The Road to Retirement

Leslie Tremaine

Where to start? I started thinking about retiring years ago– reading books on how people made the transition, talking to people who were already over that threshold, fantasizing about what new and creative things I’d do , and of course obsessing about money and how to make all the nitty gritty logistics work out. My early plans were to leave a pretty big job I had and get into one that was much simpler, as a way to ease my way into actual retirement. I can still remember the dinner I had with a number of colleagues who told me how smart I was and talking about their own fantasies of downshifting .
And fantasy may be a key word here — I took that “simple ” job I saw as my transition then less than a year alter ended up saying yes to what actually was the biggest and most intense job of my whole career…. Why? I could tell a “nice” story about a sense of duty calling or need to serve etc etc but really it was ego — the title and and the lure of recognition were a siren song I couldn’t resist. Or maybe I just wasn’t ready and my earlier plans were overly simplistic… in any case I kept working full time ( and more! ) for another 8 years before really being ready to move into a new way of living that wasn’t dominated by a big status paid job.

In many ways that time was well spent, not only in terms of some rich work experiences ( and hopefully some good done in the world…) but also as time to let the whole concept of retirement ripen. My initial focus had been on what I wanted to get away from — the long hours, draining conflicts, middle of the night obsessing about big decisions , and of course the never-ending to do lists…… Like most of us I lived tethered to a so called smart phone that wore away any sense of getting away — the sound of an incoming email or a call became a reminder that I was locked in to being my job title 24/7 . Somewhere during this time I also went through a series of losses that both added strain but also served as the “heat ” needed to cook my decisions to make some changes happen — my husband died after a brief bout with cancer, I let go of the big mortgage house we’d bought with two incomes and a rising real estate market, and even the family dog died… how many more signals did I need that it was time to look at what really mattered to me and how I wanted to live? All this really came to a head when some big leadership changes happened at work,. The culture shifted radically, eroding the ties of camaraderie and common values that had been some source of sustenance for me. Stripped down in this way the decision made itself — one day I simply knew what to do and went straight to my boss to explain my plans to leave at the end of that fiscal year . The stories I told about wanting to focus on some other areas of my life were true even if incomplete — I ‘d come to the end of a particular path and knew it as clearly as I knew anything. What I’d do next was not clear but I had a basic trust that there was a path ahead and I’d be able to find it.

What had fed that trust probably included the years of “playing” at making such changes.I ‘d been rehearsing in some ways, getting used to the idea and trying out various scenarios. That deep sense of trust was also fed by years of mindfulness meditation practice and by the circle of friends and family who’d been there to support me especially over the years of loss I’d been through. The mindfulness and spiritual study helped me to know the realities of my own experience more clearly — where I’d worn down, how I’d gotten caught up in vicious cycles of putting out intense effort without renewal , the price I was paying for my hesitancy physically, emotionally and spiritually — as well as to know that I was more than my job title. The support from friends let me know I wouldn’t be alone and would have guides when I needed them. After my husband’s death I’d let friends become a stronger part of my life, sharing in my vulnerable moments and my rough edges in ways I’d previously saved for my life partner. This was all part of building up some trust– — in my own resilience , my support systems, and a world of options bigger than the one I’d lived in for so many years.

During this transition time I dug in also to some practical problem solving — making sure the finances worked, finding a simple condo to rent that let me know I’d not be tied to home maintenance and mortgages, clearing out all the years of extra ‘stuff”, figuring out the intricacies of public sector retirement processes, winding down my work in ways that felt responsible. Once those practical issues were dealt with I could then focus more fully on the really big question — not what I was leaving but what I was going to… I actually put some of the same skills I’d used at work all those years into digging into what retirement really meant and what this new chapter could hold for me. I read lots of the books now out on all the earlier myths of a Leisure World retirement , seeing clearly that many people actually shifted into new so called “encore” careers ,or continued some part time work , paid or not, as a way not only perhaps to make money but to keep connected and feel of service. I also decided in those last few months “on the job” that it’d help to start doing more of what I saw as my own “encore” work before I actually left my paid job, so I co-taught a mindfulness course at a local hospital with my mentor, developed an adapted version to use for staff at work , and worked on completing my training to be a community dharma teacher in the Insight Meditation tradition. I also put out the word that I’d be available to do some mentoring of merging leaders in the local non profit world , and started talking to the people who expressed an interest . Yes for awhile I was busier than ever but those efforts felt like laying down a clearer path into new territory before i left the road and world I knew as ‘work” .

Perhaps even more importantly I also set about interviewing people i knew who’d already retired, asking them questions about their experiences and advice. There results were not only directly helpful in pointing out some some pitfalls I hadn’t thought about, but also simply in helping me connect to a new “identity group” — people I admired who were finding new ways to live and be creative , folks I could imagine seeing as my “peers” and compadres in this new way of describing my life . The advice focused a lot on clarifying priorities, learning to say no, not worrying about answers to the inevitable questions about what I “do” . My sense of confidence growing, I began to sketch out some rituals i felt would also be important to help me mark this shift — a whole month laid out for what I considered celebration and ceremony, with some time dedicated to recovery and re gearing.. A planned solo retreat at a cabin the mountains, a whole day scheduled at a local spa for massage, facial and soaking . Part of the transition planning also included planning parties with various groups of friends as well as more writing and reading to help me both in what I needed to let go of as well as to connect to what was the new potential in my life. Music was one of the pleasures I knew I wanted more of , so I got lots of tickets to good concerts and started reading books about the history of the blues and of the eras in jazz I loved. I also got a library card for the first time in years, and picked out a new journal. My sons helped, getting me an I Phone and a Mac Air , so i could travel and stay connected to friends and family. Learning to use the new tech tools added a sense that this old dog could still learn new tricks ….

There were stumbles of course too in that wrap up phase. I stayed “hooked” by the intensity of my job in spite of knowing I was in countdown mode, and as a result was far less able than I’d hoped to use the time in less pressured and more creative ways– no :cooling down” period but rather more like running til I collapsed at the finish line . Also I was offered and took a contract for some part time work with a state level project…. at this point that decision looks/feels like another version of the earlier inability to say no perhaps to something that sounded like a sign of success and status.

Then the big day came — lots of rounds of good byes and hugs, plus more expressions of appreciation from staff and colleagues than I’d expected. I was reminded that I was part of a larger story, a chapter in the lives of others as well. The members of my meditation center had agreed to help me have some kind of ritual to mark the occasion and that was an important element — a circle of people who passed around held lovely shawl and as it passed around each person added a blessing for my new life. The one I especially remember is the person who expressed a hope I’d be wilder — letting go of my scripted life and careful control in ways that expressed joy and creativity. That blessing comes back to me every time I wear the shawl — inviting me to stay out late for some good music, to go on a long retreat, to drop everything and go visit one of my sons, to sleep in late, to show affection more openly, to take a risk and try out something new and scary…… At one point a friend took me out to ride one of her horses — something I’d said scared me in a way that felt exciting. Another friend suggested pottery — he said “hey when did we ever get to play around like this in our jobs, and if it all got messed up when could we ever just ball it up and start all over again???” The solo retreat was perfect — I took recordings of Miles Davis Kind of Blue and John Coltrane A Love Supreme with me, finding moments of amazingly deep concentration as I meditated to their compelling songs.

So now it’s nearly six months after the big shift and my life has hit a rhythm that seems to make sense at least in some interim way — part time work on the state project, teaching meditation,spending time with friends, running a couple of mentoring groups, reading and hanging out in cafes like I’m doing now. I know this is still a transition time but I don’t feel in as much of a hurry to “finish” figuring anything out about defining this time. Idid plenty of defining before — for now it’s ok to let it unfold, slowly and with some basic trust in the process. Somewhere though it all I remember the words of a leadership trainer from a decade ago . What he’d told me then seemed more a voice of truth than I’d known then — that what mattered was to learn, serve and remember…I’m still learning, and it shows up as service in new ways– and there is so much to remember.

One thought on “The Road to Retirement

  1. Leslie
    I enjoyed your description. I am probably 12-18 behind this position.

    How important do you think your social groups and your family were to “filling in your time” in early retirement?

    I would be in a position of still having a same age working spouse, no children and being more of an intraverted working male – less developed in social groups pre retirement. Also my working life for the last 24 years has been in a self owned business not as an employee. Also with that I am 5 years too young to retire whilst realising the fact that at 57 external people are not likely to hire you even though you only feel 45!

    Your thoughts appreciated

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