What's your five-year plan?

I thought I had one, then life happened

Wanderer above the Sea of Fog by Caspar David Friedrich

Nearly two years ago to the day, I found myself in the backseat of a white van with two strange Chinese men…

Unfortunately, that’s about as interesting as the story gets.

I write this as I sit in a moving van, about to start the next journey in my life…
8-7-21 — 9:46 AM

There I was, my entire life in boxes, moving to NYC. The city of dreams, where I thought mine lay too. The backdrop where I’d start writing my adult chapter.

So if you told me then, that just two years later, I’d move my life into my parents’ basement in suburban Pennsylvania…

“There’s no way.”

The only believable part would be if you said I’d be writing from the kitchen — though more to myself than anyone else.

Two years is notable, not just because it’s more than one, but because it’s right around when I thought I’d be moving onto the next step in my plan — the path I was on:

• Two years in investment banking

• Two years in private equity

• Two years in an M7 MBA

Six years of my life — planned out before it even began.

Lived before it even began.

I can’t help but smile at how innocently naive I was. Can’t help but laugh at how that plan crashed and burned right after takeoff.

I just quit. I’ll have more to say and reflect on, but thought I’d note this moment — for who knows where it’ll lead to next.
2-27-22 — 3:29 PM

I made it six months out of six years. Goes to show how much I knew, which was really nothing at all.

As someone with a history of overplanning, I wonder why we care so much about having plans. Yes, there’s a level of prudence and practicality, but beyond that, what’s the point?

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Like many people, I was grasping at certainty before stepping into uncertainty. Preparing an answer for when I was inevitably asked questions like “What’s your five-year plan?” or “What’s next for you?” by some adult or overzealous peer.

Writing this just jogged a memory from summer orientation before my freshman year of college. Some kid in my group had the next four years of classes already planned out. I was shook — I didn’t even know what our school’s mascot was.

It seems like you start getting asked these questions around the end of high school, college — any major chapter. Before you even get a chance to let the ink dry and give your hand a break, you’re already expected to write the end of the next chapter. Staring down the barrel of a blank page with no idea what to write, some imaginary timer counting down — I’m brought back to those open-ended exams at school. The place where it really all began right?

From the moment you step foot in a classroom, you’re taught that certainty is more valuable than curiosity. You learn when you get called on to answer some question on a topic you could care less about. When you answer “I don’t know” and are met with giggles and snickers, “Not what we’re looking for”, and “Anyone else?”

Your peers teach you that being the kid with answers gets you more points and classroom clout than being the kid with questions. You learn when everyone else is trying to leave and “that kid just had to ask a question at the bell” — commence the chorus of groans and silent cursing.

Lo and behold, you get to college, and it’s the same thing all over again. Only this time, the open-ended question is:

“What are you going to do with your life?”

You have four years to answer, which seems like a long time, but really isn’t. Time just seems to speed up when you have a deadline. When the people around you already have their careers and lives mapped out — “figured out.”

It probably didn’t help that I was in a business fraternity.

Yeah, definitely didn’t.

No one wants to be the kid who doesn’t have a plan for what’s next. God forbid you are, then you’re lost, directionless, behind. And if you’re any bit the insecure kid I was, you know “behind” is not where you want to be.

So at some point, to avoid those uncomfortable conversations, you search for a path, an answer. Maybe you read one on an Internet forum or hear one at the career fair from a 24-year-old who somehow aged eight years in two. Either way, it doesn’t sound half bad, so you claim it as your own.

“I’m pursuing investment banking so I can be around a group of diverse and driven individuals — those are the environments where I’ve grown the most.”

Note: That was basically the answer I gave during interviews. If you’re familiar with finance, you’ll wonder how the hell I spit out “diverse.”

You repeat this answer so many times that you become certain it’s your own, that you must have thought of it one day in an “aha” moment.

Or maybe, you convince yourself that it’s your own. Falsely confident on the outside, truly insecure on the inside.

You think, no, hope no one will notice, but people can tell — they can feel it as much as you do.

So just like everyone else, you trudge forward on the path. You numb the feeling with late nights you don’t remember, more grind, or some AirPods. At some point, the path starts to reveal its integrity when what you once thought was paint is actually Sharpie, glue is actually gum.

Maybe you break down entirely, or maybe you take your AirPods out and let the world in instead of tuning it out. Either way, you’ve arrived at some point on the answer, but all you have is a question.

“Is this it?”

The question that started my adult chapter, and would also mark the end. Over the next three months, despite my efforts to seal the cracks, they kept appearing.

I’d live my answer:

“This can’t be it.”

My path was falling apart, and with it, my identity, my story.

I’d ask another question:

“What the fuck am I doing with my life?”

Safe to say, I had no answer. After all, no one’s asking you point blank “What the fuck are you doing with your life?” — so how was I supposed to prepare one?

But in that moment, some part of me woke up. Was finally seen, finally heard — finally answered:

“I don’t know.”

The childlike curiosity I had long repressed found its way through to me, asking:

“Well, what do you want to do with your life?”

And I suppose that’s how I ended up here. A 24-year-old, back in his parents’ house in the suburbs. One who left his day job and moved out of NYC — closed a chapter of his life. Not to “take a break from working” or “figure out what to do.”

Instead, I’m pursuing my answer to the question my inner child asked. An answer that I thought was an “aha” moment, but deep down, had known all along.

Being able to live and work remotely. To have the freedom and flexibility to live in and experience all the amazing cultures and beauty life has to offer.
7-11-20

When I read that journal entry back, I find it remarkable that deep down, each and every one of us knows what our dreams are — has a direction to follow. The only thing is, we’ve stopped asking the question:

“What are your dreams?”

We can’t stop asking this question, otherwise, we stop answering. If we do, we live our lives according to an outdated answer, written by an outdated version of ourselves. We project the present and discount the future — where our potential for change and transformation lies.

At the time, I thought “work” was destined to be some finance job I was indifferent towards at best. Now, I have no idea what “work” will be. It could be writing, YouTube, podcasting, or some combination of the three. Or maybe it could be something I can’t even imagine…yet.

As I’ve told people about this next chapter of mine, I’ve received questions like:

“Where are you going to travel to?”

“How long are you traveling for?”

“How will you make money?”

If I were to try and prepare an answer, I’d be coming up with a series of bullet points. Planning my life out before living it. Trying to write the ending to the chapter, without writing all the pages in between — where the story is really written.

So instead, I’m taking a pause to let the ink dry, to appreciate what I’ve written. And while I don’t have an idea of what I’ll write next, I think I’ll take a page from my younger self, and start with a question.

What’s to come? I’m honestly not sure. But I’m excited beyond measure to grow, develop, learn, understand. To live life — to laugh, cry, hurt, love.
8-7-21 — 9:46 AM

PS, the quote that inspired me:

“Be patient toward all that is unsolved in your heart and try to love the questions themselves, like locked rooms and like books that are now written in a very foreign tongue. Do not now seek the answers, which cannot be given you because you would not be able to live them. And the point is, to live everything. Live the questions now. Perhaps you will then gradually, without noticing it, live along some distant day into the answer.”
—Rainer Maria Rilke