The Art of Starting Over - Again (and Again)

Whether it’s relationships, creative projects, identities, or simply how you think about yourself

I give you this to take with you:
Nothing remains as it was.

If you know this, you can
begin again, with pure joy in the uprooting.

―Judith Minty

There are some beginnings we choose. And others that choose us (kinda like family, right?). Some beginnings feel hopeful and warm like a beautiful sunrise. Others arrive loud and harsh and abrupt without warning like a thunderclap in the middle of the night (that has you sitting up in bed screaming). The ones that are unwanted, disruptive.

Either way, we’re left standing in a kind of limbo, whispering: Okay... so now what?

Here’s what I’ve learned, over and over again:
Starting over isn’t a single decision. It’s a hundred tiny ones.

After all, that’s what life is, right? A series of decisions, one after the other and each one leads us down one of an infinite number of paths — or potentialities, as Aristotle said.

And these new beginnings aren’t always bold and obvious and in your face. More often, it’s mundane, almost invisible. It’s eating something nourishing after days of survival-mode snacks (please get all the crackers out of my house! Leave the cheese, thanks). It’s standing in the shower and letting yourself cry (isn’t there something so therapeutic about a good shower-cry?). It’s noticing a new possibility arise in your mind—and choosing not to push it away this time.

Sometimes, starting over is less about doing something (taking a step down a certain path) and more about allowing something: an acceptance, a softening, a shift, a breath.

It doesn’t always look brave.

There’s this myth that new beginnings are bold and decisive. That we burn the bridges and rise from the ashes with dramatic flair - a new and totally changed person.

But real-life hitting of the reset button is quieter than that.

It might look like brushing your teeth after a week of not caring. Or opening a new blank document even though you’re scared the words won’t come. Or texting a friend after months of feeling unreachable. Or applying for a job even though you’re not sure you believe in yourself yet.

It doesn’t have to feel brave to be brave.

In fact, that is what bravery is, isn’t it? Doing something in spite of the fear or uncertainty! You still feel scared but do it anyway. Courage often comes disguised as routine. Or hesitation. Or choosing to try again when nobody’s watching (which, really, we shouldn’t need to wait til others are paying attention to take a first step towards starting over!).

Sometimes you start over without meaning to.

You’re just trying to survive, trying to make it through the day—and one day, you realize you’ve become someone new. It didn’t happen overnight or all at once with a magical ‘ta da!’ sparkle of newness. But slowly, and probably imperceptibly. You outgrew the old story while you were too busy just getting through the day, just holding everything all together and without even realizing it, you became someone new.

And that counts too. You don’t always need a defining moment of reinvention. Sometimes all you need is a pause and then the willingness to keep going.

“You’re not starting from scratch. You’re starting from experience.”

It’s okay if you’ve had to start over more than once. That’s kinda the whole point.

This is the important part that matters. Because I know how easy it is to believe you should already be “over it.” That you should have figured it out by now. That starting over once was understandable, but again? And again? REALLY? You want to say ‘enough already!’

But healing isn’t linear and growth isn’t either. And of course neither is grief. Or reinventing ourselves or becoming new versions of ourselves.

It’s a good thing that life gives us infinite chances to begin again—not because we’re failing, but because we’re learning in layers. In stages. Not all at once. But mistake after mistake. Stumble after stumble.

You are not broken because you’re still in process. Like one of my favourite Peloton yoga teachers says if you wobble or fall over in a pose - congrats, you’re human. And that’s a beautiful, complex thing to be. This is why we’re here. This is why we’re lucky enough to be living our lives. To experience things, no matter how long it takes to get to where we want to be or go.

A few gentle truths, if you’re starting again:

• You don’t need to have it all figured out to begin. Just start. Don’t worry about crossing all the t’s and dotting all the i’s.

• You are allowed to take your time (even if you might feel like you want to rush through it).

• Nothing is wrong with you if this feels harder than you expected (especially if it feels harder).

• You are not starting from scratch. You’re starting from experience.

• Rest is part of the reset. Rest is so, so, so important. Rest is where the transformation happens. Rest is where you strengthen (tangential side note: with exercise - the kind of workout that builds muscle - it’s not the actual workout where your muscles grow and get stronger, it’s during the rest periods, the recovery days. That’s why rest is so crucial).

• You don’t need a five-year plan (ick, no. I’m not a fan of the 5 year plan. Life is too whimsical and wild to have such a structured vision of the future, don’t you think?). All you need is a soft place to land right now.

What if starting over isn’t a setback, but instead a return?

A return to yourself, to your values, to who you really are. To the kind of life you’re allowed to live even if it’s smaller or quieter than you imagined (i’ll be writing about this in a future article), even if it looks nothing like what you thought it would. You’re allowed to begin again without apology. Not because you failed, but because you’re still becoming, still growing, still evolving (we all are). And that’s not a flaw, it’s a feature.

This starting over is a beginning. Not from scratch, as I said, but, you’re just rewinding the tape a little bit, so you can move forward again stronger and clearer. Maybe making a slightly different decision that will put you on a slightly different path. Choice by choice.

And you don’t need a map (or a 5 year plan). You just need a moment of self-trust. Then another. Then another. And again.

So…

This is my reminder to you that you're exactly where you need to be in your journey (even if it might not feel or look like it).

Like I’ve said before. Baby steps. It all comes down to Baby steps add up to big steps in the long run. And before you know it, you’re not starting over anymore. You’re already on your way.

If this letter found you at the right time, feel free to share it with someone else who might need a little wonder today.

✨ Love this reflection?
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With heartfelt thanks, always.
— Caitlin

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