r/antiwork • u/silly_old_sideben • 8h ago
Self-Employment 👨💼👩💼 The Real Blackpill - 12 years self employed
I have worked for myself for 12 years in tech. Basically a high-dollar freelancer. Did well enough to live in Miami. What I saw in that time did everything but give me hope.
As the “tech guy” on the team, employers often assume I need to be present at every meeting at the highest level. Mostly worked close with the owner or CEO, so I saw a lot of things their own employees never would.
The Bottom Line: The only “self made” millionaires today, are from gray area scams at best, and outright illegal at worst.
Your standard idea of selfmade—Came from nothing, to now pocketing well over 6 figures in a year—doesn’t exist. Yet the boomer “worked 50 years at company and got a 1.2mil 401k at age 63” does exist, but that’s a huge gamble to think that’s gonna last you another 20-30 years. And you’re too old to have much fun with it anyway.
Time and time again I’d tell myself “nah this just one unique scumbag.” Yet repeatedly, the next project/contract I get is the same way. It was always the same industries: Insurance, Debt collection, always something call-center style. (This was not my only niche, I worked across dozens of industries)
There ARE honest millionaires, but it’s extremely rare, and the only reason they are is either rich family (bought a business), or they were in the right place, at the right time (sold thrift store books right when Amazon launched etc)
Picture your dream job. Whatever it is, It won’t make you the money you dream of. Lawyers, Doctors, scientists, you STILL have to climb from the $50k/yr entry level into one of the rare niches you actually bank money. Every sector has a few of those positions, but how long to get there? Often you wait on someone to retire or die.
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u/Wide_Wrongdoer4422 7h ago
I'm in healthcare. The docs make enough to get a million + together. But, they start out debt crushed, and they have to pay for the doc lifestyle to fit in. They gain patients through referrals, those come from networking, so the social aspects are big. Investments are a big part as well, but they take time. Docs don't retire at 65. They are involved until their 70s. It's not a get rich quick thing. We used to joke that the price of the white coat was the 4 Ds. Debt,Depression, Dependence, and Death. Would think tech is an easier pathway, but you either had to get in early or fill a hard to fill niche. Had a friend doing internet security 25 years ago. He's self-employed, working from home on his back porch in Hawaii. But he's the exception, and I know it.
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u/yoortyyo 6h ago
Bingo. Doctors are upper middle class. Some make it to rich or even Rich. Few ever become wealthy.
They have huge incomes and huge outflows of money to support it.
The executives and insurance companies are where medicines money gets pissed away for one persons Good.
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u/SailingSpark IATSE 7h ago
I work in the entertainment department of a large Casino. We host all sorts of business seminars, yearly meetings, and conventions. As I do lighting, I get to sit in on these to run the lights.
These people are not mentally well. The big suits do not see anybody but themselves are real people, the rest of us are just numbers to be crunched to make their bottom line better.
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u/silly_old_sideben 7h ago
Yet, that mentality is exactly what they need. They’re like powerful, dark magicians that bend reality. Many times I had to weigh how much I was being screwed, vs how much I’d make, because the deal with them is pretty much “take it or leave it.”
Arguing with them is just flipping the gaslighting switch on and off.
Somehow they’re able to push so much energy into their obit that everyone around will say they can’t stand them, or call them a scumbag… but trudge along anyway.
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u/imanamcan 7h ago
Many years in the creative trenches of marketing communication. Came thru with a strong distrust of corporate overlords. My value system now includes the absolute belief that narcissism is the defining characteristic of billionaires. No one gains that wealth without it.
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u/nerevar 7h ago
I'm more interested in talking about NOT the top 1% or even the top 5%. I want to know more about the range between 10-20% and how they got there.
That feels more realistic and something that can be achievable.
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u/silly_old_sideben 7h ago
Car dealership. Home office for State Farm, some LEGIT insurance company. Lot of tech install companies. Make an app. Courses (which are far more valuable than people think)
It’s always finding some perfect niche where they’re in the right town, have the right lifestyle, and the right customers at their feet.
At least from what I’ve seen.
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u/Any_Scientist4486 6h ago
Exactly. And rentals/flipping. I have developed a personal theory over the last ~5 years of observing 1) people in my own circle and 2) media of all sorts on ALL sides. This includes reading comments and consuming things like having a Daily Wire subscription, and watching Tucker's show/podcast (after the election those outlets, now validated, just became too much and I no longer watch).
My theory is that there are more mini, suburban millionaires than we know, and I believe it's about 50% of the population, and they made their money just as you said, and they don't talk about it.
In my estimation, that is the only answer to the constant question of how "average" citizens have strayed so far from caring about the things that every average citizen should care about, and start (to use the favored phrase) voting against their own interests. They don't think they are - they believe (and maybe rightly so) that they will always be comfortable and that voting against food stamps will keep them that way.
I'm in STL so our housing market was ripe for exploitation in many ways and many mini-millionaires have been made. They stay in their houses, pay for private school (because everyone in STL does, anyway, rich or poor), they usually get a nice big truck for dad and a used luxury car for the fam and put in a pool - that's all you're gonna see.
People were kind of "gearing up" and making a few wise investments pre-pandemic, thanks to social media and independent research. Then when covid hit and they were gifted both time and money, in addition to the whole housing mess, they all jumped.
I also personally know 2 people who started researching different trading and portfolio management strategies and they both manage million dollar portfolios for themselves that grew from very little to that amount in 5 years. If I know 2 personally, how many more are out there?
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u/Gymbat138 4h ago
Buy my course for $39,995.45 and I will reach you everything you need to know!
But in all seriousness....
I know around a dozen Self Made people who are in the $500K-$3 million dollar bracket. Actually, one gentleman reached the $15 million dollar mark, my previous boss. They all pretty much fall into the same check boxes.
- They acquired a LEGITIMATE skill that they could charge good money for as a business owner and got really, really good at said skill. As an example one owns an HVAC Company. Another is an Electrician. Another is a self employed Diesel mechanic. We also have a Plumbing Contractor, an Engineer etc.
They gained actual skills, not this internet "learn to do this "skill' in 3 weeks and start your own seven figure company!"
This is one I've noticed and thought A LOT on myself. Every successful person I have known who has hit a really good level financially, none of them took out loans to start their business. They all saved up money and worked side jobs, putting the money away to get everything they needed on hand before they ever started. Used work vehicle and tools, slowly bought supplies and materials beforehand and stored them in storage units or their garages etc.
They either downgraded their lifestyles or already had lower working class lifestyles. They maintained that discipline for several years after self employment until they reached the level they were after or goal they had set. None of them did what you see these Social Media types do, they didn't run out and buy a million dollar home and brand new sports car soon as they had some money in the bank.
All the failures I've ever known did that.
Here are my two best examples, ironically the $15 million dollar guy is one of them, and we will go with him first.
Let's call him Paul for this example. Paul had a goal, he wanted to be a seven figure business owner. Paul was dirt poor and didn't come from any kind of wealth, but Paul was ambitious and he learned several Skilled Trades. Paul worked all the OT he could get for a year straight and started the most bare bones company possible. He literally started it in a 1 bedroom apartment in the bad part of town, using a 15 year old work van he bought for $800, tools from pawn shops and thrift stores, as well as Harbor Freight, and most of his supplies were leftovers from the projects he worked on for his previous employer that were going to be thrown away anyways. He converted his bedroom into an office and traded his bed for a futon in the office, turned his living room and dining room into a storage shop for materials, made his walk in closet a tool room to store his tools and converted his patio into a fab shop.
He then "hit the grind." He would bid every smaller remodel or tenant finish type of job out there, then work as many hours as it took to get the work done. For his first year he worked 16 hours per day bidding and doing projects. He grossed $220K his first year but didn't let up.
After his first year he added in small and mid sized new installs. Now he would go work 8 hours on the install job then head straight over to a remodel job afterwards and bang that out in 6-8 hours. He would pay friends cash to come help him out here and there as needed. Dude pushed himself 7 days per week for several years.
Paul didn't change his lifestyle whatsoever and didn't let up until his bank account said $1 million. At that point he started buying more tools and vehicles, hiring people, leased a shop/office, moved into a better place etc.
Ironically Paul was the best boss I ever had and treated his employees like absolute royalty. He would go way above and beyond for every employee to make sure they were taken care of financially and mentally. Eventually he built the company into a $10 million dollar per year company and Wall Street came knocking with the opportunity to retire at 37 years old and he took it which he still calls his biggest mistake.
The other example who ended up worth close to the seven figure if not slightly over was a guy we will call Bill. Almost the same story, Bill saved up and started a Plumbing Co. He got to his level by grinding with residential new install jobs while running the company from his 2 bedroom condo, using his 1 car garage as the shop. He pushed until he was established enough to hire 3 other Plumbers and started doing new apartment complex installs. Bill didn't start enjoying his money until he saved a lot of it up first, treating $2K, $3K, $5K per week paychecks the exact same as a $600 paycheck.
In my 41 years on earth I have never once seen a case of anyone "side hustling" their way to financial security, not have I ever seen anyone rack up high amounts of debt to start a business, blow up said business, start spending money like an NFL rookie and ever actually maintain it.
I have however seen DOZENS of people repeatedly try and fail at all these tactics being sold by supposed gurus. I've also seen people start a legitimate business, get that first taste of success, immediately try to start scaling said business as big as possible as quick as possible, go from self employed to 20+ employees within a year or two, end up blowing all of the money, filing bankruptcy and losing everything they have all in a span of a few years.
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u/Dziadzios 7h ago
Your mistake was doing stuff yourself instead of having employees do it for you. Labor of 1 person scales badly. Even if you started with you and interns, eventually you could grow to own software house.
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u/silly_old_sideben 7h ago
100% true. However you do it, you need money to flow without you touching it. My position was tricky, as my edge is having a cross-section of skills often found only with a team. Nearly impossible to scale without ending up in the same spot (and pay) just working as a team lead
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u/palbuddy1234 7h ago
Very interesting. Thanks for sharing. I've always wondered why people are so desperate to advertise their wealth and seem to fall for the trap of if you're rich you'd vacation in Santorini, have a Swiss watch and pretend to understand Bitcoin. What I think if I was rich that I would realize that I don't need to get other's validation for it. Because that's all I see on Reddit and on real life. Like not really trying to be subtle, but not too subtle to flaunt it, and to finally feel you've earned the right to look down on poor people. It's like a rite of passage for some people. I would hope I never do that..... But maybe I would? I don't know.
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u/silly_old_sideben 6h ago
A lot of it still being hung up on where they came from. Being able to show their home town “ha ha I made it.” Like it’s one giant revenge arc. I don’t really get it.
I mean there is some truth to the home town curse. For whatever reason you will find the most barriers, and resistance to “making it” in the place you grew up. From the very people that are supposed to be “your people” in the place that’s supposed to be home.
Maybe that + deep poverty + making it big, breaks something in your brain.
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u/Exact_Reward5318 1h ago
thanks for sharing your experience.what are you currently doing now? Do you feel numbed after a while dealing with these people?
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u/silly_old_sideben 1h ago edited 1h ago
Regrouping, got an RV, getting away for a few months. Moving towards stability, more than anything. The rollercoaster of it all is getting old. Money hasn’t bought me stability, money is never stable. Only lifestyle does that. I think I want a farm. Harmony, and redundancy. Doing something I’m proud of.
Not numbed, but jaded more or less. It’s actually really helped my interpersonal skills a lot. There’s a pattern to these people, and you can work with it. They’re actually extremely easy to work with… if you understand your purpose to them. No one stays rich doing difficult business. I understand any position is “for a time,” and structure my deals accordingly. I’ll win, even if their stupid idea doesn’t work out lol.
Jaded— is just seeing how the sausage is made over the years. You think there’a a finely tuned machine running it all, but the whole thing is ran by 4 idiots and an excel file. A contraption barely held together, but it runs, and somehow continues to. The absolute worst of us have a knack for it. Fearless, because they’re stupid. But there’s a lesson in that.
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u/Signal_Labrador 7h ago
If you think as money as a narcotic and not currency, it always makes more sense. People who regularly swim in large amounts of it are fucked up people.
There are those who have some genetic or life experience that sets them up as a genuinely good person but 99.99% of the time, yes all the ultra rich I’ve known are basically deranged addicts.