After college, I knew exactly what I wanted to do.
I wanted to be in the music business.
Through a series of events that are better told over a bourbon, I got connected with Jimmy Iovine when I was 27.
If you don’t know the name, Jimmy Iovine is one of the most influential people in the history of the music industry. He’s produced and advanced the careers of more superstars than you can imagine, including John Lennon, Bruce Springsteen and Tom Petty. On top of that, he co-founded Interscope Records, and started Beats with Dr. Dre, which Apple acquired for $3 Billion.
Jimmy and I sat down and talked for awhile.
It was a great conversation. He actually told me I reminded him of himself when he was younger.
To this day, that may still be the greatest compliment anyone has ever given me.
The next week, Jimmy invited me to a get together at his house.
I never went.
Yep. You read that right.
I didn’t go.
One of the most successful people in the business I desperately wanted be known for, basically said, I really like you. I want to help you. Come on over and I’ll introduce you to some other people who can catapult your career
And I said no.
Well, technically, I didn’t say no.
I just never went.
Which may actually be worse.
The Lie I Told Myself
At the time, I had all sorts of reasons for not going.
I was busy. I already had plans. The timing wasn’t great. Whatever.
In the end, that reasoning was all a truckload of crap.
Because the harsh reality hurts too much.
I was scared.
I was scared I’d walk into Jimmy Iovine’s house, sit across from him, and in a few minutes he’d realize he’d made a huge mistake.
Maybe I didn’t remind him of his younger self after all. Maybe he’d find out I was a fraud. An idiot.
What’s an even harder peach pit for me to swallow is my belief that accepting his help meant admitting that I needed help.
And I thought needing help meant I wasn’t good enough to do it myself.
So instead I did what I became exceptionally good at doing whenever I was scared.
Nothing.
I let the opportunity disappear.
And I never got to speak with Jimmy Iovine again.
I Did This For 15 Years
I hope you’re angry at me about that Jimmy Iovine story. You should be. I’m angry with myself.
And the worst part is that it wasn’t an isolated incident.
I spent the first 15 years of my career believing I was supposed to be an expert at everything, without anybody else’s help.
If I didn’t know something, I’d figure it out myself.
If I was struggling, I’d work harder.
If I was stuck, I’d keep digging until I somehow, hopefully, got myself unstuck.
Asking for help felt like revealing to the world that I wasn’t smart enough. Which, in retrospect, is fucking absurd.
Nobody is an expert at everything. Nobody builds anything meaningful by themselves.
I know that now.
I didn’t believe it then.
Or maybe I did.
I just didn’t believe it applied to me.
Then I Got To Be On The Other Side
Last week I sat on a panel for students at Hamilton College, my alma mater. I was honored to be asked, and shared the panel with a couple of really impressive people.
We talked about careers, opportunities and taking risks. All the stuff you’d expect a panel of execs to talk about to current college students.
But the three of us kept coming back to essentially the same message:
Ask for help.
We kept telling the students to put themselves out there.
Talk to people. Tell them what you’re trying to do. Ask for advice.
Because here’s the thing I didn’t understand when I was younger:
People actually want to help you.
Seriously.
I’ve said some version of that hundreds of times now. I just haven’t found the time machine that would allow me to say it to my younger self, and Lord knows, nobody else convinced me of it back then either.
And I Got A Message
The day after the panel, one of the students sent me a LinkedIn connection request.
He told me that it is difficult for him to put himself out there, but he’d heard what I’d said, so he wanted to push himself and reach out.
I read his message a few times. Because he sounded like somebody I used to know.
Me.
I was that kid.
I was the same one standing at the same door, wondering whether I should knock. And if I did, wondering whether I had the guts to stand there and talk to the person on the other side.
This time, I got to be the person on the other side.
Which Is Basically My Entire Job Now
There’s an irony to all of this that didn’t occur to me until I started writing this piece.
I spent the first part of my career refusing to ask people for help.
Now I’ve built an entire business completely focused on helping people.
I’m a coach. A mentor. My clients call me their leadership therapist.
High performing people call me when they feel stuck. When they’re struggling with something they can’t quite figure out. Or when they keep having the same problem with their team, and all the other attempts to fix it haven’t worked.
I help give them a new perspective on the problem.
I’m doing for people what I really wish somebody had done for me.
And I have to admit, I’m really good at it. Because I’ve been in your shoes. I’ve lived with your problems and I know the way out.
I can help you see the thing you can’t see because you’re standing too close to it. Which is exactly what I needed way back when.
Yeah, maybe I still would’ve made the same mistakes. Who knows.
But maybe, just maybe, I wouldn’t have spent 15 years of my life making some of those mistakes over and over again.
The Part I Still Haven’t Forgiven
I’ve had a great career. Don’t get me wrong. I’m grateful for all of it.
I’ve built three companies. Sold all three. I’ve worked with some amazing people, had some incredible experiences and somehow ended up with a life I’m pretty damn happy about.
That said, I still haven’t forgiven that younger me for not showing up to Jimmy Iovine’s house when the opportunity arose. I probably will never forgive myself. But I didn’t tell you that story because I want sympathy.
After all, maybe nothing would’ve happened.
Maybe Jimmy and I would’ve talked for 30 minutes, I’d have left and my life would’ve gone on exactly the same as it did.
Or maybe one conversation would’ve changed everything.
Unfortunately I’ll never know.
And that’s the shitty part of this whole thing.
It’s not just the opportunity I missed.
It’s the life I never got to find out about.
I don’t want you to make the same mistake.
Now It’s Your Turn
So let me ask you the question I wish somebody had asked me.
Where do you need help right now?
And are you actually asking somebody for help? Or are you doing what I did and trying to just figure it all out on your own?
Because asking for help doesn’t mean you’re incapable of doing it yourself. It doesn’t mean you’re an idiot.
Sometimes it just means you’re smart enough to realize that you don’t have all the answers.
And you don’t. Nobody does.
So do me a favor - when someone opens the door for you…
Walk in and start talking.
Speaking of which - I’ve got something new that I know you’ll love.
It’s called The Best Leadership Problem Lab. You show up with a real problem and a group of experts helps you solve it.
That’s the whole thing. You walk in with problems and walk out with solutions.
There are curated groups for founders, VPs, coaches, and working mothers. Sessions cap at 10-12 people.
If you’ve been trying to figure something out on your own for too long, this is your door. It’s time to walk in.
