Friend Milo posted a great video this week about his self-employment fails. It’s very funny and honest.

I like to mention failed escapes every now and then. It’s important to build the prospect of failure into your escape plan so you can hit the road with eyes open. And of course it generally helps to think about how you’d cope if everything went banana-shaped.

Personally, I don’t mind the prospect of failure (which is lucky really) and I always feel that if you have to go back to the office, tail between your legs, at least you’d have had an adventure and stories worth telling at the water cooler. Maybe that’s just my personal idiot optimism.

I had a few questions for Milo based on this vid. So lets ask them why not?

You said you feel proud of trying, which is good. On balance, do you think your time in self-employment was a worthwhile personal adventure? Was there value in simply attempting escape?

Oh yes, it was definitely worthwhile. I learnt a lot about myself. And I learnt a lot about what not to do if I were to attempt it again!

I’ve had a less stable and financially secure existence than if I’d stayed where I was (being made involuntarily redundant in 2020 for example) but I currently have a well paid and interesting job and more importantly, I’m a wiser person overall.

In the end, I definitely don’t regret what happened. It was all part of the process.

Now that you’re back to work, do you feel like a hero or a fool or a bit of both? What do your colleagues make of your antics?

The one disadvantage of having changed my profession a couple of times now, is that I’ve stayed in a relatively junior role compared to many colleagues who are a similar age to me, or even significantly younger. But I’m pretty sure my colleagues don’t give a damn, and I’m far from the only employee to have gone off on career tangents.

I have felt pretty embarrassed about the whole thing though, primarily because I shared my plans publicly and they didn’t quite work out. So I then had to admit my ‘failure’ publicly, albeit to a small audience. So in that sense, I did feel a bit of a fool. I think the Midlife Crisis Diaries videos are partly a way of coming to terms with this embarrassment, which still lingers even several years later. Ironically here I am airing my midlife crisis in a public forum, so perhaps I will never learn!

However, the Fool’s journey in Tarot terms is not a negative thing. It’s quite a positive card in fact, which signifies a leap of faith and an open, playful attitude to life. It’s similar in some ways to the Joseph Campbell’s concept of “answering the call to adventure.”

When you escaped, did you think it was forever or were you already managing your expectations?

I certainly hoped it was going to be long-term. But although I was somewhat arrogant in that regard, I also had the awareness, and the accompanying anxiety, that it might not work out. I was taking a leap into the unknown, so I genuinely wasn’t sure one way or the other.

You quit drinking and found a therapist to do the personal work. Do you think you’d have done those things if you’d stayed employed?

Great question. Not having a 9-5 definitely gave me the gift of extra time to do the work on myself that I needed to do, and also to recover from burnout after ten years of balancing a fairly dreary day job with a ton of (mostly unpaid) extracurricular creative efforts. Plus yes, detox from over-indulgence with the booze. In retrospect, that was a real gift to myself.

Could you have had more success (or simply more fun) if you’d gone all in on your music or filmmaking instead of corporate copywriting?

Possibly, yes. I definitely think I should have given myself six months for a bit of low-pressure creative exploration, instead of diving right into freelance copywriting. Having said that, I imagine I would have eventually come up against the same internal barriers and limitations regardless of what route I took.

I’ve come full circle in some regards, in that I now see the importance of having creative projects that are in the service of my own muse, rather than someone else’s business goals or with the pressure of needing to make a living from them. My biggest regret is that I not only went back to working full-time, but that I stopped doing creative stuff outside of my paid work, and in particular that I let my blog die a slow death. (I’m hoping to resuscitate this somewhat by publishing occasional updates on my substack newsletter which I’ll be launching soon).

You got that big tax bill surprise, which suggests you were making good money. Did you ever try to go super-frugal so that you wouldn’t even need to pay tax?

Believe me, there were frugal times during the four years I was freelancing. But I was on a bit of a mission to prove to myself that I didn’t have to be a starving artist.

I had initially wanted to be an arts journalist, but I’d gotten frustrated by not being paid for my work. For example, I did a significant amount of work for a local magazine in my spare time, but because it was unpaid, it didn’t provide a route out of the day job. I’d also lived on very low wages for a long time, so by the time I started earning a reasonable amount I didn’t want to go backwards in that regard. I turned to copywriting, because I thought I could at least be paid fairly.

That was one of the reasons (as well as narcissism obviously) why I made my story of “ditching the day job” public; I thought it might be helpful to show that being creative doesn’t have to mean being poor. Of course, that backfired somewhat!

I think that one of the main reasons I didn’t succeed though, was not because I wasn’t frugal enough, but because I didn’t charge nearly enough for my copywriting services, due to a lack of confidence. I even had a client tell me I was undercharging them. But I had no clue how much to charge and wasn’t smart enough to reach out to other successful freelancers for mentorship or advice. So, I hope others in the same situation can at least learn something from my mishaps.

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Keep an eye on Milo’s website (and/or the New Escapologist Twitter account) for when his Substack goes live.

21 Oct 2022 No Comments