I'd much rather be told that six-figures is a sure thing for basically eternity than know one day I could lose my job without warning, but hey maybe we'll (read: the founders) will become billionaires / millionaires.

Playing the startup lottery is a dumb prospect for short-sighted 20-year olds. Absolutely nothing wrong with joining a startup (I love them and plan on working at them for the foreseeable future), but you have to go in with the hedge that it might go to zero unless they plan on avoiding unsustainable VC-funded growth by finding sustainable profit

High and stable income put into investments and savings then leaving and founding your own bootstrapped company is the way to go. I'd much rather know I can sustainably increase my income over time than knowing I'll have to hit it big to not be in debt or lose someone's money.

VC is a fool's game. You have to be crazy enough to think you'll win, which is great for those huge wins but not so great for the losers who will have dumped 5 years and their sweat and tears to make $0 or have lost money.

You can lose your job anywhere without much warning. The trick is don’t depend on your job for your long term livelihood. Instead, depend on a marketable set of skills and a network that can help you land another job quickly.

1. Going in to work and doing the best job I can.

2. Making sure my skillset is marketable and keeping my resume continuously updated

3. Keeping in touch with my local network of recruiters.

In 20+ years, it’s never taken me more than a month to get a job and once, I left a contract (long story) with nothing lined up, met a recruiter for lunch on Monday and had a job offer with a what was then a Fortune 10 company by Thursday[1].

If I worked for myself, I would be constantly hustling for clients, collecting payments etc. Working for a company means money shows up in my account twice a month for exactly the same amount. If the company goes bust, I can find another job. If I want to take a vacation or get sick, other people take up the slack and I still get paid.

I’m no special snowflake, anyone in my metro area that has kept their skills up can easily find a job.

[1] Yes that was dumb luck, the department that I was hired into was a recently acquired startup and their HR hadn’t been fully integrated into the large slow moving bureaucracy.

Btw I think health insurance is the biggest problem here, in the US.

Anyway I didn't mean in any way that being employed by a company was some kind of bad choice, not at all!

As long as the ACA exists, health insurance is available. It's just a cost of being self employed.

On the other hand, it's even easier if you have a spouse that works a stable job. I know a few people (including me) that have spouses that work a low paying government job just for the insurance so they can be more aggressive about their career or start a business. Since I've been married, I've jumped back and forth between working salaried and contracting with abandon.

When you go into it demanding what you're worth and knowing the risks, on the other hand, it's not a fools game. It's a calculated high risk, high reward ride.

I've worked in many VC funded startups, and I've made money on all of them. Mostly not much above a normal job, but I've only ever put in "free" work or underpaid work for short periods, and then compensated with higher income later.

It's about not getting taken in by the sales pitch to the extent that you stop negotiating, and about not overestimating the value of the equity on the table. I typically won't take an offer that I wouldn't have taken in a non-startup without the equity.

If either job comes with a lottery ticket, I guess that's sort of nice?

I think this is the most profound thing I've learned in my career. But an even more important lesson is that you have to find a place where the B.S. is tolerable to you. For some people the politics of a bigco may be impossible to deal with, for others the "another month, another pivot" shiny objects syndrome of a small startup may be the issue.

Every place has B.S. That's why they call it "work" and not "fun". Find a place where the B.S. is tolerable (or, better yet, minimal).

No, it isn't. The "work" is the fact that I am applying my skillset to satisfy my employer's desire whether I feel like it or not; often, that means polishing and grinding at rather boring but rather necessary tasks.

None of that requires bullshit, and calling bullshit "work" normalizes toxic behavior.

I would also like to distinguish between toxic and abusive behavior (which I don't think anyone should tolerate) and a certain amount of B.S. The latter can vary across a spectrum, but is tedious, or frustrating, or annoying, not psychologically harmful.

I prefer to think of it is a finding a bullshit compatible place. All companies have bullshit, but the trick is to find a place whose particular variant of bullshit is compatible with your particular tolerance of said bullshit.

Bullshit compatibility is an important thing!

Smaller company doesn't have to mean less bullshit. It's just a different kind of bullshit.

They can take the form of your manager, or colleague, or anybody in the company and the option is to either deal with it or bail on the company. In a larger company with many teams, you can usually route around such people by switching to a different org. Plus their power is often more constrained because there is just more people in the company.

401k match is nice, but it's part of total comp. I don't want to be promoted into a job where I'm responsible for others, thanks -- it's more work, I'm not good at it, I feel bad about fucking up the careers of my subordinates, and it doesn't give me the same fulfillment of doing my normal stuff.

In exchange for a chance of promotion, I get to deal with a purchasing process that makes it nearly impossible to pay a recurring vendor; I get to do performance review cycles twice a year (no wait, there are actually two hidden mid cycle reviews, so 4x a year), and deal with co-workers who don't give a shit about actually getting things done, they just give a shit about appearing to have 'impact'. I get to deal with 'up or out' policies. I get to deal with pass the buck bullshit trying to get my state income tax changed to reflect where I work and where my desk is. Oh and so many meetings, because nobody is willing to be responsible for making decisions.

I'm willing to put up with this shit because of equity from an acquisition, but I was much happier with the typical bs at the startup, which was mostly that I ended up owning a lot of stuff I'd rather have offloaded onto IT because we didn't have IT, and because I worked at a rinky-dink ISP in the 90s so I knew how internet email worked.

But mooreds upthread is right, it's not a matter of finding a place with no BS, it's a matter of finding the BS that is most tolerable. I clearly have a preference.

I've interviewed at large places and they either blew me off because no one cares (why would they) or they had pointless interview questions (cough google)

When you consider company equity to be a nest egg but don't actually have any control over whether it'll be a success or not you're making a bet. I don't blame anyone who isn't interested in that game.