I’m worried that the rise of AI makes these vital kinds of scenes less likely.

I’m worried that ChatGPT and the like have put an end to banana-assisted-attempted-suicides, and the bonding opportunities they present.

The day before the potentially perilous attempt, we had been told by a teacher that bananas contained potassium, and that at the right dose potassium was lethal. Obviously, we wanted to know how many bananas were needed for the fatal dose, and obviously when we had the answer it needed testing. As a bonus, we found out that bananas were also 0.2-0.4% alcohol, so there was a chance our tester would be drunk when they popped their clogs.

A willing subject stepped forward and arrangements were made for the next day. Fruit was purchased, word spread and eventually that lunchtime became the stuff of legend. The story of how Tom couldn’t get all 12 down and therefore lived to tell the tale has resurfaced many a time in our group of friends over the decades that have passed. 20 years later, some people are still gutted to have not been at school that day.

This was 2006. We were already internet natives. We fussed over top 8s on MySpace and it wasn’t long before we’d be spending Saturday mornings filling Facebook albums with blurry photos we’d taken on Olympus digicams of visits to suburban nightclubs. But we hadn’t yet got to the point of having the world’s knowledge in our pockets, and I’m so glad we hadn’t.

If we’d been put on to this exciting information about bananas in 2026, I assume that someone would have immediately consulted ChatGPT or searched on Google and been presented with a neat AI-powered response. They would have learned that while bananas are reasonably high in potassium, suicide by banana is impossible. Downing 12 of them was likely to lead to stomach discomfort and a sugar high, but not death. Then they would tell the group and we’d go and have some lunch and talk about something else. How utterly boring.

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In the increasingly digital years that followed our experiment, Googling it became the norm. If you needed a fact, a quick search gave you it. No need to bother reaching for a book or asking a friend. The benefits were obvious, and the behaviour became expected.

If you dared burden someone with a question that could have been answered by a search, you might be met with a friend hitting you with LMGTFY.com (short for Let Me Google That For You) and you’d suffer the humiliation of watching your query pop up on screen being typed into Google.com - just like you could have done if you weren’t so annoying and stupid.

But what if you weren’t asking because you just needed to know the answer? What if you were trying to open up a conversation because you fancied a chat?

How many tiny opportunities for connection were blunted by search engines?

With the rise of ChatGPT and its peers, it isn’t just knowledge at our fingertips and in our pockets. It’s so much more. It’s therapists infinitely more affordable, available and patient than the fleshy kind. It’s customer support that’s better than 99.9% of humans at solving people’s issues. It’s comprehension of any subject imaginable over a brief conversation with a chat interface.

Like much of the laptop-reliant population, I’ve recently found myself enthralled by Claude Code. It can do anything. I’ve found myself using it for hours every day, and I’m just so damn productive.

When my wife started working on a new business, I was excited to show how this wonder-tool could help her build her website. She jumped in and caught the bug. It really was that good.

On her second day using it, after our baby had gone to bed, my wife asked me a question. She wanted to know how you take a finished page and actually publish it live for other people to access.

“Ah - that’s the really cool bit” I said, excitedly. “You can just ask Claude to teach you how to do it.” So back she went to the terminal, conversation over. Despite knowing how to do it, I didn’t teach her. I didn’t need to. I didn’t spend the next ten minutes going back and forth showing her and answering her questions, because Claude would just be so much better at it. We didn’t speak again for another 20 minutes.

I’ve come to feel that was a missed opportunity for a tiny bit of connection, and I feel like I’m starting to notice them more and more as my peers and I use these tools and get excited by them. There’s no need to reach out to ask questions anymore, and if you do you’re likely to cheerfully be told that speaking to an AI model will give you exactly what you need.

I wonder if similar opportunities are missed when an AI teacher explains a concept to a child (in a way proven to be twice as effective as real primary school teachers), or when someone turns to Claude to talk about their feelings instead of their friends.

‘High quality’ outcomes like a beautiful new website, better comprehension of facts and MORE PRODUCTIVITY feel infinitely more achievable than ever before - but what if the outcome isn’t the only thing we need? What if the process and the opportunities for connection along the way are equally or more important?

I think we need to become more conscious of how much connection we have in our lives, and how much these incredibly useful tools may steal connection from us if we’re not careful. It feels good to talk. It feels good to help people. It even feels good to ask for help and be helped.

Bids for connection are not productive or efficient, but making them and having them be well received is key to our contentment. Conversation might not be the most effective way of transferring facts or understanding, but it often serves a deeper, more vital purpose to a rich human experience.

So I’ve made a rule to myself. No ChatGPT-ing at the pub.

Actually knowing how old Noel Edmonds is isn’t the point. The point is the half hour conversation about how old Noel Edmonds is. The point is the stupid suggestion that he was already 60-odd when he was hosting his house parties (he started at 42). The point is the shock at learning he’s now 77. The point is the tangent about how Mr Blobby must have been dreamt up by someone on acid. It’s not supposed to be a 5 second prompt-and-response.

Balance comprehension and connection. Prioritise fulfilment over facts sometimes. The point isn’t actually knowing whether downing 12 bananas will kill you. It’s having fun and being stupid with your teenage friends.

HealthStacks: AI for Health & Fitness is a show where health enthusiasts, experts, and practitioners share how they’re using AI and technology to do cool things for their health and fitness.

It’s all about short, practical episodes where real people screen share real workflows that you can steal today.

We’ve recorded 5 or 6 episodes now and we’ve released the first two into the wild. I’d love for you to check them out and subscribe on YouTube or Spotify if this sounds like your type of thing.

In episode 1, I share a cool AI tool for fact-checking health claims with scientific papers. I also share how I go about using AI to make sure that anything new I introduce to my stack fits my goals and blood results. Watch here

In episode 2, my business partner James shows how he uses a custom GPT to build the perfect supplement stack, and how it caught a couple of things that could have really harmed him in the long run.

We’ll be sharing new episodes weekly-ish, and we’ll be sharing more on a few other projects ASAP. It would mean a lot to me if you’d subscribe and give the show a go!

1. We are each responsible for our own health, and for the results we get from healthcare systems

2. We would all benefit from using the AI technology available today to build our own health sidekick

3. We should record all interactions we have with doctors/practitioners and feed them into our health sidekicks - probably the most controversial (for now) take

I’ve been navigating a chronic sinus issue for the last 4-5 years. Most days I’m running at 6/10. When it’s bad, I’m running at 3/10. I’ve felt exhausted, frustrated and lonely being sent down dead end after dead end.

I’ve driven hours for tests ordered by a new practitioner only to be told on arrival that they’re unnecessary. I’ve waited 9 months for a referral to a specialist, turned up to my first consultation with them full of hope and been told by that specialist that they’re not the right person to help. I spent £300 on a private appointment that lasted 10 minutes and ended with the doctor suggesting I try a bit of heartburn medicine (?!) and come back in a couple of months if things hadn’t improved.

The NHS is under huge pressure. It’s underfunded and under-appreciated and the excellent people within it are overworked. In an ideal world, I’d be receiving joined up care from practitioners with deep context about me, a clear view of my history, and enough time to work through all of it. Whether we like it or not, that world doesn’t currently exist for most of us.

We can pretend that’s not the case, or we can moan about it, or we can take our care into our own hands. Over the last year or so, I’ve decided on the latter option.

The most popular LLMS (Claude, Gemini and ChatGPT) all score above 90% on MedQA - a benchmark made of thousands of multiple-choice questions in the style of the US medical licensing exams that tests medical knowledge and clinical reasoning. c.60% is deemed a ‘passing’ result, with c.87% deemed a ‘human expert’ result.

I’ve set Claude, Gemini and ChatGPT up with full context on me - including medical history, symptom diaries, blood test results, data from my home, and extensive back-and-forth question and answers. They have become my guides to taking ownership of a resolution to my challenges, including my path through the NHS.

Recording my conversations with practitioners has been the final step. I now politely let doctors and specialists know that I would like to record our session for my own review (including with AI) later on. I use Granola, then paste the transcript into the LLMs afterwards. I ask for general reviews, and ask pointed questions. The conversation becomes more insight and data for the LLMs to use to help me get to the bottom of things.

For NHS doctor and hospital visits, we all have the legal right to record whether you ask or not, but it feels better asking. Recordings are easily transcribed or fed whole into an LLM with context about you to help understand what the practitioner has told you, expand on and explain any technical terms, build on their thinking, spot things that might have been missed, and suggest next steps.

This approach is working well for me. Late last year I saw a breakthrough with my own health journey when Gemini - armed with my history, latest appointment transcriptions, test results and symptom logs - spotted a potential correlation and suggested an experiment to run to confirm a potential cause of the issues.

LLMs have also helped me go into sessions with practitioners with a plan, insightful questions to ask and suggestions to make to health practitioners. Occasionally, they’ve been disappointed with the standard of care shown during appointments - and occasionally, they’ve been incorrect in their interpretations of things. They’ve been available 24/7 with deep context and no wait times.

There is pushback, of course - one ENT specialist scoffed that I was ‘another person using doctor Google’ - but faced with the alternative of going around and around without direction in a system too overwhelmed to help me solve my issues, and living life with the handbrakes on, that’s a small price to pay.

Other doctors have been far more positive - interested in the approach, or thankful for the depth of context provided. We’re aiming here for a collaboration - you, the healthcare system and AI vs the problem - and avoid conflict and confrontation.

There are pitfalls to avoid with this approach, but none are insurmountable. Don’t outsource all of your thinking. Think first, AI second, think third. Question the results you get. Use the LLMs with practitioners, not instead of them. Politely ask to record. Give as much context as possible. Use multiple LLMs.

To get started:

1. Start a new project in ChatGPT, Claude or Gemini

2. Upload anything relevant to your personal health situation that you’re comfortable sharing (check out each company’s privacy stance first). This might include test results, symptom logs, transcripts or summaries of appointments, etc.

3. Ask the LLM to interview you about your issue. Use a prompt like:

   ‘I know you are not a doctor. I want you to act as one to help me resolve a health issue i’m facing. I will also be consulting human specialists including doctors. Below is a brain dump of everything I can easily remember and consider relevant to my situation. My aim is [enter your aim - mine was ‘resolve this situation permanently within the next 3 months so that I never feel these symptoms again’]. You may be able to help me by suggesting potential diagnoses to explore with my doctor, suggesting experiments I can run at home, suggesting further testing I can undertake, or suggesting ways to reduce my symptoms. You can also suggest ways to help me outside of these.

   Begin by thinking and researching deeply and then asking me questions that will help you to understand my situation, lifestyle, history, potential causes and the journey I’ve been on with this issue so far. You may also request more data, and I will share it if I have it.

   Do not try to diagnose the issue until you feel you have enough context and information to do so. I am interested in your thoughts - even not fully formed or confident ones - but please explain your level of confidence for anything you share, and explain your thinking.

   [Brain dump of everything relevant you can think of - history, symptom descriptions, hunches you’ve had, things you know it isn’t and why, interactions with doctors so far, etc]

4. Go back and forth answering the questions that pop up. Be critical of and do deeper research on anything it suggests.

5. You can return to the health coach each time you’re preparing for an interaction with a practitioner - just explain who you’re seeing and the aim, and ask it to be as helpful as possible in your preparation.

This feels like the way things will be going forward. OpenAI and Apple are both working on huge AI for Health bets. Doctors are writing think pieces like the one below about how their role ‘has changed forever’. There are thousands of startups working on becoming your AI Health Copilot. It’ll become easier to do - but it’s already absolutely possible.

Books

2025 was a year of change and transition. I became a father and left a company i’d spent over a decade building, and I’m now looking ahead intentionally to what's next. My reading was often aimed at helping with these transitions.

I spent a few months focused on creativity and direction. First up was the theory. Art and Fear is helpful in labelling the nagging fears in our would-be creative heads and making me feel less like ‘it’s just me’, Put Your Ass Where Your Heart Wants To Be is a short, helpful jolt to JFDI and What Art Does by fast-becoming-my-hero Brian Eno is a fun and serious take on what creativity is. All are short, easy reads well worth picking up if you’re also in the market for creative motivation.

In search of inspiration, I then sought out creative people telling their stories in their own words (and voices - I listened to all 3 of these. If you know what each of their voices sound like you’ll understand).

Good Pop, Bad Pop from Jarvis Cocker and Miracle & Wonder from Paul Simon are both enchanting and inspiring, and well produced - I think i’d have missed out if I read rather than listened to either.

It feels to me like effort and trying hard are becoming cool again after years in the wilderness, and listening to Mike Skinner talk about how intentional, studious and hard working his creative process is in The Story of The Streets felt really exciting.

While firming up the direction I wanted to take early on in the year I read a few books on the subject of direction and designing your life and career. The two highlights were I Could Do Anything If Only I Knew What It Was and Designing Your Life. Both were helpful in trying to figure out where to point my attention next. TL;DR: planning is great, but go out and actually try stuff.

Seeking inspiration from founders, The Whole Story (John Mackey’s account of founding and growing Whole Foods) was the standout of the business biographies I read this year, telling a story of huge vision in a positive industry, a tonne of grit and a little regret. Little Black Stretchy Pants (on the birth of Lululemon) and Never Enough (Andrew Wilkinson’s story from Barista to Billionaire) each had interesting bits but probably not enough to recommend wholeheartedly.

Outside of creativity and business, I found Die With Zero a great reminder of what really matters in life, what doesn’t, and how that might impact decision making. A few of the anecdotes and stats stuck with me and are likely to impact how I live - for example, did you know that the average age of someone receiving an inheritance payment in the US is 60?

Things took an unexpected turn on a sunny spring day at the beach when my friend recommended the not-at-all hopeful or cheerful Nuclear War: A Scenario. The book covers a hypothetical situation in which nuclear weapons are used in today’s day and age in painstaking (and supposedly quite accurate) second-by-second detail. A really gripping and interesting book that led to some particularly sombre thinking. Can’t we all just get along?

Around the same time I found a copy of Hiroshima in a charity shop. It’s a stunning (in a very bad way) account of the aftermath of the bomb dropped in 1945. Some of the vivid scenes of the hours and days after the atrocity will stay with you forever.

Health, wellness and fitness-wise I enjoyed Scattered Minds to give some softer, more understanding tools for ADHD challenges. Both What I Talk About When I Talk About Running and Born To Run were enjoyable reads during marathon training for different reasons - with ‘What I Talk About..’ giving the warm and fuzzies and ‘Born To Run’ making a marathon feel a bit small fry by telling the story of people on the other side of the world who run 100 miles in sandals like it’s nothing.

On the ‘Holy Sh*t, I’m a Dad Now’ side of things, the Parenting Hell audiobook was funny company for 3am February efforts to get our newborn back to sleep. Your Baby, Week by Week was recommended by a bunch of Dad friends. I dutifully read each week’s chapter between nappy changes and found it pretty pragmatic advice.

Writing

Starting with some pals wrote some awesome things this year: Evgeny’s Unconditionally Human helped me think about AI, how to use it, how to worry less about it and how to build for a world where it’s ubiquitous - with a smattering of enlightenment chat. Hector's Unplugging is a gift to all of us in its transparency and authenticity and was particularly supportive for me as I navigated some health challenges of my own. I re-read (and shared with friends) Greg Dickinson’s beautiful account of his solo honeymoon multiple times.

One theme from 2025’s reading was reducing screentime/increasing real time. How to end your extremely online era from Tommy Dixon, this piece on Aeon from Bruce Hood, a Professor of Developmental Psychology and An Existential Guide To: Making Friends from The Shadowed Archive hit the spot. Sneaking in with days to spare, Derek Thompson’s 26 ideas for 2026 are thought-provoking - and some of the graphs referenced are a little unnerving.

Oliver Burkeman’s advice to Navigate by Aliveness in a May edition of his newsletter was a useful jolt that became a mantra for me, as was The Best Things in Life Don’t Make Themselves Happen from Raptitude. Both The Pathologization Pandemic and To Have Deeper Conversations, Try Being More of an Asshole are worth being provoked by. Oh, and Freya India seems to never miss. As a newly minted girl-Dad, I’m excited for her book in the new year.

Art & Music

It’s been awesome watching from the sidelines as the amazing Euan Roberts continued to make huge waves this year, collaborating with Gucci (!) and PSG (!). If you don’t know Euan’s work yet, now’s the time.

On the music front, Derek Gee’s Solid Air conversations were both heartwarming and a great source of new (to me) music. The Maccabees return was special for me, an education for my wife and frustratingly irrelevant for my friends :( . This playlist on shuffle has powered hours and hours of writing, researching and desk work.

People

In trying to spend less time on screens, there’s theoretically less time being influenced but there were some people who broke through this year. I was inspired by both Ollie Marchon and Lottie Whyte, both building seriously impressive businesses in Health & Fitness at the same time as nurturing young families and keeping themselves (very) fit. Josh Baker’s multi-hyphenated approach to life excelling as entrepreneur, DJ and athlete has been cool to follow along with. There’s a theme to some of those I was most inspired by in 2025: creative, connected, healthy entrepreneurs.

Two other pals really inspired me this year while documenting their journeys; Mike Pallett sharing the story of moving his family down to some lovely land (with lots of work to do) in beautiful East Sussex, and the HAGT project from Liam Klimek building an amazing community around skateboarding.

Best Of The Rest (Things & Misc.)

Like the rest of the world, I’m playing around with AI. (Hopefully) like most of the world, I kind of feel like i’m falling behind and kind of feel like it might all be a bit of a bad idea for the world. But here we are.

I’ve found Gemini and ChatGPT really effective as two health sidekicks with huge context on me. I’ve given them both full access to my goals, health challenges, supplement and exercise routines, environmental data, day to day, blood test results, and data from Apple Health and Oura. They’ve both been useful when making decisions on health, fitness and navigating chronic health challenges.

They’ve shined brightest when fed transcripts from conversations with doctors for second opinions. I’ll be sharing in-depth guides for a few health & fitness use cases for LLMs in the new year - subscribe if you’re interested.

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I really enjoyed using Consensus.app whenever I found myself getting excited to try a new supplement/health gadget/protocol. It’s an easy, structured way to search through and understand scientific literature. It saved me from spending money on shiny but ineffective supplements more than once this year. Example below

A fun family-friendly AI recommendation: bringing old family photos to life using Veo-3.

Away from AI, a recommendation to 10x how many of the ‘I should read that later’ articles and essays you actually read next year without using a phone or laptop screen: get a second hand Boox Tab Ultra e-reader and install Instapaper and Substack on it. Any interesting articles I see during inevitable periods of distraction get saved to Instapaper with their browser extension and all newsletters get auto-forwarded over there without showing up in my inbox.

Everything is on the Boox ready to read in bed/on the train. I still prefer the real thing for books, but I’m loving this setup for shorter reads. It took a while to land on the Boox Tab Ultra and find a cheap second hand one - but you can probably achieve the same thing with any android e-ink tablet.

Two recommendations that chipped away at unwanted screen time this year: using a Brick religiously and setting up colour filters (black and white) as a shortcut on Mac. I still feel like i’m losing the war here - it’ll continue to be a focus for 2026.

As I’m on the journey to founding my next company(s?), I rewatched YC’s How To Start a Startup series. Still feels super relevant, still motivating, still rooted in simplicity: Build Something People Want.

That’s about it. Here’s to another year of reading, connecting, building and being.

Your perfectly designed, jealously guarded morning routine is supposed to be turned upside down by the sound of your daughter - awake way earlier than planned - letting you know that she’s ready for your full attention.

It’s good that your planned afternoon of progress on the thing evaporated in favour of enjoying unexpected great weather and an opportunistic picnic on the beach.

Your workout suffered today because you stayed up later than you thought as the conversation got deeper last night? Fantastic.

A conversation with an elderly stranger at the departure gate meant you missed out on reading 10 more pages of your book? Excellent.

It’s absolutely right to prioritise giving everything to be with your friend in crisis at the expense of whatever you had planned for your very important week.

The probability that tomorrow will be less productive because you’re fully present with the people who matter tonight should be celebrated.

Our reliance on the infrastructure for virtue isn’t misplaced. The right routine will transform your life. Working on yourself works. We can all benefit from sticking to positive habits. Discipline is essential to progress… and yet.

Real life happens in the interruptions. The best that life has to offer may be enabled by the scaffolding of discipline, routine, and commitment to self-improvement and self-actualisation, but it is not found in it. A good life, as we’ve collectively known for a long time, is built on connection with others, on purpose, on meaning.

The truly nourishing, exciting, engaging, invigorating living happens with other people. It happens in shared moments laughing, crying, learning and navigating. Sometimes simply being. Even the fruits of our solo struggles taste so much sweeter shared with the people that matter.

In the excellent An Existential Guide to: Making Friends, the author writes “If you need a rule, take this one: honour the interruptions. Friendship is an interruption of yourself by the world and of the world by yourself. If nothing interrupts you, you are not living; you are a screensaver. Go be interrupted. Go be available to be changed.”

Friendship is an interruption. A beautiful interruption, and there are many more like it. Bids for attention from family and friends, unexpected opportunities, getting lost in a creative pursuit, finding flow in a hobby, serendipity.

A focus only on our own rigid, planned self-realisation at the expense of these beautiful interruptions is self-absorbed. We know by now that this is not the recipe for a happy life. Beautiful interruptions interrupt us from ourselves. They pull us out of the whirlpool of self-absorption.

Good habits and routines matter, especially if you want to live a full life. “There is no more miserable human being than one in whom nothing is habitual but indecision” writes William James. The more we turn our good intentions into habit, “the more our higher powers of mind will be set free” for the really important things in life. Those that achieve big things rarely get there by accident. Progress takes effort and discipline.

But if we want to make progress while actually living, we need to find balance. We need to use the scaffolding to allow us to live life as fully as possible, not let it rule us. The scaffolding should be strong, but not make us brittle.

We need to be thoughtful in sorting between the beautiful interruptions and the rest, and between the essential and the non-essential scaffolding.

For those of us that thrive on habit and routine, there may be ways for us to embrace the beautiful interruptions without anxiety.

We can protect the lower bounds of our habits and routines and - for the right interruptions - not be so hung up on the upper bounds. Less sleep, not no sleep. Less movement, not no movement. Less work, not no work.

We can zoom out on our timescales. We can commit to repairing any perceived damage - catching up on sleep after late nights, re-jigging workout plans for the rest of the week, make time later for working on the project.

We can be fully present for both parts of life - the important routine and the fulfilling beautiful interruptions. We can avoid souring our moment-to-moment experience of living by worrying about what we’re not doing. We can try and learn from Montaigne; “When I dance, I dance; when I sleep, I sleep”.

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To live a truly great life, presence is more important than perfection. We need to remember that the scaffolding exists only to help us live our lives to the fullest. We need to build a riverbank wide enough to let currents meander and the river of life to find its course. We can let our routines be strong, but our grip on them be light so that we are ready to answer when real life calls.

I started Sideways 6 as a naïve 24 year old with a lot of help from 3 mentors I was working for full time. There was never any master plan, and I didn’t know where it would go. I don’t think, deep down, that I believed it would go anywhere.I was just excited to try this business stuff for real.

The idea came from experience and insight working at the agency run by the 3 mentors. Companies were asking for ways to listen to ideas from their employees and the available options didn’t seem to meet their needs. I was on a one‑year placement through the New Entrepreneurs Foundation and hungrily looking for an idea to put my energy behind. This one seemed good enough to me.

Months of prototyping, and customer development followed. I reached out to hundreds of potential customers, hastily prepared a first website and built a deck to talk through the idea. Before long I had some amazing people at a well-known company interested in being our first customers. I googled ‘SaaS sales contract’, found something plausible, made a few tweaks, and sent it off. A month or so later, it was signed. We had tens of thousands of pounds in revenue overnight. I remember being ecstatic.

Other pinch‑me milestones followed; hiring our first employee, moving in to our first office, getting our first press, raising investment. It was all so exciting. This little idea was now a very real business with income and outgoings, shareholders, customers, partners and other very real, very dedicated people who had joined the team to make it all happen.

We kept growing. Not without challenges - there were several near‑death moments, years where growth was very slow, and a lot of stress along the way. But we grew. By 2022 we’d reached over 40 employees across 2 permanent offices and millions in annual recurring revenue. We were working with some of the best known companies in the world. Our product was (and is to this day) the best in the market.

What changed

But on my side, the buzz was fading. Most of my time was now spent managing people - more people bring more people problems, and almost every problem in a company is a people problem. I felt removed from the doing and felt I was less able to impact results. I’d hired a leadership team and had listened to the common startup advice that my job was to bring in the right people, give them resource, and get out of their way. I was absolutely not in Founder Mode.

The ups and downs were taking their toll. Without co-founders to turn to and with a misplaced (on a lot of reflection) feeling that crises and big challenges were mine to deal with alone, I felt isolated, lonely and stressed. Successes felt like a reprieve - maybe an opportunity to catch a quick breath, but certainly not to be celebrated. I was on high alert 24/7. Every challenge - a customer threatening to churn, a scary cashflow forecast, a regrettable resignation - felt existential to the company and often to me personally, too.

After nearly a decade working on the project and proud of where we’d got to, it felt like the right time for a new phase, a new inflection point.

In 2023 we were acquired in a deal that I think everyone was and is happy with. The company that bought us is an excellent company. A market leader with a high density of great people. Working with the CEO and leadership team was a real pleasure and I learned a lot from their leadership. Seeing our acquirer’s strengths shone a light on where we’d been making mistakes, and I think my influence on the leadership team was additive to the group, too.

Sideways 6 grew under the parent company’s influence. As always, it wasn’t a straight path and there were many ups and downs, but by my final year at the company was our best ever on almost ever measure - revenue, growth, profitability, etc. It couldn’t really have gone much better. And yet, 27 months after we were acquired and 138 months after starting the company, I left in June 2025.

Why I left

When I close my eyes and think of my highlights building Sideways 6, most of what I see are the early days. Time spent locked in meeting rooms prototyping, sending photos of wireframes for early product features to my CTO and pushing them live days later, and late nights trying to come up with new ways to find new customers. It’s the creating, the solving, the doing - often with other people just as keen as me, often in response to what felt like existential challenges that somehow felt galvanising rather than scary.

I think of a 2 hour train journey to Sheffield where I built us a new website. I think of giving a demo to an Australian company at 11pm in the bedroom of my shared flat while my girlfriend slept feet away and the elation when they ended up becoming a customer. I think of the Friday ritual in the first few years where we’d go to the pub for a pint at lunchtime and then spend the afternoon booking meetings - by far our most successful hours of the week.

While the company was now in a significantly better place than it was while any of this was happening, my own motivation and engagement had dipped for it’s absence. As a company we were much more mature, much stronger, much more secure and we had much better long-term prospects - but I missed the feelings from those earlier days.

I found myself yearning for scrappier times with higher velocity of output. I bristled at conversations with my team that involved planning quarters ahead, and I longed to be on a maker’s schedule.

I also started to feel a challenge that I didn’t know who I was without Sideways 6. I started to define my whole self as the founder and CEO of the company, and because it permeated into pretty much every second of every day, I didn’t know what I would be if I wasn’t in that role, and that was pretty scary.

As the company had evolved, I’d ushered parts of myself away for the greater good. I’d not been fully, authentically me because I felt like versions of me would lead to better results. This was starting to grate, but I didn’t see a way of bringing my whole self back this late in the game.

Finally, I was struggling with purpose. I’d always felt a strong sense of purpose growing the company. It hadn’t actually come from our mission, though our product is a net positive in the world and birthed some incredible ideas. The purpose i’d felt had always been around answering the question ‘how far can I take this?’. Each new phase - first customers, first revenue milestones, first employees, getting to acquisition - was invigorating. But the feeling had faded.

What this means for the future

It’s now a few months since I moved on, and I’ve got my mojo back. I’ve de-stressed, been fortunate to spend some amazing time with my wife and baby, and there’s been room for much introspection and learning.

I’m beginning to build again, only this time I’m aiming to be more intentional and thoughtful. I’ve set new rules for anything I work on from here on in. I’m aiming to take the best of my previous experience and avoid some of the pitfalls and challenges from last time around.

The new rules:

1. Enjoyable & Interesting; In line with my curiosities. Aligned with my values. Likely to lead to enjoyable days, weeks, and months.

2. Stay free; Able to run a great business while meaning maintaining control of the business and my day-to-day, week-to-week schedule.

3. Compounding; Even if it fails, I learn valuable things and meet valuable people for my next ventures and investments.

4. Fits the life I want to live; Allows for travel, time with family, working out, time in nature, etc.

5. Spend time with interesting people; Learning and connecting with people I admire and respect.

6. I’m a top 5% founder: Some combination of my experience, skills, interests etc gives me an advantage.

7. It’s real and pain-based: A painkiller, not a vitamin. Provable customer demand. Clearly solves a high priority pain for people/companies with money to spend on solving it.

8. AI resilient: Unlikely to be made obsolete or see major challenges by likely progress in AI. It still matters in an AI world

9. AI-first: Able to benefit from being run in an AI-first way using latest and greatest AI tools. Gets better as AI gets better

10. Now is the time: There’s some combination of technological, societal and/or consumer behaviour reasons that mean ‘the time has come’ for this idea and it probably wouldn’t have worked in the past. Potentially a ‘one chart business’

11. Makes money: At least funds [x] per month personal burn relatively quickly. This can be achieved by hitting [x] per month take‑home within one year, a clear path to [x] a month take‑home within three years, or a clear path to a [x] sale within five years.

12. It matters: I could imagine spending the next 20 years on this project, working hard for long hours when needed and not burning out. It’s not bad for the world (it doesn’t have to be saving the world) and has meaning to me and/or sparks curiosity.

13. Capital: I can get to profitability or major milestone for under [x] + 3 months of my time without external capital.

14. Team: Can be run with a lean team. I won’t need to hire ‘bodies’ to bring the idea to life. Scale doesn’t come from headcount. Potential for a great co-founding team

I’m grateful for everything over the last 12 years and indebted to everyone who helped make them such a success - and now i’m excited for everything yet to come. Onwards and upwards!

A friend recently asked for my advice on getting fitter. Over coffee, he recounted a harrowing Elizabeth Line journey back from a 5-a-side football game in deep East London wallowing in feelings of embarrassment and shame. A superstar box-to-box midfielder in his teenage years, he’d found himself feeling way off the pace of the other 30 somethings. Alien feelings of being slow, incapable and unfit were creeping in.

As a busy 35 year old Dad of two young kids he now felt himself at a crossroads - get fitter or stop showing up to the games he’d been enjoying as an opportunity to hang out with friends every few months for the last decade or so. We’ve known each other for years and he’d seen my journey broadly in the opposite direction from waddling overweight teenager to pretty active mid thirties Dad and wondered if I could help point him in the right direction.

The most important thing to getting fit: adherence

I believe adherence to regular physical activity is the most important thing to focus on to get and stay fit. It’s far more effective to optimise for actually doing some rigorous movement regularly than trying to make each session the perfectly optimal workout.

The advice I gave in the moment was to find some physical activity - football, cycling, weightlifting, walking, anything - that he actually enjoyed, and to try and do that activity on at least two to three times a week for the next month. Build momentum first, worry about optimising later.

Sound advice, I thought. Find something fun, do it regularly, success will follow. But having had a few weeks to mull this over, I’ve realized I was only half right. Enjoyment is crucial for adherence. But I’d overlooked something important about what makes physical activity genuinely enjoyable enough to stick with long-term.

Thinking about my own journey and those of my friends who had fallen in love with exercising and stuck with it for years, I realised we’re rarely ever on solo pursuits. Most of the people I know who have made exercise a habit haven’t gone it alone, especially in the early days.

Over and above finding something they enjoy, those that stick with exercising tend to find something that matches and shapes their identity. They engage in an activity that comes hand in hand with social reinforcement, structure and norms.

The runner joins parkrun. The BJJ’r rolls with a familiar crew 3 times a week. The yogi practices at the same spot every Tuesday and Thursday morning. The surrounding purpose, rituals, community and spaces are just as important to enjoyment and adherence as the activities themselves.

So I’m taking my advice one step further: the easiest way to get and stay fit is to find and join a cult.

What are fitness cults?

We’ve all seen friends get obsessed with fitness cults. We’ve seen the selfies from the F45 mirror, heard the midweek chat about Saturday morning’s run club, spotted the lycra and cycling caps pile up in wardrobes, been ambushed by shadowboxing in public places, listened to the CrossFit enthusiast drone on about beating PBs or learning new skills.

It’s easy to turn our noses up at these cults and their followers. I definitely have done in the past. But there’s two things we’re missing when we dismiss them.

Firstly, if someone gets to the point where some kind of physical activity is becoming a major part of their personality, it’s doing good things for them. Their joy can sound like zealotry to outsiders. The one liner previously reserved for vegans is rolled out for those that share the gospel of their fitness cult; ‘how do you know someone does Crossfit? They’ll tell you.’ But what if their enthusiasm is absolutely genuine, rather than boastful? They’re full of endorphins from feeling betterand they’re excited about that feeling

Secondly, strip away the darker elements of cults - the dogma, the isolation, the coercion - and what remains is a remarkably effective structure for sustaining fitness. A shared activity and purpose driven by a supportive community of invested people, backed up by cult-like features to drive enjoyment and adherence.

Rituals and events provide opportunities for the community to come together and celebrate, deepen ties and grow. The buzz on the Parkrun start line at 8:55 on Saturday morning, the pride at a martial arts belt grading, the camaraderie at the Hyrox finish line.

The cults are held together by Community Glue - buzzing WhatsApp groups, post-training pub visits and specialist online communities like Strava, Zwift and Whoop to share progress and seek inspiration. Most have major community presence on social media too, with followers sharing advice, milestones and questions.

Identity language is learned and used by cult members, solidifying that they’re a part of something as their knowledge grows - CrossFit’s WODs, AMRAPs and EMOMs, boxing’s combinations, F45 pods, LionHeart and Hollywood, running splits, yoga asanas

Every cult has its uniforms and symbols, its robes and relics to show yourself and others that you’re a part of it. In fitness they come in Lycra, gis, milestone tees, sweat-darkened boxing wraps, event patches and worn climbing chalk bags. All welcome knowing looks from fellow cult-members and cement to the holder that they belong.

All of this comes together to create an environment that is often scoffed at from the outside, but creates enjoyment, belonging and long-term adherence for those on the inside.

What we’re witnessing as we see our friend become a modern runner and don their wraparound sunglasses, research hydration vests and get addicted to Strava are rounds and rounds of identity reinforcement loops. Research has found that as people go deeper into these fitness cults, they adopt the group norms as part of their identity as someone who belongs to that group.

Psychologists call this an identity reinforcement loop: behaviour strengthens identity, which strengthens behaviour. Crucially, one of the main group norms is to regularly undertake the physical activity itself. They are now a runner, and runners run. Adherence from identity.

Finding your cult

To start benefitting from fitness cult membership, you need to find one that feels right for you. Some will give you ‘the ick’ before you’ve stepped into the studio, and that’s okay. With a little research, you should be able to find at least a few from that don’t repel you. That’s your starting point.

These cults may feel daunting to approach, but they tend to be very welcoming to potential new members. Every proud, fit cult member walked through those doors for the first time as a naïve newbie just like you. Most fitness cults have structured onboarding to get you up to speed and try-before-you-commit in an open-armed environment.

Each cult will have its initiation rituals - stepping through the ropes into the first body sparring session, the first non-wobbly warrior three, the first badge on Peloton. Initiations can feel awkward - the first ‘OM’, high-five or attempt at using the in-language might fall flat. Stick with it.

Trial and error is part of the process. The on-beat pedalling of a spin studio might seem like a fit from the comfort of your own home, but the reality of the perma-enthusiastic instructor may not work in reality. The idea of lifting heavy weights might be more attractive than the reality of callouses on your hands. Push on regardless - you’ve just not found your cult yet.

Finding a fitness cult is no different from finding your tribe in other walks of life. You’re testing languages, rituals and uniforms on for size. Some will feel right, others won’t.

Soon you will find one that works. The uniform fits, the language starts to come naturally, the journey home is one of excitement and pride rather than shame and embarrassment. Your identity starts to shift. You’ve found your cult.

It was a dark, wet lunchtime in the assembly hall at primary school. We were hiding from the rain with games, paper, pens and classmates. I’d just exerted 20 minutes of tongue-out effort on a drawing of the Eiffel Tower when Lee walked over. He saw my drawing, smiled and gleefully announced that it was crap - and that I was fat, too. Crap and fat. Two things that were clearly bad, that I clearly was, and that I clearly shouldn’t be.

Thanks to Lee, I still know - decades on - that I should not be crap and I should not be fat. When I feel I might be either, I feel bad. When I might do something that might lead to feeling that I might be either, I feel bad and don’t do it. I should not attempt things that might make me look crap. I should not risk judgement. I should not rock the boat. 7 year old Lee dropped these shoulds on me and went on his way.

Lee’s throwaway words became rules I never chose. And like most rules we inherit, they shaped me long after he forgot them.

We all carry them. Little rules that say who we should be, what we should do, how we should live. Most of us never chose them, yet they shape us all the same. Shoulds stick over time, like barnacles to a whale. They come from all around:

• Family and childhood: A sibling’s summer-holiday jab, a parent’s throwaway line about what counts as a “proper” career. Tiny remarks that still echo in the background when we speak up or hold back.

• Comparison and observation: A friend who seems endlessly social (I should get out more). A colleague with unshakable discipline (I should be more like that).

• Modern noise: A podcast declaring no alcohol is safe. A book selling the cure for some ailment I might have. Influencers influencing.

Shoulds often serve us well - improvement in health thanks to ‘I should exercise’ finally sticking. They can help you deal with challenges - ‘I should **give myself some kind of routine in the morning’ in the face of weeks or months living in a way you don’t want to.

Many shoulds are less useful though - coping patterns that outlived their usefulness. Some were once useful, but are not any more - the exercise compulsion that doesn’t allow rest days, or the routine that cannot be broken for even the most fulfilling experiences.

Most of us are walking around with more shoulds than could ever be fulfilled with the time we have. Before long, they start to contradict each other; sleep or social? Work or family? Create or hide from Lee?

These contradictions border on identity crises. Modern writers talk about one of the key parts of habit formation being identity - that habits stick when you see yourself as the type of person who would do the habit. ‘I am a runner’ vs ‘I want to run more’. Maybe shoulds sticking is a challenge of identity - of taking on too many, or of not being confident enough in one’s own - often entangled with the urge to please. Some people seem to avoid being bogged down with too many shoulds. Perhaps their confidence in their own identities serves as a useful barrier.

So what should we do with them?

What to do when you feel like carrying all these shoulds might not be serving you?

For me, it began with noticing. A subconscious should is far more dangerous than one that’s been named and interrogated. Noticing Lee’s impact on me has started to make it all seem pretty feeble. Seeing the nagging voice as a bit pathetic gave me more confidence in hoisting my head above the parapet and publishing this essay, for example.

When you feel compelled, ask: is this a want, or a should? Where did this come from? Does it even belong to me, or does it belong to someone else - your own Lee?

Soon it becomes obvious: there are more shoulds than can possibly be satisfied. You’ll never be able to appease them all, and it’s absurd to think - even subconsciously - that you could. As Karen Horney wrote in The Tyranny of Should:

What strikes us first is the same disregard for feasibility which pervades the entire drive for actualization. Many of these demands are of a kind which no human being could fulfill. They are plainly fantastic, although the person himself is not aware of it. He cannot help recognizing it, however, as soon as his expectations are exposed to the clear light of critical thinking.

Each should, once noticed, eventually demands a choice - does this should deserve to stay? Do I want it? Does it serve me?

To understand this, a sense of direction and an understanding of what you actually want is important. A 5am wakeup could be perfect for the Dad trying to get things done before the kids awake and bring their beautiful chaos. A carefree midnight cocktail with the man you may build a family with could be vital for the young woman seeking love. For either of these to be derailed by the other’s misplaced shoulds could be tragic.

Simple in theory; far harder in practice. Many of these shoulds are a little more stubborn and require something deeper to shake them off. Onto the bigger picture.

If we’re more likely to accumulate shoulds when we’re not confident in our identity and when we are operating from a position of people pleasing, then we are likely to combat them when we are confident and living our lives in a way authentic to ourselves. When we are able to trust that our deepest feelings and our intuition are a worthy guide, and that they are more likely to help us than whatever we pick up from the outside world.

When we feel that we are enough, despite all of our flaws. That outside criticism - real, like Lee’s feedback on my infant drawing, or imagined, like his criticism of anything i’ve thought about making since - isn’t relevant to us enjoying and making the most of the only life we have to live.

A life built on shoulds is borrowed. A life built on wants is one’s own.

I’ve read both. ‘Against the Odds’ – the expensive, secret one – is much more interesting. It’s a (sometimes too) unfiltered look at Dyson’s early struggle and success, told by someone with a huge chip on their shoulder who finally feels vindicated by the huge success of their invention after years of graft and failure. I think I paid £65 for it, and I think it was worth it.

Here’s the biggest thing I took from it

There might be a better way of doing it

Vacuum cleaners existed for nearly a century before Dyson’s bagless cyclone-powered DC01 hit the market. In that time, there had been very little innovation and the market leaders were entrenched. New models were released every now and then and the public bought them, but they were all based on the same basic way of doing things from the early 1900s.

As Dyson’s legend goes, he noticed a flaw in them; vacuum cleaners revolved around a disposable bag that collected the dust and other nasties from your floor, but this approach led to crappy results. After the first few minutes, the ‘suck’ on the vacuum sucked – it was clogged and weak. Inspired by cyclone technology he’d seen in another setting, he set about designing and testing a bagless vacuum cleaner that would be much better at sucking, and would suck less.

His testing showed it worked. Over thousands of prototypes, he got to a point where he had what he was sure was a better way, and he set about trying to license his technology to manufacturers. And he failed miserably

No one was interested – not the incumbents, not other electrical manufactures, no one. All he kept hearing was ‘If there was a better way to make a vacuum cleaner, Electrolux or Hoover would have done it’.

Plus – the incumbents had a nice little business going selling bags. Why would they want to go bagless?

Time and again he spoke to everyone he could think of, and none of them saw enough in the bagless cyclone vacuum cleaner to back him. In the end, he had to do it himself – and it’s fair to say it’s gone pretty well. Dyson’s company did £6.5bn in revenue in 2022.

..then why hasn’t it been done yet?

So – there are better ways out there, even if the 8 or so billion others that share this planet with you haven’t made that better way happen yet.

There’s so many reasons why the better way might not have made it ‘out there’ yet;

• It could be a problem that no-one’s spent much time on

• The incentives might not be there to make the innovation happen yet

• Incentives might exist to keep the status quo as it is

• You might have genuinely come up with a new way of doing things that makes sense that others just haven’t thought of before

• Technological advances might have made your idea possible for the first time

Dyson isn’t the only person who’s made new happen

Wheels were first added to suitcases in 1970 by Bernard Sadow. Before then, luggage was lugged. Now, you wouldn’t buy a suitcase without wheels.

Dick Fosbury’s ‘Flop’ in the pole vault competition of the 1968 olympics was the first time the world had seen someone fling themselves over the bar headfirst on their back. In this summer’s olympics, you won’t see a single person take any other approach.

Have confidence that there might be a better way

In Against the Odds, it becomes clear that Dyson is an incredibly confident person. 10 years of nos and knock-backs didn’t dent his confidence one bit.

What i’m taking away from this is a little bit more confidence in working on new things in established places, a little bit more confidence that we haven’t already got everything figured out, and a little bit more confidence that those little ideas we come up with might just have legs to them.

When I got home, I resolved to spend time digging into this feeling of disconnection, and attempting to replace it with it’s opposite. Connection to other people nourishes the deepest parts of us. What could be more important?

Now a couple of years into my intentional connection efforts and feeling closer than ever to family, new and old friends, and myself, I thought I’d share what has and hasn’t worked for me.

Wait - isn’t it a bit weird to be intentional about this stuff? Aren’t connections just supposed to happen?

Maybe, for some people. I felt a bit of shame when I first thought about improving my friendships and feelings of connection as a project to be worked on. I felt like this should all just happen, we should just be able to find our people, and the relationships should just flow, and we should just end up with rich, deep relationships that really work.

But that wasn’t happening for me, and I wanted it. So shame be damned. ‘Feel connected’ became a goal, and seeking out and nurturing nourishing relationships became a project. Maybe it’s a personality quirk of mine, maybe it’s a sign of the times, maybe it would work for anyone anywhere. It’s important, it’s not happening on it’s own, why should I feel shame about making it happen?

How to get better at connection

Intention

Making connection intentional has been the number one thing that’s moved the needle. I’m no longer leaving such an important thing to chance. I embraced becoming a midwit when it comes to connection.

The Icky Audit

Which relationships in your life nourish you? Which drain you? Who would you love to spend more time with? Which relationships help you live your values?

I could have given rough answers to these questions, but I wanted more. So I audited my relationships in a structured way - and I recommend you do, too.

Yes, it feels weird putting numbers next to names. Take solace in the fact that you are not rating people, you’re rating how you feel in relationships with people. You are trying to help yourself to understand where to spend time and energy.

List out the people in your life and the people you have a hunch you’d want in your life, and come up with a few things that matter to you in relationships. For me these were:

1. Seen - how much do they seem to see and know the real me? How authentic am I in this relationship?

2. Energised - how energising or energy-sucking is this relationship?

3. Value/goal alignment - is this relationship well aligned with how I want to live?

4. Learning/motivation - does this relationship teach or motivate me?

5. Comfort - how comfortable do I feel in this relationship?

Then put some numbers next to names. The exercise isn’t one of strict prioritisation - it’s there to help you think intentionally about the relationships in your life and the ones you’d like to be in your life. For example, I started to see that some of the relationships I was most comfortable in I also felt least seen in, or I realised I felt super energised by some people I’d not made the effort to hang out with in a long time.

What you do with this insight is up to you. I added a ‘notes’ column and wrote a quick line reflecting on the scores and giving me a ‘next step’ for the relationship.

Taking the lead

You are going to need to get comfortable taking the lead in relationships. This could mean being the first to call or text, being the one that suggests hanging out, being the host or organiser. This might feel scary or even needy, but it works.

You’ll also need to take the lead in trying to be a great connection. Relationships don’t work if you’re just trying to get something out of them. You need to show up as a great friend or family member. Full attention, sympathetic ear, helping them to feel and do all the things you want to feel and do from a great relationship - and some of the things that aren’t important to you.

You’ll also need to stop taking the lead in some places. You need to make space for nourishing relationships by spending less effort on the ones that don’t nourish. Stop trying as hard with the people that for whatever reason aren’t lighting you up in this phase of your life. Stop chasing. Let go

Armed with your insights from your audit and ready to take the lead in being a great connection, you can start to take the lead in the connection itself. Reach out, suggest, organise. Things don’t just happen.

Add structure

If you’ve not already got the ick from the audit and taking the lead, here’s a third potentially troublesome thing that hugely helps me in building and tending to connection: structure.

As someone with ADHD, structure helps me get things done and live the life long-term me wants to life, not just the life short-term me comes up with minute to minute. Building connection is something long-term me craves, so I’ve built structure around it, and it’s worked fantastically well.

Personal CRM - Clay

I’ve been using Clay for the last 6 months, and it’s been transformational. It’s a personal CRM - a tool that sets up a record for everyone you know and helps you stay connected with the people that matter. I was using Notion for this purpose but it was super manual. After an intense onboarding, Clay makes it really easy by reminding you to connect with people you’ve starred and inviting you to reflect on other relationships you have

Structuring the connection habit

Every day, my to-do list reminds me to connect. Ticking this off isn’t an exact science - calling my Mum might do it, or inviting some friends down for a weekend by the sea, or going to a gig with some of my nearest and dearest, or even responding to a tricky WhatsApp message i’ve been sitting on for a while. But it gets ticked off every day, and each time it does I know i’ve done something to nourish a relationship.

Other things that seem to help

Intention, structure and taking the lead have been the top 3 things to help me build connection, but there are a few other little tips and tricks worth sharing:

1. Hosting lets you bring people together, and remove some of the barriers to hanging out. You also get to help set the tone and structure - suggesting a hike and lunch with families rather than a lads only big night out, for example.

2. Become a card person. For the first 30 years of my life, cards were limited to Christmas and the birthdays I remembered. Now somehow I’m a card guy. Birthdays aren’t missed, ‘Thankyou’s are physical, and celebrations require stamps. They feel good to send and even better to receive.

3. If you’re thinking of someone, let them know. Spot something that brings someone to mind? Share it with them. Reminiscing about a great memory with a friend? Get in touch. Don’t make it a big thing. Build the muscle and make it a habit to create these tiny moments of connection whenever there’s an opportunity.

4. Groups can deliver huge amounts of connection ‘bang for your buck’. A group dinner or getaway (obviously) gives chances of connection with more people than a 1:1. Just make sure there’s opportunities to go deep with people.

A few words of warning

You need to feel this stuff out. Structure shouldn’t drown out spontaneity. Hosting shouldn’t stop you from travelling to see people . The point of the audit isn’t to decide to deprioritise your Mum and Dad. Make it work for you. Just realise that it’s so, so worth putting the effort in.

Trust is a key part of a healthy high-performance company of any size. All other things being equal, companies with a higher average internal trust level will outperform those with a lower level.

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There are 3 things that lead to a high average level of internal trust in the company and it’s leadership;

1. The company and leadership earning trust by being trustworthy in it’s actions and communication

2. The average trustworthiness of the actions and communication of everyone in the company

3. The innate baseline trust levels of the people in the company – whether they are default high or low trust in their nature

Assuming you are doing the right things on points 1 and 2 (this is a big assumption!), it’s critical to avoid poisoning your company by letting low trust people in. Working with low trust people really, really sucks.

High vs Low Trust People

Default High Trust people;

• Default to trusting others until given a reason not to.

• Are open and collaborative; assume positive intent.

• Focus on finding solutions rather than assigning blame.

• Are comfortable with direct and transparent communication.

• Spend a high percentage of their time on ‘the work’.

Default Low Trust (DLT) people;

• Assume others have hidden motives or bad intentions.

• Assume negative intent behind most or all actions and communication from leadership.

• Start from a defensive posture.

• Focus on finding faults rather than fixing problems.

• Engage in gossip and office politics instead of direct communication.

• Spend a high percentage of their time on everything but ‘the work’.

People can become higher or lower trust depending on their circumstances and experiences in life and in your company. You should do everything you can to earn everyone’s trust at your company by being a decent leader, being trustworthy and having your words and actions be consistent.

There are, however, a subset of people who live life from a DLT position no matter your actions. Because of past experiences, they assume bad intentions, view every interaction with suspicion and create friction.

They operate from a position of defensive self-protection over co-operation.

The Impact of Default Low Trust people on startups

DLT People deserve empathy and respect as people. They have often been through difficult experiences that made them the way they are.

Identifying DLT people

You must try to avoid hiring and working with DLT people. They’re difficult but not impossible to screen for. Key things to look for:

• Observe how they talk about experiences in past roles and companies; do they assume positive intent, or blame others?

• Do they take their ‘fair share’ of accountability?

• Do they find it difficult to hide their disdain for other people in general? I’ve always liked the quote “If everyone else is always the problem, maybe the problem isn’t everyone else.”

Much of the advice on hiring for high agency applies here. Avoid hiring those that moan about previous companies, or blame others readily.

Note: This was previously published on my non-substack blog. I’m moving everything over here (slowly - don’t worry, you won’t start drowing in emails from me) so you want to

In 6 days time, i’m running my first marathon. Over the course of a comparatively short 11 week training block, i’ve run 209.9km, completed an average of 4 weight training/HiiT/Metcon sessions, and welcomed our beautiful, exhausting firstborn into the world.

Everyone knows that the week before a marathon should be all about rest. Outside of one or two short easy runs to keep the legs loose and a potential ‘shake out’ the day before to ease the nerves, race week is all about stretching, rolling, recharging, sleeping, chilling out.

Why then, did I feel a pang of guilt today seeing others run up and down the seafront while I was out for a restful walk? Why did I feel in my bones that I should be exercising today too?

Let’s name this phenomenon Rest Day Guilt. I’m not the only one who feels it, so I thought it would be helpful to explore it.

Rest Day Guilt is a common challenge for active people. It’s the persistent feeling that you should always be active. The guilt felt when you act in accordance with Every Expert Ever and take a day to recharge and recover every now and then. More broadly, it covers feelings of not doing enough exercise, or the right exercise, or enough of the right exercise.

In it’s proper place, it can be healthy and helpful; it’s a version of Rest Day Guilt that gets you back on track after abandoning your workout plan for a week, and another that lifts you out of bed for an early morning class. At it’s worst, it’s unhelpful, anxiety-inducing, destructive.

Rest Day Guilt arises from different places for different people. For some it’s competitiveness or an overwhelming desire to achieve an athletic goal. For others it’s a byproduct of a world in which we’re encouraged to track and share everything, and where rest doesn’t feel so trackable or shareable. For many (including myself) it’s likely a deep-rooted and challenging relationship with the idea of being enough.

So how do we manage Rest Day Guilt? Might it even be possible to befriend it? To take the positives and avoid the negatives?

Firstly, we can attempt to let logic win the day. Perhaps we can try to redpill ourselves on the benefits of rest and recovery in athletic pursuits: whether you are trying to gain muscle mass, improve a Hyrox time, feel better about the glimpses of your naked body you catch in the mirror, or improve your Bench Press PB, proper rest and recovery is scientifically proven to make you more likely to achieve your goal. A binge of Huberman & Galpin (below) or Williamson & Israetel or some time spent chilling out with Hammond might be a useful prescription.

Then we could look to use some of the tools we know help whenever we’re acting against our own best interests; we can try to notice, to increase the space between stimulus and action. We can use some of the tried and tested methods of CBT to help us deal with Rest Day Guilt. Cognitive Restructuring for example can help us notice the voices telling us we’re being lazy, falling behind or not doing enough, and actively challenge them with what our better selves know to be true.

Finally, if we’re not ready to go full cold-turkey we can try to fill the rest day void with light activity that will promote recovery. We can tick our ‘work out’ box with a yoga session, half an hour with a foam roller, 10,000 steps or targeted stretching. We could also try an ‘active recovery’ session – but these sessions come with a special set of perils for those of us prone to Rest Day Guilt. Zone 2 can quickly become Zone 3 and Zone 4, and before we know it we’ve defeated the point.

Next time you’re tempted to lace your trainers up out of guilt, try to pause. Try to remember that your goal is not perpetual movement, it’s something greater that will be all the better for an intentional rest day and less self-flagellation.

Valian suggests the causes of work problems can be rooted in those anxieties, and made worse by “tending to think that even semi-productive people are anxiety-free. We tend to think that people's insides and outsides exactly correspond, and that their insides are completely consistent.” This resonated with me.

I have a work problem. I find it difficult to really work. I stay busy. Output happens, goals are met, fires are extinguished and Stuff Gets Done, but often I don’t seem to ‘work’ effectively. I’m the full-time CEO of a company I founded and we’ve been reasonably successful - so there’s been a lot of achievement, which must have come from a lot of work of sorts. But it’s often felt fragmented and stuttering, punctuated by distraction.

Focus hasn’t been my strong point. I work with a lot of different people, have many direct reports, and an unused bottle of Concerta XL on my desk from an ADHD diagnosis. Seemingly, I love to switch context, to check emails and work messaging apps, to look at my to-do list, to feel the tiny little buzz of a notification.

Except I don’t love it. I know what I really love is making progress on the big stuff. What gives me real satisfaction - and helps the company most - is real work on the things that I (and usually others too) don’t want to do. But while I might love having done this stuff and the mid-point feeling of progress, like a difficult workout, I don’t seem to love starting or sticking with it for prolonged periods of time. My approach is usually to wait until it must be done, and then to grind through it over multiple work sessions interspersed with lots of checking, context switching and easier efforts on the simpler stuff.

In Valian’s essay, she details very simple steps she took to ‘cure’ her work problem; she accepted her limitations, committed to focused work for minute periods starting at just 5 minutes a day, and “clocked in” daily with her partner for accountability. While life wasn’t suddenly perfect after implementing these strategies, she reported consistent progress in her work and has gone on to have a distinguished career.

I’ve always seen my Work Problem as a Me Problem. I am inherently flawed. Other People can sit and work for as long as they want, but my brain is broken and I cannot. Reading Learning to Work implanted another idea in my mind. Maybe it’s still my fault, but as well as being a flaw in my very being, there are potentially fixable issues with the approach I’m taking to doing The Work.

Maybe, just maybe, I could be like Virginia Valian and use a simple approach and shamefully low targets to make more progress on the meatier, needle-moving work that I’d previously found such a slog?

This month, I’ve set myself a goal so simple that I feel a tinge of shame admitting it. I’m going to work for 25 minutes a day on the Most Important Thing. That’s it.

The 3 main principles, mainly taken from Learning to Work:

1. I must do real, undistracted work for 25 continuous minutes a day.

2. It must be on The Most Important Thing.

3. To help with distraction, 3 of The Most Important Things are written on a piece of paper, and all windows that aren’t to do with it are closed on my computer for the duration of the work session.

4. I’ve told my wife to add a bit of accountability.

From an 8-hour day, I’m going to work for at least 1/16th of it. Writing those numbers down make them seem a bit ridiculous. But this is real, unadulterated work. No distractions, no checking, no context switching, no notifications. Just me, The Work and a timer. Timer goes on, and I can’t do anything except work on The Work for 25 minutes. Timer beeps at the end, and I can do whatever I want. If I’m feeling great and I’ve got gaps left in my day, I can go for a second round of 25 minutes. If i’m not or there isn’t, I don’t.

The Work must be on the ‘Most Important Thing’ because that’s usually the toughest thing that has the most impact, and often the thing I want to run away from. "Nothing is less productive than to make more efficient what should not be done at all," says Peter Drucker. "It is not enough to be busy; so are the ants. The question is: What are we busy about?" asks Thoreau.

Paper is used to list the task(s) because I’ve found that a mere glance of my (completely over-the-top complex beautiful Notion-based to-do list can become a distraction in itself.

I’ve thrown in telling my wife about the challenge for a bit of added accountability - and a nice serving of shame if I don’t see it through.

I’m 8 days in and I’ve kept it up every day so far. I’m beginning to see that small, deliberate steps can build a platform for meaningful change. Sometimes it feels awesome. On the 2nd day of the challenge, I ripped through 5 25-minute work sessions and even started entertaining thoughts that this concentration stuff is easy and wondering if I might actually be like everyone else.

On other days when my calendar is packed with meetings or I’ve woken up to a big challenge in my inbox, I’ve found it difficult to get started on a single session and ended up having to squeeze it in after I’d ideally like to finish my working day. But they’ve got done.

I’m hopeful. My initial reflections are that the method works, and that in a somewhat childish way, each day I tick off is having a very real positive impact on my self-confidence.

..and with that, I’ve completed 2 work sessions for this evening :)

• Meditations for Mortals by Oliver Burkeman

  A comforting warm embrace of a read that helps you understand your limitations and the limitations of everyone in the world, spread out over the course of 30 days to make it stick.

• Flowers for Algernon by Daniel Keyes

  My brother bought me this for Christmas and said it was the best book that he read in 2024. It's a thought-provoking tale of someone who starts life without a huge amount of intelligence but sees their situation shift multiple times. It has an ability to bring up a kind of empathy for everyone at every point of this scale and others.

• Replay by Ken Grimwood

  A second foray into sci-fi this year, a fantastical exploration of what it means to live a good life and all of the diversions you can go down that don't contribute to that goal.

• Pour Your Heart Into It by Howard Schultz

  I read a lot of founder or CEO biographies this year, looking for inspiration—and this was the one that stood out. It's an amazing story about how a big, bold vision, relentless execution, and creative problem-solving made Starbucks an enduring brand.

• Ultra-Processed People by Chris Van Tulleken

  I used to eat at least one massively highly processed protein bar a day. Since finishing this book, I’ve eaten none. A sobering look into what makes up the majority of easily available food options and the negative impacts on ourselves and our society that they bring.

• Unreasonable Hospitality by Will Guidara

  Recommended by a friend who's involved in running the world's best bar. This is an inspiring look at what happens when you go well above and beyond expectations to create amazing moments for your customers. Inspiration, stories, and rules that can be applicable to all sorts of companies.

• Watford Forever: How Graham Taylor and Elton John Saved a Football Club, a Town and Each Other by John Preston

  As a long-suffering Watford fan, I might be a little biased, but this is an entertaining and inspiring read for anyone. It tells the story of how one of the biggest rock stars in the world at the time—Elton John—bought Watford Football Club, hired Graham Taylor—our best ever manager—and they created magic together both on and off the pitch.

• How to Know a Person by David Brooks

  I don't know about you, but I'd never had an education in how to connect with people and how to build strong, deep relationships. I wanted one, and this book at least partially delivered. It's a great primer on what it means to really connect with people.

• The School of Life: An Emotional Education by The School of Life

  I'm a big fan of Alain de Botton and most things released by The School of Life. This had been on my bookshelf since attending a launch lecture with a friend, and I enjoyed getting around to it this year. It brings a lot of de Botton’s key themes and thoughts together into one easily digestible take on what it means to live a good life.

I’m addicted to screens. To checking stuff. To switching tabs. To notifications. To checking if there’s something new, despite no notifications.

I’m addicted to momentary escape from the real, the now. Even when the now isn’t the standard definition of ‘difficult’.

I don’t like it. I hate that I feel the pull when I’m speaking to my family, and I feel sad when I succumb to it and let it distract me from creating.

So i’m ending my addiction. I’m breaking free. The first step is acceptance.

I’ve done quite a few things to fight the addiction before fully accepting it. They’ve been varying levels of successful – Freedom.to, Brick and Opal help me use my phone less. Pandan guilts me into temporary breaks from my computer using data. Hundreds of journalling sessions on my ‘Whys’ give me things to move towards, as opposed to only moving against ‘The Suck’.

Now, it’s time to break free. Here’s v0.1 of the plan, to be developed as time goes on;

• Brick until 10am every weekday, all day Sunday and most of Saturday

• Opal on my computer and less than 8 hours/day laptop time

• Daily check-ins on how i’m feeling about screentime and Consumption vs Creation

I feel like i’m pretty well versed in how to crack a phone addiction, but would love to hear how people have managed to break free of bigger screens – the ‘not good’ parts of laptop usage. I’d love to just use it to do my job, live my values (including creation, learning and building relationships) and working on projects. Right now that’s being disrupted by checking, browsing and the occassional dose of brainrot.

Here goes.

It was no coincidence that both of these days were spent almost entirely at my desk on back to back calls, sitting down before the sun had fully come up and logging off after it had gone down. Aside from getting up for comfort breaks and to grab some food, I spent the whole day sat in front of my webcam, 'present' on the calls and contributing where I could. And I felt rubbish for it.

It's not new to suggest that sitting in front of a computer and staring at a screen all day isn't good for you. It is pretty new (for me at least, forced by nearly a year of fully-remote work in response to the pandemic) to be forced to do that.

Pre-pandemic, internal meetings would involve moving around in our office, walking and talking or heading to nearby coffee shops/restaurants/pubs to talk over a drink or some food. A lot of the time meetings were avoided by just having a quick chat in the office or on the way to meet a client. Now, we're having more meetings than ever and they all feel like they're exactly the same.

Walking and talking - a tiny change

Following those long, low days, I decided to try a tiny change to see if it would help. I started picking calls and meetings where it wouldn't be inappropriate to take the call audio-only and go for a walk around the local park. I might be late to the party here, but it's been an entirely positive change and one i'd recommend to anyone.

We know that walking is good for you (even better if you can walk in nature). We know sitting down all day is bad for you.We know we're being pulled into more meetings than ever (though whether we should be in all these meetings is another story). Walking and talking makes sense. For me, I've noticed a few benefits:

1. I'm more focussed during these conversations. Have you noticed people's eyes darting around and the sound of keys tapping during normal calls? It's oh-so-tempting to just reply to that email or just finish that task when you're at your desk. When you're out for a walk, those distractions don't exist

2. I feel better during the conversation.

3. I feel better during the rest of the day. Less anxious, less cranky, more peaceful

4. If I can get a big (60mins+) walk in, I feel a sense of accomplishment.

How to do it right

I think there's a bit of a stigma against not being sat down in front of your computer for video calls. This stems from worries that you won't be paying attention, or you won't be able to contribute fully to the conversation. Here's some ways to nip those worries in the bud:

1. Choose your meetings wisely. Calls where it's just you and one other person seem to work best. If you or someone else needs to share something visual, it's probably not the best time. If you're having an ultra-serious conversation or discussing a thorny issue where you think face-to-face makes sense, stick to a video call.

2. Ask permission. "I'm planning on going for a walk during our call. I'll be totally present. Would that be okay? Is there anything you need to share visually that means this won't work?".

3. Be fully present. This isn't an opportunity to do your shopping or have a chat with the other dog walkers.

4. Get your equipment sorted. You want the other person to be able to hear you fully without much distracting background noise.