How Do I Choose the Best Side Hustle for My Situation?

Dr. Robert Wallace
Mon, 13 Apr 2026 23:00:00 -0700
Lifestyle

DR. WALLACE: As a guy who is a second-year college student, I always need some extra income or spending money to help pay for my living expenses and social life, as well as to build up some savings.

The good news is I truly enjoy working, and I do have the drive and ability to try many potential side hustle opportunities. At this point, I've counted up a half dozen ideas that all look potentially viable to me. Because I have limited free time, I don't think I can do more than try one at a time to see if one of them works out. How can I best decide which order to try things? I really need at least one of them to work out to give me some financial breathing room since I'm paying for my own education, housing and living expenses myself. — Frugal College Guy, via email

FRUGAL COLLEGE GUY: Before you make it a decision on which one to try first, by perhaps trying to match up your personal skill sets to the opportunities, instead, seek to speak to a few people you know, or could be introduced to, who have more experience in the side hustle realm. These people can be your age or slightly older than you are, but you don't necessarily have to find someone who is a decade or two decades older than you are to get the advice that would be applicable and practical for you at this juncture of your life.
Updated: Tue Apr 14, 2026

DR. WALLACE: As a guy who is a second-year college student, I always need some extra income or spending money to help pay for my living expenses and social life, as well as to build up some savings.

The good news is I truly enjoy working, and I do have the drive and ability to try many potential side hustle opportunities. At this point, I've counted up a half dozen ideas that all look potentially viable to me. Because I have limited free time, I don't think I can do more than try one at a time to see if one of them works out. How can I best decide which order to try things? I really need at least one of them to work out to give me some financial breathing room since I'm paying for my own education, housing and living expenses myself. — Frugal College Guy, via email

FRUGAL COLLEGE GUY: Before you make it a decision on which one to try first, by perhaps trying to match up your personal skill sets to the opportunities, instead, seek to speak to a few people you know, or could be introduced to, who have more experience in the side hustle realm. These people can be your age or slightly older than you are, but you don't necessarily have to find someone who is a decade or two decades older than you are to get the advice that would be applicable and practical for you at this juncture of your life.

Those who have gone through the trials and errors of trying various opportunities out earnestly are those who can speak with the most congruent advice and insights that will likely benefit you.

Offer to do a favor, repay them with some free work for a period of time or to simply pay it forward once you get something up and running by helping someone else down the road. Seek to learn how to turn an idea or two into a modest to even attractive revenue stream that can help out with day-to-day expenses and perhaps even substantial savings to build that cushion you wisely are seeking to develop.

MY AUNT DOESN'T NEED ME THERE FOR SEVERAL HOURS

DR. WALLACE: My parents are out of town for two weeks, which leaves me home alone. It's no problem since I'm a 17-year-old guy who's very self-sufficient. I can handle making my own food, getting to and from school and everything related to daily life.

My aunt, who lives in our town, recently recovered from surgery and my parents wanted me to go over to her house every afternoon after school and hang out with her to help her. Then I'm supposed to return home to my house for sleep overnight and then check on her the next day after school and so forth.

Well, the first day I went over to check on her, she told me she's doing much better than she expected. She had me help her with a few very small things but told me it was no big deal and I didn't need to be there all afternoon and all evening for her. In fact, she told me it was fine to just stop in after school for 15 minutes each day to make sure she had everything she needs and then I can go on with my own free time to study, hang out with friends or play sports.

Do you think it's all right for me to follow my aunt's wishes and not spend as much time directly there with her, even though my parents were pretty firm about me staying with her all afternoon and evening until she went to bed? — She Reduced My Time, via email

SHE REDUCED MY TIME: Certainly, if your aunt is doing better than expected, and you stopped in to see her every single day, even for just 15 to 20 minutes, that should be sufficient. In today's modern world, I trust your aunt can call, text or make contact with you if she needs anything urgently. Make it a point to keep an eye on your phone and check it regularly, and even text your aunt every early evening before she heads to bed to see how she's doing.

If you really want to further insulate yourself, it would be a great idea the next day you're over at your aunt's house after school to ask her who her favorite and most reliable neighbor is. Go over to that person and explain the situation. Introduce yourself, explain you'll be stopping by after school each day to check on her, but that you also wanted her to have a backup person in her neighborhood who could maybe stop by for a few minutes each evening or even just give her a quick call to check in with her.

Taking care of another person in the manner you've been requested by your parents is more about reliability, following through and practicality. If your aunt is satisfied, and you're checking on her each day and keeping in close touch, I feel you're doing a good job on your part with this obligation.