“From Avocation To Vocation: How I Turned My Hobby Into A Career” With Jessica Massey of Woodstock Rustic

An interview with Phil La Duke

Phil La Duke
Oct 13 · 10 min read

Customer connection is critical! With an online business it’s more important than ever to let people know that there is someone “real” behind the curtain and that we care!


As a part of our series about entrepreneurs who transformed something they did for fun into a full-time career, I had the pleasure of interviewing Jessica Massey. Jessica is the owner and creative force behind Woodstock Rustic, LLC, a home decor and personalized art studio. She established the business in 2014 mainly as a creative outlet outside of her corporate graphic design career. However, the business grew rapidly in the first year and soon became her full time passion. Since then, the company has grown exponentially and has expanded to a five — six person crew and a home studio on three acres. Jessica earned a BFA from Savannah College of Art and Design in 2004 and then began working as a designer for several companies — first with International Greetings and then with Plaid Enterprises — where she focused on surface design and illustration.


Thank you so much for doing this with us! Can you tell us a bit about your “childhood backstory”?

There’s nothing too earth shattering here. I’m an only child from a family of entrepreneurs, so I guess it’s in my blood. My grandfather and parents were both in residential and commercial design and construction. I grew up wandering around construction sites and watching my family design and build things first hand from the ground up.

Entering high school, I knew I wanted to do something creative but not necessarily follow in the family business. While I didn’t really know what graphic design was at the time, it ‘spoke’ to me somehow. The school had a screen press that students in the program would be using, and I think I might have just been excited about the prospect of designing my own tee shirts! But from my first class, I fell in love with it all and ended up taking four years of design courses. The teacher, Mr. C as we called him, was awesome too which helped spur my enthusiasm. At graduation, there really was no question about what I wanted to study in college.

I guess I’ve actually come full circle now. While I don’t design and build houses, like my family did, I design and create art to decorate them!

What was the catalyst from transforming your hobby or something you love into a business? Can you share the story of your “ah ha” moment with us?

My “ah ha” moment came when I was shopping one day at Michaels Craft Store and saw one of my designs, but with a well known person’s name given the credit on the packaging. I knew that part of my job back then was being a “ghost” designer for other people and brands, but seeing it in person at the store that day was just the kick I needed to take a leap of faith and start building my own brand. I also think the timing was right. I’d spent ten years in the corporate design world and it was time for a change.

There are no shortage of good ideas out there, but people seem to struggle in taking a good idea and translating it into an actual business. How did you overcome this challenge?

I always tell people I stumbled into it and I think that’s true for the most part, but I also think there was a part of me that just wanted to challenge myself and see what I could do on my own. As I mentioned above, my frustration at seeing others getting credit for my design work was actually a great thing. It’s what gave me that extra push to branch out on my own. Plus, I had some great experiences working with fantastic people who helped me hone my skills and gave me the opportunities I needed to build my confidence.

What advice would you give someone who has a hobby or pastime that they absolutely love but is reluctant to do it for a living?

For me it was taking baby steps mixed with a little grit and fearlessness! I think of myself as being a little timid, but then there’s the part of me that just throws caution to the wind. I’m also big on picking other people’s brains and asking for help and advice from anyone and everyone. My first step was signing up for a local art fair, which at the time, was a huge step and definitely scary! But I talked to the show director on the phone for nearly an hour before actually taking the plunge and she was happy to share her experiences and perspectives, and even critique my art. She helped me feel more at ease. I had some success at the first show which helped build my confidence and things got easier from there. What I mean by “easier” is that it was easier for me to keep moving forward. I wasn’t as nervous. I started realizing that my art could actually become a business! I still wasn’t sure how, but I felt it in my bones!

It’s said that the quickest way to take the fun out of doing something is to do it for a living. How do you keep from changing something you love into something you dread? How do you keep it fresh and enjoyable?

I’d be lying if I said that it’s all fun. I work longer hours than ever before and have to wear so many different hats. It’s crazy sometimes! But because the business is basically about creating art, staying fresh is just a natural part of the business. Designing a new piece or coming up with a new product concept is what keeps things fun for me! It’s always exciting to put a new product out there and see what happens!

What is it that you enjoy most about running your own business? What are the downsides of running your own business? Can you share what you did to overcome these drawbacks?

I love being in control of the design process and being able to make decisions and not being dependent on someone else for my livelihood. This is also the downside for me. The hills and valleys are more intense. When you are dependent on yourself and your decision, the highs — the successes — are really exciting! But there are also the lows and they can be intense too — worrying about market fluctuations and keeping the ball in the air all the time and getting everything done, etc. My family helps keep me grounded when I’m soaring or sinking! For me, it’s important to keep things in perspective and live in the moment as much as I can.

Can you share what was the most striking difference between your actual job and how you thought the job would be?

The biggest difference is the time I spend on work. It’s basically 24/7. Many people think that when you have your own business you can set your own hours and have more free time. I really think it’s just the opposite, at least for me. There’s really not much down time. If I’m not actually at work — in the studio or at the computer, etc. — I’m thinking about it! It’s always on my mind. Maybe that means I love it? Ha, who knows!

Has there ever been a moment when you thought to yourself “I can’t take it anymore, I’m going to get a “real” job? If so how did you overcome it?

Not really. Of course there are always moments when I feel crazy and overwhelmed and question what in the world was I thinking! But, so far those moments pass quickly. Since I had a “real” job for 10+ years prior to starting this business, I’m committed to doing my own thing more than ever! While I loved the people I was working with, there were the frustrations of being told what to do and when to do it and how to do it and so on. I now thrive on being able to direct my own creative process. I feel like I live the quote about either following your own dream or helping someone else follow theirs. I’m definitely following my own path, so it’s sink or swim, but I love the challenge! When I feel a little overwhelmed with it all, I remind myself how lucky I am to be able to make my own decisions and be in control of my own work life.

Can you share the most interesting story that happened to you since you began leading your company?

We received an e-mail a while back from an editor at HGTV Magazine saying that she’d bought an item from us and was going to include it in a story in an upcoming issue. She wanted our info to include. Needless to say we were super excited but also baffled about when and where she’d bought the item. We searched our records and discovered that lo and behold we’d shipped something addressed to the HGTV Publishing headquarters in New York and never even noticed it! We ship out a lot of items everyday and generally don’t notice names and addresses on shipping labels. Lesson learned! We look now!

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

We laugh every time we think about how excited we were to make our first online sale after launching our website store. After celebrating, we then realized we had to actually ship the darn thing! Our first few attempts at packaging were a little less than impressive. For the first few months, I calculated package weights by weighing myself on my bathroom scales and then picking up a package and weighing myself again and subtracting the difference. Not the most efficient way to do things for sure!

Needless to say, our shipping practices have come a long way. We now have professional scales and spend long hours everyday packaging and shipping items with daily postal pick-up at our location. No more trips to the post office! And we now buy boxes by the semi-truck load!

Who has inspired or continues to inspire you to be a great leader? Why?

I don’t think of myself as a leader per se. I work with my family and we’re all a team. We’re all leaders in one way or another!

How have you used your success to make the world a better place?

I can’t say I’ve made any conscious attempts to make the world a better place, but I feel strongly about running my business in an honest and open way. And, I hope that my art brings a little bit of joy to those who receive it.

What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

  1. You will work harder than you ever have in your life! As I mentioned above, there’s very little down time. Ideas — and worries — come day and night if you are passionate about making it all work! At least that’s the way it’s been for me.

What person wouldn’t want to work doing something they absolutely love. You are an incredible inspiration to a great many people. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger.

I think everyone has a creative nature, although many people don’t think of themselves as being creative. If I could inspire a movement it would be to help everyone discover their own unique creative talents. For me, creating is what makes life fun and challenging.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“Take time to do what makes your soul happy.” Art makes me happy and I’ve been fortunate to be able to turn it into a business I love!

Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

Chip Gaines, and of course Joanna too! Obviously, I admire them because of all their accomplishments in the home decor and decorating arenas and of course home building/remodeling, which was something I lived first hand throughout my childhood via the family business. I say Chip first because I read that he had a learning disability and felt that it gave him perseverance. I can completely identify with this.

I was diagnosed with dyslexia at age seven, which obviously affected my course throughout childhood, although it wasn’t something I focused on. It’s just the way I was/am. Of course, there are always those that will look down on people who are different and struggle with reading, etc. but I recently read that three of the six Shark Tank cast members are dyslexic and actually consider it to be an advantage for entrepreneurs. You often have to work a little harder and be more flexible and be willing to ask questions and to ask for help. These are all traits that most entrepreneurs share, they said. I agree completely!

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.


Phil La Duke is a popular speaker & writer with more than 400 works in print. He has contributed to Entrepreneur, Monster, Thrive Global and is published on all inhabited continents. His most recent book is Lone Gunman: Rewriting the Handbook On Workplace Violence Prevention listed as #16 on Pretty Progressive magazine’s list of 49 books that powerful women study in detail. Follow Phil on Twitter @philladuke or read his weekly blog www.philladuke.wordpress.com

Authority Magazine

Leadership Lessons from Authorities in Business, Film, Sports and Tech. Authority Mag is devoted primarily to sharing interesting feature interviews of people who are authorities in their industry. We use interviews to draw out stories that are both empowering and actionable.

Phil La Duke

Written by

Author of “I Know My Shoes Are Untied. Mind Your Own Business” and “Lone Gunman. Rewriting the Handbook on Workplace Violence Prevention

Authority Magazine

Leadership Lessons from Authorities in Business, Film, Sports and Tech. Authority Mag is devoted primarily to sharing interesting feature interviews of people who are authorities in their industry. We use interviews to draw out stories that are both empowering and actionable.

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