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Not to pitch in with low-value "me too thanks" style replies, but by god does this sum up the last 18 months of my life. Every time I feel comfortable, bam! Something new to keep me awake at night. It's one part exhausting and one part exhilarating and I'm not sure if I could go back to salaried work at this point.

> I'm not sure if I could go back to salaried work at this point.

I hope it's a choice!

I applied for a salaried position at IBM (I think?) for a Product Management position that I could have nailed, through a head-hunter that I knew was covering the position.

He said: "No way, dude. I wouldn't do that to them or you".

I said: "Why not?"

He said: "Because you are a startup guy".

I said: "Hey - I used to work at Motorola. At the global level. Scotland, Malaysia, I lived in Japan, Phoenix and Austin. I was a great corporate droid."

He said: "Used to be. Now you would just get a couple of paychecks into feeling less homeless-bound, and tell your boss or your boss's boss to fuck off and die."

I said: "No I wouldn't".

He said: "Yes you would - and you can't change my mind".


In my town, I am apparently branded "a startup guy".

Dude, I think the headhunter may be right. Just imagine when (and this is a when not an if) you are demanded to do an insanely stupid thing which you, your team, and your customers hate. It makes no sense but must be done asap. When you ask for justification, it’s because the VP, who never leaves his office except for extra long work lunches with the other executive staff, said it must be done. No logic, no reasoning, no arguing - just get it done. You have two choices:

1) Eat shit and do the stupid thing while a small part of you dies.

2) March into the VP’s office, tell him to fuck off, and walk out like a champ.

Which option do you choose?

Ha! I remember a meeting at Intel, Scottsdale, I think, with their old x386+DRM/crypto-coprocessor chip, where one of the directors (VPs?) got up and stood on the conference table, and urinated on the stupid proposal.

It was very rude but pretty declarative!

In any case - I would never have the moral rectitude to make that kind of statement.

I certainly wouldn't be making a statement in that particular way. But it's impossible to misinterpret, that's certainly true.

Nowadays there are cameras everywhere. I don't want to be (in)famous via a video. My autism can't handle that. But I surely have the balls to say no to my boss. If I'd urinate, no, it would not cross my mind. It's not so much the act itself, but coming up with it (and your position in the hierarchy).

3.) Unless it's extremely unethical -- if it's just hurting my ego, but not actually my person and my ability to sleep well for the rest of my life -- I would do the stupid thing, but tell anyone who asks (and some who don't) that I find it stupid. I'd also start openly musing about what will come after the honeymoon phase (of the VP with their stupid idea), and how the mess might be fixed once it's correctly recognized as a mess. If applicable, I might also be honest to the people who get bitten by that stupid change. Not sharing the interna of the stupid decision, but that it's definitely stupid and why. If I got fired for any of that, I'd walk out like a champ.

I don't backstab, but I also don't lie (which includes people I'm "supposed" to sell the stupid idea to as a great one, starting with myself), I respect the "chain of command" in a way, but never blindly, and wear that on my sleeve. That closes plenty doors, but far from all, and my general experiences with "standing up to my bosses" were surprisingly good. As long as it's because you care about the thing, and the clients of it, and as long as the boss is confident, in themselves and maybe even you, there should be some leeway for that.

I would put it on the bottom of the backlog.

Ahh, the developer version of standing in front of the tanks at Tiananmen Square.

Except I doubt you'd get fired/sued for doing it, which would be the corporate equivalent of what happened to tank man

Yeah, it's braver to stand up to him and tell him no. And I (or 'we', more accurately) have done that. Not to a VP, but to someone from business who insisted we should deploy a new feature to production as promised, when we decided it wouldn't be responsible to do so. And that was a meaningful feature, that we promised to deploy. It's just that we'd come to the conclusion that it wouldn't be prudent to do so at that time, so we didn't. Business guy didn't like it and spent some time screaming at someone (not me, fortunately).

It is absolutely important to be able to say no to people who outrank you.

That was, indeed, the joke.

This hypothetical applies to freelancers too.

I'd been a freelancer for a couple of years, when I talked to a recruiter about switching to a salaried position. He refused. Said there was no going back from freelancing to regular employee. At the time, I thought he was stupid and closed minded. Last year I wasted a couple of months proving him right.

i happily left freelance years ago because i got sick of the hustle of hunting down clients and then convincing them i was worth hiring and then convincing them not to shoot themselves in the foot and then watching them do it anyway and ..... ugh.

I'd happily work for myself with some sort of SAAS thing again, but no way i want to go back to freelancing unless I'm desperate.

There are different ways to freelance. I'm following the coward's way: recruiters ask me for big long-term projects, and I work as freelancer on those projects. Just one project at a time, little time and effort wasted on acquisition, and I still get more money and freedom than a regular employee.

Agree - if you hate your freelancing setup, consider a change in setup. I've basically got it where I have two long term ongoing clients where I'm effectively a part part time remote employee. Weekly checkins, do 10 hours a week, minimal fuss. If you aren't being respected as a professional, consider if your rate is too low. I'm charging $125/hr and it's actually increased the quality of clients. Of course this assumes you are sufficiently good enough to be worth a high rate and can self-manage.

Yeah, definitely a choice! I chose to quit a nice, salaried job in the city and move back to my small hometown and start a contracting business. Stressful, but it's working out great so far!

I worked in startups prior to that so it wasn't a huge leap outside my comfort zone I guess.

he's right though. I tried that. Didn't work. Lasted just over a year.

I've flipped back and forth between 1099 contracts and W2 jobs. What I found was once a stray cat always a stray cat. After running my own show I found my bosses could smell it on me and I got treated different.

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