Disclaimer: I am not a financial advisor. This post is for entertainment and informational purposes only. Any investing decisions you make are your own responsibility. Do your own research, consult a professional, and invest at your own risk.

---

I took an Uber to ServiceOntario yesterday to finalize the purchase of a second vehicle for my family—a private sale on a 2015 Subaru.

Holding off on a second car wasn’t always convenient, but it made sense. We were patient, waiting for the right car at the right price by the right seller in the right location at the right time.

Now, I was finally making the trip to seal the deal—except I was running late. I’d left work late, booked the Uber late, and was now cutting it close for my meeting with the seller. I sat back and took a breather.

Phil Collins played harmlessly in the background, and I asked the driver if he chose his radio stations based on his appraisal of his passengers.

He laughed and said no.

He told me he used to listen to The Jewel, a station that played old-school jazz, but once it started recycling the same mainstream hits as everywhere else, he switched to easy listening.

“You like driving Uber?” I asked.

“It’s like the radio station,” he said. “I don’t love it, I don’t hate it.”

“”The Phil Collins of employment,” I said. “I think I’d enjoy Uber driving, but I’d probably end up listening to audiobooks the whole time.”

“That’s what I do when I don’t have passengers,” he said.

I nodded. “What are you listening to right now?”

“Books on options trading.”

“Interesting,” I said. “I also invest, but I’ve never gotten into options.”

“How long have you been investing?” he asked.

“20 years, I guess,” I replied.

“What have you learned?” he asked.

I wasn’t ready for the question, but I’ve been thinking on it since. Turns out, you can’t do something for twenty years without some sort of takeaway.

---

20 Lessons from Two Decades of Trading

1. It’s generally a good idea to avoid investing in something that isn’t profitable—unless it’s a brand-new (and therefore volatile) market no one mainstream is talking about yet. If you do, having an exit strategy is key.

2. Staying active while investing can be useful. Buying and selling smaller positions while waiting for a bigger opportunity can help build familiarity with industries and trends.

3. Taking big risks may only make sense when a stock has a small market cap, high growth, and good value—a combination that can reduce risk compared to purely speculative plays.

4. It’s worth understanding what a high-potential stock looks like. Some key indicators: low price-to-earnings ratio, strong revenue growth (25%+ per year), and a small market cap. Bonus: If there’s a comparable company in the industry that has already seen major gains, it could be a promising sign.

5. Some choose to delay investing in large- and mid-cap stocks until they’ve built wealth. The reality is, it’s harder to get significant returns from established companies unless you started very young (or got extremely lucky).

6. One approach is to tie an exit strategy to real-life financial goals. For example, some traders look at their mortgage balance and use that as a target.

7. High risk doesn’t always mean high reward. Without a clear strategy, selling at the right time can be difficult.

8. Talking to others about stocks can be helpful, but most people focus on well-known companies. The real opportunity may lie in learning about up-and-coming competitors in growing industries.

9. Financial forums (ceo.ca, Stockhouse, Yahoo Finance) can be a useful source of insight—but like anything, it’s good to verify claims and do independent research.

10. Reading The Globe and Mail and other major financial news sources can be helpful for general market awareness—but by the time they cover a stock, early investors are usually already in.

11. It’s best to avoid convincing others to invest in something unless they’ve done their own research. If it doesn’t go well, conversations can get awkward.

12. Some investors go all-in when they find a high-potential stock—sometimes even leveraging credit lines. This approach is not for everyone, but some have found success with it.

13. Checking a stock’s long-term chart can provide valuable insight before making a decision.

14. Investing ethically may be worth considering. Some people prioritize companies that contribute positively to society.

15. Many experienced investors develop a long-term exit strategy. This often involves calculating how much income they want in retirement and planning backward.

16. Big opportunities don’t come along often. Some believe that in a decade of investing, only a few major chances will present themselves.

17. Some investors believe that saving aggressively early on allows them to make bigger, more meaningful investments down the line.

18. Diversifying interests can help keep a balanced perspective. It’s easy to become consumed with the market, checking stock prices constantly—even when the market is closed.

19. For some, getting caught up in short-term price differences isn’t worth the stress. If a stock is undervalued and has strong growth potential, it may make more sense to focus on the bigger picture.

20. Some experienced investors define a “big fish” as a stock with the potential to 10x in value. Not all stocks will reach this level, but identifying companies with this potential can be a useful strategy.

---

The Destination

Did I share all this with my Uber driver? No. Like I said, his question caught me off guard.

Did I learn anything about options trading? No—though I wish I’d asked.

As we neared ServiceOntario, my mind shifted to whether I had everything I needed for the car purchase. I was stoked. I’d done my due diligence, negotiated a fair price, and waited three years before pulling the trigger.

In the meantime, we saved. We invested elsewhere. Cut corners. Got by with one vehicle.

Because that’s what it takes to get ahead. You save. You wait. Right opportunity, right timing, right price.

Investing is a broader concept than we realize.