Every week I receive questions from clients, friends and family who are curious about the uncertainty we are seeing as of late.

I've been asked: What are we supposed to do over the next 4 years with the Administration’s continuous change in policies? I went heavy into cash before Trump took office. I trusted that he was going to keep his word, and break things. I just didn’t expect him to break the market. But now I’m stuck, fearful of this constant uncertainty that seems to never go away. It’s already been a long 3 months. I was planning to retire this year, but unlikely now. My Money Market is getting that decent 3% yield right now, and at least this helps me sleep at night.

I've also been asked: I’m a 50 year old in good financial position at the moment. That said, I’m not bullish on the economic future. I’m not interested in hoarding gold bars, but would like to put a portion of my portfolio in investments that would do well, or at least better, in a world where income inequality, protectionism, AI advance, and America’s social fabric continues to fray. What would you recommend?

There were numerous questions along the same lines. People are worried.
It’s crazy how quickly the narrative has shifted. Just a few short months ago there was talk of Trump being the biggest pro-business, pro-stock market president ever. Life comes at you fast. If Trump keeps up the current trade policies it’s going to be bad for the global economy, supply chains, profit margins, consumer prices and corporate earnings. There is no sugar coating it. These are not pro-business or pro-stock market policies. They are the opposite. But you can’t just go into the fetal position because this makes you nervous. You still have to invest in something.

These questions came from people at different life stages, so I’ll tackle them separately:

Let’s say the worst does come to pass and the next few years are bad for the economy and the markets. Take away the reason. The reason doesn’t matter. When you’re in retirement, you have to expect economic slowdowns, bear markets and corrections.

A couple retiring today in their mid-60s has a 50-60% probability of at least one of them living until age 92. There will be a presidential election in 2028. That’s less than four years away. Your retirement could last 20-30 years. 
One of the big risks for retirement investors is sequence of return risk. You don’t want bad returns early in retirement to derail your investment plan.

Therefore, you need to consider how many years’ worth of spending you have stashed away in safe, liquid assets to see you through the inevitable periods of disruption. That’s true regardless of who the president is. Unless you have a giant pile of cash, that money market fund isn’t going to help you keep up with inflation over the coming decades. You have to take some risk in retirement if you wish to beat the increase in standard of living. Retirement planning still comes down to your time horizon, financial circumstances, and
personal spending habits.

Uncertainty in retirement never goes away but you have to focus on what you control and make course corrections to your plan along the way. It’s also important to recognize that stock market returns have been fantastic even when you include the current correction. Over the past 5 years, the S&P 500 is still up 16% per year.

The wrong question: Should I sell all of my stocks?

The right question: Should I change my allocation?

If you’re 100% stocks and this makes you that nervous maybe you should be more like 80/20, 70/30 or 60/40. I’m never a fan of going all out with no plan on the other side of that decision. Asset allocation is more important than market timing. Investing in middle age is often overlooked since personal finance experts tend to focus on young investors (stay the course) or retired investors. At 40, you should have some financial assets but you also have plenty of time left to save and invest. It’s a balancing act.

I don’t know if you should be pessimistic about the future of our economy but bad times should be expected when you have a multi-decade time horizon. Listen, I could give you a portfolio to protect your assets with a bunch of different strategies. Maybe it works, maybe it doesn’t. The perfect portfolio is only known in hindsight. These are the times when diversification matters more than ever. It’s not only a risk management strategy but a way to ensure you invest in the eventual winners (which we won’t know until after the fact).

Your ability to stick with a strategy will be more important than the strategy itself. If you’re really that nervous about the economy, save more money. Do your best to improve your career prospects and increase your income. It’s also worth pointing out that predicting the future is hard. No one would have expected things to turn out so well after Covid hit. Just take a breath and see how this all plays out.

I’m not going to lie, I don’t have a lot of faith in our political leaders in either party these days. But I still have faith in the Canadian spirit of ingenuity and entrepreneurship. I still have faith corporations will do anything they can to innovate and grow. That hasn’t changed.

Not letting emotions drive our decisions but rather letting our plan take control is truly what matters during times like these.

With my 35th birthday just around the corner, I've been reflecting on the milestones and life experiences that shape our understanding of money. My career has given me a front-row seat to the intricacies of real-world money management, blending professional training with personal insights. I feel incredibly grateful for the opportunity to guide my clients through their financial milestones, learning alongside them every step of the way. I've gathered a decade’s worth of observations, each lesson serving as a stepping stone toward greater financial empowerment for both my clients and their families.

Here they are in no particular order:

1. Your income is the most important part of your financial picture. Many people waste time trying to cut things from their budget or get an additional 2% return on their investments, but putting all your energy into getting a raise will get you richer faster. Your career is your most important financial asset.

2. There has never been a crash that the stock market did not recover from and go on to reach all new heights. There is no reason to fear the market is going down. There is no reason to think it will “never go back” when it does. This has quite literally never, ever been true - and if it ever is, we’ll have far bigger concerns than our portfolios being down.

3. Almost all financial news is designed to get clicks for ad revenue, not to inform or empower retail investors. You should ignore virtually all of it. If you do check in on the financial news, you should consider it the equivalent of a man on street corner yelling about the end times. It’s not worth adjusting your day for, let alone your portfolio.

4. Money is only useful unless you spend it, otherwise it is simply numbers on a screen. Many people strive towards a certain account balance, but the only reward for having money is being able to say you have it. Unless you convert it into life experiences by spending it on travel, experiences, or material goods, you will quite literally reap absolutely no benefit from your “wealth.”

5. Your objectives should be wealth preservation first, and growth second. It’s tempting to take big risks for big wins, but these too often result in big losses. One wrong move in the stock market because you became greedy can erase years of savings in an instant. You should build your financial plan around stable consistent gains rather than chasing exceptional returns. You can afford to be an exceptional investor, but you can’t afford to be bad one.

6. Most people will tell you how to get wealthy the wrong way, because most people are not wealthy. Do not take financial advice from anyone who is not where you want to be. We can learn something from every person we meet – what to do, and what not to do.

7. Equities are simply the best assets to become wealthy. I may be a tad* biased here, but after seeing hundreds of Canadian’s finances over the years, owning equities (stocks) has created more wealth than any other asset class.

8. Do not procrastinate all your life experiences until retirement. Many people imagine retirement as a financial utopia where they finally get to enjoy the spoils of their labor. In reality, if you retire at age 65 you will have approximately 10 good years before your health begins to  decline, and then you have approximately 10-15 more years of that before you die. Make sure you take some life experiences now, even if they have to be at a slightly lower level of luxury. It is better to stay at a 3-star hotel for 7 days in your 40s than a 5-star hotel for 10 days in your 70s.

9. I will never be a landlord again. It wasn’t that I personally had a bad experience as a landlord, but the landscape has changed in Ontario significantly. For the amount of risk and capital needed, the returns just simply don’t make sense compared to owning a globally diversified portfolio with proven returns.

10. If you manage to achieve some level of financial security or wealth, be exceptionally generous with money. Most people are struggling and will appreciate when you pick up the tab for dinner, give them a thoughtful gift, or get them out of a financial bind with no strings attached.

11. No one cares more about your possession than you. Your car, your watch, your home, expensive bottles of wine. No one will care more about these than you. If you were to live on a remote island, where no one would see your car or house, what would you drive? What house would you live in?

12. Do not invest your Emergency Fund. Do not worry about your Emergency Fund “just sitting there, earning no return.” The purpose of an Emergency Fund is not to earn a return. It’s to protect you in the event of an emergency. If it’s doing that, it’s working.

13. The middle class has been lulled into complacency by cheap credit. The reality of what we can afford is what you can buy when you don’t use lines of credit, credit cards, car loans, or HELOCs. You’ll realize right away you’re much worse off than you think. If you cannot afford the live you want without debt, you need to earn more money or adjust your expectations.

14. Don’t choose a partner who is bad with money. It doesn’t matter how much you love someone, if they are not on board with your financial goals, then you are fundamentally incompatible as a couple. Joining your money with a partner’s will supercharge your wealth accumulation if you can work as a team, it will decimate your financial security if you can’t. Second only to choosing your career, who you marry is the most important financial decision you will ever make.

15. Stop complaining about inflation, house prices, wage inequality, or any other economic grievances. It is good to acknowledge and understand these exist so you can work around them, it is ridiculous to make them the singular excuse as to why you can’t get where you want to go. No one gets to opt out of the world we live in. Complaining about it doesn’t make it better.

16. Investing in friendships is a form of true wealth. Becoming wealthy without friends to enjoy it with seems awfully hollow. A call, text message or lunch to catch up is an investment in a relationship and its so easy (and easy not to) do. Text someone today you haven’t reached out to in a few months.  

17. If you’ve made a financial mistake, accept it, fix it as quickly as you can, and then move on. There is no use ruminating over “if I had never done X then I would have Y.” Staying upset at something in the past that you cannot change will take emotional and mental energy away from planning a richer future.

18. If a stock you own has tumbled more than 40% and you’re “waiting for it go back up”, sell it. Your brain has mistakenly anchored your purchase price, or the highest price the stock reached, as its rightful one. But the stock market doesn’t work that way. Just because a stock was once a certain price doesn’t mean it will go “back” there, especially if its current trajectory is down. There is a huge opportunity cost to holding an underperforming investment, and doing so is making an investment mistake on top of another one.

19. The best way to spend your money is on experiences, but not all experiences are travel. You can be more creative in your spending than using it to simply physically be in a different place.

20. Money is correlated with higher life satisfaction, but only if you spend it on the right things. Statistically the data indicates the things that make us happiest are strong social ties, meaningful work, and hobbies. You can work on these three things regardless of what your financial situation currently is, and you should prioritize them and make them central to your life as you pursue your financial goals.

21. The less you can control something, the less mental energy it should take up in your financial planning. You have no influence over the Trump presidency, there is no reason to agonize over how you should adjust your spending or investment allocation to prepare for it. The things you can control are your income, savings rate, and spending. This should occupy 90% of your focus.

22. Don’t mistake correlation for causation in finance. Many people mistakenly believe that owning a home makes you wealthy, because homeowners are disproportionately wealthier than renters. But the reality is rich people behave a certain way because they’re rich, not because that that is what made them rich in the first place. The answer is as boring as rich people tend to buy houses because they are the ones that can afford them.

23. Your net worth is the most important financial metric to assess how you’re doing financially, and it’s a lagging indicator of how well you’re managing your money. Good financial decisions will take months and years to show up in your net worth calculations, but as long as you’re taking care of your money you will see progress over time.

24. Try to buy things that last. This is becoming more difficult in our age of fast fashion and planned obsolesce, but the frequency at which we are purchasing items is much more detrimental to our financial security than their price. You can do more with less if you buy things that last.

25. Ethical investing is largely made up. We live in a corrupt system built on the exploitation of people and the planet for profit. There is no way to participate in the stock market ethically. Unfortunately, there is no way to build wealth and financial security without participating in the stock market. Yes, this is by design.

26. Debt is not a moral failing, it is an expense. If you feel guilty or ashamed of the purchases you made that resulted in debt, remind yourself that you made the best decision you could with the information you had at the time. Paying off debt is an act of healing and self-care. You should take it as seriously as any other process of growth and development.

27. Celebrate small wins and accomplishments along your financial journey. After a big accomplishment, stop and recalibrate. You will not derail your entire financial future by taking a one month break every few years. In fact, doing so might reinvigorate you to tackle the next goal.

28. No one cares about your money as much as you do. Most people will not care how much you have, and it will not change your relationship. Many people worry that an unexpected inheritance will alter the dynamics of a friendship, especially if they result in a jump in socioeconomic class. But the truth is most people will not think about how much money you have, let alone care. You shouldn’t either.

29. Sometimes "good" money behaviours are really just unhealed money trauma. This can look like obsessive budgeting, the reluctance to spend money, or worrying incessantly about having enough in retirement. Anything that makes you anxious about money is probably an emotional issue and not a financial one. Financial issues are really easy to solve, the emotional healing will take longer.

30. Most wealth is made at the end. Warren Buffet accumulated 99% of his net worth after the age of 60. Your story probably won’t be so dramatic, but approximately 40% of your portfolio will be accumulated in your last 5 to 10 years before retirement. Remember this if it feels like things are moving slowly.

31. Money will solve a lot of problems in your life but not all of them. Even when you achieve financial security you will still need to do your laundry and heal your childhood trauma and make dentist appointments. Do not spend too much time fantasizing about the life you’ll live once your finances are handled. When you will inevitably get there, you will be disappointed to see the day-to-day is actually not that much different from the life leading up to it.

32. There will inevitably be leakage in your budget and your financial journey. You will occasionally overspend on internet service or winter tires. Something you thought would be a great use of money will turn out not to be. You will sometimes not be able to return that thing you bought that you thought would be useless. It’s not worth it to get upset or hold resentment over the times we let money go that we know we shouldn’t have. Life costs money. Not all of that money will be as useful as we want it to. There’s nothing to do but accept this and move on.

33. Try to Die With Zero. Do your best. Life is not a game of trying to get the highest number in our bank accounts, though we all treat it as such, but dying with a high net worth benefits no one except the tax man. The money in your bank account at your death represents missed dinners out with friends, vacations never taken, hobbies never pursued, and experiences never enjoyed.

34. Health matters, a lot.

35. The real richness is life is having a future to look forward to. Most people obsess about money because the alternative to that is accepting our own mortality, and it’s easier to worry about dollars than death. But if you got to wake up today and enjoy a cup of coffee, if you have plans for the weekend and Christmas and are thinking of taking a trip next year, you’re already very wealthy. There are people with money who don’t have that.

I once saw a Reddit post that said, “Imagine someone offered you $10 million dollars. But the catch was once you accept, you won’t wake up tomorrow. Would you take it? Of course not. Is there any sum you would accept if it meant you couldn’t wake up the next day? Probably not. In fact, the more money you’re offered, the more useless it becomes if you simply die the next day. This means every day of your life is more valuable than any amount of money on earth.”

As of today I’ve had 12,775 days on this planet. I probably have another ~18,000 to look forward to. That’s the richest I’ve ever been.

As we step into a new year, it’s worth reflecting on a fundamental truth about investing: the economy, markets, politics, and global events are inherently unpredictable. The only certainty is that surprises will continue to come our way.

Let's review some of the surprising (and not so surprising) events that 2024 brought our way:

• The stock of the leading U.S. chip manufacturer (Nvidia) tripled.

• The U.S. Fed reduced its essential interest rate a quarter of a point one day in December, just like everyone expected they would. And the S&P 500 went down pretty close to three percent that day.

• The VIX—which journalism describes as the fear index, but which I prefer to think of as the stock market’s blood pressure—went up 172% in one day, in part because of the unwinding of something nobody had ever heard of before called the yen carry trade. (If that actually were someone’s blood pressure, he’d have had a stroke.)

• The stock of a company that buys and holds a particular cryptocurrency—that’s all it does—went up about 480%. There was more, but you get the point. The year 2024 was replete with utterly astonishing surprises—both positive and negative—that seemed to come out of nowhere. Like every other year.

By the way, does anyone remember that interesting year 2022, when inflation spiked to nine percent? And set off the fastest, steepest sequence of Fed rate hikes that produced the worst year for the traditional 60/40 portfolio since 1937? (That’s not a misprint.)

Or how about 2020, when a deadly hundred-year plague shut down the world economy, and caused the S&P 500 to decline 34% in 33 calendar days? It's helpful to note that all of these events cover a mere four years.

Now layer in just a few of the massive political/geopolitical shocks of this same period:

• The war in Ukraine.

•Hamas’s invasion of Israel, and the latter’s response throughout the region.
• The sudden and total collapse of the 50-year regime in Syria.

• A sitting U.S. president driven from his reelection campaign on grounds of incapacity, about 100 days before the election.

• The resounding reelection to the presidency of a person awaiting sentencing in a felony case.

It's enough to make you need a time out just to absorb it!

I can go on and on like this. But the twofold conclusion should be obvious.

1.  The economy, the markets, politics and geopolitics are for all practical purposes perfectly unpredictable. The only constant is complete surprise. 

2. If we let utterly random current events of any kind alter our investment policy, we never really had an investment policy, and are thus doomed to fail as investors.

If this blog accomplishes nothing else, I hope it convinces you to start the year by sitting down with me and saying in effect, “I get it now. I can never be a successful investor by trying to anticipate the news, and even less by reacting to the news. Let’s continue our plan. The one I can stick with through good news, bad news, and totally random news.”

Allow me to suggest that all of investing can be encapsulated in that simple duality: are we going to run our investment portfolios based on a plan, or in response to an endless stream of news that comes relentlessly at us from deep left field?

This is the year to make that decision.

Heck, today’s the day to make that decision.

As look ahead to 2025, many of us are eager to embrace change and growth. But why do we have to wait until the clock strikes midnight on January 1st to start?

Living your best life doesn’t have to mean a radical transformation or a grand resolution; sometimes, it’s about making simple, thoughtful choices every day that add up to a happier, healthier, and more fulfilling life.

Here are some approachable, practical ways to make 2025 a year of positive, sustainable change and there's no reason we can't start now!

1. Prioritize Mindfulness and GratitudePracticing mindfulness doesn’t have to mean hours of meditation. Start with a few minutes each morning to set your intentions, breathe deeply, and take in the present moment. Reflecting on what you’re grateful for, even just one thing a day, helps shift your mindset towards positivity.

2. Simplify Your SurroundingsCluttered space, cluttered mind: a cleaner, simpler environment promotes a more relaxed and focused state of mind. Declutter your home and workspace, focusing on quality over quantity. You don’t need to overhaul everything at once; start with one room or even a drawer at a time.

3. Move Your Body Every DayIf you know me, you know exercise is foundational to my wellness. But exercise doesn’t need to be an intense, hour-long session at the gym. A short daily walk, a quick yoga routine, or a dance break can all contribute to your physical and mental health.

4. Focus on Financial WellnessLiving your best life includes feeling secure about your finances. Financial wellness doesn’t require a complete overhaul or strict budgeting. Start by assessing your financial situation and setting small, achievable goals—whether it’s building an emergency fund, paying down debt, or saving for a future goal. Consider consulting a CERTIFIED FINANCIAL PLANNER professional who can help you establish a clear plan. Financial wellness is about building a sense of stability and peace of mind for the future.

6. Set Realistic Goals and Celebrate Small WinsSetting realistic, achievable goals and breaking them into small steps helps create a sense of progress without overwhelming you. That's what planning is all about, whether it's financial or otherwise. Make it a habit to celebrate small wins along the way. These victories build momentum and keep you motivated.

7. Embrace Lifelong LearningA commitment to learning—whether it’s picking up a new skill, hobby, or reading a book on a topic you’re interested in—keeps your mind engaged and curious. Continued learning enriches your life and keeps you adaptable in a rapidly changing world. Try to learn something new each month or set aside time each week to explore something you’re passionate about.

8. Get Enough Rest and RecoverySleep is foundational to physical and mental health, yet it’s often one of the first things we sacrifice. Try setting a regular sleep schedule and aim for 7-8 hours each night. Quality sleep enhances focus, reduces stress, and improves your mood. Beyond sleep, make time for relaxation throughout the day—whether that’s taking short breaks, practicing deep breathing, or stepping outside for fresh air.
​Wrapping Up: Start Small and Be PatientLiving your best life in 2025 doesn’t require drastic measures. Small, intentional changes are often the most sustainable and meaningful. Most importantly, focus on the journey and celebrate your progress along the way. Here’s to a year filled with mindfulness, simplicity, connection, and well-being - and not waiting for an arbitrary (or not-so-arbitrary) date to get started.

At the turn of the 20th century, banker J.P. Morgan was the most powerful man on Wall Street, perhaps the most powerful man in the world. Finance in those days was still the Wild West, largely unregulated and prone to boom and bust cycles much more violent than anything we see today. On several occasions, Morgan personally orchestrated emergency measures to stop bank runs that might have otherwise taken down the financial system — typically increasing his own wealth in the process.

Shortly after one of those near misses, the Panic of 1907, an old friend of Morgan’s from Chicago came for a visit. The friend was, in the phrase of Mark Skousen, from whom I got this story, a “perma bear” — no matter what the market did, his outcome was always pessimistic. As usual, he and Morgan got to talking about the markets. And as usual, Morgan’s friend saw poor omens in every market indicator, while Morgan saw only buying opportunities. Eventually they headed out for lunch, and, walking up Broadway, Morgan’s friend was admiring the towering skyscrapers that were starting to define the Manhattan skyline. Impressed, he acknowledged they had nothing like them in Chicago. Eventually, Morgan stopped and turned to his friend. “Funny thing about these skyscrapers,” he said, “not a single one was built by a bear!”

Six years before that conversation, Morgan had completed his purchase of Andrew Carnegie’s entire steel operation for the unheard-of sum of $480 million, hundreds of billions in today’s dollars. You don’t do that deal and amass that kind of wealth with a persistently negative outlook. Count the perma bears on the Forbes 400 list or the number of pessimists who run companies in the Fortune 500. You will find none.

Winners and other men and women of foresight and ambition do monumental things; pessimists watch them from the sidelines, making a list of all the reasons things won’t work out. The losers do get to win sometimes, too. But their victories tend to be short lived, as every calamity ultimately leads to opportunity when the dust clears.
 
Bullish

In 2009, deep in the depths of the Great Financial Crisis,  Sam Zell  spoke to an audience of real estate investors and developers. He told us that “kings would be made” in that moment. He had nothing left to sell anyone, having blown out of his massive real estate holdings just three years earlier in a time of optimism. Old Sam had seen too many of these cycles; he knew that you always bet on positive outcomes, and you bet heavily when you’re alone on that side of the trade. It doesn’t always work, but it mostly does
Pessimism is intellectually seductive, and the arguments always sound smarter, especially when they dovetail with our own worries. In the early years of the recovery from that crash, Sam’s advice (which Morgan would have echoed) was hard to follow. Even four years later, in 2013, when the stock market finally made it back over the 2007 high, optimism was scarce.

There were all sorts of reasons not to trust the recovery, and if you know anything about the media, then you know they had been relaying these reasons to us morning, noon, and night, repeatedly admonishing us lest we get too optimistic. Valuations were high, they said, while earnings would surely disappoint. Interest rates would rise. Various debt crises would ensue. Demographics were unfavorable. Obama’s healthcare plan surely meant the end of America. A looming government shutdown that fall would undoubtedly be the nail in the coffin.

And yet, somehow none of those things sank us. The year 2013 turned out to be the best for stocks since the halcyon days of the late 1990s. The Dow Jones Industrial Average finished the year up 26.5%, its best finish in 18 years. The S&P 500 had its best annual return in 16 years, capping out the year with an almost 30% return, ending December at a new record. The Nasdaq soared 38.2%, led by an emerging group of biotechnology and solar stocks that put on an extraordinary show for a new generation of growth stock enthusiasts.

A new car company came out of the woodwork, too, and its relatively unknown CEO, Elon Musk, appeared on the cover of Fortune magazine as “Businessperson of the Year” in December. Tesla’s stock was up over 350% in 2013, kicking down the door to a new era while clearing the cobwebs of the aughts decade crisis away. Tesla’s rise and Musk’s wholly unorthodox approach to building his business represented the start of something entirely different from what we were accustomed to. This brought out as many haters and doubters as it did fans and acolytes. What was clear to both sides, however, was that something was changing.

For every negative you could have cited about the environment of 2013, there were plenty of reasons for optimism, as stocks reached new heights and smashed through a wall of skepticism. You just had to work a little harder to find them. This was true then, and it is true now. It will always be true.

Why do I feel like history is once again repeating itself? Because there will ALWAYS be a reason not to invest. Every single week it seems there is a new problem emerging and another catastrophe DuJour – this is the constant in our life.
What else is constant? That despite the problems we have seen in years past – markets continue to go higher, we evolve as humans and life expectancy continues to climb higher as technology advances.

Bear Hunting
Today we are once again contending with all sorts of threats to our future well-being. Earnings expectations, we are told, must ultimately revert lower once companies run out of price hikes they can put forth, while the cost of employing people and running a business will surely increase. Profits are too high and must come down. Higher interest rates have put the real estate market on freeze and how would we not mention the recent U.S. Presidential election.

Talk to the average person on the street, and there’s almost nothing good worth saying. The polls are nearly unanimously negative.
“It’s bad and likely to get worse.”
What is bad? What is likely to get worse?
“I don’t know. It. Everything.”
OK, nice talking to you.

My point is that it’s easy to make lists of problems. Of everything that could go wrong or get worse. I could do it with my eyes closed, and so could you.

But the optimists are eventually proven right. Not every day, but always and eventually. Indisputably. It just takes a while to be able to see it play out. Even if you don’t believe me, make your investment in the future anyway, just in case I end up being right . Plant your seed regardless. If you end up being right in your pessimism many years from now, we will all have bigger problems than what our investments are worth. Being optimistic all the time is difficult. But having any other disposition as a default setting makes little sense when you’re investing for a future far out in front of us.

Of the many ways we can choose to live, I choose to live with optimism as my default setting.

Let's talk about something we all think about from time to time: those "what ifs" in life. As a financial advisor who's had the privilege of helping many clients transition into retirement over the past decade, I've heard a lot about what they wish they had done differently in their careers. The same can be said for their regrets about retirement.

Those of us who are in the career-building phase of life might be dreaming of the perfect retirement; but what if we could access the wisdom of those who came before us to avoid some of their common regrets? On the other hand, if you're considering retiring in the next five years, I want you to be able to steer clear of the most common retirement regrets I've encountered in conversation with clients who have been retired for many years. By learning from these real-life experiences, it's my hope that we can all make smarter decisions and aim for a life journey that's truly fulfilling.

First up, career regrets of retirees:

Not Pursuing Passion Projects: Many clients tell me they regret not following their passions or taking risks to pursue more fulfilling careers. The fear of financial instability or the comfort of a secure job often kept them from chasing their dreams.

Overworking at the Expense of Personal Life: A significant regret among retirees I talk to is having spent too much time working and not enough time with family and friends. The pressure to climb the career ladder often led to neglected relationships and missed life events.

Not Enjoying Life in Pursuit of Saving Money: If you know me, you know this is a huge concern of mine and one that I work hard to help clients feel peace of mind about their financial plan so they can avoid this regret. Clients often tell me they regret not investing more in experiencing life along the way in favour of saving money for retirement. It's common for people to have difficulty making the switch from saving to spending, especially when they haven't been able to enjoy the fruits of their labour along the way.

Failing to Continue Learning and Growing or Staying in Unfulfilling Jobs: Some retirees tell me they wish they had pursued further education or skill development. Sticking with a job that didn't bring joy or satisfaction is a common lament. Many wish they had sought out more meaningful work rather than staying in a role out of convenience or fear of change.

Do any of these feel familiar to you? The key is to be proactive, thoughtful, and willing to make changes that align with your long-term happiness and well-being.

Now, let's compare those regrets with common retirement regrets I hear from clients:

Not Enjoying Life More During the Healthy Years: I often have clients who look back and wish they had taken more time to enjoy life while they were still healthy and active. They regret not traveling more, trying new experiences, and making the most of their physical capabilities. Prioritizing joy and adventure when you can is crucial, as good health isn't guaranteed forever.

Underestimating Healthcare Costs and Neglecting Health and Wellness: Many retirees regret not planning sufficiently for healthcare expenses. Medical costs can be substantial and unexpected, often exceeding what was initially anticipated, which is something I help clients plan for and stay ahead of. Failing to maintain a healthy lifestyle during their working years is a regret to be mindful of. Poor health can limit mobility, independence, and overall quality of life in retirement.

Lack of Planning for Purpose and Engagement: Some retirees tell me they find themselves feeling aimless and unfulfilled because they did not plan for how they would spend their time. Having hobbies, volunteer work, or other engaging activities is crucial for a satisfying retirement.

Not Downsizing or Adjusting Living Arrangements Sooner: I've had clients who regret not moving to more suitable living arrangements earlier. Whether it's downsizing to reduce maintenance and costs or moving to a community with better amenities, timely adjustments can enhance your retirement and comfort.

I've seen firsthand how understanding these common regrets can really open up opportunities for making better choices in both your career and retirement planning. It's like having a roadmap from those who've been there and done that, helping you avoid some of the same pitfalls.

​Here are some actionable tips to takeaway from this conversation to steer clear of these regrets and set yourself up for a more satisfying journey:

Pursue Passion Projects: Whether it's a side hustle, a hobby, or a complete career change, integrating your passions into your work life can lead to greater satisfaction.

Balance Work and Personal Life and Seek Meaningful Work: Prioritize relationships and personal time. Set boundaries to ensure you're not sacrificing your personal life for career advancement. Don't be afraid to explore new career opportunities that align with your values and interests.
​
Plan Financially and Health-Wise for Retirement: Start saving early and plan for potential healthcare costs. Maintain a healthy lifestyle to ensure a vibrant and active retirement.

Engage in Purposeful Activities: Remember to enjoy life now while you are healthy and able to pursue experiences that you value.

​Remember, it's never too late to make positive changes. Whether you're early in your career, nearing retirement, or already enjoying your golden years, these insights can help you live a more balanced, happy, and rich life.

​Personal finance was my first love in the money world. I was a saver before I ever knew what investing even was. Yet my relationship with personal finance has evolved as I’ve aged and I've changed my habits as my views expanded.

Many of the personal finance rules written in stone will always apply and none of these should surprise you; live below your means, pay yourself first, stay out of credit card debt, save for emergencies.

However, after more than a decade as a Certified Financial Planner there are other personal finance commandments I don’t completely agree with anymore and I wonder if some of these might raise eyebrows:

Belief #1: Early Retirement Isn't for Everyone
While the idea of retiring in your 40s or 50s sounds appealing, it's not a one-size-fits-all solution. Early retirement requires extreme savings and frugality, often at the cost of enjoying your prime years. For many, the sacrifices needed to retire early might outweigh the benefits.

Instead of fixating on early retirement, consider aiming for financial flexibility. Build a career you enjoy, which allows you to work on your own terms. Embrace lifelong learning and adaptability. By focusing on financial freedom rather than an arbitrary retirement age, you can create a more fulfilling and less stressful life.

Belief #2: Debt Can Be a Useful Tool
The conventional wisdom is to avoid debt at all costs. While high-interest debt like credit cards can be detrimental, not all debt is bad. Leveraging debt can be a strategic move in building wealth. For example, taking on a mortgage to buy property can be a sound investment, if the value of the property makes sense with current interest rates. Similarly, using student loans to invest in your education can lead to higher earning potential.

The key is to differentiate between good and bad debt. Good debt, used wisely, can open doors to opportunities and financial growth. Bad debt, on the other hand, should be minimized and managed carefully. Understanding this distinction is crucial for making informed financial decisions.

Belief #3: It's Okay to Spend on What You Love
Frugality is often preached as a cornerstone of good financial health. I subscribe to living below your means. How else are you going to build wealth if you don’t spend less than you earn and save the difference? But most personal finance experts take this to the extreme. Life is meant to be enjoyed, and sometimes that means spending money on things that bring you joy. It's important to strike a balance between saving for the future and living in the present.

Don’t get me wrong — I’m still not a fan of wasting money. There are certain things I refuse to spend a lot of money on — the newest tech gadgets, luxury clothing, high-end furniture, etc. These things don't bring me joy. But there is stuff I enjoy spending money on. If you know me, you know experiences always offer a bigger bang for my buck. Brittany and I love to travel and this is a key part of OUR Rich Life. We cut back in other areas to spend focus our spending here, and that is okay, especially for this stage in our life together. 

By all means, save diligently and invest wisely. But don't deprive yourself of experiences or possessions that enrich your life. The key is mindful spending—prioritize what truly matters to you and cut back on expenses that don't. This approach can lead to a more satisfying and balanced life without the guilt of spending.

Belief #4: Personal Finance Is Personal
The most sacrilegious belief of all is that personal finance is, indeed, personal. What works for one person might not work for another. Your financial strategy should align with your values, goals, and circumstances. Giving clients peace of mind to enjoy their version of a Rich Life is always my goal. Don't be afraid to deviate from conventional wisdom if it doesn't suit your unique situation. After seeing clients pass away with millions of dollars in their accounts, I think about all the experiences they didn’t get to spend with their families at the expense of saving money. 

Seek advice, but ultimately, trust your judgment and tailor your financial plan to your life. Flexibility and adaptability are key to managing your finances effectively.

Belief #5: Moving the goalpost isn't always the goal.
The Wall Street Journal recently shared research on how much money people need to make to be happy: In the survey, most people said it would take a pretty significant pay bump to deliver contentment. The respondents, who had a median salary of $65,000 a year, said a median of $95,000 would make them happy and less stressed. The highest earners, with a median income of $250,000, gave a median response of $350,000.

Does this mean contentment is basically impossible to find? Regardless of how much you make, will you always want more? The goalposts just keep moving if we're not living in the present and and focusing on our values and circumstances. Spending on what brings us joy NOW and remembering that personal finance is PERSONAL are both antidotes to the discontent that can come from following the norm and checking the boxes we've been told to check.

Challenging conventional wisdom in personal finance isn't about dismissing sound advice—it's about recognizing that financial strategies should be as diverse as the people who use them. By questioning standard advice and embracing a more personalized approach, you can create a financial plan that truly works for you.

Remember, the goal is not just to save for retirement but to build a life that's financially secure and fulfilling at every stage, otherwise known as a Rich Life.

​I saw a chart this week from Bank of America that more or less sums up my entire investment philosophy:

In the long run, stock prices go up.
​
I view the stock market as a way to invest in innovation, profits, progress and people waking up in the morning looking to better their current situation. While I love the fact that this chart illustrates my long-term philosophy it’s a bit misleading. Yes, the stock market goes up over the long run but it can also get crushed in the short run. That can be difficult to see on a log chart with 200 years of data. The Great Depression, 1987 crash and Great Financial Crisis look like minor blips on this chart. And while every crash eventually turns into a blip on a long-term chart, they don’t feel like it in the moment. 

Looking at this chart got me thinking about what other visuals I would use to help explain the stock market in greater detail, so I found a few more.
​
You can’t look at an up-and-to-the-right chart of the stock market without taking into account the drawdowns along the way: