The Agony and the Ecstasy of Vocational Promiscuity

My Career Keeps Evolving. It’s Great. It Sucks.

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I’ve had more vocations than decades on Earth. They all end with a telltale sign:

It’s 1997 and I’m 27. I’m interviewing a Broadway actor for an article. It was once such a thrill. But now, as I look into his dreamy eyes, my toes are limp. The boredom starts in my feet and radiates up my meridians to my temples. Shit, shit, shit. Working for a tired theater mag is how I pay my rent. But getting up in the mornings has become a full-time struggle. I feel a wave of dread and hear a clicking sound, like a combination lock turning: click-click-click.

Or…

It’s 1994 and I’m 24. There’s a red-robed swami pacing at the head of a conference room overlooking an ashram courtyard. He’s trying to convince us that the deadly “rumors” of abuse and molestation about the gurus of our spiritual path are just gripes that were leaked to The New Yorker. I’ve dedicated years to this path, becoming a certified meditation teacher, and for a spell, even wanting to dress like him. But I sense the allegations are true. The wave of dread crests. The lock turns.

Or…

Now it’s 2012 and I’m 42. I’m sitting in a therapy session with my listening face on — soft, curious eyes — willing myself to listen harder. I’ve seen this client’s hair color change for as many years as I’ve known her — seven shades. It’s currently a washed-out pink. The joy in knowing her so intimately is betrayed by my foot, bobbing up and down at the end of my crossed legs. Foot, please stop. Click, click, wooooshhhhhhhhh. Oh, dear. No.

All my careers end with this wave of dread that literally has a sound, and a very inconvenient knowing: I’m done with this. And then, I gravitate, often clumsily, anxiously, towards a new way of earning a living that builds on what I’ve learned in the past careers and utilizes it in a new way.

Left to right: Blair in her monk phase at the Siddha Yoga ashram; Covering the Tony's with Playbill Online; Executive Coaching.

I am a professional career reinventor, or, in my own parlance, a vocationalist; also referred to as a multipotentialite, Renaissance man (person?), and jack of all trades. In my 56 years I’ve made anywhere from mere dollars to a decent amount of dough as: an actress + singer + waitress; aspiring monk; online data manager + theater journalist; acting teacher; drama therapist + workshop leader + psychotherapist; and more recently, executive / career coach + organizational consultant.

If it sounds interesting, well, it does make for a rich and varied life. But also, it’s a total pain in the ass.

Lately I’ve been thinking about the late, great Jane Goodall, may she rest in peace. Jane landed in Tanzania at age 26 in 1960 and found her calling: primate ethology. When you think of Jane, you might think: elegant, wise, committed. But you always think: chimps.

I am a professional career reinventor, or, in my own parlance, a vocationalist; also referred to as a multipotentialite, Renaissance man (person?), and jack of all trades…If it sounds interesting, well, it does make for a rich and varied life. But also, it’s a total pain in the ass.

Now, in many ways I’ve loved the variety and challenges of my lily-pad career, the way it keeps me and my self-expression personally evolving. But I admit to feeling a little envious of Jane. Her one-pointed path led her to a level of mastery, which led to name recognition, which enabled her to make a living and a greater impact, something which has always been important to me. Consistency breeds more opportunity. Though I’ve basically worked in human development for thirty years, few people know what I do, rendering me less hireable. I was recently introduced to someone at a party who, recognizing me from social media, said, “Oh yeah, the therapist, but you’re like not really a therapist anymore?” Yep. Another person, a friend, recently referred to me as a motivational speaker, which I never was, though I did once give a TEDx talk that yielded the worst quality video on record.

My professional promiscuity has serious financial implications, especially as I age. It’s not a great set up for filling the retirement coffers. Or covering mounting medical expenses. Although I might coach a business client to stay true to a simple, uncluttered mission and brand so as not to confuse core customers, I haven’t been able to take my own advice. And this past year, it’s really caught up with me.

On January 2nd, I opened my laptop to face the void which, in the lazy folds of a long holiday spell, I had managed to ignore: a 2026 calendar with zero executive coaching clients on it. In the 2010s, I gained traction working with women of color leaders who ran nonprofits. But as that decade came to a close, my referrals stopped and were rightly being redirected to consultants of color. My efforts to gain the same traction in other sectors have yielded little fruit. My remaining nonprofit contracts began terminating after 2025’s government cuts.

The fallout did leave me with a lot of time for writing, which has been a constant pastime throughout most of these careers, but never a career in and of itself. Until, maybe…now?

Because what did show up on my 2026 calendar was several writing coaching clients, two editing projects, an essay due for an anthology, and a variety of non-direct income-generating promotional tasks for my debut memoir about the aspiring monk phase (This Incredible Longing, Heliotrope). According to my calendar, without really knowing it or trying very hard, I’d become a freelance writer + editor + coach through underground referrals. But let it be known: even though my career as an executive coach is on life support, I haven’t yet felt the wave or heard the clicks.

Order the book…

When I can quiet my financial concerns, I’ll admit to waking up thrilled to spend my days writing, working with my new clients, and tackling the editing. I’m in the midst of a transition, but no longer swirling in the despair-inducing void of wondering what comes next. My creative synapses are fueled by excitement, and I remember:

This is how my careers begin — with a burst of enthusiasm and a touch of magic.

At 7 years old, I sat in a musty, intimate theater in Greenwich Village, where the blonde lead of The Fantastiks gazed seemingly right into my soul and sang, “I want much more!” I felt sparkles circulating from the top of my head to my toes and back again. I thought: I want to make this kind of magic for a living.

When a new path opens up, it unfolds like a yellow brick road in my mind, and I know where I’m going. But then, as happens on yellow brick roads, it takes quite a bit of twisting, turning, and time to arrive at the destination.

Glaser as an actor (waitress).

Once, in my 20s, smack in the middle of a performance of a dreadful off-off Broadway show, I felt the dread and heard the clicks. Weeks later, I had the dead-toes interview with the Broadway actor, and I knew it was time to quit acting and the tired theater mag, Playbill Online. But what was next? I sat down, lit a candle, and surrounded myself with colored markers. I folded a piece of paper in thirds. One column header was: THINGS I LOVE TO DO. Another: THINGS I’M GOOD AT. A third: LOGISTICS, which included very specific details about what I wanted my work life to look like, including: compensation; neighborhoods I’d like to work in; the decor of my workspace; flexible hours; and quick access to cheap, healthy food.

At the end of the exercise, glancing at all the columns, which included a love for all things theater and psychotherapy, I thought, I’ll be a healer who uses theater techniques to help people grow, and mistakenly believed I invented “drama therapy.” It turned out it was already a profession, and I got my Master’s Degree in it, launching the longest part of my career, eighteen years, as a licensed therapist and workshop leader who traveled the country.

A couple of years ago, while my roster of executive clients was whittling down, I panicked. How could I be in my mid-50s with so much skill and so little work? It baffled and deflated me. I tried to remind myself that executive leadership coaching can seem like a luxury in an unstable economy — a leader or company really has to be in a certain amount of pain to retain my services. It appeared I wasn’t alone: a few people who’d lost jobs reached out for career coaching, but naturally had little funds to pay for it (something I’ve always found off about that aspect of my profession). I didn’t know how I was going to assemble my talents to keep making a living or serve the greater good. I reached out to an astrologer.

“You’re in a holding pattern, but 2026 is the year things really start cooking for you,” she said, without knowing I had a book coming out. “You’ll have lots of opportunities for writing and work.” I felt vastly relieved. “And then,” she added, “things will settle down again. But something new will emerge in your 60s … you might be working in hospitals, or institutions of some kind.”

Sounds about right, I thought. Oh, the comfort and curse of finding your fate in the stars.

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