Should you invest in the stock market at all-time highs?

It’s been a good year so far for index investors as US, global and Canada indices hit all-time highs. At the time of this writing the S&P 500 is up over 13% from the start of the year. The FTSE 100 is up 11% and Canada’s TSX is up 19%. Despite tariff threats and geopolitical tensions, the stock market has continued marching upward, buoyed by weaker than expected US inflation numbers, a confident consumer and the hopes that AI will deliver cost savings and record profits for every type of business imaginable. The US Federal Reserve’s September interest rate cut of 25 basis points has further encouraged investor sentiment during what is historically a poor performing month. Septem’bear’ is now effectively known as ‘Septem-‘bull’.

2025 Mid-year stock market update

While the first three months of 2025 saw mild stock market declines, things really started falling off the rails on April 2nd, otherwise known as ‘Liberation Day’. During a formal rose garden ceremony, President Trump held up a large board announcing reciprocal tariffs on approximately 60 countries and a universal tariff of 10 percent. These countries had been “ripping off” the US for years, Trump insisted, although economists would argue that his calculations were a tad embellished and tariffs over-reaching, as even an island inhabited only by penguins would be tariffed. Indeed, no one is safe in a trade war.

Chapter 18. The sun always rises

It’s still dark in our hotel room with the curtains closed. Victor is usually up before me, at the gym or reading an article in another language. But this morning I’m up even earlier than him. I put on my hotel robe, quietly make a coffee, tip toe outside to the balcony. The sun is rising on the horizon. Pinks and purples paint the sky.

Chapter 17. You can go home again

The empty two-bedroom condo echoed as I walked along the hardwood floors and opened the balcony door. July’s oppressive heat hung heavy. Our second-floor unit looked out on a cluster of trees, some pine, a gentle reminder of the northern land I had left behind. Just one month ago we had given away everything no longer needed for our new down-sized life in Toronto. Salad spinners, pots and pans, backyard furniture littered our manicured front lawn with a ‘free’ sign. Neighbours were confused. Who just gives away perfectly good stuff?

Chapter 16. There is nothing “real” about real estate / or, An offer we couldn’t refuse

My head was spinning. Having scrolled through page after page of realtors, we were having trouble deciding which one we should contact to help us sell our house. They all looked eerily similar. Blazer, chicklet smile, coiffed hair, arms crossed in a confident, yet approachable stance.

Chapter 15. This housing market is “exploding”!

By the spring of 2023 the markets were green year-to-date! We were still far from our historic highs of December 2021, but with the bear market of 2022 in the rearview mirror and inflation coming down, 2023 was shaping up to be positive. Around this time, on a warm Sunday morning Victor and I were getting ready to leave on vacation. After years of Covid-related travel restrictions we had booked a dream trip to Greece. I was busy checking everything off my list to shut the house down for two weeks. Clean out fridge and empty garbage, check. Turn the air conditioner off, check. Make sure back door is locked, check.

Chapter 14. Can you bear the market?

What is a bear market like? If a bull market is identified by its bull-like tendencies, your portfolio aggressively raging upwards in a sex-crazed rampage, then the bear market is much like a bear itself. It’s scary, temperamental, and your portfolio goes into hibernation until further notice. Like a mama-bear protecting her two cubs, investors sell off their stocks and desperately search for what they believe to be safer assets, like gold and consumer staples. But the damage is already done, with equities having crashed anywhere from 20-30 percent. Your portfolio is cooked, and you have one long winter ahead of you.

Chapter 13. Am I ready to retire?

Around this time I started to think about early retirement. I looked at my budget and I compared it to my healthy portfolio now bursting at the seams. I had been working towards financial independence for a while now, basing my plans for early retirement on the Trinity Study. I recalled from reading JL Collins, that based on the study, you can safely withdraw 4% of your portfolio annually, indexed to inflation, and you will have a 96% chance of not running out of money over a 30 year time period (source). For example, if you have $1,000,000 invested in a mix of stocks and bonds, based on the study you can safely withdraw 40k/year and let your portfolio do the heavy lifting while you’re frolicking in fields of dandelions, enjoying early retirement (source).

Chapter 12. The raging bull marches higher

In the meantime, as I attempted to fix more broken appliances, the stock market continued to soar to new heights in 2020 and 2021. Despite the Covid bear market in early 2020, the S&P 500 gained 18.4 percent in 2020 and went on to reach even newer highs in 2021, returning 28.71 percent by the end of the year! Covid had sadly ravaged small businesses and inflicted pain among sectors of the economy like the service and travel industry. But corporate America was alive and well and several factors ensured both the stock market and housing market continued to thrive. Lowered interest rates, pent up consumer demand and a shift to digitalize work and play were driving up the prices of stocks –  and real estate.

Chapter 11. Home ownership: The good, the bad and the ugly

Could I still achieve financially independence and embrace minimalism as a first-time homeowner? Or would the stress of mortgage payments and ongoing home maintenance affect my finances and mental health? I was about to find out.

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