Have you been day-dreaming about quitting your full-time job and making the leap to freelance? It’s a huge temptation for many of us and could be the right move.

However, you first need to consider some crucial factors before doubling down on your side-hustle. One of the greatest curiosities we have as consultants and aspiring independents is the big existential question: “when do I start freelancing full-time?” It’s a timely concern — a recent study by Upwork and Freelancers Union found that nearly 54 million Americans as of 2015 call themselves freelancers and 50 percent of that total has no interest in ever returning to the 9-5 grind.

Related reading: Ultimate Guide to Gig Economy Data: A Summary of Every Freelance Study We Can Find

The benefits of having your own self-employed business are manifold, but a successful “plunge into the deep end” means a lot of planning and self-discipline. If your current status checks out with all or most of the points below, it might be time to get swimming.

You have a “rainy day” fund

The conventional wisdom here is that a freelancer, to make a full-blown go of it, needs between three and six months of savings to cover basic living expenses (rent, groceries, health insurance, gas, etc.). You need to price out a realistic estimation of your month-to-month cost of living with some healthy wiggle room and determine if you have the funds necessary to weather a dreary dry spell or unexpected expenses. This is not money you should plan to cut into immediately. Ideally, you want your freelance work to do that heavy lifting! This strictly a tie-over.

Full-time blogger and business writer Gina Horkey is more conservative in her estimate to accommodate for the sometimes cruel whims of life as an independent contractor. “As a freelancer, 6-12 months is more like it,” says Horkey. “Again, this is due to the unpredictability of pay and planning for the unexpected — i.e. what if a client is late in paying you?”

You have a strong portfolio of work

This should come as no surprise — to start freelancing full-time you need a healthy body of work either from your full-time job or side hustle that conveys your unique capabilities to potential clients and this work needs to be accessible.

Take some time to refresh and clean up your social media profiles (particularly LinkedIn and any gig sites like Upwork). If you don’t have much experience in the field you aspire to work in, it’s better to gradually establish yourself on the side and work up to that self-employed dream, rather than to dive in with no skills or pipeline to get you started.

You have a network to draw from and work lined up

This item goes hand-in-hand with the last point — before leaving the agency I worked at a couple years ago, I made it a top priority to line up at least a couple clients and a number of professional contacts prior to my exit.

Some of these contacts didn’t amount to anything — others I still work with to this day. In one case a competitor even got me a gig (the client was in the same industry as one of his pre-existing clients and posed an ethical dilemma)! Do some legwork before you bail; you will be very glad you did.

You’ve experimented with a daily routine (and you were actually productive)

When freelancing full-time you need to hold yourself accountable for all of your working hours. You may have no problem doing this for your boss or project manager, but when your day is a blank canvas and no one is hovering over you, how do you fare?

If you don’t have a good sense of this, try blocking out a strict night or weekend part time schedule for yourself. Commit to working ‘x’ hours every Monday and Wednesday night or maybe Saturday and Sunday morning. Assess whether or not you are capable of being your own boss.

When you get work, you need to be able to crush it.

You have reached your “tipping point”

No, this does not mean you’re going to snap if your boss makes another hypercritical remark to you or that you’ve simply reached the end of your rope — what we’re talking about here is the “tipping point” where continuing your day job is actively cutting into good opportunities to expand business within your freelance ventures.

For instance, a career-advancing project comes up on the side for you and your current full-time job does not afford you the time necessary to do it — perhaps multiple clients want to expand your role with them — maybe you even had to turn down new clients because of your 9-5!

For many reasons, this is not always a requirement but it is definitely a good indicator.

Look before you leap into freelancing full-time. Then leap!

If you’re anything like me, you never truly feel ready. There’s an upside to this insecurity in the sense that you’re always driven to grow and prove yourself. However, fear should not hold you back from making an honest and well thought out venture into freelancing full-time, especially if you have the aforementioned points in order.

As our colleague Jessie Kwak puts it, “The first goal is one client. Change that and change everything.” If you wait until you’re ready, you’ll never do it.


Ben Shanbrom is a freelance writer, musician and copy editor who works with artists and clients within his native New Haven and beyond.