When Can I Quit My Day Job?

Is there ever a “right” time?

When I got my first job after of college, I was really, really pumped.

After all, I’d landed a job with Manager in the title that I’d start the week after graduation. It was my first (and only) interview.

The first two years were great. Working for a non-profit, I got to build up my experience and try a lot of different things (a bit out of necessity, due to limited resources all around.)

I created a marketing budget. I spoke in front of large groups. I designed billboards, advertising campaigns, and edited copy for direct mail pieces. I met with legislators. I spoke on TV and radio segments. I gave facility tours.

If I volunteered to do something, I pretty much had free reign to do it — all at 22 years old. It was incredible to have so much room to grow.

But at about the two and a half year mark, I’d fallen into a slump. I felt maxed out with all of the different things I could try and was creatively burnt out.

I’d hit a wall, and even though I still very much loved the mission of the organization, I started to realize there wasn’t much room for growth there.

In my free time, I’d started doing some freelance writing and still had an online business at the time, so I saw the potential for a new path. The idea of working for myself gleamed far off in the distance. It felt unattainable and scary and like something only skilled business professionals could do.

But every morning when I’d wake up, the first thing that would pop into my head was, “When can I quit my day job?”

So I started creating a plan. I needed to find a way to make as much as I was at my non-profit job so I could work for myself and quit my day job (without losing sleep at night.)

The pluses of quitting my day job: No more 45 minute commute each way. No more worrying about having enough vacation time. Creative freedom. Room to grow.

The scary side of quitting my day job: No retirement match. No health care. No steady paycheck.

When I looked at the scales, they seemed to even out.

So how did I know when it was time to quit?

I had started asking around and reaching out to people to see if they needed social media support. I had a lot of experience managing social media presences from my work and my business, so I found a few organizations who were looking for some contractual support on an annual basis. One came up through a casual conversation, and one took some follow-up.

Contract #1: I was offered a full-time position with the ability to work remotely. I went into a meeting with the CEO of that organization and said, “Thanks, but how about contractual work instead?” (I’d been up since 4:30 that morning worrying that he’d say no, be offended, and/or want to stop the conversation altogether.) Instead, he agreed.

Contract #2: I had applied for a contractual position with this organization the year before, interviewed, and then they went another direction. I followed up with them while contract #1 was happening, and it just so happened they were looking for someone in that position again. They agreed to work with me, too.

Just with those two agreements, I’d be making as much as I was at my current job. Sure, I’d still need to pay for health insurance, retirement, etc., but I could supplement my contractual work with more freelance writing.

I talked it over with my husband, and we decided we could make it work.

I could quit my day job.

I gave three weeks notice, and in November of 2013, started Lumen.

The first few months took some getting used to. I had to find my routine while working from home, find an accountant, figure out my retirement planning, and balance this new flexibility.

I worked really, really hard that first year. By November 0f 2014, one year later, I’d gone from those two annual contracts to working on a monthly basis with more than 14 different businesses — writing for them, helping craft website copy, and managing some social media campaigns.

Referrals helped me meet new clients, and today, the business is still growing.

I’d quit my day job…and made it out alive.

So how do you know when it’s time to quit?

I think it depends on a few things. If you can answer yes to most of these questions, it’s time to start seriously considering it.

  1. Have you maxed out your growth opportunities at your current job?
  2. Do you have enough income lined up to maintain your quality of life?
  3. Have you created a business plan with a strategy for how you’ll operate and grow your new business?
  4. Do you have mentors you can call on when you need help troubleshooting?

I don’t think there’s ever a time when you know 100% that you’re ready to quit your day job. It’s always going to feel scary. But if you can cover those four bases, you’re in a good place to take that first leap.

With that being said, it’s never a good idea to quit your job just because you don’t like it anymore.

You need a plan. You have to be prepared for a lot of uncertainty, but approach it with a business mind.

Take the time to think it all the way through. Stay up late. Do research. Ask other business owners how they got started. Take notes.

And yes, you need to go through and build an entire business plan. It will help account for all of the variables that can trip you up along the way and make you think long and hard about if this really is a good idea.

But when the time is right, don’t hesitate. Go full speed ahead and challenge yourself to exceed your first year goals.

If you can do that, you’ve fully earned the right to quit your day job.

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