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 you 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!
 
I've thought about this thread alot and my personal goals as well. I was thinking of a nice way to say this ...... but im just going to sound like a dick anyways.

Most of your threads on here looking for advice always come off as "looking for the easy way out". There isn't an easy way in life unless you are stupid rich.
And i hate to say it but you from your online presence dont seem like the super motivated type of person thats willing to put the business first to make it happen.

All my jobs I've tried to surround myself with people much smarter than me and are willing to give knowledge. They all say it is a struggle from day one trying to run your own business. Best advise i got was get 3 years worth of living expense, 2 of that is to survive on as your business grows, one is to use to start the business. you got to get lucky to make a successful small business work. None of these guys took income from the business starting out knowing it needed to be reinvested.
 
As a dude who has launched his own partnerships, has an equity portfolio, started side hustles, worked 100hrs/wk, etc etc…I’ll just say there are pros and cons to everything, and regardless of how attractive something looks, someone is tired of its shit. There was a time I enjoyed the grind…but now I enjoy a long day being 830-515 and a 4min ride home for a 2hr lunch with the animals/kids/gf isn’t uncommon. Regardless of your title, you always have to answer to someone. These days, it’s a lot more about security and accepting 8hrs of my day is going to suck and being able to unwind the rest of the time, than 16-20hrs is going to suck and stressing about the next day and still not being able to do what I want.
 
benXJ said:
i still want to hear what exactly you'd be doing fer yerself
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I have no idea. I have all these ideas and things I come up with but its usually just all talk. I was just wondering what all comes with having the freedom of working for yourself. I do love the stability of what I currently do. Sometimes I just wonder if there is more out there. Just asking around to people I know who work for themselves to what all the ins and outs are.
 
Loganwayne said:
I've thought about this thread alot and my personal goals as well. I was thinking of a nice way to say this ...... but im just going to sound like a dick anyways.

Most of your threads on here looking for advice always come off as "looking for the easy way out". There isn't an easy way in life unless you are stupid rich.
And i hate to say it but you from your online presence dont seem like the super motivated type of person thats willing to put the business first to make it happen.

All my jobs I've tried to surround myself with people much smarter than me and are willing to give knowledge. They all say it is a struggle from day one trying to run your own business. Best advise i got was get 3 years worth of living expense, 2 of that is to survive on as your business grows, one is to use to start the business. you got to get lucky to make a successful small business work. None of these guys took income from the business starting out knowing it needed to be reinvested.
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you are exactly right. Seriously. Mainly because I always try to have the best of both worlds (rather its realistic or not) But also, I like to learn. I like to learn about peoples experiences with different things. If I had to choose a passion that I would enjoy doing, it would be designing knives. Not making them, but designing them. Choosing the materials and steels, colors, and aesthetics. Sometimes I get excited about the idea of designing my own knives and Ill spend a couple hours a week, drawing some ideas out, but then I get the feeling of this only being a pipe dream and I just need to man up and give my 40 hours a week to the man and take home a paycheck to provide for my family, possibly knowing the whole knife thing wouldn't work out, when I have a nice steady, comfy job that might not bring the joy I am looking for, but puts food on the table and clothes on our backs and pays all of our bills on time.

I wouldn't say I try to find the easy way out, but I know that being away from my family is not negotiable. I want to be home every night and I want to kiss my daughter good night every night, and I know that's my hang up. So I just try to have my cake and eat it too I guess. I've also been burned a couple times with opportunities that "Could" have been great and they always fold, so I have a bit of a sour taste in my mouth from it. I know that is part of it, but I just always like to reach out and see what people are doing. I know I could sell some pics of my piggies and make a pretty penny :)

I think alot of it is, I am just at an age where I am very confused about what I want in life. I started working because I had to (and still do) but 15 years have gone by and while I have everything that I need, I guess I just want more and I just don't know what that "more" is
 
benXJ said:
incredible/successful biz and payroll isn't done with ADP or the like? or he waits till the last second for payroll duties every week? no secretary?

he still writes checks to them?
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Payroll service does the financial side, taxes insurance etc. Someone has to enter hours and or approve time. As an owner you want to trust a secretary to enter payroll and authorize payment without the owners input? Might as well write that person a personal check before they steal the money. Company I work for 50 years in business 2nd generation, owner still authorizes payments so he doesn't get robbed by his own employees. Not that many currently employed would but it has happened in the past.
 
When you are busy you won't have time. When you are slow you won't have money. Then maybe in 20 years you will have both after your business has matured.:beer:It can be very fun though if you have chosen the career you enjoy!
 
benXJ said:
just start buying low and selling high.....like this guy. then hope that the real estate that you own triples in value over 8 years

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An interview with him recently somebody asked if it was luck at all in how he got there. He said no. Bs I call, a lot of very successful people still had some luck help them along the way
 
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Cherokeekid88 said:
I have no idea. I have all these ideas and things I come up with but its usually just all talk. I was just wondering what all comes with having the freedom of working for yourself. I do love the stability of what I currently do. Sometimes I just wonder if there is more out there. Just asking around to people I know who work for themselves to what all the ins and outs are.
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Freedom of working for yourself is also freedom to fail. It really isn't freedom. It isn't slavery either. It is responsibility for everything. Everything including all the things you have thought about and twice as many tasks you haven't.

Work space, equipment, supplies, cleaning, paperwork, maintenance, errands, advertising, accounting, billing, tax liability( both sales and labor), taxes on the personal property acquired to do business , self employment tax rates, insurance, utilities, vendors, the replacement cost of anything used, and probably more I forgot all cost you money before you ever profit a dime. All the above apply to any line of work. Not just manufacturing or services considered blue collar. Even a desk, computer, and home office require most of the items listed.
 
WARRIORWELDING said:
Freedom of working for yourself is also freedom to fail. It really isn't freedom. It isn't slavery either. It is responsibility for everything. Everything including all the things you have thought about and twice as many tasks you haven't.

Work space, equipment, supplies, cleaning, paperwork, maintenance, errands, advertising, accounting, billing, tax liability( both sales and labor), taxes on the personal property acquired to do business , self employment tax rates, insurance, utilities, vendors, the replacement cost of anything used, and probably more I forgot all cost you money before you ever profit a dime. All the above apply to any line of work. Not just manufacturing or services considered blue collar. Even a desk, computer, and home office require most of the items listed.
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$247,618 per month.
That next dollar is mine. Well unlesss I have any COGS that month in which case not yet. Overhead is a bitch.
 
Another thing.... think about who your customers/clients will be, and how they view and manage money (and therefore, pay you). I had several different types of clients over the years...

Individuals -- some, even a $50 charge would shock them, and probably affected how many groceries they could buy that week (I avoided working for individuals, unless they worked for one of my business clients, and I liked them). More demanding than anybody, especially bad for blaming for something else broken that you didn't even touch (fix a virus, and they complain that their printer died the next week kind of stuff -- same thing will happen with auto repair, home improvement, etc).

Small businesses (1-5 employees, sole prop.) -- same deal, they'd take any cost or invoice personally. I did a lot of work for small businesses, but invoicing and getting paid easily was the worst part.

Big corporations -- 90-120 days to pay. Always tried to short you on something. If they had internal IT guys, it seemed they worked against you to protect their "turf"

Family-owned and closely-held corporations, 20-50 employees -- the best of all my clients, and I worked to make them the backbone of my business. Most of them would, as soon as I walked in with an invoice (whether 100 bucks or 15 thousand), write a check right there on the spot. Rarely if ever questioned an invoice. Never wrote me a bad check.
 
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And wait, there's more...

Don't forget, you have to figure 2 paychecks for yourself -- one, a living wage. How much is your time worth a year, 60k?

Second....to compensate you for what you have to invest in the business. If you have 300k in equipment, tools, truck, whatever, that's money you don't have invested in a passive income source that'll pay you at least 10%. So, you need at least 30k annually on that 300k invested to cover that. The more "at risk" it is, the better return you need. 15%? 20%?
 
Cherokeekid88 said:
For those of you who work for yourself, how did you figure out what you wanted to do and how has it been?
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For me , it was what I was already doing for someone else. I didn't set out to be self employed, I took time off to remodel my house, ended up getting my gc and picking up enough work after to keep busy. I have no employees and that's the way I want it. I dont want to be responsible for somebody else's livelihood or the drama that come with hiring folks in the construction industry (I got enough buddys that i hear that from). I dont advertise, so my phone doesn't ring off the hook and most of the folks I work for I actually know fairly well. That's probably not the best business model for making all the moneys, but im not overwhelmed with phone calls and im not working 100 hrs a week trying to get multiple jobs finished. If I need to take off to go do something, I do feel like I have the ability to do that. Got my dad to help me pour footers for a house yesterday and he needed me to haul a new project home today for him so that's what we did. My wife teaches so she gets the summers off....when @jcramsey lived in Charleston we rented his neighbors house for a month and stayed down there....now that required a little more planning but I'll trade not making money for a month for that any day. So far, I think it's working out after 10+ years.




And today's "work" just for some motivation

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@Cherokeekid88 buddy, I wanna help ya. I and others have offered you advice over the years. Hopefully you'll accept this piece.
Buy this book and help determine what career will make you happy and will motivate you
Then read up on the Ramsey financial plan(s) for that business.
There's some folks who do quite well in varying industries here that can attest.
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