5 years ago, I quit my job and sent this text

The story behind how I started my business.

Exactly five years ago (this week), I left my job, sent this text to my professional coach, and went full-time on my business.

The emoji was a nice touch. But the truth is, I was shitting my pants.

At the time, our son was 6 months old. My wife hadn’t re-entered the workforce yet. We were still in the middle of the COVID craziness, which mean we no support system, and no friends around. My entire life was happening on Zoom. And I was responsible for all of our income, plus the benefits, plus the insurance, plus whatever else a 6-month-old needs (which, it turns out, is a lot).

The stakes were high.

What was actually going on

By 2021, I’d spent 12 years in tech and the last few had really worn me down.

I worked at HubSpot in the early days, which was an incredible experience but a hard one. Then I left for a tiny company that gave me an offer I couldn’t refuse, almost a 50% raise, and it was the worst decision I ever made. I left the HubSpot rocket ship right before the IPO. I worked at the other company for just 6 months. It isn’t even on my LinkedIn. Then I went to another startup that ran out of money and laid me off a couple months in. Then I worked at Wistia and had a great four-year run, until the last year, when my boss left, the company went in a new direction and my team and I weren’t part of it.

After three tough experiences in a row, I started to wonder if maybe tech just wasn’t for me anymore.

I joined a new startup, Postscript, and I think I brought all that emotional baggage with me. I did some good work there. But I mostly spent my days bracing for impact, waiting for the next reorg or layoff or bad meeting. Always trying to ignore the “oh, here we go again” voices in my head.

And this was all happening while we had a newborn waking up multiple times a night, during the height of the pandemic.

I was stressed and anxious all the time.

Eventually, I got into mindfulness as a way to cope. I read 10% Happier (which as an anxious Jewish person really resonated with me), which led me to The Power of Now.

I eventually started a daily meditation practice.

That helped a little.

I hired a coach because I thought I was broken

On paper, I had made it.

I’d hit the titles and the seniority I’d spent a decade chasing. Director of Growth, then Head of Growth - at some badass tech startups.

But the titles didn’t make me feel good or fulfilled.

I wasn’t happy. And I figured something must be wrong with me, so I hired a coach to help me get my mojo back.

What she told me changed everything.

She said high achievers often fall into a low-grade depression after they hit their goals, because they discover the goals didn’t make them happier. They’re the same person, just with nothing left to chase. That resonated with me.

Then she gave me an assignment that, looking back, was the origin of this entire business. She called it an energy audit.

For two weeks, I logged what I did each day and how it made me feel.

One thing stood out immediately.

I was most energized when I was helping other people succeed, way more than when I was helping the business hit its number. But the single most energizing thing on the list was when people who had my job at other companies reached out to pick my brain. People leading growth teams. I didn’t have all the answers, but I’d been lucky to work places that gave me a long leash to experiment, so I’d share what worked, what flopped, the mistakes I made. I’d hang up those calls buzzing.

She encouraged me to try coaching as a side gig.

My mom has been an executive coach longer than she’s been my mom - so I knew what it looked and sounded like to coach people.

I took on a few clients on the side (my employer knew, it wasn’t a secret), and it was the best part of my weeks.

The conversation at home

You’d probably guess my wife was super nervous and I had to convince her that I should quit my high-paying tech job to take a huge gamble on something that was making a few hundred bucks a month.

But it was the opposite.

I was the one saying this idea is crazy. We have a baby. I carry the benefits. What if it doesn’t work? And she was the one saying “I believe in you. Give it four months. If it doesn’t work, you’ll get another job so fast anyways.”

So out loud, we agreed I’d give it four months.

But privately, I made a different deal with myself.

I was going to make this work or die trying. Not literally die, but you know what I mean. My actual backup plan, if I couldn’t pay for diapers, was to make an anonymized Fiverr profile and take on work way beneath my experience level until I figured it out.

That was the whole contingency plan.

A fake name on Fiverr.

Some people describe leaving a job as a leap of faith. For me it was more like a cannonball.

Burning the boats

On the day I left, I had two or three coaching clients, each paying me a few hundred bucks a month.

That was proof of concept. But definitely wasn’t a business that could sustain (at the time) a family of 3.

So I did something that took a lot of chutzpah.

I emailed my entire network, my peers, my former colleagues, my friends, and said: I’m starting this thing, and I don’t think I can be successful doing it alone. If you’re getting this email, you’re part of my community and I need your support.

I gave them three ways to help, including just sending good vibes.

I posted about it on Linkedin too.

There was no going back after that.

Because once I told everyone I knew, failing meant explaining to all of them, at every dinner and every catch-up text for years, that it didn’t work out.

The moment I knew

The early days were strange. I remember sitting at my desk some mornings realizing that for the first time in my career there was no boss, no roadmap, no paycheck arriving regardless. If I didn’t do anything, I didn’t get paid. Okay. So... what should I do?

In retrospect, I got lucky on timing.

This was 2021, when the SaaS market was frothy, and companies started reaching out asking me to advise them. I took on three or four advising gigs in the first four months, and they paid well. The coaching business grew alongside them.

I remember the exact moment my brain flipped.

It was after the second advising “yes”, which by itself covered about half my old full-time income. I thought: if I can get two, I can get a couple more. And if I can get a couple more, this is going to work.

And if this works, I’m going to do this for as long as I humanly can.

Five years later

This business has forced me to grow in ways I never could have predicted.

I’ve had to market myself on LinkedIn, which still feels cringy today, and run sales calls after spending an entire career in product-led growth specifically so I’d never have to talk to sales.

I’ve taken big swings that flopped and big swings that worked.

And I’ve had to learn to stay even keel through the revenue rollercoaster, because when you’re in a valley it feels permanent, and when you’re at a peak you get a little too confident.

Surrounding myself with other solopreneurs has also been a huge help.

In May 2021, my anxiety was an 8 out of 10. Today it’s a 2. That’s a life-changing difference.

Most days I work 10 to 5:30ish. I hang out with my family in the morning, drop the kids at daycare and pre-K, hit the gym, and fill my cup before the first call. I take two or three client calls a day. And I spend a bunch of time marketing the business.

Around 5:30 the kids get home and I’m done, out in the driveway playing basketball while they ride scooters in circles around me. I don’t work Fridays. I golf, or sit in the sauna, or snowboard in the winter. I coached my son’s soccer team this year.

Most importantly, I have space to think. And I know there’s no version of my old in-house life where that exists, because I’d be too busy prepping for the next quarterly number.

A year after I sent that first text, I sent my coach a follow-up note. I told her I was having a blast, making more money working fewer hours for myself than I ever did in-house, and that I was deeply thankful for her help getting me there.

After five years, I’ve worked with more than 95 directors, VPs, and heads of growth. I’ve hosted over a thousand calls.

And at this point, my business become my own longest employer - by a year.

When I started, the question keeping me up at night was whether I could make this work. Five years and a thousand calls later, I’ve proven to myself that I can. Now there’s a new worry creeping in:

If I stay on my own too long, do I become unhireable?

At some point, employers look at someone who’s been independent for years and wonder if they can still fit inside a company. I don’t know if I’m approaching that point. And “what if I become unhireable” feels like a stupid reason to leave a life I love and go back to a job.

But I’d be lying if I said I never think about it.

Anyways, I still feel like I don’t know what I’m doing most days.

But I’ve stopped bracing for impact.