In my own tiny way, I applied this logic when trying to be a contributor to an existing and popular open source project. I found that puzzling out poorly-written bug report tickets, ignored by the extremely busy experts on the project, I could find work to do.

I started by looking at well written tickets (to-the-point descriptions, minimal reproduction examples), but that method got me no work: some expert on the project would have a pull request for that kind of ticket in just a few hours, whereas I would need at least a week to figure out the root cause and another few days to craft a fix and a test.

So I started looking at ignored tickets, i.e., tickets that had been sitting around for weeks or months with no activity. Those often turned out to be very poorly written tickets with either very little information, or a huge wall of text with much business domain-specific info. If those tickets contained repro examples at all, they were often complex and very long, using external libraries I never heard of, and devoid of table schemas and example data. Sometimes I could get the author to provide more information, sometimes the author would not respond. I might have to infer schemas and make up my own data, try different things based on a stack trace, install libraries I would have preferred to not install, etc. I would work on trying to reproduce the problem for a few days, and at least a few times I struck gold. Then I would work on a self-contained, minimal reproduction case, followed by a week of sussing out the root cause. It was pretty time-consuming, but I was able to get a few fixes merged using that method, such that I was no longer a total stranger on the project (which helped me get other things merged into the code base).

Sounds great, but what if the hardest thing is impossible for unknown reasons? I think you need a sort of on-ramp of steadily harder things so that if you fail at one thing, it's not the only thing you've ever done, and you still retain enough credibility for people to support you while you try again or try something similarly hard.

Unfortunately, the safety net necessary to support oneself while they do the hardest thing isn't guaranteed.

I learned this lesson kind of by accident. I've told this story before but I think it's relevant.

When I dropped out of college the first time around in January 2012, I assumed that my career options were extremely limited. I knew I needed a job, so I applied to pretty much every wage-labor job I could find: McDonalds, Lowes, Starbucks, Aldi, Publix, etc. Almost as a joke to myself, I sent exactly one application to a software developer position on Craigslist for a Flash, Foxpro, and Coldfusion developer position.

The only company that called me back was the software job. I interviewed there, got the job, and thus my career as a software engineer was kicked off.

In hindsight I realized something: the less qualified you are for a job, the more likely a company might be to overlook a lack of qualifications. McDonalds and Aldi and Starbucks have lots of qualified people applying for these positions, meaning that they can be very picky with who they hire.

Now compare this to Flash/Coldfusion/Foxpro developers in 2012. I didn't know any of these at the time particularly well...but to my benefit neither did anyone else! As a result, they didn't get a ton of applications meaning their selection pool was tiny, meaning that they basically had to take whomever they could get.

I probably interpret the message incorrectly, because to me "the hardest thing" is usually some class of some famous unsolved problem. The thing is, to be famously unsolved, many of the world's most brilliant people must have already tried and failed to solve it. There's a chance I have an edge they don't, but it's probably not wise to track your career path to the darkest of dead ends purely on the merits of it being particularly dark.

Example: you know what would be harder than anything we're talking about here? Quadrupling the performance of the best compression algorithms. It's hard. In fact, maybe there's some information theory that even says it's mathematically impossible. That makes it really hard, which makes it what all of us should immediately start working on.

The author writes elsewhere that you also have to have an edge, but that's frequently omitted from this "hardest thing" advice.

It's a good philosophy, but I always cringe when I hear it. Only because I once worked with someone who would always proclaim they were going to tackle the hardest thing first. Real ego play, from him at least.

"brb gonna go broker world peace"

naw but this kind of mindset ended up burning me out at times; some of us clearly take general ideas like this in different ways than intended perhaps

but I think the actual "trick" here is about finding unfilled niches rather than necessarily doing "the hardest thing"

This correlates with tackling the monkey first: https://blog.x.company/tackle-the-monkey-first-90fd6223e04d?...

In the current era of urge to make things faster/more, that article felt refreshing. Good things take effort and time to create, and it is not something bad, it's just the way the things become good.

I worked for a camera company that made [still makes] some of the best cameras ever.

Their Quality was astronomical (with, of course, the rare exception).

It was the kind of thing that I was repeatedly told, by my peers in other companies, was impossible.

But my bosses wouldn't accept that. They could be real pains.

We did make top-shelf gear, but you won't really get rich, doing that (unless you're a SpaceX person, I guess).

I think the people that make a lot of money, do that by finding a "sweet spot," in improving the Quality of everyday stuff.

Idk, I often felt the opposite. I naturally tend towards working on hard problems but my feeling is that if I chose instead to focus on an easier "thing" I could execute really well and be overall more successful.

Liked this post a lot, well done! Definitely appreciated that it was a site that actual has a unique design, and isn't just another Medium article...

A book on a similar subject that I don't see mentioned very often but which I quite enjoyed as "Tough Things First" by Ray Zinn [0]. Not the most popular one, but really down to earth and approachable ideas. Kind of like PG's "do things that don't scale," just applied on a broader timescale.

[0] https://toughthingsfirst.com/book/

So, the hardest thing for me would be to leave my job and focus all my time in starting my own business. Leave friends and family behind to put all my effort on it. Is it worth it? No.

“Do the easy/hard thing first,” is the first of artist Tom Sachs’s Paradox Bullets

https://youtu.be/-Evrm03Y5hI?si=CvadZlyzR-PfwFh5

[Bonuses: narrated by Werner Hertzog and starring Ed Ruche]

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People who are drawn to the hardest thing for its own sake can be exploited, like game developers and postdocs.

Do the hardest thing or do the easiest thing cheaply

My hardest thing took about 7 years to build (with a child getting born and slowing things down a bit) but still. Good to hear that I’m not the only one :)

This is dumb. Don't do hard things, do things which have a high ROI.

I could try to swim across the Pacific Ocean, walk across Siberia or consume a family size portion of McDonalds in a single sitting. All those things are hard. All those things have zero to negative ROI.

Doing hard things won't get you anywhere. Most hard things are useless. And a lot of the most valuable things are not hard at all.

I don't know if there's a way to say this without coming off as rude, but if the hardest thing you can come up with is podcast hosting, then maybe you didn't spend too much time thinking about hard things? If it works for you, great, you do you, but I don't think it lines up with the title nor the premise of the article even remotely.

St. John of the Cross in the Ascent of Mount Carmel,

"You should take care always to be inclined

not to the easiest thing, but to the hardest;

not to the tastiest, but to the most insipid;

not to the things that give the greatest pleasure, but to those that give the least;

not to the restful things, but to the painful ones;

not to consolation, but to desolation;

not to more, but to less;

not to the highest and dearest, but to the lowest and most despised;

not to the desire for something, but to having no desires.”