Transitioning into Entrepreneurship: Leaving Your Day Job on Good Terms

Katie Stack’s studio, Stitch & Rivet.

Photo by Victoria Milko

Leaving a job is never easy. Even if you’ve carefully planned how you’ll give your notice and you anticipate it with glee, it can still be an uncomfortable experience. Like a child awaiting the tooth fairy, you have to go through the painful process of detachment before you can reap the benefits. And as an entrepreneur, it’s a bit more nuanced than just giving two weeks’ notice, because you aren’t simply leaving for a new job — you are leaving for a new life.

I resigned from my job, I gave two weeks’ notice. It was a very annoying two weeks because I had so much ahead and so little to keep my attention at work. The reason I gave? I’m moving to Berlin. It was an easier thing to say than the truth, which was: I’m going to travel, with a month stay in Oaxaca and a few months in Berlin, to do research and grow the side-business you know I’ve been running outside of work, and I might move to Berlin afterward, but I don’t know yet! My decision to keep my reason simple, if a bit ambiguous, was my way of saying: “I’m leaving. It’s non-negotiable and for reasons beyond this job.” Which was true, even if it left out a lot more.

I also figured that my employers would be more understanding if I framed my decision as a necessary component of my move, instead of me leaving to do my own thing. I felt like I would be betraying them somehow, or that it might come off as irresponsible, flighty, or even stupid (I had a pretty good salary). Yet Mike Kohn, Director of People Operations at Sparkfund, an energy equipment company, says that simply saying, “I’m leaving to start my own business” is perfectly acceptable.

According to Kohn, who’s worked in the human resources field for George Washington University, SmithGroupJJR, and Deloitte, what’s generally accepted upon resignation from an employer is the following: you give notice, you appropriately hand off your work, and you help with the continuity of work as much as possible. If one doesn’t follow these standards, it’s possible to burn bridges upon leaving a job. Leaving on good terms is always a good idea–you never know when your roads might cross again.

Resigning may be pretty straightforward, but what about the lead up to the actual act?

When have other entrepreneurs left their day jobs to do their own thing, and importantly, how did they know it was time?

Katie Stack, owner of Stitch and Rivet, had been operating her business for nine years when she decided to leave her day job managing a department in a professional costume shop. She left because she felt her day job was getting in the way of the success of her business. Stack says her immediate boss gave her a heads up when her job faced some budget cuts. She was then able to give a few months’ notice and conclude her job at the end of the season.

Stack suggests talking to a financial advisor, which she and her husband did before she left her day job. Says Stack, “Lay all your cards out on the table and be honest. You might find out you are in a better position than you thought.” Stack now has four employees at Stitch and Rivet and continues to run her business full-time.

When faced with an office culture that she no longer connected with, Mallory Nezam also realized it was time to go. Nezam had been running her business for four years, and had more opportunities going on outside of her day job.

Katie Stack, owner of Stitch & Rivet.

Photo by Victoria Milko

“It was like they my company started to outgrow and over shadow the day job,” says Nezam, who was working in marketing at the time. “I also didn’t like sitting at a desk all day”.

Nezam suggests the following when leaving your job:

“Build a little before so you have some momentum, because it can feel scary to cut the cord. Save a little money and surround yourself with a supportive community if possible. Get a co-working space so you aren’t alone all the time.”

Mallory Nezam.

Photo by Adrian O. Walker

Another entrepreneur, Noelle Hozumi, was working in banking when she left her job to open a restaurant. Hozumi says she hadn’t started her new company when she left her day job, but she knew it was time to leave when her job began to affect her health. She says she was successful and progressing at her job, but it was making her moody, sick, and stressed. Worst of all, she was uninspired. “I was ready to take a leap of faith and go off the expected path,” says Hozumi.

Hozumi’s advice: “Save up. Make a plan. Set a date to leave, and do it!”

Katrina Johnston-Zimmerman also left her job before starting her own business, but she had started marketing herself on social media and launched a podcast with the same theme as her work. She decided to leave when she realized that her gender prevented her from being taken seriously at her firm in the real estate industry. She had revealed to a colleague that she wanted to leave if things didn’t improve, and was actually offered severance during her review if she agreed to leave to start her own business.

“Don’t wait until you’re unhappy and lose sleep over your performance. Take note of the early warning signs and prepare for launch — you got this,” says Johnston-Zimmerman, who now runs her own urban anthropology consulting firm.

Every entrepreneur has her own path, and leaving a day job may be a necessary step along the way. By being prepared, honest with yourself and your employer, and following the expected protocol, you can ensure a smooth transition into working for yourself.

Katrina Johnston-Zimmerman

Stephanie Echeveste

contributor

Stephanie is the founder of cocktails+craft. She recently left her full-time job to be an entrepreneur. She has helped grow various e-commerce businesses, including Nesting Days (baby carriers), Betabrand (clothing), and 2U (master’s programs). She enjoys fiber arts and printmaking, while sipping a mezcal negroni.