It’s you.
I’ve just come back from ten days in Singapore and Thailand.
I exercised every day. I was outside every day. I ate well. I did zero work. Venture Wisely went quiet, as you probably noticed, and that was deliberate. It was the first proper switch-off I’ve had in a long time.
And somewhere between the heat and the silence, an old belief of mine came back into focus. One I hold more strongly every year I’m alive.
We spend our lives learning to manage things.
We learn to manage companies. Teams. Money. Time. Projects. Boards. Investors. There are courses for all of it. Books for all of it. Entire industries built on teaching you to manage everything around you.
And almost nothing on the one thing that decides how all of it goes.
The most important thing you must learn to manage is yourself.
Your mind. The interaction between your mind and your body. Your ambitions professionally. Your desires and wants personally. Becoming deeply connected, on a 360 basis, to what fuels your life and your energy over a very long period of time.
Not for a quarter. Not for a fundraise. For decades.
The Japanese have a word that circles this idea: ikigai. Your reason for getting up in the morning. The place where what you love, what you’re good at, and what the world needs from you overlap. I borrowed from that concept for years before I knew it had a name.
Everything else you will ever manage runs through you first.
Your judgement on a hard day. Your energy in month nine of a raise. Your patience with the person who deserves it. You are the operating system. Every application inherits your bugs.
Manage yourself badly and it doesn’t matter how well you manage everything else.
Here’s how I learned that.
One Thing Is Not Enough
I spent my early twenties a million percent focused on one thing.
Building, growing and selling ContentCal.
I had relationships. I had a huge social group. I made amazing connections. I even managed some travel. From the outside, a full life.
But everything orbited one massive achievement. One sun, and a lot of small planets.
And the win came. We sold ContentCal to Adobe, a Nasdaq-listed US market leader in its space. There was no better company to have bought it, no better place for it to live on. The biggest thing I ever wanted from my business career, done.
You’d think that’s the end of the lesson. It’s where the lesson starts.
Because the older I get, now in my mid-to-late thirties, the clearer this becomes: you cannot have one thing you focus on. If you do, the rest of the scaffolding of your life will eventually come crashing down. The win doesn’t prevent the collapse. Sometimes the win is what reveals it.
A single pillar can hold enormous weight. It cannot hold a life.
So managing yourself is bigger than managing your ambition. Ambition is one room in the house. You have to run the whole building.
Which raises the obvious question. Where do you start?
You Cannot Manage What You Haven’t Mapped
You start with foundations.
Get really into the weeds of who you are. Where you’ve come from. What motivates you and what drives you. What has shaped how you think, externally and internally, from childhood to today.
Most people never do this properly. They inherit a picture of themselves somewhere in their early twenties and run on it for decades without a service. Then they wonder why the same patterns keep producing the same problems.
You would never run a company on data that old. People run their entire lives on it.
The good news is that mapping yourself doesn’t require a mountain retreat. Some of the most useful work here is almost embarrassingly accessible:
16Personalities. A Myers-Briggs style test. Take it with a pinch of salt, as with anything of this kind, but it’s a genuinely useful mirror. You’ll recognise yourself on the page, and you’ll recognise things you’d never quite said out loud.
A Strengths Profile. More work-focused, and for me, more valuable. It splits your abilities three ways: what you’re good at that gives you energy, what you’re good at that drains you, and what you avoid entirely. That middle category is the dangerous one. Being good at something is not the same as being fuelled by it, and careers quietly die in that gap.
A Johari window, if you have more time in the game. It maps what you know about yourself against what others see in you. The gaps between those two pictures are always where the interesting information lives.
None of these tools give you the answer. They give you a guide. And once you have the guide, you can stop drifting through your life and start actually attacking it.
I organise mine into three blocks. Professional. Personal. Physical & Spiritual.
Professional: Know What You’re Good At, Know What You Need
You only learn what you’re exceptional at by trying things. Many things, over many years. There is no shortcut, and anyone selling you one is lying.
But over time, patterns emerge. And when they do, your job is to get brutally clear on them and then optimise your entire career around them.
Here’s what a decade and a half of pattern-spotting has taught me about myself.
I’m good at big-picture thinking. Looking into the future and seeing just around the corner, the things we’ll need before they’re visible in the day or the week. I’m good at reading macro trends and sensing where opportunities are forming. I’m good at meeting people and being completely direct about my motivations, what I’m driving at, what I’m trying to achieve, and then communicating that outwardly, to investors, to prospects, to team members, and setting a vision for all of us to go after.
I have good interpersonal skills, though some people may call me too casual. I believe in being open and informal, in bringing people on a journey with me at the same level rather than through strict hierarchy and process. That’s a choice, and I’ve made it deliberately.
Now here’s the part most people skip.
Knowing your strengths is half the exercise.
Knowing what you need around you is the other half.
For me, it’s structure. I work hard every single week at protecting my time, and I’m getting better at it as I get older. I also know that most people prefer more structure in their working lives than I naturally provide. So in every business I’ve ever run, one of my first serious moves is hiring an operator. Someone who runs the machine while I run at the horizon. I had one at my first agency. I had one at ContentCal. I will have one in any business I’m ever involved in, for the rest of my career.
That’s not a staffing decision. That’s self-knowledge on how to get the best out of me.
Your version will be different. Maybe you’re the operator, and what you need is someone who sells the dream. The specifics don’t matter. What matters is that you’ve done the work to know, because a team built around an inaccurate picture of the founder is a team built on sand.
One more thing on the professional block, and I’ll be honest about it because honesty is the point of this essay.
I’m in a unique position. I’ve achieved the biggest thing I ever wanted in my business career. A very large part of my professional journey, as I see it, is complete, and everything from here is a bonus, or part of the journey onwards.
There’s a phrase I’ll borrow from Dwayne Johnson: ‘Once you’ve climbed your mountain, if you’re ambitious, you’ve got to figure out the other mountains you can build and climb with other people.’
That is exactly where my focus sits at this point in my career. Not climbing the same mountain again. Building new ones, and climbing them with other people.
Rhythm Is a Design Problem
There’s a second piece to the professional block that almost nobody treats seriously enough.
Your rhythm.
What does your ideal day look like? Your ideal week? Your ideal month? Not your current ones. The versions where you do your best work.
Most people have never asked. They let the calendar happen to them, then wonder why they’re exhausted and unproductive at the same time. Busy and behind. The worst combination there is.
I’ve only recently got to a place where I can properly engineer this, and I recognise that’s a luxury not everyone has. But whatever your constraints, there is more design space in your week than you think, and every bit of it compounds.
Here’s what mine looks like.
I need large amounts of thinking space, protected blocks where nothing is scheduled and my brain can range. I need separate blocks for pure action: emails, outbound, meetings, execution. And I’ve learned something specific about how I batch: I’d rather be back-to-back for three straight days and then have two quieter ones than have five half-busy days. A morning of meetings followed by a hollow afternoon suits me terribly. Give me density, then give me space.
Your pattern will be different. That’s the entire point. Rhythm isn’t a best practice you copy. It’s a personal specification you discover, then defend.
And you will have to defend it. Every week. The world is a machine for filling your calendar with other people’s priorities. Protecting your rhythm is not admin. It’s one of the highest-leverage acts of self-management there is.
Do the Digging. Then Put Down the Shovel.
Now the personal block, which is where this essay gets closer to the bone.
Managing yourself personally means understanding what truly motivates you in life. What makes you content. What gives you energy and what takes it. And underneath all of that, it means having a healthy mind.
Let me say something plainly here. I don’t buy the idea that mental health is a negative concept.
I think the phrase has probably been overused in the last five years, stretched across things it was never meant to cover. But the underlying truth stands, and it’s not a soft truth. It’s a structural one. A healthy mind is one of the most important assets you will ever build, because everything else in your life runs on top of it.
So do the work. Properly. Understand your component parts and why they exist:
What triggers you?
What makes you emotional?
What makes you frustrated?
What makes you happy, and what makes you sad?
And where did each of those come from? Your upbringing? Your childhood? Your adult life?
These aren’t journal prompts for a rainy Sunday. They’re the source code of your reactions, and until you’ve read it, your reactions are running you.
I’ve had over two years of personal therapy, which I’m completely happy sharing. It helped me understand my life, my journey, who I am and why I am the way I am. I’ve had coaching, both professional and personal. I’ve had mentors. All of it fed the same thing: introspection. And introspection, for me, has been massive. Some of the most valuable hours of my life have been spent in a chair, talking, digging.
But here’s the part of this section that matters most, and it’s the part almost nobody says.
At some point, you have to stop digging.
There is no such thing as perfection. There is no final insight after which you’re complete. What there is, if you do the work honestly, is equilibrium.
A point where you broadly understand your machinery, your history, your patterns.
And past that point, introspection flips. It stops being growth and becomes hiding. Analysis becomes the thing you do instead of living. You can spend years excavating yourself and call it progress while your actual life sits in the waiting room.
When you hit equilibrium, force your life into action.
What do you want to do? What do you want to achieve? Set deadlines. Set goals. Set ambitions. Set dreams. Write them down and go after them with the same seriousness you brought to the digging.
The introspection was never the destination. It was the survey work before the build.
Create Friction
Which brings me to a philosophy I hold strongly, and one that cuts against a lot of modern advice.
I don’t believe in living a life of “I’ll just take every day as it comes.”
Being present is extremely important. We all need days for relaxing and recharging the batteries, and I believe in those completely. I’ve just taken ten of them in a row, and they were the point of the trip.
But be honest about the maths. If we all just lived every day as it came, realistically, nothing would happen. Nobody would build anything. Nobody would change anything. Presence is a beautiful state, which we all need at times, but a terrible strategy.
Everything you want sits on the other side of friction.
If you want a family, if you want kids, if you want to travel, if you want anything real, you’re going to have to create some. The work that makes the money. The 6am alarm that fits the exercise in before the day starts. The hard conversation you’d rather not have. The discomfort you introduce on purpose, because growth doesn’t volunteer.
Friction is one of the most important things you can add to your life, and you have to add it. It doesn’t arrive on its own.
And sometimes, even with all the friction in the world, the life you planned doesn’t arrive on schedule anyway.
I wanted a family and kids by this stage of my life. I don’t have that yet. I’m okay with it, but I want to be precise about what “okay” means, because it didn’t come free. It’s something I’ve had to learn through rather than around. The plan and the life won’t always match, and managing yourself includes managing that gap. Without bitterness, and without pretending the gap isn’t there.
For years I had “Memento Mori” as my phone background. Remember you will die. It sounds dark. It’s the opposite. It was a small Stoic tap on the shoulder, dozens of times a day: time is finite, the clock is running, get after your life the best way you can. We only live once. I believe that with everything I have, and I try to act like it.
The Body Carries the Mind
The third block. Physical and spiritual.
I’ve become very passionate about exercise, about time outside, about eating well.
Partly for the obvious reasons.
Mostly because of what I’ve noticed about the relationship between my body and my brain. They are one system wearing two names. Train one and the other improves. Neglect one and the other pays.
I find the whole area fascinating, including the study of happiness itself. What actually makes people happy? What makes them content? Because those are different questions, and the difference took me years to see.
Happiness is a visitor. It spikes and fades, and chasing the spike is a treadmill.
Contentment can live with you. It’s quieter, steadier, and far more valuable. I’ve come to believe the baseline of a well-managed life is contentment, with happiness arriving on top of it as a bonus rather than being hunted as the goal.
But hold onto one thing alongside the contentment, and guard it fiercely: hunger.
That feeling of waking up and thinking, I love my day. I’m looking forward to my week. The pull toward the next thing.
Contentment without hunger drifts into sleep. Hunger without contentment burns you down. The art of managing yourself, maybe the whole art, is holding both at once.
Let’s Go Q4
One last thought, on timing, because I’m writing this on the 1st September and the timing is the reason.
I think September to December is one of the most important seasons of the year. July and August run quiet for work.
Then September arrives and the whole world switches back on at once.
That makes September through November a brilliant three-month window to achieve a lot, professionally and personally, and to have fun doing it. In the UK you then run into Christmas, which gives the entire stretch a natural finish line, and then a reflection point before the new year begins.
Three months. A clear runway. A visible end.
If everything in this essay is the theory, this quarter is the practice. You’ve mapped yourself, or you’re about to. You know your blocks. You know your rhythm, or you’re going to design it. You know where you need friction, and where you need rest.
I’m back from my break with the batteries full. Regular publishing resumes from here.
I hope you had a good summer.
Now LFG, Q4.