Mentorship? Council? Bro, I have no idea how to even ask for help

Back in 2006 (23) I was failing at a job where I worked with some really cool people. Ramit, tried helping me through it. It's hard to remember all the conversations but I do remember him saying (paraphrase):

"Darren, you're not going to find the answer to this problem by sitting here all day. You have to go out and ask somebody for help."

Uh, what? Two things rang through my head in that season of  life:

1: How the heck do you even ask someone for help?

I grew up kinda hood so the idea of asking someone to coach you through a problem was so foreign to me. Seeking council and guidance wasn't ever modeled out.

The idea of asking someone for help looked like, "Bro, can I borrow twenty bucks?" or "Yo, can you come by this weekend and help me move?"

It was not, "Hey, I'm responsible of growing  installs by 20% this month. Can you teach me how to do that?"

2: Isn't asking for help a sign of weakness?

I've done pretty good for myself up to this point. Sure I'm struggling, but why do I need someone else's help? Let's just keep smashing my head into the problem until a path forward appears!

Try This

If you've never asked for help here's a script:

"Hope things are going well for you this week! Hey, I've got X challenge at work. Could I get 15 minutes of your time over Zoom or maybe a phone call on your drive home? I'd love to hear your thoughts on how I should be thinking about this?"

Asking people for help is both art and science. The more you do it the better you'll get at it.