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Sam Millan

← Writing · Life and work · 3 min read

A question I had to ask myself

She asked if I was happy.

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Sam Millan · published 2026-10-20
https://sammillan.com/writing/selected/a-question-i-had-to-ask-myself

I was telling my mum how well the coaching business was going. I’d signed two more clients and things were moving in the right direction.

She asked if I was happy.

My immediate thought was, of course. I’d just told her the business was doing well.

It took me a while to understand what she was asking. She cared about how I felt day to day, regardless of how many clients I’d signed.

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Eventually I started asking myself the same question.

Working for yourself can take over quite easily. You’re responsible for finding the work, doing it and making sure enough money comes in. You can spend a whole day working and never get paid for it. There’s no certainty about where the next invoice is coming from.

There’s always a reason to keep going.

When I stepped back and asked whether I was happier than I’d been in my corporate job, the answer was absolutely yes. A hundred times happier.

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But I also wanted to find more fun in the life I was building.

When I worked in the corporate job, training accounted for most of the time I had to myself. I’d train before work and again afterwards. I’d swim, use the sauna and steam room, and spend time recovering.

I enjoyed all of that. But between training and work, there wasn’t much room for anything else. Even sleep was squeezed.

Working for myself gave me more say over my week. I had to start using that freedom deliberately.

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I began playing pickleball with my mum twice a week. I made more time for my own training. I got to grips with my calendar and started blocking out time for myself alongside the hours I’d committed to work.

Week by week, I could see how much time I’d spent working and how much I’d kept for everything else.

I made room for chess, reading and guitar. I started taking guitar lessons with Henry.

Tuesdays became a good example of the balance I wanted. A couple of PT sessions, a guitar lesson, another session, then time to read and work on other projects. I could earn money and have a day I enjoyed.

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I’ve now set aside Fridays to go into London and see friends. A lot of my friendship groups are there, and I want seeing them to have a place in my week. I’m trying to make more regular time with my dad too.

My week has more room in it now. Training, a more consistent sleep schedule, time with friends, time with my mum. There’s still work to do, and I still have bills to pay. But I’m getting better at giving the other parts of my life some space.

I think back to that conversation with my mum. I understood the question well enough to answer immediately. Understanding what it meant for me took longer.

I was happy that the business was going well. I’m also happy when I’m playing pickleball with her.

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Both deserve time in my week.

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The life I’d keep →

The account of an ordinary week sits beside the bigger question of what I would keep after financial freedom.

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