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After one of our live events a few years ago, I was walking back with an attendee.
We were chatting about the behind-the-scenes of running a business: launches, goals, things that work, things that don’t.
At one point, she asked me, “How do you keep going when things don’t work out? You always seem to have it together.”
I laughed, because that couldn’t be further from the truth.
Yet, I still had a system to help me fail fast, and bounce back just as fast.
That’s the curse of being someone who tries a lot of things.
From the outside, it looks like momentum. On the inside, it can feel like an emotional rollercoaster.
One big cycle of “this is it!” and “why isn’t this working?” on repeat.
So I gave her my honest answer, one that somehow stuck:
“Being your own boss is constantly second guessing yourself and your ideas”
Some days you’re on top of the world.
Others, you’re spiralling because your latest launch flopped and you’re three coffees deep trying to make it all make sense.
Over 11 years, after launching more than 50 courses, products, and experiments (for myself and clients) I’ve learned one thing:
You have to fall in love with the process, not the outcome.
Because when you tie your worth to results, every dip feels personal.
But when you commit to learning, iterating, and experimenting, you stop fearing the flops.
HOMEWORK: Next time something doesn’t land, take 10 minutes to write down three things you learned from it.
YOUR HOMEWORK ✍️
Next time something doesn’t land, take 10 minutes to write down three things you learned from it. Don’t talk yourself out of it.
You Should Drive for Daylight
In her book The Creator’s Code, Amy Wilkinson talks about the idea of “driving for daylight.”
It’s something pilots do when flying through darkness.
Instead of staring at what’s right in front of them (which could cause them to crash) they focus on the horizon, on the light ahead.
That, to me, is the perfect metaphor for entrepreneurship.
When a launch underperforms, a campaign doesn’t click, or a product just doesn’t land, our instinct is to obsess.
We replay the numbers, tweak the copy, spiral through the what-ifs.
But, brace yourself on this one: not every idea is meant to work. Not every offer is meant to scale.
Driving for daylight means learning fast and letting go faster.
It means focusing on the light ahead, not the pothole you just hit.
YOUR HOMEWORK ✍️
Next time something does not go to plan and you need to decide next steps, run a calm audit:
What’s changed: audience, timing, energy?
What’s the data actually telling me?
Is this still aligned with what I want to be known for?
Give yourself 24 hours before making a decision. Detachment brings clarity.
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What This Looks Like in Real Life
My first ever course was a marketing program for yoga teachers.
I loved the idea: there was NOTHING like it out there. Poured my heart into it. But the market wasn’t ready. The timing was off. I ran it once, and that was it.
Was it a failure? Not even close.
That course taught me more about market fit and timing than any “win” ever could.
That’s what driving for daylight looks like in practice:
Evaluating why something didn’t work, and deciding whether to adapt or release without attaching it to your identity. Yes, easier said than done.
YOUR HOMEWORK ✍️
Before moving on from an idea, write down:
What actually worked (even small wins)
What you’d never repeat
What you can repurpose for another project
That’s how you extract the gold and move forward lighter.
“The difficulty lies not so much in developing new ideas as in escaping from old ones.”
– John Maynard Keynes
As the launch of the The Customer-Driven Marketing Handbook is approaching, I have once again put on my thinking and experimented with yet one too many things to explore for it.
Eventually, I launched a website and a sneak peek audio preview, and so far it looks like the heaviest hitter.
Forever driving for daylight here!
Your value isn’t measured by how many ideas you launch.
It’s in how you evolve through each one.
So when something doesn’t work, remember: you don’t have to white-knuckle your way through it. You get to pause. Reflect. Learn. Shift gears.
You get to drive for daylight,
Fab ✌️
GRAB A COPY OF MY NEW BOOK 📖
Fifteen years of marketing experience condensed into one book. The Customer-Driven Marketing Handbook is about building relationships using marketing as your superpower. But also a book about being human in your marketing, regardless of the tools, trends or changes that this crazy world throws at us.