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Millan Singh

A graveyard of self-belief and the "Entrepreneur's Bridge"

Published 10 months ago • 7 min read

A Hero's Journey

Wednesday, April 24, 2024


Hey there Reader,

Not going to lie, I feel guilty. And I don't like it.

First of all, to the new subscribers who came from Sam Gabrail, welcome! This issue will start on a little bit of a downbeat, but there's some good reflective stuff in here, I promise. So stick with me for two minutes, and I promise it'll be worth it. Also, there's a sneak-peak at a SaaS app I'm working on at the bottom of the issue.

I feel guilty, because I said—nay, I committed—to writing another issue by May 25th and that I would publish a story about working at a startup that would spawn a series by that same date. Well, I'm about a month late on the newsletter issue, though I did publish that story, at least.

4 Signs You Should Work at a Startup as an Engineer

The good news is that I'm really proud of the story I wrote, and I actually wrote it fairly quickly. Publishing, on the other hand, was a disaster. However, I'm going to save the rest of that story for the next issue of A Hero's Journey.

Let's get to the meat of this issue...

What Does It Mean to Believe in Oneself?

I've been imagining my future a lot lately. Through a combination of extended travel (I'm in NYC looking for apartments after having just returned from a vacation in Tel Aviv), browsing the expensive NYC real estate, and a breakup, I'm in this mode of wanting—or rather needing—to build towards the next chapter of my journey.

And that need has led me to ruminate on several curious observations about my own belief (or lack thereof) in myself. In fact, I've realized that the next major shift in my life needs to be a shift in my self-belief.

A Strong, But Vague, Belief in the Future

For as long as I can remember, I've felt that I'm (for lack of a better term) destined to live a certain kind of wonderful, impactful life. That my life should be full of achievements, legacy-builders (things that will live well beyond me), and the love and support of the people closest to me. That I will be wealthy, with ample resources to fund causes/businesses I believe in, invest in my community, and enjoy one or two of the finer things in life along the way.

But that belief is in "Future Me". "Present Me" doesn't get the same faith.

Somehow, at the same time, I can believe, in my deepest core, that this is the life I will live, and yet still feel that I have no idea how to even approach building that life (or wonder if "Present Me" is even worthy of it).

But if my belief in "Future Me" is assumed to be accurate, that means that there must be some version of "Present Me" that eventually becomes "Future Me", and, therefore, is worthy of that same faith that "Future Me" enjoys today.

This paradox is where I begin the next chapter of my journey.

A Graveyard of Self Doubt

I've always been ambitious and have cycled through many iterations of that ambition: projects, businesses, etc. But most of these have perished (or never really gotten off the ground) due to this self-doubt.

To be clear, many of these perished dreams were just bad ideas: for all the good ideas I've attempted, I've attempted at least an equal number of bad ideas. And, by the way, accepting that not every idea you have is necessarily good or worthy of following through to some "end" has been one of the better lessons I've learned in life. Pivoting or letting go of something is okay sometimes, and you don't always need to feel guilty about "quitting".

But many of those dreams were good ideas (or at least decent ideas), killed by self-doubt, either "doubt that I can do it" or "doubt that I can convince some "other" of the value of what I do."

I've made a lot of progress in abating the "doubt that I can do it" one. These days, I actually have confidence that I can do whatever I set my mind to, given appropriate support/resources. It's not perfect, but this isn't holding me back much anymore.

So this next chapter of my journey is going to be about addressing this other doubt that, essentially, no one will care even if I do something good/valuable/etc. And I think the core challenge is actually shifting this doubt from an external locus of control to an internal one.

The antidote to self-doubt is faith in oneself.

It became clear to me, actually, as I was writing this very issue, that the problem I was dealing with was an external locus of control. This means that my doubt is fueled by the uncertainty of others/the market/etc. And of course it would be: those things are pretty unpredictable.

My therapist recently imparted a simple piece of wisdom that he heard from a Rabbi: the antidote to self-doubt is faith in oneself. And this makes total sense. Instead of worrying about what others think of you and what you do, if you have faith that you and what you do are worthy, at some fundamental level, it won't matter what others say, because you know you'll eventually find the ones who "get it" and won't get discouraged by the ones who don't.

Easier said than done, of course, but that's the challenge I'm setting forth to conquer.

Crossing Over

Let's make this more concrete. In this next chapter of my journey, I'm going to need to cross one very important psychological "bridge": I need to be able to offer a product (or service) to the market and have that product be purchased by other people.

Sounds simple, right?

If my intuition about what my life is supposed to end up being like is correct, I will inevitably cross this "Entrepreneur's Bridge", as I call it. This is where I go from just being an employee, trading my time and expertise for a steady paycheck, to an entrepreneur, selling a product to the market.

Of course, it's not binary. Crossing this bridge is not the same as becoming a full-time entrepreneur. This is merely the first step in that process—the first sale, or maybe the first ~five sales (one can be a fluke)—and I'm not planning on leaving the workforce any time soon.

Much has been written about these concepts—and I don't think anything I'm saying here is terribly original—but I've realized this is the current bottleneck in actualizing the life I want to live.

I need some faith in myself.

Crossing this bridge will also no doubt entail a lot of learning and personal growth, as it will push me to confront a lot of things that are naturally somewhat uncomfortable for me (like sales). But in the end, it will be worth it, and it's necessary for the life I want to live.

Of course, I will keep you guys updated on my progress in crossing the "Entrepreneur's Bridge" through this newsletter.

Journey Update

As I mentioned earlier, I've been traveling a lot lately, so I've gotten a chance to take a much-needed break. But now I'm back and getting at it. In fact, in the final few days of my vacation in Tel Aviv, I was ready to get back to the States and get to work.

Many of you know already that I'm in the process of moving to NYC, so I'm here for a while looking for an apartment too, and this has already been the longest I've ever been away from home (a little short of a month already!!), with almost another month left before I head back.

But the biggest news is that, after a little break because of other life factors and a busy day job, I've picked up steam on PushBrand again. I mentioned this in the last issue, but it's a SaaS product I've been working on (frankly, for way too long haha) that's getting close to being ready for launch. Here's a little sneak preview:

I don't have an exact launch date yet, but I'm hoping to get this ready to launch in a month or so. We'll see if I can keep up my pace while getting back into the swing of my day job and other life responsibilities, but I plan on including a screenshot of the app in each newsletter issue up till launch, so expect more sneak peeks.

I'm really happy with how it's shaping up, and I'm excited by the possibility of people actually using it (other than me haha)!

That's all for this week's issue. Thanks for reading, and you'll see me in your inbox again next week!


If I can ask you to do just one thing, consider sharing this newsletter with a friend or family member. Here's the link so you can pass it along: https://aherosjourney.co/.

113 Cherry St #92768, Seattle, WA 98104-2205
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Millan Singh

I'm writing about my journey to build, learn, and grow as a Creative Entrepreneur and Software Engineer. Stories about my job (I'm employee #2 at a seed-stage startup), entrepreneurial work, investing (a personal passion), and personal growth—a blend of professional and personal content.

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