It’s mid- August, and high-summer which means half-empty workspaces and airport mayhem. The Great British Bunk Off has begun. We don’t shut down in the UK like the grandes vacances in France or Norway’s Fellesferie where the entire country disappears, but despite our new Mediterranean climate, most folks headed abroad.
Steven Bartlett writes Diary of a CEO but it’s a bit serious, so here’s my Diary of a Founder on holiday, tongue firmly in cheek.
Last week in July. I badly need a holiday. In my final couple of days before leaving, I complete the urgent tasks, like tidying my desk and putting a note out for the milkman. I tell my team that I trust them completely and in the same breath, that they should contact me if anything comes up, no matter how trivial. As a result, they don’t feel trusted at all. I think about setting up an out-of-office and decide not to: it’s really not a problem to check my phone occasionally. As I leave for the airport I feel a migraine coming on.
Days 1 to 3: The relax-like-hell phase. I spend the first few days like it’s work, asking Claude for places to go that are off the beaten track. As a result, I drive two hours to eat breakfast at a recommended cafe which turns out to be closed for renovation.
At lunch, I drink local wine and then snooze peacefully for two hours. Woken up by my own light snoring, I am confused by this period of unconsciousness that could have been spent relaxing. I worry I could be enjoying my leisure in even more leisurely ways. I feel very tense for someone on holiday. As a champion of the Rest Is a Strategy paradigm, I realise my mind is still running at 94% capacity.
The villa was incredible. Zero-edge infinity pool calibrated to 24°C, local organic figs, and panoramic views of the Mediterranean. I established a strict personal rule for the week: no deep work. Only high-level casual syncs. To set the boundary clearly, I updated my Slack status to a palm tree emoji and configured the auto-responder: I am currently offline prioritising holistic bandwidth restoration. If this is an emergency, please consider whether it is truly an emergency, or simply a lack of operational foresight on your part.
Days 4 to 5: The letting-go phase. Now only checking email every other day, I get a couple of WhatsApp messages and asked to join a customer call, and feel both irritated and pleased. Can’t you do it without me? You can’t do it without me! I triage messages, sorting them into things that have to be dealt with quickly and those that can wait. I realise just how much of what goes on each week a) doesn’t require me at all and b) creates no value. I start to ignore most messages; if it’s important, they will find a way to contact me. I switch on my out-of-office.
I spent the first two hours on the lounger conducting a retrospective on yesterday. I realise the snooze was a massive waste of time. Note to self: I could have drafted three thought leadership posts on LinkedIn about asynchronous culture.
The silence was loud. Uncomfortably loud. It lacked the reassuring open plan office hum of keyboard clicks. To acclimatise, I set up a makeshift HQ at the poolside drinks table. I’m not working, per se; I’m merely running a light background thread to confirm my presence.
Days 6 to 8: The delusional phase. Finally, start to relax, lie in a little longer. I don’t look at my phone quite as much. Back in the office the weekly sales meeting is happening right this minute. Fairly soon, I start to lose grip on reality; I think about moving to wherever it is I am; start trying to figure out how soon I can retire. I fantasise about working outdoors, perhaps in a donkey rescue sanctuary or doing something physical like restoring dry-stone walls.
I’ve noticed the villa’s Wi-Fi latency is around 42ms. Unacceptable; spent 45 minutes on the phone with local customer support explaining that as an enterprise customer in spirit, I require a dedicated fibre pipe. The representative, a local named Mateo, didn’t understand the concept of an SLA. I offered to acquire his ISP but he hung up. Classic legacy-system pushback.
Afterward, I meditated. I used my bio-tracking ring to measure my heart rate during a ten-minute breathwork. My HRV dropped by 12 points. I realised why: I was breathing synchronously, which is fundamentally inefficient. If I optimise my inhale-to-exhale ratio to a 1.4x velocity, I can achieve deep relaxation 30% faster.
Went to the beach. The area was completely unstructured, the density of sunbed allocation showed a total failure of lounger spatial utilisation. I drafted a memo to the local municipality on how they could monetise the beachfront better via a dynamic pricing algorithm.
My head of product, Sarah, pinged me on Slack: Hey Ian, quick question on the Q3 roadmap when you’re back. I immediately jumped onto a quick 45-minute huddle. I told her: Sarah, I’m on vacation. I am purposefully protecting my space. But while I have you, let’s jump on a quick whiteboard session.
I couldn’t whiteboard physically, so I drew wireframes in the sand with a driftwood stick while holding my phone between my ear and shoulder. A waiter came over to offer me a glass of sangria. I declined and asked if they had any cold-pressed celery juice infused with adaptogenic mushrooms. He stared at me blankly. Look, beverage delivery is fine, I told him, but have you considered implementing a QR-code-to-drone service for the loungers? The friction in your supply chain is costing you at least 15% in lost impulse sales. He walked away. People just aren’t hungry for entrepreneurial thinking.
The local supermarket was a disaster. I couldn’t find organic turmeric anywhere. I had to pivot from an ayurvedic dish to a rustic pasta recipe. I jotted down a quick pitch deck for CookPulse: an IoT-enabled pan that uses machine learning to predict when your garlic is 30 seconds away from burning. I sent the deck to my co-founder Marcus. He replied instantly: Ian you’re on vacation. Stop. Also, who owns the IP for CookPulse? We hopped on a 90-minute call to discuss IP assignment and revenue model for the kitchenware spin-off. Vacation is giving me incredible clarity.
Day 9: The motivated phase. The end of the holiday is fast approaching. Sea-kayaking gives me blisters and that the things I am best equipped to do don’t involve donkeys or dry-stone walls. I start to look at emails again. I feel motivated to return. I have seen how much time is spent on unimportant things and am determined to prioritise ruthlessly. I have some good ideas about how to improve the weekly sales meeting.
I am practicing radical presence sitting at a beach cafe with no laptop, no phone, and no smartwatch. Just me, a double espresso, and my thoughts. For the first four minutes, it was remarkable. By minute six, I began to stress-test the operational capacity of the cafe:
- The barista takes 2 minutes and 14 seconds per coffee;
- There are 12 people in line;
- The customer acquisition cost is virtually zero;
- The cafe isn’t upselling high-margin items like almond pastries or subscriptions for artisanal bread making masterclasses.
By minute ten, I was sweating. The sheer operational inefficiency was causing me physical discomfort. I stood up, walked behind the counter, and offered to act as an interim COO in exchange for a 2% equity stake in the cafe’s future franchise model. The owner, a woman named Maria, shouted at me in Spanish and pointed to the door. I respect her focus on core culture, but her refusal to scale is going to be her downfall when a venture-backed coffee startup disrupts the resort next year.
I tried to go for a swim. Swimming is great for short-impact cardiovascular exercise, but the RoI of simple laps feels low. To optimise the session, I wore my waterproof headphones and listened to an audiobook at 2.5x speed.
We booked a boat to Formentera. Total relaxation, no Wi-Fi out on the water. That was supposed to be a selling point. Without LTE coverage, I couldn’t check any comms. My heart rate soared to 140 bpm while sitting completely still. I spent the next two hours staring intensely at the horizon, waiting for a single bar of 3G to flicker on my screen. When a faint signal finally appeared near the coast, a flood of 114 notifications hit my phone. I felt a soothing rush of dopamine.
I took a deep, relaxed breath and jumped into the crystal-clear water. I stayed in for 45 seconds before realising I could use this boat trip to write a newsletter about isolation. My wife, who came on this trip with me under the condition that I put the phone down, asked me why I was breathing so heavily while typing furiously in my swim trunks. She stared at me for a long time, then went back to reading her book – a physical book, printed on dead trees, with zero search functionality or hyperlinking capability. I don’t know how she copes with that level of information bottleneck.
Farewell dinner was an eight-course fish tasting menu, each dish introduced by the chef who spent three minutes explaining the journey of the ingredients. I couldn’t help but admire his pitch. He had clear storytelling structure, strong founder-market fit (his grandfather was a fisherman), and made good eye contact.
However, the unit economics of an eight-course menu are blatantly unscalable. You’re capping your output at 40 covers a night, I told him when he came to check on our table. If you deconstruct these dishes into ready-to-heat meal kits and sell them D2C via a subscription model, you could scale your top-line revenue by 10x without increasing your kitchen footprint. He smiled politely, said Disfrute de la comida, and walked away. Why are people so resistant to innovation?
Day 10: The final day of my holiday. I am conducting my end-of-vacation Post-Mortem. Overall, the break was a successful sprint, though we missed several KPIs:
- Target Relaxation Score: 85/100
- Actual Relaxation Score: 42/100 (due to Wi-Fi latency and unstructured beach layout)
- LinkedIn Posts Drafted: 14
- New Pitch Decks Created: 2 (CookPulse and BeachSpace, a dynamic sunbed reservation protocol)
- Unnecessary Slack Huddles Initiated: 11
I feel rested, but more importantly, I feel aligned with my core thesis: Vacation is simply work carried out in a higher-temperature environment with poor WiFi. I’ve already packed my bags. My flight back isn’t for another nine hours, but I’m going to the airport early. Airport lounges have high density seating, water fountains and fast Wi-Fi. It’s the closest thing to an office environment I’ve seen all week. I’m ready to return, and start planning my next wellness break. Rest is, after all, a strategy.
Epilogue: I return to the office full of vim, looking and feeling healthier than my colleagues. I have the same conversation twenty times. How was your holiday? Wonderful. Where did you go? [Insert answer.] What did you do there? [Insert details.] I start to make up responses. Where did you go? Wakanda. What did you do? We visited the vibranium mines. Oh, I’ve always wanted to do that.
It’s nice to see people. It’s good to have a sense of purpose. You attend the weekly sales meeting and dimly recall I once had an idea for improving it. Colleagues come back from their own breaks and I ask how their holidays were. They seem so well.
Summary: When founders step away from the relentless noise of their startup, they are not pausing progress, they are optimising for it. Counterintuitively, non-stop execution often hurts early-stage ventures through tunnel vision, burnout, and diminished decision-making. Founder detachment provides distinct operational and personal benefits:
- Restored Clarity: Constant operational fire-fighting traps founders in execution mode. Time away halts cognitive overload, enabling founders more time and headspace for lateral thinking. This perspective shift often reveals non-obvious pivot strategies that urgent daily tasks obscure.
- Forced Autonomy: When a startup cannot survive a founder’s short absence, it highlights a single point of failure. Stepping back acts as a stress test, forcing leaders to delegate responsibility, document knowledge, and build resilient processes. Empowering team members to make decisions independently accelerates organisational maturity.
- Optimised Cognitive Performance: Exhaustion degrades emotional intelligence and critical decision-making. Sleep deprivation and stress directly impair the prefrontal cortex – the region of the brain required for high-stakes strategic and creative thinking. High-quality rest and relaxation restores sharpness, composure, and endurance.
- Sustained Endurance: Startups are long-term marathons. Founder burnout remains a primary, yet avoidable, cause of failure. Scheduled time off protects energy, prevents emotional fatigue, and maintains the inner drive required to lead teams through the usual volatility and turbulence.
Stepping away isn’t a sign of distraction, it’s a decision that safeguards both the leader and the venture.