So, You Think You’re Ready to Retire? 10 Questions That Could Solidify or Reshape Your Entire Timeline
You’ve worked hard, built something significant, and are now staring down the runway to retirement. But even for Canada’s most financially successful individuals — especially business owners and high-net-worth families — retirement readiness is about far more than portfolio performance or the number on your last financial statement.
True readiness isn’t just financial. It’s personal. It’s emotional. And for those who’ve built wealth through decades of entrepreneurship, it’s also strategic.
While wealth creates opportunity, it also adds complexity. If you're approaching the next chapter of your life, these 10 questions — rooted in current Canadian financial realities — can help ensure your retirement plan is not only viable, but visionary.
1. How much do I really need to retire comfortably in Canada in 2025?
According to a 2025 BMO retirement study, Canadians now estimate they’ll need $1.54 million to retire. But for UHNW households with second homes, international travel, philanthropic goals, and multi-generational planning, that figure can be dramatically higher.
Factor in rising life expectancies and persistent inflation (~2.6% in early 2025), and the “magic number” you had in mind a few years ago may no longer hold up. Retirement is not a static target — it’s a moving landscape that demands active recalibration.
2. What happens to my retirement plan if the market crashes right after I stop working?
This is one of the most underappreciated risks facing retirees: the sequence of returns. If the market dips early in your retirement and you begin drawing income, those withdrawals can permanently impair your portfolio’s growth — even if the market later recovers.
After the turbulence of 2022 and 2023, this risk is no longer theoretical. In response, many high-net-worth Canadians are adopting strategies such as keeping two to three years of low-risk cash equivalents, using GIC ladders for income stability, and layering withdrawals from various account types to reduce volatility exposure in the early years.
Reach out to your advisor to discuss strategies that suit your unique situation.
3. Do I need to sell my business to retire — or can I keep my corporation and still generate income?
You don’t have to sell to retire. Many entrepreneurs retain their corporation to extract surplus over time or shift into a governance-only role.
That said, without proper planning, you could:
Trigger significant capital gains tax if you sell suddenly
Face double taxation on retained earnings if they pass through your estate
Miss out on the Lifetime Capital Gains Exemption (LCGE), which can shield up to $1.25 million of gains on eligible small business shares
For business owners, retirement and succession planning must go hand-in-hand.
4. What’s the smartest way to take income in retirement without triggering higher taxes or OAS clawbacks in 2025?
Most UHNW Canadians have at least four retirement income sources:
RRSPs/RRIFs, TFSAs, non-registered investments, and possibly corporate distributions.
Without coordination, you may:
Push yourself into a higher marginal tax bracket
Trigger a clawback of your Old Age Security (OAS) — which begins at $93,454 of net income in 2025
Leave certain accounts inefficiently taxed in your estate
A strategy may involve:
Withdrawing modestly from RRSPs pre-71 to smooth taxable income
Using corporate surplus to fund post-65 dividends, taxed at lower effective rates
Prioritizing TFSA growth for late-retirement liquidity or legacy
5. What if I get sick or lose capacity during retirement — is my spouse or family ready to step in?
Longevity brings with it a higher likelihood of health challenges. According to the Canadian Institute for Health Information (CIHI), one in four Canadian seniors over age 85 lives with diagnosed dementia. Many more experience some form of cognitive decline before end-of-life.
Planning for this includes more than just having a Will. Ask yourself:
Do I have updated powers of attorney (POAs) in place?
Is my spouse financially literate and empowered to manage our plan?
Have I documented key contacts, intentions, and asset locations?
Too often, these conversations only happen after a health event — when it's too late.
6. When should I update my estate plan — and what needs to change now that I’m retiring?
Many people view their Will as a “set it and forget it” document. But retirement changes the way your estate should function. Your income sources shift. Your asset ownership evolves. Your goals — for legacy, tax efficiency, and family support — often grow more nuanced.
You may need to reassess beneficiary designations, consider the liquidity required to fund taxes on real estate or private shares, and revisit the role of trusts or charitable giving in your legacy. Retirement isn't the end of estate planning — it's the beginning of a more refined phase of it.
7. Am I ready to let go of my business — or will I regret stepping away?
For entrepreneurs, stepping back isn’t just a financial shift — it’s an emotional transition. The business may have been your identity, your purpose, and your community. Walking away can create a void.
That’s why many WealthCo clients are opting for a phased retirement: taking advisory roles, mentoring successors, or shifting into philanthropy or board service. The transition doesn’t have to be abrupt. With proper planning, your “second act” can be just as fulfilling as your first.
8. Have I had the “retirement talk” with my spouse and family — or am I assuming we’re on the same page?
One of the most common sources of friction during retirement isn’t financial — it’s relational. Misalignment between partners on where to live, how often to travel, or how much to support children can cause stress if not discussed early.
More families in 2025 are also choosing to hold structured family meetings to discuss inheritance expectations, philanthropic priorities, and intergenerational values. This kind of communication doesn’t just prevent conflict — it strengthens your legacy.
9. How do I leave a meaningful legacy — not just money?
Retirement gives you the time and resources to think about your impact. For some, that means establishing a charitable foundation. For others, it means beginning to gift wealth during their lifetime, helping children or grandchildren while they're still in formative stages.
A growing number of Canadians are also using corporate life insurance to create tax-efficient inheritances and fund charitable goals — particularly through strategies that leverage the Capital Dividend Account (CDA).
Ultimately, the most meaningful legacy is intentional — not accidental.
10. Has my retirement plan evolved with my life — or is it based on outdated assumptions?
The retirement landscape has changed in 2025. If your plan was created five or ten years ago, it may not reflect current tax rules, market dynamics, or even your own family’s evolving needs.
Dynamic planning means reviewing your strategy regularly. It means integrating your business holdings, insurance coverage, estate plan, and investment strategy — not managing them in isolation. Most of all, it means having a professional team who understands how the pieces fit together.
Final Thought
If these questions caused you to hesitate — that’s a sign you're taking retirement seriously. For the ultra-successful, retiring “on paper” is one thing. Doing it with clarity, control, and confidence is another.
If you’re facing these questions now, or know they’re around the corner, reach out to your WealthCo advisor. Let’s ensure your next chapter is backed by strategy, not assumption.
Disclaimer: The information in this article is for informational and educational purposes only and is not meant to be construed as financial advise. Please consult with a qualified financial advisor before making any financial decisions.
Ready to reach out?
Share your financial goals with us today, and we’ll match you with a Private Wealth Advisor to provide expert, tailored guidance for your unique financial needs.
