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We often don’t realize how our past shapes our relationship with money.
I remember a bus trip with college friends to Atlantic City, New Jersey over 15 years ago. After hopping off the bus, I was really thirsty and spotted a soda machine across the street from the Trump Plaza Casino. While my friends unloaded their bags, I ran over and inserted three quarters into the machine. A whirring sound came from inside, but nothing dropped down. I looked around and, for some reason, reached into my wallet and inserted another trio of coins. The vending machine swallowed my money again with just a whirring sound. No soda. I walked back to my friends empty-handed and embarrassed. We entered the casino lobby and then went ahead to the casino floor.
The casino which at one time hotbed of glamor looked like it had smoked too much, had drunk too hard and needed a shower. I sat down on my first slot machine which had an enticing name of Buffalo Stampede and put tokens. I had $200 in tokens in my right pocket. Within 90 minutes all of my pockets were empty. It was the worst losing streak in my whole life. And it was the only losing streak in my life. The rest of the weekend I just drank soda and watched my friends play. I was so traumatized from the combine loss of my cash from the soda machine and the added insult of the loss from the slot machine that to this day I do not gamble at all.
Risk Aversion in Retirement Planning
Many approach retirement planning with similar caution, focusing exclusively on traditional vehicles like 401(k)s and conservative investments. While this protective instinct serves us well, it may limit growth potential.
Calculated Risks vs. Gambling
Unlike casino games where outcomes are beyond your control, side hustles allow you to leverage existing skills while maintaining your primary income’s security.
The Side Gig Advantage
Side ventures provide unique opportunities to explore additional income streams that might generate passive retirement income, develop into full businesses, or provide fulfilling work during semi-retirement—all with the built-in safety net of your main job.
Finding Balance
Not every side venture succeeds, but unlike gambling, these calculated risks can be managed and adjusted. You maintain control, learn from setbacks, and build on small wins.
The Bottom Line
While healthy risk aversion protects our financial foundation, strategic side gigs can substantially boost retirement readiness. The side project you start today could become tomorrow’s primary income source or the passion that keeps you engaged well into your retirement years.
Jorge Sanchez, MD
Naples, Florida
The Sunday Best 04/13/2025
Epidemiology and pathophysiology tell us that shingles (and related postherpetic neuralgia) is common, and that vaccination should decrease its risk. We have data showing that the Shingrix vaccine is remarkably effective (with efficacy of ~ 90%). So if you’re above 50, this is your sign to get the shingles vaccine!
Auto tariffs appear to be here to stay. Who’s hiking prices, who’s eating the levies, and who’s laying off workers? This is how carmakers are responding to Trump’s auto tariffs, so far.
The prospect of a falling stock market mixed with rising bond yields, slowing economic growth and higher inflation was enough to force a pause in tariff policy. The bond market forced Trump’s hand for the time being. And the stock market is repricing immediately.
But the reprieve is only partial and temporary. The very high tariff on China is still in place (and in fact has been increased). The 10% tariffs on all imports are still in effect. “Sectoral” tariffs on autos and other specific products are still there, and also those on Canada and Mexico. Here are all the terrible pro-tariff arguments.
The S&P 500’s daily ranges in each of the first three sessions of the week all rank in the top 35, based on data going back to 1982. Off-the-charts stock market volatility is a sign we’re living financial history.
Bear markets expose your fear because they expose your asset-liability mismatch. We don’t get scared because the stock market is risky but because the uncertainty across time becomes obvious. An environment like this raises the temptation to sell stocks and obtain cash because holding cash gives you 100% certainty of future principal.
It’s easy to make money buying stocks if you look at it on a frequency scale. But the system skews. Magnitude matters. You can make a little money most of the time, but you risk losing a lot of money a little of the time. It’s always been this way. Thankfully, the wipeouts only feel like wipeouts: the average positive return of the S&P 500 (again, about 10% per year) includes the wipeouts.
Under the umbrella of these uncertain times, there’s a good chance that you or your partner might end up in a bad place. But when you know each other’s coping behaviors, you can recognize them as a signal for when there might be more simmering beneath the surface.
The common thread in currency and bond markets is that thanks to Trump, dollar assets — traditionally the foundation of the global financial system — are no longer perceived as safe. The combination of interest rates soaring amid a slump and the currency plunging despite rising interest rates isn’t what we usually expect for advanced countries, let alone the owner of the world’s leading reserve currency.
The Department of Education laid off half of its employees. Whether you believe this is a good idea or not, based on your political views, these actions profoundly impact the college application process.
The number of doctors wanting to relocate outside of America has been rising for years now, but it has become more apparent in the past couple of years. Factors such as burnout and dissatisfaction with the healthcare system are commonplace, but some, like gender, also come into play.
Despite a healthcare budget that could be the fifth-largest total GDP in the world, we have some of the worst patient outcomes in the world, with the highest maternal and infant mortality rates. Americans tend to have a lower life expectancy at birth and the highest number of individuals with multiple chronic illnesses.
And lastly, when you’re living through market drops or crashes, these moments of economic turmoil can feel both scary and catastrophic. But during these times, it’s worth taking a moment to put things in perspective.
