Moonlighting Makeup Artist Earns Extra $25,000/Year

This transcript was generated from the episode audio and may contain minor errors.

Do you ever find yourself saying, "I wish." I wish I could do something that's important to me. I wish I could travel. I wish I could finally start that business. I wish I could run away and join the circus. Whatever it is, I'm going to encourage you today to do two things.

First, separate your true desires from generic wishes. Okay, so if you really want to run away and join the circus, okay, that's fine. But if it's just something you say, then let's just kind of set that aside. Then whatever you really want to do, stop saying, "I wish," and start saying, "I will." I will find a way to take that trip. I will find a way to start that little business.

Despite the demands on my time and all my obligations, I will find a way to do what's important to me. Welcome to Side Hustle School. My name is Chris Guillebeau, and today's story features a young marketing director who earns $2,000 a month on the side by doing makeup sessions on weekends. Her story begins with an "I wish" moment, but it turns into an "I will" success. So let's say a quick thank you to our sponsor, and then I'll tell you all about this moonlighting makeup artist.

28-year-old Caitlin Tuzolino didn't act on her dream immediately. Upon graduating from college, she dove headfirst into the corporate world. Since then, she's created and led marketing departments for an accounting firm, a software company, and an automated manufacturing company, where she currently helps raise brand awareness and drive sales. Caitlin was busy, in other words, but she also found herself longing for more. She noticed that she increasingly started sentences with "I wish," and then she realized it was time for her to stop wishing and just get to work.

What would she do? Well, she'd always been good at doing makeup. The former competitive dancer had honed her skills in high school, and then in college she was constantly asked to do her friend's makeup before they would go out on the weekend. So a bit later, when she'd long to do something more than just her corporate job, makeup by Caitlin Michelle was born. Or shall we say, it was made up.

Caitlin knew that lots of weddings took place in her city of Rochester, New York, so that seemed like a good starting point for the side hustle. But no makeup artistry would be viable without a trip to Sephora to stock up on products. With each biweekly paycheck that Caitlin took home from her day job, she would drive to Sephora and stock up on items to grow her professional makeup kit. One week she would purchase various shades of foundation. Her next trip was for lipstick.

After a few trips, Caitlin had a full-blown kit that she was ready to put to work. She started practicing on anyone and everyone she knew. Friends, family, friends of friends, you name it. Pretty much everyone except her dog. After practicing different types of makeup looks on different face shapes, she took photos to begin building a portfolio she could use to showcase her talent.

She then took that portfolio to local hair salons, asking if they'd be willing to refer her to wedding parties. To her surprise, two of the salons agreed. Caitlin capitalized on this win immediately. She created an Instagram account, a Facebook page, and a website so that potential clients could see more of her work. To build that basic WordPress website, she watched YouTube tutorials.

She also knew that Pinterest would be another good place to share her work and reach potential clients, so she began to share posts there as well. To build her skills and gain clients, Caitlin took on any client or opportunity that came her way. If just one person in a wedding party needed makeup, she would do it. If someone needed makeup done for a photo shoot, she was there. She worked to build a name for herself in her first year, and it paid off quickly.

She now serves clients throughout New York State and books 20 to 30 weddings per year. Since those early days of taking every client that came her way, Caitlin has built her reputation to the point where she can now require a minimum booking of six people for a wedding day. And after just one year of starting, she became booked for weddings almost every weekend of the year during the busy season, and it's been that way ever since. Not only is she able to make more money doing something she loves, she gets to help people feel confident as they celebrate a special day. To her, that's half the fun.

When she started, she remembers getting a small $100 investment from her grandmother, along with a letter that said she believed in her and couldn't wait to watch her make people feel good. Now Caitlin earns about $25,000 a year in her side hustle. It's a seasonal business since many more brides get married in the summer, but she still earns enough money to allow her to travel, pay off her student loans, and take a few trips to Sephora just for herself. The process hasn't been free of challenges or mistakes, like the time she left a brand new makeup machine behind at a bride's hotel, but even the worst mistakes can be learning opportunities. Caitlin doesn't know what the future holds for her or her side hustle.

She says she's glad she didn't wait for the perfect moment, because that perfect moment probably didn't exist. She's learning new skills, like lash extensions, microblading, and some other things that sound important but I don't know much about. Most of all, she's glad she went from "I wish" to "I will." You've probably heard the cliche, "If you love your work, you'll never work a day in your life." I mean, it is a bit of a cliche, but I think it's also important to love your work. The whole reason you're doing something like this is because you recognize life is short and you want to do something that matters to you. You want to create more options for yourselves that you have, more freedom of choice, even if you love your job, even if you are perfectly satisfied in your situation, a lot of us still have this longing to do something different, just like Caitlin did.

So by the way, we asked Caitlin how she feels about spending much of every weekend, especially during the busy season, doing makeup sessions, and she was pretty clear that she wouldn't have it any other way. She was like, "This is what I love to do, and it's great that I can also get paid for it." And I would say besides, even if she does get tired of it at some point, well, that's okay because this isn't her main job, it's not the income she relies upon, so it's kind of like a bonus. Now, last but not least, speaking of bonuses, we don't talk about taxes very often on the show because people are in different situations and it's different rules for different countries. But in a lot of countries, and certainly in the US, if your side hustle has expenses like purchasing a lot of makeup, well, of course, you should consult your tax advisor because I am not one of those, but it is usually pretty simple and straightforward, especially once your business is profitable. If you're buying things like makeup or whatever it is that you buy, then those items can be deducted on your taxes.

So as you grow your side hustle, be sure to get some counsel on that because you can probably save a lot of money. I usually talk about making money, but of course, you know, saving money is not bad. My hope for you is that you will stop saying "I wish" and start saying "I will." Don't forget that inspiration with action is the best course of all, and today's show notes are online at sidehustleschool.com/539. That is for episode 539. Congrats as well to Caitlin.

If you're out there planning to get married or otherwise need makeup done in Rochester, New York, she may be booked up, but perhaps you can check with her just in case. And I hope you'll check back with me tomorrow. We are winding down the week, but we've got a weekly recap coming up tomorrow and then a whole new set of stories all next week. Thank you so much for joining me. I love making this show for you.

Much more is on the way. This is Chris Guillebeau for Side Hustle School.