The Rewards and Challenges of Having a Side Hustle

Welcome to a Kaftan Life first -- an interview! We were curious about the motivations, complications, and rewards of having a side hustle (or two!). So we interviewed four of the hardest working people we know about their side hustles.


In conducting this interview, we learned that having a side hustle can be challenging but can also be an outlet for creativity, stress, and one's passions.


The Interviewees

Katie BlemlerKatie Blemler
City: Manhattan, NY 
Hustles: Psychotherapist, Nanny

Annie BrownAnnie Brown
City: San Diego, CA
Hustles: Marketing & Communications Director, Founder of Lips

Hoang Vi FessendenHoang Vi Fessenden
City: Charleston, SC
Hustles: Stay-at-home mother, Director + founder of Charleston Bloggers Shoot & Brunch, Promotional Events Coordinator, Brand Content Creator, Blogger

Gregory TopscherGregory Topscher 
City: Brooklyn, NY
Hustles: founder of stationary company Shipwreck Press , founder of  vegetarian meal planning service Meal Ticket, park associate for the Naval Cemetery Landscape Park, and cleans apartments


What made you take the leap into having a side hustle?

KATIE: Managing NYC expenses; predominantly rent, so I can have my own apartment!

ANNIE: I felt like the world was ready for Lips as a digital platform!

HOANG: I needed a creative outlet and to be able to get out of the house and actually have intellectual conversations with others instead of just blabbing with my baby. We are not made to be alone.

GREGORY: I have never been an office job kind of person, and weirdly it just always seemed easier to me to have a couple jobs. Both for income and to not get sucked too deeply into the more negative parts of a job (the drama, the power struggles, losing interest in the work).


How do you balance having more than one job (or "hustle")?

KATIE: Relying on my memory used to be enough to keep balance, but now with 3 therapy jobs and periodic nannying gigs on weekends, I have been attempting to be more organized and actually keep a calendar... Mostly writing things down in some form, whether in a note, on my Google calendar, or the different calendars I have for various private practices.

ANNIE: My tools! Trello, Slack, Airmail and iCalendar are the only ways I stay organized. Hot tip - I color coordinate my emails :)

HOANG: I don’t... jk but really it’s hard! I try to set out weekends to spend with my family and friends. It’s hard to separate work from home because my clients are everywhere! But set intentional times for your special ones.

GREGORY: To be clear, financial insecurity is a good motivator. But two of my jobs I started because there was a hobby in my life that I wanted to give more time to, but without financial incentive it always felt like a distraction from my real work. I started my meal prep business, Meal Ticket, because I wanted to improve my catering skills while trying as many recipes from my many cookbooks as possible--as I tended to cook the same things for a year or two. But mostly, dropping the perfectionism of "getting everything right" and constantly worrying about pleasing and over-performing for your bosses, reveals how much space you have in your schedule after all.


What do you love most about having a side hustle?

KATIE: The extra cash! And also having time to spend outside of an office full of adults and instead running around with children. It’s a totally different kind of hustle, and is often a great way for me to unwind from the week. I know it sounds counterintuitive, but it helps me stay balanced mentally.

ANNIE: I am constantly inspired by the women* who share their experiences of sexual trauma, mental illness and self-hate via our platform, and share with me how Lips has improved their well-being. These women* keep me going in the face of discrimination and censorship.

HOANG: I love meeting new people of all types and walks of life. You get a taste of what you’re getting into and of what you’re trying to envision for them - for me it’s creating the type of content or event that curates their feel. Blogging is a creative outlet for me to share my recipes and share my love for fashion and passion for vegan, cruelty free, organic, and natural products.

GREGORY: I like the variety. It really makes each job feel fresh when you get your time for it. And the week has a really nice flow to it, with different little compartments and combinations of activities.


What’s the most challenging part of having a side hustle? How do you cope with or embrace that challenge?

KATIE: Feeling burnt out from time to time. Planning trips outside of the city has been helpful with coping with the burn out. Escaping somewhere near the water in particular is a great way for me to recharge.

ANNIE: There's ups and downs with a startup. Learning that rejection is just part of the process is big lesson that I am continuing to learn.

HOANG: The BIGGEST challenge is sometimes people try to undermine me, because of my age and my skills. A lot of people think they can take advantage of my work ethic and status. I deal with it by saying no to what is not worthy of my time. My time is so important: which leads to spending time with my loved ones like my family. I really have a hard time since my down time is when I can work when I’m not watching my baby, so my husband feels neglected sometimes so we set intentional date nights and workout nights so we can have alone time.

GREGORY: Getting overwhelmed and scheduling. When you something comes up and you need to travel, the calendar starts to get pretty scary.


What’s your best piece of advice for someone who’s considering having a side hustle?

KATIE: Make sure to listen to your body when you start noticing signs of burn out — whether physically or mentally — and give yourself a break. I’ve found that I can’t do as much as I could in my early 20’s and leaning into that was tough at first, but now I try to be more gentle with myself and take time to recharge when needed.

ANNIE: Take it slow. Success doesn't come easy or fast!

HOANG: If you want something and are passionate about it and you keep on making excuses for why you can’t, write down the advantages of what could happen if you do! One thing leads to another and then all of a sudden bam, you have your own little businesses and so many opportunities and people that can come your way!

GREGORY: Make sure each job makes sense. Make sure it's something that's exciting to you, but that also has a practical application outside of making money. Always be open to reworking things and trying something else. If one of your gigs is a drag, it'll reveal itself pretty quickly.


We recognize that the term "side hustle" doesn't always apply. Sometimes people work several different jobs with equal weight and importance to them. In other words, they have a diversified revenue stream. "Diversified revenue stream" just isn't as zippy as "side hustle"!

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Kaftan Life Interview Series: The Benefits and Challenges of Having a Side Hustle

Cover image/pin image credit: Arnel Hasanovic on Unsplash


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