Technically, the date on my Bachelor of Arts degree is January 19th, 2018. This unique date is thanks to the one winter-term class I still needed to complete my degree. I wasn’t really ready to be done with school then, though; I just figured that having the degree in my hands as soon as possible made the most sense. Given my feelings of uncertainty, I decided to enroll part-time in school one more semester after graduating and tack on a post-baccalaureate minor to give myself some time to think and adjust. My official last day as a student at UWM would be Friday, May 18th.
Fast-forward to fall of that year and I was feeling a little miserable and a LOT confused. The Geographic Information Systems (GIS) internship I had accepted with the county government back in March was both boring me to wits end and overwhelming me with projects I could barely understand, let alone complete. Studying geography in school had given me a sense of direction, but I wasn’t sure this was it. I was also constantly daydreaming about and distracted by a little blog I’d recently started called The Wisconsinista…
The corporate-style office I worked in had no windows, no real place to eat lunch, and was right in the heart of an unsafe part of downtown. I felt too afraid to go outside for even a brief break and especially dreaded the beginning and end of the day, when I had to walk twenty minutes through the “tent city” homeless community under the freeway on my own to get to and from the one place I could park for free. The environment was all wrong for me, but I wasn’t sure what was right. Finally, the week before Christmas, I gave my notice, with nothing but ambiguity ahead.
Making Bad Decisions
As the ball dropped to signal the start of 2019, I began my first year off-script. For the first time in my life, I didn’t have school or a job, and it felt like I had made a blatantly stupid decision. At the same time, I kind of LOVED that I’d finally made a conventionally “stupid decision” for once and tried to give myself the opportunity to slow down and enjoy this liberating season of rest. I started publishing blog posts each week and tried my hand at some “influencer collaborations.” I took some online graduate classes in marketing through a nearby university and casually applied to fun-sounding jobs like “junior stylist” and “professional water skier.” I had so many options… but deciding where to start proved the most overwhelming.
I always feel like winter is a great time to take time off in Wisconsin though, because for some reason the cold weather deems it okay to slow down, stay inside, and go days without doing anything productive. To be fair, I was working this entire time, but at my own pace and for my own endeavors, knowing I likely wouldn’t have a dime to show for it for months. I was teaching myself WordPress, learning how to use a real camera, trying to connect with other bloggers to shoot content, and ignoring the voice in my head that kept reminding me I needed to make some money eventually.
Those first few months were messy and there were plenty of days where I looked at myself in three-day-old pajamas feeling lazy and like a failure. I had promised my dad I’d start paying for my own car insurance in 2019, but ended up asking him to cover one more year in leu of getting me any birthday or holiday presents instead. I sat at home almost every day, sometimes crying and sometimes sleeping in, but always grinding away at my goals. I decided that I wanted to get back in the work force, but only for the right position…
In mid-February, I was feeling unsure about what direction my career should take but didn’t want a big gap on my resume. Naturally, I did what any desperately unemployed person would do and I reached out to my former employer from the one job I truly did love to see if they could use me back. I started working on the docks for a boat tour company the summer after my freshman year of college and fell in love with it (and, subsequently, the tourism industry), but it was the office manager position I was really after. I started working in the office in June of 2016 and never looked back. Why get an internship when I could wear a hundred hats at a small business doing work I loved?
I was eagerly welcomed back and started popping in the office a few hours each week to answer voicemails and emails, as well as get the office ready for the upcoming season. As a senior staff member, I had the perks of making my own schedule and being trusted to work independently. I knew how things worked, got my tasks done efficiently, and was respected. I also trained new office staff and got to manage the company’s Instagram account. I loved the familiarity and reminded myself that this was proof that I could find a job I loved going to long-term if I searched hard enough.
That was pretty much my summer. It was perfect. I worked anywhere between 20-35 hours per week, got to water ski on two different teams, and had plenty of time to work on The Wisconsinista, not to mention that my social media and WordPress skillset was gradually expanding. I knew the magic would end on September 30th with the completion of the boating season, so I made the most of having money in my bank account and enjoying one more season at my favorite place.
Wake Me Up When September Ends
As the show ski season ended and my 24th birthday approached, the end of my seasonal employment also loomed in front of me. I’d already started applying to various positions that I thought offered the potential to be a good fit, but hadn’t heard anything back except for a few rejections. Some positions I saw posted on LinkedIn looked amazing, but I didn’t apply because I saw that they received hundreds of applications within a single day! Those were mostly the marketing and social media ones. My new fear was how I’d ever outshine the competition when I didn’t have a marketing degree, even though I’d grown my own brand by over 1,000 followers and learned a lot during my first year blogging.
In a panic, I applied to some positions that weren’t such a great fit, including one GIS position that I knew my degree and previous work experience qualified me for. Sure enough, I heard back with an offer and was given three days to accept or decline. That was definitely not enough time for me to make such an important decision, but they weren’t willing to extend my response time any longer. I eventually accepted with regret (don’t you wish that was an option on wedding RSVPs?). Literally a day later, I was invited on my first paid travel writing job and could not have felt like the timing of my acceptance of the corporate job was more wrong.
Within a week of training, my initiative and productivity had tanked. I couldn’t believe I had voluntarily let myself take another job doing technical computer work. I couldn’t wrap my head around all the utilities terminology I needed to learn to be successful and was quite frankly stressed out about the limited time I now had to work on my blog. I thought about the Instagram post I had shared on January 1st about my decision to live adventurously and realized that if I didn’t leave now, I couldn’t make a post on the first day of 2020 saying I had learned anything from my year off. I debated whether to stick it out until I absolutely couldn’t go another day, but realized that still wouldn’t have been long enough to put the position proudly on my resume. With that realization, it made no sense to stay, so I didn’t.
So here I am, unemployed again as I enter 2020. I’m excited because I’ve had two awesome paid partnerships so far, one being a northwoods Wisconsin destination and the other being one of my favorite hotels, and know that with adequate time to devote to The Wisconsinista, more meaningful opportunities may come my way. I’m also terrified; in just a year and a half, I legally won’t be allowed to stay on my dad’s health insurance. I either have to work for an employer who offers it (read: full-time and corporate), marry Tyler and pay him for my share of his work insurance (neither of us feels that marriage is necessarily the right choice for us), join a union (not sure if there even is one that’s relevant to my line of freelance work), or pay a heck of a lot for my own marketplace plan.
Influencer and blogger work also comes with its own share of financial confusion and I am dreading the math I’ll need to do to figure out how much I owe in taxes for this year. With freelance work, taxes usually aren’t taken out ahead of time like they are with a full-time employer, so setting aside money for that, as well as an additional self-employment tax, is critical. I also have a ton of loose ends from starting and stopping so many jobs, side-hustling, and receiving PR gifts from companies (Yes, those are taxable. So are giveaway prizes. So no, I don’t plan to host any and I definitely won’t be entering any)!
I have a few adventures planned during winter (click here for tips to explore more for less), but I think I might have an idea for my next step. I’m going to start applying for jobs again soon, but they won’t be full-time unless it truly is something I’d want to do more than blog. I’m envisioning a front desk customer service position at a chamber of commerce, convention & visitors bureau, or a medical clinic. I’d work regular hours and spend my days helping people. I might not be rich, but if you don’t play that hard, you don’t have to work as hard. Believe me, though, I’ll still be giving it everything I’ve got.