Unwritten Struggle?

A quiet tension in investing that I am curious if anyone else experiences.

On one hand, the rational side of me knows exactly what to do. The evidence is overwhelming: buy a globally diversified ETF, tilt toward profitable companies, keep costs low, and let time do the heavy lifting. A simple, factor-aware portfolio focused on profitability across the global market would probably do the job just fine.

Honestly… it’s hard to argue with that logic.

But then there’s the other side of investing.

The side where you come across companies that you genuinely admire. Companies with exceptional leadership. Companies building something meaningful. Companies that make you think, this is the future.

Sometimes it’s a management team you deeply respect.
Sometimes it’s a business that clearly improves people’s lives.
And sometimes the company is just so damn cool you can’t help yourself.

Rocket Lab $RKLB building rockets and launching satellites.
Bloom Energy $BE working on cleaner energy infrastructure.
Innovative businesses solving real problems.

At that point the spreadsheet logic starts losing the battle.

You know the academic answer: keep it simple, diversify, don’t overthink it. But the human side of investing gets pulled toward the companies that stand out, the ones that make you curious, excited, even proud to own.

So you end up in this strange vortex:

You know what the simple answer is…
but you’re also drawn to the exceptional.

I’ve been navigating that tension for decades now.

To be fair, it’s a fortunate problem to have. Being in a position where investing is something you can enjoy, even wrestle with philosophically, is a privilege in itself. I’m very aware of that.

Still, every now and then I catch myself thinking:

Maybe I should just stick to boring.

A single global fund.
Profitability tilt.
Automatic contributions.
Done.

No rabbit holes. No company deep dives. No late-night reading about rockets, semiconductors, or energy systems.

But then again… that might take some of the joy out of it.

Anyone else chug along with this same internal debate?

15K views

67 Comments

Ronan

@ronan · 7mo

Absolutely Ian, I appreciate your thoughtful posts

It’s absolutely a struggle and I’ll give you a perspective from the other side.

If I owned a broad market index fund, my life would be immensely easier. No actively keeping up with businesses, no planning a portfolio, no long term research, just simplicity

It’s also what I likely will do in the future, I’ll rotate into broad index funds. My wife actually does own mostly index funds which I put her in, so we always have some of our investments safer.

My investments however you’ll see I own 0 index funds and I made a post about that switch a while ago. I also own Bitcoin, so I’m really getting the fun in.

For me though, it’s not just about picking companies as many people do, I also build my portfolio around position sizing, sectors, beta to help my volatility, revenue diversification, and these other factors to actually help not only maximize returns but keep me safer in a drawdown. Portfolio construction is underappreciated even in single stocks, it’s often forgotten

I also haven’t underperformed and I believe my CAGR since being at wealthsimple (January 1, 2022) is 22% annualized and time weighted. So I can say at least so far it’s been working, but of course a lot of that is entirely luck. So this definitely is a debate, but for me at least I know which side is winning right now haha

Mr Financial

@mr.financial · 7mo

I've done day trading, swing trading, growth stocks, and the. settled on dividend growth investing to stay 'safer'. I've owned at various levels a core of broad market indexes to diversify.

I'm in year 22 of investing and I really wish I made the change to broad market indexing earlier than year 21. It frees up so much of my time to do other things I thoroughly enjoy more than reading quarterly reports or academic research on dispersion of returns.

It is a real psychological battle for me STILL. Especially that I owned single stocks for so long it's hard to not peek at how they are doing. I recently unsubscribed from all their investor relations sites so I don't get tempted to drop retirement money back into an old holding that is looking ripe to pick.

Factors will be my scratch for now 😁

Paul @mrwhite007 · 7mo

The temptation is real! 😂

But I just tell myself that whatever company I’m loving the look of I probably already have it in VEQT!

“Boring” is the way forward!

Liam

@investingmechanic · 7mo

I’ve had this debate with myself and others from time to time, yes the wise safe option is to just do a diversified etf. But for me I find joy in reading stock news, researching, and stock picking. Is there more risk involved? Absolutely but my time horizon is long and I’m aware of the risks involved.

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