“Life shrinks or expands according to one's courage.”
Anaïs Nin
My friends stopped talking to me.
My parents were furious.
My wife called me an idiot.
When my kids saw it, they laughed in my face.
And the people I was investing with, they couldn't believe I'd been so foolish.
Why did I decide to write on the internet?
I'd wanted to write for years. Every January, "start writing" appeared on my goal list like a faithful but ignored friend. Three years running, probably more. Each time, I'd find elaborate ways to delay.
I'd have these loose, rambling conversations about writing in my head all the time. I felt that I had a bunch of things to share—insights from investing, lessons from some terrible decisions, and useful ideas and concepts that I'd either learned or adapted to be more comfortable in my own skin, more confident about the things I was doing, and more internally focused from a measurement and progress perspective.
But the flip side was the deep fear I felt about putting myself out there. Talking about things that went wrong, or worse still, trying to talk about some of the things that had gone right and having my mistakes and failures thrown back in my face.
I was worried about what people would say about me, or think about me. I was scared they'd think I was being preachy, or arrogant, or maybe sharing too much.
But as 2024 kicked off I decided this was the year I was going to do it. I think.
Procrastination By Design
First, I needed a brand. Then a website. Then the perfect blogging platform.
For four months, I worked with Ben, a designer I'd found on Upwork, defining fonts and colour palettes for Own The Now. We built Pinterest mood boards, debated fonts and their styles, and crafted brand guidelines.
Ben was patient with my brand newbie questions, probably sensing I was using design as the world's most expensive form of procrastination.
When we finally launched the website in April, I ran out of excuses. Everything was ready - except my courage.
The truth? I was terrified of being found out.
Not as a fraud, exactly, but as someone whose unconventional path didn't fit neatly into dinner party conversation. How do you explain wearing multiple hats - investor, coach, volunteer, dad, part-time Uber driver for kids' activities? How do you admit that your wildly successful wife sometimes makes you feel smaller, not because of anything she does, but because of everything you're not?
I can pinpoint the exact moment everything changed. Early morning, sitting in my office during what I call My Morning Sanctuary—that sacred time before the family wakes. I was reading The Art of Possibility by Benjamin and Rosamund Zander.
Somewhere between finishing Chapter 7, "Being Present for the Way Things Are," where they write:
"Being with the way things are calls for an expansion of ourselves. We start from what is, not from what should be; we encompass contradictions, painful feelings, fears and imaginings and—without fleeing, blaming, attempting correction—we learn to soar, like the far-seeing hawk, over the whole landscape."
And Chapter 8, "Giving Way to Passion," where they explain:
"The second step is to participate wholly. Allow yourself to be a channel to shape the stream of passion into a new expression for the world."
I felt some kind of release. They introduce this concept: BTFI—Beyond The F*ck It. The spirit of going beyond where before you might have stopped.
For whatever reason, this resonated with me completely. When I finished the chapter, I closed the book, opened my laptop, and started typing what would become my first post. Three days later, I had my first post ready to publish.
The night before launch, I barely slept. I'd set it for a scheduled send - Thursday, 27th June at 6:13 AM (my lucky #13 again). There was no dramatic button-pressing moment, just the slow torture of knowing that in eight hours, my first post would launch whether I was ready or not.
At 6:13 AM exactly, "Introducing Own The Now" went live. I didn't even need to be awake for my own courage. Truth be told, I'd hit snooze- a rare occurrence - because I'd slept so badly!
I deliberately didn't look at my email for the first few hours of the day. Terrified of responses—or worse still, NO responses. But when I finally worked up the courage to check, there were nothing but messages of congratulations, encouragement, and positivity.
Twelve months later: 21 posts, 35,249 words, subscriber growth of 225%, and an 82% average open rate. But the numbers tell the smallest part of the story.
Most importantly - I’m still alive!
The ground didn't swallow me whole. My friends haven't disowned me. In fact, by virtue of being out there, I have reconnected with a number of people I had been out of touch with.
However, the most rewarding part of it all—something I could never have predicted, let alone expected - was the level of connection and openness I received in return.
From people I've known for decades and people I've just met. People responding to my stories and admissions, acknowledging my willingness to be vulnerable, my radical honesty about failures, my shame and guilt, and the bravery in talking about it all.
I've been able to connect with my parents more closely about the things I do and the feelings I've worked through about various events.
My writing has allowed me to share deeper feelings and regrets with my wife that I'd found hard to say out loud in the past. It's also given her VIP status—a distribution list of one person, receiving posts two days early to check the writing and grammar!
I've also found joy, satisfaction, and a semblance of closure in certain respects, simply through reviewing and reliving things in my mind and on paper.
The Unexpected Audience
They say write for an audience of one. For months, I thought I was writing for potential coaching clients, or people who might relate to my investing stories, or anyone navigating an unconventional career path.
But recently, I realised my true audience: my children. Not as they are now—rolling their eyes at dad's "blog thing" - but as they might be in ten or twenty years, trying to understand the choices I made, the mistakes I own, and the lessons I'm still learning.
If they want to know why I left finance, how I handled failure, or what I learned about vulnerability and courage, it's all here. Written in real-time, not polished by hindsight or selective memory.
The abyss I feared stepping into turned out to be a bridge. To deeper relationships, clearer self-understanding, and connections I never would have made by playing it safe.
Writing forced me to examine my own narrative honestly - to stop hiding behind titles or achievements and simply show up as myself, complete with contradictions and uncertainties.
The irony? The vulnerability I was so terrified to expose became my greatest strength. Not because it made me look perfect, but because it made me real.
As Benjamin Zander writes, sometimes we need to go beyond where we might normally stop. Beyond the comfortable, the safe, the well-rehearsed version of ourselves.
Twelve months ago, I stepped into what felt like an abyss. It turned out to be the beginning of everything I didn't know I needed: radical honesty, deeper connections, and the freedom to stop pretending I have it all figured out.
So for now, I'll keep going - writing for an audience of three kids who aren't ready to read it yet, building bridges one vulnerable story at a time.
