Mailbag: Should You Quit Your Job Without a Plan?

You all know that I love to answer questions that are sent to me. I love this one because it speaks to me. It’s something we all face when we start freelancing.

When you decide to start freelancing, should you quit your job without a plan? So, let’s talk about it.

The answer is…what’s your life like? What’s your network like? What does your tolerance for risk look like? And what does your savings account look like? Don’t worry, we’ll get into more details.

Should You Quit Your Job without a Plan? In My Opinion? No

I’ve felt this way since before the current state of affairs with the economy. And, yes, some people do make it when they quit their jobs without a plan. I will highlight one toward the end of this article. With that said, there are many factors that determine once someone has had enough and up and quits or makes a plan to start a business as a freelancer and has no plan or resources.

I started my business (part-time) nine years ago. It will be a full-time nine years in the summer of 2023…early summer. Anyway, I realized in 2013 that I needed to figure out a way to make working from home a reality for me…and I felt like I didn’t have much of a choice. It wasn’t some sort of romanticized idea. I needed a way to support myself and my family, not worry about the youngest child (who was about three at the time and nonverbal, recently diagnosed then with autism), and also not worry about the ex trying to get me fired. I live in a state where it is perfectly legal to get fired if you’re a survivor or victim of domestic violence. So, I taught college part-time and worked as a real estate paralegal part-time. Teaching wasn’t viable since the ex kept calling and I had to keep defending myself to my boss. It also didn’t pay well. I liked the small law office I worked with, but I didn’t want the same situation, the drive was crazy, I had Uriel to worry about (and my other two sons…but again – Uriel was and is nonverbal), and even with a college degree in Paralegal Studies and over 15 years of experience, I couldn’t make enough to support my family like I wanted. And I wasn’t looking for six figures. I just didn’t want to worry about which bill I wouldn’t pay so I could pay something else.

Related: The Day I Knew I Had to Start a WFH Business

My Plan to Quit My Job and Work from Home

Having three kids and a spouse (he worked when I didn’t but we always wanted someone home with Uriel), I wasn’t one for taking a big risk. I’d already had my very first Upwork job…back then, it was oDesk. I had my profile there, eLance, and PeoplePerHour. I had an account on Freelancer, but all I ever found there was spam.

My initial plan was to start part-time. That was like having three jobs. I worked in the early mornings (sourcing clients or working on client projects), after I got home from work, after the kids went to bed, and on weekends if we didn’t have family plans. And, yes, I know…a lot of you think that doesn’t sound like fun. If, though, you want to make a work from home business your reality, it does require that you commit to it just like you would any other business. The only difference is where you’re officing.

As the business grew, I made the decision to leave the college at the end of the term. That gave me more time to source work, work on projects, or, if necessary, I could go into the law office for extra hours. The office I worked in was nice because the owner didn’t care if I worked on my own stuff (we had that talk) as long as everything was done.

I knew it was time to leave the law office when I did the math on the work I had to turn down because of working in the law office and it was more money than what I made. However, the key about that was the job offers/invites were coming in consistently. Otherwise, my few clients I had were asking me, “Hey, can you also do X?” The answer was yes, but the deadline was prolonged because of my day job that they knew I worked.

I gave the law office notice and helped train the new person. I also helped the owner get better acquainted with his own legal tech. He was terrified of technology. By the time I left, he could get into his own email and print them. That may not seem like much, but it was huge for him.

It Worked, But It Wasn’t Always Smooth Sailing

So, my plan worked…but that didn’t mean that the last nine years (almost) have been nothing but smooth sailing. I had some management experience, and I’d run a small business of my own before. It was overwhelming, though, because this was now our bread and butter. Failure wasn’t an option.

But I did not know how to handle certain things…like dry spells (I rarely have those now), bad clients, good rates, raising rates, advertising myself…the list could keep going.

Related: Freelancers: Start Your Holiday Planning NOW

The worst of it for me, especially in the beginning, was the dry spells in work. The first year or two, it was always near the holidays. Because I hadn’t pre-planned, gotten extra clients (I was new), and I hadn’t priced appropriately (I had a plan there…and it did help me get started but…it had its drawbacks), I was freaking out when things when quiet. How would we buy groceries? What about electricity? What about Christmas for the kids? And we aren’t extravagant people.

We always made it. My husband would get extra contract jobs if necessary or he’d teach private jiujitsu lessons. But we would talk through my anxiety and we would work together (my husband is also super smart) and within a couple of years of that, I figured out how to pre-plan for the holidays, raise my rates, and all the good stuff.

So, as you can see, at least in my opinion, it’s always about planning…executing…and setting up another plan.

There Are People Who Succeed without a Plan

I’ve had people ask me if they don’t have a job and can’t find a job, what about then? Now, I know this isn’t quite the same as quitting a job without a plan. Since it’s still something I am asked, here are my thoughts.

1. Determine your risk tolerance.
2. How long can you survive if you don’t have a stable income?
3. While you build your business, are you willing to do whatever you need to do if you have bills come up? Could be a temp job…could be (I’m writing this in November 2022) gift wrapping at the outlet mall… Could be cleaning. I don’t know – whatever you need to do to bring in some money.
4. Do you have the self-determination necessary to “burn the ships”? If you don’t know what that means, In 1519, when Cortes landed in Mexico, he didn’t want his people to turn back. So he sat all the ships on fire.

Of course, if it turns out you hate working from home or freelancing, that doesn’t mean you have to do it forever. I’ve said it hundreds of times here on this site: both freelancing and working from home aren’t for everyone. It doesn’t make you a failure if you don’t enjoy it. Just remember that one bad day or a bad stretch of time (I’ve had both) doesn’t mean you suck or your business sucks. That’s not necessarily a sign to shut it down.

Morgan Overholt: Graphic Designer, Blogger, Freelancer Extraordinaire

If you follow me on Twitter, then you know I’m a bit of a Morgan fan girl. She’s very successful as a graphic designer, blogger, and all around freelancer extraordinaire. And she rage quit her job without a plan…then started freelancing. So, quitting your job without a plan can work. One thing that’s different about her story is that, as her article states, she had a general idea of what she could do after quitting. She also knew it would be a lot of work…but the work paid off for her in a big way.

So, whether your quit your job without a plan or with a plan, at least having an idea of what’s next and that you’re prepared to put in the work to get there (along with risk tolerance) is key.

Robin Bull

You may not know me by name but you know my words. I've helped you connect with clients, educate audiences, and inspire loyalty. And I also LOVE helping people work at home, whether they are stay-at-home moms, retired professionals, or folks with disabilities.