The Practice of Uncertainty

Faith doesn't make it comfortable. It just makes it survivable.

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I’m doing something different this week, partly because I’ve decided that I’m going to consistently do different things this year. I’m revisiting something I wrote about last week, with the intention of building on it. Not just because it’s distinct from my usual rhythm, but because I think it’s important.

(At least, it seems important to me; which means that it might be to you too.)

One recent morning, I started the way a lot of winter mornings start in Ottawa: in the dark, half-awake, standing behind a snowblower and staring at a driveway that looked like somehow, in my sleep, I’d quietly pissed off the snow gods and they were letting their displeasure be known.

I was annoyed. Not dramatically or anything. Just that low-grade grumpiness that says, “Really? Again?” The kind that shows up when you’re doing something you didn’t choose, on a schedule you didn’t set, because the weather just doesn’t give a shit about you or your plans.

But as I pointed out last week, I caught myself thinking something embarrassingly obvious:

“I cannot control the weather.”

(I know. Deep thoughts, Tim! Really profound stuff…)

But what surprised me was what came next. Because as soon as I noticed what I couldn’t control, I noticed what I could.

I could control how I showed up.

I could control whether I stomped around resentfully like a toddler, or whether I treated it like a simple job to be done. I could control my pace. My attention. My attitude. I could even control the story I was telling myself about the whole stupid thing.

So I tried on a different story:

As I worked, that little shift in framing bumped into something I’ve been wrestling with for the past while: the difference between goals and uncertainty.

Last week I talked about being done with goals—at least for now—despite the fact that they’d been very useful in helping me build an amazing life. This year, the whole goal-setting process felt different. Wrong somehow.

Not because I’ve stopped believing in putting forth effort, or driving change. But because I started wondering whether goals were doing something sneaky to me.

Goals are great for getting things done. I’ve seen that in my life.

But I’m no longer convinced they’re great for changing who you are.

Sometimes goals are a tool. Sometimes they’re a shield you hide behind, allowing you to tell yourself that this is the year you’re finally going to make that change. If you’ve had goals on your list for multiple years and they haven’t advanced forward in any really meaningful way, you know exactly what I’m talking about.

So I settled on the word “Uncertainty” as my theme for the year.

Uncertainty is the opposite of goals.

• It implies that you don’t know what’s coming.
• It implies that you don’t even know what you’ll do.
• It implies that you might work on the most random, unpredictable thing, and end up farther from what you thought you wanted.

Scary stuff indeed.

It’s not that I don’t have faith it’ll work out. I do. But faith doesn’t make uncertainty comfortable. It just makes it survivable. And I’m learning that the work isn’t to eliminate the discomfort—it’s to keep moving while it’s there.

Which is why I made this video about why I’m embracing the theme of Uncertainty for the year.

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I’ve wanted to create video content for years but haven’t—because I’m scared to, and because I know I’m not good at it (yet). So I did it anyway. Despite advice from everyone, and from AI, telling me NOT to put my energy into creating video content. That’s what uncertainty looks like in practice.

Goals are about knowing what you want and what you’re going to do.

Uncertainty is about admitting that you have No. Damn. Idea. But committing to lean in and do the work anyway. Not knowing if it will work. Sure that you’ll embarrass yourself somehow. Allowing your curiosity to get the better of you.

Sometimes in life you’re just going to need to shovel. It might be snow. Or it might be shit. But one thing is certain: you’re going to need to shovel.

So I encourage you to pick up your shovel and join me in the pursuit of your curiosity.

Show up, not because you can predict the result, but because this is what it means to practice the person you’re trying to become.

PS: Hit reply with one thing you’re doing this year that scares you a little. One sentence. I’ll read every one.

Quotation I’ve Been Pondering

—Joseph Campbell

Journal Prompt

Until next week!! Work and live well. Tim Did someone awesome forward you this email? Sign up here to ensure you get my latest content. Do you know someone who would benefit from this content? Please pass it along! ♻️ Let's fix what your job broke. If you're finally ready to take control of your work life and build something that works for you, here's exactly how to start: ​Book a Free 30-minute Clarity Call. Not sure where to start? Let's talk. We'll look at where you are, where you want to be, and whether working together makes sense. No pitch - just an honest conversation. ​Book a 90-minute Strategy Session ($175 CAD). You've got a specific problem. Let's solve it. One focused session to diagnose why you're stuck and map out your next moves.

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