How to Intentionally Design Your Financial Plan For The Next Few Years 

When some advisors sit down with clients to discuss their finances, the conversation might begin with performance reports, tax strategies, and risk tolerance. Granted, those are essential elements of financial planning. But elements alone don’t make a life.

Our focus is very different. For many of our clients – whether long-married couples redesigning retirement or widows navigating a newly independent chapter – the most important question isn’t “How am I doing compared to the market?” It’s a quieter, more personal one:

What is this money meant to make possible?

Starting with our first meetings, we want to know what achievements would make you feel good about your progress three years out. We ask about any obstacles that could jeopardize that progress. We help you identify what truly excites you, so we all focus on the right prize. And we ask what’s going right, so we get more of that.

Our purpose? To be sure our efforts together are tailored uniquely to your life and achievable to implement.

The next three to five years represent a valuable planning window. You’re close enough to act but far enough away to design intentionally. We like the concept of ‘vision casting’ to bridge that gap: treating your wealth not as an abstract scorecard but as a tool that supports how you want to live, contribute, and feel in the years ahead.

Redefining ‘Enough’: What Your Lifestyle Actually Requires

By their late 60s, Dot and Paul had achieved financial stability but kept putting off decisions. Their home had long been the family hub: holidays, visits, constant upkeep. When they imagined an ordinary weekday five years out, the house faded into the background. What mattered more was energy, flexibility, and the ability to say ‘yes’ when family called. Downsizing didn’t feel like giving something up; it felt like choosing how they wanted to spend their time.

In traditional financial planning, ‘enough’ is often reduced to a single number. In real life, however, ‘enough’ is situational. It depends on how you want your days to unfold – and on which responsibilities you want to keep, simplify, or release.

Rather than asking, “Can I retire?” a more useful question is:

What does my day need to look like for me to feel content, useful, and unburdened?

For some clients, ‘enough’ means downsizing. It may mean trading a large family home for a low-maintenance condo, freeing up both capital and mental bandwidth. For others, it can mean preserving the family gathering place, even if it requires higher ongoing costs.

Here’s a practical exercise we sometimes use to get the creative juices flowing:

Describe a typical Tuesday five years from now.

Not a vacation day. Not a milestone event. A normal day.

• Where do you wake up?
• Who do you interact with
• How much structure do you want?
• What feels optional, and what feels essential?

Once that day is clearly defined, we can quantify the cost of supporting it sustainably. That becomes the foundation of your plan: not a market assumption or a generic withdrawal rate, but the real life you want to protect.

Where Will You Go – and Why?

At 70, after losing her spouse, Lorraine spoke of travel as a way to stay busy. Over time, her vision sharpened. She didn’t want constant movement; she wanted familiarity without obligation. A place to return to, slowly learn, and feel at ease. That distinction changed the planning conversation, shifting the focus from occasional trips to steady, sustainable access.

Travel often comes up early in retirement conversations, but vague aspirations – such as “We want to travel more” – don’t help with planning. Time horizon matters.

A three-to-five-year view allows us to differentiate between:

• Experiential travel (extended stays, cultural immersion, multi-generational trips), and
• Logistical travel (visiting family, maintaining dual residences, supporting philanthropic commitments).

We increasingly see clients shift toward slow or purpose-driven travel, spending months rather than weeks in one place. Or maybe coordinating meaningful trips that include children or grandchildren. These experiences carry different cash-flow and tax implications than traditional vacations, especially if they overlap with rental income, foreign residency rules, or healthcare considerations.

For others, the coming years aren’t about going elsewhere at all. They’re about becoming more deeply rooted: serving on nonprofit boards, mentoring, or stepping into community leadership roles. These commitments often carry ‘invisible costs’: travel, attire, hosting, or simply the opportunity cost of time.

Identifying these priorities early allows us to plan for them deliberately, rather than fitting them in after the fact.

Life Goals with Financial Footprints

At a family gathering, the conversation turned to housing costs and student debt. Jim and Rita realized they could make a meaningful difference in their son Sean’s life now rather than someday. By planning ahead, they could offer support without jeopardizing their own financial security. The real gift wasn’t just financial – it was the freedom to say ‘yes’ with confidence.

Many of the most meaningful goals don’t show up neatly on a balance sheet. However, they leave financial traces that deserve careful planning. Here are some ideas:

1. Supporting education without jeopardizing your financial stability. Helping grandchildren graduate debt-free or easing the burden on adult children is a common goal among families with significant assets. The question isn’t ‘whether’ to help, but ‘how.’

Timing matters. Structure matters. And clarity matters – especially when multiple grandchildren or blended families are involved. By mapping educational support in advance, we avoid sudden liquidity pressure and unintended inequities.

2. Giving with intention, not just efficiency. Philanthropy often begins with tax strategy, but it shouldn’t end there. The years ahead offer an opportunity to move from reactive giving to intentional impact.

Whether that means using a Donor-Advised Fund (DAF) as a family teaching tool, supporting a cause over time, or formalizing giving through trusts or foundations, vision casting helps ensure that your generosity reflects your values, not just year-end deadlines.

3. Major family moments – and ‘living inheritances’. Weddings, milestone birthdays, or helping a child buy a first home often arrive sooner than expected. Planning for these events isn’t about predicting exact dates. It’s about ensuring liquidity and emotional ease when the moment arrives.

When assets are properly aligned, you can be fully present in the experience rather than worrying about which account to tap or what tax consequences may follow.

Aligning Your Assets with Your Aspirations

Once the vision is articulated, the financial strategy becomes more precise and more focused.

We typically look through three lenses:

• Time segmentation. Assets intended for near-term experiences are managed differently from those earmarked for long-term legacy. This reduces sequence-of-returns risk and builds confidence in spending.
• Risk in context. If you’ve effectively ‘won the game,’ the goal may no longer be maximizing returns but protecting optionality – the ability to make choices without financial pressure. Risk should support your life plan, not limit it.
• Contingency planning. Especially for widows or solo decision-makers, planning must include resilience. Healthcare transitions, long-term care, and decision-support structures aren’t pessimistic – they’re empowering.

Your Next Step: A Vision Audit

Before your next conversation with your advisor, consider reflecting on these questions – either alone or together:

1. What experience have we postponed that deserves priority over the next three years?
2. If we intentionally redirected 20% of our discretionary spending, where would it have the most impact?
3. Years from now, what do we hope our family understands about how – and why – we used our resources?

In Summary

In-home care can easily top $150,000 per year, as it did for Donna's parents. Social Security and pensions typically cover only a small fraction. Adult children should assess available savings, CDs, annuities, and investment accounts to plan for long-term needs.

Coordinate with a tax advisor to leverage high medical expenses as deductions. If large care costs exist, they may offset the taxes from liquidating investment assets, thus reducing the net financial burden.

Wealth is not the destination. It’s the fuel. Thoughtful planning keeps you firmly in the driver’s seat, moving toward a future that feels deliberate, supported, and uniquely your own.

At WH Cornerstone, we take great joy in helping clients identify what would really make life fulfilling. Not what others think they should do; what they genuinely want to do. Next, we estimate the cost of such a life and work with them to make it affordable.

If you’re ready to gain clarity on what that vision looks like, let us help you think it through. Start a Future Advantage conversation today by scheduling a call with us. We're here to help.In short, by being prepared before a crisis, the more challenging aspects of caring for aging parents can be lessened, making it possible to stay in the moment and make the most of the time shared.