Week 1 of 12  ·  ~1,160 words  ·  ~5 min read

Why I'm writing this on a soggy Sunday

I'm writing this from a typical Scottish day in May — rain and hailstones. One of those grey days when you really can't be arsed moving. I watched the streaks of rain running down the window and while studying their paths It reminded me of the long-term portfolio losers I've held over the years. And my inability to sell them when I had the multiple chances.

A thought hit me. I've got a family of five to provide for now. And I've held onto losers, multiple times, because I've never really had a defensive strategy.

How many times have I lost six figures? Enough that I've gone numb to it.

Writing it down might be the only way to make a paper loss feel like a real one again. Make it mean something.

And yes balanced out, I've made more than I've lost. But that's not the point. The point is that almost no one is willing to talk openly about their strategy, or their losses. So I'm going to try over the coming months.

So why now?

Because I can feel it building again, the upcoming losses, I just can’t put a figure on when, and just can’t put a foot into defence.

It’s 2026 and I am on the AI train — riding the infrastructure build-out — and the old feeling is back. The one that says this time is different. So before I find out whether it is, I want to look back at the train crashes I've been on before.

2010. My first foray. Faroe Islands drilling companies — the Aberdeen way into the stock market. Saw first hand the heard mentality, but did not learn first hand.

2011. Began a new overseas job, rotating in and out of the UK – 6% of salary on pension automation.

2012-2014. Built cash reserves. Bought a first home.

2014. First son born. Finally, some common sense arriving, I opened a JISA, picked VUSA — the S&P 500 — and set £100 a month on automation.

2017. Second son. Same JISA, same VUSA, same £100. And then — crypto. Wow. Screenshots on Screenshots.

2018. Cryptopia collapsed. Crypto bridge collapsed, Prices collapsed. As did my account balances – No screenshots now!

2019. Lived in Singapore, Daughter born. Same JISA, same VUSA, same £100.

Mentality - feeling sorry for myself about the collapse.

2020. Something changed. I started recording my accounts monthly. Just writing the numbers down. That single habit drove more returns than every clever trade I'd made in a decade.

2021. SPAC mania. US stocks. Risk back on. NFTs (Deary Me)

2022. (November) I sent a screenshot to a friend  — peak portfolio, peak hubris. The market promptly tanked. You're welcome.

2023. Chasing losses, but this time with a plan. Kept buying.

2023. PLTR (Sold to early)

2024. COIN (Held to Long)

2025. AMD & TSLA (Still on the Roller Coasters)

2026. NOW (Agentic AI Control Tower)

Now look at the other line. The boring one. Three JISAs. Three kids. Same ticker, same amount, never touched. Through collapses, through SPACs, through the screenshots, through every conviction trade I've ever talked myself into — the automated parts of the pensions and children’s portfolios have rarely put a foot wrong, So why continue to trade, why look for new tools, why shoot for the big wins, that’s what I am here to write about on Sundays!

So why every Sunday?

Honestly? Partly to follow on from those political talk shows everyone half-watches in the morning. Partly because the football season's just finishing and I need something to do until fantasy football starts back up.

But really, it's this. I'm writing for the other 30-to-50-year-olds who want just enough information to kick-start a new habit on a Monday — or just enough of an enjoyable read to come back next Sunday for the next bite. Eventually the Monday habit may stick.

Like a lot of us, I spend more time on a Sunday evening on X than I should. And what I notice is this — UK ISA investing is badly underserved. There are plenty of ambitious people out there looking for advice, a sounding board, consistent commentary. What they get instead is gurus pushing the dream or doomers pushing the despair.

Let the BBC do the doom. I’m here for the middle.

On X everyone's either right, or quiet, if you stand outside a revolving door long enough, every angle will get its time in the sun at some point.

With this I am trying to be neither. Not right, not wrong — just consistent. I'm someone 17 years in, still figuring it out, willing to show the working.

If that's the kind of Sunday read you want — stick around.

If you came for hot stock tips or a guaranteed path to early retirement, this isn't it. If I could I would. But I can't, so I won't.

So how do I hook you into turning up next Sunday?

Consistency, I think. Same time, same place, same length. One Sunday read, ~1,000 words, one opinion. No 5,000-word essays, no daily emails clogging your inbox.

I've committed to 12 weeks. This is week one. Eleven more to go. By the time we've travelled through this series, you'll have a clear picture of how I think about money, economics, UK tools for investments, what I've learned, what I'm still learning, and what I'm planning to move into next.

If I miss a Sunday, call me out, everyone could do with someone holding them accountable.

One thing before I sign off for Sunday supper

Seventeen years sounds like I should be close to professional in this game, but  I'm not. I'm an amateur. I make mistakes — some big, some small, the same ones the pros make but the difference is, they get paid for the privilege, and any mistakes are with other people's money. Not yours. And it hurts more when it's your own.So nothing here is advice. It's a Sunday read. Take what's useful, ignore what's not.

See you next Sunday? Perhaps…

So… if you've managed to stay off the memes for the 5 minutes it took to read this, maybe you'll make it back next week.

But like me, you'll probably need a reminder.

Two ways to get one. Follow @compound_coach_ on X and I'll nudge you on Sunday morning. Or let your phone autofill your email in the box below and I'll land in your inbox instead.

Either works. Both is better.

Next Sunday's plan: a look at what Rachael from Accounts is doing to nudge you into those S&S ISAs.

Let's talk soon,

Matt

TheCompoundCoach