37 CEO Lessons: Finding Brilliance in the Mayhem
I share these lessons with you as I turn 37!
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Yes, this newsletter is late—apologies! But I have a pretty solid excuse: I turned 37 yesterday!
I landed in La Paz (literally flying into "peace") in Baja California and spent the day by the ocean, watching whales come so close to the shore that my heart skipped a beat more than once. I’m taking it as a lucky sign for the year ahead. Sharing a piece of my happy day with you!
As I watched the sun melt into the horizon, I thought, What a mayhem this last year has been! And with that, I decided to share 37 lessons from my journey as a first-time CEO—raw, real, and shaped by both the chaos and the clarity that comes with it.
So here they are.
Mayhem isn’t just part of entrepreneurship—it is entrepreneurship.
It’s the sleepless nights, the pivots you never saw coming, the moments of doubt followed by breakthroughs you couldn’t have planned. It’s the willingness to step into the unknown, armed with nothing but a vision and an unshakable belief in what you’re building.
As I turn 37, I’m reflecting on what it really means to be a first-time CEO. If I’ve learned anything, it’s that success isn’t about avoiding the chaos—it’s about embracing it. It’s about trusting yourself when no one else does, speaking up when your voice shakes, and daring to build something the world has never seen before.
Every entrepreneur is a genius—not because they have all the answers, but because they choose to take the leap. They dare to believe before there’s proof, to create before there’s certainty, and to move forward when everything says, "Play it safe."
In honor of 37 years of life and lessons, here are 37 truths about being a first-time CEO—insights born from chaos, resilience, and the relentless pursuit of something greater.
Mindset & Authenticity
Mayhem is where the magic happens. Chaos isn’t failure; it’s the birthplace of innovation.
Your weirdest ideas might be your best ones. The market rewards originality, not fitting in.
Authenticity attracts the right people. Fake it, and you’ll build a business for someone else, not you.
You’ll never feel “ready.” Do it anyway. Confidence comes from action, not preparation.
Doubt is part of the process. The difference between success and failure is who keeps going.
Leadership & Speaking Up
If you don’t define your vision, someone else will. Own your voice.
Hiring isn’t about skills—it’s about values. Teachable skills; unteachable integrity.
Your team mirrors you. If you’re chaotic, they’re lost. If you’re clear, they’re empowered.
Hard conversations make you stronger. Avoiding them weakens you and your business.
People-pleasing is the fastest way to lose control. Leadership is about respect, not approval.
Bravery & Decision-Making
Jump before you have a parachute. The best ideas unfold mid-air, not before takeoff.
Screw perfection—speed wins. Iteration beats hesitation every time.
Your first ‘big idea’ won’t be your last. Get attached to evolution, not ego.
Say no 10x more than you say yes. Focus is your greatest asset.
Bet on yourself, even when no one else does. If you don’t, why should they?
Money & Business Strategy
Cash flow is king; profit is queen. Without them, your business is a hobby.
Price for value, not insecurity. Charge what it’s worth, not what makes you comfortable.
The market doesn’t care about your feelings. Test, iterate, and follow data, not emotions.
A business without sales is just an idea. Selling is serving—learn to love it.
Your network is your safety net. Relationships build businesses, not just strategies.
Resilience & Failure
Rejection isn’t personal—it’s data. Use it to improve, not retreat.
You’ll fail, and then you’ll get better. There’s no shortcut; there’s only learning.
Burnout isn’t a badge of honor. Resting is a strategy, not a weakness.
Some people will cheer when you fall. Keep building anyway.
Ego kills businesses faster than bad ideas. Stay humble, stay learning.
Creativity & Chaos as a Superpower
Mayhem fuels creativity. Your best ideas will come in the messiest moments.
Constraints create innovation. Less money, time, and resources force better solutions.
Don’t fear reinvention. The best companies don’t just evolve; they revolutionize.
Weird wins in marketing. Safe messages get ignored; bold ones get shared.
What’s obvious to you is genius to someone else. Don’t underestimate your unique perspective.
Legacy & Long-Term Thinking
Build for impact, not just income. Money follows meaning.
You won’t be everyone’s cup of tea. But you’ll be someone’s absolute favorite.
If you only chase trends, you’ll always be behind. Set them instead.
Success is boring. The real fun happens in the struggle, the growth, the transformation.
Your business is a mirror. It reflects your strengths, weaknesses, and deepest beliefs.
The journey is the reward. You’ll never ‘arrive’—enjoy the ride.
The best leaders don’t tame the mayhem—they learn to dance with it. That’s where the real brilliance is.
If you’re a first-time CEO, know this: The chaos will never fully disappear. But within the uncertainty, missteps, and moments of doubt, there’s an opportunity to create something extraordinary.
Here’s to another year of mayhem, growth, and finding brilliance in the mess!
The First-Time CEO Podcast Update
Episode 5 with one of my favorite solopreneurs comes out this week (follow me on socials to stay up to date below), and I’m super excited about it. I also recorded three more last week, so I’ve got great material for you to listen to and watch for weeks ahead! It’s packed with breakthroughs and insights for modern leaders and new CEOs. Besides, unbelievable, but Season 1 is almost over, and I’m planning a surprise for you! So follow me and the show to not miss a thing:
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