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Comment by willparks

3 days ago

> A common lament among founders, even successful ones, is: "Sometimes I feel like I'm wasting my twenties".

Interesting perspective, I feel like I see this much more attributed to someone working on a meaningless problem for a paycheck at a large company. I guess it speaks to the difficulty in finding purpose in any endeavor in your twenties.

Nice conclusion on what to truly value.

It's basically a tradeoff between wasting your personal life or wasting your professional life. If you get a job that is truly 9-5 (or maybe even a bit less), it leaves a lot of time for forging friendships and relationships and learning hobbies while you're still young, doing sports, seeing the world.

Founders usually feel they're missing out on all or most of these. And some of them probably feel like they don't really have a choice - maybe their specialty/resume is one that's difficult to get hired but skilled enough to make money on their own.

However, plenty of jobs take all your time and still feel meaningless. Many (most? - median personal income in USA is $42,000) don't pay enough for people to really socialize much anyways or do most of the hobbies they might enjoy or travel at all. Generally, having the choice of "HOW should I 'waste' my twenties?" is a fairly privileged one.

  • Well said. To expand on what you wrote, I like to think of there being three components (axes) to activities: fun, value, and meaning.

    Fun is you enjoy doing it. Playing video games and watching TV is fun.

    Valuable is it makes money. Importantly, it's what other people are willing to pay you money for, not what you think is important or even good.

    Meaningful is it's spiritually enriching. These are things you would regret not doing on your deathbed. Spending time with your family or going to church are common examples of things that are meaningful to people (and potentially fun). This one is defined based on one's internal compass and varies significantly from person to person.

    You can come up with activities that are pure fun, value, or meaning. Measuring activities against these three axes has been a valuable mental model for my time management and life design.

    There's jobs that are fun and meaningful, but don't pay much. This is like charity work or passion tax industries such as game dev, music, or art.

    There's also jobs that are fun and valuable, but are meaningless. Working at a trading firm/hedge fund is a common example (though some people may find that it's all three or only one). Another example is being a successful startup founder working on the wrong problem.

    Finally, there are jobs that are valuable and meaningful, but maybe not all that fun. To me, this is what being a startup founder (working on the right problems) or how I imagine a professional athlete is like.

    The grand slam would be having all three, but in my experience these are exceptionally rare. If it's fun and meaningful, everyone wants to do it, and supply and demand pushes the value down. Most of these cases are due to unusual personalities that let one find fun or meaning in activities others don't. This ties into the common startup advice of paying attention to "founder-problem fit" and "what are your unfair advantages".

    • Really enjoyed the way you put this - I’m going to use these axes going forward as I’ve had a hard time putting words to these

    • Very nice framework.

      I think there is yet some other thing which has a bit of both your Meaningful and Value. Stuff that you decide you should do not precisely (or maybe precisely and this comment is just not well enough considered) because it's meaningful to you but because you just feel it should be done.

      Maybe because you just recognize that someone has to do it and you should at least take your turn if not make it your whole life. Maybe because you want to live in a world where it gets done, even if you live in a society that doesn't provide for it to get done. (no one will pay you or anyone else to do it)

      Phrasing these things as meaningful makes it into something someone else can say is simply your choice. If it's important to you, you can do it. And let you shoulder the entire burden for something they absolutely benefit from and should be pitching in their fair share towards in some form or another, if not tax money then time or effort, something.

      It is definitely meaningful for some people, the people that are so moved that they actually give their time & energy, but those are people for whom it's actually a large part of their life & identity. I'm not like that. I am not going to volunteer for whole shifts anywhere. I care about a strangers problems intellectually. I care in the sense that I want it dealt with humanely with dignity as if I had the problem myself. I don't care directly and personally, emotionally, unless they are somehow close to me. But I would happily pitch in my fair share if we all were, because it would be small.

      It's partially value because we all get value from living in the better world thanks to the various thankless tasks some people perform.

      Eh, maybe I'm arguing up the wrong tree and what you expressed already covers this.

      I am thinking something like "This thing should get done not because I derive meaning from it.", but really maybe what you're talking about isn't even trying to deny that. The point would still be that I might choose to commit a certain amount of my life capital towards something, because of a certain amount of value and meaning that I, let's say recognize not derive or get, from it.

      I'm leaving out fun. You can have fun cooking soup for the homeless. I can not imagine having fun cleaning someone who can't clean themselves and can't pay you to do it.

I have this crazy insatiable addiction to food and shelter. My paycheck supports my addiction.

Thought experiment: you have three sets of 10 recent college grads. One set works as enterprise devs in a tier 2 city, one set works at BigTech and another set works for a startup, which group do you think will have the highest median income after 10 years?

I would much rather work for a “meaningless paycheck” (and RSUs in a public company), than bust my ass at a startup for below market wages and “equity” that is illiquid and will statistically be worthless.

But wagies clock out at 5 and live that half of their lives, severance style.

Startups/entrepeneurs often don't even have that duality and live our single life entirely through work. I would identify with "wasting my twenties" in the sense that the life of the entrepeneur isn't really age specific, it would be quite similar to do business at 20 than to do it at 50. The only difference being experience. But there's not much use of my young body, or libido, strength, that is typical of youth experiences.

> "Sometimes I feel like I'm wasting my twenties".

Is near universal to anyone in their twenties regardless of job type/sector. It's the start of most people's adult life, and without the lack of experience that age brings, it's natural to question if you're on the "right path" and/or be swayed by potential other opportunities you've not yet explored.

Hell, even with the experience of age, people still often ask themselves that very same question, and not just for their twenties either.

  • Exactly, I know people who weren't founders, had a typical college experience and then got a "normal" job that look back and feel as though they wasted their twenties because they didn't grind out some start up. Looking back and wondering if you could've/should've done more/differently is a super common experience.