The Roadmap to Freedom

By the time I turned 30, I was living what I believed would be my dream life: my days were spent filing stories for GQ Magazine in New York City, where I worked as a writer covering the global fashion beat. I had a closet full of designer clothes, a midcentury cabin in the Hudson Valley, and the girl of my dreams to come home to every night. My life looked great on the outside. But inside, I was hurting. Hurting from a painful past punctuated by my father’s suicide a decade before. Hurting from addiction, fear, and insecurity. Hurting from that constant feeling that, no matter what I achieved, I was never good enough.

My glamorous life was a house of cards waiting to fall, and when it did, I found myself standing on my Brooklyn fire escape contemplating the long jump down to the street. Those dark days of 2015 were a wakeup call: without my cool guy job (I’d burned out and quit), my status as a tastemaker (without the job, the calls had stopped coming), and my girlfriend (she’d left me to “find herself”) to keep my self worth propped up, I quickly saw I hated myself. So much that I wanted to take my own life the same way my father had. And I didn’t want to go out that way.

So how does a man go from hating his own guts to loving himself? I had no idea where to start back then. And truthfully, the process has been nearly a decade of trial, error, and a willingness to experiment — an inward journey that’s taken me from books and podcasts and plant medicine ceremonies, to men’s groups and spiritual psychology graduate programs and intimacy therapists, just to name a handful of the places I’ve searched.

What all of it has taught me is that feeling good is ALL about our relationship with ourselves: until we, as men, come to love and accept ourselves, we’ll always be searching for something outside us to indicate to us that we’re okay. And it’s a losing game: our constant search for “more” burns us out, numbs us out, and keeps us further from the relief we’re actually seeking. Meanwhile, if we’re willing to slow down and do some intentional inner work to learn how to honor and accept ourselves, we can get back on track to living the kind of deeply fulfilling existence we all crave.

Last year, after four years and hundreds of men coached, I launched a program — “The Roadmap to Freedom” — an A to B solution designed to take guys from that externally focused approach we all grow up ingesting (get the job, get the partner, get the success on the outside and you’ll be happy) to an alternative approach (get good with yourself on the inside and watch your life transform and align.) Here are a few highlights of the journey:

1. Take a look at your origins

The kind of man we become starts in our family of origin, and community. And the way to locate it is by asking ourselves two questions: What got me love from my parents? What got me love from the world? By locating how we adjusted our personalities to our surroundings, we begin to see the origins of the persona we developed to become likable, popular, cool, successful, or merely to survive. (And which ultimately began to distance us from our true selves.)

An example: since my dad was obsessed with glamour and prestige, I was always drawn in the same direction. I wanted to be cool and magnetic and popular like he was. So I learned how to fit in in even the most exclusive rooms. A tasty talent to have, sure, until I realized I was fitting in at the expense of my own truth, often hiding my true self to please others. This needed to change.

2. Meet your shadow

Once we’re aware of our adaptive or outward-facing identity, we also become aware of all the aspects of ourselves we’ve suppressed, or kept hidden to be liked or accepted by our parents, community, and the world at large. This is what is commonly referred to as “shadow work” (a nod to the work of famous analyst and Freud acolyte Carl Jung): the intentional parading of our skeletons out of the basement and into the light of day. It’s true that we can only love what we know. So in order to love and accept all of ourselves we have to be willing to love and accept even our dirtiest and most shameful secrets.

A helpful exercise: Make a list of the things you’d never want anyone to know about you, and then share it with a trusted friend, therapist, mentor or coach. This intentional vulnerability leads us to our next important step…

3. Practice self-compassion

Too many of us men have strong inner critics who berate ourselves with negative self-talk all day. This isn’t helpful, and actually acts as a continual act of self-sabotage. But sharing your most unlikeable parts with someone else is a compassionate act. It’s an intentional unburdening and the beginning on the road to freedom. I’ve never experienced a man sharing his most unlikable parts of himself with another man or a men’s group without seeing a bunch of guys’ heads nod like: Yeah man, I’ve been there too. Yeah, I know exactly what you mean.

Knowing we’re not alone in our “baggage” is the beginning of having compassion for ourselves, and forgiving ourselves for the things we’ve done to get by in the past. Remember: we’re all trying our best. And if we had the awareness to do something differently, we would have. This realization diffuses the judgments we hold against ourselves. As we release these judgments, we start to feel more free and loose with ourselves, and subsequently, everyone around us.

4. Feel it all

As men, we grow up believing our feelings are weakness, and suppress certain emotions as “negative.” In reality, all of our emotions are healthy, and the more we encourage ourselves to feel whatever is coming up in the moment, the more we come into right alignment with ourselves, which makes us powerful.

Exercise: Simply putting a hand on our chest each morning as we wake up and asking: How am I feeling today? Can be a major shift for many of us. Ditto honing a good journaling practice. For me, men’s groups were also a huge way of getting in touch with the full spectrum of my feelings — including a lot of stagnant and unexpressed emotions from the past. I will always remember the moment I got viciously angry and lashed out at my friend Juan during a weekly men’s group I attended in Santa Monica. I was sure my outburst would be the end of our relationship, but at the end of the session Juan walked across the room and hugged me. “I like seeing your fire,” he told me. We laughed, and that changed my relationship to anger forever. Now, I embrace it as the healthy human emotion it is. It’s my fire, my passion, my life force if wielded correctly.

5. Honor yourself

The more we love and accept ourselves in wholeness, the better we take care of ourselves: this can be from the quality of the food we eat, to the sleep we’re getting, to the kinds of relationships we allow into our orbits. Simply put: the more I love myself, the more I take care of myself. One of my favorite things is seeing the guys I coach walk away from marriages, careers, and even cities that no longer serve their evolution and growth in favor of walking towards people, places, and things that inspire and light them up. Whew! Powerful, right? It’s true that when we do the inner work of learning to love ourselves, our outer lives change too. And that’s when things start to get really juicy.

6. Create a vision

As we learn to take better care of ourselves, we can begin to envision and even feel into what we want our lives to feel like each day. What makes us excited to get up every day? What’s the legacy we want to leave behind us: for our families, for our communities, for our colleagues? How do we want to be remembered? It’s in this vision that we discover our individual values and who we are at our cores. And by beginning to live those values in the world, we become powerful, loving examples to other men traveling this path. In ancient cultures, men would be initiated into manhood by other men who had walked the path before them, the path into the heart of who they truly were. This is largely missing from modern society, but we can create it now.

For me, creating a vision for my life meant leaving the fast, hectic life of New York behind for the vast nature of Topanga Canyon, a close-knit mountain community outside Los Angeles. It’s here, amongst the silence of the early mornings, that I enjoy a simple life: surfing, writing, hanging out with my dog and my friends, as well as helping other men leave the past behind and create lives they love living every day. I love my life, and giving it to myself every day is the ultimate representation of the inner work I’ve done and the journey I’ve been on to get here. I’m damn proud of myself for it. And I want every man who wants that feeling to experience it.

For more information on the inward journey I lead men on, check out my Substack, The Naked Man, or my website.