DEV Community

Cover image for How I Quit My Job and Started Freelancing Full Time
Jonathan Sexton
Jonathan Sexton

Posted on • Originally published at jonathansexton.me

How I Quit My Job and Started Freelancing Full Time

A lot of us have some variation of the dream where we quit our 9 to 5 grind and work for ourselves while we rake in the cash. As of 2020, 36% of the total US work force (59 million people) were freelancers and that percentage is growing faster relative to other forms of work.

But how do you get there?

The answer is: There are hundreds, if not thousands, of ways.

There isn't an exact formula unfortunately as the journey can be an uncertain one. I'm going to share the way I did it. It may work for you or you may need to adapt certain aspects to fit your particular situation.

Some of you may be looking to go straight from learning/graduating into freelancing and that's definitely a viable option, it's just not the route I took.

I had a full time job before starting to freelance, so my advice will be centered around that path.

Also, I'm assuming you understand the legalities of freelancing in the US (i.e. You've already taken care of the appropriate local, state, and federal paperwork, setting up a bank account, paying taxes, etc).

Brief History of Working Background

I have been working in the tech industry for going on three years now but before that I was in sales and customer service industry for roughly twelve years.

I won't go too deep into details but if you want a deeper dive into my history, I've written several relevant articles: Conquering Interview Code Challenges v1, Conquering Interview Code Challenges v2, and How I landed My First Job in the Tech Industry.

Shortly after getting hired as a full time developer, I started freelancing on the side to bring in extra income for bills and to squirrel away for a financial rainy day.

Now that you're up to speed, let's get into the good stuff: how did I go from freelancing as a side hustle to freelancing as a main job?

Sacrifices Must Be Made

the daily schedule of jonathan sexton showing times throughout the day for different activities
Here's a look at my daily schedule while I was making my way into full time freelancing

Since I had a full time job, I needed to make time in my schedule before and after my 9 to 5 to accommodate my freelance work.

I started scheduling everything about my day from the time I woke up, to down time I spent with my family, to the time I went to bed, etc. This will required me to take a good look at where I could cut out time wasting activities.

Some of the things I sacrificed:

  • Spending time with friends on the weekend
  • Social events
  • Watching TV, playing video games or scrolling through social media in free time
  • Spending on vacation trips
  • Spending on adventures and experiences
  • Dining out regularly
  • Staying up late at night
  • Spending my lunch break watching funny videos

This list could go on and on but the point is I had to revamp my schedule to make time for what I wanted. I cut out things in my schedule that weren't productive or helpful.

One caveat, prioritize getting at least 7-8 hours of sleep, eating as healthy as possible, and family time. Some things are just too important to be cut out.

Have a Support System

There's no way I would have been able to go full time freelance without my wife - plain and simple. She has been my support system through all of this transition. I know it's been difficult for her as well but by being open and hones with each other we've made this a much smoother transition.

She was able to carry health insurance for our family during the first part of this transition.

If you live in the US, you know that everything related to finding fairly priced, reliable, and sufficient coverage without an employer subsidizing a portion of the cost is nigh impossible.

Without my wife bearing this burden, I would have no choice but to stay at my 9 to 5.

Freelancing income can be "peaks and valleys". One month you finish a project, get paid, and you're riding high. The next month you could have no work and you're in conserve mode again.

My wife helped stabilize our monthly income so that it's more predictable while I make this transition.

So what's the point of all this? Am I telling you to go out and get married so that person can help you move into full time freelancing? No, of course not. But having someone you can rely on while making this transition will make the process infinitely less stressful.

That person can be your friends, relatives, or even a mentor.

Save Money Relentlessly

This heading speaks for itself. No matter how you get paid at your current position, save whatever you can for as long as you can before making the transition. The more you save now, the better off you'll be when you decide to make the leap.

Everything you put back now will help you down the road during those "peaks and valleys" I mentioned earlier. This nest egg you create will offset costs you run into once you've quit your full time job.

One way my wife and I save money is to make meal plans (my wife does all the planning, I chip in with ideas) before we go grocery shopping for the week. Doing this allows us to see the ingredients we need for a week's worth of meals and keeps us focused while shopping.

If you're like me and have trouble making and sticking to a budget, these apps can help:

Have at Least One Long Term Client

This is the 2nd most important aspect, behind relying on my wife, that allowed me to transition to freelance full time. Having at least one long term client/project is game changing. This stream of predictable income has helped alleviate an untold amount of stress.

How do you find a client like this? The major job boards are a great way to start. There is no shortage of clients and companies looking for a reliable, albeit temporary, extra set of hands so to speak.

Typically, these companies aren't looking for full time employees - they just need help on a contractual basis. This is the perfect arrangement!

I've also had this type of relationship turn into plenty more work from the same client. I already had a contract with the company for one project, they approached me and asked if I'd be interested in working on a second project as well. I now have two, long term (more than 6 months) projects that provide predictable income.

A word of caution though, don't let this be your only source of income. Always be looking for more work/clients/opportunities.


Only you can determine what the right choices are for your particular situation. I hope this guide helps with your move into freelancing. If you have any questions, I'm always willing to help. Leave a comment or shoot me a DM on social media.

When you've made the leap, I'd love if you'd share your store with me!

Since you've made it this far, why not sign up for my Newsletter? You can do that at the top right of my blog. I promise I’ll never spam your inbox and your information stays with me. I like to occasionally send out interesting resources I find, interesting tweets I see, articles about web development, a list of my newest posts, etc.

If you haven’t yet, you can also connect with me on social media! I love connecting with others and meeting new people so don’t afraid to say hi.

Lastly, I'm available for hire! You can contact me through social media or by using the form the form on my website to get in touch :)

Have an awesome day my friend and happy coding!

Discussion (0)