(Note to long-time readers: the first part will be familiar—feel free to skim.)
I’ve spent the last forty years in what I sometimes call “the 40-year war against myself and against the world, trying to make a buck and get a little love, mostly unsuccessfully.” It’s been a jagged, unpredictable path, but it has brought me here—to 65, on the cusp of starting yet another career, this time in AI.
Where I’m Coming From
I’m a leading figure in the Authentic Relating (AR) movement, having written the most popular book on the practice of Circling. I met Sophie through the movement about 1 1/2 years ago, and now we are married. Sold everything and moved to Germany. We now lead a weekly circle at our house as well as online programs, and when it works, these groups are phenomenal. We have wildly complementary skills and leadership styles. It’s a tumultuous, deeply fulfilling relationship. I adore her—most of the time. She adores me too. I’m a very lucky man.
This relationship is the end-point of the forty-year journey with several decisive inflection points. The last came in 2016 (10 years ago), when I discovered Circling at the Boulder Integral Center. That discovery led to writing the Circling Guide, which opened doors for me around the world. Later came my failed but highly developmental attempt to start an AR-sourced intentional community in Mexico, and then meeting Sophie a year ago. “Time flies when you’re having fun,” they say.
I’m not sure how much fun I’m having lately—it’s a lot of drama—but it’s certainly alive.
Money, Family, and Triggers
My life has two primary arcs. Before age 37: wealthy but miserable. After 37: mostly broke but, often, happy. I became a writer, started communities, and met the love of my life. But none of it has been smooth.
Over time I developed a theory I call karma acceleration: as you differentiate and develop, you inevitably leave some people behind. It’s hard enough in normal circumstances; harder still for someone like me, who’s intensely triggered when ignored, condescended to, or simply unseen.
I can rationally understand that I dance to my own drum, that people’s lives diverge, that “no prophet is recognized in his hometown.” But emotionally it hurts that for all my 10-year effort, my monthly royalties barely cover my car insurance. Under all of my hurt sits the cultural equation I’ve internalized: existential worth = income.
Financial Envy and Hard Realities
Fast forward to last summer. Thank God for my small pension, or I’d be on the street. My wife isn’t happy about this, and who can blame her? Three years ago, I lost all my savings and credit in a crypto scam. I’m generally capable with finances but have atrocious investment judgment. If I’d put $1000 into Microsoft in 1990 and held it, I’d be retiring comfortably. Same with Bitcoin. It’s not a noble emotion, but financial envy is real.
The AI Awakening
And then came AI. I realized—or imagined—that in this pivotal moment in human history, anyone with a brain can make money in AI if they’re tech-savvy and entrepreneurial. Pre-retirement, I ran a marketing agency that had some impact, and created successful online courses. I’m late to the game, sure, but I’m healthy, smart, and married to a brilliant and beautiful woman. Maybe all prior disasters happened for a reason. Maybe God’s plan is better, than any plan I could have invented for myself.
But one nagging question remains: am I getting more neurotic with age, or was I always this way and just didn’t notice?
Me, AI Entrepreneur??? Who am I kidding?
So I dove in. Over the last five months, I’ve started the equivalent of a Master’s in AI, geared toward entrepreneurship. I can’t tell you how many business ideas I explored with the help of AI. I founded an AI Agency and began offering “AI-savvy virtual assistant services” for $25/hour. After five months? Zero clients.
Maybe it’s because I spent more time at AR and entrepreneur conferences pursuing my hobbies, than studying or reaching out to potential clients. Maybe it’s because starting a business is tough, and there is always a learning curve.
Or maybe I’ve simply gone off the rails. Nikola Tesla at least ran a major company before going broke. I’ve only had ideas.
Still, a few real opportunities have emerged recently. My writing has taken off, both in quality and in speed, with the help of AI (I have another article about that in production by the way, of how the Human / AI collaboration creates much better writing than either of us working alone). Given my background as a writer, with three self-published books and extensive blogging (mostly for fun up until now), why not simply be paid for my writing? I had a lot of fun at a We-Flow event recently, and even more fun writing about it.
Is it possible that my livelihood also be my passion? If not, I am in trouble. Because at my age, I am not looking for job, exactly. I am looking for a life-legacy project.
But how long will that take? Balancing vision and overall well-being with immediate financial needs is tricky. My men’s group, which I started six years ago and has been profound from day one, recently gave me some hard but useful feedback: I’m not fully in reality. Borrowing money to fund my lifestyle isn’t “adult.” They’re right. Some of what I’m pursuing is perhaps fantasy. The problem of course, is that I won’t know until I’ve tried.
Intellectual Aristocracy
“Nothing is more powerful than an idea whose time has come.” — Victor Hugo
This brings me to what I call “intellectual aristocracy.” These are the people who lead culture not through wealth—whether earned, inherited, or lucky—but through ideas. You can be both wealthy and part of the intellectual aristocracy (Jean-Paul Sartre, for example). He was a financially successful philosopher (which is quite a coup), and his lifelong love affair with Simone de Beauvoir was legendary. As a lover of women, I can relate—and, yes, envy him a bit.
My AR peers dislike the term “intellectual aristocracy.” They find it elitist. They’re probably right. But I’m keeping it. For me, it’s not about making cultural waves through sheer talent or power. Plenty of brilliant artists, businessmen and politicians are complete assholes. Intellectual aristocracy is about a quality of life: where love, connection, joy, and impact dominate consciousness. Where you “don’t sweat the small stuff”. Where you realize that hurt, disappointment and failure are part of every life. Where you don’t waste any emotional energy in envy towards others who are more
”successful” than you.
The question is: how much neurosis (or developmental trauma) can an intellectual aristocrat sustain before they regress to the lowest common denominator of humankind, clinging to adaptive strategies, striving only to maintain survival, stability and self-importance in lives of quiet desperation?
Closing
I don’t have neat answers. Career reinvention at 65 is volatile, raw, and risky.
This is the experiment. And if you’re reading this, perhaps you’re running your own version too.
An invitation to explore Authentic Relating
If you are interested in exploring Authentic Relating and the challenges of being human in a small, intimate container, check out Sophie’s and mine Authentic Relating in Community. The next cohort starts October 28