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Working for someone vs. doing your own thing

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Re: Working for someone vs. doing your own thing

#2
I like Austin Kleon's insights here [1]:

"A day job gives you money, a connection to the world, and a routine. Freedom from financial stress also means freedom in your art. As photographer Bill Cunningham says, 'If you don’t take money, they cant tell you what to do.' Because the real truth is, once you start making money doing what you love, it BECOMES A JOB. And with it comes all the hassle of a job."

It's why I've personally decided to work for someone else full time and then use any time I can get outside my day job to do the things I really enjoy (which are very profitable). The full time job enables me to be more "creatively reckless" in my side projects, which in turn allows me to learn a lot and stretch creative muscles I might not otherwise get "working for the man."

1. From: https://tumblr.austinkleon.com/post/69005574484

Re: Working for someone vs. doing your own thing

#3
Not to be dismissive, but this post feels a bit like rambling without a clear thesis or main argument. It's also rife with dubious claims:

> I’ve been working remotely for four years now, and I know that working alone can make you lonely..

I also work full-time remotely. I built a community around myself, made new friends and regularly hang out with people I met at coffee shops, at startup meetups, old classmates, ex-coworkers (that may also be fully remote), etc. I hear it a lot, but this argument honestly falls flat on its face as long as you're not a weird hermit that only works from your house. In fact, that main reason I wanted to work remotely is because I get to meet people (particularly women, as I'm getting to an age where marriage is starting to become a priority) that I'm more interested in than in the myopic circles that are commonplace at large tech companies.

> I like the idea that you can earn money while you sleep, but are those businesses fun?

Yes. Because it gives you the freedom to do whatever you want. And freedom is fun. I mean, passive income is basically free money -- I'm not sure I'm getting what author is saying here.

> I imagine working on your own thing full time and on the side are definitely not the same; it’s scary, to be frank. If my side-project became my full-time work, might my passion for my project dwindle and become yet another job? How would it differ from my current job?

I don't see how working for your own business could ever become "just another job" -- you're acutely invested in the venture, your strategic decisions guide it's success (or failure). Working for a corporation is the definition of "autopilot" for most above-average employees (engineers or otherwise). This could not be more different when doing your own thing.

Re: Working for someone vs. doing your own thing

#4
There's a pretty high correlation between parental wealth and success as a startup founder. I assume it's because of the safety net.

My friends who have been successful (and who had blue-collar upbringings like me, and all in mid-40's now) all worked full time jobs until their side projects were self-sustaining. None of them hit unicorn status, but I think all of them have lived healthy, fruitful lives.

Also note by "sustainable" I mean they had contracts worth substantially more than their salaried job. Because to transition to that completely, you've got to set aside time and money for so many things: insurance, legal, hardware, whatever corp infra, recruiting, etc, as well as offset the risk. So I'd not jump ship too soon, until you have a real plan on how to get your company from A to B. Especially these days when tech salaries are so high, it'd be a mistake to opt out of it too soon.

Re: Working for someone vs. doing your own thing

#5
Probably the biggest hurdle is dealing with healthcare on your own, it's just prohibitively expensive to deal with alone in the US. Multiple incomes is where it's at, at least until one of the projects takes off to cover cost of living and healthcare nonsense.

Re: Working for someone vs. doing your own thing

#6
post #3

Not to be dismissive, but this post feels a bit like rambling without a clear thesis or main argument. It's also rife with dubious claims: > I’ve been working remotely for four years now, and I know that working alone can make you lonely.. I also work full-time remotely. I built a community around myself, made new friends and regularly hang out with people I met at coffee shops, at startup meetups, old classmates, ex…

I think the rambling was basically the point. He wasn't sure. I found it kind of refreshing.

Re: Working for someone vs. doing your own thing

#7
post #2

I like Austin Kleon's insights here [1]: "A day job gives you money, a connection to the world, and a routine. Freedom from financial stress also means freedom in your art. As photographer Bill Cunningham says, 'If you don’t take money, they cant tell you what to do.' Because the real truth is, once you start making money doing what you love, it BECOMES A JOB. And with it comes all the hassle of a job." It's why I've…

Yes, however if you can figure out a project that pays your salary and is low maintenance (very hard) you can have even more time for your art :)

Re: Working for someone vs. doing your own thing

#8
post #3

Not to be dismissive, but this post feels a bit like rambling without a clear thesis or main argument. It's also rife with dubious claims: > I’ve been working remotely for four years now, and I know that working alone can make you lonely.. I also work full-time remotely. I built a community around myself, made new friends and regularly hang out with people I met at coffee shops, at startup meetups, old classmates, ex…

Paraphrasing, but he said early on that he wasn't trying to convince the reader of anything and that it was just a brain dump of his thoughts.

Re: Working for someone vs. doing your own thing

#9
post #3

Not to be dismissive, but this post feels a bit like rambling without a clear thesis or main argument. It's also rife with dubious claims: > I’ve been working remotely for four years now, and I know that working alone can make you lonely.. I also work full-time remotely. I built a community around myself, made new friends and regularly hang out with people I met at coffee shops, at startup meetups, old classmates, ex…

>Not to be dismissive, but this post feels a bit like rambling without a clear thesis or main argument.

The post opens with:

>This is more of a brain dump or an internal monologue. I don’t intend to prove any point or convince you to start your own thing. Neither do I want to reassure you that working for someone else is the best option for most people. My goal here is simply to get my thoughts out so I can think clearly again and rationalize this thing that’s been nagging me.

Re: Working for someone vs. doing your own thing

#10
post #4

There's a pretty high correlation between parental wealth and success as a startup founder. I assume it's because of the safety net. My friends who have been successful (and who had blue-collar upbringings like me, and all in mid-40's now) all worked full time jobs until their side projects were self-sustaining. None of them hit unicorn status, but I think all of them have lived healthy, fruitful lives. Also note by…

Given the research on adverse childhood experiences, there's likely a subtler advantage too, for founders who were raised in more stable and secure environments. Growing up under greater pressure (violence, abuse, trauma) leaves you less resilient, more risk averse, more at risk. I'm not saying wealthy families don't have this, or that poor families can't be stable and secure. But on average it probably makes a difference. Call it an emotional safety net.
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