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I literally sat down last spring and focused on this problem with a bit of brainstorming and philosophizing.

My goal was to figure out what parts of me added up to being a coherent whole as a person, at least w/r to career. (With other aspects, too, but mostly "what should I spend my time on, really?")

And this kind of thing is never wholly about skills, interests and talent - they are starting places, but personality and natural tendencies were a much bigger factor in my judgment.

And it helped. I found some insights about what I could/wanted to do, my personal principles, and how I might put these things together in the form of a career - like, ah, yes, I like teaching things and advising, but no, I don't want to do it in the form of formal education. And so on, probing different aspects of the process and teasing out what was most and least painful and working towards "mostly painless so that I can really focus on perfecting it".

Then over the summer I tested out some of these ambitions and found where I was and wasn't limited - like, if I wanted to teach, could I do it by streaming? After working through the logistics I realized that I had something more like lectures in mind, which would communicate better as video. Then looked into video editing and polishing up my voice work and realized that I needed more than one format to do everything I wanted. So I decided that I would have a "multimedia blog" with writing coming first, but lots of images and supplementary content.

So I started on that, and have posted a few articles and shared them(mostly with friends). I don't post at a high rate but it is proving to be a good way of directing my writing energy away from comments like this one(hmm...)

Since the season has changed, I'm probably due to try evaluating myself again and looking for another way to inch forward and focus on what topics and techniques I'm meshing well with.

Wow. I understand what you mean completely, in my gut. The feeling of throwing yourself into something completely, not to better yourself or to prove anything, but simply because you must, is probably the greatest feeling in the world for me.

I used to be like this when I was younger. I remember spending my summer break in my room learning a 3d modeling software just to make some stupid animations... It was this internal drive that I want to accomplish this that waned through the years I think

> I really love stories about people who become totally, utterly absorbed in something, to the point where they obsessively spend time on it, in a kind of natural sense that does not require checklists, reminders, etc. It's just always their top priority, like an addiction, except with meaning and depth.

This is precisely why I avoid checklists and reminders, unless it's for collaboration purposes, events, or managing tasks for team based projects

If I need a checklist for a personal project, this means I haven't built an obsession over something I really want to do.

The fastest way to build an obsession is just to rapidly explore as many topics as possible, and document things at a shallow level continously. Eventually you'll come across bits of metadata you left behind, realizing that you had already looked into this once before, maybe you should consider deep diving. This could be forked github repos, likes on videos, buying electronic parts and building shitty DIY projects lying around, music you've learned, etc

I think there’s a distinction between skills that you think would be cool to have (like learning a language), and areas that you feel drawn to.

I realise this is a difficult thing for most people to tap into. But I’ve thought about this, and I think that most of my “obsessions” have come about after seeing someone else doing something poorly, and thinking to myself “I bet I could do better than that.” If I follow that initial curiosity through, it often turns into a full-blown obsession.

Finding your own 'triggers' is really important, I agree.

For me it's when I can provide help to someone. I'll easily not get anything done for a week, hear someone struggle with something that I could solve with a bit of code (often gluing various API's together), and I'll get right at it.

I'm also triggered/motivated by 'optimizing' stuff in my life. If something in my life strikes me as suboptimal and some code might be able to fix it, I'll happily try to find the least effective but most educational or fun way to solve the problem (XKCD be damned[1]). My life is filled with the coding equivalent of rube goldberg devices, and it's almost a shame that nobody can actually see them.

[1]: https://xkcd.com/1205/

> Is that true or am I just intellectually lazy?

I guess it has to do with education too. If at some moment in your formative years you were taught that obsessing about anything is bad, then that idea can be still lingering below.

> in four decades of living on this planet I don't think I've ever come across anything that fits that bill.

Keep looking! But also, it's possible at 40+ that you may have already found it. Perhaps you've not given that thing the chance it needed for you to fall in love with it — the days and weeks of exploration and the obsessive iteration mentioned in the GQ article that it takes to grok something and absorb it until it feels like it's yours.

I'm almost your age and now rewinding my career path. I kept chasing different tech career paths hoping to find something that “fit the bill”, which only showed me that nothing was as interesting to me than what I started my career doing (game design/animation). It took a couple of changes to realise that:

- Reflecting on how I spend my free time and time on social media, and the speakers and personalities I'm fascinated by and naturally drawn to. (They are mostly game designers and devs.)

- Looking back at the work in the past that has made me happiest and most fulfilled.

From there it was a case of having the discipline to commit to it — I spend most mornings and evenings skilling up and having fun with game design and development, although my day job is still in front-end right now.

On the motivation side of things you mentioned, I don't think it's a case of “find the right thing and you'll find your motivation.” It's more a case of discipline, projecting your self now to your future self, and knowing a few psychological techniques. A couple of things have helped me with that, and they're at opposite ends of the “mind trick” spectrum:

1. Jonathan Blow (designer of Braid, The Witness, owner of Thekla, Inc) has several videos about dealing with lack of motivation that are worth watching:

- https://www.youtube.com/watch?v=i7kh8pNRWOo

- https://www.youtube.com/watch?v=ECwHZlvvVH4

- https://www.youtube.com/watch?v=ryB_VQ__KeE

The pace is slow because it was delivered as a live stream and not a rehearsed talk, but stick with it — he has some great tips about becoming self-aware in order to recognise and reverse the more moderate feelings of malaise that are commonly experienced with any creative work.

2. Jocko Willink (retired Navy SEAL) has a good podcast dealing with motivation, discipline, and committing to your thing:

- https://www.youtube.com/watch?v=yoEv5PxrDvs (a compilation of “best of” clips from his podcast).

With Jocko, I had to fight the urge to close the tab — it can be hard to stomach “just do it” pep-talks that feel like an audio embodiment of those motivational posters at first. But several things kept me listening to that, and I became hooked on his other podcasts:

- The idea that motivation can be summoned by cultivating the discipline to commit to a thing; motivation is not some external thing that you have to seek out and capture.

- The concept of procrastinating your procrastination — you might not feel like doing something from your routine today (be it exercise or hacking on a project or learning a language), but do it anyway; you can always not do it tomorrow if you feel the same.

- This was pretty hard-hitting for me: “That second that just went by. That counted. And so did that second. And in those precious seconds, you are either building, or you are decaying. You are either gaining ground or you are losing ground. In that second. And in every second.”

The interesting thing about the Valley Forged article for me was that Eric seemed to fall into it — he didn't set out on a path to find something to dedicate 5+ years of his life to, like those game developers in Indie Game The Movie who wanted to make games since childhood. He wanted to make a game to get better at programming, and that evolved into an obsession almost out of happenstance. I think there's a lesson there that throwing yourself into things that seem fun wholeheartedly and with discipline can yield better results than skimming topics at a shallower depth.