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The Life-Changing Decision That Saved Me

Jun 05, 2024

🗣️ Quote of the Week:

"You don't have to see the whole staircase, just take the first step." – Martin Luther King Jr.


In this week’s dose, I share about the pivotal point in my journey that led me to leave corporate, take a chance on building my first company, and follow my gut.

In March of 2019, I was living in Chicago working for a tech company making $200k+ and working about 10 hours per week.

I was training CrossFit when I wanted, traveling when I wanted, and had plenty of spending money. But I was looking forward to the Saturdays so I could start drinking at noon with my friends and escape from the rest of my life.

I had some challenging things at work like a very toxic boss, no quota, and no clear plan for my role even though I had been there for a year. I had been battling the ups and downs of depression for about 2.5 years at that point and things just weren’t working.

My passion for work had disappeared.

I stopped waking up at 5am to work out.

I was drinking more, doing more drugs, hadn’t dated anyone in 3 years, and had no clue what was next.

I decided I was going to do a full reset. I applied for an Australian visa to live remotely for a year. My plan was to coach CrossFit and bartend by the beach. I’d figure the rest out later.

I was a month away from moving and one of my good friends (and former boss) encouraged me to interview at the new, sexy startup he was at in the Bay Area. He was telling me how reps were making $300k-400k in commission checks in a single quarter alone - this hooked me.

So I abandoned my plans to reset and stayed in tech, thinking this time would be different.

I started off strong and began discussions about moving into leadership as the company was growing quickly. But as COVID hit, things became more difficult within the workplace. And I found myself alone at home, hating the work I was doing, getting drunk most days, and wondering what the hell I was doing.

Ultimately, I was fired for missing quota. I could provide a long list of all the reasons why it’s fucked up how it happened, but I’m so thankful it did.

I wasn’t upset that I lost my job. I was upset with how I felt about having no clue what was next. I finally started to realize that no paycheck, no company perks, and no title was going to change how I felt.

I didn’t understand why I felt depressed and I was angry that I couldn’t figure out how to “fix” it.

I had cried maybe 3 times in 10 years, and now I was crying every day - often uncontrollably, staring in the mirror at myself like a crazy person. There was a point I was stooped over my bathroom sink in my San Francisco home and I heard the thought “You have to get YOUR fucking life back.”

What that felt like to me was that I needed to say fuck all the bullshit. Fuck the titles, fuck the money, fuck tech sales, and fuck trying to succeed at a life that is making me miserable. It was telling me that I needed to wake up and listen to myself — to my gut, my intuition, whatever you want to call it.

And I bought in.

In that moment, I felt a shift within me that said I was all in. I didn’t know what it’d look like, but I knew that how I was living clearly wasn’t working. I was caught up in playing the wrong game.

That week, 2 things happened to me. First, I heard the idea that everything in life is neutral and only our mind creates meaning - good or bad. Holy crap did that stop me in my tracks.

It was me! This whole time, it was me.

It wasn’t my ex, my toxic boss, my crappy territory, COVID, the city I lived in, my apartment, etc…

It was me.

That was so freeing to me. I wasn’t better overnight, but I felt like I had a clear path forward again. I had to stop trying to fix everything outside of me and work on my own inner world.

Second, I heard a quote by Barbara Corcoran (Shark Tank) that said if you have an idea you can’t get out of your head - even if you have no idea why - you HAVE to follow it.

Well I had the idea pop into my head a thousand times in the previous 5 years to start a clothing company. And when I heard that quote I thought “Damnnn, do I need to do this!?”

The next morning, I woke up and the first thing I thought of was “clothing company” - that felt like another sign. I thought about it for a few minutes, swung my legs over the edge of the bed, and said “Fuck it, I’m doing it.”

I still get chills thinking about that moment. 

It was so powerful for me because it was a moment of commitment. And in my experience, when we commit to something, there’s an exchange of energy that happens with the universe. That when we commit and take action on the things that fire us up, the universe helps make it happen for us (I can’t explain why this happens, but I’ve stopped fighting it at this point).

Those 2 things happened within a couple days of each other and have shaped how I live my life now.

I know that everything in my life comes down to my inner world. And if I’m triggered, upset, depressed, etc that’s my problem - not anyone else’s.

I know that my only responsibility on my path is to listen to my gut & intuition. To take action on the things that excite me and to stop doing the things that feel out of alignment.

Put those 2 things together and you have an incredible playbook for how to be a human.

If I wouldn’t have acted on the clothing company idea, I wouldn’t be doing what I’m doing now.

And if I wouldn’t have learned to heal myself, I don’t think I’d be here now.

Tim 🖤


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