Join the mailing list!
Are You Guilty of Comparing Your Pineapples?
Have you ever looked at someone else’s finances and thought, “There’s no point for me, I’ll never have that much”? Or maybe you’ve felt that your situation is so unique, no one could possibly understand?
If so, you’re not alone, and you’re about to discover why comparing your pineapples is the fastest way to unhappiness.
You might also find out why The Donegans and people who have been on Rebel Finance School keep mentioning Pineapples. Don’t worry. Ours are the right way up!
The Origin Story: Don’t Compare Your Pineapples
On the very first Rebel Finance School course, I noticed something fascinating. People were comparing their finances, their progress, and their situations.
Comments like “There’s no point for me, I’ll never have that much” or “You don’t understand my situation” were flying around. It was clear: comparison wasn’t helping anyone. In fact, it was making people feel worse.
I wanted to communicate two key ideas:
- Don’t compare yourself to others. It rarely helps. Usually, it makes you feel sad or sets you up to try and beat someone else, either by being “better” or by putting them down. Neither leads to sustainable happiness!
- Run your own race. The only person you should compare yourself to is yourself. Track your expenses and see if they go down compared to last month. Track your net worth and see if it goes up each month.
If you were running a 100m race and stared at the other runners, you’d veer off course, trip, and fail. But if you run your own race, you have a much better chance of winning, or at least improving compared to last race.
I found a picture of someone holding a small pineapple and someone else holding a large pineapple.
I stuck it on the slide and on the night I told the group: “Don’t compare your pineapples!”
Everyone laughed, and out of everything I said on that course, this phrase stuck.
Soon, people were repeating it everywhere: “Don’t compare your pineapples!”
The Pineapple Phenomenon: How It Took Off
What started as a quirky analogy quickly became a movement. Pineapples began popping up everywhere in the Rebel community:
One day we need to figure out Pineapple merch!
We even printed pineapple cash, enough for 1 for every one of the 3000 people who came to the tour and gave it away.
Why did we print Pineapple cash? Alan thought that launching our own currency was the next obvious step!
The real reason was so every time someone looked in their wallet, they’d see the pineapple cash and think, “Maybe I should invest this money instead of spending it!”
We still meet people who have the notes in their wallets to this day.
The pineapple became a powerful reminder: your financial journey is unique, and the only comparison that matters is with your past self.
Fun fact: Pineapples used to be a sign of wealth in the 1800s. And yes, years later someone mentioned the “upside-down pineapple” meaning, but by then, our phrase had already caught on!
Why Comparison Is the Thief of Joy
Comparing yourself to others is about as useful as a chocolate teapot. Here’s why it’s time to stop the pineapple peeking and start running your own race:
- You only see the highlight reel. Social media is everyone’s personal “Best Of” album. You’re comparing your behind-the-scenes bloopers to someone else’s red carpet moments. Spoiler: they’ve got outtakes too!
- It distracts you from your goals. Eyes on your own pineapple! The more you watch what others are doing, the more likely you are to veer off course and end up in the metaphorical financial bushes.
- It can lead to resentment or envy. Instead of feeling inspired, you might find yourself muttering, “Well, it’s alright for them…” Not exactly the recipe for joy, is it?
- It’s never a fair comparison. Everyone’s starting line is different. Some people are running the 100m dash, others are in a three-legged sack race with a pineapple under each arm.
- It can sap your motivation. If you’re always measuring yourself against someone else’s progress, you might feel like giving up before you’ve even started. But remember: the only person you need to beat is yesterday’s you.
- It creates a false sense of competition. Life isn’t a zero-sum game. Someone else’s win doesn’t mean you’ve lost. There’s plenty of pineapple for everyone!
So next time you catch yourself comparing, remember: your journey is yours alone. Celebrate your own wins, laugh at your own bloopers, and keep your eyes on your own pineapple!
The only comparison that matters is with your past self.
- Track your own progress. Are you spending less than last month? Is your net worth growing? Here’s how to track your net-worth
- Celebrate your wins. Even small steps forward are worth celebrating.
- Focus on improving. You can’t control anybody else’s actions you can only work on improving your situation.
Call to Action: Run Your Own Race
Next time you catch yourself comparing your pineapples, pause. Ask yourself: “How am I doing compared to last month?” Celebrate your progress, no matter how small. And remember, the only race worth running is your own.
Peace and Pineapples
Alan & Katie
PS the next time someone in the Rebel Finance School Facebook group compares themselves unfavourably or asks “What’s with all the Pineapples, I did think I was joining that kind of group!” Please share this article with them…
2 Comments
Leave A Comment
Related Articles
Blog, Financial Independence, Save and Invest
Where do I put my money? Hello there! We wrote this article in 2025. Platform fees in the UK have changed a lot since then! Look out for an updated article coming soon.....With such a confusing array of platforms, funds and fee structures how do you ever decide where to put your money? In [...]
Blog, Donegan Update, Keeping Track
5th Jan 2026 At the end of the year, Katie and I always get excited because this means a chance to do our annual finance review! How often do you review your finances? Do you check daily, as some people do when they first find out about investing, or are you a set it [...]
Blog, RFS2025, RFS2026
After every single Rebel Finance School session in 2025, Katie and I sat down and wrote notes about what we could improve for next time. We had a lot of ideas. But here’s the thing we’ve learned the hard way over the years: our ideas are not as important as what actually works for real [...]
I think the famous Roman philosopher Seneca summed it up quite well:
“It is not the man who has too little, but the man who craves more, that is poor.”
“If you wish to make a man rich, do not add to his store of money, but subtract from his desires.”
“The greatest wealth is a poverty of desires.”
Duarte that is an awesome quote. love it. Thank you so much for sharing it with us! Peace and pineapples. Alan and Katie