How To Know If You Should Quit Your Full-Time Job And Freelance Instead

We’ve all been told since childhood, “Quitters never win.” But then, what about smoking? Or alcoholism? Or any other destructive habit? Clearly, sometimes, quitters do win.

Wondering if you should quit your full-time job to freelance? You are not alone. Thousands of people are thinking the same thing at this very moment. Even though we constantly fantasize about quitting, fear compels us to stay full-time. Particularly those who have never freelanced before.

For 16 years I moved from agency to agency, always as a full-time employee. I had never freelanced before. Although I toyed with the idea many times (usually because I was fed up with my boss, my employer or my client), I never took the plunge. Then I “got quit” a couple years ago and it was the best thing that ever happened to me.

After a few months I thought to myself, “Why didn’t I freelance a long time ago?” But, of course, I knew the answer. . . I was scared.

My career had been through peaks and valleys, but way more valleys than peaks. Through it all, I always held out, thinking that something great was bound to happen eventually. But nothing really did. At least not to my satisfaction. Except to say I gained valuable experience working with other people and was privileged to work on some big, notable brands. 

The other day, as I was thinking back on my career, it occurred to me that others are struggling with this quandary right now. If you are, read on.

I can’t say freelance is for everyone. I’ve met some people who hated it and others who loved it. The truth is, everyone is different. There are a few factors to consider before you make your decision. Test your situation using the criteria below.


1. Marital status

A lot of people think their marital status or family situation has a lot to do with it. The truth is, it does not. There are plenty of successful freelancers who support families quite easily. The main obstacle for some is the lack of health insurance benefits for freelancers. While that’s true, it shouldn’t be a barrier. You only need to work one or two days of freelance per month to pay for your whole family’s private health insurance plan. Unless you have a child with a chronic health condition, requiring frequent doctor visits, freelancing is totally viable.

2. Personality type

This factor should have more to do with your decision than anything else. Are you a confident/optimistic type or a worrying/pessimistic type? If you’re a worrier, then perhaps freelancing is not for you. 

Then again, full-time employment is not much comfort either. You could be laid off at any moment without warning. At least when you freelance, you become master of your domain and nobody controls your fate but you. To me, that’s more comforting than full-time employment at a company that has little regard for employee loyalty or longevity. 

Also, I used to be a worrier, but now I’m not. Thank you, freelance.

3. Personal experience

It’s true, seasoned veterans tend to get more work. Only because the hiring agency is getting extra “insurance” through their accumulated knowledge of the business. The downside with seasoned veterans is they often have less social and digital experience. 

My advice? 

If you’re a seasoned pro, bolster your social and digital presence. Start a blog, an Instagram or Tumblr page, start tweeting. Package your favorite un-produced social and digital ideas—and put them on your site. 

If you’re a newbie, emphasize your youth, enthusiasm, cultural relevance and hard work ethic. And play up your social and digital chops as well.

That said, it’s really about generating the big ideas, irrespective of the media vehicle. That’s what keeps agencies calling you back again.

4. Brand experience

This seems to be important. Although I’m not positive, because I’ve personally been blessed to have worked on a lot of Fortune 100 brands. So even though I wouldn’t consider my portfolio stellar, I do have notable brand experience, especially in automotive and tech. 

But I know other freelancers who have less big brand experience and they’re doing just fine.

5. Ambition

This is another huge factor. You can’t wait for things to happen, you have to make them happen. The biggest key to successful freelancing is networking. As they say, it’s not what you know, it’s who you know. So get to know a lot of people. Make connections. Also, spend your downtime on personal creative projects. You will be way more fulfilled. 

The second biggest key to successful freelancing is, you must work hard to impress each employer to give them a reason to call you back again.

6. Current financial status

Sadly, some people are too heavily leveraged. They’ve been living beyond their means and have little or no savings, huge car payments, big rent payments and hefty credit card balances. This is a recipe for disaster. My advice? Streamline your expenses. Live modestly. Stop pretending to be a rock star. Even the real rock stars are eventually forced to play concerts at county fairs in their golden years just to make ends meet.

Another factor not numbered here is your spouse’s state of mind. The decision to quit will probably be met with a lot of resistance. And after you quit, they’ll continually urge you get another full-time job. Especially the wives. The security of a full-time job is important to them. In this scenario, you have two choices: (1) prove that freelancing is viable for your household or (2) admit defeat and go find another full-time job.

During my freelance stints, I’ve had a number of full-time job offers, but my personal preference is to remain freelancing unless the greatest job in the world comes along. Even then, I wouldn’t take a full-time job unless I freelanced there first. My downtime is too precious. I have a ton of personal creative projects in development.


If you get laid off, don’t panic. You’ll be surprised how un-scary it is. And you’ll probably like it. I did and I still do. But it might take 2-3 months to hit your stride.

Recently, my good friend Stephen was sharing stories of his successful transition from agency employee to president of his own company. He quit his job and started a small agency in Boston, where he now has a handful of clients, an office space and employees. I asked him if it was scary making the move. He said, “Yes it was.” However, he quickly found out that there was nothing to fear. Things worked out fine.

Then he shared a great story. Once, a few years back, his young daughter was climbing a tree on a sunny afternoon. She was playing on the branches, having a blast. But, at some point, she lost her footing and found herself dangling from a branch, holding on for dear life. As her grip began to slip, she cried out, “Daddy! Help!” From a few feet away, he couldn’t help but laugh because she didn’t realize that her feet were only 3 or 4 inches from the ground. He told her to simply drop. After some convincing, she finally looked down and was relieved to see her toes practically touching the grass. She dropped safely on the ground. “This,” he said, “was just like me when I was afraid to take the leap.”

What an awesome illustration. The point is, you will make a soft landing if you decide to quit and freelance. As long as you resist the fear, stay positive and be tenacious.


Here I’ve listed some pros and cons of freelance versus full-time. Perhaps it will help you in your decision.

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