Last week, we talked about one huge question, “How the hell are you supposed to have a career in tech in 2026?” That’s pretty specific to this current moment, but there are some timeless, more perennial questions I’ve been sharing with friends for years that I wanted to give to all of you. They’re a short list of questions that help you judge whether a job that you’re considering is going to crush your soul or not.
Obviously, not everyone is going to get to work in an environment that has perfect answers to all of these questions; a lot of the time, we’re lucky just to get a place to work at all. But these questions are framed in this way to encourage us all to aspire towards roles that enable us to do our best work, to have the biggest impact, and to live according to our values.
Lmao, nowhere I’ve ever worked has had a single one of these factors, what a pipe dream
Do you have evidence of leaders in the organization making hard choices to do the right thing?
This went from a hard yes to a soft no and I don’t know if it’s soul crushing but it feels super crappy.
Good questions
What’s the lived experience of the workers there whom you trust? Do you have evidence of leaders in the organization making hard choices to do the right thing?
Very helpful, and very hard to get around if you don’t already have a connection.
Though in my experience, people will tell you a fair amount about the organization indirectly; and will often answer direct questions.
My org seems to be making hard choices to do the wrong thing at the moment. Hope I am wrong.
Agreed I’ve usually found existing employees honest and helpful. Often it’s hard to get an opportunity for an honest conversation before you accept a new job though.
Does your actual compensation take care of what you need for all of your current goals and needs — from day one?
I’ve never had this. Where does one find a job like that today lol. I want to say the majority of people actively do not have this unless they are in a situation where they have been able to live more frugally. Inflation and greedflation have made any pay increases I’ve received in the past decade basically non existent.
That being said I’m basically supporting a family of 4 on a salary of 1.5 people.
