Michael Ashcroft

Thinking Out Loud No. 51 // Tuesday 08 February 2022 // 8 minute read

Wholeheartedly limiting my options thanks to Deep Okayness

It’s been a while.

The last time I wrote to you was on 2 November last year, when I told you I was embarking on a year of nomad travel.

Well, as I write this, I’m on the plane to Mexico City, currently over Lake Superior from the looks of things.

Genuine photo of in flight screen thing

What I’m doing hasn’t really sunk in yet, if I’m honest. Sure, the last week involved a frenzy of packing, saying goodbye to friends and family and savouring our final moments in London for who knows how long. But it’s not like I’m actually going to be living in Mexico for the next three months, right?

Actually, yes, it’s real. It’s happening. Adventures await!

Why haven’t you been writing, Michael?

Seasonal depression, mainly.

It happens every year, and even though I’ve become familiar with it and know it’s coming, I’m still caught off guard by how the structures of my life collapse between December and February. Turns out that sunlight is pretty important.

So it was that, and also that I managed to score a wonderful own goal that blocked me for a while. In the last newsletter I announced a pre-sale of a course course Playful Creativity, which I want to make "because I want to help people unlock the natural, sincere and earnest capacity for play that I believe is our birthright."

And then — surprise! — I suddenly didn’t feel able to make the course, playfully or otherwise. Turns out that feeling like a fraud doesn't make you want to do the thing!

In fact, given this experience of inner conflict and shame around this, I’m actually confident I can do a much better job that I would have had I made it when I said I would. If you’re interested, you can read how I’m getting myself out of this hole in this article for the case study I’m doing with Rob Hardy.

All this to say that there have been some blocks, and those blocks are going away. And some, permanently, I think! Big claim, I know, but I think that’s just what Deep Okayness feels like now.

I’m gonna be writing a lot this year.

Although, wait, hold up — Deep Okayness?

I, too, appear to have attained Deep Okayness

I’m now over somewhere called “Dubuque”, which I choose to believe rhymes with Albuquerque.

There’s something pretty magical happening on the Internet. Normal people are smashing together various psychotechnologies and radically changing their experience of themselves and the world by cultivating a way of being that feels Deeply Okay.

I didn’t coin the term Deep Okayness, that was my friend Sasha. If you haven’t encountered his post — “How I Attained Persistent Self-Love, or, I Demand Deep Okayness For Everyone” — it’s well worth your time and attention.

Deep Okayness is not the feeling that I am awesome all the time. Instead, it is the total banishment of self-loathing. It is the deactivation of the part of my mind that used to attack itself. It’s the closure of the self as an attack surface. It’s the intuitive understanding that I am merely one of the apertures through which the universe expresses itself, so why would I hate that? It’s the sense that, while I might fuck up, my basic worth is beyond question—I have no essential damage, I am not polluted, I am fine. — Sasha

This is not the place where I talk about how I did it, just to note that I did.

There is a distinct before and after to my experience. Where before there was a core of ‘bad’ and some level of self-aversion that manifested mainly through a nebulous sense of shame… now there is just… largely not that.

It’s not completely gone — I don’t think my experience is yet as strong as Sasha’s, but, like, that mind-turning-on-itself-and-creating-bad-feels thing is 80-90% missing. And life feels radically different, as though I was playing on the heroic difficulty setting before and just discovered that easier modes are available.

Okay, I’ll give you a sneak preview of how. Sasha says it himself: “find ways to bring more of yourself into loving awareness.” And, in particular, those parts that you couldn’t possibly believe are worthy of any love at all, let alone unconditional love.

More on this to come, obviously.

What if constraints are good, actually?

Now that I seem to have a stable sense of Deep Okayness, much of the world looks different. Things that seemed scary and bad before now seem inviting and good,

One of those things is ‘constraints’.

It feels like there’s a particularly Millennial mindset around wanting to have it all and keep options open. Each time we close a potential life path, a voice inside lets out an anguished scream, as if raging against an unseen oppressor.

I have very much been this person. The idea of staying in one job, in one place, in one relationship or, god forbid, having kids, has always come with a pang of resistance. It’s not that I was obviously avoiding these things or living as an unattached vagrant. I found fulfilment in those frames, I just didn’t  picture any of them as being final, although neither did I picture them as being not final either. Basically, my future was left open as a kind of foggy superposition of nothing and everything.

This trait had been slowly weakening in the last few years, but since Deep Okayness it feels like the transformation is most of the way there. Where before I may have known, intellectually at least, that long term commitments are probably good, now it feels intuitively right that making irreversible, option-limiting decisions is a vital part of a life well lived.

As I wrote in one of my earliest newsletters, art is made of constraints. Your painting is literally made of acrylic and canvas, and therefore isn’t made of charcoal and paper. You can’t make art without first deciding which media to use — and which not to use. Failing to make that decision results in potential, but no art.

I thought I was being clever at the time in generalising this idea out to my writing, which was made of my limited time available for writing, the lesson being that I should enjoy the kind of writing I could do given that context.

Now, though, it feels like I missed the obvious, grander insight staring me in the face: life itself is made of constraints. Instead of being impediments that hinder our experience of the world, constraints are the scaffolding that allow us to climb to new heights.

I don’t know exactly why the experience of Deep Okayness has brought this to life for me.

Perhaps I truly believe I have the capacity to navigate whatever challenges leaning into these constraints will throw at me. Perhaps I trust that I will no longer turn on myself as soon as things don’t go as hoped. Perhaps I know deeply that I am worthy of the good things that will come by wholeheartedly choosing my constraints.

Who knows. But, honestly, this feels like a much nicer way to be.

How many weeks do you have?

Quickly — without calculating — how many weeks long would you say your life is?

I’ll pause for effect.

It’s about 4000, assuming you live to 77.

How does that feel?

That question is the premise of Oliver Burkeman’s book 4000 Weeks, which I think played a meaningful role in helping me access Deep Okayness.

It’s a short book, ostensibly about ‘time management’, but it’s core message is not that you can become better at managing your time, but that, ultimately, you do not have the time to do all the things you want to.

Going back to my old Millennial fear of cutting off options, Oliver suggests that to _decide_ — a word that has Latin roots meaning ‘to cut off’ — implies the crystallisation of a more narrow set of possible futures that challenges our assumption that we will live forever. That, of course, is scary, so we avoid it.

But we will not live forever. I myself have about 2230 weeks left, I hope.

And with that, from somewhere near Tulsa, I hope you have a great week ahead.


(In actual fact I finished and sent this at around 05:30 local time, because jet lag, that wonderful period where your body says: "yes, we are indeed tired, and yes, there is  indeed time to sleep, but lol, nope,")


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 almost 1000 of us now, come play!