July 31, 2026

You Can’t Get to Where you Want to Go Without a Plan, Especially Not Retirement

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You want a Roadmap for Where?

Over the last several months, I’ve been sharing some of what makes life design important, but it occurred to me that perhaps you’re not entirely sure what is driving me. If I’m listening carefully, it almost feels as if I can hear you asking what gives with all this talk about planning, where is all of this coming from?

In very plain terms I’ve had nonstop examples of people who reached retirement, or moved closer to the end of their lives, only to discover how disappointed and sad they were. Clients. Family members. Friends. Friends of friends. Media attention spotlighting individual stories. The vendor at the farmer’s market I shop at each week. The list goes on. The outcomes were not what people had wished or hoped for. Left in place of their vision of rainbows and sparkles (or whatever that looks like for you) was anger, regret, sadness, and often a sense of unfinished dreams.

My Goal Today

By the end of this post, I hope you have a better sense of how you might avoid some of the pitfalls others have fallen into by making some fairly easy-to-initiate changes.

Daniel Pink, author of seven New York Times bestselling works of nonfiction, talks about how he takes big questions and arrives at bold answers. Recently, one of his bold answers caught my attention: “Just show up.” Mr. Pink was speaking about how we can “unlock our potential” through four basic actions. Included in the list were being consistent rather than seeking intensity, taking action despite how we feel, being disciplined, and being authentically present. Boiled down, it came out as: “Just show up.”

Daniel Pink LinkedIn post

Mr. Pink was speaking from a very specific point of view, but I’d like to expand the idea to include what it looks like to strategize for the years ahead. To jump to the ending, it all boils down to the “showing up” part. Show up to really dream about what you want. Show up to formulate how you’ll get there and what those steps require. Show up to feel the feelings, whether you get lit up from the inside with excitement or overwhelmed with fear. Being fully present, wherever you are, isn’t as easy as it sounds.

A Metaphor to Get You Started

You could think about this the same way you consider your housing arrangements. As a child, you lived where the adults in your life said you would. As a young adult, you lived where your budget allowed, even if it meant living with mice or above a loud restaurant. Moving into later adulthood asks you to take more control of your living space — deciding what works for you versus what you’ve outgrown.

Next, take that metaphor and expand it to your life. Think of it as crafting your future now so others don’t do it for you later. I mean seriously, do you really want others to take over now after all the work you’ve put into your life so far?

Some Numbers

Did you know the number of centenarians — individuals who will live to be over 100 — is expected to quadruple by 2054? According to the Pew Research Center, that would mean roughly 422,000 people compared to today’s 101,000.

Pew Research Center article on centenarians

What does this all mean for you? It translates into a whole lot of marketing coming your way for communities to live in, services others believe you need, and suggestions for how you might spend your time — and your financial resources.

A Starting Point

Now that we’ve figured out what makes this so important, let’s get started. 

Begin by really thinking about where you are now and how your current living arrangement can — or cannot — support you in the years to come. Can you walk to what you might need, or are there delivery services you can access and afford? Are the basement stairs you use to get to the washing machine really a good long-term plan? The list goes on, but as you can see, these practical considerations add up.

Do you have a Big Huge Audacious Goal (BHAG) which would benefit from attention now rather than later? Going on a safari at 80 is very different from going on one at 60, even if you’re a fit and active 80-year-old. Write the book, build the boat, take the trip, get the tattoo — while there’s still time to enjoy it.

Have you learned about your finances and how to manage them? Do you know how much you need each month or year to live on? If you don’t, now is a great time to begin educating yourself. And in case you don’t know it, there are many free and excellent resources available to help you get started.

Do you have social connections outside your family? Family is wonderful, but it’s not fair to anyone — including yourself — to expect them to meet all your social needs. This applies even to people who consider themselves introverts.

This is only a partial list, although it should get you started. Want to learn more? The MIT AgeLab has a great quiz to help you assess multiple areas of longevity preparedness. You can find it here:

John Hancock Longevity Preparedness Index quiz

It’s free. I’ve taken it myself, and if you’re worried about getting flooded with marketing material, I can tell you I haven’t been — so in my opinion, it’s worth the time.

I’ll be talking more about all of these pieces in the months ahead; if you have questions, please don’t hesitate to ask.

Round It Out

Getting focused on what you want for the life you envision in the future means taking the time to develop ideas, talk them through, and eventually create a real plan for getting where you want to go. From a distance, it can feel overwhelming, but if you “just show up,” it really does become easier.

P.S. If you have questions or want help finding resources, please send me an email. I’d be happy to help you get started.

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