My entire life, until October 27, 2015, was structured around the premise that the majority of each weekday needs to be occupied either with a job, or with escaping that job. In New York, that’s how I’d filled my days. The moment I stepped off the plane from Hong Kong, back from my 3-week trip to Asia that included in-laws, drum clinics in 3 countries, and a business conference with the only organization I’ve every been proud to belong to, I knew everything had changed. At the risk of sounding hacky, I couldn’t go back.

This Wednesday will mark the two-week anniversary of my giving notice at my job, and I’m only now circling back to write the post I’d visualized writing since last March.

It happened exactly the way I’d fantasized about it. But I’ll leave the sordid details out. You’re probably more interested in the how and the why anyway.


I returned from Asia with 3 things highly destructive to holding down a job: an appetite for slow international travel, a business knocking-on-the-door of being able to support me, and a vague sense that everything would be alright. That sense wasn’t just superstition. I’d finally spent enough time around people making money without employers to know (a) that it’s possible, (b) a lot of the particular shapes that possibility tends to take when it turns into success, and (c) an assurance that even if my primary business isn’t the be-all-end-all, I already have skills people will pay for, because (b again) I’ve seen them paying for it.

Other members of my entrepreneur network greeted the news that I’d quit with knowing smiles, the way a coach meets your eyes the first time you pull off a muscle-up. “I knew you could do it, and I was hoping you wouldn’t wait too much longer.”

But why not just stay in the job if I’d already pulled off the hat-trick from 4HWW? In short: being able to sleep at night, and breaking out of somebody else’s frame.

Too abstract? Imagine taking money from overly meddlesome parents. It’s about like that*.

The first bitter pill is knowing you’re not “living up” to expectations. As long as you’re taking a salary, it’s presumably for providing something in return. In my world, it was for being a “good employee”. For the last three years I’ve been a mediocre-at-best employee, especially by the metrics my company keeps, and I didn’t like that incongruence. Sure – I can justify my actions by telling myself I was still proving value to the company in excess of my salary (True, by my belief), and further that I was in a system that incentivized otherwise good people to do ethically dubious things (as Sam Harris speaks about in Lying), but it’s still core to my beliefs that both parties in a negotiation should feel they’re getting what they need from the deal, and I’m not sure I can say that about my employment relationship.

The second is feeling “in orbit” around a planet you don’t want to visit. Money is gravity, and even if you’re not physically in the office every day, every day spent yoked to the destiny of people you don’t want to be in business with is a spiritual drain.

So it was with a giddy sense of relief that I walked out of my office.


If I’m not taking a paycheck, what am I doing? Well, I’m hopefully growing my business to meet the need by the time the Deadline comes. I’ve weighed my options a million times, and run the whole situation by some very smart people, but in the end it came down to my gut. As Gary Vaynerchuk says, “you should leave when you’re suffocating.” If I was nervous about the outcome before the meeting, afterward I realized I couldn’t have taken another day. If I were writing the movie of my life and I could choose the most optimal day, armed with all I know about the viability of my business(es) and the bandwidth-opportunity-costs of being employed, it’s hard to picture a better day than two weeks ago this Wednesday.

My business has grown, mostly through trial-and-error. There are only three ways to make more money. More customers seeing your offer, more of the customers who see your offer buying, and each customer spending more. All the mumbo-jumbo on the podcasts boils down to that. I’ve been pulling firmly on each of these levers for months. Sometimes an intervention will make things worse. Other times, it will make things better. Know the difference between the effects of your interventions and random chance, then do more of what’s working. I’ve done just enough to see the trend lines headed the right way. The only other question is market size: if I capture all the demand in my market, will I “top out” and reach a glass ceiling. I’m reasonably certain that’s not going to be an issue.

Please don’t mistake the acceptance-of-my-fate in this post for arrogance. I fully expect to sweat between now and the “deadline”. To pound the table. Realities like health insurance have already intervened. $600/month for a decent plan. Picture shouldering that, and feel the knot in your stomach. Picture that lump sum you’re used to seeing in your bank account every first-of-the-month not there anymore. Run your eyes down the imaginary spreadsheet of your monthly expenses. Then think about everything you hoped to do this year. Travel, ….hmmm – mostly travel;) Then think about emergencies.

“What’s the worst that could happen, and what could I do then?”

Well, I could probably stay on with the company if I agreed to the rules a little better. I could take an apprenticeship. Slightly up the totem pole, I’ll continue to float consultancy proposals. This is assuming the worst-case-scenario: my business doesn’t grow a bit. Even in that case, there’s still ample opportunity to pay off my debts and save a little before the “deadline”, which will reduce my monthly expenses.

But I prefer to spend my mental energy focussed on how to improve the Right side of the ledger. (As a friend recently said “if your dream isn’t coming true it’s probably because you’re too focussed on its absence and not focussed enough on its presence”. ) And I’ll write a tactics post (similar to several I’ve already posted in my entrepreneur group) soon.

The meta-point is that, as far as I can tell, existing in this space of risk-mitigated uncertainty seems to be what Freedom, and maybe Adulthood, tastes like.

* I should mention I’ve zero real-life experience with meddlesome parents as both my parents and my in-laws are astonishingly supportive.