For many high-achieving professionals, May isn’t a time to slow down—but it is a time of shifting perspective. The calendar is filled with life events—graduations, weddings, aging parents, and new relationships—that prompt reflection and quietly signal it’s time to revisit the bigger picture.

At Rubach Wealth, we see these moments not just as milestones, but as strategic cues. Because behind every transition lies a ripple effect—and your financial life deserves more than a passing glance. It deserves realignment.

Greg’s Story: A Life in Motion

Greg* is a 55-year-old senior partner at a Bay Street law firm. He’s recently divorced, owns his Toronto home mortgage-free, and pays monthly spousal support. His daughter, Emma, is getting married this summer. His mother, now in assisted living, requires financial support. And five years from now, Greg hopes to retire.

Greg also owns a condo in Palm Springs, and he is in a serious relationship, and considering having his partner move in.

Greg’s goal is clear: take care of everyone who matters—without losing his stability in the process. But like many high-net-worth professionals, his life has grown more complex than his current plan accounts for.

1. A New Relationship and a Need for Clarity

Greg is in a new long-term relationship. They’re talking about moving in together, but haven’t discussed what that means legally or financially.

We helped Greg:

• • Update his will, POAs, and beneficiary designations post-divorce
  • Understand the implications of cohabitation on his assets and estate
  • Explore how joint ownership or future entanglements could affect his daughter’s inheritance 

At this stage of life, protecting your future means thinking ahead—not just for yourself, but for everyone connected to you.

2. Becoming the Caregiver

Greg’s mother recently moved into assisted living. While emotionally tough, it also introduced a new financial layer into Greg’s life—one that could impact his own retirement if left unaddressed.

Together, we:

• Adjusted his retirement projections to include elder care support
• Created a contingency fund to absorb increasing long-term care costs
• Initiated early planning around his own future care needs 

Supporting two generations requires strategy, not just generosity.

3. The Condo in Palm Springs: Dream Realized, Risks Emerging

Greg’s condo in Palm Springs has become his sanctuary. But as retirement planning and estate considerations move to the forefront, new risks are surfacing—especially in light of the evolving Canadian–U.S. relationship.

He hadn’t fully considered:

• The potential U.S. estate tax exposure for Canadian property owners
• How Emma would inherit the condo—and the cross-border tax implications she could face
• Whether the property should be held personally, corporately, or in trust to minimize risk 

With shifting tax policies and growing uncertainty around cross-border regulations, what began as a joyful escape now needs to be treated as part of a strategic international estate plan. Left unaddressed, it could become a costly complication instead of a lasting legacy.

4. A Daughter’s Wedding—and a Complicated Gift

Emma’s wedding is fast approaching. Greg wants to help—but her fiancé carries significant student loan debt. Greg is proud of Emma’s independence and wants to support her without jeopardizing her financial foundation—or enabling avoidable risk.

We helped Greg:

• Make a contribution to Emma’s TFSA as a structured gift
• Explore trust options for future inheritance
• Start a values-based conversation with Emma about responsibility, boundaries, and legacy 

For many of our clients, the real challenge in supporting adult children isn’t just the money—it’s teaching practical, grounded approaches to managing it well.

5. Retirement Is Coming, But It Looks Different Now
Greg has equity in his firm and plans to retire in five years. But with new financial obligations, a second home, and blended family dynamics emerging, we re-evaluated everything from withdrawal strategies to lifestyle goals.

We helped him:

• Plan for the timing and tax implications of his firm’s partnership payout
• Rebalance his portfolio for greater flexibility
• Stress-test his goals to ensure he could fund retirement, support loved ones, and maintain personal freedom
  

Even the most experienced professionals benefit from fresh eyes when life changes.

Staying Whole in a Shifting Life
Greg’s story isn’t rare—it’s increasingly common among our clients. You’re managing aging parents, adult children, new relationships, real estate across borders, and your own aspirations. The complexity isn’t a problem. But ignoring it might be.

“The goal isn’t just to protect your wealth—it’s to protect your peace of mind. To look after others, without losing yourself.”

That takes more than intuition. It takes integration.

This May, Ask Yourself:

• Does my current plan reflect my current reality?
• Are all the moving parts—family, property, retirement, estate—working together?
• Have I accounted for what’s changed in the past year?

Milestones don’t just deserve reflection. They deserve action.

At Rubach Wealth, we help high-net-worth professionals turn life’s transitions into clear, confident plans.

Let’s talk.

Names and identifying details have been changed to protect privacy.