It was right around this time of year in 2015 that I came to the exciting, yet terrifying decision that I was going to quit my job to start my own business. 

When I tell people my story, the first question they ask is: “How did you know it was the right time to quit your job and make the leap?”

It’s a difficult question to answer because the truth is, there’s never a good or right time to make a big, bold move.

You could easily put off your big, scary goal forever, and truthfully, no one would probably blame you.

But that’s no fun, right?

Instead, I chose to stop trying to figure out when the time was right. I took the wise advice to “Leap, and the net will appear”, trusting that with the pieces I already had in place, I’d be able to figure out whatever it was that came my way.

The pivotal lightbulb moment

Despite all of that, I actually did experience a bit of a lightbulb moment that helped set the train in motion.

Here’s the scene: It’s an ordinary October Thursday in 2015. I’m driving two hours to another part of the state for a work meeting. I’m pulled over on the side of the turnpike taking a catch-up call with my boss, jotting down notes and to-dos from our meeting that happened to take place during the middle of my drive.

In that moment, I felt like crap. I felt scattered, stressed and unhappy. After all, each day I was waking up at 5 a.m. to complete blog and client work before heading to my 9-5. Most evenings, I’d teach yoga, leaving little time for a social life, or other important stuff like sleep.

After the mid-drive meeting with my boss, I called a friend who runs her own business to vent about how stressed-out I felt. 

“Jess, what are you doing?” she asked. “Quit your job. Take your business full time. You can do it. I believe in you.”

She (and others) had said these words to me a thousand times before, but in that moment, they struck me differently.

The conversation changed everything. From that moment on, I couldn’t get the idea of quitting my job to start my own thing out of my head. I started to seriously plot and plan.

After that, it was challenging to find the right time to actually say the words out loud. When you have no other job waiting for you or someone setting a deadline, it’s hard to know when the time is right.

Finally, in mid-December, I decided that there was no time like the present. What was I waiting for?

Every day I put off making the decision, I started to feel worse and worse. Finally, one Monday in December, I said to myself, “This is the week. Wednesday is the day.” And I woke up on Wednesday, went into work and gave my notice.

The nitty-gritty practical stuff

OK, so that story is lovely and all, and yes, it was a bit of a lightbulb moment, but it also wasn’t quite that simple.

Quitting a safe and comfortable full-time job to start a business wasn’t something I took lightly.

In fact, the decision was actually seven years in the making, with three years of planning and saving (not yet knowing when I’d quit my job, but hoping that one day I’d make it happen).

Here are three reasons I was confident it was the right time to make the leap.

1. I consistently earned money from my side hustle

Before I ever considered quitting my job to start a business, I rocked a side hustle.

I wrote for various blogs and publications, I brought on my first content management client and I eventually became a yoga teacher, introducing a new revenue stream to my monthly income.

Prior to quitting my job, my side hustle helped me between $2,000 and $2,500 each month from three different freelance clients and teaching yoga.

[If you’re curious about how I find clients, give this post a read.]

I knew that if all else failed, I would at least make around $2,000/month. That certainly isn’t enough money to thrive for a long time, but I knew that it would be enough (especially since I still lived at home then) to buy myself some time to find work.

2. I saved $40K prior to quitting my job (over three years of side hustling)

It turns out that side hustle money came in handy!

Over the course of three years of early mornings and late nights side hustling, I was able to save $40,000 in a backup fund.

I definitely didn’t need quite that much in order to make the leap, but it was an amazing buffer that gave me a lot of security to experiment and not worry about temporary “failure.”

If I were to advise someone else who wanted to quit their job, I’d recommend saving about three months worth of income as a safety net.

3. Quitting my job and knowing that the guaranteed income was going away drove me to work harder

Receiving a paycheck every two weeks is really nice. I certainly missed those paychecks once they stopped rolling in.

But the knowledge that only I could guarantee my income now lit a fire under my booty and motivated me each and every day to get shit done.

Having a bad month work-wise? I wake up each morning a little more inspired to turn it around. Having a good month? I still wake up motivated each morning, pushing myself to break last month’s income or to push for new personal financial records.

No such thing as a right time

It really comes down to this: There is no such thing as the right time. There is no such thing as being 100% ready to take on something

Instead, it’s about preparation and trust.

It’s about doing the work ahead of time and behind-the-scenes to make sure you lay down the groundwork. And then ultimately, it really comes down to trusting yourself, your vision and your work ethic.

If you want to make something happen, you can. If you want to take a leap, you can. 

The time will be right when you do the thing you’ve always wanted to do.

Have any other questions about how I knew it was the right time to start JL&Co? I’d love to answer them in the comments below.

Photo via Pexels

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