Finishing Well (Enough): Intentionally Crafting the End of My Career

By Ellen Schecter, Ph.D.

In 2017, my Work lost its joy and meaning. It felt just like falling out of love after a long, fulfilling relationship. Work had been my identity and, in many ways, my most intimate partner. Through Work, I was seen, heard, respected, liked; maybe even loved. Work was my first priority. I had nurtured that relationship, investing time, learning new skills, and enjoying the rewards. We fed each other, Work and I.

American culture reinforces this relentless focus on doing, being busy, being productive. “Idle hands are the devil’s workshop,” we’re taught, and “Success comes from pulling ourselves up by our bootstraps.”

While we may publicly decry workaholism and perfectionism, we also reward it.

My own workaholism grew from three deep roots. One was the entrenched, largely unconscious American cultural expectations I just mentioned. Another was that I came of age at the height of the Women’s Movement, which invited and exhorted me to “have (do) it all.” While I never wanted a traditional family with children, I knew I could have a career, a love life, great friends, exercise classes, and volunteer service projects… and was privileged to have both education and means to do this. The final root developed in my family, where straight As were assumed, being “average” was unacceptable, and Work – homework, chores – came before Play. When I worked hard and did well, I could earn approval and love.

My need to achieve sprouted, blossomed and grew into a way of life. I crafted a successful career in business as an organizational effectiveness consultant and executive coach. Climbing the corporate ladder meant managing people who reported to me, and (perhaps as with children) I didn’t want that responsibility. Instead, I led by influencing the influencers. I wanted to have power with others, not over them. So, I facilitated the path for others to become effective leaders and grow healthy organizations.

At age 62, I was at the top of my professional game, working for an industry trailblazer. Powerful leaders turned to me for guidance. Work was challenging and made a difference. I loved it. Yet privately, it was becoming harder and harder to stay engaged. My Work no longer energized and inspired me as it once had. Familiar with short lapses of burnout, this felt like something more. I was just… done . I questioned if I was still capable of good, impactful work. And underneath I was terrified, though I didn’t know why.

Like a lover desperate to save her relationship, I tried to spice things up. I learned new skills and tools, took on different projects and roles. Like a flirtation, each attempt worked for a time, but the glow lasted for shorter and shorter periods. Even a restorative two-month sabbatical didn’t change how I felt. A line from Lily King’s Writers & Lovers came to mind: “I could see all the things I had loved about him, I could see them, but I didn’t love them anymore.” That’s exactly how I felt about Work. Not The Job, not The Company. Work itself.

Two years later, at 64, I still felt the same. My financial advisor confirmed I could retire at 65. But I couldn’t convince myself to believe it. I needed to split up with Work but felt like I couldn’t afford to leave – like a soon-to-be-ex-lover, I hadn’t saved up enough to move out. A classic double-bind: can’t stay, can’t go. What could I do? And why did I feel so afraid? Unlike many workaholics, I wasn’t worried about being bored in retirement, because (of course) I had a long list of things I wanted to do . So what was this deep fear about?

One day, lying on the massage therapist’s table in a candlelit room with music playing softly, I breathed in the calming scent of lavender. As the therapist worked on my tight, painful hips, she murmured, “Our hips are about motion, action. Could this tightness be about wanting to move forward but not being able to do so as quickly as you’d like?” I burst into tears. My body’s wisdom was undeniable. Later, I wrote in my journal:

I feel so trapped. I’m a woman of action – I think quickly, decide quickly, and act quickly. Hell, I even walk quickly! To be so sure of the next step—stop working—and not be able to do that, is killing me. If stuck for now, how do I stay present, still do good work, without resentment and burnout? How do I stop persisting and suffering—my lifelong script—and open up to an easier state of being?

I knew I’d been pulling away from work colleagues and clients. While this could be due to approaching retirement and preparing myself to leave, I was also simply losing interest. Suddenly I realized why I’d felt afraid. I was terrified that disconnecting and disengaging reflected a state I’d long abhorred – being “Retired in Place” (RIP).

I’d seen it before. Fresh out of grad school, I met people in their mid-50s who seemed to be coasting, “Retired in Place” — no longer contributing, yet unwilling or unable to leave their golden handcuffs until their full retirement age of 65. They took up space, marking time, for years. They blocked others from promotions into more senior jobs. We “early-in-career” folks fumed about the RIPs, yet were powerless to change them.

Worst of all for me, they seemed to add nothing substantial to our company or its people. Their going-through-the-motions behavior went against my deepest-held value: do something of value to others. They weren’t.

I did not want to be a RIP.

Around the same time, I had an ugly experience on a project where I felt devalued and sidelined. Feeling irrelevant and embarrassed, my sense of competence and self-worth suffered. During this time, two close friends of mine, both high-achieving and successful women who’d given their all to their employers, had similar experiences. One retired, embittered and resentful; the other trudged on, beaten down. I did not want my separation from Work to end that way.

So: I didn’t want to be a RIP, nor to be seen as irrelevant. But what did I want? How could I divorce Work in a way that paid tribute to what Work had meant to me and maintain my self-esteem? How could Work and I part ways not only amicably, but honorably?

A phrase I’d heard earlier from a consultant began echoing in my head. We’d partnered to address the end of a top executive’s tenure with his team. During a planning meeting the consultant asked me, “How can we help him finish well?” Finishing Well … that’s what I wanted. With a silent thank you , I engaged a coach to help me figure out what Finishing Well meant for me and how to do it. It turned out to be one of the best decisions I’ve ever made.

I began by exploring this notion of Finishing Well . Throughout my career I’d struggled with being too driven, trying for perfection, while still questioning my own value. I’d worked hard on these issues, becoming more realistic in my expectations of myself.  Now, I became clear that finishing “well” was neither about finishing perfectly (whatever that was), or about proving my worth. Rather, it was about finishing “well enough.”

Here’s what I discovered “Finishing Well Enough” meant for me:

• Being all in . The opposite of distancing and disengaging, I would train my intention to stay engaged and intrigued. When I was curious and caring, I found others more interesting, and we all benefitted.
• Being authentic in service of the greater good . Speaking truth to power had always been my professional responsibility, and my clients saw it as my clear added value. Without concerns about career growth, I was even better positioned to dial this up, while still showing empathy. I re-committed to saying what needed to be said to evoke real and lasting change wherever I could.
• Making a clear impact . I thought about the legacy I wanted to leave. My career had been about humanizing the workplace by influencing leaders’ behaviors. I would double my efforts to help leaders be more real, show their vulnerability and fallibility, and to embrace and invest in their own and others’ growth.
• S etting up my successor for success . Helping him be successful would create positive impact for my clients and their organizations, and that was my bottom line: to make a positive and meaningful difference. I’d include him in client meetings, and share information, history and context for the work he’d be doing.

With my goal clearly defined and strategies/tactics clear, I chose my retirement date. Finishing Well Enough became my True North, my guiding principle. It kept me grounded and directed, providing the meaning and purpose I’d been missing. And I discovered I could design and control Finishing Well Enough more than I had initially realized.

I gave my boss four months’ notice of my chosen retirement date. Keenly aware of my struggles, she was thrilled for me, sad that I would be leaving, and grateful for the time we’d still have together. We would co-craft the corporate logistics of Finishing Well Enough so that both our needs were met. This partnership itself was vital in navigating this significant ending, and I was very fortunate to have her unconditional support.

I started experimenting with taking days off, using my built-up vacation time rather than getting paid out for it. As someone who’d carefully rationed time off, this felt radical to me. But finally, I didn’t feel guilty for taking days off, which reinforced that I was truly ready to go. Rather than fill up my vacation days with back-to-back “doing” activities, I intentionally created space for “being.” Would I become anxious, depressed, bored, or guilty when every moment wasn’t jam-packed? Surprisingly, the answer was “no.” I was curious to explore the right balance of spaciousness and structure for me.

I also experimented with flipping my long-held “Work-Before-Play” rule, putting Play like reading a novel or hiking with friends before the Work of errands, housekeeping and bill-paying. In stark contrast to taking days off, this triggered a great deal of anxiety and guilt. To re-program myself, I had to fight my old scripts and inner critic. It was not easy. I had to course-correct several times a day.

As word of my upcoming retirement spread, I talked openly about my goal of Finishing Well Enough and what it meant to me. People’s reaction surprised me: “It’s so cool that you’re so intentional and open about your exit plan! Thanks for sharing your process with me.” I hadn’t realized that part of Finishing Well Enough was advocating and modeling it.

In the last months before my retirement, executives and other senior leaders spontaneously approached me, voluntarily sharing the positive impacts, insights, and growth as leaders and humans that they experienced while we worked together. Other colleagues also reached out, offering similar gifts. I felt both gratified and humbled.

Learning from them, I identified one more aspect to Finishing Well Enough —telling others about their impact on me. I wrote each member of my team a note describing the individual gift they’d given me. I sent notes to other colleagues and clients, telling them what role they had played in this most meaningful ending chapter of my career. Their responses were overwhelmingly positive, expressing how touched they were that I would take the time in our insanely busy environment to share these personal thoughts and feelings.

As my retirement date approached, I recalled a milestone-marking event I attended in the late 1970s. It was a divorce party. The couple, having been married for many years, were splitting, sadly and amicably. Surrounded by friends and family, they “unmarried” themselves. Speaking to each other with kindness and respect, they celebrated what they’d created together in their marriage, then formally released each other from their wedding vows. Afterwards, we toasted them with champagne.

My retirement party was like that. In a pandemic-appropriate online video meeting, my team and I said our goodbyes. They gave me a virtual book with pictures of us over the years, the expected congratulations and good wishes, and a surprise: they’d each added notes about my impact on them and on the organization. I was again grateful and moved. I felt I had, indeed, Finished Well Enough .

I can’t emphasize enough how important it was to intentionally design the last year of my relationship with Work. Doing so remains one of the best memories of my career. I found ways to contribute that were both meaningful to me and made a difference to others. Because of this, I was able to leave Work with pride and gratitude. Given the years and life I’d given to my career, this felt fitting and freeing.

I turned toward the future with excitement and joy. I knew I’d still struggle with some of my old ways of being, but Finishing Well Enough had taught me that I could intentionally craft my post-career life as well. And, I’m happy to say, I’ve been doing just that. There are successes, challenges, surprises, and re-calibrations. I try to stay open and self-forgiving, and am excited to explore what will blossom in the rest of my Life.

Pictured: Ellen Schecter, Ph.D