San Francisco, CA

Quitting My Job to Start My Own Thing

Dessy John

Wow, this is actually kinda scary
set freeMohamed Nohassi/Unsplash


I did it. I quit my high paying tech job. I had a going away happy hour, filled with lovely people emitting the full spectrum of possible reactions to the life changing choice I made. Some were wildly jealous because they were looking for an exit themselves, but couldn’t bring themselves to pulling the trigger. Some showed empathy (or pity — it was hard to tell at times), offering their help should any networking or reference opportunities come along. But oddly enough everyone, and I mean everyone, understood WHY I was doing what I was doing. I expected some “why would you do that?” or “what about your children?” to come my way. But I learned something interesting…just about everyone on some level WANTS to be a little scared, provided the fear comes from their own pursuits and not someone else’s.

People don’t want to be in the rat race forever. They are simply conditioned to believing it is the only option. They get sucked into the consumerist epidemic so deeply rooted in the tech industry, thinking they need more and more just to remain comfortable. They then get trapped into corporate shackles being the ONLY option in sustaining their lifestyle with minimal risk — except of course for the somehow acceptable risk of remaining in those shackles for the rest of their lives.

Finding Peace

On my first official day as a free agent, I had no big plans. I wanted nothing more than to simply feel free and in control. I bought groceries, which was a shockingly therapeutic and cathartic experience because my “tech self” had been using Instacart for years. Physically being in a grocery store, albeit an uncrowded one on a Monday afternoon, reminded me of a simpler time in my life feeling connected to what I was doing and having a sense of choice without feeling crippling decision fatigue. How could something so seemingly menial and unfulfilling in nature feel so grounding and satisfying? The answer, I suspect, is inextricably linked to gratitude, humility, and simplicity. Being thankful for the little things and not feeling as though they are “beneath you” is something that came easier to us as children. Eventually this gets beaten out of most of us over the years and years of going through the grind and “surviving” life.

Distilling the idea of virtue in simplicity there is a parable, often referenced in self-improvement and personal finance blogs, of the monk and the minister. It reads as follows:

  • Two close boyhood friends grow up and go their separate ways. One becomes a humble monk, the other a rich and powerful minister to the king.
  • Years later they meet up again.
  • As they catch up, the minister (in his fine robes) takes pity on the thin, shabby monk. Seeking to help, he says: “You know, if you could learn to cater to the king you wouldn’t have to live on rice and beans.”
  • To which the monk replies: “If you could learn to live on rice and beans you wouldn’t have to cater to the king!”

Separation from my 9–5 (or more accurately my 8am to 10pm) has quickly reset my mindset further from the minister and closer to the monk. I spent the first 10 years of my post-college life singularly focused on increasing my income in hopes of a bigger and better life. It took me nearly the entirety of those 10 years to discover that while this pursuit built resilience and character, but ultimately was misguided as a destination.

My career has afforded me a nice life financially and now enables a choice between a more independent lifestyle or a return to corporate life with a completely renewed energy and perspective. I am not, by any means, swearing off corporate life at all costs. I could always go back, and I respect the security and camaraderie it provides. But if I do go back, I’ve learned in literally one day off the books that it only makes sense to go back with authenticity, candor, and the audacity to own the hours in my day.


I’m not going to lie, making a move to separate from all that has been familiar to me is difficult and scary. Right off the bat, I felt a pretty gripping and primitive need for psychological wins that validated my decision.

My daughter began a transition preschool/daycare this week, which is basically a daycare for toddlers where they “graduate” into preschool by age 3. That’s the only level of detail I’ll provide on that because I’m sure you are either already familiar with it or don’t care whatsoever. I had been considering leaving my job for some time but I specifically chose this week to do so. The first reason was that the school was a cost saving relative to the nanny we were working with prior, so I could better deal with the income loss. The second and more important reason was that I wanted to be present and available as a parent. The alternative would have been to coldly drop my daughter off at a new and unfamiliar place while frantically getting the hell out of there to catch a train across the bay into San Francisco to show up probably a few minutes late and unprepared to a morning meeting. Every single day. Taking the time to establish myself as a source of comfort and protection for my 2 year old daughter far outweighed the job security. Purpose trumps money every time.

Gaining Steam

So what now? I’ve never actually done this before. I’ve never monetized my writing. I’ve never built a personal brand from scratch to become self-sustaining. The way I see it, the story is what matters. Optimizing my life to give myself choices is something that resonates with nearly everyone I discuss it with. Old folks, young folks, parents, bachelors — some version of this story clicks for all of them. If I can get that part right in a way that captures your attention, I have time to figure out the operations, marketing, and revenue streams behind the work. My whole career has been spent on marketing and growth for businesses — and in this case, simply put, the business is me.

Most importantly, my writing is a waste of time if I’m the sole hero of the story. I know if you’ve stumbled upon this article, you’ve either thought of making a similar move in your life or have already done so and are looking for like-minded guides to relate to. My value is only tied to the extent in which I can offer you a fresh perspective, so I want to hear from you and understand how I can help.

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I am a personal finance writer, covering advice and strategy around building wealth and living a more abundant life. I have 13 years of marketing experience in the tech industry, have built my own wealth, and now aim to do my part in spreading financial literacy to help others.

San Francisco, CA

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