Michael Ashcroft

August 26, 2021 10:42

Quitting my job was a no-regrets move

I want to share a mental reframe I made that gave me the push I needed to quit my job and head out on my own.

Photo by Denny Luan on Unsplash

In September 2020 I was toying with the idea of making an online Alexander Technique course. I pre-sold 50 spaces to test interest, before I had made anything, and when 50 people bought it I became more confident that there was something there. I was further comforted when they seemed to like what I ended up making.

But there’s an enormous difference between making $5k on the side and quitting your well-paid job to build and scale an online course and, hopefully, make some decent money from it. Such an enormous difference, in fact, that I grappled with whether or not I should quit for two torturous months.

Emotionally I felt ready to quit. I wasn’t enjoying my job and I was excited by the prospect of a new life, yes, but I couldn’t rationalise it. My intellect and my body were pulling in different directions. 

This resolved almost miraculously when I went through Tim Ferriss’ Fear-Setting exercise, based on the Stoic practice of negative visualisation (premeditatio malorum). The exercise goes as follows:

Page 1 - mitigate the downside

Make three lists, with 10–20 entries each.

Page 2 - explore the benefits of action

Make a list of the possible benefits if successful or partially successful.

Page 3 - cost of inaction

Make three lists of the costs of your inaction. In other words, if I avoid doing this thing what might I miss out on?

All of this was useful and I’d recommend the exercise to anyone considering a big decision. 

One of my possible benefits of even partial success was that I would end up with some kind of online Alexander Technique course for which some people would want to pay some amount of money.

I’ve written that nebulously on purpose — who knows what it would look like or how much they would pay? It doesn’t matter, I had already proven that there was some value and some people were willing to pay something pay for it. It stood to reason that I could build something, an asset, that could be sold again and again.

Here’s the no-regrets part. There’s a scenario where I didn’t make enough money from the course to live comfortably and would have gone job hunting again. But I would still have had the course I made! The course that some people would want to buy for some amount of money! None of that would go away.

This means that I’d be returning to the job market in a different position from how I left it. Depending on the level of revenue the course could generate, I could go after different kinds of jobs! Perhaps a part time job, perhaps a comfortable 9-5pm job, perhaps an intense job at a non-profit that can’t pay high salaries. 

Even within the the conventional world of work, an entirely new landscape of flexibility opens up by having a meaningful secondary income stream. This is why a failure to be able to survive entirely independently could still have life changing impact. 

When I recognised this truth the decision was made and I resigned a few days later. 

Incidentally the course has now made about $80,000 since that initial pre-launch in September 2020, most of which was generated in the six months since I actually left work. I’m calling this a success. 

And the best thing is that the logic above still applies: I can still go and get a job if I really want to. But now I also have an asset that looks like it could generate $100k+ a year by itself. This is a nice place to be and it came from recognising that the leap I was about to take wasn’t actually as scary as it felt.

If you liked this then you might also like these:


I HAVE A NEWSLETTER!

I publish a newsletter called Thinking Out Loud, which chronicles my journey as an online maker of things, but it's also is where I talk about whatever I'm interested in at the time.​ There are 900 of us now, come play!