Field Notes on Starting Over: Note #2—Expectations vs. Reality (Midlife Edition)

The humbling reality of having expectations

English poet, Alexander Pope said, “Blessed is he who expects nothing, for he shall never be disappointed.”

So, I guess that makes me…cursed?

As I stumble along this new path I’m paving for myself, I’m making note of some uncomfortable truths I’m learning on the way. One of those truths being that I may have expected too much.

Expectation: I’d have my shit together by 40.
Reality: I lived life in reverse.

I got married in my early 20s when most of my peers were partying. Then in my 30s, I dropped out of my life in the U.S., moved abroad, and lived the kind of chaotic, freewheeling life most people get out of their system earlier. Now I’m starting over in every way — solo, jobless, rootless — at an age most people usually associate with being well established in their career and family life.

Expectation: My little passion project would instantly take off.
Reality: People don’t owe you their interest.

I figured if 50,000 other people could do this, so can I! I thought my Substack and online book club would take off overnight, simply because I cared about it deeply and had a vision. But passion ≠ audience. Slow growth is humbling. And sometimes the only thing keeping you going is the belief that your voice still matters, even in a quiet room.

Expectation: I’d just apply to jobs and the offers would come flying in.
Reality: Breaking into a new career in your 40s is like shouting into the void.

I’ve always gotten any job I applied for. I would walk into interviews relaxed and confident, knowing I already had it in the bag. Now that I’m pivoting careers, however, my outbox is full of job application emails for which I receive nothing but crickets in reply. The skills and experience I have don’t “translate” well to other fields, and it’s forcing me to reevaluate not just my résumé, but my identity—and serving up a big piece of humble pie in the process.

Expectation vs. reality is often at play in my kitchen as well

Expectation: I can live anywhere and make it work.
Reality: I can’t. I tried, but I can’t.

I have lived and worked on five different continents. I have always been adaptable, flexible, openminded. Learning foreign languages has always come easily to me. I had heard about other foreigners who had moved to Japan and ultimately left earlier than they had planned because the struggle with assimilation, isolation, and depression was too great. I heard from foreigners who decided to stay and still struggled with these issues 20 or 30 years on. But I thought “Naw, that won’t happen to me. I’m a citizen of the world! I can fit in anywhere!” (Pause for spit-take). Maybe Japan wasn’t on the right planetary line on my personal Astrocartography map; maybe Venus wasn’t conjunct the North Node when I moved here. Whatever the reason, I couldn’t make it work. Yet another humbling realization.

Expectation: I’d have a well-watered, fruitful money tree thriving in my yard. Reality: Charlie Brown’s Christmas tree is putting my sapling to shame.

Because I trusted the wrong person, my entire seed bank was obliterated. Now, the lush, bountiful harvest I expected to have reaped at this point in my life is non-existent and I’m left holding a branch, trying to pretty it up with second-hand baubles.

Aside from learning to keep my finances separate from a partner, I’m still not sure what grand lesson losing my entire life savings was supposed to teach me. But it has given be someone to focus on when I practice Metta (aka loving-kindness) meditation where the goal is to cultivate kindness for all beings everywhere including lying, cheating, thieving arseholes 😊.

C’mon, little guy!

Though I acknowledge I have had many high expectations for myself and my life that haven’t quite panned out, I can’t say that I’m woefully disappointed. Humbled—maybe even a little abashed—but not disappointed. I may not be pleased with the outcome of certain situations, but I’m not sorry that I had expectations.

Because expectations meant I believed in myself. I believed in myself so hard, I sprained something.

Expectations are really just better dressed hopes.

And I had hope in spades. I could envision a life that stretched beyond the reality I was living. Was there sometimes an expectation/reality gap? Sure. But it didn’t stop me from showing up for myself.

If having high hopes is a crime, then lock me up with some crafting supplies and my well-loved copy of The Alchemist. I’ll be over here working on my vision board…with one eye twitching and a résumé no one’s reading.