Feel with your head. Think with your heart.
Someone gave me that line years ago. It wasn't wordplay. It was the best business advice I didn't know I needed, and it took me two decades to understand it.
I've spent nearly twenty years helping companies grow, and if you compressed all of that advice down to its essence, it would sound familiar: name your blind spots out loud before they name you, listen for what the data can't tell you, trust the people who've earned it, and when the evidence is thin but the conviction is loud, move anyway. I've watched that advice change companies. I built a career on giving it.
Good advice which I gave it to everyone but myself.
This year I finally turned it inward, and here's what that actually looked like:
- 🔎 I asked people I trust, people I consider smarter than me, to tell me where I can improve. Then I applied what they said instead of defending myself.
- 🧭 I learned to listen to my doubts, and to sort out which ones were actually mine versus the voices of naysayers I picked up somewhere along the way.
- 👂 I challenged myself to find the nugget of wisdom even in voices that don't know me or understand what I'm building. An outside eye sometimes catches what a friendly one won't.
- ⚡ I learned to feel through the feeling and into the emotion underneath it, so it could add energy and power to my decisions instead of pulling them in opposite directions.
- 🌱 I built the unglamorous scaffolding that holds all of the above up: meditation, habits, real time carved out for no work and no screens.
And when an unproven bet showed up that felt right in a way I couldn't fully argue yet, I went all in.
Here's what the motto means to me now. Thinking with your heart is slow thinking at the emotional center. Conviction does work that logic can't finish, and the way you tell conviction from a mood is time: a spike of emotion fades in a day, while the real pull holds its direction for months. Follow it long enough and it becomes Jack Sparrow's compass.
Feeling with your head is the other half, checking the excitement against what you actually know. When my gut and my logic line up, problem-solving is easy, because the core direction is settled and attention turns into high velocity action pointed at the how. Most of us run it the hard way, trying to pick the direction while we're solving the problem, and that's too many variables to hold at once.
Your biggest decisions should not be made in a spreadsheet.
Nothing about my bet is proven yet. That's the point. The companies I've helped most were the ones where the founder took their own medicine, and it took me twenty years to join them.
What's the advice you give everyone except yourself?
