Turning Every Win Into a Loss

Read time: 6 minutes

Hi from the freezing slopes where I've been on a daddy-daughter trip teaching Margot to ski in what can only be described as an unrelaxing, unrelenting, unforgiving life experience. But at the end of 4 days of tantrums (from both of us), we made progress and special memories.

Last week, I talked about how some of the world's mental health issues aren't even real, and they're just for performance/excuses. You can read that (and all past issues, here).

Before you read on:
If you’re serious about making 2026 one of the best years of your life, I’ve put together a short exercise that helps you reflect on where you’ve been, clarify what actually matters next, and set a calm, grounded direction for the year ahead.

It’s not motivational fluff, just a quiet, structured way to think clearly.

You can download it here → Your Best Year Ever Guide

Read an interesting tweet by @thedulab on X and wanted to expand my thoughts upon it.

He tells this story about a street trivia game. You win $1k, walk away happy. But then there's a version where you could have won $10k if you'd kept playing. You didn't. Now you're still $1k richer, but you feel like sh*t because you "lost" $9k that was never yours to begin with.

Which is a small wake-up call for me because I've been doing this my entire early-adult life without realising it.

I didn't recognise this pattern until recently.

Every time something good happened, my brain immediately jumped to how it could have been better.

Secured funding. But what if we'd negotiated harder? Hit a revenue milestone. But what if we'd launched sooner? Had a good conversation. But what if I'd said that other thing?

I was turning every win into a loss by inventing a better version that never happened.

It's not just about money or business decisions.

You go on a date. It goes well. She laughs at your jokes. You have a good time. But then you spend the entire walk home replaying moments where you could have been funnier, more confident, more interesting.

The date was good. But you've managed to feel bad about it because you compared it to a perfect version that only exists in your head.

You get a job offer. Good salary. Good team. Good role. But you spend weeks wondering if you should have negotiated harder. If you left money on the table. If you settled.

You got what you wanted. But it doesn't feel like winning because you're measuring it against what you could have gotten.

This is exhausting.

Because nothing is ever enough when you're constantly comparing it to an alternate reality where you made different choices.

You can't enjoy the $1k because you're thinking about the $10k. You can't enjoy the good date because you're thinking about the perfect date. You can't enjoy the job because you're thinking about the better offer.

Nothing gets to just be good. Everything becomes evidence of what you missed.

Why It Matters

I started paying attention to this after Heights hit a major milestone.

We'd worked for weeks on a marketing campaign. It went well. Better than expected. Revenue spiked. Team was energised. Everything we'd hoped for.

And my first thought was: "We should have done this six months ago."

Not gratitude. Not satisfaction. Just immediate regret about timing.

I caught myself doing it and realised: I'm about to ruin this moment by comparing it to a fictional better version.

If you do this enough, you stop being able to enjoy anything.

Every win becomes a reminder of what you didn't win. Every good thing becomes evidence of the better thing you missed.

You're not present for your own life because you're too busy running alternate simulations of how it could have gone.

And here's the thing: those simulations are always better. You have perfect information when you're imagining the past differently. Of course the imaginary version is better.

I started asking myself a different question when I noticed this happening.

Not "How could this have been better?" but "Is this actually good?"

Just that. Strip away the comparison. Look at what actually happened.

Did I get something I wanted? Yes or no.

Most of the time, the answer was yes. But I'd been so focused on the gap between what I got and what I could have gotten that I couldn't see it.

The Practice

This takes practice because the brain defaults to comparison.

You have to actively stop yourself and ask: What actually happened here?

Not what could have happened. Not what should have happened. What actually happened.

You won $1k. That's what happened. The $10k was never real. It was only ever a possibility. And possibilities don't count as losses.

If you're constantly creating phantom losses, you're making yourself miserable for no reason.

Your life might actually be going well. You might be getting wins. But you'll never feel like you're winning because you're measuring against an impossible standard.

Stop comparing your reality to your imagination.

Your imagination will always win. It has perfect information and no constraints.

Real life is messier. But it's also the only thing that's actually happening.

To what's actually real, Dan

P.S. Next time something good happens, just let it be good. Don't immediately jump to how it could have been better. That's the whole practice.

It helps you:

Reflect on the last 10 years, 5 years, and the past 12 months
See what’s been draining you versus what’s energised you
Get clear on what actually matters next
Set a direction for the year ahead
And create a simple mantra you can live by

If you want to give 2026 a real foundation, you can download the guide here → Your Best Year Planning Guide

And if you want the Word doc of the guide, you can get it here → Word doc of Best Year Ever Guide

(No pressure. Just a tool, use it if it feels right.)

Elon Musk

3 hrs of Elon Musk talking about space and our future on Cheeky Pint with the founder of Stripe and Dwarkesh Patel, fascinating

Listen Here

Nexus - Yuval Noah Harari

The author of Sapiens takes us through human history of ideas and our potential artificial future

Read Here

Fargo season 1

I watched this a while ago but just remembered how sensational it is

Watch Here

A 2020 study published in Emotion found that people who learned to accept their “non-ideal emotional states”, including low motivation, low energy, and neutral days, experienced significantly higher overall well-being and lower stress.

The key insight: self-acceptance amplifies emotional resilience, while self-judgment weakens it.

📌 Quick Takeaway →

Your average days aren’t failures; they’re emotional training grounds.
When you stop punishing yourself for being human, everything in your life compounds faster.

→ Link to study

In my goal to help more entrepreneurs/people who are looking to level up their careers, I've just started taking 1-1 consulting calls (only 1 a week)

Why book a call? Some of my expertise/success:

I've built 5 startups. 1 win, 1 fail, and 3 still going.
E-Commerce: Heights - with revenue over £20M a year.
Community: Foundrs, one of the UK's top founder communities
Podcasting: Leaders Media - I bootstrapped a media company that made the UK's top business podcasts including Secret Leaders, with over 50M downloads across the network.
Health/Mental Health: Overcame burnout, insomnia, depression & anxiety in pursuit of success. Hear me on Steven Bartlett's on Diary of a CEO
Angel Investing: I've invested in over 100 startups
Coached & Mentored: Certified coach & 5* mentor on Mentorpass
Personal Brand: Over 400,000 followers across social

So if you're interested in booking a session with me to talk all things business or building a personal brand, book for 30-minutes or 45-minutes. (limited spots).

Book a Call with Dan