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Alright, friends. Welcome to Part Four of my Pitch to the Top™ story, where I finally tell you how I became a CNBC reporter after working as a kindergarten teacher. This post is a long one, but it’s jam-packed with practical tips, nuggets, and take-aways from everything I learned during the ups and downs of my journey, which ultimately led me to write for a major news network.

It all started with one essential moment: A decision.

For years, I waffled back and forth, unsure how to be a writer, worried I didn’t have enough talent, and scared of being visible. I had some unpaid internship experience, but I didn’t know how to get the real writing opportunities I desired deep down.

So one day, I googled “how to be a writer” and found an online course. It was $200. I couldn’t really afford it, but I signed up for it anyway. It was my first non-academic investment (besides my yoga teacher trainings) in myself.

And boy, did it pay off.

But it wouldn’t have paid off without me first making the decision to pursue the path wholeheartedly. That was the key.

Here’s how it all went down.

Recovering from a failed business

When we left off in Part Three of my story, I had just failed at starting my first business. And to make things worse, I had just broken up with my boyfriend (and my financial safety net).

I needed a job, but nothing I found in Asheville, NC where I lived at the time paid well enough for me, a former AmeriCorps volunteer and yoga teacher with a bachelor’s degree in Spanish, to thrive in my career.

I took a part-time teaching assistant job at a Title 1 school making $12 per hour. I loved the school, my co-workers, and my students. The experience itself was eye-opening, too. If you’re unfamiliar, Title 1 schools are those in which at least 90% of the students qualify for free or reduced lunch. I didn’t realize at the time that this experience would plant the seed for me to start observing how money shapes peoples lives.

In the six months I taught at this Title 1 school, there was an active shooter lockdown (not a drill, but a real, live alert), two shootings between neighbors in my students’ neighborhood, a police shooting in the same neighborhood, and a tragic murder (one of the kindergartner’s fathers took her camping and killed himself as well as his daughter). I saw plainly how poverty and violence co-mingle, and I thought deeply about what the futures of those bright children I was getting to know every day would be like.

ABOVE: A sweet card from one of my first students.

Despite the violence, which seemed like it was everywhere, the school environment itself was super supportive and even felt like home to me after just six months. I didn’t want to leave that job, but I needed a full-time salary. Since I was close to finishing my master’s degree, my professor and mentor suggested I look into teaching at independent schools (you don’t need a state-certified teaching license to work in private schools).

I applied to schools across the country, including ones close to North Carolina. I heard back from one in Silicon Valley, and within a few weeks the school offered to fly me out to interview and take a tour. Needless to say, when they offered me the job, I said “yes!”

In my last post, I mentioned that careers are not linear ladders, but rather more like rivers. The switch from teaching at a Title 1 public school in southern Appalachia to a private school with $50,000+ per year tuition in Silicon Valley was such a strong contrast that my interest in money swelled. Teaching at such a resourced school with a progressive pedagogy felt like perfection, and I desperately wished that all students in the U.S. could get access to such high-quality education.

But, we live in a paradoxical, imperfect world. I soaked up my experience living in the SF Bay area, commuting from Oakland to the peninsula and writing poetry on the train while I finished up my master’s degree at a distance.

ABOVE: For Halloween, I dressed up as a teddy bear. The things we do for the kiddos.
ABOVE: This photo, snapped by one of my students, really captures my essence — don’t you think?

Planting the seeds for New York

During my year in California, I flew back home to the east coast a handful of times. My grandparents were starting to show their age, and I began to get the intuition that my grandpa would soon pass away. I started calling my grandparents every week and visiting as often as I could. I therefore found myself flying into New York City more often than I ever expected to, since my grandparents lived just an hour and a half outside the city in the Pocono mountains.

ABOVE: Me on the Chelsea High Line in 2017.
ABOVE: Me, my middle school bestie, and Lady Liberty.

I also started to get the intuition that I would move to New York, but I didn’t know how or when. If you find yourself getting similar little inklings, trust them. But don’t force them. Things unfold in their own time, as I would soon learn.

Graduating from my creative writing master’s degree program

In the spring of 2017, I finished my graduate thesis, a poetry collection of prose poems in the voices of my ancestors called Ghost Stories. I started submitting my poems to literary journals.

I graduated in May, 2017 from Lenoir-Rhyne University Asheville’s Master’s program in creative writing.

ABOVE: Me (middle), my mom (left), and my professor, Laura Hope-Gill (right)

The sinking feeling of debt

Immediately upon graduation, I realized I was in five-figure (almost six-figure) student loan debt. But I also learned some of my poems received honorable mentions, including a third prize in poetry for the SF-based literary festival, LitQuake.

I kept thinking that these poetry accolades would lead to more money, fame, and glory. But really, they just made me feel good and that was about it. I didn’t understand how the literary world worked, and while the praise and encouragement was nice, I began to get legitimately stressed about my future.

Realizing I needed to increase my salary and lower my living costs, I applied to lead teacher jobs at private schools in Baltimore, close to where I grew up. I negotiated my highest salary to date ($55,000) and worked as a kindergarten teacher for another year.

The online course that changed everything

In winter of 2017-2018, I signed up for an online course about freelance writing. I joined the free Facebook group that came with the online course, but I didn’t really engage. Some might have called me a “lurker,” (in fact, the leader of the group did!). I was too scared to start connecting with people and admitting that I, a poet with a master’s degree in creative writing, didn’t know the first thing about how to be a writer.

The (brief) return to academia

Even though I was learning oodles of helpful information from the online course, I went running back to academia as though it was my security blanket. I enrolled in yet another graduate program — this time, Carlow University’s MFA program, which offers a summer residency at Trinity College, Dublin.

With no path to making money as a writer (yet), I chose to go even deeper into student loan debt. I was honestly flattered that I’d gotten into an MFA program, since they have a reputation for being notoriously selective. (I was still living from a place of insecurity and suffering from a serious case of “pick-me!” syndrome.)

During my summer residency, I met memorable friends and mentors including the Irish novelist, Evelyn Conlon. I spent the summer traveling through Italy and Ireland with one of my classmates, Daniela. Since Daniela was born and raised part-time in Italy, she and her Uncle Ennio generously offered to drive me to my great-grandmother’s birthplace, a tiny village in the Campobasso province (Molise region) called Riccia. My hosts, Anna and Antonio, took me to the historical record office where the record keeper showed me my great-grandma’s birth certificate. Pretty neat!

Another year, another job hunt

When I got back from Europe, I was broke and needed money (are you noticing a pattern here?). I decided I wouldn’t finish the MFA — I didn’t need one for the path I wanted my life to take.

So I started applying for jobs far and wide across the Baltimore/D.C. area. I got better at writing resumes and cover letters, but without a strong portfolio I always faced confusion from the people who interviewed me. Who was I, exactly, other than a kindergarten teacher who wrote poetry in her spare time? My accolades didn’t seem to mean much to editors, who could sense I didn’t understand how digital publishing works and how the editorial department serves as the engine for most business models.

I tried to bullshit my interviews. It worked OK, and even got me through two phases of the interview process for a money writing job at a Baltimore-based financial publishing company. Two team members were interested in me, but the head of hiring wasn’t impressed. I was disappointed, but the let-down made me realize how much I wanted to write about money. Though I was bummed I didn’t get the job, I’d learn that the universe had bigger plans for me.

I soon set up my first portfolio on Contently. I started sending a lot of really, really bad pitches and letters of introduction to businesses and publications. None of them got back to me. I sent hundreds of job applications into the universe, including a few door-to-door Verizon Fios sales jobs. They rejected me, too. This was a period of DEEP “pick me!” syndrome.

ABOVE: This is what my Contently portfolio looks like at the time of writing this blog.

The job that changed everything

August 2018: I accepted a development job at the Association of Writers & Writing Programs (AWP). The biggest selling point — apart from working with a fabulous mentor and being surrounded by small literary presses — was the organization’s two-day-per-week remote work policy that gave me a flexible schedule so I could start pitching and freelancing on the side. I took a pay cut, however. I made $42,000 then negotiated my salary to $52,000 within about six months.

In this time, I started dating another writer, who would go on to spend the next two years applying for MFA programs. We spent a lot of time workshopping each other’s stuff. Neither of us knew how to be a writer, but little did we know we were actively becoming writers, despite how new everything felt.

Working at a literary membership organization

I worked at AWP from August 2018 to September 2019. I helped organize the gala, Braver Together, featuring special guest Cheryl Strayed. I attended AWP ‘19 in Portland, Oregon.

ABOVE: Me and Cheryl Strayed. I was so stressed that I didn’t notice my hair looked like Mugatu’s from Zoolander.

Learning to put myself out there

In early 2019, I finally decided to make friends in that freelance writing Facebook group I’d joined. I got over my fear and asked for guest post opportunities for people with personal finance blogs. I revised my Squarespace website (and revised it a hundred times more). I learned how to tell my story and sell my life experience as the expertise it truly was. I learned that my point of view was valuable. I got my first invitation to write a guest post for a blog called Wallet Wise Guy. I wrote it for free, and it took me hours.

I pitched, pitched, pitched. I sent hundreds of letters of introduction (LOIs).

I signed up for another group coaching program that met weekly for Q&As and pitch critiques.

My big break

Then, it came in June, 2019: my big break. A blogger I had sent an LOI to connected me with a Business Insider editor in need of freelance personal finance contributors. The caveat was that we had to write about our personal lives.

Gulp. I had made so many money mistakes that I couldn’t believe what I was about to do.

I crafted a pitch about the money realization that gave me the confidence to leave teaching. The editor liked it, and the story became my first BIG byline. I then got semi-steady work at Business Insider.

Around the same time, a well-known and established blogger/author hired me to write the credit cards silo on his blog. He paid me for a few articles at first, then started to pay me in upfront in advance, often a month’s worth of work at a time.

The Marie Claire story that never sold

Alongside these successes came some fails, too. I had one of my first major freelance “learning moments.” Inspired by my trip to Italy to learn about my great-grandmother (who was a child bride), I pitched a story to an editor at Marie Claire magazine about how child marriage laws were changing in Pennsylvania, where my family lived for generations (many still live there today).

My friend, Daniela (the one who took me to Italy), was part of the activism that led to the law being changed. The Marie Claire editor got back to me expressing interest in the pitch. Her mild enthusiasm was enough to send me spinning off in glee. I went all-in. I traveled to Harrisburg twice to follow the story unfolding in Pennsylvania. I met activist and former journalist, Fraidy Reiss, who escaped from a forced arranged marriage in her 30s. I owe big thanks to Reiss, who took me seriously and generously offered to let me interview her, follow her around, and learn about how she works with legislators to change laws. I was starstruck. A real former journalist, letting me interview her!

ABOVE: Fraidy Reiss speaking in Harrisburg, Pa.

I quit — just kidding

I started getting more clients and began writing steadily for WeAreTeachers, Robinhood, Business Insider, and other occasional clients. I had my first $7,000 revenue month from that blogger I menioned above. Freelance money was finally good enough to quit my job at AWP. I purchased a ticket to FinCon 2019 in Washington, D.C.

But then, I freaked out about quitting my job. So, when a recruiter surfaced from one of the hundreds of applications I’d sent out in prior months and asked me to interview for a $70,000 writing job for an educational nonprofit, I said yes.

FinCon

September 2019: I attended FinCon during the second week of onboarding at my new job. Stressful, but also genuinely inspiring to see all those independent media brands making a living for themselves. My wheels began to turn, and turn, and turn.

No seriously — I quit

FinCon was inspiring enough to make me want to do the freelance thing again for real. I would make it work, I said. So I told my new job (the $70,000 gig) that I’d made a mistake and that it wasn’t going to work out. My co-workers were encouraging and understanding.

Pursuing the story (and funding all the research myself)

October 2019: Still in conversation with the Marie Claire editor, I traveled to the Virgin Islands to keep following the child marriage story. The USVI would be next to introduce a ban on marriage under age 18. How exciting, right?

Wrong. I should have read the signs better. I realized after going all-in on the story that the Marie Claire editor had moved on. I had to accept that such is the nature of publishing sometimes. Nobody wanted the story even after I traveled all over the world and interviewed senators and activists. Even after Fraidy Reiss graciously let me tag along as she spoke with legislators. Even after I met USVI Senator Javan James, who introduced the child marriage ban, and he invited me to eat a catered lunch with his fellow legislators.

ABOVE: Senator Javan James (center left) and Fraidy Reiss (center right) after the USVI hearing on the child marriage ban.
ABOVE: Reiss and her staff member speaking with USVI senators

I eventually sold the child marriage piece for just $200 to a niche publication for teachers. The story was later accepted into the Solutions Journalism story tracker database (a small consolation). 

The two surprises I didn’t see coming

November 2019: I applied to a writer/editor position at CNBC Make It. I learned it was for a new e-commerce vertical, Select. The recruiter contacted me and scheduled interviews.

Then, without any warning, Business Insider dropped me by December of 2019. I was honestly pretty blind-sighted, even though I shouldn’t have been. Freelancers are the first to go when budgets change, and you don’t always get notice when higher-ups make decisions about which direction they want to go.

New opportunities and horizons

Thankfully, the timing worked out well. I had my first remote interviews for CNBC Select in late November/December 2019. Then, in December, my poem, “Aubade for an Alcoholic’s Son” was nominated for a Pushcart Prize.

I had my final CNBC interview (in-person) in January, 2020.

A new chapter — sort of

January 2020: I accepted the CNBC job — my first six-figure salary — and planned to move to NYC by March 2020.

In February 2020, CNBC brought me to NYC, put me up in a hotel, and on-boarded me to my new role in the 1221 Avenue of the Americas building across from 30 Rock.

But then, as we all know, the coronavirus pandemic hit. I stayed in Baltimore until July, 2020 before moving to a tiny apartment with that same writer boyfriend who’d gotten into NYU’s MFA program for fiction. We spent 2020 in a one bedroom apartment writing our hearts and brains out (which isn’t as romantic as it sounds!). 

I spent the year working remotely to build Select with a small group of three full-time staff members. Select was not just a stepping stone for me: It served as the proverbial “woodshed” in which my service journalism skills got sharpened up. I am eternally grateful for my time working with the CNBC team.

For basically all of 2020 and the first half of 2021 — and in my quarantine loungewear — I interviewd top financial planners and thought leaders such as Depak Chopra and Ellevest’s Rachel Sanborn Lawrence. Not exactly how I pictured it, but hey!

Leaps and milestones (the ups and downs continue)

Even though landing the CNBC job was certainly a dream opportunity, the ups and downs of life don’t just stop because you’ve leveled up in your career. If anything, the challenges came with greater frequency and intensity, and I had to calibrate my nervous system to deal with the new demands and circumstances of my life.

The year 2020 was a challenge for all of us. Many of us lost loved ones, we all adjusted to a life without travel and social gatherings, and everyone lived in fear of losing their jobs. I felt enormously grateful for such gainful employment and an opportunity to help answer important questions for readers about their stimulus checks, debt forbearance, unemployment checks, and more.

And I also started dreaming about being self-employed again.

In December 2020 I started preparing to upgrade my website to a better blogging platform. I switched to a WordPress website, known for being better for search engine optimization (SEO).

February 2021: I finished the first full first draft of the novel I’d started in grad school, Adventureland. I paid $1,300 to have an independent editor read it over. I got great feedback with lots of notes, then put the book away to marinate in the creative subconscious for a bit.

March, 2021: My boyfriend and I broke up and I moved into my own studio apartment in Manhattan’s Carnegie Hill neighborhood, committing to giving myself at least one honest year of being a self-employed writer in NYC.

April 2021: Two of my CNBC articles were cited in Elizabeth Warren’s proposal to U.S. Secretary of Education Miguel Cardona. Another was listed as a source in Christine Platt’s The Afrominimalist’s Guide to Living with Less (Tiller Press | Simon and Schuster, 2021).

June, 2021: I decided to quit my job to go fully freelance. Within weeks my calendar filled up entirely with new clients, which I then had to sift through and decide which were the right fits for me. I was overwhelmed, but I got things moving smoothly after a few months of adjusting.

For now, I’m happily writing and editing in the personal finance space — but my heart and intuition are always thinking three steps ahead. Freelancing has taught me that there are no limits to what experiences we can have, or how much income we can earn. The only limitations are self-assigned, and they can always be changed or refined.

I’m personally excited to see where freelancing takes me next. I’ve already had the chance to interview incredible people through my freelance work, and my next goal is to make my conversations more visible and engaging for all.

Don’t miss:

My Pitch to the Top™ story Part 1: The unpaid internship phase

My Pitch to the Top™ story Part 2: How I finally got paid to write

My Pitch to the Top™ story Part 3: Self-employment lessons for keeping a growth mindset

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