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Quarter Life Questions

I quit the Navy’s Submarine Force.

I decided to leave on the last possible day any of us could leave: the day before we got our Dolphins, the badge of honor that proves we are officially qualified submariners.

It was a particularly difficult decision to make, not least because I was genuinely doing well in the job. Underwater warfare is quite different from surface naval warfare, and I was able to grasp the concepts relatively comfortably compared to my peers.

When I told my superior that I wanted to leave, he was, expectedly, surprised.

“You know that if you leave, you would be throwing away what would have been a pretty Illustrious career. Are you sure?”

(if you get the reference, good for you)


It felt good to say No, to tell him:

“Sir, I am NOT uncertain.”

(if you get this reference, we are going to be best friends)

Yet, a part of me questions whether my superior is indeed right — that I would be throwing away a good opportunity, a action-packed career in the ‘sharp edge of the Navy’, one that pays well, too. And one that I am actually good at.

I think about the Ikigai diagram, how your Ikigai is the intersection between 4 things:

  1. what you love

  2. what the world needs

  3. what you can get paid for

  4. what you are good at.

Staying with the Submariners would meet the latter 3 points (I’m not too sure whether the world really needs more military men training how to torpedo other ships and do stealth missions). Well, at least the other 2 points for sure.

But I don’t like the job.

I personally don’t enjoy it, nor find purpose or meaning in it.

I can rationalize why it would have meaning — the whole geo-political agenda behind having these assets, the strategic role we play in turning this iron coffin into a weapon of war, the pride that comes with being a part of this pseudo-elite force… the list goes on.

But that’s all it is. Just a list. Just a rationalization.

Ultimately, it isn’t internalized. It isn’t personal for me. And trust me, I’ve spent the better half of this year trying to internalize and truly believe this message of meaning, deep down.

Needless to say, it didn’t work.

While we were training, doing our drills, our commander would comment:

“Eugene, you meet our mission outcomes, you keep us safe, but you sound like your soul has left your body.”

Its been a running joke among my batchmates ever since.

Yet, it comes with a tinge of truth. Why do I sound soul-less? If anything, its the total opposite of the kind of comments that I would get when I am talking about Rats to Riches, or Crypto, or books. When I’m passionate about something, its super obvious. It emanates, oozes out, even. To sound soul-less means something is definitely off.


behind-the-scenes of a Rats to Riches feature video
definitely not soul-less here

I decided to leave precisely because it was so hard to decide.

Taking an ‘Essentialist’ approach, I saw it as either a ‘HELL YES’ or ‘No’ thing. By this principle, I have to love something at least 90% before taking it.

Anything less, reject it.

Submarining came pretty close to 90%. But I knew that if I stayed, I would be miserable there. I would not find meaning. I found not find peace.

Will I regret this decision? Only time will tell. 5, 10, 20 years into the future, when I look back on this chapter of my life, that’s when I would know.

Of the other paths I’ve walked on throughout these past 25 years, the pattern I’ve observed is that I walk on those paths too long, staying longer than I should have. The regret comes from opportunity cost — what my life could have looked like if only I had let go sooner, and tried other things.

There is a comfort, a certainty, in staying with the path you are already on. Clinging to the familiar. ‘The Devil you know’. The allure of the known, where the majority are, where things are stable and generally good. The temptation is real.

“Frightened of change? But what can exist without it? What’s closer to nature’s heart? Can you take a hot bath and leave the firewood as it was? Eat food without transforming it? Can any vital process take place without something being changed? Can’t you see — its just the same with you — and just as vital to nature.” Marcus Aurelius, Meditations


All my life, I've had the ‘mainstream path’ to fall back on.

I have been fortunate and blessed to have done well in the mainstream — whether that be scoring well in academic tests, or being able-bodied to have the chance to work onboard a submarine, with its stringent medical requirements.

I’ve also had the support of my family, friends and environment to nurture the traits that enable me to excel in this world.

A world of exams, credentials, 9–5 jobs, BTOs, CPFs and whatnot.

Even when I was pursuing my own side hustles, like making Creature Battle or Rats to Riches or investing in questionable stocks, I always had the safety net of the mainstream to catch me if I fell.

After all, I could just follow that path if all else fails.

Go with the flow.

Its easy to stay in the mainstream, letting the river flow, and you along with it.

Life is simple: there is only the next hoop to jump through, the next hurdle to cross.

Yet staying in the mainstream has always felt like a limited existence — I’ve always felt like I could be doing so much more, building truly amazing things and brainstorming the biggest ideas with the most interesting people.

The world is so much bigger than just submarines, or the Navy, or Singapore. And I still have 3 quarters of my life (hopefully) to explore it, play my role in it. A role that I, myself, create. So what if I’m doing well in the mainstream? I might be good at other things too!

And those things, I might actually genuinely love.

Once you leave the mainstream, nothing moves unless you do. Nothing flows unless you are in flow. No more pre-planned hurdles to jump over, you create your own hurdles. You decide how far you want to go, and you just go.

Today I took my first step out of the mainstream.

Out of the rat race.

Of course, there is still one more foot inside, just that now, I’m not moving with the stream anymore. Its just water flowing around me.

One good thing about stepping out of the stream is that I have the time to think about these things. To write about these things, as I’m doing now. To look at the past 25 years of my life, and set my intentions for the next 75+ (again, hopefully).

“The quality of your life is the quality of your questions.” Tony Robbins

I realize as I start looking back that I see the same situation in a very different way, when I ask a different question. So I fully agree with Tony’s quote, and have the following questions I intend to ask myself on a regular basis:

Where are you right now?

This probably seems like the most anti-climatic question, but read it again and see it from this angle: where are you in your mind space at this moment? Are you dwelling in the past, worrying about an uncertain future? are you consumed by anger, sadness or stress? Are you giving your full attention to what is right here in front of you?

Is this a ‘HELL YES’?

Do I love this at least 90%? If not, cut it out.

Is this an empowering or disempowering belief?

You could see this as a locus of control thing: empowering beliefs frame you as the protagonist, the person in control: “I am the master of my fate, I am the captain of my soul.” Its also about framing the situation as positive: if someone stood you up for a meeting, are you going to think that they had malicious intent, or that they really wanted to meet you, but something cropped up? Sometimes, even when thinking the latter option, we think: ‘Am I not important enough for them?!?’ Which is the ego talking and is low-key delusional.

So, TLDR: assume positive intent, and choose the belief that gives you the power to change the situation.

Or, let Dolores from Westworld say it better:

“Some people choose to see the ugliness in this world. The disarray. I choose to see the beauty. To believe there is an order to our days. A purpose. I know things will work out the way they’re meant to.” Dolores Abernathy, Westworld


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