Book Kenny
life advice for work

3 Lessons I'd Give My Younger Self That Would Have Saved Me 10 Years Of Chasing Business In The Wrong Directions

entrepreneurship identity leadership personal growth ponderings work Jul 06, 2026

If I could sit down with the founder I was 10 years ago, I'd bring 3 things to that conversation...

Rule #1: Find Your People Before You Need Them

I spent years solving problems other people had already solved.

Asking for help felt like admitting defeat, so I avoided it until I ran out of options.

Collaboration is a discipline you build during the calm, long before you need it.

Find your mentors early. Build your circle before you're desperate for one.

(also, ask me about masterminding has changed my trajectory...)


Rule #2: Take the Risk Before You Feel Ready

I waited years for certainty before making a real decision.

Certainty never showed up.

Every risk I took that actually mattered felt reckless walking into it. Waiting for a guarantee is fear wearing a business suit.

Take the leap while you're still scared. That's usually the sign you're onto something real.


Rule #3: Your Worth Was Settled Before You Built Anything

This one took me the longest to learn.

I measured my worth by how many launches I shipped and how busy I looked to other people.

The business had good months and hard months. My sense of worth followed right along with it.

You are an image bearer before you are a founder. That was true before this business existed and it's true no matter what the business does.

What would you tell yourself 10 years ago? I'm curious what lessons you'd come up with.

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