Life & Business

Moonlighting: Starting and Managing a Creative Side Business

by Lauren Chorpening Day

When taking the jump from employed with benefits to full-time freelancing, you always hear that there will be some long nights and work on the weekends. Creating a work/life balance is hard enough when your creative business is your 9-to-5, but it seems almost impossible when it has to be worked around your day job. Lisa Wong Jackson has a full plate — she has a full-time position as a senior graphic designer, she is married, she is the mother of two boys, and she is the founder of a successful stationery and design business out of Berkeley, CA called Good on Paper. Her schedule is booked.

Today Lisa shares her best advice for those wanting to keep their day jobs while moonlighting after-hours. From knowing when to say “no” to projects, to crunching the numbers, to finding time for family and rest, Lisa’s authentic and learn-as-you-go attitude is inspiring. Click through to read her story and glean from her experience as a successful moonlighter. –Lauren

Product photography by Lisa Wong Jackson
Portrait photography by Sarah Hebenstreit

Why did you decide to start your own business, versus work for someone else?

I’m a senior designer at a large architecture and engineering firm three days a week, which is my “day” job.  I started Good on Paper as a freelance design business so that I could take on more creative projects. In addition to design projects, I also have a line of stationery. When I got married in 2005, I designed our wedding invitations, and for the favors I designed a set of note cards for each guest. I received a lot of compliments, and my friends and family encouraged me to start my own line of stationery. I initially started out with a line of about a dozen cards, selling them at small craft shows. I eventually made it to the National Stationery Show in New York, where I was able to meet many of of the designers I admire and also made some amazing friends.


Can you remember when you first learned about your field of work? How did you discover what it was, and how did you know it was what you wanted to do?

I was fairly creative growing up, but I didn’t think I would end up with a career in a creative field. I have a passion for the environment as well. I majored in Conservation and Resource Studies at Cal and minored in Business Administration (which I thought was the practical thing to do). I ended up interning at an environmental consulting company in their Marketing and Business Development Department, working there through college and after graduation. I found myself really interested in graphic design, which led me to the graphic design certificate program at UC Berkeley Extension. I loved every aspect of it and knew it was something I wanted to do for a living. 

What was the best piece of business advice you were given when you were starting off?

Hire a bookkeeper so you can focus on your work and not have to worry about crunching numbers all the time. I’m so grateful that one of my closest friends does my bookkeeping — it has helped me tremendously, not just for my business, but for my sanity!

What was the most difficult part of starting your business?

Managing the day-to-day operations was difficult at first, until I got a bookkeeper. Nowadays, juggling various obligations is a constant challenge: Designing for individual clients, designing for Tiny Prints/Shutterfly/Wedding Paper Divas, blogging, contributing to the Oh Happy Day blog, and the hardest job of all, parenting. The hardest part is deciding what projects NOT to take on, and being [okay] with that. 


Can you name the biggest lesson you’ve learned in running a business?

Sometimes you just have to say “no” and turn projects down even if you think it’s “worth it.” I tend to say “yes” to a lot of projects, and more often than not, it ends up stressing me out. With everything else I have to juggle — my two kids, their school, activity schedules, work, keeping up with housework — I could and should say “no” more often than I do.

Can you name a moment of failure in your business experiences that you learned from or that helped you improve your business or the way you work?

Luckily, I haven’t had any catastrophic business failures, but I do recognize that I periodically take on too many projects and end up working super late, which isn’t good for anyone — me, my kids, my husband, or my clients. I’m now trying to be more mindful about how much I take on and what I can let go, and that’s helped a lot.

If you were magically given three more hours per day, what would you do with them?

Oh wow, what a luxury! I would split that up and sleep in until 8, spend an extra hour with my kids and husband, and make some more time for exercise or just plain relaxing and catching up with magazine reading. 


What has been the biggest sacrifice you’ve made in starting your business?

Probably sleep! When I only had my other job, I would work the typical 9-to-5 day. When I started Good on Paper, that meant working at nights and weekends to get things done. Then two kids came along, which meant working when the kids were asleep. As tired as I am, one of my favorite parts of the day is just relaxing and watching a show with my husband after I’m done with my work for the night. Note: this only happens about 2-3 times a week.

Can you name your greatest success (or something you’re most proud of) in your business experiences?

This might sound cheesy, but my greatest success is when a client is really happy about the work I’ve designed for them and sends me a sweet note.

What business books/resources (if any) would you recommend to someone starting a creative business of their own?

Not just saying this because I heart Design*Sponge, but this Life & Business column is such a great resource for anyone looking to see what it takes to start a creative business. I’d also recommend listening to Jennifer Snyder’s weekly interview series called Creating Your Own Path. Another book I’d recommend is Craft, Inc. by Meg Mateo Ilasco


Has failing at something or quitting ever led to success for you? Walk us through that.

I started my stationery line about 10 years ago, and I’ve been in the process of closing up the wholesale and online stationery shop. (You can currently find clearance-level deals on all stationery in my online shop). While I wouldn’t call it quitting, I just realized that it takes too much time and money to design, print, package, market, and ship stationery products. Phasing out this part of my business has allowed me to devote more of my time working on custom design for clients, designing custom party invitations, and blogging.  

In your opinion, what are the top three things someone should consider before starting their own business?

1. Be ready to sacrifice personal time — owning your own business means working more than a typical 9-to-5 day. (But hopefully you will find it more rewarding!)

2. Financial stability can be a challenge — freelancing often means unsteady paychecks, especially in the beginning. (It’s okay to keep your day job if you can find a good balance).

3. Connect with people in your industry.


What’s the first app, website or thing you open/do in the morning?

I check my email first and delete all the junk, then I like to scan Instagram (my fave!).  

What’s the hardest thing about being your own boss that isn’t obvious?

Knowing when to stop working. At my other job, my schedule is fairly structured and I rarely ever take work home. As my own boss, however, sometimes I feel like I’m working all hours of the day and into the night. I really have to be mindful about turning work off.

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  • Very insightful Lisa. Thanks for sharing!
    I have recently embarked on a similar journey and this has further validated the steps one must take to fulfill their passions. All the best to you and your family!!

  • Great interview! Thanks for sharing all the advice and sharing that weekly podcast. I have subscribed now. I hope it helps me to move forward with my own aspirations.

  • Thankyou so much for this interview – inspiring to see someone proving that it CAN be done and that it’s worth taking the plunge. Especially as someone on the verge of doing just that! X

  • Thank you for this inspiring article.

    I don’t think people really know how hard you have work to make your own business. Indeed it is no 9 till 5 job, but if you ever get the chance to do what you love, it’s so worth it. It takes time to be seen and to be successful, but you have to believe you can and keep your focus on what you want. I finally found balance in my work and home situation, that also took time. But once I found it everything came a little easier.