Peddle Downhill: 4 Mistakes to Avoid When Seeking Your Dream Job

I remember riding my bike that one summer day with my big brother Mark.  We were riding side by side “Chips” style when it started.  We’d been casually gliding down a hill around the corner from my house. We were probably on our way to a pick-up baseball game at a friend’s house. Maybe I was 10 and he was 12 – who can remember. What I do remember is that we were gliding down a hill when I decided I wasn’t going fast enough. I wanted to push it a little; you know, drop the hammer. So I started to peddle downhill. Mark, who has always been more of a break down hill type of guy, began to immediately let me know his unease with my sudden burst of peddling fury. As I began pulling past him down the hill I heard his voice trail off as I blew past, and continued down the hill “Chris, you don’t peddle downhill, you BREAK downhill”. I could barely make out the last few words, but I got the gist. I didn’t care, I wanted to peddle.  By now I was hunched over, leaning into the wind which was making my eyes tear. I was peddling as hard as I could downhill. It felt amazing; I was pushing myself to the limit. It felt right, it felt comfortable; I was following my bliss, finding my voice, and peddling downhill. peddledownhill

For years I used this story as the definitive tale to articulate the difference between my brother and myself.  We’re 26 months apart and as we’ve grown older we’ve come closer to looking like twins than either likes to admit.  So when the question is posed, this story suits me just fine.   I wore this story like a badge. I’m the wild one. I’m the one that jumped at the chance to live abroad in Belgium, and took the job in London. I partied too hard, I pushed. Mark is steady Eddie. He plans, he executes, and he has laser focus. He’s the attorney; I’m the Internet Sales guy. Nuff said.

I always peddled downhill. I never questioned that impulse. It was natural to me, and it served me well. Until a certain point in my career.

At some point I stopped peddling downhill, and I suffered the consequences. Here’s a short list of some career mistakes I made that I hope you don’t as well.  Follow your gut, being true to yourself, listening to the voice inside you and peddle downhill.

Mistake #1. Allow others to guide your career (headhunters etc)

Mistake #2 Chase a big payout

Mistake #3 Seek  security rather than excitement

Mistake #4 Seek rolls  you can easily perform rather than challenge yourself

Who’s the Coach?

I’m Chris Dessi.

Tech entrepreneur. Author. Talking head.
But before any of that—I’m a builder.

I’ve spent the last 20+ years helping companies grow:
From dot-com chaos to SaaS scale-ups to AI-powered everything.
I’ve sold software across continents. Closed $32M in deals using AI.
Built and exited businesses. Bombed a few too. All of it made me sharper.

Today, I run Torque AI, a marketing automation platform built for the 99%.
Small business owners. Solopreneurs. Operators with too much to do and not enough support.
We give them AI superpowers—without the hype, the jargon, or the BS.

I’m also the founder of AI Summit NYC, where real business owners come to learn how to actually use AI to drive revenue.

When I’m not building, I’m writing books, speaking on national TV, and coaching execs through reinvention—with a baseball bat in one hand and a meditation app in the other.

I believe reinvention is our greatest asset.
I believe AI isn’t the threat—it’s the test.
And I believe if you’re not adapting, you’re eroding.

Let’s build something that matters.

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