Five Lessons Learned from Failure


2017 was the year I’d been dreading since 2007. I wanted to line my adolescent gray skies with adulthood silver linings—professional accomplishments, a passport full of exotic stamps, success. Wholly unoriginal, I understand that, but I wanted to be something worth being.

Ten years ago, I set off to college full of ambition and excitement for the future. I worked hard, did relatively well, and graduated magna cum laude four years later, but I don’t remember being full of ambition or excitement afterwards. Hesitation, anxiety, and confusion were my guide posts. I needed to find a job, preferably a career, but I had no idea where to begin (with a BA in English Literature, opportunities weren’t exactly blinking neon signs screaming, “This way!”). I moved back home, as per the millennial stereotype, and started searching for jobs. Instead, what I found was more anxiety and fear.

It always bothered me that I never knew what I wanted to do with my life. That uncertainty felt as much like failure as anything else could have. I remember a formative night from my childhood, laying in bed after a tough day of sixth grade, staring at my closet doors that looked like monster eyes and thinking to myself, “I have no idea what I want to be when I grow up.”

The next six years would be a continuous slog of failures and false starts, and only now can I look back at what I learned in the process.

Lesson #1: Learn when to stick it out and when to call it quits.

Post-grad life saw me back at my family-owned bookstore in Mississippi simultaneously planning my wedding and future. Two days before the ceremony, I interviewed for a social media marketer position at a tech start-up. They told me to show up the Monday after the honeymoon. Relief.

The job was both hard and simple. Once I learned the ropes, it was an easy gig, but there was an undeniable high school vibe.

The start-up was basically a social media marketing company, which they would not appreciate me saying. They built their own technology for us writers to use in our day-to-day work, so my skill set and experience narrowed, limiting my transferable skills. Most people only lasted a few months before they moved on to a different job. I stayed for my mentor.

An opportunity fell from the heavens for my husband, which meant relocation. I offered to continue working, as they were understaffed, and I felt like it could be a symbiotic relationship—the continued benefit of a steady paycheck for me and much needed help for them. It seemed logical and the job was social media, totally online, and therefore, perfect as a long-distance job, right?

I worked remotely for about a year, traveling from Memphis, TN to Jackson, MS once a month, every month. I would stay with my best friend at the company (my aforementioned mentor) and work on location for a couple of days. That was one of the most tiring years of my life, and at some undefinable moment—maybe it was several moments that gathered together like dust—I stopped going the extra mile. I didn’t quit, but I stopped caring. I was doing the bare minimum. I hated my job, and it bled into my ever aspect of my life.

On one of my last trips to work onsite, I had a bad feeling, a premonition of sorts. My mentor and I stopped at a drugstore to get candy for our afterwork movie marathon, and I noticed she was being weird and uncomfortable. When we were about to checkout with our embarrassing amount of junk food, she told me she’d cover the cost. It wasn’t out of the ordinary for her to be thoughtful and giving, but something was off. We walked outside, got in her car, and she finally blurted out, “The boss told me that you either have to move back to Jackson and work in the office full-time, or we have to let you go.”

She felt so guilty, but honestly, I was relieved. I knew we weren’t moving back to Jackson, and I told her as much. That would be like taking steps backwards; despite my locational hurdles, there was simply no future for me at the company.

That was that. I gave my two weeks notice the next day. I didn’t say goodbye, and no one noticed.

I slogged it out in that job for over two years. Between the slightly hostile work environment and the limited opportunities for career and skill growth, I realized too late that there were many times when I should’ve just called it quits.

Lesson #2: Stop doing the same thing and expecting different results.

After my experience at the tech start-up, I found a job as digital media director at a small property development firm in Memphis. The role was fine, and the company was great. As a one-person department, I was wholly autonomous, which was amazing. Though I didn’t love what I was doing, I liked where I was. I no longer had one foot stuck in Mississippi with the other in Memphis, so I was able to actually become immersed in this new place that I had barely noticed. As soon as we started to feel settled though, my husband was offered another job.

This one took us to California.

We packed up, and moved our butts 2,000 miles away. I. was. pissed. My resume already looked like a jigsaw puzzle of wonky timelines. What was I going to do in a tiny city in California?

As it turns out, not much.

For my professional career, California has been a nightmarish rollercoaster ride. I was jobless for 4 months.

Since I couldn’t find any job I considered worthwhile in the long run, I started volunteering my social media services to a museum part-time. Hoping it would turn into an actual opportunity, I put my all into it. In retrospect, it seems obvious what my mom was trying to tell me, “Ashlee, why would they start paying you to do what you’re already doing for free?” I don’t know, Mom, because they like me? Not enough, apparently.

The moving around caused the job hopping, but the uncertainty and insecurity I was feeling caused me to keep applying and accepting the same job: social media marketing. I hated it, but since I had been doing it for my entire career thus far, I thought I might as well continue down that path. Every time, I thought to myself: it’s not me; it’s the job.

But as I reflect, it’s clear that I was simply doing the same thing and expecting different results.

Lesson #3: Go where you’re valued.

In an effort to switch gears on my career, I found an opening for a temporary-to-hire technical writer position at an engineering firm a few months later. When I interviewed, I asked my interviewers, “What’s your favorite thing about working here?” to which they all replied, “The people, definitely. It’s like one big family.” I guess that should’ve been a tip-off—family doesn’t always equal happy (or even friendly).

It didn’t take long for me to learn that this “big family” didn’t really have room for any more members. I was like the unexpected little sister nobody wanted. Though I was part of the marketing department, my cubicle was in the accounting/finance department, which I soon found out was the bitchiest group of meanies in the whole company. I was one of the youngest people there, and part of my job was to perform copywriting and editing duties. Taking initiative, I decided to do an audit of the company’s social marketing and create a strategy for them as a side task in my free time. Once I had everything perfected and finalized, I emailed a 10-page PDF chockfull of charts, analytics, and ideas to my boss. I never heard anything about it.

That is, until a couple of weeks later.

Apparently, during that time, one of my accounting neighbors had noticed that I was on social media and complained (read: tattled) to her supervisor. Something was mentioned about my “inappropriate use of time” and how I was on “social media for whole work days”. This supervisor then relayed that message to mine.

My boss knew I was on the company’s social media since I had turned in my report, but it was still an embarrassment for her.

Everything went downhill from there.

By this time, I had been at the company for a couple of months. My hiring date coincided, in fact, with the height of their annual nonprofit fundraiser—a drive-thru dinner where the proceeds go to a good cause. Everyone in the company was given ten tickets to sell, and though it was not required, it was highly frowned upon if you didn’t sell your tickets. Since we don’t know anyone the area, my husband and I decided we’d buy all ten and donate the dinners to the veterans’ center. $400 for a good cause and ten tummies fed seems selfless; since I had to move those tickets regardless, buying them all was the easiest, albeit, most expensive option.

I signed up, showed up, and peddled the shit out of that fundraiser at minor league baseball games, farmers’ markets, and Saturday morning marathons.

But sadly, it wasn’t enough.

I was “let go” the following Wednesday. Citing money issues, though legitimate, were not a consolation. My boss apologized, claimed mortification because I was guaranteed a position until the end of December, but they didn’t expect the recent downturn in business, and my position was precarious — recent hire, a temp, and in the lowliest department.

I thanked my boss for the opportunity, went to my tiny cubicle, grabbed my shit, went outside, and called my mom. I didn’t cry until I got home.

After I was laid off, I caught myself taking inventory of all my jobs, and this Richard Branson mantra gave me hope for a job that would value my contributions:

Clients do not come first. Employees come first. If you take care of your employees, they will take care of the client.

To be valued in a job is not something I’ve experienced. Maybe it’s entitlement, but I want my skills to be appreciated or at the very least, noticed. It’s a dog-eat-dog world, I know that, but if I’m not valued where I work, how do I continue to be valuable?

Lesson #4: Sometimes the problem is you, and sometimes the problem is your approach to the problem.

At this point, I’m starting to wonder what my problem is. Maybe, I internally panicked, I’m Taylor Swift but, instead of a revolving door of boyfriends, I have strings of unsuccessful jobs.

Over the last few months, as a way to manage stress and anxiety, I returned to my love of calligraphy. Attending workshops and classes, I found myself lightly networking without even realizing it; then, almost inexplicably, I started freelancing as a pointed pen calligrapher for a local graphic designer. It was a crazy scary step for me. There were some growing pains and embarrassing photos of my work in its beginner stages but wholly worth it.

Not only was I not getting paid to do this though, it was costing me. Paying for supplies and traveling to styled shoots ain’t cheap, so I did the unthinkable. I offered my social media services to the graphic designer. My thought process was logical, if not seriously flawed. If I could do her social media and get paid, then I could fund the calligraphy.

This designer was my lifeline into the local creative community, so it was imperative our relationship stay amicable. I offered up to ten hours of work per week for $10 an hour. In California, that’s peanuts. Hell, that’s barely worthwhile anywhere. Because I lacked confidence and maturity, I didn’t have the courage to ask for, in my opinion, fair compensation. As a result, I quickly began feeling overworked and underpaid. This is failure on my part. I’ve made this mistake, in some form or another, for the last few years. At some point, I had to admit I was the common denominator. No, the problem wasn’t every single job. The problem was me. I kept doing the same thing and expecting different results.

The definition of insanity. Or stupidity, depending on who you ask.

It took me three months to summon the courage, but I was determined to begin 2017 with a fresh slate. I didn’t want to lose her as a connection to the calligraphy community or ruin our professional relationship, but in the long run, I knew it was worth the risk. On January 2, 2017, I emailed my letter of resignation.

She gladly accepted it. I think she was relieved to have control back in her hands and me out of her hair.

The problem, I’ve realized, is not the job. The problem is me. I’m the one who keeps taking the same job and expecting different results like an insane person. It is me who chose to pursue something that knowingly made me unhappy. I refused to change while simultaneously expecting change for the better to occur.

Lesson #5: Change will happen when you do.

It was around this same time that I realized I was trapped in this vicious cycle of doing things out of self-placed expectations without really assessing the consequences. Why did I keep making the same mistakes? My driving fear, and therefore biggest motivator, was being aimless and jobless.

We’re fed this bullshit line when we’re kids to find what we love, so we can find a career. If we just follow our dreams and passions, we’ll find happiness. It scarred me. I didn’t have a dream career, and it took me twenty-five years to find my calligraphy passion. What’s a grown-ass woman to do?

Since mid-December, I have been learning to code. I decided to pursue front-end web development like it’s my job. It’s difficult, frustrating, and humbling, but this is the path I’ve chosen. No longer shackling my self-worth to my professional success, I have seen my calligraphy featured on Green Wedding Shoes, rejected a job opportunity that would have been another dead-end hell-scape, written a featured article about an esteemed LA-based artist, and taken the time to actually enjoy California.

Ten years from now, I’ll look back on this as the year things changed for the better; the year I found something worth being: happy (and preferably employed).