On Quitting My Job

How deciding not to lead with fear opened the door to disrupting my life

On Quitting my Job

Quitting my job became one of the best gifts I had ever given to myself, even in the face of fear and uncertainty. It equipped me to open up doors for myself and forced me to focus on the trajectory I really wanted in life.

Quitting My First Job Out of College

I was 24 and working in my first job out of college. I, like most college graduates, had accepted the fact that I was not simply walking off the graduation stage and through the doors of my “dream job.” In fact, I didn’t even know what my dream job was or if it existed.

Despite the wakeup call, I considered myself pretty lucky. I had never expected to enter the marketing world, in fact, I was determined to avoid working for any corporation. I even went the extra mile to secure this fate with a degree in Creative Writing, an area of study I was certain had no place in the business world. It was a win-win for me, I studied my passion and set my eyes on a creative career path that most likely would involve publishing, editing, or working at an academic institution.

So, how did I end up working in marketing at a small tech company? Well, for one, I took the internship because I was four months away from graduation and realized I needed to find a job if I wanted to stay in California and continue living on my own. Second, I (shocker, I know), realized that working in business and marketing actually involved a lot of creativity. Third, I took one of the most powerful classes of my college career, an Entrepreneurship class I took for the hell of it. I ended up realizing that in all of my years of creative writing, I had been neglecting an equally-important side of me, the competitive, innovative, people-person that I was. Marketing, and more importantly, branding became a natural fit.

After the Honeymoon Phase

However, less than a year after I began working there, I was restless. I told myself I would work there until I decided that I was no longer learning or growing. I had reached a wall, but not of my own volition. Despite having an amazing boss who wanted me to learn as much as I could, there were some other issues at higher levels of the company that hamstrung our department. Tensions had been running high and I felt stuck. I dove into the job search without taking inventory on what I really wanted to do.

While I enjoyed marketing, I didn’t know if it was marketing itself or the qualities of marketing that I liked. I loved the collaboration, the feedback between content and design, the creative strategy, and taking big, often complicated ideas and condensing them into something relatable, emotional. Could I find that elsewhere? I didn’t pause to think, instead, I woke up 90 minutes earlier every morning and went to Philz Coffee to send endless job applications into cyberspace.

The Job Search

Needless to say, the process became quite demoralizing rather quickly. I had warmed up to corporate culture over the year, but the way the corporate ladder was structured bothered me. Just give me a chance, I thought as I networked with Apple employees and set my sights on some larger corporations. How do people even get in here in the first place? I was a USC grad, Summa Cum Laude, with tech marketing under my belt.

Yeah, I wasn’t expecting to land CMO any time soon but an interview somewhere, anywhere would’ve been nice. On one hand, I began to realize that the job application process was a long and disheartening process. On the other hand, I understood that my stagnation could have been a function of not knowing what I was really looking for. After several months of job searching, the possibility of quitting my job seemed farther and father away.

The Wakeup Call I Needed

I consulted two of my mentors. One, Greg, was my Entrepreneurship professor. Greg is a serial entrepreneur, a PhD, and one of the most intelligent people I’d ever met. I remember grabbing breakfast with him, excited about my job search. “I still have the energy and motivation at work, so I’m not in a huge hurry or anything.”

He seized the table. “Good!” he said, leaning over his egg-white omelet. “Don’t lose that! If you wake up more than three days in a row disliking what you are about to do, then you need to radically disrupt your life.”

Phew, I wasn’t there yet.

A month later, I was there. Fear and resentment had taken over. I was lost, and things at my company had grown worse. To make matters worse, I had recently read The Four Hour Workweek, which solidified my resentment of my current situation. I knew something else existed, but I didn’t know what.

I remember calling Greg and asking him “at what point do I just say screw it, I quit?”

He cautioned me against quitting my job with no direction. You don’t stumble on direction, accidentally, when you’re already lost. We got off the phone and I received a text from him:

“I can tell you’re torn between the risk of dynamism and the comfort of stasis. Step out, it will be ok.”

That was one of the most powerful texts I had ever received. He was absolutely right. I was clutching on to something, but I didn’t know what. I was also resisting something, but I didn’t know what.

Taking The Steps to Change My Life

The next few months changed my life.

I’m sure everybody in my life had grown tired of me complaining, yelling, or crying about my job and lack of luck with finding a new one. I had spent a small fortune on morning visits to Philz Coffee with nothing to show for it other than sampling their entire menu. I had networked my butt off, landed a couple of meetings at Paramount through my all-star business mentor. Still, nothing. I was heavily resisting the flow of life.

I am forever grateful to everyone who listened to me whine. Yet my boyfriend, Abhi, would usually offer the same suggestion. “What about freelance? You always seem interested in trying it.” or “Why don’t you monetize your blog?” or “Just put your services up on Fiverr and see what happens.”

The concept of freelancing was entirely foreign to me. I had spent the past four years competing with classmates in Creative Writing. I knew I was good but, like all things, there was always somebody better. Who would want to pay me for my writing? How could I commodify what I had learned in my short career?

Signing up for a freelance website soon became one of tasks that lingered on my to do list. I finally settled on two profiles: editing creative writing (which I loved) and brand development. I had assisted my company through rebranding and loved the idea of crafting a perfect elevator pitch and mission statement.

Two weeks later, I received my first order. My prices were obscenely low. $15 for a custom Vision Statement, Mission Statement, and Elevator Pitch. I feltpsyched about a first order, but felt skeptical about how it could ever be enough to pay the bills.

Getting Real

That weekend, I went to a conference in LA hosted by Mind Valley. A coworker, mentor, and friend of mine encouraged me to go with him. It was $800 for a ticket. Hard no, I thought, I might be jobless soon.

“Look,” he had said, “I really want you to go. I think you could really benefit from this experience. How about we split your ticket? Just give me $300 and we’ll call it a day.”

Ok, I thought, this is definitely a sign from the universe I cannot ignore.

I won’t dive into the details in this post but the conference was f’ing amazing. I was skeptical, thinking it would be culty or a sales pitch or something scientology-related. It wasn’t. In fact, it was quite the opposite. It was nearly 30 hours of empowerment, motivation, and introspection. We closed the ceremony with a meditation, where we had to picture ourselves and our purpose.

I pictured myself quitting my job and starting sobbing. I’m going to do it, I thought. And then, it hit me. My vision, my purpose. I’m a storyteller, I thought. I want to tell people’s stories. I want to tell the stories of people who can’t tell it themselves.

Later that afternoon, before the tears had even dried, I submitted my first ever Fiverr order. Boom. I made my first $12 (after commission). I cried, again. It was the most beautiful $12 I’d ever earned. And yes, while it may have been like 1/3 of my hourly rate at my job, it was a magnificent feeling. I earned it because somebody wanted to hire my expertise, my strategic thinking, and my writing.

Building Freelance Momentum

Six weeks later, the orders continued to pour in. Now, I have no idea how or why this happened. Fiverr is a pretty saturated platform. But I chose a simple task that I knew I was good at. Pretty soon I had repeat customers who were happy with the work I provided. Six weeks later, I landed my first client who payed me a retainer off of the Fiverr platform. I wasn’t making as much as I was at my 9-5, but still, I was getting closer each week.

At that time, I was essentially working two jobs. I woke up, worked on Freelance, went to work, worked on Freelance during my lunch break, went home, and went back to work. It wasn’t sustainable, but the momentum kept me going.

Unknowingly, I put something in place that gave me the courage to take that next step off the ledge. I had no idea where freelancing would lead, but I wanted to find out. I dreamed of being a business owner, and I was curious to find out what that could look like for me. There were still so many unknowns.

Like what if people stopped ordering my services?

And what if I don’t make enough?

What if I don’t get a job again?

All in all, what if quitting my job became a giant mistake?

Quitting My Job- The Day Of

I remember setting the official date to quit my job. I was going to do it. The main comfort going in was not the money and the potential of earning more, it was this and only this thought:

I might fail and realize that this was a terrible idea. And that’s ok.

I am a people pleaser at heart and my boss did not like conflict either. So needless to say I was SO NERVOUS when I went into her office on that Thursday. I hadn’t turned in my goals for the next quarter before our one on one, which was unlike me because I normally did that stuff first.

I had rehearsed my speech a million times with my mom and other friends.

My boss was awesome, so I wasn’t expecting to take her by surprise or upset her. But it went better than expected. She understood, completely. In fact, she told me how happy she was for me.

“So,” she asked, “what are you going to do?”

“I’m not sure yet,” I answered, honestly, “But right now I need to give myself the space to figure it out. I’m going to freelance to pay the bills until I do that.”

“I admire that,” she said.

My Last Day

On my last day, I received nothing but warmth and excitement from my team. Everybody asked me what I was going to do next. I answered honestly, and to my surprise, I did not receive skeptical expressions or any are you sure about that’s? I thought most people would scoff at the idea of me quitting my job.

Instead, I received a lot of wows, cools, and I wish I could do that. Now, don’t get me wrong, I was still tense and uncertain. But hearing people ten years ahead of me in their careers express envy was quite encouraging.

It is insane to think that six months later, I am significantly more per month than I made at my previous job. I am a business owner, and I am about to spend all of 2020 traveling the world with my adventure buddy.

I wouldn’t say certainty is something I experience every day, but I have direction, and most of all, I am so proud of myself. There are days that are scarier than others, lonelier than others, and more frustrating. But I have never regretted it, not even for a second.

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