Those who have been following along know that I have made some big changes to my life this year. Many of them have been difficult, but I’m hopeful that they are the right choices. I’m hopeful that they’re carrying me in the right direction.
However, recently I’ve found myself feeling hesitant when people ask me if I’m ok. It’s odd; normally that’s an easy question to answer, yeah, I’m fine, just tired, it’s been a long week.
But lately it’s been a little deeper than that. I don’t know how fine I am right now.
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Maybe the most honest thing I could say to people who ask me if I’m ok is that I will be.
I’ve been struggling with debt and financial uncertainty since March 16, 2020. If that feels like a weirdly specific date for something as nebulous as financial uncertainty then you’re right to flag it. But it’s seared in my mind forever as the date that we began COVID-19-related lockdowns in Canada. March 16 was a Monday. I had just finished a major renovation of my massage therapy clinic over the weekend. Monday was literally the first day patients would have experienced the renos and they never got the chance. Moments like that stick with you.
But back to the present. That financial uncertainty has followed me to today. Across two serious relationships and over half a decade of my life. Part of it is the sheer volume of debt. At worst I owed almost $200,000. That doesn’t go away overnight. But I’m recognizing that part of it is clearly me. There is a version of myself that said yes to all the decisions that led to that, a version of me that failed to say, “no, that won’t work for me.” I truly believed that hard work and consistent effort would allow me to overcome that debt and continue to provide for those most important in my life.
I was wrong. Or, at the very least, I was misguided. That kind of debt is life-changing. That kind of debt keeps you up at night. It makes your heart skip a beat anytime you get a utility bill or the end of the month approaches. It makes every day off, every holiday stressful. Will I have enough? Probably not.
So I made some changes this year. I ended a relationship with a really special person. We owned a house together and were actively trying to start a family together. It was and continues to be really hard. I filed a consumer proposal. For those not familiar with the term, think of it as an alternative to bankruptcy. It reduces the overall debt that you have to repay and makes the remaining balance interest-free. There are financial consequences. For example, right now I only have access to a credit card with a $300 limit.
That’s not impossible to work with, but it does make my life smaller for a time.
And that’s, I think, where the resistance comes up for me when people ask me if I’m ok. Objectively, I’ve made some hard choices that I hope will pay off in the future. Subjectively, my life is still a mess. It’s the first of the month today; I’m two days late publishing my post as I stayed late the past two nights to make sure I had enough to cover rent this morning.
To stay on top of all my present expenses while paying down my previous debt doesn’t leave a lot of margin. And yet, I know that’s what I need to do.
A good friend of mine told me a story about how he paid off debt when he was at his lowest. He took his monthly income and reduced it to a daily spend amount. So each time he had his phone or debit card in his hand he would ask himself, is this worth it?
It’s a fair question. So many decisions get judged too quickly by how they make us feel in the moment. A bad decision can feel good immediately. And good decisions can feel terrible for months.
So on the nights with too much free time or the grocery store checkouts where you leave some treats behind, I don’t always feel amazing. When I think about the lives my friends are building with their partners, the children they’re raising, the goals they’re achieving, I know I’ll feel behind sometimes. Not everything is ok right now, and that’s ok. It’s a weird feeling to not have anything to hide behind: to have your messy life on display for your friends and family to see. It’s not how I imagined my 30s to be.
So am I ok? It depends. Some days are better than others. But I will be.
If this resonated, share it with someone who might need it.
Thanks for being here.
Jack
P.S. I’ve been thinking a lot about pressure and freedom lately.
I recently published a short essay called The Freedom Paradox.
It goes deeper into some of what I’ve been working through.
eBook + audiobook here:
https://jackjohnstonwrites.gumroad.com/l/freedom-paradox


