A Letter To Every Man Who Feels Stuck

Read time: 6 mins

QOTW

"You can’t go back and change the beginning, but you can start where you are and change the ending." – C.S. Lewis

Life has a funny way of unfolding for us.

4.5 years ago, I was desperately trying to save my tech sales job, fearing what would come if I lost it. I had jumped around a few jobs in a few years, going between startups and established companies - selling to both small and enterprise businesses. Moving from SF to NYC to Chicago and back to SF within a 4-year span.

I realized that, once I was fired for missing my quota, it would be nearly impossible to interview again. Not only would I struggle to explain why I lost my job and job-hopped so much, but I knew in my soul that this was no longer my path.

It was a stirring inside my gut that was stronger than any argument my mind could make. I knew I wanted my own business someday. But it was easier to keep it a pipe dream than to act on it.

I kept coming back to one thing. I feared starting my own business and had no clue how it would turn out. But I had just gone through 4 years of declining mental health. That was a reminder that the fear of failure is far from the worst thing I've experienced.

I felt such desperation to feel “good” again that I said: fuck it—we’re going all in. We’re starting a clothing business.

But 18 months in, I started to understand how hard it would be to make money with a clothing line. And I’m not talking millions, but enough to pay my bills and get in the black. I was in over my head, but I firmly believe it’s still the best decision I’ve ever made.

When I made the decision to honor my gut and do what I wanted for once, I felt reinvigorated. I was sick of living life how “others” wanted. I became laser-focused on turning my mental health around and becoming the type of man I knew I was capable of.

I’d write every morning about who I needed to become to be a successful entrepreneur - then I'd visualize it. I realized I had to change and improve a lot about myself. It forced me to be brutally honest about where I was slacking AND where my strengths were (it's hard to admit your strengths when you're feeling low).

But I started to find my passion again. Like my fire came back.

I’d wake up at 5am, take a cold shower, meditate, journal, and jump on my computer to build my company. Four months in, I was amazed by how much momentum I built and how driven I’d become. Something I hadn’t felt since my baseball days.

My depression had subsided, I was healthy, fit, and unbelievably driven. I even made the choice to start cutting back on alcohol. I realized it wasn’t aligned with who I wanted to be anymore (this was the first step that led to me quitting 2 years later).

Eight months after I left tech, I decided to share a post on LinkedIn for the first time. I had the idea that if I built a little personal brand on LinkedIn, I could sell more shorts when it was time to launch.

My mission for the clothing brand was to help men get healthy—mentally and physically. So I wrote about my struggles with health, tech culture, sales, and entrepreneurship. And I wrote about everything that helped me get through it.

The more personal stories I shared, the more I gained traction. The more vulnerable I was, the more people resonated with the message. 

This would turn out to be a huge lesson for me. 

In those 9 months from April to December 2021, I had 150+ calls with men and women who resonated with what I was sharing. People who had struggled in the past, were struggling now, or had a struggling loved one.

I kept hearing the same themes: burning out, feeling unfulfilled, and isolated. People were scared to be vulnerable. They felt lost and had no purpose. They had fractured relationships and unhealthy habits. They had no male friends to talk to and didn't know where to begin.

It was clear to me THIS is where I could have an impact.

Working directly with men felt more aligned than selling shorts and making content. So I started brainstorming a program to help guys get back on track the same way it helped me.

In February 2022, I invited 4 men to join my first 28-day cohort for free. Then I did the same thing a few months later and ended up running 4 cohorts in 2022 (all for free).

I was trying to get paying clients in the second half of the year, but I failed to sign anyone in my first 20 consultations. I knew the program was working, but I had serious doubts about being able to make money. 

I refused to call myself a coach and had major imposter syndrome. And my fear and self-doubt were preventing me from enrolling new clients. 

At the same time, I’d been draining my savings and started interviewing for sales jobs again. I even made it to 2 final round interviews on the back of strong referrals, but I BOMBED them both.

Perhaps it was divine intervention...

I made one last attempt to save my business and invested $2,000 in Stacey Boehman’s coaching course for coaches. My savings were dwindling. My fear-based scarcity mindset was in full force. And I was shelling out $2k just like that? Wild.

But 13 days later, I had brought in $9,000. It worked!

That year I worked with 65+ clients and brought in over $100k. It was validating on so many fronts, but most of all, that men’s work was needed and wanted.

2024 started out hot, and I thought it was going to be a banner year for me.

But I struggled.

My writing got stale, I lacked clarity on my vision, and I started coping with things like weed and food. I had amazing clients, but I could sense that I needed to evolve myself and the program in some way.

In June, I was hit with the hardest, deepest depression I’ve ever felt. It came with things I’d never experienced before, like crippling apathy and daily thoughts of suicide.

That dark period lasted over 100 days. It felt inescapable. 

I’d been seeking some way to snap out of it and find the breakthrough I knew I needed.

I looked at hiring coaches, working with therapists, and 10-day silent meditation retreats. I thought about moving to Costa Rica for a month. I also explored plant medicine ceremonies and visiting Michael Singer's temple in FL (author of Untethered Soul).

Anything that could help.

I even thought about going to India. I’d been reading books like Autobiography of a Yogi, I Am That, and Surrender Experiment. I spent my free time listening to Ram Dass’ talks dating back to the 70s. I wanted to feel what they experienced in India.

Which led me to a divine moment...

On a "catchup call," my friend mentioned she was going on a pilgrimage trip to India with one of her teachers. It’d be a small group traveling to 6-7 cities and visiting sacred sites.

The hair on my arms stood at attention, and I knew I had to go.

I wasn’t sure what I wanted out of the trip, but I was hoping to get a life-changing experience. Some kind of miracle that could fix me immediately. That didn't happen, but it was an incredibly moving and impactful trip.

On one of our bus rides, I shared with the group that I had gone 3 straight days without a single thought of suicide—the first time that had happened in ~5 months.

Something was clearly happening, even if I couldn’t put my finger on it.

When I got back home to Austin, I started to slip back into some bad habits I had before the trip. I thought "shit, here we go again."

But I saw a video of a guy sharing how his life changed during his walk across the country. How he learned happiness was a daily decision and that he now felt a deep sense of love for life.

The moment I heard him say the words “walk across America,” I felt like I had a lightning bolt go through my body.

I thought “Holy shit, I want to do that!” followed by “Holy shit, I’m GOING TO do that!”

And I knew I wanted to use the walk to raise awareness for men's mental health and suicide prevention.

The craziest part to me?

Everything I went through this year made sense in that instant.

It was all preparing me to take this leap and step up for a cause bigger than me.

I would have never been able to understand suicide if I hadn’t experienced those 100+ days. I’d never been able to take 6 months to do this walk if my business was where I wanted it to be at the beginning of the year. I’d never be able to do this if I hadn’t received so much support from my friends and family which inspired me to keep sharing this story.

Now here I am, 75 days away from departing on a 2,800-mile journey.

It'll be the hardest physical thing I’ve ever done, but I’m ready.

Final Thoughts

The things you’re going through NOW are simply preparing you for what’s to come.

Trust the universe is working FOR you, see your challenges as lessons, and be willing to serve others.

Not only is there still hope, but you’re closer than you think to your breakthrough.

Learn to listen to the parts of you that come from a place beyond the mind - they come from your gut, your intuition, your soul.

Keep going. You got this.