When Life Happens, Where Will the Money Come From?

Imagine an unexpected $5,000 repair bill during a week when your investment portfolio has already taken a hit. You have money invested for the future, but the bill needs to be paid now. Suddenly, a market decline that felt manageable has become a decision about what to sell.

That is where an emergency funding plan earns its place. Knowing where the money will come from can reduce the pressure to sell long-term investments at an unfavourable time. It can also make an unsettling market easier to live through.

The right arrangement will look different from one household to the next. Cash in a bank account, a money market fund held separately in your investment account, or a pre-existing line of credit may each have a role. What matters is how those resources would work in your circumstances.

Start with what could happen

A broken appliance versus several months without income create very different demands. One requires a payment. The other requires a way to keep paying for housing, groceries, childcare and existing debt while your usual paycheque is missing.

Before choosing an account or an amount, consider what your household would need to keep functioning. How much of your spending is essential? How dependable is your income? If you have two incomes, could the same event affect both?

A household with predictable earnings and room in its monthly budget will need a different arrangement from someone who is self-employed, earns commissions or supports a family on one income.

Give each source a clear job

Cash in chequing or savings is straightforward: it is money you already own and can generally access quickly. Keeping a portion separate from your everyday spending can help prevent it from gradually becoming part of the monthly budget. A savings account may also pay interest while the money waits.

A money market fund in an investment account can serve a similar behavioural purpose. The reserve is out of sight, while still set aside for a specific need. These funds hold cash and short-term debt securities, but they are investments. Check the specific fund and account, including how long selling units and transferring the proceeds to your bank account would take.

A pre-existing line of credit can provide a short-term bridge when an expense arrives before the money to pay it. For a household with dependable cash flow and a realistic repayment plan, that flexibility can be useful. One of the potential problems with the line of credit is that it also creates debt. Interest rates are generally variable, and making only the minimum payment may leave the balance outstanding. One thing that usually is not known about a line of credit is that a lender can demand repayment of a home equity line of credit at any point in time. If your plan depends on borrowing, understand those terms before you need the money. The practical question is how you would repay it if your income were interrupted. Borrowing to handle a temporary timing gap is a different commitment from borrowing every month to cover ongoing living costs.

A combination may fit your life

You do not have to choose just one approach. You might keep enough in a bank account for immediate expenses, hold an additional reserve in a money market fund, and retain an unused line of credit as another option. Each part should have a purpose, with a clear order for using it.

Walk through the plan before relying on it. If a major bill arrived tomorrow, what would you use first? If your income stopped for several months, what would change? If you borrowed, what money would repay the balance, and when?

“I will repay it when markets recover” leaves too much outside your control. A recovery has no dependable deadline, while interest and household bills continue to arrive.

Make room for the unexpected

Holding a reserve has a tradeoff: money kept readily available may earn less than investments chosen for long-term growth. This “cost of comfort” deserves consideration alongside the flexibility the reserve provides. Its value includes giving you more choice when life becomes expensive at an inconvenient time.

This is why I see emergency funding as part of the financial plan and the investment conversation together. The way you cover short-term needs affects how confidently you can commit money to longer-term goals.

You cannot choose when the next unexpected expense will arrive or what markets will be doing that day. You can decide in advance how you would respond. Does your backup plan fit your life—and would it work when you actually need it?

Jesse Ogloff, B.Comm, PFP, CFP, CIM, CFDS

Associate Wealth Advisor / Associate Portfolio Manager

CIBC Wood Gundy


Healthy Income, Zero Strategy: The Mistake Young Professionals Make

There is a stage of life when the things you worked toward begin arriving together.

Your career is gaining momentum. Your income is growing. A relationship becomes a shared future, and conversations turn toward marriage, buying a home, or starting a family.

After years of education and putting things off, you also want to enjoy yourself. Take the trip. Find a place with more space. Have a little breathing room.

Yet alongside that progress comes a feeling you might not have expected: you are earning more than ever, but you are still unsure whether you are getting ahead.

That is understandable. A growing income creates possibilities. Deciding how those possibilities fit together takes some thought.

For many young professionals, financial complexity arrives well before a large investment portfolio does.

There may be student debt to repay, a down payment to build, and investments to start. At the same time, you and your partner may be considering what parental leave would mean for your household, how much home you would feel comfortable carrying, or whether one of you might eventually work less.

Depending on your career, questions about partnership, self-employment, or incorporation may arise, too.

Each decision deserves attention. And each one affects the room you have for the others.

A larger mortgage changes what you can save. An aggressive debt repayment schedule can leave less cash available for an upcoming life change. A career move may offer greater long-term opportunity while making income less predictable in the meantime.

You can make a series of individually reasonable decisions and still find yourself with a financial life that feels stretched.

Consider a young professional who has recently moved into a higher-paying role. Their partner is also working, and together they feel ready to buy a home. They still have education debt, would like to start a family within a few years, and want to begin investing more seriously.

There is nothing unusual about those goals. The challenge is that the same dollars are being asked to support all of them.

Before choosing a monthly investment contribution or a house budget, it helps to understand the whole picture. What would their finances look like during parental leave? How much flexibility would they want afterward? Which commitments would still feel comfortable if their plans changed?

Those conversations give the numbers meaning. They help a couple decide what they are comfortable committing to and what they would prefer to leave open.

This is where planning earns its place.

A useful financial plan connects where you have been, where you stand today, and what you want your future to look like. It takes account of the commitments you already carry, the habits you have developed, and the people who depend on you.

It also makes room for questions that do not have purely mathematical answers.

How important is owning a home soon? What would make you feel financially secure enough to change jobs? How much do you want to enjoy today, and what are you willing to set aside for later?

The answers will be different for every household. They may even be different for two people living in the same household. Getting those priorities into the open is part of the work.

A good income can make these conversations easier to postpone. There is a natural temptation to assume that the next raise will create the breathing room, or that serious planning can begin once there is more money invested.

But as income grows, commitments can grow with it. A few larger recurring expenses can absorb much of the increase before you have consciously decided what you wanted it to accomplish.

That does not mean every raise needs to be saved or every purchase needs to be justified. Enjoying the life you are building belongs in the plan, too.

The aim is to make those choices deliberately, with an understanding of what they mean together. Sometimes that means saving more. Sometimes it means giving yourself permission to spend. Sometimes it means slowing down one goal to protect another that matters more.

You do not need to know exactly what the next twenty years will look like to begin. You need a clear starting point, sensible priorities, and a process for revisiting decisions as life changes.

Your career will evolve. Your family may grow. What feels important at thirty may look different at forty. Planning gives you a way to respond thoughtfully along the way.

A strong income is a valuable opportunity. Turning it into lasting security, flexibility, and a life you enjoy takes ongoing attention.

If you are earning well and wondering whether it is translating into progress, that is a worthwhile place to start a conversation.

You do not have to wait until you have accumulated substantial wealth to think carefully about the life you want it to support.

Jesse Ogloff, B.Comm, PFP, CFP, CIM, CFDS

Associate Wealth Advisor / Associate Portfolio Manager

CIBC Wood Gundy


Why Markets Can Rise Through Uncertainty

Making investment decisions when the headlines feel unsettled

You open the news and find another reason to be cautious. Borrowing costs are rising. Energy is more expensive. A conflict overseas threatens to reach further into everyday life. Then you look at the market and wonder how share prices can remain so close to their highs.

Perhaps you have money waiting to be invested. Perhaps retirement is approaching, and you are thinking about protecting what you have built. Either way, the thought is understandable: would it be better to wait until things settle down?

The difficulty is deciding what settled would look like. There will always be something unresolved. A financial plan needs to give you a way to make decisions while those questions remain open.

Despite higher oil prices, rising bond yields and tighter monetary policy, currently the S&P 500 is less than 1% below its August 13th record high as of September 22nd. The US economy has continued to be resilient and corporate earnings continue to be healthy and growing.

That resilience deserves attention. Understanding it begins with remembering what you own when you invest in shares of the great companies of today: a claim on a business and its future profits. The news matters because of what it might change about those profits in the future, and about the price investors are willing to pay for them.

A company can face higher costs and still earn more if demand for its products remains strong. A difficult outcome can also be less damaging than investors expected. Prices reflect expectations, so an alarming development does not automatically produce an equally alarming market response.

This helps explain why following the news closely can still leave you surprised by your portfolio. Identifying a problem is only part of the work. You also need to understand its likely effect, how long it may last and how much concern is already reflected in prices.

Higher interest rates offer a useful example. Their impact depends partly on who needs to borrow and when. A business with fixed borrowing costs for several more years faces a different situation from one that must refinance next month. The same increase in rates can reach different balance sheets at very different times.

Energy prices require similar care. A brief increase and a prolonged period of higher costs can have very different consequences for household spending and business profits. Lower energy intensity and the relatively small share of household income spent on gasoline entering the year have acted as buffers against the shock of higher energy prices.

None of this makes higher rates or expensive energy harmless. The effects can build over time. Strong earnings can weaken, and investors can discover that they were too optimistic. A market holding near its highs tells us how investors have responded so far. It cannot promise what happens next.

That is why I would be careful about turning this discussion into a reason to take on more risk in your portfolio. The useful question is what your own finances can support through a range of outcomes.

Consider two families with the same investment balance. One expects to use a substantial portion for a home purchase next year. The other is saving for retirement twenty years away. They can read the same economic news and reasonably make different decisions. Their money has different responsibilities.

Begin with those responsibilities. What will you need to withdraw, and when? How much flexibility do you have if markets decline? Would a difficult year force you to sell investments to meet expenses? The answers help determine how much belongs in cash and other more stable holdings, and how much can remain invested for longer-term growth.

Then review whether your portfolio still fits. A strong market may have increased your exposure to equities beyond the level you intended. Rebalancing can restore that balance without requiring a forecast. A change in your income, spending or retirement date may also justify an adjustment. Those are concrete reasons to revisit a plan.

If you are waiting to invest because the news feels unsettling, be specific about what would change your mind. Lower prices may arrive alongside worse headlines. Better news may arrive after prices have already risen. Without a clear decision process, waiting can become an open-ended position of its own.

You do not need to feel comfortable with every headline to make a considered decision. You do need to understand the risks you are taking and how they fit the life your money is meant to support.

You worked hard to build this wealth. Give it a plan that leaves room for uncertainty, with enough stability for the commitments ahead and enough patience for the goals that will take time.

Jesse Ogloff, B.Comm, PFP, CFP, CIM, CFDS

Associate Wealth Advisor / Associate Portfolio Manager

CIBC Wood Gundy


Strategic Gifting

Giving to adult children with purpose, clarity and a plan.

You watch your adult child do the things you hoped they would. They work, save, care for their family and try to build a life of their own. Still, there is very little room left at the end of the month. Meanwhile, you look at what you have accumulated and wonder whether some of it could be doing more for them today.

Then another thought follows: if you help now, what happens later? Will they become more independent? Will their siblings understand? Will you still have enough? These questions deserve a place in your financial plan. They reveal what the money means to you, and what you hope it will make possible for the people you love.

Think of a gift as helping lay a foundation. Its value depends on what it supports. A contribution toward education, a manageable first home or a difficult period of childcare can help your child build something lasting. The same amount, offered without a clear purpose or expectations, can leave everyone unsure of what comes next.

Before deciding how much to give, ask yourself: what do I hope will be different in my child’s life because of this money? You must be specific. Perhaps you want them to finish a qualification without taking on more debt. Perhaps you want to ease the pressure during parental leave. Perhaps you want to help with a down payment while leaving the ongoing cost of homeownership firmly within their means. That purpose gives you a way to judge whether the help is working.

The time of the gift matters as well. An inheritance received late in life may arrive after the years when housing, young children and career demands placed the greatest strain on a family. An affordable gift earlier on may create choices when they are particularly valuable. You also get to see what your generosity makes possible. There is no obligation to give early, however. Keeping resources available for your own life is a valid decision. Your financial security is part of the foundation your family relies on.

An account balance alone cannot tell you what you can afford to give. Those assets may need to support decades of spending, rising costs, future care and the surviving spouse’s needs. Travel, charitable commitments and the freedom to make your own choices belong in that calculation as well.

This is where planning earns its place. Compare the effect of a gift today with smaller gifts over time or a transfer through your estate. Test those choices against weaker investment returns, higher spending and a longer life. Allow room for outcomes that do not follow the forecast. No projection creates certainty, but it can show which promises your finances are better equipped to support.

If a gift only works when markets perform especially well, reconsider the amount or timing. Increasing investment risk to make a gift affordable introduces another vulnerability into the family’s plan.

Once you understand your capacity, the conversation becomes more useful. If you have a partner, begin together. One of you may see support as an opportunity; the other may worry about dependence. Discuss what each of you hopes to protect before making a commitment to your children.

Then make the expectations explicit. Is this a one-time gift? Will there be further help? Is repayment expected? Does it affect a future inheritance? Ask your child what would actually help, too. Their priorities may differ from the ones you have imagined.

You also need to consider how much influence you expect the money to buy. If you would be upset by a particular use of the funds, discuss that before giving. An unspoken condition can turn gratitude into tension long after the transfer has cleared.

Fairness requires the same care. Equal amounts offer one clear approach, but your children may have very different needs. One may require ongoing support because of a disability. Another may need temporary help following a separation. You can acknowledge those differences while still treating each child with dignity.

Explain the principles behind your decisions without disclosing another child’s private circumstances. If you intend to account for earlier gifts in your estate, have the approach properly documented and review it over time. Future care costs, spending and investment results may change what remains available. A promise to balance everything later needs more than good intentions.

The practical details should serve these decisions. For a typical cash gift between a Canadian parent and adult child, the child generally does not report the gift as taxable income. But raising the cash may create a tax bill for the parent. Ordinary RRSP withdrawals are generally taxable, and transferring investments that have increased in value can trigger a capital gain based on their fair market value.

A gift toward an eligible child’s First Home Savings Account can also be useful, provided they have contribution room. You give them the cash and they contribute to their own FHSA. The eligible tax deduction belongs to your child. It does not become your deduction because you supplied the money.

Be equally clear about whether the support is a gift or a loan. If repayment or protection matters, ask a lawyer to put the appropriate arrangement in place before money changes hands. For substantial transfers, especially toward property, obtain advice on documentation and the applicable provincial family-law rules.

You do not need to solve every question at once. Start by writing down what you want the help to achieve. Review what your own plan can support, agree on the expectations and choose the structure that fits. A smaller, well-considered commitment can be a meaningful place to begin.

You spent years building a foundation for your family. Giving thoughtfully allows you to extend it, with enough strength left to support your own life as it changes. That is a worthwhile purpose for the wealth you have worked so hard to create.

Jesse Ogloff, B.Comm, PFP, CFP, CIM, CFDS

Associate Wealth Advisor / Associate Portfolio Manager

CIBC Wood Gundy


Mid-Year [2026] : Staying Focused When Markets Give Us Plenty to Watch

As we reach the halfway point of 2026, it’s tempting to judge the year by its headlines like geopolitical conflict in the Middle East, questions around inflation, interest rate speculation, and artificial intelligence dominating technology stocks. Record highs in some markets while others quietly outperformed.

If it feels like there’s been no shortage of reasons to worry, you’re right. Yet despite everything that’s happened over the past six months, global markets have continued moving higher. That may seem surprising at first—but history suggests it shouldn’t.

One of the greatest misconceptions in investing is believing markets wait for certainty before moving forward. In reality, they rarely do. Markets continuously absorb new information, adjust expectations, and move on long before the news cycle does. That’s why successful investing has never been about predicting the next headline. It’s about having a plan that doesn’t depend on predicting headlines at all.

The Story Behind the Numbers

The first half of the year has been a reminder of just how unpredictable markets can be. The S&P 500 reached new highs after stumbling earlier this spring as investors reacted to geopolitical tensions. Technology companies rebounded strongly, while emerging markets quietly became one of the year’s strongest performers. Meanwhile, many investors who expected gold to provide protection during global uncertainty actually saw it lose value during the conflict, while equities continued climbing. 

Perhaps the biggest lesson isn’t which investment performed best. It’s that it is nearly impossible to predict these outcomes. Every January, financial institutions publish forecasts identifying the sectors, countries, or asset classes they expect to lead. By June, those predictions are often forgotten because markets had other plans. The first half of 2026 was another reminder that leadership changes quickly. Trying to guess tomorrow’s winners often means missing today’s opportunities.

Why Diversification Still Matters

Over the past five years, international value stocks have quietly outperformed many of the areas investors have spent the most time talking about. That’s important because it reinforces a lesson that doesn’t get enough attention: The best-performing investments are often the ones receiving the least attention. No one consistently knows whether the next five years will belong to U.S. stocks, international markets, emerging economies, large companies, or smaller businesses. Because we don’t know, we don’t try to guess. Instead, we build globally diversified portfolios designed to participate wherever opportunities appear. Diversification isn’t exciting. But investing rarely rewards excitement.

Interest Rates, Inflation and the Questions Everyone Is Asking

Another common question this year has been: “When will interest rates come down?”

The honest answer is that nobody knows. The Federal Reserve (US) and The Bank of Canada have continued holding rates steady while inflation remains stubbornly above target and economic data continues sending mixed signals. Markets have repeatedly adjusted expectations for future rate cuts. This is another reminder that markets price in expectations almost instantly. By the time news becomes obvious, markets have usually moved ahead. Rather than trying to predict central bank decisions, we focus on building portfolios that can weather a wide range of economic environments.

Investing Isn’t About Winning This Year

One of my favorite reminders is that none of us are investing for 2026. We’re investing for retirement, for children’s education, for buying a home, for financial independence, for the ability to spend more time with family.

Markets will always have good years, disappointing years, and years that feel confusing. Your financial plan shouldn’t require you to predict which one comes next. Instead, it should provide confidence that you’re making steady progress toward goals that matter regardless of what the market does this month. That’s why every recommendation we make starts with your life—not with the market.

Time Is the Advantage Most Investors Underestimate

Many people believe successful investors have superior forecasting abilities. In reality, they often have superior patience. Markets reward those who remain invested through uncertainty. Every correction, every geopolitical event, every recession, and every recovery has reminded us of the same lesson: temporary uncertainty is the price investors pay for long-term growth. Trying to avoid every decline usually means missing many of the strongest recoveries.

As Nobel Prize-winning economist Paul Samuelson once said: “Investing should be more like watching paint dry or watching grass grow.”

It’s not supposed to be exciting. It’s supposed to work.

Looking Ahead

No one knows what the second half of 2026 will bring. There will almost certainly be more headlines that make investors uncomfortable because there always are. What gives me confidence isn’t knowing what’s coming next. It’s knowing that successful investing has never depended on knowing what’s coming next. It has depended on having a thoughtful financial plan, maintaining a diversified portfolio, controlling the things we can control, and allowing time to do the heavy lifting. That’s exactly what we’ll continue doing.

Thank you, as always, for trusting me to be part of your financial journey.

Have a wonderful summer,

Jesse Ogloff, B.Comm, PFP, CFP, CIM, CFDS

Associate Wealth Advisor / Associate Portfolio Manager

CIBC Wood Gundy


The Hidden Tax Layer in Your Portfolio

Why Where Your ETF Lives Matters More Than You Think

Most investors spend their time deciding what to invest in. S&P 500 or global? Growth or value? Active or passive? But there’s a quieter question—one that rarely gets asked: Where does your investment actually live? Because when it comes to ETFs, location isn’t just geography… it’s taxation. And depending on how your portfolio is structured, that tax can either be minimized—or quietly compound against you for decades.

What Is an ETF (And Why Most Investors Use Them)?

An ETF (Exchange-Traded Fund) is a basket of investments that trades on a stock exchange—just like a single stock. Instead of buying one company, you’re buying hundreds or even thousands at once. For example, an ETF tracking the S&P 500 gives you exposure to companies like Apple Inc., Microsoft Corporation, and Amazon.com Inc.—all in a single purchase. Some of the benefits of ETFs are broad diversification, low cost, and simple & scalable exposure to global markets. But one issue is that two ETFs can look identical on the surface but can produce different outcomes, simply because of how they are structured or where they are domiciled.

The Structural Difference: U.S. vs Canadian-Domiciled ETFs

A U.S.-domiciled ETF (like VTI or VOO) is listed in the U.S. and holds underlying US securities directly. A Canadian-domiciled ETF (like XUU or VFV) is listed in Canada and provides U.S. exposure inside a Canadian fund structure. They may track the same index and they may hold the same companies but the tax treatment is not the same—especially depending on which type of account you use.

The Tax You Don’t See: U.S. Withholding Tax

When U.S. companies pay dividends to Canadian investors, the U.S. government applies a 15% withholding tax. This is where account type starts to matter.

TFSA: Tax-Free… But Not Fully Efficient

The Tax-Free Savings Account is one of the most powerful tools Canadians have but when it comes to U.S. investments, there’s a limitation. The issue is that, for Canadians, U.S. dividends are subject to 15% withholding tax and this taxation within a TFSA is not recoverable. This means that if your ETF generates $1,000 in dividends, you lose $150 permanently.

RRSP: The Cross-Border Sweet Spot

The Registered Retirement Savings Plan is where cross-border planning starts to work in your favor because of the Canada–U.S. tax treaty, the IRS recognizes RRSPs as retirement accounts. The result is that there are no U.S. withholding tax on dividends from U.S. domiciled ETFs, which results in you receiving the entire dividend. So, if your ETF generates $1,000 in dividends → you keep the full $1,000. It is very important to note that this benefit only applies to U.S.-domiciled ETFs. If you use a Canadian domiciled ETF that provides U.S. exposure, the withholding tax is applied inside the fund—and you don’t see it.

Non-Registered Accounts: Not Perfect, But Recoverable

A non-registered account doesn’t avoid withholding tax upfront—but it does give you a mechanism to recover it. As a Canadian, you still are required to pay the 15% withholding tax but you receive a foreign tax credit when you file your Canadian tax return. This results in your avoiding double taxation but you still have to pay Canadian income tax on the income that you earn.

So… What Should You Actually Do?

This isn’t about chasing perfection. It’s about being understanding your investments and being intentional with placement. Use your non-registered account with awareness of tax reporting and structure. Use your RRSP for U.S.-domiciled ETFs when appropriate. Use your TFSA for Canadian equities or growth-focused investments with lower dividend yield

Final Thought

Most investors don’t fall short because they chose the wrong ETF. They fall short because of unnecessary tax drag, reactive decisions during volatility, or a lack of structure behind their portfolio. This is one of the rare areas where a small adjustment can create a permanent tailwind for your NET returns.

Take 15 minutes this week and ask:

  • Where are my U.S. investments currently held?
  • Am I unintentionally losing withholding tax in my TFSA?
  • Is my RRSP positioned to take advantage of the tax treaty?

You don’t need to overhaul everything overnight but tightening the structure—even slightly—can improve outcomes for decades to come.

Jesse Ogloff, B.Comm, PFP, CFP, CIM, CFDS

Associate Wealth Advisor / Associate Portfolio Manager

CIBC Wood Gundy


Improve Your Life By Spending With Intention

One of the most powerful financial concepts has nothing to do with stock picking, market timing, or complex strategies. It’s simply understanding what today’s spending could become if it were invested and allowed to compound and grow over time.

This isn’t about guilt or deprivation, it’s about awareness and intentionality. You should choose to spend money on things that truly improve your own life, while minimizing spending on things that don’t. Everyone is going to have a different answer to what truly brings them joy. It may be the daily coffee, the game on their phone, or spending quality time with the people that we care about. The point of the exercise is to determine what it is for you.

Small amounts may not feel meaningful in the moment, but over long periods of time, they can grow into surprisingly large numbers. At a 10% annual rate of return, money roughly doubles every 7–8 years. To illustrate this, let’s look at what common everyday expenses might be worth 30 years from now, assuming a 10% annual compound rate of return.

A $10 coffee doesn’t feel significant and for many people, it’s a daily ritual they genuinely enjoy. Invested instead, that same $10 could grow to approximately $175 over 30 years. This isn’t a suggestion to give up coffee. It’s simply a reminder that even small, recurring expenses have an opportunity cost and it’s worth understanding what that cost is. Would you still buy the coffee every day if you thought of it like you were spending $175 when you got to the counter?

A $100 dinner with friends or family can be money very well spent if it creates memories and enjoyment. From a purely financial perspective, that $100 could grow to about $1,745 over 30 years if invested. Sometimes the experience is worth far more than the future value and that’s perfectly okay.

A $1,000 purchase may feel like a one-time, justified expense. Left invested for 30 years at 10%, that same $1,000 could grow to roughly $17,449. Larger discretionary purchases naturally carry larger opportunity costs, which is why being intentional matters most when spending more.

One-time purchases are easy to evaluate. Habits are where the real impact occurs — because repetition plus time is where compounding truly shines. Here are two examples, using the same expenses above for a daily coffee during the work week and a weekly restaurant bill.

For our first example, let’s assume that you purchase a $10 coffee, 5 days per week, every week of the year. Let’s assume that you do this over the course of your 30-year career. This would work out to $2,600 per year that you’ve spent on coffee. If that $2,600 were invested annually instead, over 30 years it could grow to approximately $427,000. That number surprises many people, not because coffee is “bad,” but because consistency matters far more than size. If your daily coffee is something you genuinely enjoy and look forward to, it may be money well spent. If it’s simply a default habit, this is where awareness can make a meaningful difference.

Our second example assumes that you treat yourself to a once per week restaurant dinner, where you spend $100. That equals $5,200 per year spent on restaurant meals. Invested instead, over the course of 30 years, that annual amount could grow to roughly $855,000 over 30 years. Dining out can be about connection, convenience, and enjoyment — all valid reasons to spend money. The key question isn’t “Should I spend this?” It’s “Is this spending aligned with how much value it adds to my life?”

This exercise is not about cutting all enjoyment from your life or optimizing every dollar. It’s about recognizing that small amounts add up over time, understanding the opportunity cost of habits, and making conscious decisions about where your money goes. If something brings real joy, meaning, or convenience then spend confidently.

The goal is to reduce spending on things that don’t actually improve your quality of life, and redirect those dollars toward long-term investing or things in your life that personally bring you joy. We rarely regret spending money on things we truly enjoy. We often regret the money that disappeared without meaning. Understanding what today’s spending could become tomorrow gives you clarity, not restriction. Awareness leads to control, control leads to better choices and better choices compound, just like investments do.

Jesse Ogloff, B.Comm, PFP, CFP, CIM, CFDS

Associate Wealth Advisor / Associate Portfolio Manager

CIBC Wood Gundy


Appendix :

Assumes a 10% annual compound rate of return over 30 years

Amount Spent TodayFuture Value in 30 Years
$10~$175
$100~$1,745
$1,000~$17,449

Habit-Based Examples (Annual Investing):

  • $2,600 per year (daily coffee): ~$427,000
  • $5,200 per year (weekly restaurant): ~$855,000

Returns are illustrative only and not guaranteed.

Guiding Through Life’s Transitions: Announcing My CFDS Designation

Divorce is one of life’s most difficult transitions — emotionally, personally, and financially. Having guided families through life’s many milestones, I’ve often seen how uncertainty about the financial impact of separation can add an extra layer of stress during an already challenging time.

That’s why I’m proud to share that I’ve earned the Chartered Financial Divorce Specialist (CFDS) designation through the Academy of Financial Divorce Specialists — a certification that deepens my ability to help individuals and families navigate the financial complexities of divorce with clarity, fairness, and empathy.

What Is a CFDS?

A Chartered Financial Divorce Specialist is a financial professional — often a planner or accountant — who has specialized training in divorce-related financial analysis. CFDS professionals work with clients (and often their legal teams) to evaluate the short- and long-term implications of proposed settlements, including:

•           Division of property, pensions, and investments

•           Tax implications and income planning

•           Household budgeting and lifestyle sustainability

•           Child and spousal support scenarios

•           Retirement and long-term financial projections

By using specialized software and forecasting tools, a CFDS can model different scenarios to help clients see not just what a settlement looks like today, but how it may affect their future 5, 10, or 20 years from now.

Why This Matters

Divorce can feel like standing at a crossroads — uncertain which path leads to stability and peace of mind. The right financial guidance can make all the difference. My goal, as both a Certified Financial Planner (CFP) and now a Chartered Financial Divorce Specialist (CFDS), is to bring understanding and balance to these complex moments, ensuring decisions are made with both logic and compassion.

Whether it’s protecting future retirement goals, maintaining a home, or rebuilding financial confidence after separation, my role is to help clients see the full picture — and make decisions that support their long-term wellbeing.

Integrating CFDS Into My Practice

My philosophy has always been about treating financial planning like wellness — caring for your financial health through every stage of life. With the CFDS designation, I can now extend that same philosophy to clients navigating divorce, providing the same trusted, goals-based advice — but through a lens of fairness, foresight, and emotional understanding.

If you or someone you know is going through a separation and feels uncertain about the financial implications, know that there are compassionate, specialized professionals who can help.

Life doesn’t move in straight lines. Relationships evolve, families change, and financial plans must adapt. My commitment remains the same: to provide clarity, empathy, and expertise — no matter where you are in life’s journey.

Jesse Ogloff, B.Comm, PFP, CFP, CIM, CFDS

Associate Wealth Advisor / Associate Portfolio Manager

CIBC Wood Gundy

Your Role as a River Keeper : Responsible Stewardship of Your Family’s Wealth

How do you think of your wealth? Do you see it as a dollar value on a screen or something alive and evolving over time.

I encourage clients to think of their wealth as a river – flowing, dynamic, and shaped by generations. Your river may have begun long before you were born, fed by the work and values of those who came before you, or perhaps it began as a small spring during your own lifetime.

Either way, this river – your river – can continue far beyond where we stand today, if it is cared for and tended with intention.  

Headwaters : The Source of Your Wealth

Every river begins with a spring. For many families, that spring was created by the grit and discipline of earlier generations – parents, grandparents, or even great-grandparents who laid the foundation for everything that flows downstream.

Today’s river, carries not only your financial capital but also the beliefs, habits, and stewardship from your family story. Recognizing these headwaters helps guide your financial decisions with gratitude and perspective.

Tending the River in Your Stewardship Today

Being a river keeper is an immense responsibility. It means acting with purposeful intent to keep the waters clear, balanced, and flowing.

Here’s how :

Remove debris – Protecting your wealth from hidden risks : excessive fees, unmanaged taxes, and unnecessary expenses.

Strengthen the banks – Build safeguards like insurance, wills, and trusts to protect the structure of your financial ecosystem as it moves downstream.

Test the waters – Monitor your financial health, income streams, and spending patterns to ensure your river remains sustainable and high quality.

Being a river keeper isn’t about control – it’s about balance. Your job is to protect the river’s strength while allowing it to nourish the present.

Thinking Downstream : Planning Ahead

The best river keepers stay mindful of today’s conditions but always think downstream. They don’t just react to problems – they anticipate them.

Proactive tax planning, smart estate structures, and thoughtful investment strategies are the tools that will prevent blockages long before they appear.

In Indigenous Culture, the Seventh Generations Principle teaches that the choices we make today affect those seven generations after us. In the same way, you stand as the bridge between your ancestors’ resilience and your descendants’ future.

The Future of Your River

Eventually, your stretch of the river will end – and what happens next is up to you.

Some people choose for their river to flow outward into the ocean, supporting communities and causes through philanthropy. Other’s pass the current on to their children – perhaps as one simple, powerful stream, or one that splits into multiple branches to nourish several new paths.

Whatever form it takes, your river’s future depends on how you guide it today.

Becoming a Responsible River Keeper

Your role as a river keeper isn’t just to manage the flow – it’s to teach others how to do the same.

Just as a carpenter must apprentice before becoming a journeyman, the next generation must learn how to tend to the river : how to prevent blockages, strengthen the banks, and prepare for unseen bends ahead.

If you only focus on growing your wealth but neglect to pass on the wisdom of stewardship, the river’s current may one day run dry.

I make sure that I work with the younger generations of my clients, no matter what stage of life that they may be in, to ensure that they are learning and are equipped with all of the necessary tools for their situation today and for their future.

So remember the Seventh Generation Principle – your river began before you and, with care, will flow long after you. The question isn’t how much can you take from it – it’s how will you tend to it for those who will come next.

From Panic to Euphoria : Where Are You On the Investing Roller Coaster of Emotions?

Markets are once again flirting with all-time highs. For some investors, it feels like the thrilling climb of a roller coaster. For others—especially those still recovering from recent dips—it feels like that slow, anxiety-inducing ascent before the next big drop. But here’s the truth: volatility is not the enemy. It’s part of the ride.

Whether the market is setting new records or pulling back, short-term moves are never the full story. What matters isn’t where we are in the cycle—but how you behave throughout it.

The Market Has Seen This Before

Despite numerous bear markets over the last century—including the crash of 2008, the COVID drop of 2020, and the tech wreck of the early 2000s—markets have always rebounded. Always.

– The 2008–09 crisis saw the S&P 500 fall 57%… and then double in the 48 months that followed.
– The 2020 COVID crash bottomed in March—and by the end of the year, the S&P was up 16%.
– Even in the brutal 2000–02 bear market, investors who stayed the course were rewarded once the dust settled.

Every single bear market has been followed by a bull market. The real challenge isn’t predicting the recovery—it’s staying invested long enough to experience it.

Where Are We Emotionally?

Take a look at the chart below from Russell Investments: The Market Cycle of Emotions.

Right now, many investors are likely hovering between relief and optimism. We’re past the fear and panic of 2022–23, and as portfolios start looking healthier, the temptation to second-guess your plan may creep in:

– “Should I sell while I’m up?”
– “Maybe I should wait for a pullback?”
– “Have we come too far, too fast?”

This kind of emotional second-guessing is exactly what derails long-term outcomes.

Remember: euphoria is the point of maximum financial risk, while despondency is the point of maximum financial opportunity. Most investors act in reverse—buying high and selling low—because they’re reacting to feelings instead of following a plan.

If you want to reach your destination, you need to stay in your seat through the highs and lows. Unbuckling mid-ride rarely ends well.

Volatility isn’t just about losses—it’s also the unpredictability of gains. The biggest up-days in market history often happen during periods of uncertainty, and they tend to cluster closely around market bottoms.

Missing just a few of those days can drastically lower long-term returns. That’s why trying to time the market is more dangerous than staying invested through the rough patches.

Time In The Market > Timing The Market

The most effective investors don’t try to sidestep volatility—they prepare for it. They diversify. They rebalance. They stay invested according to their goals, not their fears.

Whether you’re still accumulating wealth or already in retirement, the key is to have the right money in the right place:

– Long-term investments should stay invested.
– Short-term income needs should be allocated to safer, more stable assets.

This kind of “time segmentation” allows you to stay calm during downturns, knowing your immediate needs are covered while the rest of your money grows.

Final Thoughts : The Real Superpower

Market highs tend to bring out two common emotional mistakes:
1. Chasing (jumping in too late, driven by FOMO), or
2. Fleeing (selling out too early, afraid the top is in).

Avoid both.

The real superpower isn’t predicting tops or bottoms—it’s sticking to your plan through all the emotional highs and lows. Diversification, discipline, and time are your greatest allies. And they work best when you don’t get in their way.

For personalized guidance, contact me at info@financerx.ca.