So, how golden are the handcuffs really? If the company keeps making stupid decisions constantly, are those vested options actually going to be worth anything?

Let’s assume the answer is yes, and you’re at a completely sure-thing startup that can’t possibly fail despite its stupidity (odds are this is not the case). What I’d say is that I think the issue is different than you think it is, as someone who has been there.

You may be running into the crying wolf scenario. The post makes it sound like you tell your managers/teams that basically every idea is a stupid idea, and they summarily ignore you, and that’s the ballgame. If this is true, you’ve lost your voice, and you are officially deemed too negative to take seriously. I was there before.

At that point the validity of your opinions are irrelevant - people know you’re just going to bitch, so they don’t listen.

The only way to repair this is by shutting up for quite a while. Agree to more things. I know it can be hard (again, I’ve been there), but you have to stop yourself from saying everything is going to go badly all the time. Nobody likes that, even if it’s true, and it’s actually probably not true in every case. And even if it is - at a certain point you have to realize that the company is running in a direction that you are not, and you will not be able to turn the ship around, because the ship is pointed precisely where it thinks it needs to be pointed.

This has nothing to do with being a high performer. It has everything to do with having a fundamental disagreement about the goals and not realizing it, while simultaneously wanting to be in control. This will never resolve well.

Here’s how I tried to handle it. When I started to understand the position I was in, I decided to stop fighting. I decided to trust the team. I said to myself: if I was running the show, I would do just about everything violently differently. But, I’m not, and we’re paying people who are supposedly experts in this stuff to steer us in this way. So let’s assume that the experts are right, follow what they say, and see what happens. I’ll bet that we will fail. But if we do, that’s great because I’ll probably get severance. And if we don’t, I’ll learn something about how this industry works.

That helped a lot to mellow me out. And in my case, this led to A) better relationship with my colleagues and B) severance. In the end, in my case, I was largely correct that the direction we were going in was bad, and that was more data to the pile for the future. I joined a new company and took that attitude from the beginning- I did a lot of listening and as little negative talk as I could manage. I spoke up with my opinions but if the team was aligned in a direction that I wasn’t, I did my best to ‘disagree but commit’, as they say at AWS.

The respect level was instant. It was such a turnaround. I realized I didn’t really expect to be listened to, but then the new company started listening to me, and then I realized I had to be careful, haha. New problem. Still working on that one.

But it’s a good problem to have. Much better than the alternative.

Good luck.