4 Realizations That Made Me Quit My Job, Again 😳

In September 2023, I went on a solo retreat to a small beach town in Mexico.

Just a week earlier, my jaw was shut tight–I literally couldn’t open my mouth. This had never happened to me before.

I was a few days away from hosting a high-touch, 4-day retreat for 50 entrepreneurs.

And holy crap, I was so stressed.

I had been planning this event for six months. Everything had to go perfectly.

To be honest, I wasn’t stressed from the work itself. The younger Tam would have thrived hosting any kind of founder event.

But the current Tam had changed, more than he would have liked to admit. He had other interests, so doing things that he no longer felt drawn to do felt like pulling teeth.

Everything turned out fine. We could have sold more tickets, but we ended with a 9.1 NPS score and a dozen testimonials for next year. Not bad for a first-time event!

After it was over, I desperately needed time to reconnect with myself. And that’s how I found myself in Puerto Escondido, Oaxaca.

The city was much more touristy than when I first visited 7 years ago. But it had everything I needed: yoga, beach, fish tacos, and most importantly, no friends.

I didn't go into the retreat planning to quit my job. My only intention was to sit with my notebook and journal whatever came up.

I’ve done solo retreats before. In my experience, your body already knows what it wants to say. It just needs space and time to let your mind catch up.

The first few days were pretty uneventful. Probably because I was decompressing from work.

Then on Day 4, a bunch of big breakthroughs hit me out of nowhere. Things that I had always known about myself but never truly internalized.

Realization #1: I don’t ever want to have a "job" again

I’ve worked as a community builder, marketer, and writer over the last 10 years. I've been so lucky to have worked with good people on fun projects while still having free time outside work.

However, there was one thing I never had: complete freedom.

Freedom to work on what I want, whenever I want, wherever I am.

I know I'm not unique–other people want this too. But having all this space to think made me remember how freedom is one of my top life values.

More than being rich. More than being famous. More than making an impact.

I want to feel free.

I knew this about myself but had always deferred it to a "later" time. So when will that time come?

Realization #2: If I don’t change something now, I’ll be working "pretty decent jobs" for 30 more years.

Do I really want that?

I thought I did.

I really tried to convince myself that working 40 hours a week and doing hobbies on the side was good enough.

The job I had was optimized as much as it could be: great people, semi-interesting work, mostly remote, tons of autonomy, decent pay, and unlimited vacation.

Why am I not happy? Why can't I accept this?

This could be enough for many other people, but after 10 years of doing jobs like these, it's still not the ideal case for me.

I had learned this lesson before back when I worked with my career coach in 2021.

Me: “Is it ok to have a job you just kind of like and do all the fun things on the side?

Coach Kat: “I don’t know Tam. Is it OK for you?”

Me: “Yeah, I think so… I still want to explore other possibilites.”

Coach Kat: “I have a small sense that we wouldn't be on this coaching call if you were OK with staying where you are."

She knew it. I knew it.

Even when I dropped out of school in 2015, I aspired to be like the lifestyle entrepreneurs I followed.

People like Tim Ferriss, Noah Kagan, Neville Medhora, Ramit Sethi, and Ryan Holiday.

They found their perfect blend of what they're good at, what work they like to do, and what they can get paid for.

In my defense, I'd tried to start several projects before, but they didn't go anywhere. I never felt drawn to the project itself or it simply didn’t have enough market demand.

So I did the next best thing which was…

Realization #3: I worked with entrepreneurs because it felt like I was on the path to starting my own business.

When in reality, I was playing it safe.

I don't think I was afraid, but I wasn't convinced to go all in on any of my business ideas.

To be fair, I didn’t want to be an entrepreneur just to be an entrepreneur.

• I saw opportunities to be a thought leader around hosting virtual events
• I could have become a chess streamer at the height of the pandemic
• Or be another digital marketing guru dude

I knew I had a lot of hard skills to offer. But I didn’t act on any of these things.

I wanted my next project to be something that I was fully aligned with and excited to work on for the next 5+ years.

I hosted a ton of great virtual events during the pandemic. But I don't want to talk about facilitation and Zoom 24/7.

Same as chess. I like chess. I once quit my job to study chess full-time. But that obsession is gone. And more passsionate streamers would easily outwork me.

I want my work to feel like play. I want to bring my soul into my work.

Or else my only motivation would be money, which wasn’t enough for me.

Holy crap.

Holy crap.

Holy crap.

Does that mean... I’m actually going to quit my job?

What am I going to do instead?

How am I going to make money?

deep breath

I'm sitting on the sand facing the ocean.

I feel the wind breeze through the side of my head.

I hear the waves crash on the shore.

I watch the sun slowly set until it finally disappears.

another deep breath

Wow, life is so beautiful.

The next day, I go to a cafe to journal how this new chapter may pan out.

I braindumped everything. Most of it was me going in circles. But I had one big learning that day.

Realization #4: There is always a risk of doing something unknown. But the risk may not be as bad as we might first assume.

I took a page from Tim Ferriss' fear-setting activity and mapped out the potential best and worst-case scenarios.

• Worst case scenario: I spend $10k and 6 months of my life building something that no one wants. I abandon the project, move back home with my mom, and find another job.
• Medium case scenario: I build something people want, but not enough people want to buy it. So it becomes a side hustle while I do freelance work. Or I find a job more aligned with new skills that I want to learn (that I discovered from my side hustle).
• Best case scenario: This business funds my lifestyle and dance training. I put my heart and soul into my work. I get to work with talented friends and generously compensate them. I have a lot of fun and create a big impact in my little tiny corner of the world.

Once I put these scenarios down on paper, I realized the worst-case scenario isn't terrible. It'll suck, for sure. But it's not the end of the world at all.

And for the potential reward to work on a project I love and have this business fund my dance addiction?

Quitting my job didn’t feel as risky after all.

It suddenly felt like the most logical step.

(I know not everyone has $10k in savings and the option to move back home with their parents. But imagine you were in my shoes. Would you take this risk?)

I also spent that week rereading Do What You Love or Die Trying by Blake Boles.

This book spoke to my soul. The premise is basically the title, but told through beautiful stories and poems.

It was the final tipping point for me to take the leap.

As I boarded my flight out of Puerto Escondido, it was decided: I was leaving my job to start my company of one.

My next post will cover how I'm building Bachata Library. But I’ll end by sharing one last message from my career coach that I keep close to my heart to this day.

*after my monkey mind ran around for an hour trying to find "the answer"...

Coach Kat: "Tam, you are someone who lives your life with your eyes wide open. You will find the work of your life. It will call you.

You can pick up the phone and answer it, when that time comes."