” after the codependent male archetype Robert Glover coined in his book No More Mr. Nice Guy. But that name always fell short for me. It didn’t reveal the whole picture. Recently, I started calling us Gatsbys after Jay Gatsby in F. Scott Fitzgerald’s The Great Gatsby.
Not many here will need an introduction to Gatsby’s character, but he’s a wildly charming, successful, but insecure man who overcompensates for his anxieties by flexing… hard. Gatsby’s sense of grandiosity spawns from a fragile masculinity — he doesn’t know who he is as a man. And because of that, he keeps others at arms’ reach. Daisy, a woman, gets the closest. But she still doesn’t know him at the end of the day.
As a writer for GQ at the onset of the blog generation, I was on the front lines for the largest coming out party of Gatsby-like men the world has ever seen. Thanks to menswear blogs, the surging popularity of stylish shows like Mad Men, and the launch of Instagram, lifestyle-conscious guys were given license to peacock in a whole new way.
And peacock we did. In fact, a whole universe was created on the internet for guys to show off various impressive, niche corners of their lives: from sneaker collections to tattoos to bespoke suits to tricked out camping vans.
In my opinion, the internet men’s lifestyle boom just shined a spotlight on an epidemic that has been gathering force for generations: Modern men — due to a combination of factors that include a lack of quality father energy, and widespread societal confusion about what a healthy, whole man is — tend to lack a strong inner structure. We don’t know who we are. And “the more fragile a man feels internally,” writes Jungian analyst Guy Corneau in Absent Fathers Lost Sons, “the more likely he is to try building an outer shell to hide this fragility.”
Impressive outer shells are fetishized in our culture: who didn’t want to be Gatsby? (Or Leonardo DiCaprio for that matter?) Or [insert favorite athlete, rapper or rockstar here]. Who didn’t want to be the boy with the toys?
Toys are fun. But the race to build our outer, Gatsby shells has its setbacks. First is the rising cost of living, and that to flex harder means to grind harder, too. I read recently that the average age of burnout for a man is 32 years old! And so much of that statistic is thanks to the chase many of us are on to keep up with a constantly moving goalpost.
Another major setback to building an impressive outer shell is loneliness. As Gatsbys, we tend to think our enviable lifestyles will bring us more love and connection, but I’ve found it’s the opposite. We’re so determined to project a certain image of ourselves, that we rarely drop our guard enough to let anyone - even our closest loved ones - past the impressive gates. Sure, our lives look great on the outside, but inside we end up living those "quiet lives of desperation” Thoreau wrote about.
Lastly, there’s the issue of attachment: since our self worth is reliant on external factors, we become beholden to things beyond our control. Should we happen to lose what is propping us up - whether that’s a job, a reputation, or a relationship - the fall can be tragic. I watched my father go through this fall after his second divorce, and it ended in his suicide.
In our most honest moments, Gatsby men feel pretty trapped. But admitting that goes against everything we’re trying to portray: that our lives are, in essence, booming. We’re killing it. Crushing on every level. Having a grand old time. But for Gatsbys to heal, we have to risk being intentionally unimpressive.
We do this by coming out from behind our shells and showing other people who we are at our cores. Maybe we’re scared, maybe we’re unsure, maybe we’re sad, or lost, or pissed off. Whatever we’re feeling, it’s precisely the moment we begin to get real about our insecurities, our fears, and our desires that we start to experience the very thing that we’ve been searching for. We begin to see that we don’t need accomplishments, or validation, or piles of cool stuff to be lovable. That we’re worthy - as cliché as it sounds - just the way we are.
Over the last five or six years, I’ve been in the throes of healing my own deep Gatsby wound. I walked away from that fancy career in fashion journalism, made it out to California, and have been exploring the freedom in dropping my outer shell, layer by layer. At times, the work I was doing required drifting as far away as possible from my glamorous past in an effort to gain perspective. I’ve sold everything I owned, bought most of it again, and lived through many seasons asking myself: Who am I as a man? What is important to me?
Along the way, I’ve been excited to share with you guys everything I’ve been learning about how men heal. Much of that work was done through the collection of personal essays I wrote between 2015-2022 and a monthly column I’ve written for Valet since 2020. Meanwhile, my coaching practice working with Gatsbys began to take off. I saw guys getting more comfortable in their skin by the day. Not to mention more in tune with their truth, authenticity, and personal power. I also started to see with new eyes the radical (and healing) shift that occurs when Gatsbys drop their defenses, and begin acknowledging what is really happening for them in a safe space.
I believe community holds a crucial role in healing the way we, as appearance-conscious men, relate to ourselves and the material world: we need safe, non-judgmental spaces to discuss the things we don’t openly admit about ourselves. We need to strip down so we can see that there’s nothing wrong with us, that we’re cool and valuable no matter what we’re wearing, what job we’ve got, or what number is in our checking account. That is the secret to living free. And I want to create that for as many men as I can. Men like you and me. Men who want to live beautiful lives, but don’t want to sacrifice everything for it.
So, in that spirit, I’m launching a weekly newsletter and blog called The Naked Man. A meeting place at the intersection of my old gig (menswear) and my new one (mental and emotional health), and a venue to dive deeper into the important questions modern men are asking themselves now more than ever.
The goal: To create a roadmap to freedom for any fellow Gatsby man who feels trapped by the pressures to keep up the facade he’s hidden behind.
Why The Naked Man? Well, a naked man needs nothing. He’s secure in himself, secure in his place in the world. He might have lots of nice, Gatsby-like things, but they don’t define him. In fact, if all of it went away tomorrow, he’d be fine. He’d still know who he is. He’d still be comfortable in his skin. That’s the kind of guy I want to be. And I’m willing to bet, at your core, you feel the same way.
Thanks for coming on this ride with me-
Sean
Are You a Guy Who Likes to Look Good?
Thanks Sean your articles and in-sites are amazing as always.
Great post Sean. I would also like to be confident in my own skin. Currently too unsure of myself