Q&A with Illustrator Kayden Hines

 Kayden Hines

Kayden Hines

Kayden Hines is a BOSSLADY. After some back & forth banter on Instagram, I planned to meet her for drinks IRL. I wasn't sure what to expect, as one's internet persona never quite paints the full picture. But lemme tell you - she's my spirit animal. We may or may not have turned "a quick drink" into a 3-hour encounter. And I was enjoying every second of it. She's a gem. Enjoy!

Tell us a little bit about yourself!

Before last summer, I would have described myself (and what I did) very differently!

I had worked in the TV business for close to 8 years, first at Discovery Channel and then at Apple, and graduated from business school a few years ago. Even though I love business, I am also creative, and felt for the longest time that I hadn’t been using that part of my brain in my career. Last summer, I made the decision to quit my job at Apple to start making my own content, with the ultimate goal of having my own TV show.

I’m writing a book right now about “millennial malaise” (feeling lost when work is no longer personally fulfilling), as well as a screenplay and podcast on the same topic, and have started an Instagram account (@kaydenhines) to document my journey into creativity, where I share some of my concepts and observations in illustrated form.

I think what drives me, at the heart of it, is that I love connecting with people by entertaining them and making them laugh. I’m fascinated by the things that make us all human, (our best and worst qualities), and that connect us all no matter where we come from or what language we speak. This drives me to not be afraid to “go first”, meaning, I am more than OK sharing embarrassing and weird stuff about myself if it helps others open up too.


What was the inspiration behind your account?

Once I quit Apple, I started working on my book & screenplay. And I was like hooooly sh*t, this is a huge project and it will take me a very long time to produce something I’m happy with.

Writing is a pretty solitary endeavor, and as someone enjoys the act of SHARING my writing more than the process of writing, I needed some connection to the outside world while I continued working on my book. That’s why I decided to start my Instagram account @kaydenhines. It’s a great way to test out concepts I’m writing about in illustrated form and see if they resonate, but it’s also a great creative outlet because it forces me to use a completely different part of my brain than I was used to in the corporate world.

I love connecting with people by sharing my insane thoughts and observations with the world; it opens up the door for people to share their own experiences. It’s kind of how I operate IRL; I often break the ice right away so we can get to the good stuff more quickly.

My goal---beyond my account being a creative outlet for me---is to make people feel less “alone” by seeing themselves in my posts. I also hope to inspire others who feel stifled creatively to just go for it, make stuff and put yourself out there and see what happens.

 Kayden Hines

Kayden Hines


For a complete newbie, what are your favorite tips for someone looking to get started with their own brand/side hustle?

Having confidence and the right mindset are a HUGE part of the battle, at least for me. Often a side hustle is something very different from what you’re doing at work, or how people perceive you. For example, I worked in the corporate world for almost 10 years, and went to business school, so creativity was something I had pushed to the wayside a long time ago because it wasn’t relevant to my job description. Having the confidence to break away from constraints you’ve put on yourself: whether it’s belief in your own abilities, wondering “what will people think”, or being too afraid to start because you’re afraid of failing is 90% of the battle. It took me several years to get to the point where I felt confident enough to quit my job to write and start creating content. The more you can get into the mindset of not caring what other people think, the more you can focus on building something every day.

I’d also say spend a lot of time getting to know yourself. The more you can identify what makes you YOU, what gives you energy, and how you spend your time for fun, the more you’ll be able to articulate what your long term goal is, and the more seamlessly everything will fall into place.

Another tip: be strategic. Know how your side hustle fits into your larger and longer-term goals. It makes it easier to say yes or no to opportunities as they come your way. Your energy, focus, and time are some of your most precious and limited resources, so make sure you spend them wisely and know why you’re doing (or not doing) something.

Finally, just get started. Take one small step that brings you closer to your goal that you can do every day. You’ll never regret trying and failing, but you will regret never trying.


What do you love most about your job?

I love getting to create something every day and putting that part of my brain to use. The coolest---and sometimes most frustrating---thing about being creative is that you can’t force an idea to come to you. Ideas and “aha moments” often come when I’m NOT thinking about them, or the dots will connect in some way. So I’ll be in the shower or watching a TV show and finally I’ll be like, HOLY SH*T YES!!! That’s how I can make this idea work! So when something isn’t working, I take a break, walk my dog Yoshi, watch TV, read a book, scroll through Instagram, or take a nap. ALL IN SERVICE OF THE CREATIVE PROCESS.  I mean, when else can you claim that watching TV actually helps you be more productive at your job?? How amazing is that??

I also love having conversations and collaborating with people. It’s another way that I get inspiration for new ideas, and also a way to see whether my ideas resonate. I love that I can take an insane thought or observation that exists in my head, turn it into something tangible, and put it out in the world. Seeing people say they relate to my work or that they share similar experiences is such a cool feeling, and makes me feel less alone in this crazy world!


What do you love most about yourself?

I’ve always loved that I can make people feel comfortable and open up--usually by making them laugh--and that I can connect with people and cut through the bullshit. I like to think I toe the line between oversharing and being relatable, but my husband can attest that I freak out after 90% of my conversations and ask him whether I “finally shared too much this time.” Nothing bad has happened yet, which means I will probably keep oversharing. :)

Overall, I love that I can make it easier to connect with people on a deeper level. It makes conversations and relationships much more fulfilling and interesting. It also makes me feel less alone on a human level.

 Kayden Hines 

Kayden Hines 

Take us through a day in the life of Kayden. We want all the deets!

Every morning, I wake up at 7am to let my dog Yoshi out. He is the snuggliest and cutest dog in the world, so sometimes I get sucked into snuggling with him in bed for longer than I should, but I also think these are some of the best moments in life so I don’t try too hard to get up. While snuggling with Yoshi, I’ll scroll through Twitter, Reddit, Instagram, see what I missed in the world overnight, and then I’ll look through my list of illustration / Instagram post ideas that I haven’t done yet. Once I’ve found one that I’m excited about, I’ll go downstairs start drawing. Actually, I’ll make coffee first, then start drawing. I’ll probably work for about 2 hours or so, then go to the gym, and when I come back, I switch to writing and doing research for my book. I’ll work until I feel stuck, or run out of energy, and will take a break by walking Yoshi, watching a TV episode, or reading something that requires no brain power or concentration (like Daily Mail articles). Then I’ll switch back to working on my illustrations, collaborations I’m working on, and respond to emails and comments on my Instagram.

Because I’m producing content every day, I have a constraint on my time (knowing that I need to finish a drawing each day no matter what), which actually forces me to be more productive and intentional about my time.


What's on the horizon for you in 2018?

Continue writing my book and screenplay; launch some mini illustrated series and expand into new content on my Instagram account; experiment more with podcasting, video and written content; and create a community around @kaydenhines.


And lastly, what makes you feel like a kween?


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