Next week, I leave the UK for South America. I can’t wait to learn Spanish, overdose on red meat, and become Kieran Escobar. I feel most alive in a foreign country. Perhaps it’s the fear of being an outsider, but I love the discomfort. I learned so much about myself from last year’s trip to Kenya, Thailand, and South Africa. Only this time, I have no return date. There’s a whole world out there to explore (and I ain’t getting any younger). So I got rid of my flat and I’m living out of a suitcase for the foreseeable future. As you might imagine, packing was hell. As I began sifting through my wardrobe, three piles formed:
After an hour, the maybe pile was a mini-mountain. I sat by it with a sigh. I hate wasting energy on small decisions. So I scooped up the pile of renegade clothes and dumped them into a charity bag. It felt great. There’s something special about knowing the only things you own are a ‘hell yeah’. It got me thinking. The weight limit on lifeHow many ‘maybes’ do we carry around in life? How many ‘just in cases’ weigh us down because we are too afraid to say ‘no’? To commit? To change? We think there is no weight limit, but that’s a lie. Focus is finite. You can only take on so many projects, build so many relationships, and master so many skills. Each time you accept a ‘maybe’, you turn down a ‘yes’. It’s not obvious because it’s a future opportunity. But imagine if we could see which doors close because we give in to our fear. I’m sure it would terrify us into bolder action. Doing less but better‘Maybe’ might give you a good life, but not a great one. Sure, you can still get rich by being busy. But it’s a heavy load. And the more weight we carry, the less joy we feel. Ironically, we try to fix this by cramming in more. But what if we were brave enough to do less, instead? I’d bet we would get what we want from life. Maybe not immediately, but eventually. Because something magical happens when you go all in. Reality bends itself around you. You master your craft, build a great business, and become your best self. Now, I’m no saint here, Reader. For most of my life, I’ve been too much of a pussy to pick a lane. But over the past 5 years, I’ve slowly shed weight to pursue writing. It has been an uncertain but beautiful journey. Now I’m writing a book, I’ve had to say no to many opportunities. It’s scary, but you must have faith that you are saying yes to the future you want most. Where are you carrying too much weight? Lighten the load and you will fly much higher, Kieran |
On a mission to become a better writer, thinker, and entrepreneur • Ex-dentist, now building an internet business (at ~$500k/year)
Before we dive in: Get more clients using AI (free mastermind): I don’t like using AI to write. But I do like using AI to get faster results. My friend Lara Acosta is holding a 3-day live training sharing how you can grow your business using AI. It starts on the 21st. You can sign up for free at the link below (especially good if you’re interested in LinkedIn). SIGN UP TODAY Welcome to September’s Monthly Memo. If you’re new here, each month I share my income, expenses and what I’m working on...
Before we dive in: Write emails your audience loves to read (and buy from): Over the past 5 years, I’ve sent thousands of emails to grow my business. I filmed a walkthrough and built a cheatsheet sharing my 6-step process. If you want to write story-driven emails that stand out in the inbox, you can grab it here for free: WRITE QUALITY EMAILS For most of my life, I’ve wrestled with comparison. It began as a teenager. I grew up in a military boarding school: firing guns, climbing assault...
In July 2025, I was in Barcelona, journaling in a cafe nestled in a cobbled side street. I should’ve been ecstatic. I’d just made $88,000. I was writing my book and travelling in Europe. The only way life could be better was if Mila Kunis woke me every morning with a steaming cup of Yorkshire Tea. But instead, I wrestled with an issue: I didn’t like my writing. I couldn’t work out why. It’s been 5 years since I started, and I feel like I’m getting pretty good. But I couldn’t ignore the voice...