Going into working for yourself

I have never had a W-2 job. Started in 1983 doing computer stuff while in college. Mostly retired in 2015. Finally cut my last client off in 2020. Which happened to be my first client 37 years prior.

Most all of that time, I worked from home. I heard more than once "Cool, you're always at home." My answer was always "No, I'm always at work." You can't get away from it. Sit at the desk for five minutes to do something "quick", and several hours later you are still there working on stuff that has to get done. It wasn't so bad the first 15 years or so. People were still so used to doing everything on paper, they could (mostly) easily go back to paper, until an issue was resolved. So, I was able to take a lot of time off. A lot of 1-3 week trips, mostly camping and hiking. A few trips got cut short, but that was rare. Then, the last 15 years I worked, everybody became so dependent on (or addicted to) their computers that they couldn't stand to be down an hour. Much more demanding, and even weekend trips became difficult.

Anyway, the whole point of this is don't pick something that you can't get away from. I surely would not go into computer/network/tech stuff, or a similar type work, again. Think of a service type industry where you can schedule out (and around your time off), and are able to say "no" as needed. Something that "emergencies" don't come up. Not seasonal. Low overhead (no office, shop space, etc). Off the top of my head, I would think along the lines of things like pressure washing, carpet cleaning, fleet wash, etc.

And don't get me started on employees (or 'partners'). I swore off ever having another employee.
 
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My side-hustle/dream job is writing.

Unfortunately, I'm pretty good at what I do so they pay me pretty well to keep doing it. And then there's all the perks, like company matching 401k, better insurance, etc.

And with royalties being around $1.25/book, I'd have to sell a lot of books to overcome all the financial perks of my day job.

Dangit.
 
My .02 worth for what its worth.Set certain hours/days for yourself and stick to it if at all possible.That's something I've never been able to do.I'm always looking.thinking,talking about it.Yeah it is nice to be able to take your kids to school,pick them up,or keep them home when they are sick. Yeah you can come/go as you want for as long as you want but the longer you stay away the less youre gonna make.If I take a week off it takes two to get things rollin again.IS your wife gonna be alright w/o not you having a set weekly income?? Because there will be weeks when you dont bring home much and other weeks you'll make a fist full and that can cause marital problems.A friend of mine got divorced because his wife was use to him having X amount coming in each week and when he went out on his own that stopped.Not all spouses can handle that.Im lucky Tonya's dad was a contracter and didnt make the same every week so she was use to it.This will be my 20th year in July of being on my own and at first I was hungry for it.was hungry for it for a long time. Now in my 50's Im not willing to do the same stuff I was willing to do in my 30's,the hunger has passed.If you do it long enuf you'll be the same way.I kinda got pushed out and my side hussle was all I had at the time.I went from buying beadlocks and boggers to paying a mortage and other monthly bills.
 
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kaiser715 said:
And don't get me started on employees (or 'partners'). I swore off ever having another employee.
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I know partners can work out but every partnership Ive been around didnt.One did all the work and got 1/2 the money.Thats why I've never tried a partner.
 
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Cherokeekid88 said:
I figured as much. I just dream of having the freedom to pick my daughter up from school every day and to be able to go with her to school functions during normal working hours, not having to fight over PTO days with other people when I want to take a trip or just some time away. My wife had a side gig for about a year where she could work basically any time she wanted filing reports and made some good money doing it, but we knew it was going to be short lived. Sometimes I just feel like there is more to life than working for the man.
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Late to the game here but - Then what you need is a job w/ remote work options that doesn't care about hours.

Up until 2 weeks ago there were tons of great jobs like this in the government!
 
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