Some time in 2017, I reached a breaking point.

I was 30 years old making $43,800 a year. I had no real savings, a meager amount set aside for retirement, more or less overwhelmed by my growing student loan debt, but had managed to scrape enough money together with my then-boyfriend, now-husband to purchase a small home in an “up and coming” neighborhood in Philadelphia. I was working a full-time job at a nonprofit, freelancing on the side, while also attempting (and failing) to run a business with a woman I had only recently met. I was burnt out, desperate, and at the lowest point in my life. 

Cut to: Five years later, I am working one job that I love, making six figures, my home value very much increased, my student loans on track to finally be paid off, and my retirement in a much better place. And yes, I’m a lot happier.

What happened? Simply put, I got really real with myself. 

But let me back up. To better understand how I got here, it’s helpful to understand how I got there. 

After college

In 2009 I graduated from the University of Pittsburgh with a degree in English, a minor in Economics, a certificate in Spanish language, and a medium-sized amount of debt. Judging from my various degrees, I had no clear idea what I wanted to do with my life, my ambitions at that time primarily focused on some vague combination of traveling and writing. Or teaching writing. Or volunteering. Or going on a months-long yoga retreat in Mexico. What I didn’t want, what I had sworn myself against, was any kind of “typical” job. You know, the ones where people make money. I couldn’t conceive of any 9-5, couldn’t imagine how anyone could spend their lives doing this. Commute? Who commutes? Who sits at a desk? Who packs a lunch? I was a part of a generation that was told by my doting parents that I was special and different and that I could do anything I set my mind to. Hell, as long as I found my passion, I would never work a day in my life. Incredible! 

(My older siblings, both squarely Gen Xers, must be laughing somewhere reading this.)

As graduation loomed and the global recession grew, I flirted with the idea of moving to Spain, a country I’d lived in for two months in a study abroad experience, to teach English. My parents, seeing the pennies I’d be paid in exchange for a job I was profoundly unqualified for  (my mother – a teacher herself who knew my level of patience was not a fit for controlling a classroom – balked). I considered moving anywhere, anywhere to avoid moving back home with my parents. Brooklyn looked interesting, right? Or Portland, Oregon, where my older cousin lived. Maybe I could be a cool barista? A starving artist in a hip loft? 

Eventually, I landed in Philadelphia on a whim: my best friend lived there and needed a roommate. 

I moved to Philadelphia in the middle of summer, my body unprepared for the heat after four years in Pittsburgh, where the sun’s arrival is a rare and delicious treat. I spent my first several months living there taking long, sweaty, aimless walks that usually landed me in Rittenhouse Park, or Ladder15, the bar my best friend worked at. I carried a notebook with me, but my writing was emotional, sparse dribble. Mostly, I drudged through my days until around 4pm, when it felt like an appropriate hour to start drinking. I had no job, but one prospect: a marketing company I’d interned for the previous summer was interested in hiring me to write copy full-time. It was the dreaded corporate 9-5 and would require a daily 30 minute commute to the suburbs, but considering that there seemed to be zero jobs available for recent graduates in 2009, I had better take it. I started in September. In the meantime, I tended bar a few nights a week at a dive near my apartment that had me wearing a uniform and standing on the bar top at hourly intervals to pour shots from the rail into customers’ waiting, open mouths. 

The new job forced me into a routine: wake up at 6:00am, shower and eat, out the door by 7:30am to make it just in time to park in the industrial suburb lot at 8:00am. (I was usually late.) The first few weeks, I came home and couldn’t do anything but lie on the couch. I was exhausted, but was making $600 every two weeks, which felt like a lot at the time. Once, I attempted to go to a grocery store in the city because I hadn’t had time between my weekend bartending shifts. I ran full speed into such an onslaught of city traffic that I called my mom crying. I was tired, hungry, exhausted in that weary, bone-deep way, but all she could hear was me hyperventilating over being stuck in traffic. 

The job didn’t last. They couldn’t afford to hire me full time, so I was hired as a temporary contractor, let go that January once money got tight again. My time as a 9-5er was over before it started.

Moving abroad

At some point during that time I had gotten it into my head that I needed to find a way to leave the country, which was offering me none of the promises it had sworn by: work hard in school, get into a decent college, do well, graduate, and get a job that made enough money to live on. I decided to go back to school, this time for a Master’s in writing, ostensibly to become a working writer and professor. The specific dream I had clung onto was that of seeing two of my favorite writing professors read aloud in a dimly-lit Pittsburgh bar basement. One was wearing all black, drinking red wine, with a clove cigarette behind her ear. She represented everything I wanted to be in that moment.

I narrowed my focus on England, and then specifically, Oxford, the country’s beating heart for writers. I applied, submitting some of the dribble that began to form something vaguely coherent, and received a phone call in the spring inviting me to join a group of 20ish writers that fall at Oxford Brookes University.

I was ecstatic. I now felt, finally, after a year of wandering, like I had a focus. And Oxford turned out to be everything I hoped it would be and more. I spent that year with writers from all over the UK and the world, reading a novel a week, writing voraciously, listening to talks from incredible visiting professors, and generally feeling like I found my place. I submitted my final paper, a piece of fiction with a quiet, misunderstood woman as the protagonist, and moved back to Philadelphia in the fall of 2011. 

And that’s when reality really set in.

Back to Philadelphia

I had held out a vague hope that my year away had been enough time to wait out the recession. But, just the opposite: the recession had seemed to grow more painful and deeper, grinding away as people with real degrees and actual job histories lost their jobs and struggled to find new ones. My attempts to find my way into higher ed were futile: I didn’t have the proper degree, I didn’t have enough publications, I didn’t have any relevant experience. (Unlike the UK, getting an MA or MFA in the states came with a year of teaching undergrads.) Four months after I moved home and still without any job prospects, I was head-over-heels grateful for an opportunity to work at a cafe not far from my new apartment I shared with my boyfriend. I was 25 with too much education and little prospects. With tips, I made $300-400 each week, under the table.

After six months working at the cafe, I was hired to teach middle and elementary youth through a nonprofit summer program. The work was challenging: instead of teaching reading and writing, the things I cared about and well, knew something about, I was struggling to wrangle middle school boys to focus on math during their precious summer off. After just a few minutes into my first lesson, an aghast boy asked me, “Wait, is this summer school?!” 

The days were long and tough – a solid 8am to 4:30pm, Monday through Friday, in an un-air-conditioned and unforgiving middle school building . With taxes, I made less than what I made at the cafe, but it was a “real” job.

When the summer concluded, I had no other job prospects, so I continued at the nonprofit through the school year, this time working with high school students as a writing instructor during the after-school hours. I had a solid group of eight students dedicated to spoken word poetry, and I coached them while they practiced and competed with other high school students in the city. I took them downtown for competitions, most of them having lived their entire young lives never having left the few blocks of their neighborhood. It was one of my most impactful and transformative experiences, but it was completely financially unsustainable. When I was offered a job as a brief writer at a corporate legal office the summer after that school year, I took it.

The law job lasted only a year. The work was challenging in a way I loved, but the company itself, with its odd norms and culture that required us all to scan our fingerprint every time we left the building (every minute we were late equated to a quarter-hour dock in pay) left me searching for something else. I was interested in getting back into the nonprofit sector, which still felt like a viable career path, and was soon hired as a grant writer at an arts nonprofit. I took a paycut and started at $30,000/year, which equated to $750 paychecks every two weeks. Nearly half of my monthly pay went to rent.

The job was flexible enough that I had time to write in the mornings before I arrived at work to write grants and manage other clerical fundraising-related tasks. I spent the two years I worked there writing short stories and finishing a draft of a manuscript that I’d started while working in the schools, still holding out a vague dream of living as a working fiction writer, the grant writing work just the job I needed in the interim before I could sell my first book. After two years, I left the arts nonprofit and was hired at another nonprofit, this one with a mission to help survivors of domestic violence. The work was much more difficult – I’d gone from requesting $1,500 from family foundations to support ceramic arts to requesting $150,000 from the U.S. government to support women and children fleeing their abusive partners. It was another transformational experience, and I learned so much about myself, my community, and the devastating hoops of social services through my time there. At the same time, I’d secured an agent who was interested in my manuscript, but asked for edits that would take me nearly six months to complete. I started waking up at 5:30am to begin writing by 6:00am. I would then leave my house every morning at 8:30 and ride my bike downtown, to write complex federal and foundational grants all day. 

It quickly became an exhausting schedule. 

But I was good at the work. After less than a year, I was promoted with a modest bump in pay and given more responsibility. At the same time, I had completed the rounds of edits on my manuscript and submitted back to my agent, anxious for a response. But months would pass before I would hear anything. 

Around that time, I started to finally do my research on book publishing, now that the dream of it was perhaps, slowly becoming a reality. My findings did not fill me with hope. It was incredibly challenging to become a successful published writer, and to make a career of it. Many working writers also taught, or wrote regularly for journals, or suffered through endless self-promotion, in order to scrap together a living that didn’t involve being on the edge of poverty. It began to dawn on me that writing – even if my manuscript did manage to get published – would be a long and difficult career path. And nonprofit work no longer aligned with where I wanted to be. Everything I wanted in life – a home in a safe neighborhood, a marriage, children, travel – would take more money than I could ever see myself making at a nonprofit, unless I wanted to become my boss, or my boss’s boss, which I didn’t. I knew, finally, and with some certainty, that I needed to rethink the path I was on. But I had no idea what I wanted to do.

Launching a business

It was around that time that I attended a workshop called “Building Your Brand.” I didn’t fully understand what a personal brand was, or what I needed one for, or what I wanted mine to be, but – lost as I was – I hoped it would provide some spark of inspiration. At one point during the workshop, we all went around the room and said why we were there, and what we hoped to get out of the session. The room was filled with mostly women, mostly in our 20s and 30s. We were there for different reasons, many to launch a new business, or to get help marketing their current one. The women there inspired me. They were cool, interesting. They worked at tech and marketing companies and (I was sure) could afford both their rent and soy lattes every day of the week. I had been playing around with an idea of starting an online secondhand clothing store – I’d developed a knack for finding treasures at thrift stores after years of being broke. When it was my turn to speak, I shared my idea with the group. As it turned out, another woman had a similar idea, though she wanted to focus on the plus-size women’s market, noting a dearth in the industry. 

I found this woman (we’ll call her Jess) beautiful and interesting – she was bubbly and obsessively girly in a way few women in my life were (if I could describe my community writ large at the time, I’d describe them as pissed off feminists). I’d soon realize that we were two very different people, but in that moment she was exciting to me. Within just a few weeks, we’d decided to launch separate businesses catering to slightly different markets and rented a huge loft space that we shared to run our businesses – the price tag of which gave me daily anxiety. 

It’s hard to describe this time in my life. I was equally enthralled as I was terrified. Friends were excited for me, though surely they questioned what on earth I was doing. My boyfriend, also an entrepreneur running his own recording studio, loved the idea. I had one foot still in my daily 9-5 nonprofit work, one foot figuring out how to run a business, and one additional limb holding out hope that my agent would soon call me to tell me she loved the edits to my manuscript and she’d sold my book to the highest bidder so that I could say goodbye to all of this and just write. 

It soon became apparent that the businesses Jess and I were attempting to run were more or less the same thing. Instead of attempting this awkward competitive feat, we decided to become business partners. Soon after, we launched And We Evolve, an online secondhand store for women, run out of our huge, drafty, dusty loft. I was a new business co-owner, but with no planned profits in the near-term, I needed to continue my full-time job. My weeks were dedicated to the nonprofit, and my weekends were devoted to sorting through donated clothes, building a business plan, and maintaining our business website, something I knew very little about.

The business work was exciting. I dove into learning more about what made for successful brands, how to take and edit product photos, and web design. I loved this side of the work, and surprised myself with how quickly I could learn. I started studying Photoshop and Squarespace, and took and edited all of the photos of my friends who I made model for me. I no longer had time to write, but I was okay with it. I needed the break from thinking about my manuscript, and was excited by the challenge of this new venture.

But my weeks dragged. It was becoming more and more difficult to manage the work of the business – mostly, the work of planning and building the business, as we were not yet receiving many orders – with my nonprofit work. To add to my schedule, I had agreed to take on a grant writing contract with another organization in order to cover the extra costs I was putting into the business. I don’t know how many hours I was working during those months, but I felt like I was running on a hamster wheel with no clear expectation for relief. 

At the same time, Jess, a PR whiz, was getting us press. We were profiled in a local environmental magazine and soon after, the Philadelphia Inquirer. I had to feign illness at my nonprofit job to make sure I was at the studio to meet the journalist coming to interview us and take photos of the clothes. We’d pivoted from an online store to a subscription-based clothing box filled with secondhand clothes. We’d gained a steady customer base and were finally making enough to cover our expenses, which had grown precipitously with the switch in business model. During all of this, somehow, a producer from Shark Tank reached out to us. I should have been excited, but I was more overwhelmed and stressed than I’d ever been. 

Reaching a breaking point

Life was beginning to pass by me. I honestly don’t know when I even saw my boyfriend or friends during that time, my days just felt like an endless loop of work and more work. I was still barely making enough money to get by, and all of the extra money I had went into the business. The summer came, and so did the submission of paperwork and a video to the Shark Tank producers. Jess and I had three interns, but fissures in our own tenuous relationship were beginning to form. We had different work styles, different ways of thinking about money, and crucially, our business was her full time job. While I scrounged to put in 12-15 hours of work per week on the business, she was spending all of her time thinking about and working on it, something I had no way of committing to. The imbalance was apparent to both of us. We were beginning to argue, and I felt myself waking up in the middle of the night with a pressure forming in the middle of my chest and my mind racing. I was constantly anxious in a way I had never experienced before. I knew something had to give, but felt completely trapped. If I gave an inch anywhere, it felt like everything would fall apart. 

By the middle of the summer, things came to a head. Stress had made me miserable and negative. Each morning felt like the start of another marathon. I was struggling to focus at work because I was always thinking about the business, which began to creep more and more into my days. I knew nonprofit work wasn’t anything I was passionate about or saw myself doing in the long-term. With the extra money from the grant contract, I had saved just enough to survive on for three months. The contract was soon ending, but I was hopeful I could renew it, though I had no idea if I’d be able to. I started to talk to my boyfriend about quitting my job. He encouraged me to stay until the end of the year, but as soon as he suggested it, I felt in my bones there was no way I could. Six more months of the level of stress I was experiencing felt completely impossible. 

The next week, I gave two-weeks ' notice. It was July, and if I hadn’t been so blinded by the relief, I would have been terrified. But luck was on my side: my grant contract was renewed, and it led to another one, which offered me the same amount of money I was making at the nonprofit working full-time. I could now devote full days to And We Evolve.

But not everything was perfect. Almost as soon as I left my job, my agent came back to say she wanted to shop around my novel after passing it through diversity readers, which I had to pay for. Another thing was back on my plate, and I once again felt pulled in multiple life directions. While I was able to dedicate more time to the business, it meant that Jess and I were spending more time together, but the tension between us was growing only more palpable. Our differing views on business decisions and work styles had not landed on compromise, and while I was able to breathe a bit more, finally, the anxiety and stress did not relent. 

We found out we were not selected for Shark Tank sometime in late summer. I was secretly relieved; we were still just getting by, though our customer base had remained steady. Getting ripped apart in front of Mark Cuban and a million viewers had haunted me for weeks. 

Throughout the end of summer and early fall, Jess and I walked on eggshells around each other, and I began to wonder if our business was viable. We both dreamed of being wealthy, both hungry for the freedom of lasting financial security, but to me, it began to feel more like a fading dream than anything tangible. By November, just over a year since we’d launched, a bitter argument led to my decision to leave the business and end my relationship with Jess. We couldn’t reconcile our differing views, and I had lost faith in And We Evolve’s success. After a few more strained weeks of tension and paperwork-signing, I was officially out. Soon after, my stress began to calm, my anxiety, at last, lifted. 

Making the change

I now had decisions to make, and time – that rare, glorious gift – to make them. I left And We Evolve with a newfound love for web design and branding. I had heard of people moving into tech from other fields, but had no idea how my scattered work history could translate into it. I began asking around, connecting with anyone who would talk to me, to learn about what tech work was like, what roles could be available to me, and what I should do to get them. At the same time, I managed to secure more grant contracts, a few of them long-term, which allowed me to really focus on my next step. 

In January 2019, I enrolled in Thinkful, a tech bootcamp, and began on a path to learn UX design. While maintaining my grant contracts, I began building Squarespace websites for my friends for free, developing a portfolio. I met with a UX design mentor twice per week, built a resume, and began practicing how to speak to my past work history in a way that felt relevant to my new career. By August, I had completed the program, as well as most of my grant contracts. The money I made as a contractor afforded me the ability to take the full month of September off while I focused on getting a job in my new field. My boyfriend and I took two weeks off to travel to Europe for a friend’s wedding, and by the end of the month, I had two job offers. On October 7, 2019, I started my first day as a UX Strategist with a small, quirky agency based in Philly. I loved it, and thanked the universe every day that I landed where I had. 

At some point my agent came back. She couldn’t get publishers to bite. She suggested I start another novel. But by that time my life had gone in a different direction. I no longer wanted to have a career as a published writer. I was happy doing something entirely different.

After two years at the agency, I moved into a UX Strategist position at a larger corporation that offered enough money to give me the financial freedom I’d been craving for years. My boyfriend and I could now afford to get married, plan for a child and a new home out of our construction-ridden neighborhood, and travel: everything we wanted. 

Some days I could cry with how grateful I am to be where I am, to have made the decisions I’ve made, to have fallen apart and to have figured out how to pick myself back up. Of course, there are choices I wish I had made, things I wish I’d done differently. In another life, I could have gotten to this point much sooner, could have perhaps saved myself years of struggle. 

Or maybe not. Maybe everything needed to happen in just the way it happened for me to be where I am now. Either way, I will never doubt my own capacity to know when things aren’t working out, and to change. Trusting in myself is what got me here, and it’s what will carry me through the next chapter of my life.