---

However big I ever feel / It’s never enough
Whatever I do to make it real / It’s never enough
In any way I try to speak / Never enough, never enough.

— THE CURE

---

It’s always jarring and mildly insulting to hear that extremely famous and successful people are unhappy with their position in life. You ingrate! How dare you be miserable! Stop appropriating my culture!

The reason I feel betrayed by superstars like Tim Ferriss who talk openly about struggling with feelings of inadequacy is not so much actual class resentment, but the assault upon my own convictions that once I achieve [$NEXTBIGTHING] I will be content with my own position in life.

This is a delusion that persists in the face of vast mountains of evidence to the contrary. Taking the outside view: every time I’ve achieved something in the past, I celebrate for about three milliseconds and then immediately re-orient to the next goal. I notice that this also happens to people vastly more successful than me. But yeah, that next thing—when I publish my book, or notch up 10,000 subscribers—see, that’s going to change everything. This time is different!

The theory of ‘Type A’ personalities was a bunch of hooey funded by Big Tobacco to shift the blame for heart disease¹, but it persists in popular imagination because it gives us an instantly recognisable archetype for a cluster of traits: ambitious, impatient, self-critical, proactive, goal-focused, hard-working, status-conscious.

These are the kind of traits that drive people to attempt hard things. The only problem is, they don’t come with a convenient off button. And so, those with Type A inclinations end up locked into a cycle of eternal impostor syndrome and endlessly ratcheting ambition.

I’m not looking for an off button. But I would like to install a kill-switch, which automatically shuts these drives down beyond a certain threshold.

From Same Salad, Different Day:

I’m no longer interested in perfection, which seems to be a recipe for eternal dissatisfaction and self-flagellation. Instead, I want to get to the point of ‘good enough’ in each area of life, and leave it at that.

James and Zach and a couple others picked up on this throwaway line and asked me to write more. So here we are.

This is a hot topic among a bunch of people I know, so the timing is good. Just be warned that this post is more self-indulgent than usual, and will probably only make sense to the extent that you relate to the Type A archetype.

---

Reverse Life Coaching

I am too lazy to be a full-blooded Type A. One of my best friends has got it much worse than me: after several gruelling years building a successful company in a cut-throat industry, she sold the business and finally took a proper vacation—which, of course, she abandoned half-way through to dive straight into the next bigger-and-better thing. She’s a successful businesswoman by any definition, but she still feels like a little kid. It’s not enough, and all the signs suggest it’s never going to be enough.

Now we are embarking on a kind of Reverse Life Coaching: a shared ambition to become less ambitious. I will lay out the plan at the end of this post. I think it’s going pretty well.

First, three recent events that suggest this is a solvable problem.

---

1. Very famous people can rein in ambition

Alain de Botton has a bleak view on self-help, fame, the capacity to be fully psychologically healthy, etc. It kind of bummed me out to discover he was dead serious about all the stuff he wrote in his new book (sample quote: “Everyone, seen close up, has an appalling amount wrong with them… the only people we can think of as profoundly admirable are those we don’t yet know very well.”)

Then, right at the end of our conversation, I asked if he had personally reached the point of ‘enough’. And a ray of sunshine burst through the clouds:

That’s a really good question. Without wishing to sound arrogant or self-satisfied, I have reached the stage of enough, yes. I’m really happy. You know, I’m turning 50 at the end of the year. And I’ve written some books. And I’ve been around the world a few times. And I feel very grateful. I don’t need to achieve in the way that I felt I needed to achieve when I was 20. And I think that’s fine.

One the one hand, this is really heartening. On the other hand, de Botton is a rich and famous and brainy author who has dedicated his career to thinking about this stuff, to the point where he wrote an entire book on status anxiety. What hope do the rest of us have?

---

2. People on the verge of fame can step away from the ledge

Somewhat more reassuring: another friend has an eerily similar career and life trajectory to me, but he’s a few years further along. He’s a super ambitious Type A, but is using meditation and introspection to hack himself back to sanity.

Earlier this year, he wrote what I thought was a brilliant book proposal. He had a world-class agent repping him, the topic perfectly captured the zeitgeist, and the project would quite possibly have catapulted him to the ‘next level’. All the wheels were turning.

Then he decided to bow out. He chose to be content with what he had, spend more time with his loved ones, get outdoors more. To maintain equanimity, instead of chasing status. Here’s how he explained it:

I guess what I’m realizing is this: I don’t need to do or become anything in order to be OK. Everything is always already OK.

That’s the level I want to get to. 

We went on a pub crawl on Lime scooters (because Portland) and he literally made me stop to smell the roses.

---

3. I have (partially) managed to rein it in

Most reassuring of all: in the course of emailing someone puzzling over a similar dilemma, I realised that I already feel perfectly content in certain areas of life. 

Specifically: fitness, and finances. In both of these domains I’m a long way from exceptional, but comfortably competent.

I still enjoy trying to up my calisthenics game, but I’m never gonna get on the level of the Barstarzz guys. That’s okay! In fact, if I never manage to get any fitter or stronger—if I’ve already peaked, and this is as good as it gets—that doesn’t bother me in the slightest.

Same goes for finances. More money would be nice, but it hasn’t motivated my decisions for a long time, and I don’t care if I never become a millionaire or whatever. Money is only instrumental to my actual underlying goals, and I’ve already carved out pretty much the exact lifestyle that I want.

In other words: I’ve reached the point of ‘good enough’. This gives me hope for other areas of life in which this is absolutely not the case.

---

‘Enough’ Metrics

Here’s the plan: in each domain, I’ve come up with concrete ‘enough’ metrics—baseline measures of success that I have to be satisfied with for the rest of my life. Every quarter, I’ll check in on them, and update the spreadsheet. So long as I stay at or above ‘enough’, no action is required: no goals, no ambitions, no self-flagellation.

It’s fine to go above and beyond, but only for shits and giggles. I’m not allowed to stake anything important on it. The idea is to draw a clear line in the sand which says: ‘relax already, you made it.’

Some examples:

Once the metric turns green, there’s nothing to do. So you can see that I’m not quite there yet on sleep or VO2 max, but everything else in this section is fine.

Coming up with concrete metrics was easy enough for the likes of finances and health.²

It’s much harder for something like ‘impact’ or ‘writing skill’. There can’t be any ambiguity, or the goalposts will keep shifting (am I a ‘competent writer’? Not yet, maybe next quarter…)

And, of course, they can’t all be slam-dunks.

I was telling someone about my plan and he couldn’t relate at all. He had the opposite problem: he wished he was more ambitious, and less relaxed.

This was so alien to my perspective that I hadn’t really considered it. Embracing mediocrity might lead to complacency? Oh yeah. Different people sometimes need to hear the exact opposite advice.

So, each metric has to be low enough to avoid constant dissatisfaction, but high enough to avoid complacency.

Which raises the question: exactly how good is ‘good enough’?

---

The Low Bar for Good Enough: Merely Not Sucking

It might be rude to say this in the age of ‘participation medals for all’, but radical self-acceptance seems like a bad idea to me.

You probably shouldn’t just accept yourself exactly as you are, because… what if you really do need to get your shit together? If you suck, and you know you suck, maybe you should try to suck less.

One of the interesting bits of de Botton’s book was his critique of the Romantic idea that we should love unconditionally, without wanting to change the objects of our affection. Apparently this is a major departure from the old school:

For the Greeks, given the scale of our imperfections, part of what it means to deepen love is to want to teach – and to be ready to be taught. Two people should see a relationship as a constant opportunity to improve and be improved.

When lovers teach each other uncomfortable truths, they are not abandoning the spirit of love. They are trying to do something very true to genuine love, which is to make their partners more worthy of admiration.

Again, not sure if you’re meant to say this out loud, but my love is conditional: for others, and for myself.

Fortunately, the bar is set nice and low!

Having ploughed through an embarrassing volume of self-help literature recently, my impression is that the best advice is remedial in nature. It gets you from ‘sucking’, to ‘not-sucking’. Once you’re at baseline competence, you start to run into diminishing returns. Any book that makes grandiose claims is invariably based on cherry-picked examples, or blatant Law of Attraction-style woo. Achieving spectacular success mostly comes down to a ton of domain-specific hard work, and a lot of good luck.

But that doesn’t matter, because merely not-sucking is an uncommon victory! To put it in the language of optionality, capping the downside is much more important than hunting for black swans (and much easier, too).

If you get to the point of not-sucking, or even ascend to the hallowed ranks of mediocrity, I think it’s okay to pat yourself on the back and leave it at that.

Where exactly you draw the line depends on what it takes to live with yourself. For me, it’s quite a bit higher than merely not-sucking, but a long way below ‘perfect’. Say, somewhere around the 90th percentile for the things I happen to care about.

And I’m not there yet, outside of fitness and finance. If I experience a little status anxiety, perhaps that’s telling me something useful.

---

The High Bar for Good Enough: Striving vs Equanimity

Being ‘content’ trades off against trying to do hard things. The reductio version would be a monk sitting on a mountaintop in meditative bliss forever: OK, he’s Zen as fuck, good for him, but he’s not exactly doing much to make the world a better place. This is no different to floating in an isolation tank with electrodes wired into your pleasure centre, except as a matter of aesthetics.

On the face of it, playing status games and pounding along on the hedonic treadmill is ridiculous. It’s embarrassing that our supposedly advanced species is still a slave to these animalistic drives. On the other hand, following the desire to impress our fellow monkeys snowballed into this whole ‘civilisation’ thing, which is pretty neat.

This is why I’m not interested in using something like meditation to neuter these impulses just yet.³

At this particular point in my life, I’m willing to let the horny status-seeking chimpanzee stapled to my frontal lobe keep screaming at me, even if it makes me a little less Zen than I otherwise would be, because I want to try some hard things that go beyond the realm of merely not-sucking.

These things are quantified by the ‘Impact’ metrics I cropped off the screenshot from earlier:

I’m keeping the details of these ones to myself, but you can see that they’re mostly orange and red. There is much work to be done, but the kill-switch is ready and waiting in the background.

These aren’t goals, which will immediately trigger another set of harder goals upon completion. Instead, they’ll trigger a firm commitment not to set any more goals.

At the start of the year, I said my ultimate ambition was to have no ambitions. But I wasn’t sure how to actually make that a reality, without risking becoming a useless layabout.

Now I feel like I have a clear roadmap for getting to that point. And it feels good.

---

---

Further reading along these lines:

• Unstriving – A post on optimising for greatness vs settling for mediocrity (Putanumonit)
• Replacing Guilt – A sequence on trying to do hard things (Nate Soares)
• Mediocratopia – A series on slouching towards mediocrity (Venkatesh Rao)
• Status Anxiety – A book on the human need for social approval (Alain de Botton)

---

If you think I’m insane, let me know! If you find any of this relatable, let me know! And if you have examples of your own ‘good enough’ metrics, I’d love to hear them.

---

Notes:

1. It wasn’t the cigarettes killing people – it was that individual smokers must be stressed-out Type A personalities! I am not making this up.

   Type A/B is an artificial binary imposed from the top-down. You might have some of the traits, but not others, and each individual trait within the cluster falls on a spectrum. This is the same flaw as Myers-Briggs, with the same result: it’s armchair pseudoscience, but it does give us some useful archetypes.

   Looking at the Big Five personality theory (which is more legit, and derived from bottom-up factor analysis), the ‘Type A’ cluster would presumably map onto being higher in conscientiousness and neuroticism, and lower in agreeableness.

2. In fact, I probably set too many: chest-to-waist ratio is an excellent proxy for a whole basket of other health metrics (in men), and could maybe replace ‘bodyweight’…this is still a WIP.
3. Also because I suck at meditation.