Why Ambitious, Talented Young Individuals Fail


My peers and I are at a level of professionalism in which we are getting approached about being mentors. It’s flattering. But it also gives us pause because it’s a double-edged compliment: They think there’s something to learn from us. On the one hand, they want to learn about our skills and our story — how we got where we are.

Outside of a formal internship, though, what we all agreed on is that typically you don’t need to ask someone to be your mentor; it just sort of happens organically and invisibly. People will naturally start orbiting you and asking you questions. They’ll be eager. They won’t even realize, probably, that’s what they’re doing — they’re just drawn to you and your experiences and will either put what they learn from you into practice themselves or realize it doesn’t interest them after all.

The other edge of the double-edged compliment is that anyone who wants to start their own business or pursue a skill they have to operate outside the traditional employment structures — they all feel they have something special about them. And they do. And we do. But I think the mistake rookies and people heading up the ladder make is they confuse what makes them special in the first place (their talents) to also make them so special they’re precluded from doing what’s required to succeed. Truth is, there are no shortcuts to succeeding — people, in my experience, think there must be some sort of fast-track way to get what they want, and there’s no way the answer is to just work hard.

But the truth is, yes, that is the way to succeed. It might take years, and if that’s enough of a deterrent for you to not even try, well, then, guess what: A mentor isn’t going to help you with that. Maybe you need a cheerleader instead? The best a mentor can do is offer advice and the occasional word of encouragement: A “this is how bad I had it when I was coming up” or basic advice on how to carry yourself.

But we won’t do the work for you. You gotta do that yourself. 

David Wolinsky is a freelance writer and a lifelong Chicagoan. In addition to currently serving as an interviewer-writer for Adult Swim, he's also a comedy-writing instructor for Second City and an adjunct professor in DePaul’s College of Computing and Digital Media. (He also co-runs a blog behind the DePaul class, DIY Game Dev.) He was the Chicago city editor for The Onion A.V. Club where he provided in-depth daily coverage of this city's bustling arts/entertainment scene for half a decade. His first career aspirations were to be a game-show host.

Contact Us