A decade of entrepreneurship ruined my mental health. Now I work at a restaurant.

My fall from glory, and the inevitable life lessons that come from the pivot.

If you told me 8 years ago that in the year 2025, I would be waiting tables at a taco spot in my hometown, I wouldn’t have believed you.

But lo and behold, last week I re-entered the workforce as an employee, and wow. Working a regular job is not for the weak.

Let’s get one thing clear before I go on: I still don’t want to work.

But The Matrix won this round, and I know I’m not the only one.

At the end of last year, it became abundantly clear to me that solopreneurship was wreaking havoc on my mental health. “Chasing the bag” was wearing me out, and the neverending stress and decision-fatigue about my next profitable option become a timeline I was ready to collapse.

One of the things I teach in my masterclass on How to Let Go is how to know when it’s time to release it.

There are many tell-tale signs, but one of the most simple (yet profound) indications that it’s time to move on is an undeniable absence of enjoyment.

And let me tell you… I was not having fun.

I knew it was time for a pivot. I took to Indeed and applied to 50+ jobs, mostly for server positions at restaurants and administrative/operations support roles at non-profits, universities, and local small businesses.

After weeks — and weeks — of updating my resume and crafting custom cover letters to position myself as the next best thing and such-and-such company, I got two measly interviews, both at restaurants. I interviewed at the first one and was hired on the spot.

After 9 years of riding the roller coaster of entrepreneurship, I now work as a waitress at a Mexican restaurant and honestly? I’m not mad about it.

This morning, I spent close to two hours doing research on the best kind of shoes for people who work on their feet. After a deep dive down several Reddit threads, I headed to the comfort shoe store, bracing myself to spend upwards of $200 on a solution to my poor, poor, aching feet.

After just a few days on the job, my body felt like I had been hit by a truck. I came home exhausted, discouraged, and very humbled.

I worked in restaurants in my twenties, and this past week made it clear that we are now in a 36-year-old body.

It don’t run like it used to.

I’m not gonna lie… thinking about this made me really sad. Aging brings with it an inexplicable grief — the loss and longing for the days when you could do anything and not think twice about the impact. (This, perhaps unsurprisingly, landed me into some regrettable circumstances, but it also brought me a sense of freedom and invincibility.

I walked into day one of training playing “Bitch Better Have My Money” — ready to do what must be done.

On day six, I was ready to quit.

My feet hurt so bad, the pain forced me back to the drawing board.

I needed something else, and I needed it quick.

I started brainstorming ways to make money that didn’t require me to be on my feet all day. I could write an e-book! I could offer discounted coaching sessions! I could teach another class!

As soon as I started scheming up my next profitable venture, I could feel the depression approaching like a storm on the horizon. I was bewildered by how quickly plan B had failed. I had committed to “taking one step at a time” and on the very first step, I injured both of my feet.

I was immediately overwhelmed with having to figure things out again. This feeling reminded me why I had applied to restaurants in the first place — because I can do what I’m told and go home.

After almost a decade of being the CEO, social media manager, product developer, financial manager, research specialist, strategic planner and administrative assistant… I was tired.

It became increasingly stressful to wear so many hats. It was maddening trying to find clients and brand myself as a "professional" or an "expert” in pursuit of contracts.

My entrepreneurship journey hadn’t started that way.

I quit my last day-job in 2020, when mental health was trending and everyone was desperate for ways to cope with stress and anxiety. People were thirsty for what I was offering, and all I had to do was sit back and wait for the invitations to roll on.

My inbox was constantly full of requests to be a guest teacher or to speak on some panel, to lead a class or wellness workshop for a team, to record meditations or to provide one-on-one coaching. Money was flowing. Business was booming. I was making money easefully and easefully. And I loved it.

After outside opened up, everything changed. The offers and invitations slowly dried up like a creek in a drought.

I quickly realized that, for the first time, I actually needed to promote myself. Not only did I need to ask for work, I needed to reimagine the entire structure of my business.

Mind you, all this is happening during a debilitating depressive episode.

Some days I did not have the energy to brush my teeth or make breakfast. Coming up with a business strategy? Creating new and exciting offerings to attract clients? Posting consistently on social media?

Be for real.

In a few short years, my income went from $85,000 to $32,000. Yikes. Ouch. Damn. It hurt, in more ways than one.

At first, there was the letting go of my wellness luxuries. I canceled my acupuncture appointments. I stopped buying organic produce.

Then, I started wearing layers instead of turning up the thermostat. I was constantly frantic about not spending too much, and trying to make more. I was posting every day on Instagram, doing my best to stay consistent enough to land some brand deals or attract people who might want to work with me.

It was exhausting. I was able to come up with a few Masterclasses to try and supplement the money I was making from my contracts, but it seemed I had reached the end of an era.

The money just wasn’t coming in like I needed it to be.

The financial strain added insult to injury. Being broke was making me depressed, and being depressed was making me broke.

I hated it. Something had to give.

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Fast forward to a few months ago, when I sat down at my laptop and decided I was going to apply for at least one job a day.

I could not manifest my way out of having to pay my bills, and I didn’t have much time to figure it out. So I went back to what I knew: restaurants and admin.

After a week on the job, I have mixed feelings.

I’m lowkey embarrassed because there’s a story in my head telling me that I’ve backslid and failed. I imagine an unfriendly audience jeering at how the “you have the power to design your dream life” coach ended up walking 6 miles a day back and forth, asking “mango or lime?” on half-off margarita Tuesdays and trying to upsell chips and queso.

It’s grim.

I can’t believe I’m here, but I also can believe it.

My life got turned the fuck upside down when Chemin died. Losing my sister shattered my whole world, and I’ve spent the last 6 years trying to piece it back together.

It tracks that I’ve had a hard time balancing it all.

And so I’m choosing to 1. Be kind to myself and 2. Find the humor in it.

It is kind of funny. Today I bought the ugliest shoes I have ever owned. I never thought I’d be almost 40, buying orthopedic shoes on a Klarna payment plan. I’m finding amusement in the absolute absurdity of this human experience. I feel so old and also so young! I’ve been doing this for so long and I’m just getting started! Every single day is a new beginning and I’m honestly just glad to be along for the ride.

My fiance keeps telling me, “Remember… if it gets too hard, you just do something else.” I know that if this doesn’t work out, I can pivot once again.

I have to remind myself that this is just a lilypad — just one of many resting places in a beautiful pond of possibilities. As always, I go from one lilypad to another, one leap at a time. When I’m done resting here, I’ll move on — using every landing as an invitation to become more of who I truly am, and to be of highest service to this life, this planet, and all living beings upon it.

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And, at the end of the day, I’m a Spiritual being having a human experience.

I’ll be in his body for as long as God allows me to be here. Life on Earth is hard and drastically unpleasant sometimes, and all of it is a part of living.

I’m feeling open and curious about why I’m taking orders and pouring sodas at this time. It makes me laugh, and I wonder what God’s up to.

I’m here for the plot! I’m not sure where this storyline is going, but I’m invested.

I hope this story reminds you that it’s okay to be exactly where you’re at.

There are no wrong moves here, friend. Every experience is a master teacher — a custom-designed hero’s journey.

If you’re ever in Charlotte, come sit in my section, (lol). If you have a job for me that doesn’t require me to be on my feet for 5+ consecutive hours, please do reach out. If you want to support my early retirement from the workforce, become a paid subscriber to this newsletter.

Thanks for being in my corner.

Love you a lot,
Jamila