A Vision, a Map, and A New Life: Anticipating Retirement

Paula Marie Usrey

Dear Friends,

I believe each of us has the power to live our best lives at any age. To do so, we need a clear vision of what we really want our lives to look like and a plan to make the life we want a reality.  I shared how any of us can do this in my July 2017 TEDx Talk.

I currently teach speech communication at a community college. However, in 15 seven months, I will be retiring. I am using a process I call vision mapping to transition from working full-time to an encore career as a self-employed,  speaker,  coach, writer, training material developer, and workshop facilitator. Over the next 8 months, I will be sharing my journey with you. I’d love to hear your experiences too.


Entry #32: Ready for a Regret-Free Retirement? Test Yourself with These 11 Questions

As a certified professional retirement coach, I understand that today’s Baby Boomers face a different reality than previous generations did when preparing for retirement. This list of 11 questions could help you assess your readiness for creating a regret-free retirement. While these questions do not address all that you should consider before retiring, they could provide a starting point

1. Do you have enough passive income to meet your needs plus emergency funds?

As the Social Security Administration projects that one in four Boomers over 65 will live to be at least ninety, are you prepared financially for a long retirement?  Passive income could include pensions, social security, rental property, royalties from creative works, dividends, or other streams of revenue. Of course, any of these sources could be less stable than we may want to believe.

2. If you want to make additional money or work part-time, have you considered how to make this desire a reality?

Because we’re likely to live a lot longer than previous generations, a growing number of Boomers plan to work at least part-time during retirement. The reality is 65% of Boomers report they have experienced age discrimination. Still, some Boomers are able to scale back their hours and keep working for their current employers. Others have found free-lancing or working for themselves best meets their needs.

3. Have you given yourself sufficient time to prepare for the nonfinancial aspects of retirement?

Retirement is one of the biggest transitions we’ll make in life. Part of our life will end when we leave our jobs. A new beginning awaits us. Yet if we don’t sufficiently plan, we could end up with a lot of regrets. Research suggests we give ourselves about two years to plan for the nonfinancial aspects of retirement before leaving our jobs.

4. How strongly do you feel your work role or position is a central part of your identity?

One of the biggest struggles many new retirees have is trying to figure out who they really are after they no longer have a specific work role or title. Dr. Who? Who are you becoming?

5. Are you confident that you can develop enough structure in your life so that you feel like you can make the most of potentially decades of retirement?

Having a job generally provides enough structure to give us feelings of accomplishment and helps us keep focused. When you retire, how will you structure each day, week, and month? A lack of structure is one area that can be very difficult for some new retirees.

6. Have you developed interests or hobbies that you will pursue in retirement?

Just like saving for and planning a trip around the world, it is wise to make sure you have some idea of the activities you want to pursue and the things you plan to do once you are free to do them.

7. Do you have at least the beginnings of a social network beyond work?

We may believe that we’ll still see the same ‘friends’ from work after we retire, but that’s not usually the reality for most. Loneliness is a significant issue for some retirees. Having a social network also helps keep us engaged and often healthier. If you are an extrovert, finding new friends might be easier than if you are not so outgoing. Volunteering or belonging to an organization or religious group is one way to connect with new people.

8. Are you currently doing a good job of managing your overall health?

Eating a healthy diet, getting regular exercise, managing stress, getting sufficient sleep, and getting routine check-ups are more important than ever as we age. Studies show that these behaviors may lead to longer, more satisfying lives and are also good for our brains. However, if you currently are not managing your health, don’t expect to become a fitness guru after you retire.

9. What are your plans that involve keeping mentally stimulated?

Do you enjoy reading, taking classes, interacting with people, or learning something new as a self-directed learner? Studies suggest that a lack of mental stimulation after retiring can contribute to some cognitive decline.

10. If you’re in a relationship, have you each shared what your vision of retirement looks like?

Retirement not only affects our lives, but it affects the lives of those who are closest to us (including family members). It is vital that we talk to the important people in our lives about our goals and our vision for our retirement. Have you had ‘the talk’ about retirement with those closest to you

11. Are you able to identify some of your core values, and do you know some possible ways you might act on those values in retirement to give your life new meaning?

Having a sense of purpose or meaning tends to become increasingly more important as we age. For some, this quest for meaning or a ‘life vision’ can become an all-consuming task. Identifying our purpose or that personal mission that gets us going in the morning usually starts by unearthing our core values. What values are so important that we are willing to sacrifice, to prioritize, and sometimes even take a stand for them? Examples of core values could include faith, family, service, social justice, friendship, making the world a better place for future generations, etc. Because many of us sacrifice part of who we really are when we hold down full-time jobs and careers, rediscovering what really matters to us might take some work.

Like BoomerBestU on Facebook to receive more information on creating the retirement you really want.


Entry #31: Nine More Weeks and Counting

I am leaving my community college teaching position in nine weeks. I can’t believe that I’m finally making this change.  I first started planning for my exit three years ago after a school shooting in my building. I was trapped in my office as nine people were slaughtered. After I was escorted out of the building past ambulance gurneys transporting students who survived but were injured, I knew I needed to start thinking about retiring.

Last summer when I had an opportunity to give a TEDx talk, Your Best Life at Any Age, I started focusing on what I wanted to do with the rest of my life.

I read everything I could get my hands on to prepare for retirement. I even earned a certified professional coaching designation so that I could better understand the retirement process. What I did learn is that retirement is one of the biggest changes we can make in our lives. It is very important that we are prepared – not just financially, but prepared to replace what we lose when we actually retire.

Not only do we need to make sure we have enough passive income to meet our needs (this could include a pension, social security, rental income, or other sources), but that we have developed a new identity for ourselves beyond the workplace.  In addition, we need to think about connections with others. We may think we’ll continue to see our work buddies after we retire, but that’s not very realistic. Also, we’ve got to figure out what’s going to keep us motivated each day. It may sound great to have freedom and control over our time, but that could quickly turn into boredom and hours in front of the television. When we figure out who we are becoming and what will help us find meaning in our lives, we’ve also got to develop a certain amount of structure for ourselves.

As eager as many of us might be to move on – to leave work – to get out of Dodge, it takes a lot of planning to move into a new life that is full and satisfying. As for me, I’m developing a plan to work for myself. I want to work with other Baby Boomers to help them identify the information, strategies, and tools they will need to live their best lives now and in the future.

In December, I will be launching a new website for Baby Boomers – BoomerBestU.com.  In the meantime, I have launched a Facebook page for Boomers who are interested in information about the nonfinancial aspects of retirement. As it has turned out, the site is quite interactive.  If you are interested in living your best life in retirement, please join us at: Boomer Best U!

Entry #30: 56 More Days and Counting

I will be leaving my full-time teaching position at a community college after 56 more contract days. I spent this past summer working on my business research and development. I also earned my certified professional retirement coaching designation. Last week I established a new Facebook page to introduce my new work and research.  Check it out!



Entry #29: Let’s Change the Narrative about Aging Together. We’ve Got the Power!




Entry #28: We’re Living Longer than Ever. Are you Prepared for a Long Life? 


First, the Good News

Here’s some good news from the Social Security Administration: One in four 65-year-olds are likely to live until they’re 90. And one in ten 65-year-olds will likely live to be 95. We’re living longer and healthier than any generation before us. For some of you, this means your retirement life might be longer than the years you worked.

The Potentially Bad News

Of course, there are some downsides to having potentially a lot of years ahead of us. For many, this may mean outliving retirement savings. It also means that unless you have an idea of how you want to use those years in a meaningful way, boredom is likely to set in after the initial glee you may feel after leaving work. In addition, a lack of challenge and engagement could accelerate cognitive decline.

As I mentioned before, I started reading everything I could find on retirement about three years before I planned to officially retire from teaching at a community college. I also reviewed my financial plan to make sure I really could retire.

A Couple of Options to Consider When Thinking Ahead

I learned that a growing number of Boomers are addressing some of the downsides to longevity by either working part-time on their own terms or by starting a small business – not necessarily for the money, but because they enjoy working when it is something they love.

One book I found especially helpful when thinking about different post-retirement options was Ernie Zelinski’s book, How to Retire Happy, Wild, and Free

Ernie’s book is backed with solid research and offers clear guidance on how to develop clear retirement goals.

Preparations for Launching a Small Business in Retirement

From the reading and reflecting I’d done, I knew there was much I would miss after officially retiring. I have enjoyed teaching, investing in others, and helping people grow. In one of my previous lives, I did research and conducted training around the United States. I’ve been fortunate have a career I’ve loved. However, I am old enough to longer want to serve someone else’s agenda or comply with mandates that I no longer embrace.

Even though I am tired of working for someone else, I want to stay engaged with work I love. That’s why I’ve chosen to work for myself for the foreseeable future.

I actually started thinking about the possibility of working for myself decades ago. Earlier in my life, I thought I needed a guaranteed salary and related benefits that regular employment provides.  In retrospect, I think I was too dependent on my career.

Once I realized I didn’t have to depend on my career anymore, I started brainstorming what kind of business would fit my background and what kind of needs I could meet. I wanted to do something I loved, not something I needed to do.


I started with a self-assessment. I considered my experiences, skills, general background, my strengths, and my weaknesses. I also considered my basic temperament. Because I lean toward introversion, I know I’m the type of person who can get drained pretty fast by doing a lot of F2F networking that some businesses require. However, I enjoying interacting with people and enjoy teaching and facilitating workshops.


Because I had reviewed a lot of retirement literature, I was aware that new and soon-to-be retirees needed tools and strategies to create their best lives as they started a new chapter.

I interviewed business people, got advice from the Small Business Development Center, and also completed coursework and practice coaching to become a certified professional retirement coach. Even though I am not doing one-on-one retirement coaching as part of my business, the need for nonfinancial retirement tools and strategies was clear as I met with a number of Boomers anticipating retirement.

I am now preparing to live my dream when I retire from teaching at the end of December. I get to provide nonfinancial retirement tools and strategies for Boomers, help facilitate discussions and lead occasional workshops with interesting people.

What about You? Will You Be Ready? 

What about you? Do you have a clear picture of your next best life as you think about your retirement years?  Are you familiar with current research on what you need to be doing to live your best life? Could you use some practical tools and strategies to help add more focus to your retirement years? If so, watch out the resources that will become available on BoomberBestU.com or join a conversation on our BoomerBestU Facebook Group beginning in January 2019.


Entry #27: Irritability and Other Changes in Relationships 

Before making some observations and doing a bit of research, I thought I had pretty much figured out how to glide into retirement. I have worked through the financial planning pieces, and have looked closely at what I want to put in place to have a satisfying retirement. However, I hadn’t considered how retirement can affect close relationships. If you or someone you know is heading into retirement and also is in a relationship with someone, please share this article I recently wrote for Sixty and Me about negotiating relational changes in retirement:


Entry #26: Becoming Invisible: Women, Choices, and the Power of Voice

I’m an elder woman. To some, that means I’m invisible. As women, I believe many of us become more invisible as we move into our fifties and sixties. Becoming invisible can affect our sense of self – our identity. However, I believe as women, we have choices. Sometimes it is convenient to be invisible. Other times, we must take our power back and make sure our voices are heard.

Last week I wrote an article for Sixty and Me about becoming invisible. Let me know if this resonates with any of your own experiences:


Entry #25: How to Live Your Best Life – Don’t Reinvent Yourself, Reclaim Yourself

Reinventing: A Set-Up for Failure

When I was young, one of my biggest mistakes was that I tried to reinvent myself to please other people.  I didn’t realize that by simply reclaiming my true self, I could be my best and strongest self.

I got married right out of high school to a man I had only known for three months. The man I married had a big personality. This man loved adventure and wasn’t afraid of taking risks. He also embraced some fairly traditional beliefs about women’s roles. I wasn’t all that skilled or experienced doing traditional, female work. Rather, I was a shy young girl who tended to be cautious and enjoyed quiet time to think about ideas.

A couple months after getting married, I was pregnant with our first child. I tried hard to be the kind of wife my husband wanted me to be. I also tried hard to be the kind of mother I thought I should be even though I knew very little about parenting.

As my children started to grow, I realized how inadequate I felt as a person. Because of how I felt, I started seeking ways to develop myself. I learned to speak in public. I got an education, and I landed solid professional positions. I tried very hard to be everything I thought I should be. Yet I felt like I was failing. I felt like each of my roles were contradictory in different ways.

Paying the Price

I felt like a failure as a mother when I was expected to be in the office instead of at home. I felt like a failure as a wife when I handled responsibilities in a corporate environment but couldn’t always keep on top of housework at home—the housework that my husband thought I should be managing. I felt like a failure when I could only manage to make myself stay in a position for a couple years before trying something else—always hoping something else would feel more natural for me.  Even when others told me I was doing a good job as a mother, a wife, and a professional, I figured it was only a matter of time before I’d be exposed as a fraud.

Once my children were grown and my first marriage was starting to split at the seams, I suddenly realized I had no idea who I really was. I couldn’t even recall that my favorite color was blue or that I had always loved Bach, or that I cherished quiet time. Because I didn’t know myself very well, I lived much of my life on a day-to-day basis.  And, because I didn’t really know myself very well, I couldn’t really envision my future.

Lost and Found

My marriage of over two decades ended. My children were grown and gone. I was left alone with someone I didn’t really know anymore. For several months, I worked hard to rediscover who I was. I sought some help from counselors, talked with friends, did a lot of reflective writing, and worked hard at excavating “the real” me.

One of the more difficult parts of rediscovering who I was involved putting all the pieces of my life back together in a way that made sense. There were parts of my life I had tried to forget – and even tried to pretend never happened. While those experiences didn’t define who I was, they were a part of who I was and the insights I had developed. When I was ready to really look at a portrait of my life, I could finally see the natural highlights and the necessary shadows that gave me character and depth.

After a lot of hard work, I knew myself a lot better. I knew my strengths and areas where I wanted to grow. I also knew that I was a person who loved learning. Once I reclaimed who I really was, I was actually able to visualize the future I wanted.  Given my temperament, my personality, my experiences, and my passion for learning, I could easily see myself teaching full-time at a community college. Community colleges often serve people who face the types of challenges I had faced earlier in my life.

Living My Best Life

I have taught at a community college for fourteen years. I have never thought twice about being anywhere else. Once I knew who I was, it wasn’t hard to figure out where I belonged. Because I feel like I have been where I’ve belonged all these years, I have felt confident about what I do.

Within a few months, I will be retiring from teaching full-time. After I retire, I am going to start a part-time web-based business for Baby Boomers. I’m also going to enjoy more time with my soulmate – the man I married after I figured out who I really was. Like me, he is a quiet person who doesn’t like to take risks and loves to think about ideas. He’s also a person who treats me with love and affection and takes time to really understand me.

What about you? What makes you happiest? How would you describe your true, authentic self?

 Entry #24: Listening to Our Inner Voices

Can you recall times when you were referred to as being irrational or overly emotional just because you are a woman? Can you recall times when you had a gut sense that you referred to as intuition but didn’t listen to what your body was telling you because it wasn’t logical?  I have been there many times myself. Because I got tired of being told I was not rational, I quit listening to my inner voice. Instead, I focused on developing strong reasoning skills based on empirical evidence. 

Now that I’m an elder woman, I have started realizing how valid and how powerful my inner voice really is. In a recent article I wrote for Sixty and Me, I addressed the power of our inner voice. I thought some of you might enjoy reading it.


Entry #23: A New Chapter on the Horizon

When I started my first professional career, I was enrolled in a great retirement program. I was young, and couldn’t imagine actually retiring someday. When I decided to go to graduate school, I decided the easiest way to fund it was to pull out what I’d put into my retirement. That wasn’t a very wise plan.

A Failure to Plan

I didn’t even consider other options to fund graduate school. Soon after starting, I discovered I qualified for scholarships and then learned about graduate assistantships which allowed me to cover the tuition for four years of my education. I used the money I withdrew from retirement to pay for living expenses – expenses I could have covered through other means. At the time, withdrawing my retirement was simply the fastest and easiest way to do what I wanted to do.

I kept telling myself I had plenty of time to think about retirement. I didn’t do much planning for several years. To be honest, it wasn’t until my own son, a financial planner, sat down with me when I was in my early fifties and had “the talk” with me about retirement.

Time to Catch Up

Once I started visualizing what I really wanted my life to look like after I retired from teaching, I knew I had a lot of catching up to do before I could even consider ending my career.  I not only needed to figure out what I wanted to be doing after retirement, I needed to figure out how much money I was going to need to make my dreams a reality. For me, that meant teaching a lot longer than I had once imagined. I’m now one of the oldest faculty members on campus. How did that happen?

I am teaching 8 more weeks this term, 5 weeks during the summer, and 12 weeks (including in-service) this fall. Then I”m done.

A New Plan

My dream after retirement is to start a web-based business for Baby Boomers. I’ve been working on the plan for this business over the past two years. I’m going to be ready this time.

I hope you’re all smarter than I was. For too many years, I had planned in the moment rather than for the long haul. I hope you all live long and realize your dreams. To do so, it helps to figure out what you want those dreams to look like and what you need to do for them to become a reality.

Entry #22: A Baby Boomer’s Next Chapter

Scary, exciting, unsettling? These are all common experiences when Baby Boomers start preparing for their next chapter ahead of retirement.  Some literature on transitioning into retirement suggests that we start preparing for our new lives at least two years before we leave our full-time positions.

Fortunately, I did start planning my retirement about 16 months ago. In ten months, I will retire from my fourteen-year encore career as a full-time speech communication educator at a community college.

I started preparing by reading everything I could find on transitions and retirement life. I also worked on my own vision for my ideal life after teaching. I brainstormed, journaled, cut out pictures from magazines, and listed some of my strengths, experiences, personal limitations, and temperament (my temperament leans towards introversion). After a fair amount of work, I was able to develop a vision for my next chapter.

I will be operating a web-based business for Baby Boomers who are preparing for their own next chapters. Working with a gifted colleague and friend, we will share research about Boomers, offer workshops on how each individual can develop their best next chapters, and provide activities and other opportunities to keep engaged with a vibrant community.  Eventually, we will offer our services to businesses that want to help employees transition into retirement.

I have a lot to learn about operating a business. I’m preparing by talking with people who have successfully operated businesses, and I am doing a lot of reading. I’ve also met with our local Small Business Development Center a few times.

I get a bit scared and excited when I think about the future that is starting to unfold. From all that I’ve read, I know this is normal. As the late Bill Bridges, author and consultant known for his work on transitions pointed out, the process is the same for all of us–we all go through endings, neutral periods, and new beginnings. Each transition phase has its own challenges. I’m ending something but have not yet started something new. How about you?

Do you anticipate a major transition in the near future? Or are you currently moving from one phase of your life to another? What have you learned in the process? What are your dreams for your next chapter?