Here’s a story that I often tell people, and it’s useful enough that it’s worth writing up to share with more people.

I started my first real adult job in early 2013, working in marketing for a software company. I think both my ex-boss Dinesh and I would describe myself similarly: 22-year-old Visa was a smart young man– good writer, ambitious, occasionally brilliant, but also nervous, muddled, not very self-possessed, easily distracted, struggling with both perfectionism and remarkably basic executive functions.

(everything I write in the following recollection is my personal recreation of events. Some of it may be semi-fictionalized thanks to the vagaries of memory, but I hope I got it true in spirit. The reality was a bit more tedious and clunky.)

One day, still early in my career, I was late to a meeting. I can’t remember the precise specifics of how this played out – I think it was in one of our regularly-scheduled 1-1 meetings afterwards – Dinesh asked me, “Hey, why were you late for the meeting?”

I sighed internally. Right, I fucked up, it’s time to perform contrition. Up until that point, every such conversation I had had with anybody in my life – parents, teachers, peers, and even myself – had followed a fairly predictable script: people don’t actually care why you were late for the meeting. You failed, and failure must be “dealt with” in some form, and that typically meant punishment. I started mumbling, “Oh I’m sorry, I messed up-“

Dinesh casually waved that off. “I’m not looking for an apology, I’m just looking to understand. Why were you late?”

I was confused. If he was looking to punish me, this was a rather elaborate theatre he was setting up! But that didn’t seem anything like the geeky, somewhat shy, somewhat soft-spoken older nerd I had been getting to know over the preceding weeks. Did he… just want details? I suppose that was plausible…

“Well, I woke up late… because I went to bed late…”

“You knew you had a meeting in the morning, right?”

“Yeah.”

“So why did you go to bed late?”

God, this was excruciating. I found myself wishing that he’d rather insult me and call me names. Instead he wants details?

“I… I was playing video games and I lost track of the time.”

“Oh, okay. Maybe next time set aside time to play video games, so that you can go to bed on time, so you can make it to meetings on time? Assuming that’s a priority for you, of course.”

It was. What’s hard to convey in this standalone story is that Dinesh and I had many long conversations about all sorts of topics – he had read my blog before hiring me, and so he had quite a bit of insight into my personal psychology and motivations. (This might sound horrifying to some people – but for me, it was exactly what I wanted. I wanted to work with someone who knew what I was about and where I was coming from.) I wasn’t just looking for an easy paycheck – I wanted to be a valued member of an excellent team doing good work, I wanted to become a man of my word, I wanted to be reliable and effective. I just… had a habit of staying up late at night. I needed help, and I wasn’t quite able to ask for it. I wasn’t quite able to face the truth of the problem that I had.

Clarity and compassion

A decade later, I can look at this story with much more clarity and compassion. We now have pithy phrases like “revenge bedtime procrastination” to explain the phenomenon. I can now see that I had a part of me that was a tyrannical internal taskmaster, demanding that I work constantly, and another part of me that rebelled against that. This internal conflict played out at a largely subconscious level, and I found it embarrassing to reveal it to anybody else. And yet, ultimately, it was only by sharing it with someone I trusted, that I could find my way out of it.

At some point Dinesh suggested that I could set aside time on my calendar to play video games, which was mindblowing to me as a concept. Nobody had ever earnestly suggested anything like that to me before! I had internalized a truly tormented idea which went something like, “If you haven’t finished your work, you’re not allowed to play, have fun, or rest. How dare you. Only a selfish, evil person would do that.”

And so I was miserable all the time. I would have to sneak away from myself to have any fun, and that fun felt horrible, too – what Tim Urban described as “the Dark Playground” – the kind of guilty, stressful fun that you have when you know you haven’t earned your leisure, that you’re violating your own self-respect. It was really bleak, and I think it led to actual depression at some point while I was working through it.

Once wasn’t enough

I wish I had a super cheerful feel-good ending for this story, like that one conversation was enough for me to swear off revenge bedtime procrastination, and that I was never late for another meeting ever again. Alas, reality isn’t a fairytale. It wasn’t enough! I made an effort, but I kept being late still.

What amazed me was that Dinesh never wavered in his persistence. He kept asking, gently-but-firmly, “why were you late this time?” And I would have some other excuse – “oh, I stayed up late for some personal stuff, not video games, and I set an alarm, but…” , and he would patiently-but-persistently keep asking, “What do we have to do so this doesn’t happen again?” I kept “waiting for the other shoe to drop”, thinking “oh, right, this time he’s going to get mad, and then we’ll do the anger-and-contrition dance”.

But he never got mad. I recently asked him how/why, and he said something like, “perhaps I’m extra introspective and I care about the epistemology in the company I’m running… but really the critical thing is probably that I was actually incentivized by the context we were in, had skin-in-the-game, to actually be curious about actually solving the problem.”

Strive to be genuinely curious

Old habits die hard. It takes time and repetition and kindness to install a new way of thinking, a new way of being. And you really have to get into the root of it.

I do think I’ve gotten significantly better at it over the years, but I am still, 10 years later, always at danger of slipping into old patterns. But when I do, I find myself thinking about Dinesh’s gift of gentle, persistent curiosity. I now ask myself questions like, “why am I really doing this? what do I want to be doing? what am I avoiding? what am I afraid of? how can I be fair to myself?” Most recently, the note I have pinned to the top of my notes app says, “does withholding rest and leisure increase your productivity?” Reader, it really doesn’t. That’s not sustainable beyond like, a grindsome weekend, or maybe a month if it’s a really big and intense project. You can’t live like that without getting burnt out. And recovering from burnout is a lot less fun than enjoying a vacation, spending time with loved ones, or doing the things you love.

And I’ve found, amazingly, that scheduling leisure makes it easier for me to get work done, than treating myself like a soulless worker drone. When I’m reassured with the knowledge that I can trust myself to let myself have fun later, I can work without feeling like the walls are closing in around me.

I’ve often found myself sharing this story particularly when hearing people, especially young people, talking about their own internal taskmasters. They don’t typically realize that that’s what they’re doing. They typically describe the anguish, stress, fear – the walls closing around them – without realizing that they are the ones doing it to themselves.

I’m not saying “it’s all in your head” – we do live in a society, and the taskmaster functions as a sort of intermediary/broker/interface. We often learn to self-flagellate because at some point we had lived amongst people who demanded remorse, or worse, were outright punitive. We then tend to overindex on those early life conditions – a vindictive parent or teacher can cast a long shadow that haunts someone for the rest of their lives.

But you don’t have to remain in that shadow. You can seek out and experience different environments. You can find peers who will challenge you in gentle yet persistent ways. You can learn to stop being late for meetings. You can learn to stop bedtime procrastination. You first need to believe that that is possible. You then need to understand the real reasons for why you do what you do. And then you need to address the root causes. All of that is a little more complicated, I wrote a whole book about that and will likely be writing followup essays.

But it all starts with seeing what is really going on. If I’m lucky, maybe this story may have helped you see something about your own life with fresh perspective.

For a final note I’ll defer to Dinesh: “I think the key point is to find a place where the self-actualization of your unique abilities is real skin-in-the-game for the counterparty. In our situation, we had some outlier behavior in me (epistemology) and you (curiosity about yourself, take people and what they say seriously), so things accelerate when you have those.” (EDIT: a couple more tweets on the topic from the man himself)

So what would be actionable for you, if you’re in this sort of situation like I used to be? First thing I would say is “Read Introspect, I wrote that whole book for you”, but secondly, as Dinesh says – try to seek out environments, contexts, peers, mentors, where other people are incentivized to help you actually solve your issues.

I have a couple of other followup reads here if you’re interested:

• How I rebuilt trust in myself (2020)
• Notes on ADHD (2021, ongoing)
• Beware self-flagellation (2016)
• Beating yourself up is egotistic (2016)

Also, subscribe to my substack! I’d start with reading Are you serious? (2023)