Chapter 1: A Defining Moment

The question of whether to embrace retirement or undergo a rebranding has been weighing heavily on my mind.

This dilemma feels akin to asking, "If I were a laundry detergent, what would my brand represent?" It's a thought-provoking inquiry typical of MBA discussions, but I am long past that stage of my life. Now, I find myself contemplating whether I should refine my brand or step back to savor a more tranquil existence.

Recently, this question has been a constant presence, much like the influx of advertisements from health insurers promoting their Medicare plans. With just five months until I can enroll in Medicare, the prospect of reduced health insurance costs is appealing. For over two decades, I have invested significantly in my health coverage as a self-employed consultant.

However, the true catalyst for my reflections stems from the conversations with friends who are actively planning their retirements. Their enthusiasm is infectious, and they often encourage me to join their ranks, sharing sentiments such as:

"Jill, you’ve dedicated your life to work. Wouldn't retirement offer you a chance to truly enjoy life?"

"Consider retiring so you can travel with us. You’ve always wanted to learn bridge; now's your chance. You could write without a looming deadline."

"I see this as a sign from the universe. The pandemic shifted many perspectives, allowing us to appreciate life more deeply."

While I have responses to each of these sentiments, they ultimately lead to a realization:

1. My Passion for Work: If I were to summarize "work" in four letters, I might choose "play." I thrive on the creative process, and although it can be challenging, the satisfaction I feel afterward is rewarding.
2. Homebody at Heart: I understand why travel excites many, but for me, the comfort of waking up in my own bed, brewing coffee, walking my dog, and enjoying tennis or gym sessions is ideal. I can envision occasional trips, but I find solace in the familiar. Thankfully, my spouse shares this sentiment.
3. Evolving Perspectives Post-Covid: The pandemic has highlighted the finite nature of our days, prompting me to seek meaning in my choices. I plan to embrace new activities like bridge and mahjong, and I hope to finish the fiction series I’m currently writing. With my writing, I enjoy the freedom of no strict deadlines.
4. Financial Motivation: While not entirely tied to my self-worth, the sound of success—both figuratively and literally—remains appealing.

Recognizing these truths has led me to the conclusion that rebranding is the path forward. However, I face challenges as many of my former colleagues have retired, making it tougher to find clients needing market studies—the cornerstone of my work. Additionally, many clients aim to reduce costs, coupled with a saturated market.

To navigate this, I have decided to slightly shift my focus, aiming to stay engaged, continue earning, and avoid the frustrations of a crowded field. My goal is to rebrand myself as a writer and consultant. While I have previously written for clients, it was more of an auxiliary service; now, it will be my primary offering.

I will still be on the lookout for market studies, but finding such opportunities feels like a game of "Where's Waldo?" As I mentioned earlier, I choose to channel my energy differently now.

My rebranding journey began with revamping my website, a challenging task for someone who prefers to stay out of the spotlight. I was fortunate to receive guidance from a talented technologist and musician who understood my struggles. Whether his empathy was genuine or a clever management tactic doesn’t matter; I felt understood.

Here is my new landing page: the landing page of my website jillebstein.com

There’s still much to accomplish beyond this website. At 64, I aspire to remain an active consultant for the next decade, though I anticipate adapting to new realities along the way.

So, when friends ask, "When are you retiring?" I often respond, "When there are no longer people willing to pay me for my work."

This may seem like an exaggeration, but I believe I will cultivate a new, personalized definition of retirement that is nuanced and, hopefully, fulfilling.

Wish me luck!

Chapter 2: Insights into Retirement and Rebranding

In this insightful video titled "What are We Doing, Anyway? Big Questions (and Some Answers) for Inclusion in Tech," the speaker delves into profound queries about inclusion and purpose in the tech industry.

In "Answering All Your BIG Questions…This Gets Personal," the presenter addresses common concerns and personal anecdotes, providing a relatable take on navigating life's uncertainties.