Comment by evo | Hacker News Reader

Comment by evo | Hacker News Reader

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I think there's always inherent tradeoffs to specialization vs. generalization, and side projects/side hustles are more of a generalization technique. It feels rather akin to the "exploration vs exploitation" tradeoff in AI; do you search the space for better opportunities, or maximally refine the opportunity you have?

Specialization is great, if the specialty you choose ends up being important or highly in-demand. For example, everyone wants to be the Geoffrey Hinton of the 21st century, a luminary in deep learning. Not too many people want to be the Geoffrey Hinton of 1986, publishing back-propagation into an AI winter and subsequent decades-long disinterest. It's hard to know which one you'll be (or in the above, both!)

Side projects and hustles allow you to broaden your toolbox and see potentially interesting crossovers. "It's like [X] for [Y]!" is a cliche startup pitch at this point, but it's true that a lot of cool ideas arise from applying principles of one field in a widely disparate area.

I don't think that it's particularly wrong to choose one route or the other--I admire the specialists I know, even as I know that's not something I can replicate. I'm too enamored of the possibilities, and cognizant of the brevity of my lifespan, to be able to commit like that.

> I think there's always inherent tradeoffs to specialization vs. generalization, and side projects/side hustles are more of a generalization technique.

That's the theory behind side projects, but it's a false dichotomy.

Side projects are, by definition, something you do on the side. Your primary day job requires attention whether or not you do any side projects. Side projects are additive on top of the work of your day job, but subtractive out of your pool of free time and energy.

Side projects always start with good intentions of broadening horizons, but people generally realize that they only have so many intensely productive hours in a day. Do you allocate your most productive hours to your job? Or to a side project? It's tempting to say "both" but in practice that will spread someone's finite energy too thin across both domains.

Students tend to go wrong when they think that side projects are the key to unlocking their next big job opportunity. When they start to burn out in their dayjob, they think they're just a couple of side projects away from qualifying for an opportunity that will make them happy. The trap is that being burned out at a dayjob and adding the additional work of side projects only worsens the burnout. They get stuck thinking they need to finish the side projects before they change jobs, but they can't complete the side projects because they're too burned out from jobs and a side project. In these cases, I encourage people to drop the side projects and just apply to jobs. It works better than most people expect.

I agree with you 100% that "side projects as an antidote for burning out on your primary job" is a dangerous place to be, and I've been there several times in my career with deleterious effects. I agree with your recommendation to take that as a warning flag and instead change your job, that is the right call in that situation.

On the other hand, I do find a lot of enjoyment in fields that, today, are dominated by "winner takes all" dynamics and extremely low probabilities of (financial) success (e.g. most creative fields). I don't mind diversifying my time between a primary job that, while not burnout-land, is also a bit boring and reliable, and a secondary that, while incredibly unlikely to "strike gold", is rejuvenating of my creative energies. I do have to be careful that it does not drift into the maladaption that you note though.

And sometimes you want to actually write code every once in a while instead of scribing another three-hour quarterly planning meeting during mandatory training week. Being able to work on your own projects at your own pace and make something out of it is incredibly enjoyable, even if it takes some of your productive hours away from work.

I guess what I'm saying is: hobbies are good, too.

It depends on the nature of the side project (vs. side hustle), its relationship to your day job, and your employer's rules (and attitude). In my case I've done a number of tech-related books. My employer knew about (and encouraged) them. And we've had a tacit understanding that I wouldn't be doing these purely on my own time and I'd continue to work on my "day job." It was never a problem and worked out for both of us.

I certainly know people who do similar things around open source projects.

"Your primary day job requires attention whether or not you do any side projects. Side projects are additive on top of the work of your day job, but subtractive out of your pool of free time and energy."

For most people doing the side-hustle thing (and basically all of them doing it successfully), the calculus is "Put in the minimum amount of effort in my day job, get my R&R in the remaining time at work, and spend my mornings/nights/weekends working on the side hustle" vs. "Remain fully engaged mentally for the 8 hours I'm at work, relax when I come home, don't do the side hustle." That's why many employers hate side hustles.

I can't say which one is a better strategy, because it depends on the circumstances. Certainly the bulk of my lifetime income & assets comes from giving my all to my projects at Google, delivering successfully on them, and getting promoted a couple times. But before then I worked at a couple of startups and there was basically zero opportunity for a raise or promotion, because the company wasn't growing and there was no money to be had. And I got the Google job in part because of side projects (non-monetizable, but they showed I knew my CS and could work with a modern tech stack) done after work.

I know it’s all hypothetical, but do you think the startups would have grown if you had focused solely on growing them rather than the side projects? I know that the median case has bigcorp earnings outpacing startups but in my startup experience (main source of my assets) the early engineers who were super plugged in made an outsized impact on our outcomes that turned into a good financial outcome for them.

Maybe the principle is different though (not startup can bigco)... I did a bunch of side projects in school and at bigco before concentrating focus, so in a way we both went broad then had success going deep.

Just thinking out loud, I think we agree.

> do you think the startups would have grown if you had focused solely on growing them rather than the side projects?

Nope. I actually developed two products for the second of the startups, which was the time period I was working on the side projects. The CEO (my boss) and I are still on good terms, and he knew about the side projects while I was working on them.

Startups usually fail because nobody wants what they're building, i.e. the startup should never have been founded in the first place. Certainly this was the case for this one: we were doing a platform for hedge fund algorithmic trading, but hedge funds are usually very resistant to running their code on someone else's platform, both because of lock-in/competitive reasons and because their code & algorithms are their crown jewels and they're very sensitive about running that on other people's infrastructure.

makes sense, thanks for color!

> For most people doing the side-hustle thing (and basically all of them doing it successfully), the calculus is "Put in the minimum amount of effort in my day job, get my R&R in the remaining time at work, and spend my mornings/nights/weekends working on the side hustle"

Yes, this is the real problem.

Side projects for fun and learning is fine. Nothing wrong with exploring new ideas as long as you're having fun.

But somehow side projects have become synonymous with compensating for misaligned careers. I see too many people working all day (or avoiding work all day) then coming home to work all evening and weekend. Then they wonder why they're burned out and not getting promotions at work.

Side projects can be a springboard to career advancement if executed carefully, but for every 1 side project success story I probably see 10 other people with side projects that never do anything other than drain their free time and add more mental work to their TODO list every day.

Yup +1, I agree with you and the OP. If you work for a huge company your skill set may be extremely narrow. Buy having lots of side project will at the very least give you a talking point if you want to change to another company that might not have the exact position you were working at your current company

>> If you work for a huge company your skill set may be extremely narrow.

In my experience working for a huge company makes it very easy to broaden your skills. You can change teams, take on mentorship and recruiting, lead teams, lead initiatives, switch from front- to backend at different times, and learn from a large number of people - all from the "comfort" of the company you are already in.

Well thirty years later we can see that it worked out really well for him. The most rewarding things in life take time. Like building up interest on stocks. Time preferences are strongly associated with lifetime outcomes. All the best opportunities exist in identifying truths that exist outside the realm of social consensus. You can build your specialization in an environment free of competition. Waiting for the social consensus to change takes decades. Once it does you're in a good position to reap the economic benefits that follow.

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