In this episode, Dave and Jamison answer these questions:

My team often goes out to lunch; I almost always bring a lunch from home. They invite me to come with them, but it feels weird, since I won’t be purchasing a meal from the restaurant. Should I swallow (pun intended) my pride and go with them anyway, or decline their offer? I would bring lunch less frequently, but it’s difficult to predict what days they are going out together.

I’ve been a software engineer for 7 years and it recently occurred to me that product management would be an interesting and fulfilling field that I’d like to give a shot. Is this something I should discuss with my engineering manager or director, or other product managers at my company?

While I think it’s possible these people might be able to help me, my anxious mind can think of many ways that advertising I want help transitioning out of my current role could go badly. I also happen to be fully remote, so I don’t have many opportunities to bring these things up in more casual settings. I doubt I’d be able to get hired as a PM at another company without prior experience, so getting help from co-workers or management at my current company seems pretty important. Do either of you know anyone who’s made this jump? Any tips on getting help without pushing too hard or creating problems for myself?