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.

Allie Cats: The Whimsy of a Creative Life

Creativity has always been a common thread running through my story. From the imaginary worlds woven into the landscapes of our unfinished basement growing up to the desk piled high with art supplies and magazine clippings in my last apartment, I need creativity to feel whole.

I’ve cycled through various mediums and outlets of creativity. Throughout various times, creativity has manifest itself through dance, acting, sketching, photography, collage art, upcycled furniture, oil pastels, pottery, book rebinding, acrylics, and poetry writing.

Allie Illuminated Creativity

Art was just a way of being for me. But it’s also often been an avenue of freedom.

Acting in high school helped me break out of my painfully shy shell. Journaling through mixed media in college gave voice to an ongoing struggle with depression. Writing on this blog was a lifeline that brought me to a career that feels much more in line with who I am.

This ongoing conversation with creativity has been deeply personal, but mostly a private affair. I filled dozens of journals with writing before attempting to share my thoughts online. I made a few attempts to sell my art, but there was a scant number of interested buyers. When my tentative hopes were met with relative silence, I slipped away from the limelight, tail tucked between my legs. Clearly, I didn’t possess whatever elusive quality the “real” artists had to be successful.

But the success of selling art and the need to create are two very different things. So I kept creating. I made agreements with myself that, for awhile anyways, my art was just for me. It didn’t have to be good. I just had to keep creating. When the bruising of my ego had faded a bit, I kept the possibility of selling art again in my Someday Pile.

Allie Illuminated WatercolorWatercolors have been the focus of my creativity in the past two years. I love the collaboration of pigments and water spilling out on the page. Varied by brush size and the timing, the art is a conversation. Learning the language of watercolor was playful, therapeutic. Just me and the paint and the water.

Right now, traveling around the west coast and house sitting along the way, painting has become a part of my rhythm. Several nights a week, in the quiet spaces of my evenings alone, I paint.

Most of these unfamiliar places I’ve been calling home for a few weeks at a time are housesitting jobs. Strangers welcome me into their homes to care for their pets while they are away. This level of hospitality is rare today, but it has been an unspeakable gift.

So when I was welcomed into the home of a Canadian family this October, I wanted to find a way to thank them. When I first arrived in their home and getting familiar with things, they introduced their two cats.

“Harley is 19 1/2 years old. He’s starting to get frail, but he’s really friendly. We kind of think of him as an old gay art dealer. Very posh and snooty to some, (mainly the other cat) but he’s got a heart of gold.”

Just then, the other cat Oskar came skirting around from behind the couch. “And that’s Oskar. I suppose he would be like a reclusive man living in the woods that believes in conspiracy theories. Not that bright, and really skittish, but sweet once he warms up to you.”

So, naturally, my gift to them was a whimsical watercolored rendition of Oskar and Harley.

Allie Cats Oskar

Allie Cats Harley

I didn’t realize that I had unwittingly stumbled onto potential greatness. Why?

Because people love their pets.

And because we all see the animals we love as having human traits.

And to see these pets as the people we know them to be is delightful.

And because the world needs more whimsy and delight.

Allie Cats | Duke

Allie Cats | Butler Dog

Allie Cats | Smalls | Sailor Dog

Allie Cats | Hawaiian Hikers

And now, I’m finding myself painting portraits of other people’s pets several nights a week! Unexpectedly, I stumbled into this niche market. And it’s working. (It may have everything to do with obsessive love of animals and not as much to do with my artistic genius.) But that’s not the point.

The point is that this is the unexpected and funny way that creativity, inspiration, and opportunity interweave. The success was in the declaration to myself that “the act of creating stirs an undeniable, soul-satisfying need, and that alone justifies worth.”

These are the implications of living a creative life. We vision cast and we strategize and we align our lives with where we want to go. And then we find ourselves delightfully caught off guard by new possibilities we couldn’t have imagined.

I wouldn’t have it any other way.