Financially Wealthy But Creatively Bankrupt — Why I Pulled The Plug On My Career At 30

A Look Inside My Career Journey And The Impetus For Change

Once I accepted the advice of my Dr. Phil look-alike high school guidance counselor, I wondered if I’d one day regret it.

That meeting took place over 15 years ago. Looking back, it turns out that I never should have taken his advice. That one meeting was a pivotal moment in my life, a moment where every decision I made after that point changed my life forever.

While I’m grateful for all I’ve accomplished following that meeting, I can’t help but wonder if my life and career would’ve turned out differently had I followed my desired path instead.

For anyone who finds themselves lost in their career or wondering just how they got to where they are, this story is for you.

A fateful meeting

It was my junior year of high school.

All juniors had to meet with their guidance counselor to discuss their college and career plans. To be honest, I wasn’t looking forward to meeting with mine. I never got nervous meeting with authority figures growing up, but I always felt insecure when telling others about my dreams.

I was afraid of being laughed at and questioned relentlessly, or faced with disappointment that my decisions didn’t align with others’ expectations.

I knew what I wanted to say when I went into my counselor’s office, though: I planned to go to college and study journalism.?

When I sat down across from my counselor, he had his usual stern look on his face. If you were sitting in that room with me, you couldn’t help but notice the similarities to Dr. Phil. My counselor was slightly younger than the famous television personality, but had the good doctor’s matching bald head and goatee. He spoke softly but with authority, and you couldn’t help but sense his disappointment if you did something he didn’t like.

After telling him my college plans, including my desired dream job of being a beat reporter for the Chicago White Sox (yes, I know how unrealistic that was), I immediately sensed that I had shared plans he wasn’t fond of.

“You don’t want to be a doctor or a lawyer? Or an engineer? You’re very smart,” he asked me.

“No, I’m not really interested in that,” I responded.?

When asked what my backup plan was (I was well aware journalists didn’t make much money), I mentioned my other teenage career ambition, becoming a General Manager for a professional sports team. My counselor told me that the job was a lot of hours for not a lot of pay, and there likely weren’t many real opportunities available for that type of job. I figured as much, but was especially na?ve at that age.

“You know what you should be,” he said. “You should be a Human Resources Manager.”

“What’s that?”

“You hire and fire people. You’re pretty even-keeled. You’d do well at it.”

Thus began my exploration of business and HR careers. I decided to major in Business Management and complete multiple HR internships while in college.

Giving up the writing dream

Even though I loved writing more than anything, I felt more than prepared to let go of my journalism ambitions for the business and HR world.

For one thing, I grew up in an upper middle-class home. I never knew financial insecurity. My parents made good money in respected Information Technology (IT) careers. We never had to worry about where our next meal would come from or whether my brother or I could afford college.

I was very privileged, to say the least.

When I saw journalists earned around $50,000-$60,000 a year, I couldn’t help but wonder if I’d be able to afford the lifestyle I wanted on that type of income.

I knew approximately what my parents made, and I liked the pleasant home we lived in and being able to go on nice vacations. When I compared the prospects of journalists’ pay with that of an HR Manager in the business world, my decision seemed easier. It didn’t hurt that my heart pounded with nervousness whenever I had to approach a source for an interview for one of my high school newspaper stories.

After attending a summer business camp prior to my senior year and seeing the variety of career options available in HR, I gave up my journalism dreams.

I valued becoming financially wealthy and declared creative bankruptcy.

Expectations vs reality

When I got to college and began my studies, I felt like I made the right choice.

The business world fascinated me. There were so many interesting subjects. So many moving parts to making a successful business run.?

I knew the importance of getting internships in my chosen field early on, so starting with my sophomore year, I took on an unpaid recruiting internship with the American Red Cross.

After a few other internships and completing my studies, I’d done what few people could do when I graduated college: get a job in my field right after graduation.

While I was very grateful to get a job and live on my own right away, it only took me a few months to question whether my entry-level job in HR was something I wanted to keep doing for my whole life. I kept looking at other options, such as pursuing law school, getting a master’s degree in HR, or even considering getting into the IT field like my parents.

It didn’t help that I was still living in the same town as where I went to college, with my family back in my hometown and most of my friends in Chicago.

My burgeoning career dissatisfaction coupled with an unfulfilling personal life made things very dark for me, that is until I rediscovered my love of writing.

Searching for a creative outlet

Since I wasn’t happy at my job, I knew I had to inject more excitement and meaning into my life.

In early 2015, I fell into the world of self-help and personal development. This started by listening to James Altucher and Lewis Howes’ podcasts and even morphed into me taking a course from Ramit Sethi on how to build an online business.

Before I rediscovered my love for writing, I thought starting a business would be the right path for me.

I guess you could say I was sold on the dream of working from anywhere, making money while I slept, and taking off in the middle of the day to meet friends for lunch.

Because of my HR background, I thought starting a business as a career coach would be a great fit (only now do I see I'm finally ready for it!) But back then, I was only 24 years old and had no clue what I wanted to do with my own life. I guess knowing a thing or two about resume writing and interviewing gave me the perspective that I would be successful in that role.

Somewhere along the way, I stumbled across one of James Altucher’s podcasts with Jack Canfield, who wrote the Chicken Soup for the Soul books.

James asked Jack how someone can find their passion if they don’t know what it is.

My ears perked up, because this is the exact situation I found myself in. I knew I didn’t want to stay in my HR job for my entire career, but I never felt truly passionate about anything. What Jack had to say next changed my life.

Jack said something to the effect of, “To find your passion, you need to go back to the time you were a child, when you had no cares or worries in the world. What did you most like to do?”

Building on that idea, James suggested to listeners to make a list of 10 things they liked to do as a child.

When I got home, I made my list. Included on that list was reading and writing. After neglecting fiction reading in college, I started reading thriller novels again and loved it. This led me to another amazing discovery.

Self-publishing became my saving grace

After getting back into reading again, I yearned to write something.

While I started tinkering with a story series I never commercially published, I stumbled across the Creative Penn podcast and website. I learned from the show’s host, Joanna Penn, how many authors were leaving the world of traditional publishing behind and choosing to self-publish their books instead. Some were even so successful that they were earning six-figures a year and had left their corporate jobs.

I was hooked on self-publishing.

Yes, the naivety of me thinking I could be the rare six-figure author returned, but I’d always wanted to write novels growing up.

I thought that most authors were just “chosen” out of thin air, though, and that I’d never earn a chance to write a book. It was very empowering that I could just learn more about the writing craft, practice by writing every day, and craft my plot for a book without anyone’s permission.

In November 2015, I participated in National Novel Writing Month (also known as NaNoWriMo) and started writing my first novel, One Last Kill.?

It took me over 3 years and many rounds of editing (along with hiring multiple editors and a cover designer) before I published that book.

Along the way, I wrote and published two more books in my Callahan Boyle Thriller Series, including a prequel novella, Marked For Murder, and a sequel, Era of Evil. It was the culmination of a lifelong dream to publish these books and I was so excited to earn some money online. I knew deep down, though, that I was going to need to find another path as a writer if I wanted to make a living writing.

A detour unfulfilled

While I was putting the finishing touches on my books, I discovered the field of copywriting.?

If there were ever a career that had more courses, sales pitches for joining it, and false promises, copywriting would be it. I even bought one of these courses and learned a ton about writing effective copy. I was hooked on becoming a copywriter. In late 2018, I partnered with a graphic designer to create a few portfolio pieces I could use to pitch potential copywriting clients hoping to start a brand new career.

Alas, come 2019, I knew I needed to publish my books and fulfill that dream before I could pursue a copywriting career.

I figured even if I needed to get a traditional copywriting job instead of going the freelance route, that it wouldn’t be a huge financial sacrifice for me, as I was grossly underpaid in my new HR job in Chicago at that time.?

Until one day, I reached a breaking point at work. I was tired of doing the work of 3 people and being paid for the outcome of half a person. I was sick of being unable to affect change in my role, feeling that my expertise wasn’t valued because a higher up thought their way was best.?

So I looked for a way out and applied for a new HR job, this time as a real Compensation Manager instead of being one in just title only.

I ended up getting the job, and I put my copywriting career on hold.

Reaching my breaking point

I liked my new job. For the first year or so.

I had a great boss I learned a lot from, supportive coworkers, and the best executive team you could ask for. I was on the path for a promotion, and was finally being paid what I was worth. Things were pretty good.

But underneath it all, I wasn’t satisfied.

While I was working on another novel, I still had an urge to write for a living, rather than making next to nothing as an independent thriller author.

I wondered if I should reconsider exploring the copywriting path and give a shot to pitching potential clients. The only downside is that I was making significant money in my new role. It would be much harder to go from a mid $100k per year job to a job that was lucky to pay in the mid $50k range (if I became a full-time copywriter at an ad agency, for example).

On top of that, I realized being a manager and overseeing significant project management responsibilities wasn’t a great fit for me.?

I was working a lot of hours and was more stressed than I’d ever been in my life.

I knew that if I kept up with this path and climbed up the corporate ladder, I would feel creatively unfulfilled, despite the income potential. I’d never feel like I’d given my writing the shot it deserved. As a single 30-year-old with no debt or anyone else relying on me, I decided I needed to quit my job to have the space to pursue what I wanted.?

I left my job on October 8, 2021 and closed that chapter of my life.

A new career direction

When I first left my job, I wasn’t 100 percent certain what I wanted to do.

Part of me turned to something practical, like HR Consulting, since I knew the field well and could charge good money for these services right away. But this practical part of my brain kept me from taking risks in my career for so long. I knew writing and creating is what would make me happiest, so by November 2021, I pursued that full-stop.

Even though I’d explored copywriting before, I wasn’t sold on that path either.

I just knew that I wanted to write for a living, but I hadn’t decided on a specific direction.

Until I discovered UX Writing. I had no idea that there were writers responsible for designing a human-centered user experience for customers of apps and websites. The helpful text I saw when ordering an Uber or Lyft was written not by a traditional copywriter, but by a UX Writer embedded in a company’s product team.

After taking a 15 Day UX Writing Challenge and enrolling in a 6 month UX Writing bootcamp, I discovered that UX Writing was a great career path for me.?

Almost 2 years in, I’m proud to say that I’ve found a career where I can utilize some of my best skills every day while doing work that I’ve felt passionate about.

Purpose > passion

But at some point last year, my personal growth challenges pointed me to a bigger mission and vision than I ever could’ve imagined. Writing has always been a passion of mine and it feels great to make a living as a writer. Yet, I wondered if the writing had to be the focus of my work, or if it could support a bigger vision.?

Hiring a therapist and coaches has helped me see the transformative power of working with others 1:1 to help them unlock their potential.?

At the end of 2023, I knew I wanted to engage in this type of work, too. I had a new calling, not toward my passion for writing, but toward my purpose of unlocking transformation and reinvention.

I enrolled in a Jungian Life Coach training program and have combined this training with my decade of HR experience and my process for making a career change into my own offering as a Career Coach.

Even though I’ve only been coaching for a short time, I’ve been amazed by the insights my clients have seen from each session and can’t wait to help others see even more growth within.

What this means for you

If you’ve read this entire article, thank you.

If you’re feeling stuck in your career, I hope you can learn a lesson or two from my journey. Yes, you can find a fulfilling and meaningful career for you. No, it may not be what you first expected it to be.?

I would’ve loved to have been a six-figure thriller author when I first set out to write novels.

Even though that didn’t happen, I eventually landed a writing career with six-figure earning potential.?

Beyond that, I’ve found a new purpose for my career. I can enjoy a career that provides me with financial security while building a coaching business that allows my creativity to flourish. It may have taken me over 15 years since meeting with my high school guidance counselor to figure out what I wanted to do with my life, but now that I’m here, I wouldn’t trade it for the world.