100 newsletters in, here's what I've learned
15 things I wish I knew when I started writing online.
Today is my 100th post here on Substack.
That’s 100 weeks of trying to lasso unique ideas from the depths of my consciousness before they slip away never to be seen again. 100 weeks of exploring, discovering and figuring out what I’m doing while I’m doing it. 100 weeks of being vulnerable and exposing the messy beginning and middle. 100 weeks of writing one day at a time. 100 weeks of incrementally realising, essay after essay, that I am, in fact, a Writer.
When I made the decision to start this newsletter back in September 2023 I told myself that I’d commit to 100 posts before deciding what to do next. It was my first big experiment, and I hypothesised that I’d need ~2 years of full blown commitment before getting a true read on whether I could find idea-market fit, if writing was going to lead anywhere meaningful and whether, after 100 weeks, I still felt lit from within. August 15th, 2025 was earmarked as D-day. My go/no-go date. The moment I decided whether to continue or kill.
I’m now sitting on the other side of that intention and if I’m honest, I can’t quite believe I’ve made it this far. Publishing week after week has been both the easiest thing I’ve ever tried and the hardest thing I’ve ever done. The most torturous and most joyful. It’s required the biggest sacrifices while delivering the most out-of-this-world gains. And as I sit here reflecting on the journey thus far I thought I’d share a few things I’ve learned along the way:
Some days you have to force it. You have to shove the self sabotage and doubt to the curb. You have to violently pummel your way past procrastination. You have to cling onto the big picture with every ounce of strength you have to overcome the intense daily desire to back out.
Boring ideas have a role. Terrible prose has its place. Every suffering-filled draft before nailing the final piece serves a purpose. Authentic, dazzling creativity only exists because of the inevitable stretches of agony and monotony that precede it.
The internet is forever and once you put something out there it can never be recanted. Think deeply before writing about your darkest hour, your worst experience or your most recent trauma. Not everything is meant to be shared.
Thinking and learning in public is exposing but expansive. The best ideas are developed in full view, in real time.
Release yourself from the paralysing pressure to perform. Your writing doesn’t need to be the best in the world, it just needs to be the best you have in a given moment.
Follow your intention, not your mood.
The concept of linear is a human-made invention. Confidence fluctuates. Creativity comes in spurts. Growth stalls and then picks up. Careers are multidirectional. Business is full of ups, downs and arounds. Life is messy and wobbles are normal.
You get good by being ordinary for an extraordinary length of time.
Don’t fall victim to convenience by letting AI smooth out your uniqueness. Your quips, qualms, tricks and charms are what make you interesting. Bring these forward in every piece of work you create.
Momentum is created, not stumbled upon.
Everything will change. Your ideas, your writing style, your bio, your positioning, your readership, your confidence, your topics, your voice, all of it. Don’t stress about this fluidity so much and try not to let perceived external expectations fool you into thinking that if you’re trying new stuff you're “doing it wrong”. Things naturally evolve, as they should.
Discomfort is a love letter to your future self.
Don’t spend all your time and energy trying to hack the system and get cheap attention. Spend it trying to create the most brilliant body of work possible, so that people don’t have any choice but to notice you.
Bravery feels like anxiety. Courage feels like fear. Fulfilling your destiny feels like sheer terror.
The best tests with the clearest results run over an annoyingly long period of time.
So here I am, 100 weeks later, staring at the outcome of my own experiment. The data is in. The analysis has taken place. The results are decided.
So what’s the final verdict, I hear you ask?
Go or no go? Kill this Substack or continue?
You’ll have to wait until next week to find out.
I’ve been super unwell this week so there’s no VO or chit-chat today. Thanks for understanding x
🫶🏼 When you’re ready, here are three ways I can help:
Spin Up A Mini Offer Playbook: steal my process for designing, launching and testing a new income stream in under a day.
The Portfolio Career Operating System: a fully fledged system for people who do multiple things and want to do them well.
Portfolio Career Mentoring: 1-1 sessions to help you get started and build a career that sits at the intersection of freedom, creative fulfilment, meaning and money.
❤️🔥 Subscribe for more ideas and frameworks…
…to help you build a financially lucrative and creatively fulfilling portfolio career and life.
2, 6, 10, and 12 are heavy on my spirit. Congrats on 100 posts!
appreciate reading this as I just hit publish on my first post!