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So You Think You’re Ready to Quit Your Job for Your Startup?

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Knowing when to quit a full-time job for the startup you’re feverishly building on the side is tough. Even harder: getting out gracefully. Here’s one way to do it right.

By Lorraine Sanders (Contributing Writer, Women 2.0)

For Ali Price, walking away from a three-and-a-half-year stint with microlender Kiva to work full-time on ecommerce site Lydali didn’t happen with a drama-fueled Jerry McGuire- or Steven Salter-style exit of the sort you might envision on the days when you really, really wish you were able to finally quit your job.

Instead, Price took a gradual approach that not only resulted in a stronger company, but also allowed her to remain on solid footing with her former employer and the network she’d built there once she was ready to make the transition into working solely on the startup she co-founded in last year with Lydia Harter.

After hashing out their plan to build Lydali as a new shopping destination for ethically-sourced accessories made by a global network of artisans and craftspeople over dinner one night, Price and Harter knew they were ready to commit and immediately began building the web site. But it took another six months for Price to leave her job with Kiva.

“I would wake up at 6 a.m. to have a call with someone in India. We would be spending weekends shooting products,” Price recalls. “I really liked doing it that way even though it makes for a really demanding schedule.”

As the two moved forward, Price was able to negotiate a part-time work schedule that landed her one day each week to devote to her startup. While the benefits of taking time to test ideas and approaches to attracting customers before leaving a job are obvious, continuing on in her role as a community marketing manager while she spent time building her startup had other perks. When she decided she’d tested and tweaked Lydali enough to confidently leave her job, people on her team were familiar with her project and her enthusiasm for it.

“I had quite a bit of time to let people know across the team and really prepare for leaving and going full-time on Lydali,” Price says.

Instead of the standard two, Price remembers giving about six weeks’ notice that eventually stretched into two months as she finished current projects and helped interview and train her replacement. Since leaving at the end of November last year, Price has worked on Lydali full-time and reports that the company is on track to have its highest-earning month yet in July and just launched a new brand ambassador program.

Still think you’re ready to quit your current job to work full-time on your startup? Read on for more of Price’s advice for early-stage startup founders.

What are some signs that it’s time to leave a current job and go full bore with a startup?

One of the big things is just where you’re spending your time, and what really excites you. If you’re in a job that is just paying the bills, and it’s not something that really gets you motivated and gets you excited, but you’re working on a startup that does, I think that’s super powerful. If that’s where your passion is, then you’re going to figure out a way to make it work. I push people toward the risky side of things.

For example, I’ve known people who are Lyft drivers who are working on a startup and are driving their car at night to make enough money to pay the bills so they can be working during the day on their startup. I’ve known people to work at restaurants or move in with family members while they’re working on something to cut expenses. So I think there are a lot of options for people who don’t have the luxury of flat out quitting their job and not having a salary and living in a city like San Francisco.

What should early-stage founders have in place before making this kind of move?

Having something built out before quitting your job is really important. I would say, as much as you can, test and iterate while you’re still working so you have something you can point to and some proof points before leaving so you have a sense of where you’re going and what you’ll be doing.

How did you break the news to your team?

I had a really good relationship with people on my team, so I was able to broach the subject sooner and more conversationally, so it wasn’t a sudden, I’m out of here kind of thing. I think being able to let people know what you’re working on and why that excites you further in advance so it’s not as much of a shock when you do decide you’re leaving is important.

Once you decide you’re leaving, how can you exit as smoothly as possible?

As much as you can, leave your old job in a really healthy place in terms of having everything ready to go for the next person and having things well-documented. For me, it’s really important to keep doors and relationships open. Leave in a way where you’re not setting anyone up for failure or leaving anyone high and dry. If you have the flexibility to do that, that’s a nice thing to be able to do to keep those relationships really strong.

How did you know you were ready to quit your job?

lorraine headshotAbout the blogger: Lorraine Sanders is a journalist, blogger and media consultant. She is the author of the San Francisco Chronicle Style Bytes column and writes regularly for FastCompany.com and others. She is founder of the blog Digital Style Digest and an inhabitant of the San Francisco Writers Grotto. Connect with her on Twitter @digitalstyledig or @lorrainesanders.