Every founder I’ve ever interviewed for Millennial Masters swears by their calendar, their endless to-do lists, and the odd sticky note stuck to the side of a laptop.
It’s not just about being organised. For many, the calendar is their starting point: a living record of meetings, workouts, kids’ birthdays, and, yes, even a hard-won hour of absolutely nothing.
Some block out family time with the same energy as a board meeting. Some stack gym time right next to investor calls.
So, here are the best real-world routines, hacks, and micro-habits straight from founders who live and die by the calendar. 👇🏻
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The diary that runs the show
Inside the real calendar and to-do list routines of top founders
1️⃣ Put everything in your diary (yes, even the boring stuff)
“If it’s not in my calendar, it doesn’t get done. My week starts on a Sunday, I sit down and go through everything that I need to do that week. And I stick it in my calendar and I make sure it’s in (colour) blocks.
“If somebody needs a meeting, they can see it's a certain colour code and they know that it's a task that I could potentially move.” – William Stokes (Co-Space)
“My diary is the first thing I look at in the morning and the last thing I look at night to make sure I know what I’m doing in the morning.” – Harvey Armstrong (Prime Time)
From workouts to meetings to shopping, if it matters, it goes in the diary. That’s how top founders protect their time and their sanity.
2️⃣ Use your calendar as a living to-do list
“I use my calendar as a to-do list. Everything is blocked out in my calendar for what I’m doing, the time I’m doing it.
“Even at weekends, if I’ve got to return something to Zara, it’s in there for the hour that I’m going to go and do it.” – Jordan Stachini (Co & Co)
Turning your calendar into your action plan means nothing slips through the cracks.
3️⃣ Defend your downtime
“You can put time in your diary, as sad as that sounds, for family time. Because you can have more quality family time when it’s not just dribs and drabs. You say, right, the full day on a Saturday is this.” – Francesca McClory (FutureCloud Accounting)
Deliberate scheduling of downtime and family time is the only way many founders keep their family lives whole. Block it out or it gets lost in the churn.
4️⃣ Hard stops and boundaries (yes, really)
“To find the balance, for me personally, I put a lot of hard stops in place. So every night I put my phone on charge in a different room at 7.30pm.” – Amy Morris (Pop Up Global)
“I realised it’s OK to block off free time in the calendar as well, to set up three hours of nothingness, no calls, no nothing. I’m gonna be present and still and with my family.” – Tyler Dunagin (Turnserv)
Boundaries are built, not wished for. Physically remove distractions and enforce downtime like it’s a board meeting.
5️⃣ Time block for deep work (and protect it)
“My deep work is in the morning and my meetings are generally in the afternoon where I don’t need to be as focused on my mind.” – William Stokes (Co-Space)
“I use the first hour to two for focused work. So there’s usually no meetings before 10am.” – Stefan Husanu (Pith & Stem)
Protecting your best hours for deep work is how founders make real progress. Block it, defend it, and let everything else fit around it.
6️⃣ Prioritise, then delegate without mercy
“I’m always trying to think where can I add the most value and what are the most crucial things? What’s essential Monday, Tuesday, Wednesday, and what is a nice to have? And then I try to not do the nice to haves.” – Jack Good (Reuseabox)
“I literally have a t-shirt that hangs up in my office that says ‘It needs to be done, but I don’t need to do it,’ as a reminder of to delegate essentially.” – Will Polston (North Star Thinking)
The endless to-do list needs taming. Only your highest-value tasks get prime calendar slots, everything else gets delegated, delayed or deleted.
7️⃣ Automate and optimise with tech
“The first thing I do in the morning is update my to-do list, figure out what I’m going to do during the day.
“I pause my emails. I have Boomerang for Gmail, which enables you to pause emails coming into your inbox [in certain time windows].” – Michael Buckworth (Buckworths)
“I use WisprFlow and I hit my FN key to speak into my laptop and fill out any form, email, a WhatsApp message. I prefer to orate.
“I’m a Notion guy. I use Notion Clipper to store information and log. I call it logging your knowledge base.” – Oliver Yonchev (cocreatd)
“I use the ChatGPT desktop app and TypingMind for personal productivity, the latter allowing context-specific ‘meta prompts’ for projects.” – Thibault Louis-Lucas
The founders who get ahead are the ones who hack their day: talking instead of typing, logging everything for later, and refusing to let email or admin run their lives.
8️⃣ Track your energy, not just your time
“I wear a Whoop band and that’s really insightful. Seeing your sleep in that detail makes you really think about routine.” – Liam White (Dr. Will's)
“What I track every day is a subjective score for how well I felt I slept.” – Archie Mackintosh (TruProductive)
“I do a lot of reflection. I do a lot of journaling and I really think a lot about things. I meditate every day. I journal every day without fail. Get up early to do that because self-reflection is key.” – Gemma Price (HubGem)
Energy is the real currency. Founders who pause to check in with themselves catch problems early (burnout, distraction, fatigue) before they hit the wall. The most consistent performers stay honest with themselves, not just with their calendars.
9️⃣ Block movement and rest into your week
“I go to the gym, I go for a nice long walk, I listen to a podcast, I go for a walk at 8am every day with my husband without fail and so I really prioritise those hours in my day.” – Amy Morris (Pop Up Global)
“Every morning I go for a walk without fail pretty much, normally about an hour. I literally roll out of bed, put a hoodie on and go for a walk. I don’t look at my phone during that walk.” – Nick Telson-Sillett (Trumpet)
You can’t win if you’re always on. The most productive founders have recurring slots for movement, gym, and real recovery.
🔟 Write it down or it doesn’t exist
“You’ve got to write it down, get it out of your head, into your to-do list or into ClickUp or Asana or whatever tool you want to use, Monday or whatever. And then it’s not in your brain anymore and you can focus.” – Kieran Jones (Freethought Group)
“I have a reMarkable digital notepad. I make notes religiously for stuff. If not, then I’m using the notes on the phone. Every time I’m making notes, if there’s an action of something that needs to be done, I do a collation of my tasks.” – Tom Wallace-Smith (Astral Systems)
Whether it’s digital or on paper, founders swear by getting things out of their head and onto a list. That’s how you create headspace and headway.
Every win starts with a calendar entry
There’s no one-size-fits-all productivity hack, but there’s a clear pattern: founders treat their calendars like sacred territory.
The smartest block out everything: from deep work to family time, from rest to relentless action.
The to-do list is their ammunition, and if it’s not scheduled, it probably won’t happen.
If you want to work, rest and win like a founder, start blocking.
If your calendar doesn’t scare you a little, you’re not being honest about your ambitions.
What’s getting blocked this week?
More hacks from Millennial Masters:
For me, the real lesson when putting together this feature was to add my personal time in my calendar too, every day. I’ve already been living by my calendar, and adding tasks in it too, but blocking personal time in the diary is literally a life changer.
Love the framework. I live through my work calendar, but it's easy to get caught in the minutia. The hardest part is learning to say "no" to things.