Seller Handbook

Advice and inspiration for successfully running your Etsy shop

Seller Handbook

5 Telltale Signs You're Ready to Quit Your Day Job

Are you gunning to become your own boss? Before you take the plunge, hit up this checklist to ensure a fearless (not reckless) approach.

By Cheyne Little Aug 27, 2013
Photo by Aisling Designs

So here you are, loving (just about) every minute of running your creative business and finding yourself thinking more and more about taking the leap into full-time self-employment. But how do you know when it’s the right time?

Before coming to work for Etsy full time, I was thrown into two years of running my own sewing business (making and selling handbags on Etsy and through wholesale) when my previous company was forced to shut its doors unexpectedly. For me, striking out on my own was as simple as recognizing that one door was closing and preparing to walk through a new one. For others, it can take years to build the resources, skills, and courage — and that’s totally okay. I asked a few current full-time Etsy sellers about how they prepared to quit their day jobs. Together, we came up with these five telltale signs you’re ready to make your business your main squeeze.

1. You’ve Got a Plan

When Lauren Felker of HaddonCo had her first son, she felt that cute clothes for little boys were tough to find so she decided to create and sell her own. Working with her husband Neal, she spent countless hours researching her target market and developing products just for them. “It’s hard to grow a business without a plan,” she says. A business plan or set of solid goals can be the map that guides you out on your own. It can help you make tough decisions and tell you how to spend your very valuable time.


Whether you produce a traditional business plan or create (and achieve) a series of attainable milestones for sustainable business growth, goals are important guiding signposts. To begin solidifying your next steps for long-term success, read a variety of perspectives in these Seller Handbook posts: How to Write a Creative Business Plan In Under an Hour, Why Done is Better Than Perfect, and Ready for Etsy Success? Start With an Etsy Goal.

2. You’ve Saved Up

“Though I dreamed for years about quitting my day job, when the opportunity presented itself I wasn’t prepared financially,” shares Kerri Testa of kerriannshop, an accessory shop based in Massachusetts. “If I was to go back, I would have paid off debt when I started daydreaming.”

Kerri Testa created her line of cell phone wallets with purpose and passion in mind. Read more via her shop’s About page.

Taking a long, hard look at your expenses, your current profit, and plans for growth is vital to maintaining your self-employment without working yourself (or your bank account) into the ground. You might find that your business plan calls for outside investment, a five-year savings plan, or just a few months to squirrel away some spending money. Five Money Questions to Ask Before Quitting your Day Job gets to the heart of the matter.

3. Your Business Is Legit

For Ashley Pyles of AshleySpatula, obtaining a business license was one of the first steps she took in opening her Etsy shop. “I did my taxes and pricing research to make sure everything was in line and I could make sure I made a profit,” says the jewelry seller who quit her day job as a barista in 2010.


Lucy and Ryan Berkley of Berkley Illustration say that, were they to start all over again, they’d have taken a business class or two. “Bookkeeping is not our strong suit,” Lucy says. “We've crafted our own little system, but I'm sure we could be more efficient and organized in that department.”

Read more of Berkley Illustration’s story in their Quit Your Day Job feature.

Talk to an accountant and take the steps to follow local business and tax policies to make the transition from part time to full time as smooth as possible. Learn more about legal structures in Law 101: A Guide to Setting Up Your Business, and also consider protecting yourself and your business with insurance.

4. You Know Your Resources

Organizations like the Small Business Administration and SCORE offer all sorts of assistance and free tools to help you and other small-business owners navigate uncharted entrepreneurial waters. Virtually every day, there are new tools and services created to make running small business easier and easier. Local Etsy Team members also can share their experiences and point you in the right direction to file for that business license you know you need to get. And don’t forget your personal network of mentors, colleagues, friends, and family.

5. You’re Mentally Prepared

While all of those other details can seem like a mountain to climb, you need to realize that you’ll be the one climbing it. The one aspect you’ll deal with the most, day in and day out, is you.

Cheyne Little works in her Texas-based studio back in 2011. (Photo by Brandy Frank)

Know yourself and your expectations. Because my previous employment involved meeting and chatting with hundreds of people a day, it was a shock to my system to work for days at a time in my studio, only speaking to the postal carrier. If I were to do it all over again, I would explore shared studio spaces and other ways to stay in touch with my fellow Etsy sellers. Not everyone is an extrovert; define your style and make it work for your business.

Even if your daydream version of self-employment matches reality, self-employment requires specific skills. “When running a small business from home, you have to be focused and driven, but most of all, you have to be flexible,” says Ashley Pyles. Do you have the self-motivation to make your time in the studio as valuable as possible even when you’re not feeling so creative? How about the organizational skills to juggle 20 open orders a day? Use your current job as an opportunity to hone those skills and practice staying in a healthy headspace.

And, finally, prepare for a graceful departure from your day job. If you’re thinking about how much you’ll relish an extravagant exit (á la Jerry Maguire), you should revisit some of your motivations for leaving. Aim to leave your job with your boss and coworkers totally on board — not totally turned off about how you departed.

So when do I think the right time to quit your day job is? When you know the time is right for you. Trust your gut. Be fearless, not reckless. Don’t avoid topics and steps that make you uncomfortable; learn about them and meet them with open eyes.

Do you want to quit your day job? How and when do you plan to take the plunge? Share your thoughts in comments below.


Cheyne Little

Cheyne Little is Senior Product Educator at Etsy. Before joining Etsy as an Admin in 2011, she worked full-time on her accessory line and on the leadership team of her local Etsy Team in Texas.


Continue reading in Growth strategies