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Retirement
Planning &
Investment

A secure retirement doesn't happen by accident. It requires a plan built around your life, your timeline, and the unique complexities of living or working across the Canada–US border. We build that plan — and manage it with you, every step of the way.

RRSP & 401(k) Tax-Smart Investing Cross-Border Planning
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15+
Yrs Experience
360°
Holistic View
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RRSP & TFSA 401(k) & IRA Investment Strategy Retirement Income Cross-Border Pension CPP & OAS Portfolio Management
RRSP & TFSA 401(k) & IRA Investment Strategy Retirement Income Cross-Border Pension CPP & OAS Portfolio Management
02

Planning for the Life
You Want

From accumulating wealth to distributing it tax-efficiently in retirement — we cover every phase of your financial journey.

Comprehensive Retirement Plan

A written, personalized retirement plan covering your target retirement date, savings targets, expected income sources, lifestyle expenses, and strategies to bridge any gaps.

RRSP & TFSA Optimization

Maximizing your registered accounts — RRSP contribution room, spousal RRSP strategies, TFSA investment choices, and the optimal sequence for contributions and withdrawals.

Retirement Income Planning

Designing a tax-efficient income stream in retirement — blending RRSP/RRIF draws, CPP, OAS, non-registered investment income, and corporate dividends to minimize lifetime tax.

CPP & OAS Optimization

Determining the ideal age to start CPP and OAS — factoring your health, other income, break-even analysis, and whether deferral to age 70 makes financial sense for your situation.

RRSP-to-RRIF Conversion Planning

Planning the mandatory RRSP-to-RRIF conversion (by age 71) — with optimal drawdown strategies to avoid OAS clawbacks and minimize the tax impact of minimum withdrawals.

Corporate Retained Earnings Planning

For business owners — using your corporation as a retirement savings vehicle through the strategic timing of salary, dividends, and retained earnings drawdowns in retirement.

Investment Policy & Strategy

A written investment policy statement defining your goals, risk tolerance, time horizon, asset allocation targets, and the benchmarks we'll use to measure performance.

Asset Allocation & Diversification

Building a diversified portfolio across equities, fixed income, real estate, and alternatives — balanced for your risk profile and optimized across your registered and non-registered accounts.

Tax-Smart Portfolio Construction

Placing investments in the right accounts — interest-bearing assets in registered accounts, Canadian dividends in non-registered accounts, and US equities managed for treaty withholding efficiency.

Portfolio Reviews & Rebalancing

Regular portfolio reviews — at minimum annually — with rebalancing to maintain target allocations as markets move and your life circumstances evolve.

Tax-Loss Harvesting

Strategically realizing capital losses in non-registered accounts to offset capital gains — reducing your current tax bill without compromising your long-term investment strategy.

Consolidated Portfolio Reporting

Clear, consolidated reporting across all your accounts — registered, non-registered, Canadian, and US — so you always see the complete picture of your wealth.

RRSP / 401(k) Cross-Border Strategy

Coordinating Canadian RRSPs and US 401(k)/IRA accounts under the Canada–US Tax Treaty — including deferral elections, contribution strategy, and tax-efficient withdrawal sequencing across both.

CPP / OAS & Social Security Coordination

Managing the interaction between Canadian CPP/OAS and US Social Security for cross-border individuals — including Totalization Agreement benefits and Windfall Elimination Provision planning.

Multi-Currency Retirement Income

Managing retirement income in both CAD and USD — FX strategy, cross-border banking optimization, and currency risk management to protect your purchasing power in retirement.

Snowbird & Residency Planning

For Canadians spending extended time in the US — managing the 183-day substantial presence test, treaty tie-breaker rules, and the investment implications of split-residency retirement.

Pension Transfer & Portability

Advising on pension transfer options when relocating — Locked-In Retirement Accounts (LIRA), pension commutations, and portability of defined benefit entitlements across borders.

Cross-Border Real Estate in Retirement

Planning for US vacation property owned by Canadian retirees — rental income treatment, estate tax exposure, and exit strategies to minimize withholding on sale proceeds.

03

Registered Account
Comparison

Understanding how each account works — and where it fits in your plan — is the foundation of tax-efficient wealth accumulation.

Canadian

RRSP

Registered Retirement Savings Plan

Contributions tax-deductible
Growth tax-deferred
18% of prior year income (max ~$31K)
Withdrawals fully taxable
Must convert to RRIF at age 71
Best for

High earners in peak earning years

Canadian

TFSA

Tax-Free Savings Account

Growth completely tax-free
Withdrawals tax-free, anytime
Withdrawn room re-added next year
No age limit, no mandatory withdrawals
Treated as taxable by IRS (US persons)
Best for

All Canadians — especially lower income years

US

401(k) / IRA

US Employer Plan / Individual Retirement Account

Pre-tax contributions (Traditional)
Roth option: tax-free growth
Employer match (401k)
RMDs from age 73
10% penalty on early withdrawals
Best for

US-based employees with employer plans

CA & US

Non-Registered

Taxable Investment Account

No contribution limits
Capital gains taxed at 50% inclusion
Canadian dividends — dividend tax credit
Investment income taxed annually
Fully flexible, no lock-in
Best for

After all registered room is maximized

Planning at Every
Life Stage

Retirement planning looks different at 30 than it does at 55. We meet you where you are — adapting the strategy as your income, family, and goals evolve over time.

The Earlier You Start, the More Compounding Works For You

A 30-year-old saving $500/month at 6% average return accumulates approximately $1,000,000 by age 65. The same saving starting at 45 produces roughly $250,000. Time is the most valuable asset in retirement planning — we help you use it wisely.

Age 25–35 Foundation Stage

Start RRSP & TFSA contributions, establish emergency fund, create an investment policy, begin compound growth. Focus on maximizing employer matches and debt elimination.

Age 35–50 Accumulation Stage

Peak earning years — maximize registered contributions, consider corporate retained earnings strategy, optimize tax-sheltered growth, review asset allocation regularly.

Age 50–65 Pre-Retirement Stage

Shift to capital preservation, finalize CPP/OAS timing decisions, plan RRSP drawdown strategy, model retirement income scenarios, review risk exposure in portfolio.

Age 65–71 Early Retirement

Begin CPP/OAS (or defer), activate retirement income plan, start RRSP/corporate drawdowns, manage OAS clawback thresholds, convert RRSP to RRIF by age 71.

Age 71+ Distribution Stage

Mandatory RRIF minimum withdrawals, manage longevity risk, integrate with estate plan, optimize wealth transfer to heirs through TFSA and non-registered strategies.

04

The T&F Difference

Retirement planning done in isolation from your taxes, corporate structure, and estate plan is incomplete. We see the whole picture — and plan across all of it.

Fully Integrated Planning

Your retirement plan connects directly to your tax filings, corporate structure, and estate plan — so every decision is made with the full financial picture in view, not in silos.

Cross-Border Specialists

We understand both Canadian and US retirement systems — RRSP deferral elections, treaty-based Social Security treatment, and the interaction between CPP and US pension income.

One Dedicated Advisor

A single professional who knows your entire financial life — your income, your assets, your goals, and your family — providing consistent advice over decades, not just one-off recommendations.

Tax-First Investment Lens

Every investment recommendation is filtered through a tax lens — because the after-tax return is the only return that matters. Asset location, account types, and withdrawal sequencing are always tax-optimized.

Ongoing Plan Adjustments

Life changes — income, family, health, markets, and legislation all evolve. We review and update your retirement plan annually to keep it aligned with where you actually are.

Free Retirement Readiness Review

Not sure if you're on track? We'll review your current savings, projected income, and retirement timeline — at no charge — and show you exactly where you stand.

Book a Free Review

Planning Packages

Engagements tailored to your life stage and complexity. All packages include an annual review and plan update.

Foundation

Early Accumulator

For individuals in their 20s–40s building the foundation of their retirement savings.

Retirement goal projection
RRSP & TFSA strategy
Investment policy statement
Asset allocation recommendation
Annual review & update
Get a Quote
Cross-Border

Dual-Jurisdiction
Retirement

For individuals with retirement accounts, pensions, or residency considerations in both Canada and the US.

Everything in Comprehensive
RRSP / 401(k) coordination
CPP & Social Security strategy
Multi-currency income planning
Snowbird residency guidance
Get a Quote
05

Frequently Asked
Questions

Retirement planning involves decisions that will shape decades of your life. Here are the questions we hear most often — and we're always available to talk through yours.

Ask Us Anything
It depends on your current and expected future tax rate. If your income is high now and you expect to be in a lower bracket in retirement, RRSP contributions deliver the greatest benefit — you defer tax at a high rate and withdraw at a lower rate. If you're in a lower bracket now, or expect similar income in retirement, the TFSA often wins because your withdrawals are completely tax-free. Ideally, contribute to both — but the sequencing matters, and we help you optimize it.
You can take CPP as early as age 60 (reduced by 7.2% per year before 65) or defer as late as age 70 (increased by 8.4% per year after 65). The "break-even" point for deferral is typically around age 83–84. If you're healthy and have other income sources, deferring to 70 often delivers the most lifetime benefit. If you have health concerns or need income sooner, taking it earlier makes sense. We model both scenarios for your specific situation.
RRSP and RRIF withdrawals count as taxable income, which can trigger the OAS clawback (also called the OAS Recovery Tax) if your net income exceeds approximately $90,000 (2024 threshold). For every dollar above this threshold, OAS is reduced by $0.15. Proactive planning — such as drawing down the RRSP strategically before OAS begins, or spreading income sources across spouses — can preserve your full OAS entitlement.
You can generally leave your 401(k) in the US plan, roll it to an IRA, or in some cases transfer it to your RRSP (subject to limits). Most Canadians with US 401(k) plans choose to leave them in the US or roll to an IRA. Under the Canada–US Tax Treaty, you can elect to defer Canadian taxation on the 401(k) until you actually take withdrawals — but this election must be made on your Canadian tax return. We handle this coordination regularly.
The traditional "25x your annual expenses" rule (the 4% withdrawal rate) is a useful starting point — if you need $80,000/year, you'd target $2 million in savings. But this doesn't account for CPP, OAS, pensions, tax rates, inflation, healthcare costs, or longevity. We build a personalized retirement income model that incorporates all your income sources and gives you a far more precise and actionable target.
Yes — and for many incorporated business owners, this is one of the most powerful retirement strategies available. By retaining earnings in your corporation and investing them there, you defer personal tax while your investments compound. Then in retirement, you control the timing and amount of salary, dividends, and capital gains you draw from the corporation — managing your tax bracket year by year. This is best combined with a HoldCo structure for maximum flexibility.

A Plan Built for Your Life.
Not a Generic Template.

Whether you're just starting out, approaching retirement, or navigating a cross-border situation — we build a retirement plan that fits your real life, integrates with your taxes, and adapts as you grow.

(647) 528 0200 info@bobbyfinancials.ca ON & NY