Building your retirement roadmap: Key Insights & Actionable Strategies

Build confidence in your independence and legacy

Knowing when you have reached financial independence is the turning point between accumulation and transition. Allan described this moment as both technical and emotional. “Once you know you’re financially independent, you can start thinking about how to build confidence in your legacy and what you want to leave behind.”

He advised defining independence first. The point where assets can sustain your desired lifestyle, then moving on to intergenerational considerations such as succession, gifting, or philanthropic intentions.

Clarity about independence brings confidence. Once you know your foundation is secure, you can make legacy decisions from a place of purpose rather than pressure.

Align your giving with your values

Hayley Maschek shifted the discussion toward philanthropy, emphasizing that charitable planning is as personal as any other part of wealth management. For most families, she explained, the motivation comes down to impact and legacy, whether it’s driven by altruism, a desire to bring family together, or the opportunity to make a difference across generations.

She added that thoughtful planning can make giving even more effective. “From a tax efficiency standpoint, it does matter the types of assets that we might be giving. The same dollar amount that we’re giving away or foregoing could have a more significant charitable impact if we can reduce that tax leakage.”

For example, she noted that donating certain types of capital property can eliminate tax on gains entirely. “There are certain types of capital property that aren’t subject to any capital gains tax and is therefore a common and effective way to give. To access this benefit, the property must be donated directly to the charity.”

Maschek also pointed to private foundations as an option for families looking to create structure around their giving. These, she explained, can fund scholarships, support conservation work, or help build schools. “The sky’s the limit, as long as what you intend to do is viewed as charitable in nature.”

Strategic giving turns generosity into legacy. Integrating philanthropy with your financial plan can enhance both impact and efficiency, while connecting your family through shared values.

Create a structure that lasts

Long-term giving works best when it has structure and flexibility, Malcolm Burrows noted. “I always distinguish with clients the difference between ordinary charitable giving that most of us do on a regular basis, on an annual basis, from income, as opposed to more strategic charitable giving, where we’re integrating philanthropy with wealth planning.”

He explained that the best time to give is often when your tax burden is highest. “For example, if you’re a business owner selling your company, there’s a very significant tax bill at that time, and that’s one of the best times to offset it, and also a good time to be thinking about something like a donor-advised fund or a private foundation.”

Burrows described donor-advised funds as a flexible way to plan for long-term generosity. “People use donor-advised funds because it concentrates it all in one place. You have a single structure, like a family foundation, where you can focus your planning, figure out the right asset to give, and decide what makes the most impact.”

He added that these structures keep families involved in meaningful, ongoing giving. “Each and every donor-advised fund represents a family and their interests. Unlike traditional charitable giving, where once it’s given it’s gone, you get to be involved on an ongoing basis, have your children involved, and change your mind as you go.”

“It’s not about limiting options, it’s about opening them up so you can pour yourself into it, engage with your community, and really have that profound impact.”

Building structure into your giving creates consistency and impact. Flexibility allows generosity to evolve as your circumstances and goals shift.

Review your roadmap with the right people

All three speakers agreed that collaboration makes every plan stronger. Financial, legal, and philanthropic advisors each provide a piece of the puzzle, ensuring that tax, estate, and investment strategies work together. Open discussions with family also create shared understanding and prevent uncertainty later.

A roadmap becomes more than numbers when everyone involved knows the direction, values, and intentions behind it. And, with a coordinated plan, you reduce blind spots. Bringing everyone to the same table helps uncover new opportunities and safeguards your future.

Turn insight into action

Putting your roadmap into motion doesn’t have to be complicated. Start with practical steps that keep your plan flexible and aligned with what matters most to you:

• Review your roadmap annually: Test different scenarios, update assumptions, and confirm whether your plan still supports your goals and lifestyle.
• Bring your advisory team together: Meet with your accountant, financial advisor, and legal counsel to ensure your investment, estate, and giving strategies work in sync.
• Revisit your independence threshold: Check that your assets still sustain your desired lifestyle, especially as markets, health, or family dynamics change.
• Align your giving with purpose: Assess whether your philanthropic approach, from donations to donor-advised funds, ensuring they still reflect your personal and family values.
• Communicate your vision: Share your plan with family or business partners so everyone understands your intentions and long-term goals.

Take the next step

Your retirement roadmap is more than a financial plan, it’s a guide for how you want to live, give, and be remembered. By reviewing it regularly, aligning it with your values, and engaging trusted advisors, you can move toward retirement with confidence and clarity.

To learn more about building a roadmap that reflects your goals, contact Allan Broudno at [email protected] or Hayley Maschek at [email protected]