Chapter 1: A New Perspective on Retirement

Lately, I've found myself contemplating the concept of retirement. Although I'm not officially retired—at least I don't perceive myself that way—my recent departure from The Recount has left me pondering how to respond to the ubiquitous question: "So what do you do?" This question often serves as a social anchor at gatherings:

Person I Just Met: So, what do you do besides attending dinner parties?

Me: I'm still trying to formulate an appropriate response.

Person I Just Met: So, does that mean you're retired?

Well, not exactly. Why does everyone immediately associate me with that term? I've always found "retirement" to be an unsettling word. It carries connotations of decay and the later stages of life. The notion of "retiring" suggests a desire to withdraw from the world, and its root implies weariness. Who wants to be weary, let alone "re"-weary?

I recognize that millions proudly embrace retirement as a badge of honor. That’s perfectly fine, but it’s not a path I intend to take. To me, it implies a cessation of contributing positively to society through one’s career. It feels like one is entering the twilight of life, with the only significant milestone ahead being an eternal rest.

Perhaps it’s time to reconsider the word's conventional definition: "to leave one's job and cease to work, usually upon reaching the standard retirement age." This definition feels so rooted in an industrial mindset.

While I am technically stepping away from a significant chapter of my life—one that has defined me for over three decades as a founding executive in various startups—I have always engaged in multiple projects alongside my primary career. Initiatives like conferences such as Signal and Web 2.0, board roles across various sectors, writing, investing, speaking, and consulting are now flourishing in this new phase, as my involvement with The Recount winds down. I’m even contemplating new ventures, but I’ve set a new guideline: they cannot be venture-backed companies with me as the founding CEO. That chapter is behind me.

However, I still grapple with the original question: What do I tell people about how I'm spending my time now? With my previous role—something universally recognized as "having a job"—now finished, I need to find a more suitable answer. Any founder will attest that managing substantial investments and a dedicated team is exhausting. After navigating seven different startups and then abruptly stepping back earlier this year, I can confidently say I’ve never felt less fatigued. In fact, I'm rejuvenated and gaining more energy with each passing week. Is there a term for that? If you have one, please share! For now, I think I'll just go with "unretired" and see how that resonates…

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Chapter 2: The Journey Ahead

Section 2.1: Redefining Work

In this new chapter, I’m focused on redefining what work means to me. Moving away from traditional roles opens up a landscape of possibilities that go beyond just earning a paycheck.

Subsection 2.1.1: Exploring New Projects