How to Plan Your Estate When You Have No Assets

Hi Jane—what a purposeful and rewarding challenge you’ve set for yourself: planning to use your savings during your lifetime so that you leave little or nothing behind. It’s a compelling aim for anyone who has saved enough to meet their needs, and it forces clarity about what really matters. Many people think about leaving a legacy but never prioritize the lived experiences that make retirement worthwhile.

Your sentence “it is actually quite hard to do” is spot on. Timing spending to end with a near-zero estate is difficult for several reasons. People delay retirement because they’re unsure they can afford it. After they retire they often hold back, anxious about depleting capital. Later in life they may realize they could have spent more when they had the health and energy to enjoy it. When the end arrives, any leftover estate can create tax and administrative burdens for beneficiaries. So the challenge is both financial and behavioural.

What I like about your goal is that it requires you to identify needs and wants, then design a life that matches them. It also makes you intentional with money instead of passive. That intention is central to finding a balance between living well now and leaving something behind.

Money vs. time

Most financial planning is driven by the fear of running out of money: save more, earn more, reduce taxes, and preserve capital to pass on. What if we flipped the frame and planned against the risk of running out of life and health before using what we’ve accumulated? That shift changes priorities and creates different decisions.

There are many planning tools and software programs that can model spending scenarios, including projections that aim to decumulate assets by a target date. You can also use AI or automated planners—feed them your balances, expected income, and planned expenses and run multiple scenarios. Repeating the exercise over several iterations builds confidence in the numbers and helps you choose realistic spending paths.

But modeling alone doesn’t solve the deeper question: how do you actually spend more in ways that matter? For that, I recommend looking beyond transactions and toward experiences and intentional gifting.

Bill Perkins, in his book Die with Zero, argues that you should spend on experiences and give when it will be most meaningful. Experiences generate what he calls “memory dividends”: lasting emotional returns that compound over time. Unlike material purchases, experiences can be recalled and shared repeatedly, producing satisfaction long after the event. In later years, when mobility or health may limit new activities, those stored memories can provide immense joy.

Perkins also emphasizes that dying with zero isn’t the same as neglecting heirs or charities. If you intend to support family or causes, consider doing so when it will have the greatest impact—while you can see and enjoy the difference. Gifting during life can be financial or experiential: attending an event together, funding education or a business starter, or simply giving money when it’s needed most.

If you’re worried about gifting or spending too much, you can manage risk with insurance and guarantees. There are products that protect lifetime income, cover long-term care costs, or ensure a minimum legacy for designated beneficiaries. Knowing basic financial risks are covered can make it easier to spend on meaningful experiences and support loved ones without constant anxiety.

It’s about the journey, not the destination

Striving to die with nothing is a useful mindset, but hitting that exact target to the penny is unrealistic because of many unpredictable factors: market returns, health changes, and life events. Instead, use the goal as a guide to live deliberately.

Start by clarifying what makes you feel fulfilled. What experiences matter most? Which wants, if fulfilled, would leave you feeling you’ve lived well? Once you have a list, create a spending plan for the coming year: what will you do, and what will it cost? Enter those numbers into planning software and see the projection. Repeat the exercise annually. If next year’s spending pattern is similar, what does the long-term outlook show? Can you step up spending in certain years while preserving essential protections?

Remember that spending capacity often increases when needs decline. As you age, certain expenses fall, freeing money for travel, hobbies, or giving. Prioritize the experiences you can actually enjoy today rather than deferring everything for an uncertain future.

Practical steps to move from planning to action:

• Model multiple scenarios—conservative, moderate, and aggressive decumulation—and update them annually.
• Identify key experiences you value and budget for them first.
• Consider phased gifting to family or charities when it will have the most impact.
• Use insurance or guaranteed income products to cover essential risks so discretionary spending feels safer.
• Revisit your plan after major life events or health changes and adjust accordingly.

Jane, keep thinking the way you are. That intentional mindset will help you build a retirement full of meaningful experiences. Make this year a great one—spend on what matters—and then repeat the process each year. Your life will be richer for it, and you’ll accumulate a bank of memory dividends that last long after any single purchase. I’m genuinely excited for you and would love to see the photos of your adventures.

Read more Ask a Planner columns:

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• Preparing taxes for someone who died