My Great Resignation Story

February 5, 2022

job quit

No one just becomes an entrepreneur for the heck of it. Just like no one decides to stay employed by somebody else, just for the heck of it. There are all kinds of reasons behind the decisions people make about their livelihood and how they’re going to make a living. Usually these reasons intersect with long-held beliefs, societal conditioning, some imagined or self-imposed set of rules, or the fears and what-ifs that accompany the thought of the status quo ceasing to exist.

My story is no different. If you read the About Me page, you can follow along with my journey and all its twists and turns through different professional landscapes, creative endeavors, mistrials, restarts, and forks in the road. That’ll lead you right up to the ledge I jumped off of, but it won’t take you along for the plunge. Diving off the deep end with me requires a little more commitment than that.

See, nearly every website has an About page. Just about anyone who’s trying to promote something on their website will have a page explaining their service or their story to their audience. That’s standard, casual fare – an appetizer, something you could just happen upon while browsing around. It’s skimmable, it’s optional, it’s not usually a prerequisite for getting involved with the site owner or their content.

But a blog post, a more long-form story like this one, is something you chose to click on. You navigated your way here to have a look, even though the blog is something separate from the informational pages on my site that explain my services and my methods. That’s why I’m writing this story here, away from the common area’s quick perusals and surface-level nods. If you’ve found this page, you’ve explored a bit and, if you’re still reading, you’ve committed a certain amount of time and interest to learning this part of my story. So here goes.

United in Rarity

Many entrepreneurs are considered black sheep. They’re not typically the ones who fit easily and neatly into a mold handed down to them by family, society, or an employer. Maybe they’re the noise-makers and rule breakers of their peer group or family unit. You can bet that anyone who’s an entrepreneur felt unfulfilled by some aspect of traditional employment (or the idea of it, in the case of lifetime entrepreneurs who may have inherited their roles). Aside from grit and determination, this atypical nature is probably the single most unifying factor among entrepreneurs.

I am no different. I took jobs to make money because that’s just what you were supposed to do. As a teen, I would babysit, work at restaurants, and take retail jobs to make some spending money. Fine, normal. As a college student, I worked on campus to pay for some of my room and board fees. But after college, there was this unsettling feeling of “now what?”

I’d say my destiny as an entrepreneur could’ve been foreshadowed as early as childhood (because hindsight is 20/20 and I was always into weird things and big ideas). But I didn’t start having conscious inklings that I wasn’t cut out for the traditional route until college.

I was pursuing a degree in performing arts (vocal performance) — I wanted to be an opera singer. Two years and roughly $80,000 in student loans later, near the end of my sophomore year, the realization that a degree doesn’t guarantee a job in said field hit me like a punch to the gut.

I felt mad. Scared. Like I’d been asleep. Like the rug had been yanked from under my feet. In all my gusto (and my family’s best intentions), I’d gone head-first into my undergrad, playing “I’m going to be an opera singer,” without giving much thought to what that actually looks like once the precursory 4-year training was complete. If a degree in vocal performance doesn’t land you a role at the Met, I thought, then why am I paying so much for it? Pavarotti didn’t need a degree. Many famous singers probably didn’t have a degree in music (or any subject) when they got their start. There I was, getting my first lesson in the “right place, right time,” category, pondering the “it’s all about who you know” factor, and asking myself, “Do I really have what it takes? And even if I believe that I do, do I really want it badly enough to move to New York, go on countless auditions, and live like a starving artist working menial jobs so that I can take crappy gigs at night until I get booked for better and better ones that eventually might pay my bills?”

Just the thought exhausted me. I shut the door to the practice room and returned to my dorm with the echo of other vocalists’ arpeggios chasing me down the hall.

Identity Crisis

There was no looking back. Once you realize something like that, what’s the point of moving forward? I’d decided I didn’t want to try and hack it in the real world as a performer because singing was just a talent that I wanted to keep as a hobby. It was fun when there wasn’t any pressure tied to it and people would clap and say you’re good. A concert here, a recital there. But once it started to look like a behemoth force threatening to put a ball and chain around my ankle, I just couldn’t stare it in the face anymore.

Then came the horrifying “what else am I good at?” monologue. “What else can I possibly do?” How would I pivot, two-years and $80,000 unto my undergrad into something more promising, more practical, and more career-oriented? I didn’t know it yet, but I was heavily indoctrinated by the guise of ‘safety,’ whatever that meant, and definitely didn’t realize that I was my own greatest asset — that took another decade, at least. I digress…

The only other talent I thought I might be able to use to make a living was my love of language. I was already a gifted linguist, simultaneously studying four languages as a musician and having already had an extensive education (both in and outside of school) since middle school. Surely, if I just transferred to another 4-year university to study languages of my choosing, I could use the degree for anything I wanted — teaching, translating, becoming a clandestine service operative for the CIA, right?

It sounded good to me. I put the plan in motion and eventually ended up a French major and Italian minor at another private, out-of-state institution (queue another $80,000).

You Graduated! Now What?

The future looked bright. Armed with my stellar academic record and my much more practical choices, I completed an accelerated course load, led some student activities, performed a little, spoke a little poetry in other languages, wrote a million-page thesis entirely in French, wowed my leaders, and graduated with honors. So…why didn’t the next step seem clear? Should I…teach? Uh, ok, sure — I was no education major, though. I received ample guidance on how to pursue alternate route certification, take a Praxis exam, and get all set up to become a teacher. I came oh-so-close to doing it – I even did my student teaching at a great school, thanks to my dean calling in some favors – but something was off. Did I really have the experience to discipline a classroom full of kids? Would they respect me? What if I got a job teaching high school and they saw me as a peer instead of an elder? I’d been hearing from teacher friends how hard the industry was becoming…was it really for me?

I was still unsure. Which pissed me off. (I’m a very “sure” person. Ask anyone who knows me). To be this unsure about my life path was unsettling.

I was offered an entry-level corporate job, a desk job, at a financial institution. I was in immediate need of income and I had to do something. “It’s got nothing to do with my degree or my skillset,” I thought, “but that doesn’t mean I can’t spend time searching for the perfect job and filling out applications in my free time.”

So, after a month-long road trip with some strangers from Craigslist (you know, just to get that one last adventure out), I accepted the job. In a cubicle. At a bank.

Business Casual and the Harsh Reality Check

I just have to say, that after you’ve waitressed for years and years and you finally take your first “real” (salary) job, you see your paycheck and go “what the _____?!” With taxes and benefits taken out of an entry-level salary divided by 52 weeks, my new beginning was looking questionable. It was barely enough to cover my rent. I still needed to work a second job (which, thankfully, I didn’t mind). “There’s got to be more than this,” I thought. “Who actually likes this? Who actually signs up for this?”

Over the next several months, I was looking into programs that would allow me to teach English as a second language (ESL) in Costa Rica. I was trying to find out what it would take to become a translator for the UN. I wanted to do bigger things and I wanted my income to correlate to my efforts, not some formula decided by some big-wig in an office somewhere.

Like with waitressing, my take-home tips were directly related to my performance. Do a good job x take a lot of tables = pocket full of cash. I was making wayyyy more money waitressing than I was sitting behind a desk and, still the question lingered, what exactly do I plan to do with this fancy education I took out all these loans for?

Because they were coming due, let’s not forget that.

Finally I Quit

Well, not just yet. At this point in the story I’m still 22, green and eager, determined to make everything my own, and trying really hard to prove myself to just about everybody. But you can’t make a jigsaw puzzle piece fit into a lego. We can fast forward through the next 8-or-so years where I climbed the corporate ladder, impressed my bosses and mentors enough to create new positions for me just so that I’d have some ownership and autonomy in a world that so wasn’t built for me, and bent over backwards to meet other people’s objectives before going home at night wondering what the purpose or meaning was behind any of it.

I was paying my bills, but I wasn’t fulfilled, and I wasn’t using my talents.

After switching jobs and industries to reduce my commute and start a marketing department from the ground-up for a company that really needed one, I landed a fancy title and fancy office but I was more frustrated than ever. The bureaucratic nonsense that overrode any buy-in necessary to do my job and deliver as promised was causing major interference in my brain waves.

Around the same time that I was banging my head against the wall in corporate hell, my personal life started requiring more flexibility. People close to me were having health issues and needing medical procedures. I was being depended on.

The bosses didn’t like this, and didn’t take kindly to me asking for time off as a recently hired employee who hadn’t yet fulfilled the straight 90-day obligation of time done in exchange for human decency. I had to beg, plead, coax, finagle, and overcompensate my way into and out of tenuous conversations and use the sympathy card as a bargaining chip too many times for my comfort. This was demeaning. These people didn’t know me or my family, and they sure as hell didn’t care (at least not as much as they cared about their own bottom line), so why was I letting them dictate the terms of my life? For an unfulfilling job and a paycheck?

Hold please.

My Most Marketable Asset Was Me (All Along)

To say I was “done” would be putting it mildly. I would actually lay in bed, snooze my alarm multiple times, and stare at the clock telling me I was already wayyyy late, thinking, “I don’t even care if I get fired today. There’s got to be something more to life than this.

Something funny happens when you’re in charge of building a department from the ground up, without a team, and without buy-in. You have to get really creative, really resourceful, and try your hand at a lot of different things. All of my experiential experimentation amassed me a small mountain of foundational know-how — enough to assure me that I could take what I’d learned and do it on my own for a much larger (and more appreciative) client base. It was time to put my money where my mouth was.

Showtime! I gave myself a crash course in entrepreneurship 101: I decided what I would offer, who I would serve, what problems I would solve, how I would do it, what I would charge, and how I would find my audience (or help them find me) — and there were multiple iterations of this plan, by the way, which is the beauty of entrepreneurship. It’s a perpetual permission slip for reinvention. I created a website, another skill I’d picked up along the way), and then I did this.

I redid my resume — twice. As in, I created two distinct versions of my resume and released them both into the world simultaneously. Fly, little butterflies. Bring me back good news.

You see, I was still employed — so I needed to be careful about the manner in which I foraged for opportunities. I couldn’t go all primetime radio announcing my website to the masses for fear of being found out by my employer, but I knew enough to know that “if you build it, they will come” is not a solid business plan.

So, the resumes. One was the standard corporate variety, updated to the millisecond, with all the back-patting and storytelling I could fit onto one page. And the other was something I’d never even considered until the very moment I breathed life into it — a sort of freelance sales sheet. I provided all the precursory experience and qualifications, whatever felt relevant, anyway, but then I listed my newly formed company and my newly birthed services as though I was a subcontractor-for-hire.

The next part is what’s most essential.

I Prayed and I Trusted

After posting the resume files to job boards that I was fairly certain my current employer wasn’t checking, I wrestled with myself a bit. I asked myself the tough questions, like, “Are you prepared to struggle? How is this any different than being a starving artist going on auditions? Are you crazy? People don’t just quit their jobs and start their own business and have their income immediately replaced! They have savings! You don’t! What are you doing?”

But my family needed me, I needed to be there, and everything in me was saying “You’ve got this.” For some reason, I really wasn’t scared. I was actually pretty calm. I made a deal with myself that whichever opportunity came my way that was better than my current situation, I would take it — but I was gunning for someone to hire me as a freelancer. I wanted to take that chance on myself. I felt more confident about that than the singing or the language skills that I spent a fortune on. And I thought, “So what? If I have to struggle for 6 months, a year, who cares? I’ll go get another waitressing job to hold me over until business picks up and at least I’ll be struggling on my terms and calling the shots while I’m able to be there for the people that matter.”

And. then. this. happened.

I got a call, or maybe it was an email, I don’t remember, from a company that ended up becoming my first client and that is still a client today. They were interested in hiring me as a freelance marketing subcontractor for their small business. A series of calls and interviews transpired and I gladly took the job. I had my first client! And the best part was this: the job promised enough hours to nearly replace my full-time salary.

I couldn’t wait to put on my new identity and start giving people the me I knew I could be, without all the rules and roles of corporate. And before you ask, no, I am not someone who ever thought of myself as a CEO or someone with a fancy title. I’ve been told, frequently, that I’m “leadership material,” but I never knew what it meant and I didn’t really believe it. Until this moment.

The Perks

So much gratitude. I probably thanked God 1,389 times a day. I was able to take care of loved ones and work strange hours. I wasn’t expected to be always “on” or on-call or responsive at certain times. I was allowed to make my own hours and set my own routine. I delivered what I promised and I spent the rest of the time working on my budding business, pushing the needle forward with activities that I knew were going to pay off in the long run because they were an investment in myself and my reputation.

Another job came, and another, and another, until I had a nice little client base. I was working full time and I was the boss of my own company! Yippee!

Now before you go thinking entrepreneurship is all sunshine and rainbows and that every aspiring CEO’s story is as happy as mine, I have to burst your bubble. Most people are not as fortunate to have the outcome that I had. There usually is a trial period — sometimes years — where it takes a lot of persistence, faith, and experimenting to grow and scale.

And I’ll tell you, just because I own a business and I make a living, doesn’t mean I’m a millionaire. I’m paying my bills, sometimes more easily than others, but it’s not like I did this as part of some attempt to get rich quick. It was never about that for me. And I still have my moments of doubt, impostor syndrome, what-ifs, “is it worth it” — but I always come home to my truth.

It was about helping others, helping myself, and never having to answer to anyone again when they tried to tell me that their stupid job was more important than my dad or my significant other or my own health and happiness. EFF THAT.

So if you’ve stuck with me this entire time and you’re still here, thank you for reading. If you’re just now getting to know me, I’ve been in business almost 7 years and I recently rebranded and relaunched my company so that I can scale and serve more.

It feels so good and so aligned to know that I have the final say in how I can and will use my talents, on what, and for whom — it doesn’t matter how much they cost or what box someone once thought they should fit into. They’re mine, and they make my best asset endlessly more valuable — ME.

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.

Episode 6:
listen here

Read the article

Episode 11:
listen here

Eyes on Fire author and creator of The Unseen Realm fiction series, empath Carrie Hiott Richmond uses her firsthand experiences with inner & spiritual healing to navigate life in a way that is not only truly soul-aligning but also deeply fulfilling. I had the privilege of joining Carrie on her podcast, Southern Glow, in episodes 6 and 11, to talk about astrology in a biblical context and what it's like to work with an astrologer personally and professionally. 

Astrology in a biblical context

Overcoming Imposter Syndrome

Overcoming Imposter Syndrome

Recently Bold Journey graciously held space for me to tell the story of my own bold journey through entrepreneurship (with all of its twists and turns). Imposter syndrome happens to all of us, and in this interview I chat about learning to treat it as something to dance with and get curious about, rather than treating it as something to overcome.

Recently Bold Journey graciously held space for me to tell the story of my own bold journey through entrepreneurship (with all of its twists and turns).

Imposter syndrome happens to all of us, and in this interview I chat about learning to treat it as something to dance with and get curious about, rather than treating it as something to overcome.

As Seen In...

get the guide

In this free guide, I'll ask you the important questions that will reveal whether or not your website is optimally serving you. If you don't answer yes to at least four of the six, we need to chat. It's time to get real. 

How to Know if Your Website is Working For You

free guide!

free PDF guide!