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The exact moment I knew I was quitting my job

Years ago, back before I had my own bidness, I worked a regular degular job.

Okay, maybe it wasn’t “regular degular.” I worked for a hot new startup that experienced explosive growth in a short time. I worked remotely the entire time — way before covid made remote work cool. I traveled to the Philippines, and countless cities across America. And it oozed “millennial money” vibes.

But it ‘twas a job with bosses and managers and meetings out the wazoo.

Anyway, after about 18 months as an employee, I knew I wasn’t cut out for employment.

And I officially quit about 2 years in.

But there was a specific moment when I *knew* I was gonna quit. This came around that 18-month mark.

I didn’t know the first thing about running a business, so I was scared. But I also bet on myself and my email copywriting skills.

My only regret nearly 3 years later is that I wish I quit sooner.

Anyway, what made me quit?

Well, sit down and buckle up, bucko, because what I’m about to say can make a world of a difference to any leaders (and future leaders) reading this.

Here’s the story:

About 18 months in, we got into a big webinar kick. And I don’t mean the VSL-type webinars (aka the ones that actually sell your service and make sales). Instead, it was a guru-y “vAlUe aDd!i!i!” type webinar, which is to say, they were unfocused, unpersuasive, and unimpactful.


We were running the latest installment in this dreadful webinar series. We had a webinar topic so boring it made watching paint dry sound exciting and dramatic. And I was in charge of persuading mfs via email to join this webinar.

But this webinar had a difference:

My higher ups—who all suffered from extreme cases of Shiny Object Syndrome—wanted to get more people to sign up. Instead of making the webinar topic more sexy and exciting, their idea was to add an “Add-to-Calendar” link inside the email, so people could click a button and see the webinar on their schedule.

And, well, back in 2018-2019, this wasn’t an easy task. I found some website that could spit out an “Add-to-Calendar” link for the various types of online calendars people use. But it wasn’t as simple as plugging a date and time and getting the link.


Because you had to do crazy scientist time zone math. The website converted everything to UTC time. I worked in EST. The company I worked for flip-flopped between MST and PST time.

Not an easy time zone equation.

And so, I fvcked up.

It was a silly lil mistake, yes. But it saved me from the “corporate rat race” (well, at least as much of a corporate rat race you can find yourself in when you worked for a company that oozed millennial money vibes).


Because this mistake made me realize I’d do whatever it takes to start my own bidness.

Here’s the sitch:

We had 4 people who signed up and also clicked the “Add-to-Calendar” link.

(There were only like 10 sign ups total, remember this webinar topic was more boring than watching paint dry.)

As for my mistake?

After doing all my time zone math and hurting my brain, I accidentally swapped a PM for an AM.

Since we scheduled our webinar for noon, this meant people who clicked the “Add-to-Calendar” link found this webinar in their calendar at midnight.


A mistake? Yes, but not a massive deal.

Or so I thought.

One person reached out to us and told us about our mistake. This wasn’t ill-intentioned. I think the bloke was trying to help. (There’s a case that this random person helped my life and career more than anyone else — and I don’t even know his name.)

Anyway, our CEO found his reply about our mistake on—and I’ll never forget this—an autumn Sunday afternoon. It was a damn near spiritual day. The sun shined through the trees in a way that reinforces your belief in God. The birds chirped away happily and flooded my earholes with beautiful songs. The fresh autumn breeze reminded me that summer was still here in spirit, but would be leaving us soon — which elicited a special kind of bittersweetness.

Then, I checked my email, and I had a Loom video waiting for me from the owner.

I was sitting in my recliner, reading a copy of Ben Settle’s Email Players newsletter, when I opened the Loom video. I was in a near-bliss state of mind. I might’ve even just wrapped up a meditation session, but my memory’s a lil fuzzy.

Anyway, I opened up the innocent-looking Loom video and got ab-so-lute-ly BERATED.

The CEO, on the other end of the Loom, shrieked at the top of his lungs.

He told me about what a stupid mistake I made. How I had to reach out personally, via Gmail (not HubSpot, which we used for email marketing at the time), to apologize to, check notes, all 4 people who clicked this link. And told me I had to do it NOW — he didn’t give a rat’s arse or fart that it was a Sunday.

My blissful mood morphed into anger and motivation.

At that moment, I gave myself 6 months to try to build up a client list, so I could quit my job.

And, well, the rest is history, as they say.

What’s the point of me sharing this humiliating story with you?

There are a few:

1. If you’re a leader, you must always treat your employees with respect and dignity (even if they make mistakes).

I mentally clocked out after this — despite all the things the company did to woo me. I never went above and beyond the call of duty again. And I submitted my two-week notice about 6 months later (which was far too long).

2. Mistakes in email aren’t the end of the world. In fact, they can be a hidden way to make more money.

3. Sometimes bad situations are blessings-in-disguise.

Cliché, yes.

True, absolutely.


That moment led me to here — and led you to me.

Mayhap it’s a coincidence. Or mayhap it’s a sign that we’re destined to work together.

Wanna see if it's the latter?

Grab a time, and let’s hop on a call. And if we’re a good fit, let’s send your email revenue up to where the Tesla car floats in the deep abyss of space.


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