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The Sheer Joy of 'This Is the Last Time I'll...'

Advice about gratifying ways to plan your future

By Bart Astor

My wife and I recently bought a new mattress — probably the last mattress we’ll ever buy, given that we’re in our 60s and not likely to outlive its life expectancy. Our 5-year-old border collie, Skye, immediately bounded up onto the mattress and it then occurred to us that Skye will likely be our last border collie since the breed will be way too much for us to handle in our late 70s and 80s.

Facing these “last in our lifetime” experiences may seem morbid. But we’ve come to realize they are a gift, a nudge for us to think more about what we want to do with the rest of our lives.

In my book, AARP Roadmap for the Rest of Your Life, I provide 10 tips for creating and completing your bucket list. But the fact is, I don’t much like bucket lists. We tend to keep things on the list that are outdated and place too much importance on completing a series of activities. Instead, I prefer a more fluid outlook about the lifestyle we want to lead, focusing on the foreseeable future, not some far-off time.

I can’t really imagine what my life will be 25+ years from now when I’m in my 90s. We’re certainly doing our due diligence with financial planning so we don’t run out of money. And it’s comforting to know that if we do get to be old, we won’t be financial burdens on society or our kids.

I can envision the more immediate future, however, perhaps five to 10 years out. That vision might change. But barring any major variation, we will be pretty much as we are now. Slower, perhaps, but not radically different in our interests and abilities.

So the nudge we got from our last border collie jumping onto our last mattress led us to a conversation. This was not one of those “heavy-duty” conversations. Actually, it was something I looked forward to. It gave us both a chance to dream and share our dreams with each other, with questions like:

Where would we be living?

What will we do with our second home?

Where do we want to spend the winters?

Those are fun questions to address. Then there are all the others: Do we want to keep working? How much? What do we want to do with our free time? (Note: If you are single, this planning still applies. You can have the conversation with a trusted friend or even with yourself.)

Money, Work and Lifestyle Choices

Step 1 in this exercise usually requires crunching numbers. Fortunately, I had already done that and so came to the realization — and to the conversation — armed with the reassurance that all the saving and investing we’d done over the years will enable us to ensure a modest, comfortable existence for the rest of our lives. It meant we could stop working and still be OK, barring any major disaster.

But we had to address the question of whether we wanted to work. And we had to address our lifestyle plans and options: more travel or less; more time in our second home; a different second home that’s more age- and climate-appropriate; do we want to stay in our current home?

My wife enjoyed her work for the most part. But her enthusiasm had begun to wane, especially when the work entailed long hours and being away from home. A good friend, Farrell, who is a few years older and retired several years ago, told my wife to think about whether she wanted to be working at her job when she was 80, 75, 70 or younger. Then she should count backwards until she found the lowest age she could still imagine herself at work. That clinched it for her, and retirement became part of our plan.


I’ve done that same exercise with our vision of dog ownership. Skye will live another 10 years, we hope. I definitely cannot imagine having a dog to care for after Skye, especially a puppy. So I’ve made the statement that we should not get a second dog while Skye is around (a dog who would eventually replace her). I counted backwards and realized Skye’s very likely our last.

We were both quickly able to agree that we were very happy living where we are. We’re near our family, our home can accommodate us if our health is failing and we love that we have good medical care, public transportation and access to what a big city offers.

I invite you to do the same thinking and talking about your future. And, perhaps, if it works for you, count backwards.

5 Suggestions for Thinking (or Talking) About the Future

1. Think of this conversation as a fun way to dream about your immediate future, not as a heavy-duty talk about relationships. That will help you look forward to it, not dread it.

2. Limit your perspective to the “foreseeable” future, not some vague distant future. Come up with a specific time frame, say five or seven years from now.

3. Imagine yourself in this new time and envision what your life will be like. Then ask questions such as, “Will you be working?” “Where might you be living?” and “What will occupy your daily life?”

4. Prepare for this conversation by crunching numbers beforehand so you know in advance how long you’ll have to work, what kind of lifestyle you’ll be able to afford and how secure you’ll feel in knowing you’ll have enough to live into your 80s or 90s.

5. Choose a time when you won’t have too many distractions. If you’re with a partner, being in a car for an extended period can be a great time, unless the stress of the drive affects you too much. If you’re by yourself, late night or early morning can be an inspired time.

Photograph of Bart Astor
Bart Astor, an expert in life transitions and elder care, is the author of the book AARP Roadmap for the Rest of Your Life: Smart Choices About Money, Health, Work, Lifestyle and Pursuing Your Dreams and Baby Boomer’s Guide to Caring for Aging Parents. His website is and he can be reached at [email protected]. Read More
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