I did it. I mean, I was true to my word. I quit my job of six years and now I’m freelancing. That was over a month ago, and today I still feel great.

At my last job I had great pay, a generous leave package, and the best damn health insurance I’m ever going to have. You might be wondering if I’m crazy to give that up. Maybe, but I was unhappy. It takes a little crazy–and some courage–to escape your comfort zone and live the life you really want. It also takes commitment, planning, a safety net, and, a social support system.

I’m on my own and I’m a major step closer to living my life of freedom. It’s not just because I quit my job; I had a plan for quitting. The first step is to do some soul-searching . . .

Know why you want to quit your job.

I got some great advice from a professor about knowing why you want to do something meaningful. He said, “Be clear on your why, and then commit to it. If you’re not 100% committed, it’s only a matter of time before you fail.” It was probably a way to weed out the poor performers, but I took to heart his point about knowing why you’re doing something life-changing, whether it’s enrolling in graduate school or quitting a job.

There are some questions you should ask yourself if you’re thinking of quitting your job. Barbara Saunders at Empower Work provides a more thorough list, but here are the questions I asked myself:

• What parts of my job do I like, and are they enough to keep me there? I enjoyed the research and writing, but there were other aspects I didn’t care for. They robbed me of my joy, and they took too much time away from the reasons I took that job in the first place. It just wasn’t enough for me to stay.
• What do I hate about my job? Sure, there are annoying aspects of any job. But in my case, the bad far outweighed the good. No need to go into detail here. In the end, the job was no longer a good fit for me.
• Is it because of bad management? The reason many good employees leave their jobs is because of a bad manager. In fact, 79 percent of employees leave because their bosses don’t adequately recognize or appreciate their contributions. However, this was NOT the case for me. I had a great boss, which made it hard to break the news to him.
• Do I still feel connected to the organization and its mission? For a long time, I felt increasingly disconnected from the work and my colleagues. More importantly, my personal values were drifting away from what appeared to be the organization’s values, which told me it was time to go.
• Is this a good time to go? When I decided to leave my job, our country was still several months away from daily Coronavirus updates, social distancing, and hand sanitizer shortages. As we moved into March, I had to consider whether leaving was still a good idea. After reviewing my personal finances, monitoring the freelance landscape, and talking with a few close friends, I still decided to leave. I knew it was slightly risky, but that’s true of most major life decisions.

Once you’re clear about your why, be unapologetic about quitting your job. According to Saunders, this means not feeling guilty about it. No matter how stellar an employee you are, the whole organization won’t crumble to the ground if you leave. If people are disappointed in your decision, that’s their problem. If your working environment is poor, don’t feel bad about leaving your friends behind. They’ll find their way out if they want to, and you’ll support them.

Create a departure timeline.

You’ve decided to quit your job, but when is a good time? It might not be for several months, depending on your personal finances or what’s going on in your life. After I made my decision, I still gave myself four months because I needed my predictable income to pay for a major expense. I’m glad I waited because I had enough time to plan for my transition into the uncertain and precarious world of freelancing.

Once you’ve figured out the timing, go ahead and set a target date. . . Now add more time to that. I’m not trying to be a bummer drag. It’s just that anything worth doing often takes longer than you think it will. Still have your dream “date” in mind, but also create a more realistic timeline to leave enough buffer for unexpected events. Within that timeline, set milestones so you can accomplish some “small wins,” such as . . .

• Submit resignation letter.
• Set personal monthly budget for post-transition.
• Finish report so team can submit it for review.
• Pass off remaining projects.
• Generate freelance writing website and portfolio.
• Select new health insurance provider.
• Go over retirement plan (possibly with financial advisor).
• Negotiate terms for first freelance writing gig.
• Leave job!

As you move through this timeline, think about how you’ll replace your income. Will you live off savings while you look for another job? Do you plan on having a new position in place once you quit? Do you have a side hustle you’d like to convert to a full-time business? Once you figure out your professional goals, build steps into your timeline that’ll help you get there.

Develop a financial plan.

The scariest thing about quitting my job was the uncertainty about my financial future. I was going to lose the best health insurance I’ve ever had, and I knew that my standard of living would go down for a while until I could get some passive income going.

I had to take a look at my budget and figure out how much I needed to earn after I quit my job. In my case, deciding to be a freelancer meant that my income was no longer predictable. Once I knew how much I needed to pay my bills, put in savings, and still have some fun, I could figure out how much freelance work I needed to cover each month’s expenses.

What if I come up short some months? I have enough savings to fall back on. To have any shot at bringing in enough money, I had to diversify my income streams–content writing websites, clients, ad revenue, and passive income (as soon as possible) from selling my content online. I also can take a side job to make up the difference; I’m not too proud to do that.

I also took stock of all financial issues that quitting my job would affect, such as health insurance, retirement savings, and taxes. Since my former employer’s health insurance still covered me for 30 days after my departure date, I used that time to find and sign up for another policy. I don’t enjoy making room in my budget for monthly insurance premiums, but I can write it off as a business expense.

Before I became a freelancer, I always had an employer who matched my retirement contributions each month. I’m still figuring out how to make up for some of those missing funds. I recently met with my financial advisor, who helped me calculate how much I’ll need to put away each month until I can retire.

Stay healthy.

Health and wellness planning is an easy step to miss. If you plan to work from home, it helps to know how you’re going to maintain your nutrition, physical fitness, and mental health, especially if you don’t have colleagues you see every day for social support.

My last employer had workout facilities, and there was a trainer onsite who taught fitness classes and offered individual strength training. For the last 18 months of my job, I worked with the trainer. She must have been a Spanish inquisitor in a previous life; she was that good. Because I’m too cheap to pay for strength training on my own, I asked Torquemada (i.e., secret nickname for my trainer) to help me develop a workout plan at home. She came through. With the exercises she recommended, I don’t need to buy new equipment, and they’re still kicking my butt.

Of course, exercise alone won’t keep you in shape. As a colleague once told me, “You build your body in the kitchen, not the gym.” That said, being at home full-time means I have 24-hour access to my fridge and pantry, which makes it easier to snack or whip up a batch of homemade ice cream. Because I now work entirely from home, I’ve had to be more religious about logging my caloric intake so that my weight doesn’t bloom out of control.

There’s a financial incentive for staying in good health. You’re more productive when you’re in good health. When I was fortunate enough to have paid sick leave, I could stay at home when I wasn’t feeling well and still pull in a day’s pay. If you’re a freelancer and are too sick to work, you don’t make money.

Go out smelling like a rose.

Any job worth having is worth doing well, even if you’re counting the days until you no longer have to do it. Some people say that the way you leave a job says more about you than your first day. I agree. It seems to be common sense not to badmouth your former company, supervisor, and co-workers, but leaving on a good note requires more than that.

I don’t like burning bridges behind me because I don’t know for sure what opportunities might come from my past connections, such as a potential contract or a customer lead. After I gave my notice, I made a plan for how I was going to either finish each project or hand it off, and I gave my supervisor periodic updates on that plan. He seemed appreciative, and the colleagues taking over my projects didn’t feel surprised or overwhelmed by the work I left for them.

Lean on others for support.

Before my departure, I had a handful of co-workers who knew about my full-time RV dream. Once I knew I was leaving, I gradually let each of them in on my plans. I was surprised at how supportive they were. Of course, they were sad to see me go, but they also knew how significant and necessary this life change was to me, and they even offered their support and advice. I knew I could lean on them to discuss the pros and cons of quitting my job.

Conclusion

Quitting a job is not a casual decision, especially if it means making a big career change. You have to know why you’re quitting and be confident when you carry it out. There are financial, logistic, social, and health-related issues to consider, and it will take time to put your plan in place.

The four months I took to quit my job felt like an eternity at times, but I wouldn’t have done it any other way. I knew there was a life of freedom waiting for me. In the end, I made the right decision. I’m not happy just because I quit my job; I’m happy because I did it right–with a plan.