How do you stay confident in the big decisions you make in life?

Like choosing between a well-paying job that’s comfortable but dull as f*ck, and a lower-paying one that is full of variety and opportunity. Or deciding whether to move overseas for a wild, uncertain adventure, or stay put in the safety of a steady life in a hometown. Even the smaller choices, like why I quit Kung Fu to play football instead. I could’ve used those Kung Fu skills by now.

These are the kinds of decisions I’ve wrestled with over the years. Sometimes, I look back and wonder if I made the right decisions. What if I’d chosen the other path? Would I be more successful? Happier? Maybe even have that dog I’ve always dreamed of? I overthink these things sometimes. Do people really make big decisions and never look back?

From,

Questioning my Decisions

Hi Questioning my Decisions,

Let me start by saying: I too, am questioning my decisions. Not in the way people do over coffee, turning their lives over lightly like a page. But the kind that curls me into a corner, pulls the dark in close, and has me shutting the world out.

As if shutting the world out were the same thing as shutting myself up.

I’m scared that this letter might not bring you as much comfort, as it honestly feels like writing to myself too. But okay, let me have a go; I’d hate for the lack of attempt to be yet another one of those decisions that nag me: what if?

On the Kung Fu. I felt that one specifically. My dad's musical career once handed me something I couldn't have dreamed up: a chance to perform alongside Lea Salonga, in Miss Saigon, in the Philippines. I had already said yes. Then I saw the stage. And I took it back. My parents were kind about it. The what if, however, has never quite left the room. These days, the room is practically full.

So here’s the thing about confidence in big decisions: I’m not sure it exists in the way we imagine it does. I don’t think people make big decisions and never look back, I certainly haven’t. Perhaps, we just look back less and with time, with a more forgiving lens. There’s a difference between reflection, reminiscing, and haunting after all.

There’s also this: the what ifs we torture ourselves with are rarely fair witnesses. When we imagine the road not taken, we tend to dress it generously: the Kung Fu skills, the overseas adventure, the entertainment career; while quietly stripping it of all the ways it could've also gone awry. I suspect, there are versions of us that took different paths that might very well have ended up sitting somewhere doing the same thing: wondering about this one.

Even a version of me that might not have been triggered enough to have started this newsletter. Or one where you don’t send me this letter at all. Suffice to say, I’d wager every version of us, in every timeline has to sit with regret and questioning at some point.

In my undergrad, one of my psych classes taught me something I've had to keep reminding myself of ever since: we tend to get regret backwards. Short term, we regret what we did: the risks, the wrong calls, the yes we shouldn't have given. But over time, those regrets tend to fade. What lingers are the things we didn't do.

So the what if crowding your room, and mine, isn't necessarily proof we chose wrong. It might just be the price of having chosen at all. And that? It brings me some comfort; we didn’t let life just happen to us, where possible, we actively made difficult choices.

It just so happens that in life, some of our decisions don't just carry weight: they fork. The path behind us closes, and those are the ones that often call back to our imagination. The well-paying-but-dull vs alive-but-uncertain fork is one I've stood at more than once. More than twice, honestly, if I'm being transparent about how many times I've romanticized stability and then suffocated inside it.

And I don't say that without acknowledging the privilege of even being in a position where I can afford to take the longer path; to pursue what actually interests me without fully compromising on survival. I can say that in many of them, it remains a privilege to have suffered in the ways that I have—in the ways that I do.

Eventually though, I've realized that dull doesn't announce itself. And I say that as someone who has welcomed it in, made it tea, and let it stay far longer than it should have. Because it was easier. Because I wanted reprieve from the version of me that had the audacity to want things; things that felt, on most days, like I was reaching for a life that wasn't quite meant for me.

paris circa 2022

Once upon a time, I chose humanities and social science over medicine, then business over creative writing, and then sat in a room in Singapore and decided I wasn’t willing to compromise my interests for a corporate career. Not long after, I was in a flat in Paris, opting out of a possible opportunity at L’Oréal that could easily have seen me two years in a city I loved, debt-free by the end of it. I opted for Brisbane on a full scholarship instead. Sure, it felt like the braver choice. It was. And it wasn’t. And then last year I chose London over a better-aligned job in Berlin, and somehow, after all of it, after all the choosing; I still find myself at a loss.

And then there's this: I chose humanities and social science over medicine, and yet somehow, for the last decade, financial reality has had me moonlighting in the ICU anyway. Life, it turns out, has a sense of humour. The path I didn't choose found me in sterile corridors at 2 am regardless; pinned down by a cost I bear rather than a passion I chose.

I'm still not sure what to make of that.

Maybe that's the thing about a loss you chose: it doesn't feel like losing until you're standing in the wreckage of the braver option, wondering if brave was just another word for naive. Punching above my weight, knowing it, and doing it anyways is exhausting. Sometimes you just want to put your arms down. And sometimes you do.

But uncertainty: the wild, inconvenient, occasionally humiliating kind, has a way of calling you back up. Having chosen it, stubbornly and repeatedly, I can tell you: it keeps asking something of you. So there is, I've decided, a particular dignity in being asked. Even when you're exhausted, or when you're not entirely sure you're up to it.

Having said that, I won’t dress the alive-but-uncertain path up as simply the braver choice. Some paths close doors. Others open ones you didn’t know existed. Neither comes with a receipt, and anyone who tells you otherwise hasn’t lived enough of it yet.

What I’ve learned to ask myself isn’t was this right, but was this mine— made with what I knew, what I wanted, who I was at the time. Judging it now is like holding a younger version of yourself to a map they didn't have yet. It's not justice.

Sounds more like distance masquerading as wisdom.

You made the decisions you made. So did I. And here we both are.

Still asking, still showing up. The rest is just negotiation.

I don't know if I'll feel differently about any of this in ten years. I hope so.

But also, not really.

After all, where would that leave me?

As for the dog; I've given it considerably far more thought than some of the life choices documented above, and my position is firm. Get the dog.

from the fork,

it’s michelle d.

p.s. there's a version of this letter I didn't publish; a companion post to this one. What I cut, what I circled around but didn't land on. It's up for paid subscribers later this week.

Hiii, in case you stumbled upon this serendipitously,

A quick intro:

I’m an intersectional human trying to figure out life, love, business, and help others a long the way. I write about the human stuff: the relationships we navigate, the decisions we second-guess, and the quiet confessions we keep to ourselves until someone asks the right question. Or rather, until someone gives us a safe space to voice out our questions.

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