Reimagine Your Retirement

What kind of life do you imagine at 50? 60? 70? 80? 100?

Will you retire? Should you retire (ever)? When will be the right time to retire?

We are all participants in one of the most significant social movements of our time: We are creating a new phase of life.

For many it happens at retirement, but in fact a reimagined moment can come at any age. It renders obsolete the myths and conventions of the past 50 years – the old story that has defined our trajectory and constrained our choices for retirement and aging.

In place of that old route, we are paving a more dynamic and exciting path: We are living longer, and staying healthier, than any generation before. Whether by choice or by financial necessity, we are continuing to work long past traditional retirement age. And, most important, we are yearning – as we have since our youth – to find meaning and purpose in our lives.

As pioneers in this new life stage, we are seeking out new possibilities. For some of us, this means delving into favorite hobbies, interests or volunteer gigs. For others, it entails going back to school or traveling to far-off destinations. And for others still, it means starting a business or embarking on a dream career.

But for all of us, it involves looking ahead and asking ourselves, “What’s next?” Here are six guideposts you can use to help you answer that question and navigate the years ahead.

Reflect – What’s real for you?
Lasting change often begins by looking inward. This doesn’t mean you must retreat to a monastery or spend hours in the lotus position. Instead, think of reflection as a break: a mini vacation from the daily tasks that absorb so much of our time. It’s a chance to go inward and listen to your own story.

Reflection involves revisiting the narrative in your head about your life up until this time. You don’t have to automatically extend that narrative into your future; you can weave an entirely new story for yourself.

Start the process by asking how you wound up where you are today: What goals and values led you here? Looking forward, what is the most important to you? What choices are you likely to face in the years ahead? What possibilities would you most like to pursue? Are you satisfied with how you spend your days? As you ponder these questions, you can begin to say no to the things that clutter your life, and yes to those that give you purpose.

Connect – Convene a feedback panel
In the early phases of our adult lives, we often make connections and form communities around family and work. As we age, the basis for those connections tends to fade. Forty years later, for example, the parents of your children’s friends are less likely to be your friends. You may have moved to another city or simply drifted apart socially. The same is true for work friends: You may have changed jobs or left the labor force entirely.

At this stage of life, it’s all too easy to end up with a wealth of casual acquaintances and a dearth of real friends. And this occurs just when we all need authentic connections.

The cornerstone of connecting is building a sounding board, which is a small group of people who can help you think about what’s next in your life. They may see you more clearly than you see yourself. To convene your sounding board, find one committed listener who can offer you support. Ideally this will be someone willing to hear you out on the questions you’ve been asking yourself, then deepen and magnify them. Once you’ve found your listener, bounce ideas off him or her every few weeks. Then slowly add new sounding board members. Strive to recruit a catalyst, a connector, and a trusted financial planner.

Explore – Open yourself to the unknown
This step allows you to begin thinking broadly and honestly about the direction your life can take. You begin to separate what you’ve always done and who you’ve always been from what you’d like to do and who you’d like to become. At this phase of your voyage, you get to give your curiosity free rein and try new identities and behaviors on for size. The point of these exercises is simply to get a feel for exploring new ideas and activities. Once you become comfortable with small explorations, you’ll be better able to embark on larger journeys of life discovery.

Kick off your exploring with some modest accomplishments:

  • Browse a magazine that never appealed to you.
  • Change your standard route home from work.
  • Skip the Sports section and delve into Food.
  • Venture into a tavern that features line dancing.
  • Take a voice or musical instrument lesson.
  • Design any other activity to get outside your comfort zone.

Choose – Whittle down your options
Now it’s time to narrow your choices. This may feel intimidating – What if the path I pick turns out not to suit me? – but your selections at this stage in the journey are not irreversible. Multiple paths lead to the goal of reimagining: there’s no need to worry that you’re swearing all-or-nothing allegiance to a wrong one. Indeed, you can ease your way into this stage by taking deliberately small steps. Here are a few to consider:

  • Take Time Out: Carve out a regular block of time when you refuse to be interrupted, especially by technology. Visit this oasis each day to imagine future possibilities.
  • Say “Hello”: Introduce yourself to organizations engaged in the things you’re curious (and serious) about. Shadow a person doing something you think you might like.
  • Volunteer: Volunteer to spend time with a special group which can point you in intriguing directions.
  • Keep Track: Record your reactions to all these investigations in a Retirement Journal. Revisit prior entries to see if clues emerge that help you pick your best path.

Repack – What’s essential for the road ahead?

  • Unpack: Repacking entails removing the obstacles that are keeping you from reaching your goal. Think of it as jettisoning the baggage that no longer fits who you are now and repacking to accommodate the person you want to become.
  • Repack: Create the table of contents that would appear at the front of your memoir. Give each stage of your life story its own summarizing chapter title. Then group the chapters and give each section a title.
  • Repeat: Now move to the present: How would you label the chapter you’ve living through currently? What would you name the chapter coming next? This exercise can give your life story a clear plotline to follow.

Act – Make your possibilities real by taking action
Using the previous exercises as guidance, take a first step in a new direction – any direction. See what happens. Then adapt your next steps as things unfold. It really is that simple: Take action.

You can ask your sounding board to help you weigh alternatives, but ultimately, you’ll have to trust your gut. And who knows what surprises will appear? When you act, doors open. New connections click. A planned meeting leads to a chance encounter – someone knows someone who knows someone else – and suddenly an opportunity materializes that you had never anticipated.

For each of the next five days, take one chance per day. Then describe them in your journal. Stepping outside your comfort zone will feel scary at first. Or exhilarating. Or possibly both. Taking action, pausing to weigh its impact, tailoring your next step – as you find your rhythm with these phases of reimagining your retirement, you may just answer what’s next.

Richard Leider, founder of Inventure – The Purpose Company, is the author of twelve books, including two best sellers, which have sold over one million copies. Repacking Your Bags and The Power of Purpose are considered classics in the personal growth field.  Richard’s PBS Special – The Power of Purpose – was viewed by millions of people across the U.S.  His recent book is Who Do You Want to Be When You Grow Old?: The Path of Purposeful Aging. His newest book is the 4th edition of The Power of Purpose: To Grow and to Give for Life with longtime co-author David Shapiro to be released December 2024.

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