When I Knew It Was Time to Quit My Job and Take My Business Full Time

Over the course of my years owning Dri Umbrellas, I’ve asked dozens of founders how they decided to take their business from a side hustle to a full time job. “What was it,” I’d ask, “that made you finally decide to take the leap? When did sacrificing a stable paycheck and health insurance perks like iWatch reimbursement feel worth it to you?”

I was basically asking for a step-by-step “Leaving Your Job for Dummies” manual, but I walked away from every conversation more confused than certain. Answers varied in length and the amount of consideration that actually went into the decision. A few examples:

• “I walked straight across the stage at business school graduation right into entrepreneurship. I was broke as a joke and didn’t even apply for jobs.” 
• “As soon as my partner got a job that covered us, I was out of that hell hole!”
• “I left my 9-5 as soon as I couldn’t manage both.”
• “I got let go from my job so I just focused on building the business instead of finding another position. Don’t tell my wife.”
• “I started my extremely successful world-dominating business from a garage with my partner, Steve Jobs.”

The conversation would carry on, and I’d find myself saying things like, “That’s so great! One day when I go full time with Dri Umbrellas, I’ll be able to eat lunch too!” or “One day I’ll work for myself and I won’t need to schedule pee breaks either!” Then, on a random Tuesday a few months ago, it hit me. I’d never decided when “one day” would actually be.

I initially thought I’d wait to leave my full time job until Dri Umbrellas hit a specific amount in sales. How much? Couldn’t tell you - I never decided what that amount was. Alternatively, I said it could be when I had a specific amount of savings. What was the exact amount? No idea - never decided. Maybe, I thought to myself, I’ll set a specific date and time! Did I actually decide on a date? Of course not! My target timeline for turning my passion into my profession was murky at best, non-existent in truth. My series of non-decisions had made the day I’d work for myself an elusive target that even Katniss Everdeen couldn’t hit.

So when did I know with absolute certainty it was time to quit my job and go full time with Dri? My answer is even more annoying than Steve Wozinak’s (who I 100% did not speak to, by the way.)

I didn’t. I just got super freaking sick of hearing myself say, “One day…”

Now I didn’t entirely throw caution to the wind. I enjoy being married, so I made sure the math mathed and that my husband and I wouldn’t have to eat ramen noodles for every meal and our doodle wouldn’t need to hunt for her own dinner (as if a doodle hunting anything is possible), then I set my last day at my job. Making this huge decision in a thoughtful manner gave me the confidence to give my notice without ever second guessing myself. The day I told my amazing boss I was leaving I was proud, terrified, excited, and brown-paper-bag-hyperventilating anxious. But I was also certain. 

So to those of you side hustling with dreams of going full time, but only vague “plans” on when you will - I encourage you to question your reasoning. Why aren’t you full time today? And when will it be your time? What’s your yardstick? Money saved? Sales earned? When is your “one day”?

I’ve been self-employed for one day, and I can already promise you it’s a question worth answering.