So You are Retired but You Can't spend your Money

I’ve seen it time and again: folks who’ve spent their lives pinching pennies, building a tidy nest egg, only to clutch it tighter than a drum when it’s time to actually enjoy it. My former Sales Coach, for example, told me he can’t get his sister-in-law and her husband to take a family trip. They’re 75, sitting on a cool $2 million in savings—enough to live comfortably for decades.

“We invited them on a bucket-list trip to Moab, a $10,000 adventure to soak in red rock vistas and make memories. Their response? A flat “no.” Why? A $2,000 home repair was looming, and they needed to “conserve.” For what, exactly? Another rainy day that might never come?”

I was asked to write an article about this theme - retirees who can not spend when they have the wealth to do so. I share this psychology so it is close to my heart.

This isn’t just my in-laws. It’s a pattern. People who’ve saved diligently—sacrificing small joys, skipping vacations, buying the off-brand cereal—hit retirement and can’t flip the switch. They’ve wired their brains for scarcity, not abundance. The fear of running out, of not having enough, lingers like a ghost, even when their bank accounts scream security.

Andrew Wilkinson, the entrepreneur behind Tiny, nails this mindset in his candid takes on wealth. He’s written about how money can become a trap, not a tool. You grind, you save, you amass—and then you’re paralyzed, unable to spend on what matters because you’re still playing defense. My Sales Coach’s in-laws aren’t worried about the $10,000 for Moab; they’re worried about the idea of spending. That $2,000 repair isn’t the issue—it’s a symbol of every “what if” they’ve ever imagined. What if the market crashes? What if they need a new roof? What if, what if, what if.

Here’s the kicker: this isn’t about logic. It’s psychology. Decades of saving form habits that are hard to break. Spending, even on something as life-affirming as a trip with family, feels like a betrayal of the discipline that got them there. Wilkinson’s talked about this with his own journey—how building wealth can make you obsessive, not free. You start seeing every dollar spent as a dollar lost, not a dollar traded for joy, experiences, or connection. The data backs this up. A 2023 study from the Employee Benefit Research Institute found that retirees with over $2 million in savings often spend less annually than those with half as much. Why? Fear of outliving their money, even when the math says it’s impossible. My Sales Coach’s in-laws could spend $50,000 a year on top of their current lifestyle and still not dent their principal. But try telling that to someone who’s spent 50 years equating spending with danger.

So, how do you break the cycle? It’s not easy. Wilkinson’s approach—focus on what money can do for you, not what it is—is a start. For Bill’s in-laws, I’d love to see them reframe that Moab trip not as a $10,000 expense, but as a chance to laugh with their kids, feel the desert sun, and make stories they’ll carry to the end. It’s about shifting from a mindset of “saving for later” to “living for now.” Start small. Budget for joy—whether it’s a trip, a nice dinner, or a gift for someone you love. Set a “fun fund” and commit to spending it, no guilt allowed.

Talk to a financial advisor to run the numbers and prove you won’t end up destitute. For Bill’s in-laws, he could show them the math: their $2 million, conservatively invested, could throw off $80,000 a year without touching the principal. Moab’s a drop in the bucket. Life’s short, especially at 75. Money’s a tool, not a trophy. Don’t let it keep you from the views in Moab—or whatever your version of that is. Because if you’re saving for a “what if” that never comes, you’re not saving. You’re just missing out.

Jacoline Loewen is an UHNW Relationship Manager in wealth management and an author who helps people navigate the emotional and practical sides of money. Follow her for more no-nonsense takes on building a life you love, not just a bank account.

Wealth Management Isn’t Just Numbers

I’ve spent decades guiding wealthy families, and here’s the truth: money amplifies everything—love, greed, resentment. Newly rich founders, fresh off selling their business, come to me thinking wealth management is about investments. Wrong. It’s about saving your kids from a black hole.

Moms say, “My kids are great and they love each other. They’ll share fairly.” I smile, but I’ve seen too many families torn apart after the parents are gone. Siblings bickering over cottages, trust funds, or who “deserves” more? That’s what happens when you kick the can down the road for your children to fight battles in their fifties. What is this can? Governance for the family wealth and inheritance needs to be put in place to ensure worst-case scenarios are prevented.

Founders, you’re the worst offenders. You clawed your way up—sleepless nights, maxed-out cards, pure grit. Your kids? They’re growing up with private schools, St Barth’s and Whistler ski trips, and quite frankly, surrounded by people who now know they have access to money. You want them to have your hustle, but you were too busy building your empire to teach them. Now you’re rich, and they’re strangers in a world you created. Moms see their kids through a love lens, swearing their children will never fight over money. But millions turn harmony into chaos. I’ve seen it.

Here’s how to stop the black hole. First, talk about money now. Not the polished pitch you gave VCs—the raw stuff. The failures, the sacrifices. Let your kids manage a small account; let them lose $1,000 and feel the sting. Discuss it and get their thoughts and feelings going.

Second, give them purpose. Fund their ideas, but make them earn it. I had a client whose son wanted to start a tech venture. He got $50,000 but had to pitch a business plan first. No plan, no cash. He caught the entrepreneur bug as he now had invested into something he wanted to see gain customers and start to grow.

Third, plan for the fallout. Set up a trust with a neutral trustee. Tie payouts to milestones—education, philanthropy, or starting a business. Hire a wealth management firm that’s seen families implode. You can’t force your kids to be you. They won’t know your struggles, and that’s okay. Your job is to give them tools, not a blank check. Start a family foundation and use a DAF; let them run it. Show them giving can be done in a systematic and generous style, but with the correct decision-making format, administration and taxes. This is grown-up, not fantasy philanthropy.

Wealth can fuel ambition or breed entitlement. It can be wonderful at creating empowered Canadians who give so much or it can be a depressant. Small changes can really make a difference.

You choose. Jacoline Loewen has guided families through wealth’s pitfalls for decades. Connect to turn your fortune into a legacy, not a family feud.

How to Sell Your Family Business Without Breaking Promises (or Your Family)

By Jacoline Loewen

I’ve spent decades working with business owners, watching them wrestle with the messy, emotional, and downright human side of selling their companies. It’s never just about the money—it’s about legacy, family, and the promises you made over dinner tables and late-night boardroom talks. This post, I’m tackling a topic that keeps many of you up at night: how do you sell your business to a third party when you’ve sworn it would stay in the family? And while we’re at it, let’s talk about compensation fights between your kids, the advisors who’ve left you with a tax bomb, and why your business might not be the legacy you think it is. Buckle up—this is going to feel like a therapy session with a side of spreadsheets.

# 1. Selling to a Third Party After Promising the Kids the Keys

You’ve spent years telling your children the business would be theirs. Maybe you even pictured them running it, passing it down to their own kids. But now, the market’s hot, a buyer’s knocking, or you’re just tired—and selling to an unrelated third party looks like the best move. How do you navigate this without torching family dinners for the next decade?

First, own the pivot. You’re not betraying anyone—you’re making a tough call for the right reasons. Maybe the kids aren’t ready to run it (or don’t want to). Maybe the business needs more capital or expertise than the family can provide. Whatever the reason, be honest. Sit the family down and explain why selling makes sense—not just for you, but for them. Paint the picture: liquidity now could fund their dreams, secure their futures, or give them freedom to pursue their own paths.

Next, get creative with the transition. If the kids are emotionally tied to the business, explore ways to keep them involved post-sale. Could they stay on as advisors or minority shareholders? Could the sale proceeds fund a new family venture they actually care about? The goal is to shift the narrative from “I’m selling your inheritance” to “I’m unlocking our family’s next chapter.”

Finally, bring in a neutral third party—a mediator or family business consultant—to facilitate the conversation. They’ll help you avoid the trap of playing favorites or letting old grudges derail the process. Selling doesn’t mean breaking your promise; it means redefining it. Done right, your kids will thank you for the clarity (and the cash).

# 2. Navigating Compensation Wars Between a Star Kid and a Slacker

Let’s talk about the elephant in the room: one of your kids is a rockstar, driving the business forward, while the other… well, they show up when they feel like it and they hate capitalism. How do you pay them fairly without sparking a family feud?

Step one: separate ownership from employment. If both kids own equal shares of the business, that’s fine—dividends or profits can be split evenly. But compensation for work? That’s based on performance, not DNA. The high-performer should be paid market rates for their role, the same as any non-family employee. The non-performer? Pay them only for what they actually do. If they’re not contributing, they don’t get a paycheck just for being your kid.

Step two: get transparent. Hold a family meeting (yes, another one) and lay out clear job descriptions, KPIs, and salary benchmarks. Use data—Glassdoor, industry reports, whatever it takes—to show why the high-performer earns more. If the non-performer feels slighted, give them a path to step up: training, mentorship, or a specific role they can grow into. If they don’t take it, that’s on them.

Step three: protect the business. If the non-performer is dragging things down, consider an exit strategy for their role—maybe a buyout of their shares or a severance package tied to a graceful exit. Harsh? Maybe. But a family business isn’t a charity, and resentment between siblings can poison everything.

Pro tip: hire an independent HR consultant to review compensation and present findings. It takes the heat off you and signals fairness. The goal isn’t to pick a winner—it’s to keep the business (and your family) intact.

# 3. The Massive Tax Bill No One Warned You About

You’ve built a successful family business, and you’re ready to pass it on to your kids or sell it and retire. Then you die, and your kids are hit with a capital gains tax bill so big they have to sell the business just to pay it. No liquidity, no plan, just a mess. Who’s to blame? Your accountant, financial advisor, lawyer, or all of them?

The answer is D. All of the above.

Here’s why:

- Accountant: They should’ve flagged the tax implications of your estate plan years ago. Capital gains tax on a business transfer can be brutal, but tools like estate freezes, trusts, or insurance policies can minimize the hit. If they didn’t bring these up, they failed you.
- Financial Advisor: They’re supposed to model your wealth and ensure liquidity for taxes or succession. They should be able to discuss next-gen asset management too. If they didn’t stress-test your plan for a worst-case scenario (like your death), they are dropping the ball..
- Lawyer: They draft the wills, trusts, and shareholder agreements. If they didn’t structure your estate to avoid or defer taxes—or at least warn you about the risks—they’re not doing their job.

The real issue? Silos. Too often, these advisors don’t talk to each other. You need a quarterback—someone who coordinates the team to create a cohesive plan. If you don’t have one, hire a family office advisor or wealth planner/strategist to oversee the big picture.

And don’t just blame the advisors—take responsibility. Ask hard questions. Demand scenarios. If you’re not hearing about taxes, liquidity, or succession risks, fire someone. Your kids shouldn’t pay for your blind spots.

# 4. Your Business Isn’t Your Legacy—Your Family Is

I’ll wrap up with a question I’ve asked hundreds of audiences: *Who founded Canadian Tire?* Crickets. Always. No one knows (it was the Billes brothers, by the way). Yet Canadian Tire is one of the most iconic brands on Earth. If no one remembers its founder, do you think your family business will be your lasting legacy?

Spoiler: it won’t.

Your business is a tool, not a monument. It’s a means to create wealth, security, and opportunities for your family. But your real legacy? It’s your kids, your values, the way you shape their lives. A family business can tear families apart or bring them closer—it’s your choice.

So, as you think about selling, compensating your kids, or planning for taxes, remember this: your greatest work of art isn’t the company you built. It’s the family you nurture. Make decisions that strengthen those bonds, not break them.

Got questions about selling or succession? Drop me a line. I’m here to help you navigate the messy, human side of business.

Jacoline Loewen works with successful families to navigate their assets and family business. With her background, she’s seen it all—sibling rivalries, tax disasters, and everything in between. She helps business owners make smart, human-centered decisions to protect their wealth and their families.

The Power of the First Family Wealth Meeting: A Journey into Connection and Clarity

There’s a unique energy in the room when a family gathers for the first time to discuss their wealth. It’s a blend of anticipation, curiosity, and, yes, a touch of awkwardness. There is also skepticism and even anger. As a family member and also a professional facilitator for these inaugural family meetings, I’ve experienced this dynamic time and again.

Each meeting is a fresh canvas, a chance for a family to begin a transformative conversation about their shared financial legacy. These initial gatherings plant a seed—one that families, or their advisors, can nurture in future meetings.

These meetings are special because they mark a family’s first step toward openly discussing their wealth. There’s an undeniable excitement in this novelty, but it’s often accompanied by mild anxiety. Will everyone get along? Will sensitive topics derail the conversation? These concerns are natural, yet I’ve found that families who take the leap to hold that first meeting are almost guaranteed to schedule a second, third, and even fourth. There’s something magnetic about starting this dialogue—it’s as if the act of gathering unlocks a desire to keep the conversation going.

Why do some families hesitate to gather while others embrace it. Families who show up for these meetings are, in a sense, self-selecting. They’re ready to confront the complexities of their relationships and their wealth, even if they don’t fully realize it yet.

Setting the Stage for Success

As a facilitator, my job is to create a safe, structured environment where every voice is heard. The agenda for a first family wealth meeting is deliberately simple. We might start by discussing the family’s values—what matters most to them as individuals and as a unit? From there, we explore their goals for their wealth. Is it about preserving a legacy, funding education, supporting philanthropy, or something else entirely? These conversations lay the groundwork for deeper discussions in future meetings, such as estate planning or governance structures.

The awkwardness that often accompanies these first meetings tends to dissipate as family members realize they’re not alone in their uncertainties. I’ve seen siblings discover shared values they never knew they had, and parents gain new insights into their children’s aspirations. The advisor plays a crucial role here, acting as a steady guide who can translate financial complexities into meaningful dialogue. When advisors witness the power of these facilitated discussions, many are inspired to take on the role themselves. For those who find facilitation isn’t their strength, they often engage a professional facilitator for future meetings—a testament to the value these gatherings bring.

Why It Matters

The first family wealth meeting is more than a discussion about money; it’s a step toward building stronger family connections and a shared sense of purpose. Wealth can be a source of tension, but it can also be a catalyst for unity when approached with intention. Families who commit to this process often find that their conversations evolve over time, growing richer and more strategic with each meeting.

For advisors, facilitating or supporting these meetings is an opportunity to deepen client relationships and demonstrate their value beyond portfolio management. For families, it’s a chance to align their wealth with their values and create a legacy that reflects who they are. And for me, as a one-time facilitator, it’s a privilege to witness the spark of that first conversation—a spark that ignites a journey of discovery and connection.If you’re an advisor or a family considering a first wealth meeting, take the leap. The awkwardness will fade, but the clarity and connection you gain will endure. And who knows? That first meeting might just be the start of a tradition that shapes your family’s future for generations to come.

The Hidden Cost of High-Net-Worth Divorce

Wealth, Family, and Legacy is the dream goal. In fact, it is more than that. It is wealth managed well, a happy family where all are respected, and lasting values that can be the rudder for future generations. However, divorce is the big rock in the pond of camness. Divorce doesn’t just end a marriage—it reshapes a family’s emotional and financial DNA. For high-net-worth couples, the fallout extends far beyond the couple, rippling through estate plans, family businesses, trusts, and future generations. The real casualty? Not just wealth, but the cohesion that sustains it.A Legacy Disruptor
In affluent families, children often play roles in family enterprises—managing businesses, leading philanthropy, or governing trusts. Divorce, especially when fraught with tension, jeopardizes these roles. Who stays involved in the family business? Are stepchildren still included in estate plans? Will a parent favor a new spouse in their will? These questions, often unasked until crisis hits, threaten the unity that generational wealth depends on. Without foresight, divorce can fracture not just relationships but the structures that preserve a family’s legacy.

“Staying for the Kids” Isn’t Always Better

“We stayed together for the kids” is a noble sentiment, but it can backfire. Children in high-net-worth families sense when love is gone, even if it’s unspoken. Staying in a cold, transactional marriage to preserve wealth or image often normalizes emotional distance for kids. They grow up equating relationships with tension or resentment, absorbing anxiety instead of authentic family values. A respectful, well-handled divorce can be less damaging than a performative unity that prioritizes money over well-being.The Emotional Toll Turns Financial
The effects of divorce linger, shaping how children navigate wealth and responsibility:

• Distrust in systems: If a parent feels blindsided financially, kids may lose faith in advisors or legal structures.

• Avoiding leadership: Some heirs shy away from family roles after witnessing parental conflict.

• Inheritance resentment: Post-divorce wealth splits can leave children feeling punished, especially in blended families.

• Sibling rivalry: Dividing assets among children from multiple marriages often sparks disputes or perceived favoritism.

Wealth, when mishandled, becomes a tool for control or division. Divorce amplifies this risk, turning emotional wounds into financial ones.What Children Wish Parents Knew
Children of high-net-worth divorces often say the same thing: the divorce itself wasn’t the worst part—it was being left in the dark. Parents made decisions without their input, expecting them to adapt. Fights over money overshadowed family values. Kids felt pressured to pick sides. Many grew up hearing, “One day, this will be yours,” only to face silence or secrets post-divorce. Open communication could have softened the blow.

Divorce triggers a cascade of necessary updates that often go ignored. Wills may still name an ex-spouse, granting them unintended control in case of incapacity or death. RRSPs, TFSAs, or trusts may have outdated beneficiaries. Family foundations or businesses can become awkwardly co-managed by exes or abandoned entirely. These oversights risk misaligning wealth with a family’s new reality, creating legal and emotional chaos.

Family offices and advisors must do more than manage logistics. They have a duty to protect relationships, roles, and long-term cohesion. High-net-worth divorces demand proactive planning—updating estate documents, clarifying business roles, and fostering open dialogue with children. Wealth is only as strong as the family behind it. By addressing the emotional and financial fallout head-on, families can preserve not just their assets but the legacy they’ve built together.

The Family Silence Trap

I’ve seen it too many times: parents build a fortune, kids grow up in its shadow, and nobody says a word about it. The parents don’t want to “spoil” the kids or burden them. The kids, sensing the unspoken, stay quiet too, afraid to seem greedy or clueless. This silence is a ticking time bomb.

Wealth isn’t just money—it’s responsibility. If the next generation doesn’t know the plan, they’re set up to fumble. I’ve watched heirs inherit millions, only to burn through it because no one taught them how to manage it. Parents think shielding kids from wealth’s weight protects them. Wrong. It leaves them defenseless.

And it’s not just the kids. Parents who don’t talk about their estate risk leaving a mess—legal battles, tax hits, or worse, a family fractured over misunderstandings. A candid conversation about values, goals, and mechanics (trusts, wills, philanthropy) isn’t easy, but it’s essential.

Break the silence. Start small: share your financial philosophy, not just the numbers. Teach the kids to respect wealth, not worship it. Families that talk openly about money don’t just preserve wealth—they build stronger bonds. Silence? That’s the real wealth killer.

There are Six Family Office Models

Family Offices are unique and have different features. Here are six models.

1. The Founder’s Family Office Where the visionary who created the fortune still calls the shots • FO created after founder's financial success • Founder drives operations & retains control • Focus on first-gen wealth & legal/financial structures • Major challenges: transitioning ownership to next-gen.

2. Administrative/Compliance Family Office Wealth brings complexity... here's where the family office starts to do the heavy lifting • Coordinates and records assets and wealth planning needs • Oversees tax returns, banking, insurance, and service-provider relationships • Services include lifestyle management, tax payments, estate planning, and document management • Concierge services such as property management, travel, jet acquisitions, private collections, gifting, insurance, staffing, and jet maintenance

3. The Philanthropic Family Office Where the family is serious about giving, governance, and growing the next generation of leaders • Focuses on charitable giving, impact investing, and engaging heirs for wealth transition • Prioritize education and planning in philanthropy, estate, finance, and family governance • Manages family foundations or philanthropic funds, offering management, oversight, and advisement services • Family members can use the philanthropic family office as a platform for education, involvement, and leadership development

4. Direct Investment and Investment Offices When the FO helps the family become a strategic, tax-savvy investment machine • Handles financial, accounting, and investment affairs of the family • Provide streamlined advisement, consolidated reporting, and strategic and tactical investment approaches • Some investment offices focus exclusively on direct investments, acting as boutique private equity or venture capital firms • Investment offices prioritize tax-efficient investing, estate planning, liquidity management, and short- and long-term wealth objectives

5. The Family Business-Focused Family Office Where the family-operated company still dominates - until it's time to cash out • Start within the business and may eventually separate wealth management from the business • Manage owners' wealth and provide diversification to the business, addressing wealth transfer, tax, and ownership control • Services include advising on stock repurchase, buy/sell agreements, debt and credit management, generating liquidity • May support business restructuring or sale • Provide financial planning, analysis, and legal, ownership, income tax, estate and gift tax planning, fiduciary planning, asset protection, and family governance

6. The Multigenerational-Focused Family Office: The ultimate legacy family office built to protect wealth and unity for generations • Services include lifestyle planning, investment and tax mgmt, estate and fiduciary mgmt, risk mgmt, financial education, and philanthropic services for a complex group of family owners from different branches • Some families outsource to a multi-family office for cost efficiency • This family office is proactive in wealth transfer planning and has a sophisticated governance system, including family policies, committees, and decision-making processes • Family continuity, cohesion, and buy-in are important attributes

How to Actually Grow Your Real Wealth

By Jacoline Loewen

So, how do you build this qualitative wealth? It’s not about throwing cash at therapists or scheduling awkward family retreats (though those can help). It’s about intentional, consistent effort. Here’s what I suggest, with a few of my practices I have observed from wealthy Canadian families sprinkled in:

Human Capital

• Support individual flourishing. Make sure every family member has access to great healthcare—mental and physical. If someone’s struggling with addiction or illness, don’t sweep it under the rug. Get them help.

• Encourage identity outside wealth. Your kids aren’t just “heirs.” Push them to find their own path—whether that’s art, tech, or flipping burgers. Their sense of self shouldn’t be tied to the family bank account.

• Go global. The world’s small now. Encourage your family to live, work, or travel in different corners of it. It builds resilience and perspective.

Legacy Capital

• Share your stories. Not just the wins—the failures, too. My grandpa used to tell me about the time he lost everything in a bad deal, then clawed his way back. Those stories shaped me more than any trust fund could.

• Clarify values. Sit down and talk about what matters to each of you. Where do you overlap? Where do you differ? Respect both.

• Honor traditions (but don’t cling to them). Keep the ones that spark joy, ditch the ones that feel like a chore.Family Relationship Capital

  • Hold regular family meetings. Not to talk about investments, but to talk about you. Hire a facilitator if you need to. Learn how each person communicates—some of us are direct, others beat around the bush. Figure out how to mesh.

  • Include spouses. They’re not outsiders—they’re raising the next generation. Get their perspectives, even if it feels awkward at first.

  • Fix trust issues. If there’s tension, don’t ignore it. Bring in a counselor to help you work through it. It’s cheaper than a family feud.

  Structural Capital

  • Demystify the legal stuff. Make sure everyone understands the trusts, partnerships, and governance structures—at their level. Clarity kills confusion.

  • Educate, don’t dictate. Bring in advisors to teach, not just manage. I’ve seen families transformed when the kids actually get how the family office works.

  • Plan for leadership. Not everyone wants to be the next CEO, but identify who’s got the spark and train them up.

  Social Capital

  • Give back, at every age. Even the youngest kids can learn the joy of helping others. Make it part of your family DNA.

  • Empower philanthropy. Let each family member choose causes they care about. It’s not just about writing checks—it’s about impact.

  • End with gratitude. Try this: at every family gathering, have everyone share one thing they’re thankful for. Sounds cheesy, works like magic.

  The Money Taboo

  Here’s where it gets tricky: financial capital. I’ve seen in my own life—families hate talking about money. It’s the last taboo. Some of it’s embarrassment—people feel uneducated or disempowered. Some of it’s fear—talking about wealth can make you a target, even within your own family. I’ve had friends who’ve been burned by relatives who saw them as walking ATMs.

  But silence has a cost. If you can’t talk about money productively, you’re setting yourself up for mistrust, bad decisions, and fractured relationships. The book’s advice? Create safe spaces to talk about it. Not to obsess over it, but to use it as a tool to fuel the other four capitals. Money’s not the goal—it’s the enabler.

  Measuring What Matters

  Here’s a wild idea: what if you tracked your qualitative wealth the way you track your portfolio? Most families don’t. They’ve got quarterly reports for their investments, but nothing for their human, legacy, or social capital. No wonder so many families flounder.

  The book suggests a system called Family Qualitative Capital Management. It’s like a balance sheet for your family’s well-being. Every year, each family member spends 20-30 minutes answering questions about their health, relationships, values, and community ties. The results get rolled into a report that shows your strengths and weaknesses. Then, you meet as a family, make a plan to improve, and check in twice a year to see how you’re doing.

  It’s not rocket science, but it’s powerful. Imagine knowing—not guessing—where your family’s at. Are your relationships strong? Is your legacy clear? Are you giving back enough? This kind of clarity is what separates families that thrive from those that just coast.

  The Investment That Pays Forever

  One last thought. Compare what you spend on managing your financial capital—advisors, lawyers, accountants—to what you invest in your qualitative capital. Most families spend a fortune on the former and pennies on the latter. Flip that. Investing in your family’s well-being—through time, energy, and yes, some money—is the ultimate impact investment. It’s not just about preserving wealth for the next generation. It’s about building a family that’s healthy, connected, and purposeful.

  I think about my friend at the diner who sold his company for a significant portion and is now battling to speak with his family. He’s got the money part figured out. But if he wants his family to be truly rich—not just sometimes have money—he’s got to start investing in the other stuff. The human stuff. The legacy stuff. The stuff that makes life worth living.

  So, what about you? What kind of wealth are you chasing for your family? And how are you going to measure it?

The Big Mistake Families Make with Wealth

Most families obsess over the financial piece.

They hire advisors to manage portfolios, set up trusts to “protect” the wealth, and drill into their kids the importance of being “good stewards” of the money. But that’s like polishing the hubcaps on a car with a busted engine. If your family’s relationships are frayed, if your kids don’t know who they are outside the family fortune, if you’re not connected to a bigger purpose—good luck keeping that money in the family. It’ll either tear you apart or slip away.

A grandmother who was part of a generationally wealthy family said it best: “Our family has always been rich, and we’ve sometimes had money.” That’s the distinction in a nutshell. Qualitative wealth—human, legacy, relationships, structure, social impact—is what makes a family rich. Money just helps you get there.

The Real Wealth Your Family Should Be Chasing

By Jacoline Loewen

I was sitting at a diner with a friend the other day, talking about family. He’s got a big one—three kids, a sprawling extended clan, and a decent chunk of money to his name. He was stressing about how to keep it all together. Not the family, mind you—the money. “How do I make sure it stays in the family?” he asked, like it was the only thing that mattered.

I get it. The world’s built an entire industry around this idea: preserve the cash, lock it up tight, pass it down like a sacred heirloom. Advisors, lawyers, trusts, family offices—all designed to keep the dollars from slipping away. But here’s the thing: they’re missing the point. Money isn’t the goal. It’s a tool. The real wealth? It’s your family’s well-being. And no, I’m not talking about some touchy-feely nonsense. I’m talking about the stuff that makes a family thrive for generations—human capital, legacy, relationships, structure, and social impact. That’s the wealth that matters.

Let me break it down.The Five Kinds of Wealth You’re Probably Ignoring

The book Complete Family Wealth by James Hughes (which I’ve been diving into lately) nails this. It says families have five types of capital, and only one of them is money. The other four? They’re the qualitative stuff—harder to measure, but way more important. Here’s the lineup:

1. Human Capital: This is your people. Their health, happiness, and ability to find purpose. Are your kids growing into adults who know who they are, apart from the family fortune? Are you supporting their mental and physical well-being? That’s human capital.

2. Legacy Capital: Your family’s values, stories, and shared purpose. It’s the “brand” of your family—what makes you distinct. Think of the traditions you cherish, the failures you’ve overcome, the history that binds you. That’s legacy.

3. Family Relationship Capital: Can your family talk—really talk? Not just about who’s hosting Thanksgiving, but about the big stuff: values, fears, dreams. Strong communication across generations is the glue that holds a family together.

4. Structural Capital: If you’ve got wealth or a family business, you’re probably tangled in trusts, partnerships, and legal setups. Structural capital is understanding that maze and navigating it without losing your mind—or your family’s unity.

5. Social Capital: This is your family’s connection to the world beyond itself. It’s the joy of giving back, the strength you draw from serving your community. Families that invest here don’t just survive—they make a dent in the universe.

Boats at Friday Harbour, My Watercolour Painting.

And then, yes, there’s Financial Capital. The cash, stocks, real estate. It’s important—don’t get me wrong. It funds healthcare, education, philanthropy, and the time to sit down and figure out what matters. But it’s only one-fifth of the equation. And it’s the least important when it comes to happiness.

Great Family Businesses need Good Governance

We celebrated Canadian Family Businesses and Governance Excellence at the ICD SWO Event at the London Hunt and Country Club.

What an insightful evening with the Institute of Corporate Directors SWO fireside chat. My long-time friend, David Simpson of Ivey Business School at Western University joined me to discuss Canadian family businesses and their governance needs. Family businesses are vital to our economy, and their success requires tailored governance.

IDC alumni and family businesses were guests and, for me, the best part of the session were their questions to David.

Why Governance for Family Businesses is Unique
Family enterprises blend personal relationships, legacy, and wealth. David Simpson said, "A business is an asset". The best Trusted Advisors understand these tricky nuances—emotional ties, control, desire for legacy & intergenerational goals. It’s a balance between family harmony and business growth, and ICD experts will create the governance path for families to effectively manage their assets - business, portfolio, and yes, family.

Key Insights from the Evening
Sifton Properties Limited Success: The Sifton family’s family council, inclusive of spouses and non-active members, shows how structured communication and shareholder agreements can facilitate generational transitions while preserving unity.
Other Canadian Icons: From EllisDon’s professionalized boards to McCain Foods’ strategies for resolving leadership disputes, and the Weston family excellent oversight at George Weston Ltd. Loblaw, these cases demonstrate the power of governance in maintaining legacy.

Thank you to our National ICD sponsors: Deloitte KPMG Osler, Hoskin & Harcourt LLP Torys LLP and a shout out to our fantastic SWO sponsors Gowling WLG

For those who would like to discuss the discussion about Family Business and Governance, please contact me: Jacoline Loewen Burgundy Asset Management Ltd. https://lnkd.in/gnPQ6Pn3

Never Enough: Governance That Doesn’t Suck for Family Businesses

Family businesses are a tightrope walk—love, legacy, and money tangled up in a way that’d make most corporate suits run screaming. From the first generation grinding it out to the fourth generation wondering if they’re just coasting on great-grandpa’s hustle, keeping things together takes more than a handshake and a holiday dinner. Governance isn’t sexy, but it’s the glue that stops the whole thing from imploding. Here’s how to do it right, with real-world stories to prove it’s not just theory.

1. Figuring Out What Your Family’s Actually Good For

Nobody wants to admit their cousin’s a dud at running the show, but pretending otherwise is a recipe for disaster. You need a system to size up who’s got the chops and who’s just along for the ride.

• Build a Scorecard: Use real tools—360-degree feedback, personality tests, the works—to measure skills and ambition. Bring in outsiders like consultants to keep it honest. Example: The Mars family (yep, the candy people) has long used external advisors to vet who’s ready for big roles, avoiding the trap of handing keys to someone just because they share the name.

• Talk It Out, But Not at Thanksgiving: Set up regular family meetups, separate from boardroom drama, to hash out what everyone wants. A facilitator helps keep it from turning into a shouting match. Case: The Murdochs tried this with family councils, but it went sideways when egos clashed—learn from their mess and keep it structured.

• Train ‘Em Up: Spot weaknesses early and throw resources at them—courses, mentors, whatever. Example: Walmart’s Walton family puts heirs through rigorous prep, from store floors to strategy sessions, before they touch real power.

• Write It Down: A family employment policy isn’t bureaucracy—it’s a sanity saver. Spell out who can work, how they qualify, and what happens if they don’t cut it.

This works because it’s fair but firm. You’re not crushing dreams; you’re giving everyone a clear shot based on what they bring to the table.

2. Succession That Doesn’t End in a Bloodbath

Picking the next leader is where family businesses often crash and burn. You don’t want a situation like the Succession show—here’s how to keep it chill.

• Get a Referee Team: A board subcommittee, heavy on independent directors, should run point on succession. They judge on skills, not last names. Case: Ford Motor Company dodged a bullet by having a board committee groom Alan Mulally (a non-family pro) before handing things back to Bill Ford—structure saved them.

• Set a Bar: List what a leader needs—vision, numbers savvy, people skills—and stack candidates against it. No fudging. Example: Italy’s Ferrero (Nutella kings) benchmarks family contenders against global execs to keep standards sky-high.

• Play the Long Game: Spot talent early and give them real-world tests—rotations, projects, maybe even a stint outside the company. Case: The Tata Group in India trains heirs like Ratan Tata across divisions for decades, building trust and cred.

• Make a Family Rulebook: A family constitution lays out how succession works, so nobody’s blindsided. Example: Denmark’s Lego family uses theirs to keep everyone aligned, even when tensions flare.

This keeps things merit-based but human. Nobody feels screwed over when the rules are clear.

3. Keeping Siblings From Going Full Cain and Abel

Hand one sibling the crown, and the others might start sharpening knives. Here’s how to keep the peace.

• Bring in a Neutral: A third-party facilitator—think corporate therapist—can guide talks about who gets what role. It’s less biased than Mom picking sides. Case: The Ambani family in India used mediators to sort out a messy sibling split at Reliance, though it still cost them billions in drama—don’t wait that long.

• Give Everyone a Job: Not every role needs to be CEO. Define spots—advisory, philanthropy, board seats—and make them feel legit. Example: The Lauder family (Estée Lauder) assigns siblings to niche roles like brand innovation, keeping everyone engaged without overlap.

• Pay Fair, No Favorites: Transparent comp and equity rules tied to actual work stop the “why’d she get more?” fights. Case: The Koch brothers’ empire nearly cracked over uneven payouts—clear policies could’ve saved years of lawsuits.

• Have a Plan B: A dispute resolution process (mediation, arbitration) in the family constitution catches fires before they spread. Example: Spain’s Zara-owning Ortega family uses this to keep minor spats from blowing up their retail juggernaut.

This works because it respects everyone’s place while making sure the business doesn’t become collateral damage.

4. When Family Leadership Ain’t It (And How to Say It)

Sometimes, the family’s bench is weak, and you need a pro to run things. Here’s how to figure it out and break the news without a family feud.

• Stack Up the Talent: Compare family candidates to what’s out there. Exec search firms can show you how they measure up. Case: BMW’s Quandt family stepped back when they saw Herbert Quandt couldn’t match pros like Norbert Reithofer—data drove the call.

• Look Ahead: If the business needs skills nobody’s got (say, tech expertise for a digital pivot), admit it. Example: The Redstone family at ViacomCBS flopped by sticking with insiders too long—hiring pros earlier would’ve saved shareholder value.

• Test the Waters: Give family members a shot in interim roles, but keep pros on speed dial. Case: The Riggs family at Chesapeake Energy tried this, but weak internal talent forced a pivot to outside CEOs—temporary roles clarified the gap.

• Vote It Out: Independent directors should need a supermajority to pick a non-family leader. It’s a gut check for fairness.

How to Tell the Family:

• Be Straight: Call a family meeting and lay out the why—focus on the company’s survival, not personal failings. Example: The Pritzker family (Hyatt hotels) did this when they brought in outsiders, framing it as growth-driven.

• Sell the Upside: Point to wins like LVMH, where pro CEOs turbocharged a family legacy without erasing it. Keep it positive.

• Keep Them In: Offer board seats or advisory gigs to family members. It softens the blow. Case: The Newhouse family at Condé Nast keeps influence via governance roles despite pro management.

This works because it’s rooted in reality, not ego. Clear talk and a plan keep everyone on board.

5. How Many Family Members Should Crowd the Board?

Too many family faces in the boardroom, and it’s just a family reunion with fancier coffee. Here’s how to get it right.

• Earn the Seat: Set hard rules—industry know-how, governance chops—for family directors, same as anyone. Example: The Agnelli family (Fiat) only lets prepped heirs like John Elkann near the board.

• Rotate the Reps: Cap family seats at a couple and swap them out regularly to avoid cliques. Case: The Weston family (Loblaws) rotates to keep fresh family voices without overload.

• School Them: Governance training for family directors isn’t optional—it’s how they learn not to tank the company. Example: The Cargill family (agribusiness giant) mandates this, keeping their board sharp.

• Offload Family Drama: A family council handles sibling gripes, so the board can focus on strategy. Case: The Roche family (pharma) uses this to keep their boardroom clean of personal beefs.

This balances family pride with actual competence, so the board doesn’t turn into a soap opera.

6. Mixing Family and Outsiders on the Board

A board that’s all family or all suits is a recipe for stagnation. Here’s the sweet spot.

• Tilt Independent: Aim for 60-70% independent directors, 30-40% family. It’s objective but keeps the legacy alive. Example: The Hermès family caps their board influence, letting independents steer strategy while they hold veto power.

• Keep It Tight: 7-11 members max—big enough for brains, small enough to move fast. Case: The Swatch Group’s Hayek family keeps it lean, avoiding decision paralysis.

• Mix It Up: Pick independents with varied skills—tech, finance, ops—to cover blind spots. Example: The Molson family (beer empire) brings in heavyweights to balance their brewing passion.

• Don’t Let It Fossilize: Term limits for everyone keep ideas fresh. Case: The Sulzberger family (New York Times) uses this to avoid entrenched thinking.

This works because it blends heart and hustle—family soul with outsider smarts.

7. Family Friends as “Independent” Directors? Nope.

Your buddy from poker night isn’t independent, no matter how much he swears he’s impartial. Independence means no strings attached. Danier Leather's second-generation leadership hired buddies for the board and paid them a hefty fee. Do you think anyone will rock the boat and risk getting thrown off the board?

• Hard Line: No prior ties—business, personal, nothing. Follow strict governance codes. Example: The Walton family got heat for cozy board picks early on—going fully independent later boosted credibility.

• Hire Hunters: Use exec search firms to find directors who don’t owe you favors. Case: The L’Oréal Bettencourt family leans on pros to source board talent, keeping it clean.

• Check Yearly: Make every director disclose connections annually. No surprises. Example: The Murdoch family’s News Corp faced scrutiny for lax independence—rigorous checks could’ve helped.

This works because real independence builds trust, inside and out. Anything less is just playing pretend.

Wrapping It Up

Family businesses don’t survive four generations by winging it. Governance that’s thoughtful, tough, and transparent turns chaos into a machine that can outlast the drama. From sizing up talent to picking leaders, managing sibling egos, or knowing when to call in the pros, it’s about systems that respect the family without letting it choke the business. Look at Mars, Ford, or Hermès—they’re still here because they got this right.

Do This Now: Dig into your governance setup. If it’s a mess, call in advisors who’ve seen it all. Don’t wait for the next family BBQ to turn into a boardroom brawl.

My painting - Gibson Hills Forest - Acrylics 12”x14”. Ontario, Gibson Hills, near Aliston.

What Gene Hackman's Legacy Teaches Us

Are you a wealthy entrepreneur looking to give back? Consider what excites you, what breaks your heart, and where you can make the most impact. Discussing these questions with your family can strengthen relationships and even build a shared vision for giving.

“We work on average, 78,000 hours in a lifetime; spend just 2 hours to decide if your wealth will benefit or harm your beneficiaries.”

— Tom Deans, Author of Willing Wisdom

Legacy planning teaches us valuable lessons. For instance, the famous actor Gene Hackman's recent passing left an $80M fortune but he excluded his children, leading to public, messy lawsuits and toxic family discord.

There were also many comments on Social Media about how thoughtless Hackman’s philanthropy appeared to be. What would be the life impact on his children? Would it shorten their lives and destroy them? Also, there was frustration aimed at Gene Hackman that he did not build up the people in his industry and leave an impact for the next generation of movie creators. There was much discussion about how Hackman could have had a far more positive impact on the lives of young actors and filmmakers through scholarships and donations while he was alive. Plant the seeds of trees even though you know you will never enjoy their shade.

Thomas Deans, Ph.D., author of "Willing Wisdom", says that we work on average 78,000 hours in a lifetime; spend just 2 hours to decide if your wealth will benefit or harm your beneficiaries. Looking at legacy planning from the view of the impact on people in your life may bring a better outcome.

My painting - Spring River, Watercolours, 14 x 20. March, 2025, In Ontario, Seabright.

Family Businesses: The Ultimate High-Wire Act—With No Net!

Family businesses? They’re not just businesses. They’re emotional rollercoasters strapped to a P&L statement, racing through a minefield of chaos. Sure, they wrestle with the same brutal beasts as every other outfit—cashflow nightmares, tech glitches, supply chain snarls, cybersecurity boogeymen, and the eternal HR headache (good luck finding talent that doesn’t bolt at the first whiff of dysfunction). Add in political curveballs—tax hikes, trade wars, environmental regs—and a creeping dread of AI that’s got owners attention. But that’s just the warm-up act.

What sets family businesses apart? Feelings. Raw, messy, unfiltered emotions—from the dizzying highs of triumph to the gut-punch lows of betrayal. It’s a circus of joy and agony, and I’ve experienced it in my family business and I’ve seen it up close—advising, coaching, and financing for family firms teetering on the edge. Here’s my hit list of 10 gnarly problems I’ve tackled head-on. (Spoiler: there’s more where these came from!)

1. Family Flunkies Dodging the Axe
   Can’t fire Cousin Jimmy, even when he’s a walking disaster? Blame Mom—the matriarch who’d rather hug it out than hand out pink slips. Or maybe the boss is a “Harmony” junkie (Gallup’s term, not mine). Either way, dysfunction festers.

2. Nepotism on Steroids
   Junior gets the corner office before he can spell “ROI,” while non-family grunts grind their teeth. Or worse, the next gen’s forced to stay, half-hearted and hating it. Meritocracy? Ha!

3. Vision Misalignment
   Patriarch says jump; everyone else says, “How high—or why bother?” Work ethic gaps and values clashes turn teams into warring tribes. Alignment? Dream on.

4. Succession Planning Paralysis
   The big kahuna’s “my way or the highway” vibe steamrolls the next gen’s ideas. No plan? No future. I’ve seen this blow up in good times and bad—health crises or harmony be damned.

5. Relationship Handoff Hell
   Founders cling to clients like life rafts, especially in sales. Short-term relief, long-term pain. Transition? They’d rather eat glass.

6. Father-Son Cage Matches
   Dominant dads (think DISC’s “D” or Gallup’s “Command”) lock horns with sons itching to prove themselves. Decisions stall for years. Lawyers and accountants just fan the flames.

7. Sibling Smackdowns
   Power, cash, favoritism—siblings build silos, rally minions, and turn departments into battlegrounds. Patriarchs play ref, but the rift grows. Coaching can tame this beast—sometimes.

8. Staff vs. Family Smackdown
   Blood gets the perks—roles, info, dough—while staff eat crumbs. “Master Rules” workshops can shine a light, but don’t expect hugs all around. Blood’s thicker, period.

9. Strategic Tunnel Vision
   Patriarchs lean on gut and loyal yes-men, shunning outside intel. Works till it doesn’t. Big accounting firms swoop in with fancy plans—but no follow-through. Acceptance? Execution? Good luck.

10. Peer Group Pity Parties
    Roundtables and “Old Boys” clubs start strong, then devolve into whine-fests. Add accountants or advisors, and it’s a circle-jerk of stagnation. Succession? Entrepreneurship? Kiss ’em goodbye.

    Here’s the kicker: family businesses thrive on passion, loyalty, and grit—until they don’t. The fix? Open minds (Big 5’s “Openness,” anyone?). Patriarchs, matriarchs, and sulky heirs need to ditch the drama and act like adults (shoutout to Eric Berne’s Transactional Analysis). Embrace AI, outsiders, and fresh ideas—or watch the circus tent collapse. I’ve helped dozens dodge that fate. You can too. Call me.

Jacoline Loewen partners with family businesses to cut through the noise and build lasting legacies.

My painting as winter leaves - Snowy Walk, Watercolours, 14”x20”, February, 2025. In Ontario, near Creemore.

Great Family Businesses Need Good Governance

Institute of Corporate Directors, Southwest Ontario presents “Great Family Businesses Need Good Governance”

Ivey Business School's David Simpson discusses governance issues unique to the family-run business. 

 Given their portrayal in the media, it might be easy to dismiss family businesses as hotbeds of power playing, favor currying, and back-stabbing—preoccupations that can hurt the company, the family, or both. But despite the headline-grabbing tales, many family businesses have enjoyed success for decades, even centuries.

 David Simpson, Director and Lecturer, Entrepreneurship, Ivey Business School will speak about Family Business Governance. This event is an opportunity for current directors of boards, business families, and business leaders to gain insights into the real-world challenges of the complexities of family business governance. 

 Join this insightful discussion hosted by the ICD on Governance Lessons from Great Family Businesses.  Whether your company is publicly traded, partly owned by professional investors, or completely family-owned, committing to sound governance practices is essential for sustainable growth and success.

📅Date: 📍 Location:

Date: April 17th

Time: 4:30pm registration and networking, 5:00pm start, 6:00pm cocktails, 6:30pm end

Venue: The Hunt Golf Club, London

Don't miss this opportunity to network with peers and gain valuable insights. Register now and strengthen your knowledge and competence in family business's governance.

RSVP to: jloewen@burgundyasset.com

 David Simpson. Program Director and Lecturer, Entrepreneurship

Expertise: Entrepreneurship, Family Business, Corporate Finance

David Simpson is a London, Ontario-based financier with a broad range of business experiences and a passion for entrepreneurship. He has financed and operated a diverse range of businesses, including restaurants, golf courses, aircraft leasing, oil field serves, and retail.

David completed a B.A. in Political Science through part-time study while he played professional hockey in the New York Islanders organization. Upon retirement from hockey, David completed an MBA at the Ivey Business School, graduating in 1988. Upon graduation, David began a career as an entrepreneur engaging in all aspects of corporate finance in the small business sector.

In 1989, David was the co-founder of The New Enterprise Workshop, one of the earliest attempts (supported by the Ontario provincial government) to support fledgling entrepreneurs. As an operator himself in a family business, David is keen to support Ivey’s efforts to understand and support learning in this vital sector of the Canadian economy. As a practicing entrepreneur, David is passionate to promote this lifestyle choice as Program Director of FamilyShift™, an executive education program for entrepreneurial families.

Jacoline Loewen, ICD.D, MBA

Jacoline Loewen serves as the Director of High Net Worth Relationships at Burgundy Asset Management Ltd., an independent, global investment manager providing discretionary investment management for private clients, foundations, endowments, pensions, and family offices.

Jacoline’s strong passion for entrepreneurship and deep commitment to board involvement developed over two decades of experience in finance, including wealth management, corporate finance, and family office private equity investments. She is also the author of three finance books for business owners - the most recent book titled "Money Magnet" comes recommended by the Richard Ivey School of Business and Toronto Metropolitan University.

For 2023/2024, she was elected President of The Ticker Club. She is a director on the board of The Fraser Institute, and involved with the Institute of Corporate Directors, Southwestern Ontario chapter.  She served 14 years as a director on the board of The Atmospheric Fund, managing $100 million AUM. During her tenure, she chaired both the Strategy and Investment Committees and serving as a member of the Audit Committee. She served as Chair at the OCAD University Imagination Catalyst and a Director on the Board of the PCMA.

Jacoline completed the Institute of Corporate Directors Education Program and has the ICD.D designation from the University of Toronto. She holds a BA in IR from McGill University and a MBA from the University of the Witwatersrand, her MBA thesis was published by Cambridge University UK.

Beyond Rags to Riches: Strategies for Sustaining Family Wealth Across Generations

The saying "from rags to riches in three generations" echoes across cultures worldwide, encapsulating a familiar arc: one generation builds wealth, the next enjoys it, and the third squanders it. This pattern—sometimes called "shirtsleeves to shirtsleeves"—is a cautionary tale rooted in reality for many families. Yet, it’s not an inevitable fate. For families with substantial wealth, there are proven strategies to break this cycle, preserve their financial legacy, and even enhance it over time. So, what are the options to maintain and grow family wealth across generations?

The erosion of wealth often stems from a mix of poor planning, lack of communication, and shifting priorities. But families who defy the odds share common traits: intentionality, adaptability, and a focus on long-term vision. Let’s explore some practical and innovative approaches to safeguarding and building a family’s fortune.

1. Establish a Family Governance Framework

Wealth preservation starts with clarity. A family governance structure—think of it as a constitution for your family’s values and assets—sets the tone for decision-making. This might include regular family meetings, a shared mission statement, or even a formal council to oversee major financial moves. By aligning everyone on goals (e.g., philanthropy, business growth, or legacy investments), families reduce the risk of conflict or drift. The Rothschild banking dynasty, for instance, famously used family councils to maintain cohesion and strategic focus across centuries.

2. Educate and Engage the Next Generation

One of the biggest threats to wealth is an unprepared heir. Too often, the second or third generation lacks the financial literacy or entrepreneurial drive of their predecessors. Counter this by starting early: teach children about money management, investments, and the family’s history of wealth creation. Some families create “mock portfolios” for teens to manage or involve them in charitable giving decisions. Engagement fosters ownership—both literal and emotional—making heirs stewards rather than spenders.

3. Diversify Wealth Streams

Putting all eggs in one basket is a recipe for disaster. Families who thrive diversify their holdings—real estate, private equity, public markets, or even passion projects like vineyards or tech startups. Diversification isn’t just about risk management; it’s about opportunity. Consider the Rockefeller family, who transitioned from oil riches to a sprawling portfolio of investments and trusts, ensuring resilience through economic shifts.

4. Leverage Trusts and Estate Planning

A well-crafted trust can shield wealth from taxes, creditors, and mismanagement. Options like dynasty trusts, which can last for generations, or incentive trusts, which tie distributions to milestones (e.g., earning a degree or maintaining a career), offer flexibility and control. Pair this with regular estate plan updates to adapt to changing laws or family dynamics. The key? Work with advisors who understand your family’s unique story, not just the numbers.

My painting - Forest Trees, Waterolours, 14” x 20”, August, 2024. Ontario, Near Lake Simcoe.

5. Build a Culture of Entrepreneurship

Wealth often fades when families stop innovating. Encourage a mindset of creation over consumption—whether that’s launching new ventures, investing in cutting-edge industries, or mentoring the next wave of leaders. The Mars family, behind the global candy empire, kept their edge by reinvesting profits into new products and markets, balancing tradition with bold moves.

6. Philanthropy as a Unifying Force

Giving back isn’t just noble—it’s strategic. A family foundation or shared charitable mission can unite members across generations, reinforce values, and provide tax benefits. It also offers a training ground for younger relatives to learn leadership and financial oversight. Look at the Gates family: their foundation has not only impacted the world but also cemented their legacy beyond mere dollars.

The Alternative Path

The “rags to riches and back” narrative doesn’t have to be your family’s story. By blending structure, education, and innovation, wealth can become a tool for connection and purpose rather than a fleeting windfall. The families who succeed don’t just avoid catastrophic loss—they turn their resources into a living legacy, evolving with each generation.

What’s your family’s next step? Whether it’s a candid conversation around the dinner table or a call to a trusted advisor, the time to act is now. Wealth isn’t just about what you have—it’s about what

It’s Different This Time: Family Wealth Management in a New World

By Jacoline Loewen
February 25, 2025

“It’s different this time.” Those five words are the most dangerous in investing—a siren call that’s lured many to ruin. They whisper that history’s lessons and the bedrock principles of wealth-building—discipline, diversification, patience—can be tossed aside. But here’s the twist: in the world of family wealth management, it is different this time. Not because the rules don’t apply—they do—but because the societal and economic landscape has shifted so dramatically that families must think and act differently to secure their long-term goals.

For years, I’ve been a "Family First" advocate—practically a cheerleader—helping clients build not just wealth, but legacies. Yet today, the pressures facing families are of a magnitude I never anticipated. Inflation bites harder, technology disrupts faster, and the modern family itself is fraying at the edges. Marriages dissolve, children move far away and drift, global cousins barely know each other. The old certainties—stable unions, tight-knit clans, shared values—are eroding. And with them, the assumptions underpinning family wealth management are being tested like never before.

The Past Still Matters—But the Future Demands More

Success in this new world isn’t about abandoning the best of the past; it’s about preserving it while embracing what I call the "next practice." Compounding still works miracles. Diversification still shields against storms. But clinging to yesterday’s playbook without adapting to today’s realities is a recipe for stagnation—or worse. The families I work with know this: wealth isn’t just numbers on a balance sheet. It’s the family itself—the heart of every decision, the engine of every aspiration.

My role? Helping families articulate and achieve their broader vision—lifestyle, business, education, financial security, philanthropy—while navigating a louder, messier, and more fragmented landscape than ever. I used to believe divorce was rare, drug issues were outliers, and marriages were forever. I was wrong. Changes in the modern family aren’t just possible—they’re inevitable. Children increasingly carve their paths, separate from the family core. Global families stretched across continents, have less time together and fewer shared touchstones with their cousins. Community—the root of happiness—is harder to create and sustain.

My painting - Overlooking Mono Hills, Pastels, 8”x10”. Ontario, near HW 89.

The Non-Financial Key to Multigenerational Wealth

Here’s the issue: the most critical part of family wealth management isn’t financial—it’s non-financial. It’s the education and engagement of the family across generations, bridging divides of age, geography, and values. This may be the wisest investment a family can make—not in stocks or real estate, but in itself. Why? Because wealth is an advantage only if the family stays cohesive enough to wield it. Risk management, succession planning, and long-term preservation all hinge on this.

Picture a family enterprise spanning decades. The portfolio might be stellar—low fees, high returns—but if the kids don’t understand the "why" behind the wealth, if the cousins don’t trust each other if the next generation isn’t engaged, it’s all for naught. I’ve seen it: families fractured by divorce, addiction, or sheer distance, watching their wealth dissipate not from bad investments, but from bad relationships.

Adapting to Thrive

So, what does "next practice" look like? It’s doubling down on the principles that endure—rigorous planning, prudent diversification—while facing the new realities head-on. It’s investing in family retreats to rebuild bonds, in education to align values, in communication to span the generational chasm. It’s recognizing that wealth’s true power lies in giving families freedom and resilience—advantages that shine brightest when the world gets tough.

"It’s different this time" isn’t an excuse to ignore history; it’s a call to adapt with courage. But today, that means leading families through a world where the stakes are higher, the pressures are fiercer, and the rewards—for those who get it right—are greater than ever. Let’s build legacies that last—not just for now, but for generations.

The Wealth Paradox: A Tale of a Canadian Tire Franchise Owner

There he stood, an unassuming figure in a sea of everyday people—yet beneath the surface, he was the king of his own glittering kingdom. Our protagonist, a franchise owner of Canadian Tire and a private equity investor, held the keys to an Aladdin’s Cave of wealth. But you’d never guess it, given the lengths he went to downplay his affluence.

With a whisper, he confided his net worth. A number so astonishing, even Google might struggle to estimate it accurately. Yet, his intent was clear: he wanted the world to believe he was far poorer than reality. Why? To avoid the avalanche of problems that come with being rich.

In a world obsessed with wealth, his affluence had become a burden. Imagine meeting someone new, only to have them ask for an investment in their latest business venture. Picture a distant relative suddenly appearing, pleading for help with debt. Or even closer to home—family members expecting freebies from his Canadian Tire store. And then, there were the changes in behavior, the subtle shifts in how people treated him when they knew about his wealth. To him, being rich was not a blessing but a curse, a weight that occupied his every thought.

And yet, despite this, he found himself chasing more. More wealth, more investments, more success. The irony was palpable. Here was a man drowning in riches, yet he couldn’t stop himself from diving deeper into the pool. It’s a phenomenon many wealthy individuals grapple with—this relentless pursuit of more, even when they already possess an abundance.

Dan Sullivan, the Founder of Strategic Coach, calls this the “Gap and Gain” mindset. It's the idea that wealthy individuals often focus on what they haven’t achieved rather than appreciating what they have. They measure their success against others’ wealth, never pausing to give themselves credit for their accomplishments. It’s a vicious cycle, one that leaves them perpetually dissatisfied.

But let’s take a step back. Wealth, in its truest sense, is a process. It’s not just about the numbers in your bank account, but the journey you’ve taken, the lives you’ve touched, and the impact you’ve made. Our Canadian Tire franchise owner, for all his wealth, had created opportunities, provided jobs, and positively influenced countless lives through his investments and businesses.

Yet, as he stood on the precipice of even greater wealth, one question loomed large: on his deathbed, would he want to be surrounded by his financial statements, or by the people who loved him for who he was, not what he had?

It’s a question every wealthy individual must ponder. The chase for more is never-ending, but the true measure of wealth is found in relationships, experiences, and the legacy you leave behind. Our protagonist’s story is a reminder that wealth is not just about accumulating riches; it’s about recognizing and appreciating the gains, and understanding that sometimes, the greatest wealth lies not in what you have, but in who you are.

So, as we navigate our own journeys to wealth, let’s remember to celebrate our gains, cherish our relationships, and keep our eyes on what truly matters. Because at the end of the day, it’s not the wealth in our bank accounts that defines us, but the wealth in our hearts.

My painting, Bluebells in the Forest, Pastels, 10x12. Ontario, Rosedale.

The Odyssey of Wealth Management: A Human Challenge

In a world where the pursuit of wealth often overshadows the pursuit of wisdom, Homer's *The Odyssey* provides a tale of adventure and return and a profound narrative on stewardship of wealth across generations. Despite his kingly status, Odysseus does not navigate through his epic journey with wealth at the helm but with human resilience, strategic thinking, and the undying quest for identity and belonging. This ancient tale resonates deeply with the modern challenge of wealth management, particularly the challenge of the rising generation.

The Challenge Isn't What You Think

Research and my observations in the field of wealth management reveal that the core challenge isn't about the money itself. It's not about the complexities of investments, nor is it primarily a legal or logistical conundrum. Instead, it's a deeply human issue. The real challenge lies in overcoming the silence that often envelops family wealth, particularly when it comes to the next generation.

In many wealthy families, there exists an unspoken rule: wealth is to be seen but not discussed. This silence can lead to a lack of understanding, unpreparedness, and sometimes, resentment. Here’s what I've heard in the echo chambers of high net-worth families:

• "I was never taught how to manage this; it was just handed to me."

• "There's no talk about expectations, only obligations.I am expected to do an MBA,and work elsewhere for five years, etc. What if I want to be an artist?"

• "How can I find my path when this wealth casts such a long shadow?"

Unpacking the Human Challenge

Breaking the Silence: The first step is to foster open communication. Wealth, like any significant family matter, should be discussed with honesty and openness. Ask your wealth manager to invite your family to events they are holding. Go to workshops together. Ask your wealth manager to hold family meetings at their office. These are baby steps to changing the family dynamic. Even informal gatherings where financial literacy and family values are discussed can begin to break down these barriers.

1. Empowering the Rising Generation: Education is crucial, but not just in the financial sense. The rising generation needs to be educated in the ethos of the family, its legacy, and its responsibilities. This involves:

   • Financial Literacy: Understanding investments, taxes, estate planning, but through a family lens.

   • Leadership and Identity: Helping them carve out their own identity while appreciating the family's heritage.

2. Creating a Voice: Each member of the rising generation must find their voice within the family's narrative. Easier said than done! This isn't about conformity but about creating a dialogue where each individual can express their vision for the future, their concerns, and their innovations. Don’t wait for the wealth creator to start this.

3. Mentorship Over Monologue: Instead of a top-down approach to wealth transfer, mentorship from older generations to the younger ones can be transformative. It's about listening, guiding, and adapting to new ideas that the young bring to the table.

4. Legacy Beyond Wealth: What does the family stand for? How can wealth be a tool for societal good? Engaging in philanthropy or social enterprise can give the rising generation a sense of purpose and a platform to exercise their values.

The Odyssey Lessons

Odysseus's journey back to Ithaca wasn't just about returning home; it was about reclaiming his identity, his leadership, and his place within his family and society. Similarly, the journey of wealth management for families is an odyssey of its own. The rising generation must navigate through personal growth, societal expectations, and the legacy of wealth with courage. Keep a copy of The Odyssey close by to keep on the journey. In the end, managing family wealth isn't just about numbers on a balance sheet. It's about nurturing the human spirit, ensuring that each generation not only inherits wealth but also the knowledge, values, and voice to use it wisely. Like Odysseus, they must learn to lead, to listen and to find their way home, not just to a place, but to a purpose.

From my sketchbook, Goldfish, watercolour and ink, 8” x 10”. Ontario, Rosedale.

You Have Choices

It was serendipity that I bumped into the sons of a remarkable entrepreneur I have known for decades. Let’s call him James. He built his company to become a towering giant in the food industry, winning industry awards by the dozen, and had recently retired. James had mentioned his three sons and told me they worked in the family business but that they would go on to do their own thing. As I chatted with them at a Family Office event, it was evident that they were now in control of the wealth created by James. They were young Vikings, tall, confident, and with their father’s strong spirit and twinkling eyes. I was glad to see their confidence in taking over the family office because, for many “Rising Gens”, they do not get to this stage of independence. Rather, they get stuck in their father’s shadow and feel guilty and forced to live a pre-determined life.

Hello, future stewards of wealth! This isn't just another lecture on managing your inheritance; it's a conversation about empowerment, choice, and personal growth. As someone who has observed the dynamics of wealth across generations, I want to share insights that will encourage reflection and perhaps prompt action.

The Illusion of No Choice

One of the most pervasive myths in families of wealth is the notion that choices are predetermined by those who came before you. This can force a life lived under the shadow of expectations, similar to what we've observed in royal families like the British monarchy. Prince Charles, now King Charles III, has lived much of his life under the immense gaze of public and familial expectations, as have his sons, William and Harry.

In your own life, you might feel that your career, lifestyle, or even personal relationships have been influenced or decided by the wealth your family has accumulated. This can breed a sense of helplessness, making you feel like you're merely a custodian of wealth rather than a creator of your own destiny.

The Burden of Expectations

From my own family's experience, I've seen how the weight of expectations can stunt personal growth. I was shocked by some family members who at 40, were still grappling with issues they faced at 20, unable to move forward because they were too focused on living up to the legacy of the wealth creator. In comparison, James had asked his sons to figure out their own lives and how to manage the family wealth. The sons had agreed to do “family wealth” and had been given that choice. They also had made the decision not to be part of the family business but to pass it to professional management.

Inheriting great wealth sounds wonderful. It isn't just about money; it's about identity, self-worth, and autonomy. The real challenge isn't managing the financial assets but overcoming the belief in your capacity to forge your path.

Taking Action: Your Role in Shaping Your Future

Here's where the narrative shifts for you from passive acceptance to active engagement:

Understand the Commonality: Recognize that feeling trapped by wealth is not unique to you. Many in similar positions struggle with similar issues. This understanding can be liberating because it means there's a path forward, trodden by others.

• Embrace Your Agency: Wealth doesn't dictate your life unless you allow it to. You have the choice to innovate, to start ventures, to invest in what you believe in, or to use your resources for social good.

• Seek Knowledge and Guidance: Don't wait for the wealth creators in your life to hand you a manual on life. Educate yourself about finance, but also about psychology, leadership, and personal development. Engage with mentors who can guide you beyond just wealth management.

• Redefine Wealth: Look at wealth not just as money but as an opportunity for impact. How can you use what you have to create something meaningful? Whether it's through philanthropy, environmental initiatives, or cultural contributions, your wealth can be a tool for positive change.

• Build Your Own Legacy: What do you want to be known for? Not just as an inheritor but as an innovator or a leader managing your own direction, right? This thought should drive your daily actions. Wealth can be both a blessing and a curse, but the real curse is believing you have no control over it. You're not just the next generation of wealth; you're the next generation of thinkers, leaders, and changemakers. By choosing to engage actively with your circumstances, you can transform inherited wealth into a legacy that reflects your values and vision.

So, as you manage your family wealth, reflect on your current path, take action where you see fit, and remember, the greatest wealth you can accumulate is the richness of a life lived by your design, not by default. Here's to your journey in redefining wealth for you. Stay curious and as Steve Jobs said, stay humble.

Jacoline Loewen, Board Director, Wealth Management, Author of ‘Money Magnet’