How I Went From Making $23k To $100k In Just 4 Years

In 2011, I walked out of LaGuardia airport with two suitcases, got into a cab, and arrived at my sublet in Forest Hills, Queens — found via Craigslist. I tossed up a small prayer asking that I not be walking into some heinous trap. Two days later, obviously still alive and unscathed, I started my first post-college job working as a page at The Late Show with David Letterman. While seeing celebrities every day and feeling part of the television industry put a dopey smile on my face à la Kenneth from 30 Rock, I couldn’t survive on the paltry paychecks of $180 to $240 a week — without either draining my savings or going into some serious credit card debt.

Not keen on either of those options, I began applying for every flexible job I could think of: Starbucks, babysitter, movie theater usher, hostess gigs at restaurants. I wasn’t above earning minimum wage. Eventually, I donned a green apron and learned how to make your favorite Frappuccino in the mornings, and I babysat for a rotation of three different families in the evenings.

My days were an exhausting loop of opening a Starbucks in Manhattan, shifting to getting audiences pumped to watch The Late Show, and then keeping children entertained at night. By my one-year anniversary of living in New York, the time had come for me to get my first “real job.” The page gig only lasted a year, and I felt worn out from hustling through three jobs just to make ends meet. I decided to leave entertainment behind and join the ranks of the PR girls.

Don’t even think of comparing my job to that of Samantha Jones. An acquaintance from college put my résumé in the hands of a hiring manager at a boutique agency specializing in tech PR. He gave me a few tips on how to ace the interview, and two weeks later, I found myself shifting from the page uniform to suddenly wearing dress pants, a blazer, and far less sensible shoes. The job started as a paid internship, so the company could vet and train potential entry-level employees without offering benefits or a full salary. In early August, I got promoted to the position of account coordinator. The offer letter outlined $37,500 in salary, employer-paid health care, a 401(k) with an employer match of 4%, and three weeks of vacation time. I didn’t even take a moment to consider negotiating and signed on the dotted line. I felt rich!

This was the year when everything began to change. I started my personal finance blog, BrokeMillennial.com; I’d begun to feel creatively stifled at work and craved an outlet. Writing a blog about money helped fill the void, and I soon found it could be leveraged into side-hustle opportunities. I never focused on affiliate income or monetizing my blog, but rather used it as a portfolio of work. When AOL’s now defunct outlet DailyFinance shared one of my stories on Twitter, I immediately responded and asked if they were looking for writers. This simple exchange on social media started my professional writing career.

By the end of 2013, I earned $1,770 from freelance writing — but more importantly, I’d learned how to ask for what I wanted. I started to put myself out there more and apply for other writing jobs in addition to continuing to work at my day job in PR.

By 2014 I felt overworked and underpaid, and I dreaded going into work each day. The jump from $23,000 to $37,500, now $38,625 from a meager raise, had felt like a lot, but not for the amount of work I put in.

I started sniffing around for different job opportunities. One came from a larger PR agency with a well-known bank as a client. I went through the interview process and eventually got offered a job that would be a promotion with a $6,000 raise. The catch: I’d have to stop freelance writing and shutter Broke Millennial. Meanwhile Broke Millennial was getting some attention, and I’d been featured by a few major publications such as Forbes and Reuters. I knew the site and my freelance writing could earn me the extra $6,000 — so I turned the job down.

Just two months later, a game-changing opportunity occurred. A financial services start-up in New York got in touch with me via Broke Millennial and asked if I’d be willing to come beta-test their pre-launch website, to which I agreed. Partway through the beta test, I took note of a small button for “blog” on the upper right-hand corner. I clicked on it, and went to an empty page. During the Q&A session, I asked the co-founders, “Have you decided what you’re going to do with the blog?”

“Not yet, do you have any ideas?” one replied.

“Yes. I can run it,” I announced confidently.

“Okay, write us up a job proposal, and let’s talk,” he responded.

I strutted out of that office feeling like I’d just found my ticket out. I spent a few days outlining the job responsibilities as well as a compensation package, which included desired benefits. After much deliberation, I decided to ask for a $50,000 salary. I came to this number because it felt like a huge jump from $38,625 — but not so high that I might price myself out of a start-up company’s budget. Truthfully, I felt desperate to get out of my current job and didn’t want to let this opportunity slip away because I had overpriced myself.

I sent the proposal to my dad for review. He approved it, and I submitted it to the co-founders. Three days later, I received an email saying the proposal looked good, and asking if I could I come into the office to talk.

Sitting across from the two co-founders, I assumed we were about to negotiate on my salary ask. Instead, I heard: “Your proposal looked great. When can you start?”

That’s when I knew I had screwed up. They didn’t even attempt to counter, which meant I could have asked for more.

Things were going well for both my new job and freelancing, but I still couldn’t shake the feeling that I’d drastically undervalued myself. I knew I needed to try and rectify my mistake come my annual review in April. I began prepping early.

First, I collected all my success from the year, which I’d kept in a folder on my desktop. I focused on metrics proving how I’d increased blog traffic, upped our social media engagement, and built out a network of contributors. Second, I began to research what someone doing my job at similar companies earned. Because it was a start-up and I was employee number-one, I worked in more than one role. I wrote a list of each job — from editor to content director to human resources to manager of the contributor network to social media coordinator. Then, I assigned a salary to each job based on information from sites like GlassDoor.com and Salary.com — as well as asking people in my New York City network.

Ready with all my metrics and research, I started to practice for the negotiation. I watched tutorials on YouTube and even did some negotiation exercises with my dad on the phone.

“Hey Erin, I was reminded your one-year is this week,” one of the co-founders said to me while casually swiveling in his desk chair. “We’re going to give you an automatic bump in pay of 5%.”

I’d been ready for this moment.

“Thanks, but could we do a formal review?” I responded. “I’d like to have a deeper discussion about compensation.”

Armed with knowledge and practice, I entered the negotiation arena and submitted my ask of a $20,000 raise — to $70,000.

After some back-and-forth and providing an outline for the upcoming year’s goals – the co-founders agreed. In addition to my raise, freelancing brought in around $21,000.

While filing 2015 taxes, I realized I’d earned almost as much this year in side-hustle income as I'd earned in total income back in 2012. I began to consider the possibilities of going into business for myself. Then, I signed a book deal to write the ultimate personal-finance guide for millennials. I knew it was time for me to consider leaving the comfort of my stable job and focus on building the Broke Millennial brand; otherwise, I would regret never taking the risk. I began to more aggressively pursue freelance opportunities and focus on saving as much as I could manage, to prepare for the transition.

I called a meeting with the co-founders and gave my notice in August. The discussion was amicable, and I even stayed on part-time through October while they trained my replacement. By November, I was completely self-employed.

Always a goal setter, I set a target to earn $72,000 during my first full year of self-employment because that would mean slightly out-earning my base pay when I had been traditionally employed. It's four months into the year, and I’m currently on track to earn at least $70,000 and set a reach goal of $100,000.

On May 2, 2017, my first book, Broke Millennial: Stop Scraping By and Get Your Financial Life Together, hit shelves in bookstores around the country. While I’ve poured much of my energy into trying to make the launch a success, I’ve also had to balance in earning a living. Truthfully, my physical health and social life have taken a beating in the process between the ordering takeout, lack of sleep, and minimal time to invest in being social. Being self-employed isn’t as glamorous as is often portrayed on Instagram, but I’m proud of my decision to bet on myself — and still feel grateful I didn’t give it all up for a $6,000 raise back in 2014.