Ask Me Next Year

On goals, boredom, and the fine edge of terror

I’m turning 43 this week. A non-descript, no-woman’s-land number in the birthday continuum. Supposedly past the punctual unraveling of 39 and 40, settling into the messy middle. That phase when you’re ready to stop giving quite so many fucks, but still have some fucks left to give.

And the truth is: I’m bored as fuck.

At the beginning of this year, I made an uncomfortable decision to set down my relentless pursuit of goals. I put down the ruler that charted out my annual, quarterly, monthly, and weekly goals and focus areas. I abandoned the symbol-coded bullet journaling. I gave my rainbow colored pens a sabbatical. I decided to pursue my worth as inherent, not earned.

Seemed like a great idea.

Then I had another great idea: let me catalogue my insights and progress! I spent a Saturday afternoon building a GPT based on my journals, my prior goal structure, and my new commitment. In hours of robe-adorned, coffee-fueled GPT vibing, I created a methodology for weekly reflection. I restructured my handwritten note-taking style to a digital format that my GPT could easily analyze. I created a complete phygital system (part physical, part digital): a digital notebook for tasks, a physical notebook for journaling. I diligently wrote weekly journal entries. I listed what I was noticing, what I was letting go, and what I was living in. I shared my journal entries and digital logs with my GPT, mining further insights and reflections. I definitely made sure to do this every Sunday.

Wait a minute.

You see where this is going.

Somehow, even in the absence of rigorously structured goals, my goal orientation crept back in. I was architecting a new, elaborate framework by which I could continue to evolve, grow, learn, and gain insights in my goal-less endeavor.

Once again, I set down the structure.

But I still needed something. Some form of accounting for what the hell I’m actually doing or need to remember. After reading Oliver Burkeman’s Meditations for Mortals, I settled on a compromise: logging a simple, unstructured, unfiltered list of to-dos to quiet my monkey brain on a Sunday night; logging a simple, unceremonious list of things I had done throughout the week. Less glamour and revelation, more facts and humility.

My workdays are often long and chaotic. On a typical day, I might lead 10-15 meetings. I am in a perpetual state of context switching. In an hour, I might go from: business development mode → admin mode → problem solving mode → wine biz mode → client deliverable mode → mom mode, all compressed into two 30-minute meetings, endless Teams chats and text messages in the background, and the slight breath between it all.

At the end of days like this, my brain feels like a hard-boiled egg. Dense, hot, and stubbornly unwilling to yield the protective shield around it. Even as I move through the daily rituals of unwinding – taking a walk, making dinner, convening over a meal with my family, reading a book, turning the lights out early – I feel my brain cooking, racing to catch up with whatever actually happened in that jet-fueled window from 8 am to 6 pm.

On weeknights, I wait for my brain to unfurl according to a schedule. On weekends, the opposite occurs. I indulge in two days of quiet, agenda-less living. I rest. I make food. I walk. I connect with friends and family. I’ve spent so much of my life in a loop that demands constant striving, hustle, go, go, go. My work day still models that mindset. But, outside of that context, I find myself slowing down dramatically. Observing my plants. Taking a stroll. Running little errands. Planning dinner. Making dinner.

I am so excruciatingly bored.

Whether the weekday grind or the weekend respite, I arrive in the same space: restless ennui.

Old me would have a simple fix to this problem. Take on a new project! Set a new goal! Become fluent in Japanese! I’ve gotten better at spotting the telltale signs, but I still struggle to lay down this habit. In the course of twenty minutes of Saturday couch lounging, I will entertain any number of exciting future realities: community theater, visual arts, a new wine degree, mahjong mastery, reading the complete works of Shakespeare, taking up rollerskating.

I haven’t acted on a single one.

My mental urge to “solve” my boredom doesn’t seem to dissipate. I want so badly to extricate myself from my restlessness. But, deep down I believe I’m here for a reason.

The more I sit with my listlessness, and the more I sit with my passing fancies, the more I realize they’re a cover for something else entirely.

In a moment of frustration and self-quandary, I went back to my non-goal goal-GPT for input.

Annoyingly, the robot had thoughts.

“Are you too afraid to fail that you aren’t willing to try anything?”

Annoyingly, the robot wasn’t wrong.

Side note: this was also the moment when I completely disengaged from further interaction with the GPT, as it bordered on psychotherapy. Kernels of truth are best delivered by humans, not robots.

Because I have been so historically goal-oriented, I struggle to pursue anything without:

• An endgame

• Confidence that I’ll excel

• A gold star

My flights of fancy lack the characteristics for unlocking gold-star-level achievement. They aren’t nearly sexy or public enough. And, they might turn out to be things I objectively suck at. I’m pretty miserable at riding a bicycle, as an example; do I really want to rollerskate?! That could be… bad.

Beyond the fear of failure or fear of not being “the best”, there’s something more. Something bigger that’s holding me back.

I don’t want to pursue for the sake of pursuing. I want to feel something. I want to feel the spark in my veins that signals I’m on the right track. I want to feel that thrill of inspiration, that twinkle in my eye, that sense of possibility mixed with apprehension.

And right now, I don’t feel it.

Maybe, just maybe, that boredom is the fine edge of terror. Terror in failure. Terror in a lack of vitality. Terror in not knowing what you actually want or where to go from here.

And maybe, just maybe, that’s the whole damn point.

Maybe the most terrifying idea of all is: this is just life.

In midlife, you weigh two polar realities: you aren’t going to be and do everything; the version of you who was going to do it all has invested in their 401k and is planning toward retirement. You aren’t gazing upon endless potential futures ahead. The window of possibility has narrowed – not closed, but narrowed.

Yet, you still want more: more growth, more mystery, more self-discovery, more adventure, more evolution. The wanting is subtler now, and the pull toward it requires more bravery.

As I approach this year’s squishy, non-number birthday, I am living inside this messy middle. Of letting go, of giving everything, of mourning what isn’t, of celebrating what is, and of relishing and questioning who I am, who I am not, and who I have yet to become.

Maybe that’s the strange, awkward wisdom of midlife in full bloom. Maybe the wisdom is in accepting that perhaps there isn’t a bigger point. Maybe it’s always both. Maybe it always has been.

I don’t know. Ask me next year.