Design Thinking: Retirement

by | Mar 12, 2019

There is a truth about retirement that I want you to understand: You don’t have to know precisely what you want to plan for the day when you stop working.

Sure, it helps financial planners if you can say that you want to retire in the summer of 2021, stay in your home until you downsize at age 75, spend exactly $4,221 per month on regular expenses, stop replacing your car at age 80, and take a $13,000 trip once every two years…but does it help you?

Regular readers know that we’re spending 2019 writing about the concept of design thinking and how it can be an effective tool for building a life that suits your unique self. So far in the series Kathryn, our Director of Cash Flow Strategies, has written about – you guessed it – applying design thinking to your cash flow. Today, we’re going to use it to build a vision of retirement that’s all about you, not the money you’ll spend or the income you’ll need. Just who you are and what you need to be happy and fulfilled in the next stage of your life.

Step 1: Empathize

Teresa Amabile is doing fascinating research at Harvard on how people transition into retirement, and her preliminary findings boil down to this: it is hard to retire if you don’t know who you are without work. She says:

“When you work, you are a kind of tenant in a really settled life structure, where you know where you’re going to be and what you’re going to be doing Monday through Friday. And you have a clear identity related to your work. You go from that to having to be an architect of a new life structure and, often, a new identity where you need to build a new life and explore new activities, relationships, and ways of thinking about yourself.”

Whole philosophies have been built around answering the question “Who are you, like, really?” and the job of truly knowing yourself is bigger than any little blog post can begin to describe, but here are a few gateway questions to get you started:

  • Can you answer the dreaded small talk question “and what do you do?” without talking about your job? Can you imagine a future self that can?
  • How do you feel about that future self? Are you elated at the prospect of no alarm clocks (if you have one now, that is)? Anxious about your purpose? Or does “meh” best describe your reaction?
  • If you’re in a long-term relationship, can your partner answer these questions? Would you win the Newlywed Game if you had to guess each other’s answers? Do your answers complement each other?

If you find this step hard, you are absolutely not alone. Understanding the things that make you, well…YOU is one of the many good reasons professional therapists exist, and finding someone safe to work this stuff out with is almost always worth the effort.

Step 2: Define

Although her research isn’t finished, Amabile’s preliminary findings are that the transition into retirement is easiest for people who use what she refers to as “identity bridges,” that is, strategies to maintain continuity between your pre- and post-retirement selves.

These strategies often include spending more time doing something you never felt you had enough time for when you were working, revisiting a long-dormant hobby, and repurposing career skills in a new way. Spend time now to define the activities you enjoy, skills you have, and values you want to live out. Ask yourself what you would do with your days if you had unlimited time. Can you see a bridge between those things that connects today to your future?

Step 3: Ideate

One of my favourite parts of the book Designing Your Life is what the authors call the Odyssey Planning Worksheet, where you draw out many versions of the next five years of your life, and I think we can bend it to retirement design by imagining that you’re drawing pictures of 30 years of retirement in five-year sections.

Whether you draw it, talk about it, or write it down, the goal with this step is to imagine many different ways you could live a fulfilling retirement, drawn from the bridging strategies you just defined. Version one is what we might call the default version, or the one that comes to your mind easily. Version two might be what you would do if money were no object, version three could be what you would do if money were very tight, and version four could be what you would do if no one else’s opinions mattered at all.

Step 4: Prototype

The transition research above says that it takes most people six months to two years (or more) to get comfortable with the new reality of retirement. In my ideal world, I’d give everyone three mini-retirements throughout their career as both preparation for the real thing and as something nice, because why not?

You probably can’t take six months off, let alone two years, so we’re going to have to get creative with our prototyping. Even if your mini-retirement is over a two-week holiday, a long weekend or in a few evening hours every once in a while, the key thing here is to try the things you think you want, and pay attention to whether you actually enjoy them. This activity will pay off for you well before retirement if you do it right.

The Designing Your Life team has a tool to help you pay attention, something they call the Good Time Journal Activity Log. Have an idea that you’re going to spend your time volunteering with a cause you’re passionate about? Find a way to test-drive it and pay attention. Going to babysit your grandchildren more? Garden? Write a book? Train for a marathon? Test-drive. Pay attention.

Step 5: Test!

Testing sounds suspiciously like Prototyping, but it’s not, we promise. Think of it as the “rinse and repeat” or “go back to the drawing board” step.

After all that work defining, ideating, and prototyping, the goal is to find a vision for the future that you are eagerly moving towards…and that means that you should expect to find things you want to move away from (eagerly or otherwise). If you discover, through prototyping, that lying in a hammock for two weeks straight (let alone 30 years) is definitely not for you, that’s good news.

Every one of our discovery meetings at Spring include some version of the question “what do you want?” and so many people answer – sheepishly – that they don’t really know for sure. We’ve spent many, many hours empathizing, defining, and ideating with them, and would be happy to do the same with you.

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