3 Questions to Ask Before Quitting Your Job to Work for Yourself

by Miranda Marquit · 6 comments

This is my 10th year as a freelancer. I love what I do, and am fortunate to be able to set my own hours and work from anywhere. My situation is a little unprecedented in that I didn’t move from a “real” job into self-employment. Instead, I went straight from grad school into freelancing.

However, I can see where things might have been different if I had started out in a more traditional career and then transitioned into working for myself. In fact, there are times when I wonder if things might have been smoother if freelancing had started as a side gig rather than the “job” I had to make work so my family could eat.

If you wondering if you’re ready to quit your job and work for yourself, here are 3 questions to consider before you make your move.

1. What’s Your Financial Lifestyle?

My husband and I were already living off student loans when I finished grad school, and we moved so he could work on his Ph.D. We didn’t have a lifestyle to maintain because we were already living a “poor student” lifestyle.

If you’ve been working in the traditional sphere for several years, you might be accustomed to certain comforts. Before you quit, you need to know if you can maintain your basic lifestyle, and what you’re willing to give up.

Some of the other financial items to consider before you quit include:

  • Benefits: Don’t underestimate the value of benefits. We never had benefits until my husband started work at a new university in the fall of 2014. I’m amazed at what a difference it makes in our finances. Realize that the things you have been taking for granted — employer-subsidized health insurance, retirement accounts, and paid vacation — all disappear once you leave the traditional workforce. You need to be able to make up the difference.
  • Emergency fund: You should have a solid emergency fund prepared so you don’t have to go into debt in order to meet your living expenses while you transition. Be ready with your cash cushion so you can handle unexpected setbacks, as well as regular costs.
  • Taxes: As a self-employed person, you are responsible for all of your payroll taxes, including Social Security and Medicare. You should make quarterly estimated tax payments, and realize that it’s no longer automatically taken care of for you.

Once you evaluate the financial side of things and take steps to protect yourself, you will be in a better position to quit.

2. Can You Motivate Yourself?

Another consideration is whether or not you will be able to work from home and remain motivated. There are often distractions when you work from home. There are days I find it difficult to get myself going, which makes it hard to motivate myself. But the motivating factor for my husband is that he has to make it in to work because people are counting on him and he has a boss.

When you’re the boss, the story is a little bit different. You might not feel like working, but you need to power through anyway. No one is going to mark your time when you come in, so you have to be ready to enforce your own work habits.

Working for yourself requires a great deal of discipline, motivation, and a willingness to accept responsibility when things go wrong.

3. Is Your Family On Board?

If you’re getting started as a young single person, there isn’t a whole lot you have to worry about when it comes to coordinating with your family. However, if you have a life partner, and if children are in the picture, you need them on board with your self-employment.

They will likely have to sacrifice, too, and they should be willing participants. Success when you work for yourself depends a great deal on your support system, so you need to make this a family decision.

Once you have the lay of the land, and are confident that things will work out as they should, you can take the steps necessary to quit your job and begin working for yourself.

Are you self-employed? What are some other factors people should consider before quitting?

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{ read the comments below or add one }

  • Michelle says:

    I have had the hardest time getting my family on board with my choice to work for myself.

  • Michael says:

    Having a passion, actually being good at it, and being able to support yourself with that passion is amazing! When you’re freelancing it’s so important to know what your expenses are and controlling it, more so than when you have a regular job since your income could be erratic unless you can get long-term contracts.

    As you mention in the article, having an emergency fund is so important as well as access to extra cash (like a line of credit) when something goes wrong. As another commenter mentioned it’s important to be able to wear several hats too which makes a challenge but also gratifying for sure.

  • I have been self employed for almost 5 years now and I think that was my greatest decision I have made. Now that I’m working as a virtual assistant, I can handle my own time and also, I have lots of time for my daughter.

  • Michael Kwan says:

    I’ve been a full-time freelance writer for about nine years now. One other question to ask yourself before taking the leap: Are you prepared to wear an innumerable number of hats? I’m a writer by profession, but I’m also my accountant, my webmaster, my IT department, my human resources manager, my marketing department, my social media manager, my office manager, my logistics technician… the list goes on and on.

  • These are all great questions to contemplate before making the break from the cushy corporate job.

    I can absolutely say Yes with out hesitation to number 2 and 3.

    And as to #1, that is being taken care of as we speak. I hope to be able to ready financially to make the break in the next couple years. Until then I will master the blend until I can make the break.


  • Angelica says:

    I’m not there yet but slowly making the transition. I could easily see how it would be hard to motivate myself day in and day out being self-employed. At work, even if you slack off, you still get paid but that’s not the case when you’re your own boss.

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