When Failure Sets You Free

The surprising gift of failing at all the “right” things

“It does not do to dwell on dreams and forget to live, remember that.”
Albus Dumbledore

Do you remember the first time an adult asked you what you wanted to be when you grew up? When you’re young, you answer honestly and with your whole heart. And if your experience was anything like mine, your dream was probably met with something like, “You can’t make money doing that,” or, “What kind of life could you make with that?”

Now that I’m in my mid-30s, I can confidently say I’ve made some decisions that were… let’s call them “financially unhelpful.” We’ll get into the details another day, but for now, just know this: I’m in a financial situation that has taught me exactly how valuable money can be. Cue the Joni Mitchell lyric in the background: “You don’t know what you’ve got till it’s gone.”

Even with all the mistakes I’ve made, and even with the many things I haven’t achieved that I once hoped I would, I’ve gained two very real perspectives.

First, it is incredibly painful to work all day and not be able to keep any of the money you earn. Living above your means hurts. Making less than the life you want is exhausting in every possible way.

Second, once you’ve tried everything respectable and responsible and it still hasn’t led you to where you hoped to be, something interesting happens. The quiet voice inside you becomes a little louder. And it becomes a lot less scary to listen to.

Mine says, “I’d like to be a writer.”

Timing is strange. You can hear something once and feel nothing, and then hear it again years later and feel it hit you like a wave. One quote did this for me:

“You can fail at what you don’t want, so you might as well take a chance on doing what you love.”
Jim Carrey

The first time I heard that quote, I was freezing in a dingy basement apartment in Toronto. I was probably at one of the lowest points of my life. I had stopped working for the first time in adulthood and was focusing entirely on my studies to become a massage therapist. It was a lonely, anxious, uncertain time. I was mediocre at a skill that demanded real practice, and it was a shock to my system. I’d always done well academically, but I had avoided anything hands-on up until then. I shrugged the quote off. I needed to be responsible. I was building a career I thought made sense. Something useful. Something that added value. Something my parents might one day approve of. “Maybe you could start your own clinic,” people said. “There’s money in healthcare.”

Ten years later, I’ve failed at more things than I care to count. Yet massage therapy wasn’t one of them. I’ve been practicing for over a decade, and oddly enough, it might be the perfect career for me. Not because it’s my dream, but because it gives me the stability and the space to pursue the thing that is.

That brings me back to the Dumbledore quote. Like most advice, it’s brilliant only when the timing is right. If you’re stuck in inaction, then yes, you need to stop dreaming and start living

But after ten years of working hard at something my heart wasn’t fully invested in, I’ve learned something else:

You need to be behind what you’re working toward. Fully.

This doesn’t mean you get to hide in your parents’ basement and play Xbox while the world (or your parents!) pays your bills. Responsibility still matters. But once the basics are covered, once you are taking care of what needs taking care of, the rest of your life should not be devoted to fulfilling other people’s dreams. Service to others is wonderful, but it has to be woven into your story, not replace it.

So if you’re a people pleaser, a perfectionist, someone who feels everything deeply and worries endlessly about disappointing others, welcome. I get it. My strength is research and distilling information, and I’m going to share what I learn as I figure out how to build a life that finally belongs to me.

I don’t know if any of this will be helpful. I don’t know if anyone will read it. But honestly, that doesn’t matter anymore.

I’m a writer.
I’m sharing what I think.
I’m trying to offer something useful.
And, most importantly, I’m finally choosing myself.

I’ve already failed in all the “safe” ways. So I might as well take a chance on something I love.

If any part of this felt familiar, stay awhile. I’m rebuilding from the inside out, and you’re welcome to walk with me.