The Uncomfortable Math of Working for Yourself | Hacker News Reader

The Uncomfortable Math of Working for Yourself

thomasunise.com

63 pointseeko_systems14 comments

I am author Unise's age, and also ran my own construction startup for about fifteen years. Covid, bitcoin, and spite helped me fire all but one of my clients.

In hindsight, I do wish my own venture had always remained "side work" — as it was during my IBEW apprenticeship. As a full-time endeavor, this article absolutely speaks Truth ["that manager is YOU — and they're a terrible boss"].

Entrepreneurship isn't for most people, and although I've made most of dollars on 1099... I wouldn't choose so again. I've taken several years "re-grouping" as I try to determine what next... and fortunately still have one client that pays my bills (and enough savings from decade-old investments) and am not too worried financially.

I haven't had health insurance since leaving the union (a decade ago), and am definitely not getting any younger. The things I have done to keep an ungrateful client happy... aren't worth discussing (but I have learned so much).

Hopeful that when this administration ends our economy can pick back up and I can find a decent master/employer. I will be more grateful than most.

Good article, Mr. Unise.

Check healthcare.gov for health insurance.

I've taken a few days to think about this common response, to me (as a no-dependants forty-something with no need to meet exhorbitant US healthcare fees) — there's just no net benefit (v. e.g. paying cash to amenable providers).

Also, I no longer use email so... no effort there.

The author mentioned they’ve been self-employed for 15 years, then proceeds to make a bunch of claims about traditional employment, like being “your professional development being structurally supported,” but it’s important to remember the variance in normal employment, too.

When you’re valuable in a certain position at a company, trying to grow beyond it is like swimming upstream in a raging current. The pigeonholing that happens when you work for a big company is not to be underestimated.

I was about to say something similar. It may be true that the ideal image of the entrepreneur is the exception rather than the typical for the self-employed, but I would say the same for the image the author paints of the career employee. For every self-actualized employee with an enriching network, meaningful work, and supportive surroundings there are many more who are just trying to make ends meet in a meaningless, toxic, soul-sucking environment. The grass is very much greener on the other side...

As my grandfather would say “being self employed is great - you get to work whichever 80 hours a week you want.”

i was self employed for most of my life, and that freedom was always the primary reason. to be able to simply not work when i didn't feel like it, without having to ask for permission, to be able to take time off whenever the family needed it, travel whenever i want, work where i want, etc. these are all things i would not want to miss. you get a lot of that from remote work too, which is why it is so appealing.

but i combined that with a low budget lifestyle. i don't need to work 80 hours. depending on the rate, 10 or 20 billable hours are enough. with family. it's a lifestyle. and you choose how to live it.

> freedom without financial margin is just anxiety with flexible hours.

What a great way of putting it. Especially with survivorship bias tending to highlight the cases that make it over that margin hurdle

> The people who write the books, give the TED talks, and post the LinkedIn manifestos about “betting on yourself” are, by definition, the ones for whom the bet paid off.

> You don’t hear much from the ones who went back to traditional employment after three years of grinding, a depleted savings account, and a marriage that got stress-tested past its limits.

Check, check and nearly check. It was a choice between having a business and having a marriage. Easy choice in hindsight.

You can break up, or you can have a thousand fights. Why would you have a thousand fights? Well, so you can make peace. Having my own business, incidentally with my spouse, was the perfect conduit for those thousand fights. Holy hell in a handbasket. But: I've gotten to know them in a way I don't think I'd ever have reached without the business. I wouldn't change a thing. Except maybe getting a clue at the three year mark that this wasn't going to work instead of grimly hanging on to a dying dream for seven years.

Started a business with my wife as well. It grew successfully and we still got divorced and now we still work together. Thankfully we managed it beautifully but it was definitely the hardest thing I've ever done emotionally. Worth it in the end, we are both much happier and the business continues to grow!

I am 54 . I have been on my own for the last 12 years. I have learned one hard lesson. Surviving IS SUCCEEDING. Yes yes. The problem for me is i have ADHD + i maybe on the spectrum ( i never got diagnosed)+ dylexia and i can't write for shit. come to think about it im not that smart either. IDK. I have a one man shop online business. I only really have 1 skill . I only know how to sell. I grew up in NYC selling fake rolex watches to german tourist back in the day. I mostly worked in luxury retail on madison ave selling luxury handbags for like $30k a pop. I had a job i could not take direction then i started my own business. I launched in 2018 and then i found out that anyone can copy you at anytime. I had kind of a breakdown in 2024 when everyone started to copy my whole business. I kept going . Kept learning SEO / Google ads / enginerring now with Ai its the best thing that ever happened to me. I learned how to build feaures. I am not rich but i have freedom of time. I LOVE working out during the day. I love waiting for my daughter to get home from school. We have dinner together every single day. We went to mexico and NOTHING changed for me. I was still working making money. for me since i can't work in tech and no tech company will hire me. I only know sales so i think for me i had no choice but to launch a business. I am very happy right now. I hope i don't go out of business. idk if i have any suggestions but if you are not good with sales get good at it. Good luck to all the small players out there. i wish you success. This is a very good article i could never write like OP thank you for sharing. Just adding my 2 cents here.

Unemployment or dislike for authority also forced me to go into this

It's more like an occupation

"Survivors Are Loud; Statistics Are Quiet", is it just me or is that "Foo is Bar; Baz is (the opposite of) Bar" speech pattern one that LLMs prefer for weird reasons.

This is a observation, not a judgment.

(That would be another one: "This is a Foo, not a Bar")

If you find that interesting, look at Stephen Hayes' Relational Frame Theory which is the inspiration for his ACT theory of therapy.

But he basically breaks all communications into patterns like those.

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