The Year I Lost My Way — & My Wildest Dreams Came True

Today Show appearance, August 16th 2019.

On January 1, 2019, I was lost.

Over the year prior, though I kept it quiet, I’d been losing a lot.

I was losing several people I loved deeply.
I was losing my dog.
I was losing the everyday life I cherished.
I was losing the future I’d planned on.
I was losing my cover.
I was losing my security.
I was losing my equilibrium.

I was losing my way.

Loss — great loss — is a powerful force. It is a wave that crashes over you, tossing and turning you as it pleases, disorienting any sense of place and purpose and control. It is everything the world steers you not to be — frightened, insecure, vulnerable, messy. Human.

As hard as I initially tried to plug every leak and mend every crack, onwards into 2019 my losses only continued.

But something unusual happened the more I let go and lost things I’d been holding onto with a white-knuckled grip, the more I lost other things that were holding me back from lifelong dreams. And not just any dreams…these were the kind of dreams you thought about as a kid when you laid in bed at night and imagined your future with starry eyes, the kind of dreams that after all these years you still begin each New Year fantasizing about before landing on something more doable and pedestrian like “fit into my old jeans”.

And then things got really strange…

  • By late January, the essay was shared by the venerable kottke.org.
  • By March, I was flown out to New York City to film a documentary with a high profile team of award-winning filmmakers who’d read my essay and knew immediately it needed to be their next film (due out in 2020).
  • By May, I was recruited by and signed on to be represented by one of the world’s top literary agents (and agencies).
  • By July, a television celebrity named John Edward shared my essay on Twitter.
  • One day later, Bindi Irwin, the daughter of the late “Crocodile Hunter” Steve Irwin, shared it on Twitter, saying it left her family in tears, and urging everyone to please read and share it.
  • Through July & August, more celebrities and all kinds of people all over the world — spiritual leaders, physicians, mothers, sons, brothers, husbands — started sharing my essay. My inbox was filled with hundreds of emails from readers whose lives were impacted by that essay…the essay I wrote one night alone in my apartment.
  • By August, I was sitting on a barstool in the iconic NBC Studio 1A on live television in front of two million viewers being interviewed on the Today Show by all four anchors, including Al Roker whom I’d watched on television as a young child with my Grandparents. (They would have bursted with joy to see me on that screen.)
  • By November, my book deal was being floated among the top publishing houses, with immediate interest.
  • And all the while, I’ve had a big job at a company I love with incredible, wonderful people.

As the end of each year closes in and a new one hovers on the precipice, we tend to give our previous twelve months a binary label — either it was a “good” year, or a “bad” one. On its face, it appears 2019 was a “good” year for me.

In 2019, it looked like I was winning.

But the truth is that every “win” I had was the result of losing a piece of myself, and bracing to find a new way forward.

As I began losing people and things I’d been clinging onto tightly for many years, and as the suffering circulating through every part of my body felt unbearable at times, I lost other things worth losing.

I lost my fear of writing in my own voice.
I lost my fear of speaking up, everywhere.
I lost my fear of what others think of me.
I lost my need to hide in the shadows of others.
I lost my need for alcohol and sugar and unhealthy foods.
I lost my need for other people.
I lost illusions of my childhood that weren’t serving me.
I lost my fear of being alone.

I lost my anchors, and I started to swim.

For a while there, I was swimming fast with the tides in my favor. It seemed I was racking more wins than losses. The world started to make sense to me again. I could reason a purpose for the losses — it gave me more than it took away.

And then things got really tough…

It turns out there is no such thing as getting more. There is no such thing as winning. Few ever talk about it or make it obvious, but the truth is that there are things you lose even when you win.

Few ever talk about it or make it obvious, but the truth is that there are things you lose even when you win.

There are people who suddenly disappear once you start winning, people you’d thought would have been the proudest. It was one of the most gutting realizations for me, and I will never fully wrap my mind around it. But the counterbalance is that in their place, there are people whom you never realized were there all along, right by your side. People who you didn’t know were watching from the rafters and cheering as you ran down the field with the ball.

Still, when you “win”, sometimes you lose people you loved. People you thought loved you.

There are ways you change when you win, healthy changes like more confidence and agency. And with that, the way you see the world changes. You start understanding better what you have to offer the world, and how your current choices may not support that. The trouble with your wildest dreams coming true is that you can never go back to an existence where you aren’t striving towards it. To make that choice, you have to make room for it — you must lose some things. Those aren’t easy choices, by the way. Sometimes when you win, you lose a sense of comfort and community and sure-footedness as you begin to carve a new pathway.

When you win, new opportunities arise and suddenly you are thrust into a competitive world where you are bound to lose, a lot. Every athlete or actress you admire seems to win a lot, but you have no idea how many positions or parts they are passed over for, continuously. Winning, as it turns out, involves way more losing than not trying did. When you’re not trying, you can feel like a loser. But when you’re winning, you actually are a loser — all the time.

When you’re not trying, you can feel like a loser. But when you’re winning, you actually are a loser — all the time.

Winning wasn’t exactly what I imagined when I was a kid, laying in my bed at night with those starry eyes. In all reality, winning was not an accumulation of more life stock. Nor was it a subtraction. Rather, it was a reorganization, at certain times inexplicably beautiful and other times quite painful.

In all reality, winning was not an accumulation of more life stock. Nor was it a subtraction. Rather, it was a reorganization, at certain times inexplicably beautiful and other times quite painful.

When my wildest dreams started coming true, it was as if the universe was revealing to me that “wins” and “losses” as we account for them are merely illusions. There are things you need to lose in order to win. And there are things you will lose once you win.

After all, in losing my way, I found…myself.

It makes sense that we struggle to avoid loss. Good things are worth fighting for. But the world also tells us from early-on that loss is a debit.

Losing is bad, they say.

Losing your youth.
Losing your job.
Losing your company.
Losing your marriage.
Losing money.
Losing sleep.
Losing health.
Losing control.
Losing your mind.
Losing life.

Yet paradoxically, loss is one of the most powerful instruments of growth. Loss is a series of defining moments if you are brave enough to suffer through them, in their entirety. It is loss that first shakes you, but it is ultimately suffering that shapes you— one way or another. Suffering delivers you to the places inside where your biggest fears loom. And it is neither reality nor money nor circumstance, but rather your fears, that are keeping you from your dreams.

Suffering delivers you to the places inside where your biggest fears loom. And it is neither reality nor money nor circumstance, but rather your fears, that are keeping you from your dreams.

So if we continue relegating loss to the “bad” file, and if we never learn to lose and suffer successfully, how are we to grow? How can our wildest dreams ever come true if we don’t begin to rewire our perception of winning and losing?

It’s time for a new understanding of loss. In our Western worship of “more”, the accounting of dreams is lost on us. Few ever make their ledger public, for all to see. But I guarantee that if you peeked at the annual gains and losses of those who achieve their dreams, you would discover something illuminating — their losses would be as substantial as their gains, and so interdependent that it would be impossible to have one side of the balance sheet without the other.

I won a lot in 2019. And I also lost a lot, and suffered a lot. And so, this January 1st, when I look back on my previous twelve months, I will not say it was “a good year” or a “bad” one.

Instead I will say it was a year of important growth.

For all its moments of elation and suffering and uncertainty and beauty, there is just one thing of which I am certain: The true measure of a year is not how much you lose or how much you gain, but rather it is how much you grow.

This year, instead of hoping for more of one thing or less of another, I offer a different kind of New Year Resolution:

May all of us be trusting enough to accept loss, brave enough to suffer through it, and wise enough to know that losing our way is often the first step in finding the path home.

The cave you fear to enter holds the treasure you seek.
- Joseph Campbell

The Author and her best friend and loyal companion, Virginia Woof.

I write about serious tech stuff for work. But here, I tell true tales from my wacky, wonderful life. (read more: www.christenobrien.com)

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