Picture this. You’re 24, you’re an aspiring artist, and you lost your first full-time job in the creative industry. What do you do? You become a determined freelancer, of course.

That was me in early 2023. I always wanted to be a professional photographer, and my old work closing seemed like the perfect leap. No one around me was a freelancer, so I struggled to make my own community. I constantly reached out to young people in my shoes with not only the intention to pick their brains, but to genuinely befriend them. I’m so lucky the following people have let me into their work worlds and answered all my questions. Because I understand the hardship, I am even more wowed by these folks who live off what they love. 

So, I set off to document four artists who have begun to make a living from their passion. They’ve found a way to navigate making their hobby a business. They impress me and inspire me. My hope is that once you read this article, they’ll do the same for you.

Yas Awsem and inventing ‘Radical Queer Witches’

• Yas’ Instagram: https://www.instagram.com/heart.led/
• Radical Queer Witches Instagram: https://www.instagram.com/radicalqueerwitches/
• Radical Queer Witches shop: https://radicalqueerwitches.com/
• Yas’ pronouns: she/they

I first met Yas Awsem at a yard sale. While her friends were selling items from their home, I remember Yas sitting on the grass handing out flyers about her card game. It seemed like great timing. Cards Against Humanity was out, and so Yas’ game, Radical Queer Witches, was so in. As I got to know Yas a little better, I was impressed by the tenderness in their heart, passion to help their community, and continuous work ethic. As a fellow freelancer, Yas is someone I look up to when navigating the hard things. I hope you’re inspired to support them after e-meeting them too.

What is your name and what do you do?

My name is Yas and I’m an artist and creative! I screen-print and design clothing, I am the creator of a card game called Radical Queer Witches, and I am currently writing a book about intuitive creativity!

When did you start your business and how?

I started my journey towards entrepreneurship and building a small business in 2019. I was 21 years old living in south Florida working food service jobs. I was extremely burnt out and broke. My mental health was at an all-time low and I just knew I needed to change something about my work life to feel more fulfilling. My biggest dream at that point was to make money from my own creativity in a way that felt nourishing. There was a day where I had the worst panic attack of my life.

I’m not super religious, but I remember praying that day for guidance through this process and to find something that works for me. A few days later, I got a vision for my first business (Blessed Up Threads) and that’s where it all started! I screen-printed clothing for about four years consistently until I created my card game in 2020, and it became more of my focus over the last year or two. Now, I find myself phasing out of Radical Queer Witches and moving towards becoming an author and mentor for other LGBTQIA+, BIPOC and marginalized creatives!

Yas’ card game, packed up (left) and in action (right). Photos: Allison Barr

When did it become a full-time thing for you?

It became full time for me about a year after that. I eventually moved back to Portland in fall 2019 and got a job at a juice bar for a couple months, where I ended up getting let go for the first (and only) time of my life. It was the biggest blessing in disguise and really allowed me to focus on screen printing. It really affirmed to me that I really am not meant to be an employee! 

What was that transition like from it being a hobby to it being a business?

Screen-printing was never a hobby for me; it started off as a business venture and has only now become a hobby as I focus on new aspects of my creative path! I find myself creating for fun and pleasure these days more than for money, which is so fulfilling, because I never imagined I would be able to not stress about money 24/7 at such a young age.

What’s your favorite part about working for yourself?

100 percent the freedom over my time. I love choosing what I want to do with my days and not having to drag myself to a job a day where my body is asking for rest. I still struggle to rest, ironically, but it feels better for it to be my own decision versus something that’s made for me.

I’m an extremely hard worker and I used to pour my energy into the establishments I worked for just to be given little in return. I remember at one of my jobs, I made my family’s sacred Lebanese lentil soup for a special, and that’s when I realized that I’ve taken it too far. Why was I sharing such intimate parts of myself for a job that paid me $10 an hour with no benefits? I have so much to contribute but it was constantly unappreciated or undervalued. I love being able to work hard, and it’s all for me and my community versus making someone that doesn’t even care about me richer. 

What hole do you think you’re filling in your community?

I wouldn’t say I’m filling a hole quite yet. There are so many talented QTBIPOC creatives in my community. But the space I do hope to fill one day is to be an accessible and supportive mentor for young, marginalized creatives who have been in a similar space as me and desire more from their creative and financial lives.

I love self-growth and I have spent 10-plus years in the therapy and coaching worlds. What I’ve discovered is that a lot of mentorship and coaching is extremely inaccessible, specifically for marginalized people. I want to lift up people in my community to find empowerment in their creative, financial, and work lives. I want young marginalized people to build wealth, to feel freedom, and choice in their lives instead of feeling trapped in unfulfilling and soul-draining work. This is what I am currently and have always been working towards, whether I knew it or not at the time!

What’s the biggest obstacle about working for yourself so young? What’s the biggest thing you’ve learned?

The biggest obstacle … well there’s quite a few! But I’d say one of them is by far navigating everything for the first time mostly alone. I’m a first-generation American, neither of my parents come from wealth or have strong education, so becoming self-employed was and is a constant trial and error. You try one thing, it doesn’t work, then you pivot and keep trying until you get it. Sometimes it’s small things that don’t matter, but sometimes you do something that could have been so avoidable if you just had someone to pave the path for you. That’s part of the reason why I feel so passionate about becoming a mentor, because I never had one and know how valuable it would have been to have someone guiding me from the beginning. 

What is the first thing you want other young people in the arts who are starting their own business to know?

A big piece of advice that has always stuck with me is to “choose your hard.” Becoming self-employed, starting a business, and working for yourself is extremely challenging. Sometimes it’s nonstop work, sometimes there are periods where absolutely nothing happens and you start to wonder if you’re failing and if it’s ever going to work. But what’s also hard is waking up every day and going to a job you hate. Or getting stuck somewhere you can’t grow or flourish. Or never making enough money and living paycheck to paycheck.

You gotta choose which hard you’re committed to: the uncertainty and unpredictability of following your heart or the unfulfillment of your potential and staying stuck where it’s comfortable. Both are hard, both will trigger you — but which will ultimately bring you closer to yourself and your vision? You have to be your biggest hype person and believe in yourself endlessly. Even when you stop believing in yourself for a little, you have to keep returning over and over. It’s a deep practice of learning how to trust yourself!

Tifa and the joys of telling “terrible jokes” online

• Tifa’s Instagram: https://www.instagram.com/tifataco/
• Tifa’s pronouns: she/her

I instantly had so much fun the first time I met the woman whose online name is Tifa. And when she told me what she did for work, I was in awe. Since she is a couple of years older than me, it was so fascinating to hear about her path and stability. She was living proof to me that working for yourself is possible! Her persistence to be successful, do what she loves, and provide for her family really shone through to me. How cool, I thought, that we live in an age where being an online creator can positively impact so many lives.

What is your name and what do you do?

Hi, I’m Tifa! I run my own business in the entertainment space, focusing on community-building and making people laugh at my terrible jokes. I love connecting with my audience through live streaming, creating a virtual room where everyone feels welcomed and valued.

When did you start your business, and how?

I actually started my business a couple years ago, by accident! After classes, I would sign on, slip into my amateur stand-up comedian alter ego, and interact with anyone who came into my room for fun. It started as just chatting about TV shows and listening to their stories, but then I noticed I was passionately dedicating all my free time to this community. Over time, I realized I needed to turn that passion into something more sustainable and, you know, that would allow me to pay for food. So I took the plunge and started treating it like a business, letting go of a traditional career path. 

When did it become a full-time thing for you?

The moment I graduated college, this had officially taken over as my main source of income. I could have started sooner, but as a first generation Asian-American, my parents constantly reminded me that they didn’t make the perilous journey to this country, working tirelessly for a bowl of rice, just for me NOT to get a college degree.

What was that transition like from it being a side gig to it being a business?

First, I’d like to applaud anyone who has risked it all to evolve their side gigs into their livelihoods. It’s a brave feat because it’s a scary one, and I feel this fact is underappreciated. For me, the transition was at first scary, then liberating. I risked financial stability to do something I love, and become this person I truly want to be.

What’s your favorite part about working for yourself?

A lot of people probably say this, but the best part is creating my own hours, hands down! Especially as someone who struggles with focus and battles with clocks, living in my own world with my own clock has been surprisingly fruitful and more fun.

What hole do you think you’re filling in your community?

More and more people were coming to me and I began feeling a sense of responsibility for their social well-being. Through my own business, I discovered and fully realized my purpose: I combat loneliness. I don’t just tell bad jokes and obsessively talk about The Simpsons; I listen to people share their stories, let them request silly activities to play together, give them nicknames, and essentially let them know they’re being heard and are part of a community. 

What’s the biggest obstacle about working for yourself so young? 

Marketing! Doing the work is easy; suddenly realizing your time and effort isn’t very profitable is the hard part. I was very inexperienced in executing actual business and marketing concepts. Even to this day I am a bit unsure what my services are worth monetarily, and I’m definitely not doing enough to make myself or my services known. But I have learned so much and know I will continue to learn so much more.  

What’s the biggest thing you’ve learned?

Beyond learning to maintain a consistent social media presence, I’ve more importantly learned to overcome self-doubt. Like, you can get so far and feel so excited for your milestones … until that moment you see someone farther ahead in their journey, or you read one negative comment and it devastates you. Yeah, that’s not a thing for me anymore, I no longer doubt myself, I celebrate. These are the positive mantras I repeat to celebrate my journey: 

1. I know my mission and love what I do

2. I cheer on peers and people I look up to 

3. and I wish for people who take the time to be negative to find inner peace

What is the first thing you want other young creative people who are starting their own business to know? 

Oh my gosh, just be authentic and be a nerd in whatever your passion is. People will resonate with your authenticity. It’s a very cute trait! Pair that with not being a butthole and you’re in business, babe.

Ruby Webb and her fruitful interpretations of time

• Ruby’s Instagram: https://www.instagram.com/fruitfulinterpretationoftime (you can order through there, too)
• Ruby’s pronouns: she/her

When I first saw Ruby Webb’s work on Instagram, I knew I had to collaborate with her. As someone always on the lookout for local fashion designers, I find that so much of the Portland fashion scene is street style or knitwear based. While there is NO shade to these creatives whatsoever, it just made seeing Ruby’s patchwork designs all the more fun. There’s so much I love about Fruitful Interpretation of Time. I can’t decide between it being a one-woman show, or her focus on size inclusivity. Either way, I hope you fall in love with her work just as much as I did.

What is your name and what do you do?

My name is Ruby Webb and I run a sustainable & size inclusive garment operation called fruitful interpretation of time (FiOT). 

Tools and raw materials of the trade. Photos: Allison Barr

Cutting the material (left) and arranging it in place. Photos: Allison Barr

When did you start your business and how?

I was introduced to sewing back in summer of 2019 by artist & designer Alexa Stark. In 2020 Fall I taught myself how to sew and constructed the concept of FiOT. I quickly realized how inspired I was to create clothing in my own style & size, which I had always struggled to find.  

When did it become a fulltime thing for you?

Sometime later in 2020! I started receiving lots of custom orders and slowly began selling my work in small shops all over the US. 

What was that transition from it being a hobby to it being a business like?

It began as a creative outlet for my own personal use and wearing. I think the transition came when I realized the people surrounding me were curious, interested and appreciative of my work. I gained another layer of confidence to continue sewing and push my garments to the next level. 

What’s your favorite part about working for yourself?

I adore being able to create, rework and style garments whenever I please in the comfort of my studio. I now have been sewing in the downstairs area of my house for around 4 years and so much has been produced from inside these walls, it’s insane to think about sometimes. I am able to go fourth with an idea and bring it to life whenever I please. 

What hole do you think you’re filling in your community?

I want to be fluid and fill as many holes as possible. Wherever and however people want to interpret and recognize my work, I gladly welcome it. My work is playful and no matter who the person is, I just hope they enjoy themselves while wearing FiOT. 

What’s the biggest obstacle about working for yourself so young? What’s the biggest thing you’ve learned?

In my case, I feel like I’m constantly on the go and sewing nonstop or cataloging my work; it takes constant time and effort. Putting up boundaries is very important. It’s easy to be swayed by pressure, people and trends, but in the end you only know what’s best for yourself and the work that comes along with it. 

What is the first thing you want other young people in the arts who are starting their own business, to know?

If something is calling you, go for it. Try it out and there might be a natural groove you get yourself into. 

Aurianna Oricchio-Gilley and the meditation of beads

• Aurianna’s Instagram: https://www.instagram.com/sownseedbead/
• Aurianna’s shop: https://www.sownseedbead.com/
• Aurianna’s pronouns: She/her

Aurianna Oricchio-Gilley welcomed me with kindness and patience the first time I met her. It’s the same with everyone she meets. Aurianna let me into her intimate world of beading. You can tell how much care she puts into her process; from designing bead by bead on her iPad, to creating high quality images for her marketing. She’s a hard worker, you can tell immediately. And she is passionate about so many fields in the creative world. She inspires me in her mindfulness and maturity in everything she does.

What is your name and what do you do?

My name is Aurianna and I’m an Indigenous bead weaver from Oklahoma.

When did you start your business and how?

I started my business in 2020 after I lost my job due to the pandemic. I mostly sold to family and friends for next to nothing while I learned and grew. Next thing I knew I was being offered an opportunity to make beadwork for [the hit television series] Reservation Dogs.

When did it become a fulltime thing for you?

Beading isn’t and has never been my full-time job. It is supplementary, and I can rely on it when I need to. Although I could bead full time, it is not the direction I’d like to take. Beading is a special meditation for me, a space where I feel creative. Placing financial pressure on my art form would take away the organic nature of my craft. Additionally, beading is a slow craft. It can take me anywhere from two to eight hours to make a single piece, depending on the complexity. This is not an ideal model for producing for high demand, nor would I want to sacrifice the quality of my pieces to do so.

Beads at the ready (left) and beadwork transformed. Photos: Allison Barr

What’s your favorite part about working for yourself?

Working for myself opens up space to nurture spontaneity, and make time to care for my body. Although it can be challenging to manage my time well, I wouldn’t have it any other way.

What hole do you think you’re filling in your community?

I think it’s less of a hole in my community that I’m filling and more of a hole that people are filling for me. The community I’ve found in the beading world (even though it’s mostly online) has made me feel so valued as an artist. For people to recognize what I put into my craft and support my ability to do so lends to a gratitude that’s unmatched.

What’s the biggest obstacle about working for yourself so young? What’s the biggest thing you’ve learned?

I think the biggest obstacle I’ve faced is having to spend so much time on social media in order to be successful. While yes, it’s often rewarding, it can also be very discouraging. I can spend hours working on a post or a video that is hardly seen. And although Instagram’s algorithm is often working against me, it’s become necessary in order to share my art, and that can be frustrating. The biggest thing I’ve learned is to not let it dictate my value or the way that I post. I know the type of content that Instagram wants and if I don’t feel good about making a five-second reel for views, then I won’t do it. It’s very important to me that I feel good about what I share of myself. Beading is incredibly personal for me.

What is the first thing you want other young people in the arts who are starting their own business, to know?

If you are an artist who’s decided to sell your work, my biggest advice is to be patient. Spend some time getting to know your craft, your style, and your relationship to it before you start selling. Bringing money into your creative space allows for capitulation to other people’s idea of what your art should be. Stay true to what you love and what you want to say. 

To end with one of my favorite quotes: “How, in our modern world, can we find a way to understand the earth as a gift again, to make our relations with the world sacred again? … If all the world is a commodity, how poor we grow. When all of the world is a gift in motion, how wealthy we become.” — Robin Kimmerer