The Bewildered Beginner

In Chapter 1 of “Eating Adverbs” I ask readers to make a list of things that they have been putting off until “Later.” Later on in the book (no pun intended) I ask them to revisit the list with the following exercise:

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The 2 a.m. Reason

Go back to your list from Chapter 1 – the things you wrote down when you were still living in Later. Look at them now. Something on that list probably makes your pulse quicken and your stomach tighten at the same time. That’s the one.

Not the safe version. The real one.

Name it. Write it down without qualifiers or hedging. Not “maybe I could try . . .” or “it would be nice to someday . . .” Just the thing itself.

Now ask yourself two questions:

What’s the one move that would make this feel irreversible? The flight booked. The email sent. The commitment made out loud to someone who’ll hold you to it.

And what’s actually stopping you; not the excuse you’d give at a dinner party, but the real reason? The one you’d only admit to yourself at 2 a.m.?

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As with many exercises in the book, I share my own answers. When I worked through it, I expected something from my own Later list to surface, but what came up was bigger and more terrifying than any of the items I had put on that earlier list:

I wish to retire from my full-time career and embrace self-employment.

There it is. The thing I’ve been circling for years, telling myself I wasn’t ready, that the timing was wrong, that I needed more saved, more planned, more certainty. But when I finally faced down the question, “What’s actually stopping me” I found that it wasn’t money or logistics. It was identity. I’ve been a performing arts director for decades. Who am I if I’m not that?

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When I wrote about that nearly six months ago, I had no idea I was creating a prediction.

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In January I was attending a conference in New York. One afternoon, I took a break to go back to my hotel room and check my work email. I imagine anyone reading this has probably had at least one experience of getting that “one email too many.” Mine came that day. I read the email and found myself surprisingly calm. It was this feeling of dissociation - like I was outside of myself looking at myself. It’s a weird sensation, but one that I recognize because it always seems to come when I am dealing with an unexpected crisis or when I am in a place of serious transition.

A huge bonus of the timing was that I had just returned a week earlier from a 12-day Vipassana meditation training and I was still carrying a sense of calm equanimity that comes from that particular meditation technique. Also, having posted daily “Five Things I am Grateful for Today” posts for over 14 years and accumulating over 5000 days of gratitude posts - that have taught me to find something positive in everything, even when it’s extremely challenging.

I managed to shoot off a clear and unemotional email to my supervisor and said we would meet when I returned from the conference to discuss the serious issues raised in the email. On the flight home, I had time to think about the situation. Anyone who knows me well knows that I have been dealing with years of dissatisfaction around my job, but I was making the best of the situation and slowly chipping away at the issues. This infamous “one email too many,” however, was the final straw.

The problem was that I couldn’t afford to quit. I have no savings, and a ton of debt left over from some unfortunate life experiences a while back, so I felt like I was in that old proverbial “golden handcuffs” situation. Even though I couldn’t afford to quit, I thought to myself, “What would happen if I retired?” Honestly, I didn’t have much hope there as I only have 19 years in the retirement system of my job, but on a whim I went to the website and started playing around with the math.

To my surprise, I realized that I could retire any time after April 30 with about half of the salary that I need to survive (including great health insurance). I also realized, playing with timing and numbers, that nothing would change between May 1 and October 1 as far as amount of annuity. I sat with that realization for a while and thought, “If it’s bad now, five months is probably only going to make it worse.”

So I did what I have done so many times in my life - I jumped. I filed the paperwork and in late February gave notice that I was retiring as of May 1. By great luck (or some grand Universal design) I found a consulting job in the performing arts that allows me to work remotely starting in June (part time) that adds some to my monthly pay. The rest - I am clueless about what I am going to do but I am just going to trust.

The decision happened so fast that I really haven’t had time to process it. Add to that the concept that I have been in the midst of finishing up my book with a launch of late May and it’s a recipe for overwhelm. And I feel it. I feel entirely overwhelmed.

What’s also incredibly bizarre to me is the fact that in the book I write about eight different “portraits” of the types of people who can and should embrace the solo independence I’m writing about. One of them I call the “Bewildered Beginner.” That one was based on my mother’s journey as a widow. The Bewildered Beginner, at least in my original conception, is someone who has been part of a couple for a long time and suddenly finds themselves alone and has to either re-learn or learn for the first time how to be alone and how to navigate the world solo.

I thought I was describing other people’s patterns here, but it turns out I was unknowingly writing my own next chapter. That ‘archetype’ of someone starting over from zero is here and this time I’m not writing from a safe, analytical distance, I’m inside it and I can’t hide behind my manuscript any more.

My original plan for this Substack was to use it as a way to elevate my 5000+ gratitude posts in some way and to connect them with my upcoming book launch. That was the strategy. Then something shifted. A few days ago, as I was thinking about my last day of work, I had this massive “light bulb” moment.

Here I am, the person who wrote an entire book about solo independence, and I’m about to face the hardest test of that idea - one that I didn’t write about because I didn’t know I was going to have to live it.

When I mentioned that last bit to a friend, they asked me how I was feeling - about all of that and about retirement. I don’t think I have ever felt more conflicted about anything in my life before.

I feel relieved that I won’t have to worry about the commute, the HR dramas, the hierarchical politics, the unending crises.

I feel sad because I am leaving a career that has been so much a part of my life for 25 years that I realize it’s become “who I am.” Intellectually, I know I am not losing myself but somewhere in there I feel like a major part of myself is going to be cut away and I feel completely untethered from the idea of how I fit in the world.

I feel excited because I have always craved excitement and the thrill of the unknown.

I feel worried - about money, about the success of my book, about so many things.

At the same time, I feel hopeful about money, the success of the book, and so many things.

I feel frightened about how people will respond to the book. Will they hate it? Will they say awful things online? I feel so incredibly raw and vulnerable putting out this memoir.

I feel scared of the silence. What will it be like when I don’t have the daily interaction with other people? Will I feel more lonely? More isolated?

I never thought I would understand how to be both “terrified” and “relieved” at the same time, but I’m living it now.

Finally, I keep asking myself all the unanswerable questions.

Am I being foolish? Am I making a mistake? Is this just me running away from conflict and calling it courage? Am I justifying a desire to walk away rather than dealing with challenging situations?

I don’t have any answers - not yet.

There’s this delightful myth that retirement will be all about relaxation. Just waking and having endless days of sunshine and rainbows and unicorns stretching out in front of you. No more tension, just a wonderful freedom to live life on your own terms. I suppose I will have just a tiny moment of that when I leave the job. Back in the fall, before I had any inkling of all this, I made plans to take a vacation in late April.

After five intense years of study and testing, I finally passed the final diploma certification in wine with the Wine & Spirit Education Trust. Once a year, in April, they have a graduation ceremony in London for anyone who passed the exam. I decided to treat myself to that experience, so just one day after I leave my job, I fly to London for five days, then on to Portugal for another four days to visit friends. I return on May 2.

That means, after my fun excursion to celebrate both my success and my freedom, I will wake up on Monday, May 4 for the first time with no job, no structure, no script . . . and the burning question of “Who am I now?”

I know this was a long ‘first’ post to open up my new Substack world - but I felt like I wanted to be open and honest about my journey. Yes, I will be writing about my upcoming book and about what it’s like to be a first-time author . . . but I also feel like I need to be real about trying to live what I wrote about.

I never thought it would be me, but I am a living personification of the “Bewildered Beginner.”