How many bosses did you have in your first 10 years of working? That sounds awful and I’m sorry you went through that.

I used to work at a very large company, and perhaps because of that, when I couldn’t get something done on time, asking for help was something I felt empowered to do.

Now that I’m a co-founder of a much smaller company, we don’t have as many people to help if someone gets overworked... but that means we’re much more careful about asking for too much over a given amount of time. Software development comes with all kinds of unknown unknowns when you first begin on a change, so we generally plan for that.

Having a small team - and strongly wanting everyone to have a 40 hour week, not a 60 hour week - has helped me understand how essential prioritization is to our success.

At least 19? I worked a few jobs, then had two different mini-stints for about 4 years each, moving through the ranks.

I appreciate your empathy, and I'd agree - one of the things I learned and used over and over again is that if you want good work out of people you need some sort of alignment of outcomes - if they trust you to treat them right and have reasonable expectations and goals, then you can build a really excellent team.

Thanks for answering! Out of curiosity, were these bosses all at technology companies, in what would frequently be considered a "white collar" job?

Definitely white collar, but not all tech companies. Real estate, call centers, then operations/support for tech companies moving into data management and DBA work.

I guess in retrospect the call center stuff was somewhat blue collar, but its really knowledge and process work instead of making things or buildings things.