the wanderer

when the fear of failure isn't abstract anymore

Sometimes I’m too scared to go after my dreams.

I was homeless once. The fear I’ll loose my job and my stability eats me. I don’t know what to do next. Go back to school, keep applying for work, even though my job is a dead end. What should I do?

I feel lost,

the wanderer

---

Hi The Wanderer,

The wanderer.

Hmm. Not a name someone gave you. A name that you gave yourself, at the bottom of a letter that opens with I was homeless once. A word that makes instability sound like it was a choice.

Now, I’m not calling it out from a place of criticism. It’s the most interesting part of your letter. Calling yourself a wanderer before anyone else can call you lost? Quite a particular kind of self-preservation that is. The kind of move someone makes when they’ve learned that the world will name you if you don’t name yourself first.

But I’m curious: does the name still fit? Or has it become a means to make peace with something you haven’t fully made peace with yet?

For the question you’re actually asking: school or work. I’m not going to answer it. It’s asking the wrong thing of the situation you’re actually in. And I suspect, somewhere underneath the asking, you know that too.

The thing you’re describing isn’t indecision. It's someone who has been on the floor and still walks into every room knowing exactly where it is. The real floor: cold coming up through it, shoulder and hip taking the weight of a body with nowhere else to be. A surface not designed to hold a sleeping person. That fear is not the same as the fear of someone who has only ever imagined it. Those are different problems entirely.

Most people who feel professionally stuck are afraid of something abstract: the wrong choice, wasted time, a version of their life that didn’t happen the way they’d imagined. A real fear worth taking seriously. But yours has a different shape. Your intimate familiarity with the floor means the calculus isn’t might fail — it’s will fall back there. Even when the decision in front of you no longer carries that cost. Even when the math doesn’t support it.

It’s survival logic. It doesn’t stay contained to the circumstances that made it. It moves with you. Gets into how you read a job listing, how you weigh a dead-end salary against school fees, how you find yourself unable to trust your own judgement about what’s worth reaching for. Because something registered in your past, that hasn’t fully unregistered.

School or work is a logistics question. The one underneath it is harder: how do you learn to trust your own instincts again, after they spent so long calibrated entirely toward not losing the floor?

I don’t have an answer to that. Not a clean one for sure.

I’ve always loved the heavy rain. Not the sad, trickly kind. The kind that pours so hard it drowns the world out, that comes down like it has something to prove.

As a child, I lived in houses that rain fell through. When I go home-home, I still walk into houses like that. Corrugated iron roofs: when the heavy kind comes, it stops being sound and becomes a wall of it. Something you can’t think past. The floor floods. You learn which shelf is high enough. You stop putting the things you love near the ground without realising you’ve decided that.

I still love it. It still brings me a comfort that’s hard to name or truly divine, the obliteration of everything else, just rain, just this, just now.

But that kind of rain is flooding somewhere. A family lifting their appliances off the ground, brown water rising past the threshold. A child held above the waterline, feet in the air. The smell of it, not rain smell. Drain smell. The street coming inside.

Someone is having the worst night of their life because of the weather I’m calling beautiful. It rains like that in Singapore. The city was built to take it. I used to sit on the balcony to watch it. On my tougher days, I’d go down to the pool and swim amidst that downpour — in clean, chlorinated water, a pool inside a condominium, behind a gated property.

I’ve been on both sides of it: the side where the rain is beautiful, and the side where it comes through the roof. The love and the fear don’t separate. They arrive in the same sky. And I hate it. But without it, I'd only ever be the woman in the pool.

I'm not sure I'd want to just be that woman either.

I don’t think you stop being the wanderer.

I think the word slowly changes what it means.

still figuring out what the rain means,

it’s michelle d.

---

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.

One thing I learned from writing essays is how much I love the interaction and community around it. Hence the core concept of this newsletter: unsent letters.

Send me a Letter

Send me a quiet confession. Dilemmas that keep you awake, unspoken feelings, the truths that live only in your head. I don’t advise severely; I’m not qualified for that. But I can read, reflect, and remind you (& me) — it’s not just you. It’s us.

Unsent letters: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20

Personal rambles: 1, 2, 3, 4, 5, 6, 7

Behind-the-letter: 1

---

Join me in building the kind of community that reminds us someone out there understands. Everything here is free to read. Paid subscribers get a behind-the-letter post for certain pieces: the cuts, the detours, what I almost wrote instead. If the writing means something to you, that’s one way to stay closer to it. Or buy me a coffee. Both appreciated.

Never miss an unsent letter.