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.
Advertisement
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.

I felt worn out from hustling through three jobs just to make ends meet. I decided to join the ranks of the PR girls.

2012: I fail to negotiate and earn $23,244.
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!
Advertisement
2013: I learn to side hustle and earn $39,291.
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.
2013 Takeaway: It never hurts to ask. The worst someone can say is "no."
2014: I create a job, earn $55,375, but screw up my first big negotiating opportunity.
Advertisement
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.
Advertisement
“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.
Advertisement
2014 takeaway: Switching jobs is one of the easiest ways to negotiate salary. It’s harder to drastically increase your income in your current job.

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

2015: Redemption: I learn how to negotiate and increase to $81,686
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.
Advertisement
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.
Advertisement
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.
2015 takeaway: Keep track of your successes as they happen throughout the year. Practice before a negotiation and learn how to determine and demonstrate your value to an employer.
2016: I bet on myself and earn $96,796.22.
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.
Advertisement
2016 takeaways: You are your best investment, but always try to leave your job on good terms; you never know what that could lead to in the future.

I earned almost as much this year in side-hustle income as I'd earned in total income back in 2012.

2017: I'm staying on target.
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.
Advertisement