Welcome to this week’s 1-2-1 newsletter. A small pause to reflect, reconnect, and pay attention to what matters.
Inside you’ll find one idea I’m sitting with, two voices I’m learning from, and one question or practice to carry into the week ahead.
**** SPOILER ALERT *** This essay discusses the endings of La La Land and Before Midnight. If you haven’t watched these films and intend to, consider yourself warned.
So I finally did it. Ten years later, I watched La La Land.
I’d somehow managed to avoid spoilers all this time. All I knew was that people loved it. The music, the cinematography, the performances. I’m glad I went in blind.
Because what struck me wasn’t the music or the visuals. It was the ending. Not because it was sad. Because it was honest.
As I sat there watching the final scenes unfold, I found myself waiting for the twist. The moment where everything comes together. The moment where the dream and the relationship somehow coexist. The moment where nobody has to sacrifice anything.
It never came.
And maybe that’s why it stayed with me.
A few years ago, I also discovered Richard Linklater’s Before trilogy. Three films shot over twenty years that follow the same couple through different stages of life.
What I love about both stories is that neither tries to cheat.
They don’t offer a happily-ever-after where every choice works out perfectly. They don’t pretend life can be optimized into a state where all the doors remain open.
Instead, they show something much closer to reality.
Every meaningful choice costs something.
The Option with no Downside
For most of my life, I believed there was a right answer waiting to be discovered. The right career. The right city. The right relationship. The right investment. The right decision would reveal itself because it would have all the upside and none of the downside.
The older I get, the more suspicious I become of the phrase “No Regrets.”
When did regret become a dirty word? Really? We either get life exactly right or we’ve somehow failed? I don’t buy it.
The poet David Whyte describes regret as “an elegy to lost possibilities.” I love that description because every meaningful choice creates a loss. You choose one partner and countless others disappear. You move to one city and leave another behind. You commit to one career and close the door on others.
Life narrows. Not because we’ve failed. Because we’ve chosen.
And if those possibilities mattered, shouldn’t there be some sadness in letting them go? Shouldn’t there be some grief?
What about when we tried something and it ultimately wasn’t the right path for us? Or when we learned something through an experience that led us to change direction? We put our blood, sweat, and tears into a dream. We build something. We become attached to a vision of the future. Then we move on.
Are we really expected to feel nothing?
In 2019, I purchased a massage therapy clinic. For a host of reasons, some of them to appease others and some of them to help me feel like I was making an adult decision. But I was also genuinely excited about it. It was fucking cool. I was a business owner. I had a commercial space. I had a business card with my name on it followed by the word “Owner.” It felt like my chance to build the kind of workplace I wished I’d had.
In 2024, I downsized that business. Today, it’s just me. No reception. No additional staff. I’m no longer a business owner. I’m self-employed.
And you know what?
That is working for me. It really is.
And it still hurts to think about how hard I fought for something that ultimately wasn’t meant to last.
I mourn the possibilities that could have come from that business. I do. That’s regret. But I don’t wish I still had it. I’m thriving in my current role. I found my place.
If I had gone directly from working for someone else to being self-employed, I think I would have spent years wondering what if.
Instead, I know.
I have a scar from that experience. It cost me something. But scars are not always signs of failure. Sometimes they’re evidence that something mattered. Evidence that we committed. Evidence that we cared enough to risk being disappointed.
Life will hurt.
It should.
That means you cared. That means you committed. That means you tried.
The goal isn’t to avoid regret. By our working definition of regret as lost possibilities, that would mean never committing to anything at all. Never choosing. Never closing a door.
That’s obviously not the answer.
We have to choose. We have to let go of possibilities. We have to accept that every path comes with tradeoffs.
And so regret is not the opposite of a life well lived. In many ways, it may be evidence of one.
There is courage in choosing a direction when you can’t know how the story ends. There is courage in committing to a person, a city, a career, or a dream knowing that other possibilities will be left behind.
Hopefully, at the end of a long and winding path, we can look back with compassion on all our pain and all our disappointments because they helped shape who we became.
I think the thing we would never wish upon anyone is not regret.
It’s reaching the end of life and looking out over the horizon thinking:
“I wish I’d gone over there.”
Neither path avoids pain. And to make it even more interesting, life often throws pain our way that we never chose. A layoff. A health crisis. An injury. The loss of someone we love.
Life narrows. Sometimes because we choose. Sometimes because circumstances choose for us
We choose people. We choose places. We choose careers. We choose dreams. And every choice leaves behind possibilities that might have been beautiful too.
That’s not a flaw in the system. That’s the system.
The goal isn’t to reach the end of life with no regrets. The goal is to look back with compassion on the roads you travelled, gratitude for the ones that shaped you, and the humility to accept that no life can contain everything.
Life narrows. Not because we’ve failed. Because we’ve chosen.
2 Voices I’m Learning From
1.
For a seed to achieve its greatest expression, it must come completely undone. The shell cracks, its insides come out and everything changes. To someone who doesn’t understand growth, it would look like complete destruction. — Cynthia Occelli
I’m sure there are times in all of our lives when we can relate to the sentiment of “complete destruction”. I think that being honest about those feelings is powerful. It wasn’t necessarily a mistake. It can be a moment of forging. Metal is melted and completely surrenders its shape before being forged anew. The middle part is surely terrifying, but the transformation cannot occur without it.
2.
Maturity is not a static arrived platform… but the dissolution of living elemental frontiers between what has happened, what is happening now, and the consequences of our past… Maturity is the time when these tidal forces meet and break apart our life, making one life out of our regrets, our self-compassion, and our forgiveness forged into a future made real by a radical change in our behaviour - David Whyte
Maturity is an ongoing process. That's what I love about this passage. Taking everything that has happened to us and allowing it to shape and inform our future. That's beautiful. It's elegant, and it's honest.
1 REFLECTION / ACTION
Think about a regret you carry.
Now ask yourself:
Do I regret the choice?
Or do I regret the possibilities that disappeared when I made it?
There is a difference.
Spend ten minutes writing about what that decision gave you, not just what it cost you.
Perhaps maturity isn’t reaching a place where regret disappears.
Perhaps it’s learning to hold regret, gratitude, self-compassion, and forgiveness in the same hand.
To honour the roads we travelled.
To mourn the ones we didn’t.
And still be willing to begin again.
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