Thoughts on Becoming a Hopeful Pessimist

Housesitting in Canada. Traveling solo around the west coast. Freelance writing. How did this become the new normal?

I have zero regrets about making this choice. I feel more myself than ever and deep gratitude most of the time. Sometimes, I imagine my life in montage—a series of snapshot moments of what my life looks like right now. I think there could be two possible montage sequences for the trailer of my story.

Montage Sequence #1: A shot of me strolling on the beach at sunset. Driving on a road ribboning through forests and breathtaking shots of the Pacific Northwest. Another shot of me sitting at my computer, fingers flying as I chase down the words for another writing project. Laughing on the phone as I connect with a friend from back home. Another of me deep in conversation with some random friend I’ve met in a coffee shop.

All of these are all regular occurrences. This is real life, and sometimes it floors me.

But here’s another, also very real montage happening simultaneously:

Montage Sequence #2: Me, sitting on the couch alone on a Friday night, when the “Are you still watching?” pop up comes on Netflix. Sitting in bumper-to-bumper traffic on my way home from a downtown coffee shop. Bloodshot eyes staring at a screen, deleting the sentence I’ve been trying to write for the last hour. Sitting in my car, trying to work up the nerve to walk into a meet up where, once again, I don’t know anyone.

It seems glamorous from the outside. People often admit envy when I share what I’m doing. But there are terms and conditions to this life. Things I agreed to sign up for when traveling solo and choosing a career that requires large chunks of time alone with my thoughts.

Just like we don’t read the fine print on the websites we join or the products we buy, it seems we spend a lot of our lives carefully avoiding the reality of our own disappointments and frustrations, the inevitability of ache in the paths we choose.

We pine after constant bliss, thinking it exists just within of our reach. We pursue the promise of an ideal existence, convinced if we can just be productive enough, clever enough, fill-in-the-blank enough, the best versions of our lives can finally start.

I’m living a life I love, and I’m not happy all the time. Montage Sequence #1 comes in a package with Montage Sequence #2. That’s the way it is.

Work life will never be pain-free. Conflict-free relationships where the other person totally gets me and loves me perfectly don’t exist. I’ll never be this elusive perfect version of myself.

These pessimistic revelations aren’t leading to a defeated despair. Ironically, coming to terms with these “terms and conditions” is a huge sigh of relief. A hopeful embracing of what is possible.

It seems all of us are trying to find the best ways to be fully alive. And the motivational slogans encouraging us to “Make Every Day Great!” and “Choose Happiness” seem like a logical strategy.

But how much deep joy have I forfeited in my demand for constant happiness?

What if my crusade for positivity was actually robbing me of the nuanced beauty of the current messy splendor?

What if admitting my limits and being hospitable towards my mundane moments actually freed me?

I’m testing out this hopeful pessimism, and it feels like a sigh of relief. In a nonsensical way, not needing to be happy all the time is making me a happier person.

Please don’t confuse what I’m saying with existential cynicism or an apathy towards growth.

It’s just that sometimes optimism requires a blindness towards the less desirable emotions. And I’m not willing to submit to that anymore. I’m tired of the hustling to diminish my weaknesses. I’m not attracted to the kind of busyness aimed at distracting me from the presence of heartache.

And I’m seeing a tyranny in the Either-Or. The All-Or-Nothing. There are actually more opportunities for joy when there’s more margin for accepting the not so amazing moments.

The upside of pessimism is how it helps me say “no” to things cluttering my life. Admitting the finite-ness helps me steward the time, energy, and resources I have in a more effective way. It provides a lens that reveals the ways the grass may not actually be greener when I start to compare or assume.

Maybe this is just an optimist’s step into deeper joy. Nuanced, messy, and full of splendor.

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