My Retreat in California + A Group Activity


Hey friends,

I spent last week in Ojai, California, spending time with some internet friends who I (mostly) met in real life for the first time. If you’re a nerd like me, you might be familiar with some of them – Tiago Forte, Marie Poulin, Jonny Miller, Khe Hy, Joe Hudson, Nick Milo, among others. We spent a wholesome weekend in Ojai Valley, kindly organised by Tiago and his wife Lauren (and their team member Victoria), as a “3-day retreat for creators who make online courses”.

We’ve had a WhatsApp group for the past few months, where we share challenges, insights, and advice – that’s been a great source for inspiration and connection, but hanging out with these guys and girls in real life was something else.

One of my favourite group activities we did over the weekend was Mini Mastermind Sessions. I’m not sure if it has a proper name, but here’s how we did it with our group of 12.

Each person gets the floor for 20 minutes. In that time, they spend the first 5 minutes giving the group context about their work / personal life, and sharing their most pressing challenge, or something they’re struggling with. Then, for the next 15 minutes, the group is allowed to do two things: (1) ask questions, or (2) share a personal experience relevant to their situation. Crucially, no one in the group is allowed to “give advice”.

This is a great format, and something I’d 100% recommend you try next time you’re with a group of wholesome friends. It’s a great way of connecting with each other, and also a brilliant way to get perspectives on your work or life challenges that you might not have considered.

The “no advice” rule is also important – (a) because we as humans are often quite resistant to ‘advice’, and (b) because advice is given from the perspective of the advice-giver, who’s unlikely to have 100% context and expertise on the situation at hand. Instead, asking questions is the ultimate hack towards helping people get clarity on their own challenges and to uncover the path forwards for themselves.

When it was my turn, I shared the following (paraphrased): “I don’t think I know what direction to take my business… I’m already playing my infinite game, in that I get to spend my time reading, writing, learning, teaching and sharing stuff on the internet, which is exactly what I’d continue to do even if I won the lottery. But I know I also have a desire for growth and to keep levelling up. But other than money, I’m not sure what ‘goals’ to set for my and my business at this point. It’s a nice place to be for sure, but I don’t know what’s next…”

As I write this, I’m cringing slightly at the thought that the “challenge” I’ve got, and that I’m admitting to the 350,000 people on this email list, is that “life is too good and therefore I don’t know what to do next”. Part of me’s worried that you’re going to roll your eyes, hit ~~, say “cry me a river”, think that I’m a Bad Person, and think “this guy needs to get real, people have real problems out there and he’s humble brag complaining that he’s living his dream life and the only problem is that he doesn’t know what’s next”… but oh well. Part of the fun in writing this weekly email is that I get to share my innermost thoughts and (occasionally even) feelings.

Anyway, part of the joy of sharing this with the group in Ojai is that at least half of the group had exactly the same challenge – they’ve made decent money from their respective businesses, they’re living lives of freedom, fun and flexibility but they’re also trying to work out what comes next. In fact, whatever the specific context, it seemed like everyone in the group felt like they were in a transition state in their lives, where they wanted to try to get clarity on which path to choose next.

Some of the fun questions that helped me get more clarity on my situation were: * What makes you feel that you need to know what happens next? * If you could do anything you wanted, go anywhere you wanted, what would you do and where would you go? * Are you working for your business, or is your business working for you? * What would it look like to step back from the day-to-day running of your business? * What’s preventing you from stepping back from the day-to-day running of your business?

After my 20 minutes in the hot seat, and thorough lots of other spontaneous conversations with the amazing people in the group, I left the weekend with a lot more clarity, and also a lot more questions than I had when we arrived. And it was an incredible experience overall.

A few months ago, I hosted a smaller, more low-budget creator retreat here in the UK. Me and a group of around 12 friends spent the weekend in a cottage in the South of England. We ran a similar Mini Mastermind format there too – that time, we split the group into teams of 4, and then each team went to a different area of the house to do their Mini Masterminds together. It was the same rules – 20 minutes each, no advice, you’re allowed to ask questions and share relevant personal experiences. And everyone went away from those group sessions feeling “whoa that was amazing, I got so much value from that”.

So next time you’re in a group setting, where the people around you are sufficiently wholesome and/or adventurous to try something like this, give it a go 🙂 I guarantee you’ll be amazed by the results. And if you do, I’d love if you can email me and let me know how it went.

Also, if anyone has other ideas for ‘group holiday / retreat structured conversational prompts’ then please do hit ~~ and let me know – it’ll give me ideas for the next time we do a retreat.

Have a great week!


PS: By complete coincidence, me and a friend are organising a retreat in September in the Alps. It’ll be aimed at 7-figure creators / bootstrapped entrepreneurs trying to move to 8-figures (with guest workshops from $10m+ founders to share their lessons). Max 15 people. Done at cost, ie: We’re not trying to make a penny of profit from it, just to get cool people together to hangout and discuss business and life, and make some new friends lol. It’s provisionally 20-25th September 2023, it’ll cost around 10k euros excluding flights but all inclusive otherwise. If you’re potentially interested, please enter your details in this Google Form and we’ll send you more info.

📚 Shortform

For the past couple of years, I’ve consumed hundreds of books using the great summaries on Shortform.

But in exciting news, they no longer just provide detailed summaries for books…

They’ve just launched a brand new browser extension which creates high-quality summaries for blogs, articles, emails, and even YouTube videos at the click of a button.

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It’s called Shortfom AI and you can learn more and download the extension here.

Plus it’s included at not extra cost and without limits for premium Shortform users.

Click this link to get a 5-day free trial, and 20% off the annual premium subscription.

Thanks to Shortform for sponsoring this issue of Sunday Snippets 🙏

🎬 My New Videos

💼 I spent $50,000 on a business coach so you don’t have to – I’ve become a big believer in getting coaches to help you improve in different areas of your life. For the last few years I’ve had a business coach (a particularly expensive type of coach) so I wanted to share the main things I’ve learned from him so you don’t have to get one.

✍️ Quote of the Week

Many times the hardest part about achieving a dream isn’t actually achieving it—it’s stepping through your fear of the unknown when you don’t have a plan. Having a teacher or boss tell you what to do makes life a lot easier. But nobody achieves a dream from the comfort of certainty.”

From The Third Door by Alex Banyan. Resurfaced using Readwise.