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A very long summary of how it took a 34 year old millennial to finally get a handle on money


It’s been 11 years since I graduated from college and today I am $2,900 away from being freed from the chains of my monthly student loan payment. With pure curiosity, I recently decided to look back at how many of those years I’d actually been actively paying on my loans and how many years I chose to defer. In case you were ever interested, here is a very long summary of how it took a 34 year-old millennial to finally get a handle on money by way of 30+ jobs.


It's 2008 and I'm newly equipped with a Bachelor of Arts in International Studies. I knew that I wanted to get out of Wisconsin, so I applied to jobs at nearly every international humanitarian NGO and national non-profit around the country.


0% called me for an interview.


I eventually got an in-person interview in Arizona with a for-profit study abroad company. After being interviewed in a ranch-style-home-converted-to-an-office in the middle of a suburban subdivision, being told that the bulk of my day would be managing inbound and outbound calls from prospective students, and telling them that my least favorite part of the job would be managing inbound and outbound calls from prospective students, we were both convinced that I was not the right person for the job. Although, I was especially convinced when our interview took place in the kitchen and my would-be office was the spare bedroom.


I then got two interviews with Rotary International in Evanston, Illinois – but was told that I was a bit overqualified for the position and they didn’t think it would keep me satisfied. I don’t know how a 22 year-old with a month old bachelor’s degree can already be overqualified for a job that has a minimum requirement of a bachelor’s degree, but I accepted the denial email and trudged onward.


Unemployed and a bit confused by my lack of immediate success (I mean, I got the elusive degree – where’s my elusive job already?), I walked down the street from my apartment and got a job as a full-time server at an Irish pub. I don’t eat meat, drink liquor, or wear green on St. Paddy’s Day, but I needed the money and it took me 45 seconds to go from my door to their door.


After nearly a year of slinging bangers and mash and all of the whiskey, I secured a new job at the public university down the street. I put away my apron, cheerfully said goodbye to panicked dreams about missing straws and silverware, and went back into a more comfortable world – academia.


When five years of academia doesn’t pay off for you professionally, it’s best to go back and spend more time there supporting other students through this same journey. I did end up loving it though. As an AmeriCorps*VISTA (read: government volunteer program participant with an $800/month stipend and the ability to apply for food stamps), I worked on campus helping students find meaningful volunteer and work-study opportunities. A perk of government service – public loan deferment for a year. Let that loan interest accrue! Of course, I still managed to treat myself to a week-long trip to Costa Rica while living below the poverty line. Questionable life decisions.



I loved this line of work so much that I decided to go and get my masters so that I could pursue this career field full-time, but with an actual salary and benefits. Fortunately that particular graduate program is typically very generous with tuition reimbursement tied to a graduate assistantship, so I didn’t have to go into further debt for an added M.Ed in my email signature (never even did it anyway, and I’ve learned that scientists with BioTech PhDs aren’t super impressed with my competency-based education education graduate degree).


…and now let that interest accrue while I go to grad school for two years, too! With no program expenses and several larger merit scholarships, you’d think I’d have either started to pay off my undergrad loans or put it in a savings account. But no, I used it all and then took out an additional $5,000 of federal loans, just in case.


What you think grad school is going to be like...

What grad school is actually like.

After graduating from OSU, I moved back to Milwaukee and accepted my first big girl gig with Marquette University as an administrator coordinating service learning opportunities. I immediately signed up for the income-based repayment plan, as well as the Public Service Loan Forgiveness program since I was working in one of the approved areas on campus. 10 years of consistent public service and my loans would be forgiven, they said. (99% of applicants have been denied forgiveness as of last month, so it's not looking too promising for anyone right about now).


Unfortunately, since this was my first salaried job, I didn't quite know how much would be taken out for taxes every paycheck, I signed on for a East side one-bedroom lease that was about $500 more than I could realistically afford. To cover for this expensive mistake, I worked two part-time retail jobs, one being where I met Nick and the other where I fell in love with powervita fabric exercise leggings (and then spent all of my would-be additional earnings on such leggings).


Likely being super helpful.

Welp, two years later I left Marquette to teach English in rural Japan through the JET program, so I went ahead and put those federal loans back on deferment for 12 more months. I did keep paying on my private loan for all of this time and also cash flowed big trips to Thailand, China, and India during that year abroad. JET is one of, if not the best paying programs in the world for teaching English abroad. I made great money, had very few living expenses, and was able to put away a nice $7,000 nest egg even with the weekend travel trips.


JET: 365 days of peace signs

What did I do when I returned from Japan? Went back to academia and got another graduate degree, this time in Nonprofit Management (an even more lucrative field than higher education administration!). Again, I lucked out and got it paid for through an on-campus assistantship and some scholarships, and again, put my federal loans on deferment…but boy oh boy, I sure was committed to never making money, getting out of debt, or starting a career. This time though, I didn’t take out a single dollar of additional loan funding to cover living expenses, so let’s call that progress.



Now outfitted with three college degrees (three too many based on my current job which requires only a high school diploma), I accepted a job doing fundraising for a private, Catholic school – another position which landed me back in the Public Service Loan Forgiveness program. Back to income-based repayments and back to the hopes that it would all be forgiven in 10 years (it wouldn't be, for me or 99% of applicants).


Work: A collection of school photos and name badges

Unfortunately, this work environment (read: leadership/management style) ended up proving far too toxic for any human being with feelings and a functional amygdala, so I sobbed myself silly, gave Milwaukee the middle finger, and moved down to Austin, Texas for a fresh new start.


New city, new apartment, no furniture

Whatever I had just attempted to save from the last year of work was spent on covering my moving expenses to get to Austin ($3,000), but I thought it would be worth it as I was getting an $11,000 boost in salary with the new non-profit fundraising position. Surprise, a warm, liberal, quickly growing tech hub city (adding +120 people each day) with a major university is more expensive than the shrinking Midwestern city of Milwaukee, Wisconsin. But, with my increased salary and two retail jobs, I ended up putting away $15,000 in savings, continued to chip away at my student loan debt, and even managed to enjoy a week of vacation in Belize.



Unfortunately, while I was getting a handle on my finances for the very first time, my partner was not so lucky. His first job in Austin involved a painfully long interstate commute (or as it’s called in Austin, “driving”) so he transitioned into a new commission-only job down the street that netted next to nothing. He continued to ride the struggle bus for as long as he could, but eventually gave up on Austin, called it quits with me, and moved back to Wisconsin to be closer to family, but that’s another story for another day.


Once I realized living in Austin by myself was going to be nearly financially unfeasible for me (our $1,300 one bedroom apartment was going to suck my savings dry in a matter of months), I started to look at more affordable states and cities…until Nick apologized and I quite reluctantly said yes to moving to be with him in Madison, Wisconsin.


Fine, I love you enough to move back to winter

If you haven’t caught on by now, Wisconsinites like to leave Wisconsin, but always seem to boomerang their way back to the good land to settle down, no matter how hard they try not to. It’s the curse of the deep fried breaded cheese and Friday night fish fry’s.


If anyone is actually still following along with this, you’re almost there. You’ve got this! Present day life is just a few thoughts away. I told you I’m incapable of being succinct or brief.


Have you ever thought, “You know, I never wanted to know every single thought Courtney Nikolay has ever had on any given topic, but now that it’s all in writing, I’ll take a quick gander at the madness!”?


What’s worse than spending $3,000 to move all of your things south in August 2017?


Spending $3,000 to move all of your things back north in the middle of winter (December 23, 2018) after the world’s worst break up in a moving truck with your petrified cat. Thanks, life.


Of course I didn’t make any of this any easier on myself by taking a new management job that started the morning of December 26, 2018 – and that required a $13,000 pay cut.


Am I doing this right? It doesn’t feel like I’m doing this right.


Running a boutique indoor cycling studio was never really a part of my professional plan, but if you’ve read any of this, you know there’s clearly never been a plan, so what the hell? Sure, I’ll run a fitness studio! Let’s add job number 28 to the list! General Manager, check.


The early morning hours into the late evening and weekend hours could be excruciating. Plus, the role often tested my sanity, but damnit I learned the most I have from any one job and quickly gathered what I’m really freaking good at (sales) and what I’m really freaking bad at (all forms of professional confrontation).


Although I loved the day-to-day interactions with members and staff, the time and energy I was devoting to the role just wasn’t sustainable for my psyche or my bank account for any longer than six months, which is how long I lasted.



I definitely didn’t save much during that time, but also didn’t do much of anything besides go to work, so I didn’t spend much either. Without anything else lined up, I panicked about my savings depleting in two months and took a 25-hour a week barista job at a local coffee shop making $9.50/hour plus tips.


Have you ever thought, “I’m looking for a chill, low-key job with no stress. I think being a barista would provide that for me.” Yes? Me too. Where should you probably not work if you’re looking for a chill coffee shop gig? The most popular coffee shop in town during morning opening hours.


Think you’re an intelligent human being with capacity beyond asking for drink orders? Think again.


The CPU of my brain was never quite warmed up by 5am to ask nine beverage and bagel-related follow up questions to 70 noticeably hurried people in line. When I wasn’t struggling through complicated drink orders (I still don’t truly know the main difference between how to make a cold brew or an iced coffee), I was torturing myself on the food line hoping that nobody would order anything that required me to fold an overflowing tortilla wrap or touch the smoked salmon.


I was a slightly distressed mess on the inside, but I like to think I looked confident on the outside as I delivered my 78th bacon burrito for the day. And, the paychecks ended up being pretty decent since we got to split all of the cash and credit card tips amongst ourselves, so my savings account didn’t take the big hit I was expecting. To nobody’s surprise, I lasted less than two months at the coffee shop, but would have endured it for longer had I not gotten a job offer!



Even for me, this is quite the epic, long-winded version of how I finally decided to take control of my finances at 34 years-old.


Madison is a tough job market because it’s a small college town where everyone is over educated and overqualified and there are really only three main industries: education, insurance, and healthcare. I wasn’t really looking to get into any of these fields, so I applied for an administrative job at the BioTech company a mile down the street from my apartment and happily accepted their offer a few weeks later.


With a few detours, I’m back up to the salary I enjoyed in Austin, but in a city with a lower cost of living, and much to my enjoyment, with a far less demanding, less stressful job.


This summer while I worried about whether I'd ever get hired on again for gainful employment, I watched lots of documentaries and videos about minimalism. Admittedly, I wasn't much of a collector, hoarder, or clutter creator to begin with, but I had enough stuff sitting in my drawers, closets, and boxes to make an extra $1,600 through Poshmark, Mercari, and Facebook Marketplace sales. Between selling off my stuff, following a strict budget where every extra dollar earned immediately goes to my loan debt, and picking up side gigs like dog walking and virtual assistant-ing, I've been able to make some progress with my personal finances (detailed breakdown in a blog is coming).


Am I starting to do this right? It feels like I’m starting to do things right.

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