For Those Who Feel Stuck
“You can’t go back and change the beginning, but you can start where you are and change the ending.” — C.S. Lewis
Feeling stuck does not mean something is wrong with you.
It doesn’t mean you failed. It doesn’t mean you are behind. It may mean the life you’ve been living no longer fits, but the next chapter has not revealed itself yet.
It may mean the part of you that has been striving, achieving, coping, and holding everything together is exhausted. It may mean a deeper part of you is asking to be heard.
That is what happened to me.
Six years ago, I was desperately trying to save my tech sales job.
From the outside, my life looked pretty good. I had made good money and worked at well-known companies. I had lived in San Francisco, New York, Chicago, and then back to San Francisco. I knew how to perform and achieve.
But internally, something had been unraveling for years.
I was burned out, depressed, and disconnected from myself. I was afraid of losing my job, but even more afraid that keeping it meant continuing down a path that didn’t feel like mine anymore.
Deep down, I knew I wasn't where I was meant to be.
I also knew that once I was fired for missing my quota, it would be nearly impossible to interview again. I’d have to explain why I lost my job, why I had jumped around so much, and why I wanted another sales role when, in my soul, I knew I didn’t.
There was something else for me. And it scared me that I had no clue what that was.
It was a stirring in 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. That way, I wouldn’t have to step into the unknown and face potential failure.
What I didn’t realize was that I was already facing both.
I was already living with uncertainty. I was already failing at living a life that felt true. I was already in pain. The only difference was that I was suffering inside a life I no longer wanted.
I kept coming back to one thing: I feared leaving the security of a paycheck to start my own thing because I had no clue how it would turn out. But I had just gone through four years of declining mental health, so I had already learned that a good paycheck wasn’t the answer.
That was a reminder I needed.
The fear of failure was far from the worst thing I had experienced.
I felt such desperation and yearning to feel good again. I knew I had to keep an open mind and try something totally new. So I said, fuck it, I’m going all in and starting a clothing business.
It was an idea that had regularly popped into my head for over five years. Each time, I’d brush it off and tell myself it was dumb.
But this time, I listened.
Within 18 months, I started to understand how hard it would be to make money selling apparel. And I’m not talking millions. I’m talking enough to pay my bills. I was in over my head, but I still believe it’s the best decision I’ve ever made.
Not because the clothing business became the thing. But because I was finally trusting that deeper part of me.
When I decided to listen to my gut, I felt reinvigorated. I see it as one of the most transformational moments of my life because I finally honored the deeper voice within, even though I had no idea how it would turn out.
I was sick of living life how I thought I was supposed to live it. I became laser-focused on turning my mental health around and becoming the type of man I knew I was capable of. This was the first domino.
Every morning, I’d write about who I had to become to be a successful entrepreneur. Then I'd visualize it. I realized I had to improve a lot about myself. It forced me to be brutally honest about where I was slacking and where my strengths were, which is hard to admit when you're feeling low.
But I started to find my passion again. My fire came back.
I’d wake up at 5am, take a cold shower, meditate, read, journal, and jump on my computer to build my company. Four months in, I was amazed by how much momentum I had built and how much progress I had made. It was something I hadn’t felt since my baseball days a decade earlier.
My depression had subsided, and I was healthy, fit, and driven again. I even chose to start cutting back on alcohol because I realized it wasn’t aligned with who I wanted to be anymore. That was the first step that led to me quitting two years later.
Eight months after I left tech, I decided to share a post on LinkedIn for the first time. My thinking was simple: if I built a little personal brand on LinkedIn, maybe 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 people resonated with the message.
This would turn out to be a huge lesson for me.
I thought I was building an audience to sell shorts. What was actually happening was that my wound was becoming a doorway into service.
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 loved one who was struggling.
I kept hearing the same themes.
People were burned out, unfulfilled, and isolated. They were scared to be vulnerable. They felt lost and like they had no purpose. They had fractured relationships and unhealthy habits. They had no close friends to talk to and didn’t know where to begin.
So many people looked fine on the outside, but privately felt like they were carrying something they didn’t know what to do with.
It became clear to me that 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 the practices had helped me.
In February 2022, I invited four men to join my first 28-day cohort for free. Then I did the same thing a few months later. I ended up facilitating four free cohorts that year.
The work was meaningful, but I still couldn’t figure out how to make it a real business. In the second half of 2022, I tried to get paying clients and failed to sign anyone in my first 20 consultations.
I knew the program was working, but I had serious doubts about whether I could make money this way. I still refused to call myself a coach, and I had major imposter syndrome. My fear and self-doubt were limiting me from enrolling new clients.
At the same time, I was draining my savings and started interviewing for sales jobs again. I made it to two final-round interviews on the back of strong referrals, but I bombed both of them.
Now, I see it as a divine wink. A nudge helping me on this journey.
At the time, it felt like rejection. Looking back, it feels more like guidance.
I made one last attempt to save my business and invested $2,000 in a coaching course for aspiring coaches. My savings were declining, and I hadn’t made any income in 30 months. I already felt a lot of fear and scarcity, and here I was paying $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, it showed me 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 direction. I started coping with cannabis and food. I had amazing clients, but I could sense that I needed to evolve myself and the program in some way.
Something in me knew I had outgrown the version of the work I had been doing, but I could not yet see what it was becoming.
Then in June, I was hit with the hardest, deepest depression I’ve ever felt. It came with things I had never experienced before, like crippling apathy and daily thoughts of suicide. I felt like I was wearing a 75-pound steel blanket.
That dark period lasted over 100 days. It felt inescapable.
I was searching for anything that might help me snap out of it or find the breakthrough I knew I needed. I looked at hiring coaches, working with therapists, and attending a 10-day silent meditation retreat. I thought about moving to Costa Rica for a month. I explored plant medicine ceremonies and visiting Michael Singer's temple in Florida, the author of The Untethered Soul.
Anything that could help.
I even thought about going to India. I had been reading books like Autobiography of a Yogi, I Am That, and The Surrender Experiment. I spent my free time listening to Ram Dass’ talks from the 70s. I wanted to feel what they experienced in India. I wanted to feel the oneness, connection, and love they described.
Which led me to a divine moment.
On a catch-up call with a friend, she mentioned she was going on a pilgrimage trip to India with one of her teachers. It would be a small group traveling to 6 or 7 cities and visiting sacred sites. Not a typical tourist trip, but one with reverence and a deep spiritual undertone.
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 for a life-changing experience. Some kind of miracle that could fix me immediately.
That didn’t happen. I didn’t come home fixed, but it was an incredibly moving and impactful trip. I came home with enough light to keep going.
On one of our bus rides, I shared with the group that I had gone three straight days without a single thought of suicide, the first time that had happened in nearly five months.
Something was clearly happening, even if my logical mind didn’t understand it.
When I got back home to Austin after the trip, I started slipping back into some of the habits and heavy feelings I had before I left.
I thought, shit, here we go again.
Then I saw a video of a guy sharing how his life changed during his walk across the country. He had walked in 2019 after his dad died, and he was going through a rough period. The moment I heard him say the words “walk across America,” I felt like a lightning bolt went through my body.
I thought, “Holy shit, I want to do that.”
Then immediately after: “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 was that everything I went through that 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 the way I did if I hadn’t experienced those 100+ days. I would have never been able to take six months to do the walk if my business were where I wanted it to be at the beginning of the year. I would have never been able to do it if I hadn’t received so much support from my friends and family, which inspired me to keep sharing the story.
That doesn’t mean I would have chosen the pain I went through. But I can see now that life was using even the parts I hated to shape me for something I couldn’t yet understand.
I wrote the above 75 days before departing on a 3,000-mile journey. I knew it would be the hardest physical thing I’ve ever done, but I was ready.
And now, writing this from the other side of that walk, I understand something even more deeply: the path rarely reveals itself all at once.
You only get the next step right in front of you. And it’s not always obvious.
A conversation. A gut feeling. A strange pull. A sentence someone says that lands in your body before your mind knows what it means. I used to think breakthroughs would come as one major moment. But they usually come as a nudge.
Final Thoughts
The things you’re going through now may just be preparing you for what’s to come.
I don’t think every hard thing happens for a reason in some clean, easy-to-understand way. Some things are brutal. Some things break your heart. Some things you would never choose to go through. That’s all part of the human experience.
But I do believe life can use everything. It’s our best teacher if we allow it to be.
Even the job loss. Even the failed business. Even the depression. Even the season where nothing makes sense. Even the pain and hurt you would have never chosen. Pain is not proof that something is wrong. It’s typically a sign that something within you is ready to be seen.
Feeling stuck is not failure.
It’s not proof that you are broken. It’s not evidence that you took a wrong turn and your story is ruined. It may be life slowing you down enough to finally see what you could not see while you were moving so fast.
“Life is what happens when you are busy making other plans.”
It may be the intelligence of something deeper in you refusing to keep walking in a direction that no longer feels true to you. That does not make the season easy. It doesn’t mean you have to like it or that you would have chosen it. But it does mean this moment can be worked with. Even this can become part of the path. “This, too.”
So if you feel stuck right now, I wouldn’t tell you to try to force clarity.
I would tell you to slow down enough to be honest with yourself and tell the truth. To listen to the part of you that is tired of wearing a mask. To pay attention to what gives you even a flicker of aliveness.
Allow that to be your guiding beacon.
- Tim
P.S. If this resonated and you’re in a season where you feel stuck, overwhelmed, or disconnected from yourself, I created a free 7-Day Reset to help you slow down, get out of survival mode, and begin finding your way back.
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