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Side Hustle: I was a personal assistant for a 19-year old


I was 23 years old, a Registered Dietitian (RD) with a bachelor’s degree, and a personal assistant for a 19-year old. Why would I take a “job” like this?

Help Wanted

Since we moved to a city for my husband’s job I was limited to where I could job hunt. I decided to look for babysitting jobs to make a little cash until I could find a real job (Now I have 4 jobs!), so I set up a profile on and started searching for help wanted ads. I came across an ad titled “Student Helper” that was posted by a dad (we’ll call him Bill). His son (we’ll call him Jack) was about to start his freshman year at the university nearby as an out-of-state student and had Type 1 diabetes.

Bill wanted someone in town to be available in case Jack needed a medication picked up or to be taken to a doctor’s appointment. Bill stated he would pay $20/hour in addition to a $500 retainer for the semester. Since I’m an RD and know about managing diabetes, I sent a message saying I was interested and offered to help move Jack into the dorm so I could meet them and see if I was a good fit. Bill agreed and I arrived on move-in day to meet him and Jack.

Disclaimer: You’ll quickly pick up on the sad story of a rich dad who had a broken relationship with his son and tried to make him “happy” via money but it only left the son incapable of doing anything on his own. I’m going to leave out the family dynamics and only discuss the financial aspects of the story.

Jessica: RD, PA (personal assistant)

About 10 minutes after meeting Bill and Jack I am handed a pair of keys to one of two SUVs Bill rented from the airport. Bill took one SUV and I took the other to a nearby parking garage. On our walk back Bill explains that he’d like to pay me for helping with the move in and hands me what looks like a couple $20s but I found later was $100. He insisted I take it so I tucked it in my pocket and we continued our conversation.

We get back to Jack’s room and I help them unpack and reorganize the room with his new roommate. I awkwardly introduce myself as Jack’s friend to the roommate and his family since I wasn’t about to say I’m just a glorified PA. Fast forward through the day and we get to the part where I help Jack unpack a brand new flat screen TV and a wall mount. I’m not even sure you’re allowed to mount a TV on the wall of a dorm room but they didn’t seem to care.

Bill asked if I knew who they could hire to set up the TV and I mentioned my husband is a handy man and can swing by in the evening to do it. Fast forward a little more…the TV is hung up and I call Bill to let him know we did the job. He tells me to stop by a restaurant he’s at so he can pay me for the semester. Now the fun begins…

Dinner and $1,250 later

Hubs and I show up to this fancy restaurant (in our workout clothes) and Bill invites us to join him and his ex-wife for dinner. We looked for the cheapest thing on the menu which is a $14 burger and declined the offer of wine. We had great conversation and got to know each other a little more.

At the end of dinner he gets his checkbook out and says “I’m paying you the $500 retainer, adding another $500 to pre-pay for 25 hours, and a little more for hanging up the TV for Jack.” In case you missed that, I got paid $250 for watching my husband mount a TV on a wall. My thoughts: What am I getting myself into??

Details & an early ending

Part of my job was to call Jack every morning to make sure he was up in time for class and I brought breakfast to him if he needed it even though he had a meal plan in the cafeteria downstairs. I drove him to doctor appointments and occasionally class even though Bill’s personal assistant drove Jack’s 2011 Audi five hours to the university where it was parked in the closest rental space to the dorm I could find for $80/month.

Bill’s personal assistant set up an Excel sheet for me to log my time and expenses. She sent me a check ahead of time so I’d never have to spend my own money on Jack. It was a hectic semester for Jack and I quickly learned how irresponsible he was both with school and his own health. His roommate called 911 twice and I called once for a low blood sugar because he simply forgot to eat or didn’t feel hungry. Unfortunately Jack was unable to keep up with school since he skipped class a lot and took awhile to bounce back after hospital visits so he took a medical leave in February and moved back home. Thankfully, timing was perfect for me and I got called with a job offer as a dietitian while I was helping Jack move out of the dorm.

Total earnings

After adding the up-front retainers, the additional hours I logged, plus extras like mounting Jack’s TV and a pleasant $350 Christmas bonus, the total earnings from this “job” came out to $3,615. That doesn’t include the monthly data plan added to my phone that Bill paid for in case he needed me to check my email while I was out. It also doesn’t include all of the food, laundry baskets, two French presses from Whole Foods, a knife sharpener, fruit bowl, and other décor I was simply given after helping Jack move out of his dorm and cleaning the condo Bill rented for the semester for when he came to visit Jack. Total hours logged: 95.75 which means my hourly wage came out to $37.75 per hour. Not bad for a “babysitting” job.

Have you ever worked an odd job to make some extra cash? Would you ever take a job as a personal assistant?



My name is Derek, and I have my Bachelors Degree in Finance from Grand Valley State University. After graduation, I was not able to find a job that fully utilized my degree, but I still had a passion for Finance! So, I decided to focus my passion in the stock market. I studied Cash Flows, Balance Sheets, and Income Statements, put some money into the market and saw a good return on my investment. As satisfying as this was, I still felt that something was missing. I have a passion for Finance, but I also have a passion for people. If you have a willingness to learn, I will continue to teach.


  1. That’s not a bad wage at all for a side hustle, well done!

    I did some blog management for an electric car site once. It wasn’t glamorous, but I learned a lot about electric cars in the bargain. Not a bad deal!

    • Sounds like my friend who got a marketing gig through a company that sells parts to NASCAR. She is a total girly-girl but learned a lot about cars through the process!

  2. Nice way to earn some extra cash. If I had someone hand me that kind of cash upfront, I would probably be worried that I got hired into the wrong type of family, as it seems you had similar thoughts.

    • I thought the same but I’m glad we ended up staying for dinner and getting to know what the dad did for a living and more about his son.

  3. This sounds like a neat retirement job! Seriously, this kid needs to grow up and take care of himself. I lost a friend due to diabetes. He did not watch his insulin and died in his late fifties.

    • It was a sad and frustrating situation. I’m sure he’ll have complications down the road since he does such a poor job caring for himself now. I just pray he gets his act together and starts taking responsibility for his health.

  4. Hey, at least it all worked out for you. That was one great side gig.

    • I was pretty shocked at how much money I made. It was inconvenient at times but not nearly as demanding as other jobs that would pay $37/hour I’m sure.

    • It was a little stressful at times and I don’t think a SAHM would have the flexibility to drop everything to go pick up a bottle of hot sauce for this kid 😉

  5. That’s crazy! Sort of nerve wracking though, since his dad was so dependent on you. I take it he assumed his son didn’t need a baby sitter come his second year?

    • Well unfortunately he just didn’t take care of himself well enough and he fell behind in classes so he transferred home before his second semester ended :/ Sadly, I’m confident his dad’s secretary is back to work managing every detail of his life.

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