The Fool’s Journey: A Chat with Milo

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.


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

The Mountains Are Calling and I Must Go

As seen at The Passenger Press in Glasgow today:

The Passenger Press sells lovely hand-printed greetings cards and posters. We’ve bought some of their work before at zine fairs and online.

The quote was familiar so I looked it up when I got home. It’s from mountaineer John Muir. An informative article at Adventure Journal explains:

we should consider the full quote, which appears in an 1873 letter from Muir to his sister: “The mountains are calling & I must go & I will work on while I can, studying incessantly.” These words reveal a man who saw responsibility and purpose as well as pleasure in the mountains. Muir was a master observer who enjoyed the constant work of understanding nature.

I think that’s great and the sentiment is even more Escapological than I first thought. Obviously, “the mountains are calling and I must go” is a great thing to say as you stand up and walk out of a pointless work meeting. But it’s also about conducting yourself with decorum in real life, finding enthusiasm and intensity inside yourself and remaining true to it.

We happened upon The Passenger Press after delivering copies of my book, The Good Life for Wage Slaves to Good Press two doors along on the same street; why not get a copy in person if you happen to be nearby?

Dreamer John:


A sad case of abuse in a private care home made the news this morning. It’s quite upsetting so please don’t feel that you need to read about it but, essentially, the nursing and cleaning staff of a care facility were caught in the act of tormenting and physically assaulting one of their vulnerable charges.

This blog is obviously not a place to talk about such things but we do like to rail against the corporate machine, and what caught my attention in this respect was the corporate care home provider’s official response:

[our treatment of the patient] fell far short of the standards of care we provide our residents every day. We would like to again apologise to Mrs King and her family, and reassure our community that these actions were committed by rogue individuals.

As a learning organisation, in the wake of [hidden camera] footage being brought to us we have further strengthened our complaints process and our safeguarding policy.

We remain committed to doing everything we can to deliver the highest quality care, and to ensuring peace of mind for the residents who make their home with us, and their loved ones.

Fell short of standards of care? A learning organisation? Remain committed to delivering the highest quality care? How are they not ashamed to spout such mealy corporate drivel in such a grave context?

Even in more trivial circumstances, it’s insulting to be offered such an unfeeling, inhumane apology by the mouthpiece of a brand. It’s a technical apology as a matter of process, an output statement of quasi-legalese from an absent party, a false dial tone disconnected from emotion, contrition, or a desire to achieve anything useful in reality.

When a cancelled train leaves me stranded in the middle of the countryside with only an expensive vending machine for company or I’m on a flight that’s been sitting on the Dublin tarmac for two hours, a pre-recorded voice will sometimes come from a loudspeaker to say that “we apologise for any inconvenience this may cause.” I see red when that happens and it’s not even that important. “May cause” indeed.

I’ve sometimes wondered if corporations aren’t perfectly aware of how offensive a phoney apology can be and that it’s precisely why they do it: after all, the employees of a railway company or an airline feel insulted every day — underpaid, disrespected — and, since they have no meaningful interface with the company that makes their daily lives a misery, they take it out on customers in this passive-aggressive way. Saying “we apologise for any inconvenience this may cause” in the midst of a crisis will obviously infuriate. They might as well just say “Soz.”

In the harrowing case of the care home, it’s impossible to accept such a feeble public statement and I hope there are consequences.

How can the words “our shocking acts of brutality” not be part of their statement? Or “the Zimbardo effect clearly being experienced by our staff will be addressed by trained counselors immediately.” Or how about something along the lines of “naturally, we will reduce our nightmare factory to rubble like the Fred West house”?

Maybe I’m asking too much. But you can still sound professional in a sincere apology. And how could you not want to apologise sincerely in a case like this? How can you not want to make real amends for real betrayal and hurt instead of resorting to such skidmarked claptrap as “fell far short of the standards of care” and then pinning the blame on the “rogue individuals” who you formally recruited and trained and paid?

I’d say this is a good example of why care homes shouldn’t be under the control of market forces, but unfortunately they aren’t the only ones guilty of meekly peddling bullshit in the face of grave accusations. Look at the wording of the Care Commission inspection report according to the Guardian:

[they] cut its rating from “good” to “requires improvement”.


[the] “leaders and the culture they created did not always support the delivery of high-quality, person-centred care.”

“Leaders” is obviously the first word that should make the vomit reach your tonsils, but didn’t it strike anyone that “requires improvement” and “did not always support the delivery of high-quality person-centred care” are brutally offensive euphemisms?

My dislike of corporate language is not a knee-jerk or a purely aesthetic one. I’ve come to accept that some businessy terms like “direction of travel” can be quite useful. It’s also possible that certain distancing techniques can keep the emotional heat out of a conversation where rational decisions need to be made. But it can also be used in a cowardly way to obfuscate and to resist responsibility: you can’t come out to the angry and grieving relatives of an abused dementia patient with simpering phrases like “requires improvement” when you should be grovelling to make up for grotesque malpractice.

According to the Guardian, most of the abusive staff have been fired or allowed to resign (shouldn’t they have been referred to the police?) except for one who was put on a training course. This particular staff member was described by the company as a “committed and values-driven leader”. Jesus fucking Christ.


For further railing against corporate double-speak, try The Good Life for Wage Slaves and Escape Everything! (now available in paperback as I’m Out).

An Escapologist’s Diary: Part 67. Napoli

The “what I did on my holidays” entries to this diary are never the best ones. I think that’s because I write them from a mild sense of obligation; since there’s effort involved in travel, I might as well get something (a post!) out of it. Not a great motivation for writing really. Or maybe it’s because I think the eventfulness of a travel experience will translate to a good entry, but it doesn’t. As someone against eventful writing, I should know this.

I’ve always tried, however, to relate these entries back to Escapological lessons beyond the simple “free movement” theme of travel: the attitudes inspired by travel that might be more generally helpful in life, the ways another society can look and how we might emulate that ideal. I think I’m starting from that point of view this time so maybe my Naples entry will be better than, say, this slightly empty one about Berlin.

So we went to Naples. We stayed in the Spanish Quarter, which is part of the crumbly historic side of town. There’s a fancier side of town up on the mountain, which has lovely tree-lined streets and feels more like Paris or Rome, but we had decided to stay in the thick of life. Travel guides to Naples tend to start with “don’t be afraid of Naples’ reputation for crime,” which people also say about Glasgow, which is where I live. So I wasn’t afraid at all.

Read the rest of this entry »

On Quiet Quitting and the Sunday Scaries

Readers have been telling me about Quiet Quitting and, now, the Sunday Scaries.

I didn’t have much to say about Quiet Quitting because (a) I didn’t know there was any alternative to it and (b) because it’s a stupid name.

Quiet Quitting is apparently the idea of attending your work as usual but “checking out” and doing as little as possible with minimal enthusiasm. You probably meet your contractual demands well enough not to get fired, you turn up to meetings, but you generally just drift through the day in a zombie-like haze. I’m pretty sure that’s nothing new and is in fact most people’s experience of office life. It’s basic survival because to engage in the crap you’re supposed to be doing is mental death. And nobody decides to Quiet Quit; it just happens automatically because of boredom and being asked to do things against your will.

The name, “Quiet Quitting,” annoys me because reporting to work in a zombie state is anything but quitting. It’s doing what you’re told no matter what. If only I were the Mayor of Naming Things, this would be called “The Obvious Result of Wage Slavery” while “Quiet Quitting” would be reserved for the act of finding the guts to leave your job without ceremony or fuss.

So that’s Quiet Quitting dealt with. What next? Oh yes. The Sunday Scaries. This is the experience of feeling anxious on the weekend about returning to work on Monday. Once again, it’s not new and the name is stupid. The name is stupid because it’s willfully infantile (with a similar numb-nut cadence to “the terrible twos” or “sporty forty” or to those banal workaday hashtags like #ThursdayThoughts) and therefore makes light of something ruinous to our quality of life.

The bottom line is that if you’re off work and not currently on the clock, you should be able to live freely in those scarce and hard won moments. But that’s impossible because the psychic toll of work is so great. Having a job is like having someone standing behind you all the time and clanging two iron poles together: you can’t relax under those circumstances. You think about work all the time: at weekends, at night, on vacation, at Christmas, on your birthday, on a hot date, on the toilet, and in your dreams.

The Sunday Scaries have at least been investigated somewhat and the finding is that they:

regularly affect more than two-thirds of Britons who report work stresses, lack of sleep and looming to-do lists as the primary causes of anxiety before the start of the working week.

The worst affected were young adults with 74% of those aged 18-24 experiencing what psychologists call “heightened anticipatory anxiety” as the weekend comes to a close.

So almost everyone then. Well done, Civilisation. We’ve built a world where almost nobody can enjoy their hard-earned downtime for fear of being cattle-prodded back to work again. We’re not compensated for this stress and we shouldn’t have to endure it.

When they experience the Sunday Scaries, people apparently resort to social media, TV, and comfort eating: all things that exacerbate the problem of low quality of life and delay any hope of escape.

A psychologist who probably means well says that instead of wasting your time and brain in these ways, you should:

try getting active, which can help you to burn off nervous energy, writing down or keeping a diary of what you are doing and how you feel at different times to help identify what’s causing anxiety and what you need to do to help manage it. Small things can make a big difference to our mental wellbeing.

Anything but try to change your actual circumstances. Anything but try to escape your job or the consumer treadmill that benefits from your misery.

Luckily, the UK government is on hand to help. Yes, the same government who want to increase work and crack down on “slacking.” So they have a ridiculous (and naturally very cheap) campaign in which people can visit a website for:

a personalised “mind plan” giving tips to help deal with stress and anxiety.

Allow me to be the first to say, “ew, gross.”

This government aren’t there to help you, folks. They’re there to cajole you back into the workforce and, when you complain about the misery of it, they’ll find a cheap way to shut you up.


Tired of hearing the same old crap? Read The Good Life for Wage Slaves for survival tips and then learn to escape with Escape Everything! (aka I’m Out).

A Whole World Out There

This is from Lauren Elkin’s Flâneuse, a good book about walking in cities and its relationship with personal freedom:

There was a whole world out there and I didn’t have to live in America simply because I was born there. I could live anywhere I liked.

This was an epiphany. One rainy night over a pasta dinner with my flatmate, we contemplated the enormity of it. We can go anywhere, we can do anything, we told each other.

She goes on to say “but it wasn’t true” because there are complications with visas and borders, challenges around finding income when you live abroad.

As someone who has had the same epiphany and then struggled through the same problems, I’d say it’s better to contemplate the enormity of your freedom in adventurous good faith than to deny it in bad faith just because it can be difficult.

To start with, you can go to a lot of places for six months without any kind of visa woe. Like Rolf Potts, you can save a battery of wealth from perfectly conventional employment and use it to escape for just a little while or to buy time while you figure out how to escape more permanently. You can travel across multiple countries in Europe or states in America in a state of constant motion without worrying about visas at all. Other places, where visas are a problem, you can still work intelligently and patiently to, you know, get the visa.

Elkin herself is an American who lived in France for several years as an academic. She went “home” to New York when her Paris work contract was not renewed, but she still lived abroad legitimately for years. She lived in Toyko for a while too, under the spousal sponsorship of her partner who was offered a job in finance there.

Getting a visa for my Canadian partner to live with me in the UK was an anxiety-producing nightmare but (a) the UK is particularly troublesome on that front (I had less difficulty with my visa in the other direction), (b) we were asking for rather a lot compared to someone who just wants to live abroad for a year or so, and (c) we won in the end.

I do not deny the awfulness (awfulness!) of the artificial barriers to moving around freely–like Rutger Bregman, I’d prefer to see a borderless or soft-bordered world–and we all know that many of those barriers are getting less and less permeable. But to assume you’re not free to live wherever you want and do whatever you want is to live in bad faith. Do it! Be fleet of foot! Walk through walls!

My partner and I, when moving around between the UK and Canada, did everything by the book, but you could just go somewhere anyway if you feel bold enough. Millions of people move around the skin of the planet illegally or by bending the rules. Momus lived in Japan for years by going back and forth on renewed tourist visas. When one of his visas was coming to an end, he’d go to Europe to work for awhile or go travelling to somewhere like Korea, returning to his girlfriend’s apartment in Japan on a fresh tourist visa for another six months. It came to an end eventually but nothing bad happened to him. And even now he remains a British citizen living in Paris and Berlin without much care for formalities. Heroic.

(Lauren Elkin’s book is great, by the way. I might say more on it sometime but for now I’ll just say that it’s a great addition to any flaneur’s personal library).


For tales of visa woe, please try The Good Life for Wage Slaves. For more positive exercises in good faith and meditations on the enormity of human freedom, try Escape Everything! (a.k.a. I’m Out).

Latest issues and offers


Issue 14

Our latest issue. Featuring interviews with Caitlin Doughty and the Iceman, with columns by McKinley Valentine, David Cain, Tom Hodgkinson, and Jacob Lund Fisker. 88 pages. £9.


Two-issue Subscription

Get the current and next issue of New Escapologist. 176 pages. £16.

Four-issue Subscription

Get the current and next three issues of New Escapologist. 352 pages. £36.

PDF Archive

Issues 1-13 in PDF format. Over a thousand digital pages to preserve our 2007-2017 archive. 1,160 pages. £25.