Random Jobs I’ve Had

I had a reader ask me months ago to either do a video or blog post about the jobs that I had and how I got them. Well, I was so busy having three jobs, that I never got around to doing it. I figured now would be fun to talk about a few of the (MANY) jobs I’ve had and how they came about…

First Job (besides babysitting like everyone else): McDonalds (~3 years)
MCDs was the place to be in high school – at least we thought so. I was in cheerleading, volleyball and dance team + academic clubs in HS and they were in the only employer in my tiny, tiny town that worked around my schedule.

How did I get the job?  I got the job because a friend’s mom was a manager there and she brought me on board.

College Jobs: Waitressing + Internships
I put this all in one category because I had multiple jobs (Me? Multiple Jobs? Imagine that!) throughout my four years at college. On campus I worked in Facilities (for a very short period of time), Career Services (my fave) and Housing (on-campus internship). Off campus I waitressed at two different restaurants (not at the same time) and had an internship with a healthcare company in Green Bay, which is where I found my love for marketing and events. Don’t get me wrong, college was great … but I figured out what I wanted to do because of that internship, so I’m very grateful for it. Oh, and I worked one Black Friday at Charlotte Russe before quitting and swearing off retail (or so I thought). I had at least two jobs almost all four years of college.

How did I get the job?  Normal applications

In Between: Waitressing + Retail
It took me a good six months to find a real job out of college, so I worked at Express (hated it) and a restaurant in Milwaukee until I found my full-time job.

How did I get the job?  Waitressing job – Twitter. Seriously. I reached out to the restaurant via Twitter and they replied asking me to come in. Retail job – through a friend that worked there.

First “Big Girl” Job: Marketing Internship turned Marketing Specialist (~1 year)
My first job out of college was a full-time marketing internship with a marketing research group in Milwaukee. About a month in, I was promoted to Marketing Specialist. I wrote sales proposals, made binders, worked in our CRM program, etc. Basically anything our account executives needed. It was a good job right out of college and I met some really fun people (plus I got to work with my friend Gina for a couple months) but really, I was bored out of my mind. Most days I would sit almost the whole day with nothing to do and it drove me crazy! I’m a very efficient and hard worker, so that’s just not the way I work.

How did I get the job?  Online job search.

First Agency Job: Public Relations Account Assistant (~6 months)
And then I landed my first agency job … two miles from my other job! 😉 I actually was offered two different jobs at the same time – one in Milwaukee and one in Madison. My boyfriend at the time was living in MKE and I wanted to stay near him, so I picked up this job. I had no intention of only staying at this job for a short amount of time, but another opportunity came around.

How did I get the job? Online job search.

Second Agency Job: Account Coordinator –> Assistant Account Executive (~2.5 years)
I learned SO much from this job plus met my best friend Saige, so although it was one of the most high stress jobs I’ve ever had, I did like it a lot. Mainly I worked on project/client management and social media. I actually miss quite a few parts from that job!

Saige and I

How did I get the job? This job I also got from Twitter. I was following a lady and she tweeted that her company was hiring. I messaged back and forth with her and she put in a good word. It helped that she was best friends with my boss-to-be. 😉

At the same time …: Leasing Agent (~2 years)
After breaking up with my boyfriend, moving out of our apartment and moving to downtown Milwaukee on my own, I picked up a job at the apartment building I was living in. Lots of perks (no free rent … but I did get a break!) and I only worked every other weekend. It was a pretty easy job and I really enjoyed it. I always thought I’d be good at real estate, so I’m happy I tried it out. I do miss that job and still wonder if I should try out real estate someday, but who knows!

How did I get the job? Facebook post. I was following my apartment’s FB page and they mentioned they were looking for someone. I called them literally 2 minutes after they put the post up. #desperate

Event Planning Job: Assistant Director of Alumni Communities (~2.5 years)
This was a major career shift for me. I had done event planning in internships and helped with events at all of my agency jobs, but this was a chance to do events full time. I loved this job at first, working for my alma mater, but soon after I started I realized it wasn’t right for me. The planning part was amazing and I wouldn’t trade that experience for the world. Plus, I met one of the best people in the world there (Brooke), so that’s worth it, too. But my manager was not trustworthy and I always felt like I was going to get stabbed in the back at any moment. I was bored 95% of the days and then would have to work long night and weekends with no time off work. Also, seeing my alma mater from this light just wasn’t the best for me. I loved going to school there, but working there was a different story. And honestly, I was bored AF in Green Bay and missed the (real) city. And I was paid an unlivable wage (even in Green Bay, where cost of living is smaller) so I had to work two part-time jobs as well. Sounds like a lot of bad things … but I really did love planning events, traveling and meeting fellow alumni. I’ll never forget that job!

Move-in week is over

How did I get the job? I was at an alumni event with two friends in Milwaukee and they mentioned they were hiring an event planner. I applied the next day and after a lonnnnnng process, was offered the job.

Part Time Jobs: Front Desk Rep and Social Media Manager (~2 years and 6 months, respectively) 
While working at the college, I waitressed for a hot minute (literally a month) before getting a job at the gym. Not only did I get a paycheck there and make some friends, that’s where I truly found my love and passion for fitness. That part-time job means so much to me and I miss the gym more than anything right now!

I also worked as a social media manager for a small agency outside of Milwaukee.  I liked this job, but it didn’t really make sense. I wrote content and found pictures for about 13-15 clients ranging from funeral homes (WHO TOLD A FUNERAL HOME THEY SHOULD HAVE AN INSTAGRAM PAGE) to denture offices to car dealerships to health clubs. I liked this job a lot (I love to write social media) but I had no contact with the clients and no input on social media strategy. Call it my ego, but that bugged me. I’d like to get back into freelance social media once I have my bearings straight here, but maybe I should just work one job for awhile? 😉


How did I get the job? Waitressing – I worked there in college so they just gave the job back to me. Gym – My friend Brooke was a spin instructor there and sent in my application for me. Social Media Manager – I found this job on Big Shoes Network (highly recommend if you’re in the Midwest or South) and they gave me the job almost immediately.

CURRENT JOB!!: Social Media Account Manager 
First time working corporate – woot woot! I’ve only been here about 2.5 weeks, but so far so good. This company is GIGANTIC and my commute is LONG, but I love being in Chicago. I love being challenged. I love (and hate) wondering every day if I know what the hell I’m doing. I miss that! I am in charge of a new social media program for one of our partners and I work with a small team (two designers, one writer) to do all of their social media and “special projects”. I’m still getting into the swing of things, but I think I’m going to like this. I’m good at working with people, being organized and I get a little bit of social media time, even though it’s not writing. I do miss planning events, but you never know what the future holds. For now, this was a wonderful choice for me AND (at almost 29) the first job I’ve had that’s paid me well. Perks of working at a well-established big corporation, I suppose. And, HELLO I’M LIVING IN CHICAGO!

chicago NYE

How did I get the job? LinkedIn. I applied for the job on LI and the recruiter called me almost immediately because, so I’m told, I was a “unicorn candidate” meaning I had everything they were looking for. I had a phone interview a few days later, then a 3-hour interview the following Monday. I completed the interview at 10 a.m. and around 1 p.m. (I was still driving back to GB) they called and offered me the job. It was INSANE.

Did you get through this whole post? If you did, you deserve a piece of candy or something. Hope you found this interesting or maybe it’ll give you some insight on how to find a job if you’re looking since social media has helped me in a lot of ways. Heck, I’ve met my wonderful BF on social too (story coming soon, I promise. He wants to help me write it – how cute is that?!)

Linking up with Amanda! 


  1. Torry says:

    It was so great to read this post. At 30 my resume looks just like yours – job to job to job and sometimes I feel like I am alone in this bc my friends have long time periods at jobs. I’m in school now for teaching and yet still not 100% sure thats where I want to end up……

    • Jessie says:

      I think that’s pretty normal for people our age. At least, most of my friends are similar. Some have stayed longer, but they found amazing jobs where they were paid well and given advancement opportunities. So far, I’ve moved for jobs with better advancement opportunities which isn’t that different from moving up within a company. Usually happens every 2-3 years. We’ll see how this job goes! 🙂

  2. Katie says:

    I am jealous of your job history! Its the types of jobs I have wanted, but haven’t had. Now I’m somewhere in the world of finance, and I don’t even like it. But it pays “okay” has some vacation, and hopefully it won’t be a forever. I wish I could have a decent idea to start my own business, but I’m not there yet.
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    • Jessie says:

      I’m with you on starting my own business. I really hope that some day I can do that full-time, or at least a solid part-time job where I could work part-time somewhere else. I crave the freedom. I’m just not made for a typical 9-5, in my opinion. But it’s working for now!

    • Jessie says:

      Twitter has helped me so much, it’s crazy! I don’t use it as much now besides to send out blog posts, but it has definitely helped me in the job and networking arena!

    • Jessie says:

      Yeah, there’s been quite a bit! Customers can be SUPER rude! If anything, those jobs taught me how NOT to be to retail or service people.

  3. Jill @ RunEatSnap says:

    I really enjoyed this post! I have a had a lot of jobs/internships over the years (and moved around a lot for them) so good to know I’m not alone! And love to see the different ways of obtaining jobs these days. Also can’t wait to read your BF story because I am 30 and starting to consider dating again. Help! 🙂
    Jill @ RunEatSnap recently posted…My Favorite Hip StretchesMy Profile

    • Jessie says:

      Thank you! 🙂 I can’t wait to tell it. Hopefully after this weekend (I’m moving!) things will settle down and he and I can write it out. Trust me … I’m going to be 29 on Monday and this is the happiest I’ve ever been. There’s someone out there for you! 🙂

    • Jessie says:

      Haha well my current job is more of a client / creative manager. I’m working on social media projects, but I don’t really have much say in the content. I miss it! I’m hoping to start freelancing doing that soon once I have my bearings straight from the move. Hmm… I would say growing your own brand will help you a lot. I don’t even have a huge following, but I understand social enough from growing my own brand. I was lucky enough to have jobs where my main focus wasn’t social media, but I expressed an interest so when they needed help, they’d let me jump in on projects. Just jump in and try! Maybe try freelancing or offering to help other BIG bloggers/Instagram peeps out. I’ve always wanted to do that. I’m not sure if that’s good advice, but that’s what I’ve got right now. 🙂

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