Like just about everyone, I don’t have nearly enough time to do everything I need to do in my life, let alone what I want to do. I need to figure out what to do about that. I have some vague ideas, but nothing fully formed and ready to go. That’s pretty frustrating. Like, self taunting self that you’re losing at life frustrating.

But I do have a goal: I want to move from being a 9-5 guy into being a 24-7 guy. I don’t want to simply work 40+ hours a week so I can afford to keep living and maybe (ha!) retire someday. I want to take that time I spend working and put it into activities that are meaningful to me and happen to generate income. I’d rather spend all my time doing that than spending most of my productive hours working on someone else’s projects and try to cram my own stuff into whatever’s left over when The Man is done with me.

To summarize, I want to achieve a convergence of work, income, fun, and values. I got a good taste of it this month when I worked on my game project and delivered my talk at Notacon. I didn’t make any money doing it, but had I figured out some way of doing so, I would already have the life I want. As I see it, I’m pretty far from having that life right now. And, unless I’m smart about how I go about it, the more I work for The Man, the further from it I will get.

I don’t need to maximize my income potential; I’d rather not compromise doing what I love in order to make the most income I possibly could. I do need to make enough money to live on. I don’t necessarily need all that much to live, and could deal with making less, and working longer to attain it, as long as I truly love what I’m doing. Before getting too far along in this dream, I have to figure out how to make any money doing what I love, try that out, and get it to work.

What are the things a person needs to do to accomplish this? Why don’t they teach you this in college or high school, when it would be super useful?

Looking for advice here. This blog does have a comment feature.

Updated: 2014-Aug-17 — 4:51 am


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  1. What’s worked for me is the simple aspect of not letting go of your principles, no matter what kind of situation you’re put into. If you’re working for the man, gather as much information on how an organization should operate, see how the Man is running it poorly, and put it in the back of your head. When you’re working on your stuff at home, work with the passion of doing something you love doing. Don’t strive, be.
    I literally fell into this whole entrepreneur thing (I hate that word). I didn’t and won’t take classes on how to do this stuff, as it’s all very individual. People that run things by the book are seldom happy with what they’re doing.


  2. It’s actually interesting, your talk at Notacon had me thinking about my goals and dreams and what I was doing to achieve them, and I actually started to have almost exactly the opposite thoughts as you. All my life I worked in the entertainment industry. First in television and sports broadcasting, then video game design and development, and then working at a sports venue. What I noticed was that I was always working to entertain others and never had time to entertain myself. Weather it was working a football game on thanksgiving, 90 hours a week during the deadline rush to get the game out, or going all summer with only 2 days off while working at a racetrack, so many things in my life had been put on hold.
    What I realized the past few days is that I really appreciate my “normal” day job. I do a good job at it, it pays decently (yet could still be a lot better) but unlike every other “cool” job, it doesn’t drain me. Instead of giving all my creativity to somebody else I come home and still have energy to do something creative for myself. Hopefully eventually that creativity quell turn into some extra income for myself, but I have that ability to do that because I have a normal “boring” 9-5 job.


    1. Skraut, I’d almost certainly feel the same way as you if I had that sort of experience. If you’d been working 90 hours/week on something personally meaningful, though, you’d have the sort of life that I am trying to find. When I said I want to be a 24/7 guy, I mean I want to get out of a work life where I’m working 40+ hrs/week for someone else, and gain a life where I’m working as many hours as I can on my own creative projects, doing what I love while having 3. ????, and 4. profit! happen somehow. If I could pour that 40+ hrs/week that I spend making money into making my dream, if my dream generated enough income for me to live on, I’d be pretty happy. Working 90+ hour weeks on someone else’s dream doesn’t sound like what I’m looking for at all.


      1. I don’t think that’s what Skraut is saying. I think the point is: what if you could work for The Man 9-5 and leave the rest of the time for yourself? The disadvantage is losing forty hours per week, but the advantage is that the rest of your time should be basically free of money and survival worries.

        That way you can create anything you damn well please with absolutely no regard for its income potential. That’s kind of cool.

        It’s not the only way, but it’s a reasonable one.

        I guess the question is: do you really need to be “creative” (in that sense) all the time? Or are you just as happy being creative when you’re not at work, which is a little more than half your waking hours anyway? It’s not as simple as it sounds, because being a “24/7 guy” tends to have more economic ups and downs which infringe on your creativity.


  3. High school and college don’t teach much of anything useful. :-) The real trick, it seems to me, is to know what you want. It’s very easy to think you know what you want and to be wrong.

    For myself, I’ve gotten rather lucky in that what I love is writing systems software, and I get paid well to do it. But I had to stumble into this to even find that I liked it — I was dropping out of grad school in 2001 not knowing what I wanted to do with my life.


  4. Not to be “that guy” who recommends a book for every question, but Seth Godin’s Linchpin does a pretty good job at examining why education has been pretty poor at preparing people to do what they want to do (short story is that today’s education is based on a system that was developed for the unskilled labor required for the industrial age). You may not need to read it though as it seems you are already asking yourself the questions that Godin is trying to get people to think about.


    1. Yeah, I was mainly asking that question rhetorically. My take on it is that educational institutions exist primarily to institutionalize, not educate. Like you point out, their purpose is to create a workforce for the economy. They’re not even very good at that.


      1. Would you say that Wooster does the institutionalize-not-educate thing? Because it strikes me as the kind of school where you can practice being your own badass self, most of the time.


        1. I do think Wooster was a good school for me, but speaking personally, I didn’t get a lot of practical “how to apply this knowledge to living your life” or career direction from going there. It could be that I didn’t get as much out of it as was available to me — I certainly did not find a mentor while I was there, and utilized my academic advisors and the career center very little. My undergrad years were mostly about finding myself and de-programming myself in various ways, and learning to think critically about the world I live in.


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