Transitions and How to Have a Graceful Encore


I am incredibly privileged to work with people I admire – both for their professional accomplishments and for their personal character. Working with them during transition can be particularly rewarding. I was fortunate to recently interview one of my clients; Evelyn, a 73-year-old divorcee who is going through a new transition in her retirement years.

I have known Evelyn for seven years now and have always admired the intentional way in which she approaches life. I've written about this in the past and understand that there are stages that all people go through at those times. When I was first introduced to her, Evelyn was making the transition into retirement. She recently decided to sell her home of 40 plus years and move into a retirement community, which is what prompted this interview.

Evelyn had considered many of the options available to someone in her position, from choosing to move out of state to be closer to family or into a local retirement community, to downsizing or continuing to live in her home. Now, as she prepares to move forward, she is hopeful and excited about the transition.

Not everyone is as confident when it comes to making the choice to sell their home and start on a new adventure as Evelyn is. I wanted to understand what made Evelyn different from other people who have struggled to make this transition. It’s interesting to me because I find myself having these conversations with clients more and more. While I can advise from a financial standpoint, I am far from making this transition myself and know the experience is far from simply financial. I also wanted to share the resources and wisdom Evelyn imparted, which she has graciously encouraged me to do in these blog posts.

I want to share my conversations with Evelyn in three parts. This first post includes my observations and what I gleaned from our conversations, as well as Evelyn’s written “Wisdom for Moving.”  The second and third parts will include transcripts of our discussion, because try as I might, Evelyn’s perspective is best shared in her voice.

Here are a few of my observations:


Mindset has been a buzz word in the financial planning world. Mindset refers to the belief that one’s attitude towards a situation has the power to change the outcome. Many studies support this, especially mindset’s affects in relation to retirement. Simply having a positive mindset towards retirement increases longevity by an average 7 years!

As you read Evelyn’s words, I’m confident you’ll see the correlation between Evelyn’s mindset and the outcome to her situation.

The “New” Stage of Life

Soon after I spoke with Evelyn, I heard Marc Freedman speak. Marc is the founder and CEO of, which advocates a movement rethinking retirement. Marc is shedding light on the phase of life that exists after one quits their job (traditional “retirement”) and the later years of life.

What I think is so brilliant about Marc’s work through Encore is the notion that retirement is not an ending point, but simply another step in life. He issues a call to “accept the decades opening up between midlife and anything approximating old age for what they really are: a new stage of life, an encore phase, ripe with promise.” One of my favorite lines from his talk was “It is a great travesty that we have tried to make retirement an imitation of young people.”

As I reflected back on my conversation with Evelyn in light of Marc Freedman’s presentation, I saw this played out in her life. She has embraced the wisdom that only years can bring and has intentionally searched for what fulfillment means to her now.

The Idea of Legacy

The more Evelyn shared with me, the greater appreciation I had of what legacy means. In thinking through her options, Evelyn found herself returning to how her mother and grandmother made this transition. The legacy those women left was the grace with which they approached retirement and moving into a retirement community.

As Evelyn makes this transition, I can’t help but think of her daughter and granddaughters and what they will remember when they too make this transition later in life.

Evelyn’s “Wisdom for Moving”

Being grounded in reality is fundamental. Reality includes financial, physical, and emotional.


  • Cost of house maintenance

  • Retirement budget


  • Health

  • Nutrition

  • Exercise


  • True self

  • No comparison to others

Starting to think about where and how I wanted to live in the latter part of my life:

I started early and looked at several options. I always thought I would move to Memphis where my daughter and her family live. I thought about it as early as 20 years ago, but for many reasons it was never the right timing. Later, I considered moving to where my son and his family live. However, it was never a serious consideration for several reasons.

My daughter was helpful in going with me to look at retirement centers in the Memphis area. The cost went up considerably from the time I started looking until I was ready. But looking allowed me to decide what I really wanted. I realized that I had to stick to my budget – that I had to be responsible for taking care of myself for the rest of my life. I learned that I could sacrifice space if I had outside space and if I could look out from all areas. In fact, it is freeing to "unclutter" and to “uncollect”.

Stay Tuned

It’s never too early to consider the life you’d like to lead after retirement. Read more of Evelyn’s words of wisdom in the following posts. I think you’ll find her story offers encouragement in making these big decisions.

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