The Leap

Leaving my day job to pursue something more meaningful

I. Journey

I quit my job to pursue a dream.

For years, that dream was hazy, but I had inner certainty that I needed to leave corporate life and pursue self-employment. So I followed my curiosity, cultivated my interests, and the path became clearer.

Why did I leap in the first place?

Was it the nagging sense of dissatisfaction? The lack of meaning? The persistent feeling that I could do something more worthwhile?

Getting to this point was ultimately the result of many minor but increasingly larger leaps toward positive transformation. It felt like I was being led somewhere. Being called. Unable to see the destination but having faith in the subtle signals that brought positive outcomes.

It started in my late teens when I committed to the path of self-improvement. First, it was the simple stuff. Exercise. Discipline. Hard work. Then it got tougher—more psychological.

To break free from the unhealthy habits that anchored me to the day job, I needed a catalyst, and I found one.

Love sparked the journey. From there, I began to care for my authentic self, moving on from unhealthy influences that held me in outdated behavior patterns. I added journaling and dream interpretation to my daily routine (strongly influenced by Jung). I kept working to conquer the next challenge. Consistently doing so allowed me to tackle more complex problems and face more challenging crossroads.

Each path always held a distinct character: one of comfort and ease; the other of struggle and transcendent promise. One crossroads, though, always brought fear and doubt. It kept me moving, not forward, but in a circle.

II. Crossroads of Indecision

I couldn't make myself fit into the corporate '9-5' structure. 18-year-old Dom saw dollar signs and followed. It didn't take me long to realize that money should not be the superordinate aim. However, it did provide survival, which made moving against its tide challenging. I knew that there was something larger for me, and I decided to find it, regardless of the sacrifice required.

About five years ago, I diligently started to hone my interests and find what that thing could be. Through that time, I was preparing myself—mentally and practically—for a corporate exit. But whenever I was faced with the decision, I couldn't bring myself to make the jump.

I was stuck in a loop.

I felt miserable -> Planned to leave -> Got ready -> Things got better -> I justified staying -> I wouldn't leave -> I felt miserable.

"I can stay and pursue the dream in my free time!" I would say to myself.

But when I logged in for another 7:30 a.m. meeting with heavy eyes, I’d glance at my personal computer and feel a tug toward it. The day continued and the ache returned. It was like the computer was telling me that I had more important business to take care of, and that I was feeding the wrong part of me. By the end of the day, I fell back into the loop; not committing to the person I wanted to become, but rather the person that I felt trapped as.

I knew I needed a different path.

Part of being unable to jump was feeling uncertain about what I was going after on the other side. My interests would drift, but one path never really left. So, when I was faced with the crossroads again—wiser and better prepared—I finally took the leap of faith.

III. The Leap

After my wedding, I had a strong intuition to write a novel. I came across Brandon Sanderson on The Tim Ferriss Show, studied Brandon Sanderson's writing lectures, and put my ideas into practice.

I'm nearly finished with my rough draft (~170k words) of my first science-fiction novel. I'm loving the craft of storytelling—so much so that I decided to leap and write full-time to see where it takes me.

When people ask me what I'm doing, the easiest thing to say is I'm trying to become a professional writer. Or trying to become an author. Though it's not as simple as that. Yes, I'm going to write, and I'm going to try to make a living doing so.

However, trading one persona-image (corporate man/accountant/risk manager) for another (writer/author/storyteller) is what I want to avoid.

Sometimes, life's journey can change unexpectedly when you follow your interests and intuition. As Steve Jobs said, the only way following your interests will make sense is by connecting the dots backward. It may be the case that writing leads me to something even bigger. One novel leads to a hundred! Maybe after the first novel, I find I'm more interested in writing TV scripts. Maybe I focus on writing essays.

The point is—I don't know where it will take me, but I have learned to trust the source of these signals and apply discipline to do what it asks of me. Now, I'm making an investment in it and buying myself more time to write stories! All that said—and to give the persona form—I’m striving to be a professional writer, author, and creator.

I must say, as with all transformation, the path has been necessarily difficult.

Often, conversations about work are painful. I find that people with a predefined notion of who I am don't like me out of that defined box. The most painful is when people try to shove me back into that box.

The harder problem I've faced is internal. The creeping whispers of fear and doubt. "Will this prove the dumbest thing you've done? Are you sure you can do it?"

This isn't a reason not to do it, though; in fact, it's a reason to do it.

If achieving my highest potential involves this path, I must walk it. I view these difficulties as necessary challenges to test whether I’m ready.

Ultimately, there are a million reasons not to make the decision, but there is only one reason I need to make the decision, and that's that it points to the truth. I feel called to this challenge, and when faced with a feeling such as this, it would be foolish not to give it a try.

A question I've asked myself that I find immensely helpful when faced with these challenges is: Will this be the thing that stops you from pursuing your dream?

The answer must be no.

I would guess that the biggest blocker—it certainly was mine for a long time—is money.

As Tom Morgan puts it, "The tension between the pursuit of meaning and paying the mortgage is legitimately humanity's main quest right now."

I wish there were an easy answer to the money question. For me, it took years of saving/investing to get to a point where I could risk it to invest in myself, giving myself the chance to build a steady income from writing. I will find out soon enough how it works out for me, and I hope I can report back with good news.

Now, I don't advocate taking a leap lightly. I have been planning for years. However, I realized that once the practical concerns are accounted for, the best plan is, paradoxically, faith¹.

I must admit that there is one force that has helped tremendously.

The force that I think I'd have a hard time leaping without…

IV. Love – The Catalyst of Transformation

All of this would have been impossible without my wife, Shannon.

The day I met her felt like the beginning of the main story of my life. Like the years until then were the game's tutorial, and meeting her was the catalyst that set me off on the main quest.

As I followed that path, the challenges—both inner and outer—became tougher. With Shannon supporting me, those challenges became easier to face. It also meant that failure was more consequential, increasing the stakes and making the path far more interesting.

She sees the best parts of me and pushes me to be all of them. Jumping toward something uncertain and without stability is difficult, especially when others rely on me. Having someone who both relies on me and pushes me toward my biggest aspirations feels miraculous.

I recently looked through my annotations on Stephen King's memoir, On Writing. I saw her name written next to a quote I underlined, which emphasized how important a loving influence is. It gives me hope that this experience is more universal than I might think:

My copy of On Writing

I hope everyone has that one person that they can openly speak with about what they really want with their lives, and that person will respond with, "Okay, how can we make it happen?"

Here’s how I’m answering that question.

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I have committed full-time to writing stories, and like the Frontier Letter, it feels like a fundamental part of the journey.

The Frontier Letter will serve a core pillar to how I formulate my thoughts on interesting ideas at the frontier of our culture. This will serve as a great source for aspects of my stories (so if you like the topics I think through here, you’re more likely to enjoy my novels). Interestingly, my previous essays served as worldbuilding and thematic aspects of my novel-in-progress (the dots connected).

I will also experiment with a solo podcast on YouTube to think through any ideas occupying my mind in a looser, more unscripted way.

My writing will continue to unfold here, so if you’re new, subscribe if it resonates.

I am forever grateful to be in this position, and I hope that one day everyone can take their leap, whatever that looks like for them.

Though I will certainly stumble along the way, I'm excited to see how far I can take this.

Let's see what happens.

Take care, everyone.

Dom

1. Matthew 6:25-34 – Though I don’t think this should be used as a means to make a reckless leap, it’s helpful to see a piece of eternal wisdom provide a sense of reassurance.