Investing lessons from Christopher Robin and friends

Posted by Robin Powell on August 21, 2018


There’ve been mixed reviews for Disney’s Christopher Robin, but I have to say I loved it. You can apply the wit and wisdom of Winnie the Pooh to almost every aspect of life — yes, even investing. And before you start thinking I’ve finally lost it, let me explain.

The movie stars Ewan McGregor in the title role and, to give nothing away, it’s partly children’s entertainment, and partly a drama about a midlife crisis. Christopher Robin, you see, is now a middle-aged workaholic who has lost his sense of fun. Reassuringly, though, Winnie the Pooh and all his other friends from Hundred Acre Wood haven’t changed in the slightest, and if anyone can help him get him back, then they can. 

The nuances in their different personalities are fascinating, and the film left me pondering the question, What sort of investors would Pooh and the rest of the characters be?

Everyone loves Tigger. He’s big and bouncy, and he exudes confidence and enthusiasm. If he were an investor, Tigger would devour the weekend money pages and then act on all the stock tips he as soon the markets open on Monday morning.

Tigger is the competitive sort. He boasts of a range of abilities, from swimming and flying to climbing trees, that he doesn’t in truth possess. I think we can safely say that Tigger would be an active investor — perhaps even an active manager himself.

Owl would definitely be a financial pro — if not a fund manager, then perhaps an investment consultant. He keeps on telling us, after all, that owls are the wisest creatures and, as long everyone seems convinced, who’s to say it isn’t true?

Then there’s Eeyore (which my family pronounced, on the way back home, reminded them of me). He’s certainly very grumpy. Always expecting the worst, you can just imagine him as a media pundit, gloomily predicting market falls in the wake of the latest rate rise or disappointing jobs data.

Eeyore, no doubt, would be particularly depressed at the moment. Having expected the global financial crisis to last far longer than it actually did, he missed the market rebound. He also failed to reap the benefits of the longest equity market bull market in history, fleeing to less risky assets, for instance, during the Greek debt crisis, when the UK voted for Brexit and when Donald Trump was elected US President.

Piglet would have made many of the same mistakes. He’s famously timid, fragile and insecure; “it’s awfully hard to be brave,” as he likes to remind us, “when you’re such a small animal”. He’d keep most of his wealth in a piggy bank, or wherever piglets tend to store their cash.

Not one for adventure, Piglet often chooses not to leave his front door. So although he might occasionally invest in equities (as long as everyone else was) it would only be in stocks of companies close to home.

Someone who’d make a better investor would be Kanga. Protective, kind and caring, she’d be a fan of ESG funds that aim to promote social justice and the environment. She’s intelligent too, so she’d know all about the miracle of compound interest, and I’d be surprised if she wasn’t already putting money away each month for her precious Roo.

But which character would make the best investor of all? For me, it has to be Winnie the Pooh himself, for two main reasons. First, he’s extremely humble. “I am a bear of very little brain,” he admits, “and long words bother me”. In my experience, investors who know their limitations fare very much better than those who think they know more than do and who are far too easily swayed by meaningless industry jargon. I definitely have him down as an indexer.

But it’s his sheer laziness that would really work to Pooh’s advantage as an investor. “People say nothing is impossible,” he opines, “but I do nothing every day.” It’s the Tiggers of this world attract the most attention, constantly saying and doing things, while not necessarily achieving very much. For Pooh, on the other hand, life is for enjoying. Why worry about the stock market when you can choose to be blissfully oblivious, spending time with friends, eating honey and playing Poohsticks?

The biggest lesson, then, that investors can learn from Winnie the Pooh is the value of doing nothing.

Warren Buffett once said that the cornerstone of his investment style was “lethargy bordering on sloth”. I personally think Pooh puts it better: “Doing nothing leads to the very best something.”

For a bear of little brain, what a wise fellow he is.


The Evidence-Based Investor is produced by Regis Media, a boutique provider of content and social media management to financial advice firms around the world. For more information, visit our website and YouTube channel, or email Sam Willet or Christina Waider.



Robin Powell

Robin is a journalist and campaigner for positive change in global investing. He runs Regis Media, a niche provider of content marketing for financial advice firms with an evidence-based investment philosophy. He also works as a consultant to other disruptive firms in the investing sector.


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