Fix-It Friday on a Sunday: Mentorship - Stop Waiting, Start Reaching Out

Even the “untouchable” people are figuring it out every day. Stop disqualifying yourself from asking for help.

The Story

It was 2018, again. Post-NYC trip (if you haven’t read that story yet, it’s all here and here), back in Miami. I wasn’t ready to leave the Dolphins yet (I hadn’t figured out anything at this point), but something inside knew it was inevitable. Training camp was in full swing. The days were long, insanely hot, and exhausting. I’d come home and collapse into my chair—zoned out, stuck in the woe is me loop. Feeling sorry for myself. Doing nothing about it. I was paralyzed from overthinking and under-doing.

I knew I needed perspective. Unbiased, external, no emotional or personal strings attached. Someone outside the Dolphins/Jon Willey bubble who could tell me the truth I couldn’t figure out how to tell myself.

That’s when I thought of riCardo Crespo.

We’d met at an NFL creative conference a year or so before through Surf and grabbed coffee before we left. I respected him. His résumé spoke for itself — lead creative for different departments at Nike, Mattel, 20th Century Fox, Saatchi, Chiat/Day. But more than the logos, he carried a presence and kindness that cut through noise. And I had his number. (Read and watch more about riCardo here).

So I finally said, fuck it. The worst he can do is say no.

I texted him and asked if he’d be open to a call. He said yes. Not surprised, but very thankful he did. The next week, we talked for half an hour or more. No fluff. No pep talks full of overused cliches and platitudes. He listened. He asked questions. And then he gave me a handful of blunt truths. I opened my Notes app during the call and typed them out so I wouldn’t forget, because at that point my brain was not working correctly and remembering anything was a challenge. Here’s what I jotted down:

• Think big, talk small.

• Don’t mistake being liked for job security. What reputation equity do you have?

• Purpose > passion.

• What is my purpose? What is my why?

• Do you need your job, or does your job need you?

That call didn’t fix me overnight. But it gave me clarity I couldn’t generate on my own at that point. It gave me a direction to move toward instead of just sitting in that chair.

---

What I Wrote Down — Then vs. Now

Those five lines are still in my notes app, as you can see above. At first, they felt heavy as hell, like riddles I wasn’t smart enough or strong enough to figure out. Honestly, some of them pissed me off because I knew the amount of work ahead of me to make change.. and I was so tired. But looking back now, I read them completely differently. They hit harder, but they also make a lot more sense. Here’s what they meant to me then, and what they mean to me now: