12 Signs You’re Ready to Go Freelance



Escaping the 9-5 prison and voyaging into the Great Unknown can be a bit intimidating. Many people who want to freelance take years to make the leap (and that’s not necessarily a bad thing).

But how do you know you’re ready? Here are 12 serious and not-so-serious signs it’s time to make the leap.

1. You have a well-developed network.

I thought I’d get the obvious one out of the way. A well-developed network — whether it’s through your 9-5, social media, or your charming personality — is almost essential for a successful freelance career. Unless you’re an Erlang developer or another highly-prized catch.

2. You’re able to keep your own deadlines.

Deadlines your client gives you? They’re fine. The deadlines your give yourself — like doing some marketing for your business, setting up your website, organizing your files for tax season — are harder to keep. That’s a skill you should try to master first.

3. You understand that work won’t just fall on your plate.

This is more of a mindset shift than anything else. In the 9-5, work comes to you and you do it. You need to know that as a freelancer, marketing, finding work and setting up contracts may be ⅓ to ½ of your working hours, especially in the beginning before word-of-mouth builds. You need to be OK with this.

4. You love learning.

As a freelancer, you’re responsible for keeping your skills sharp. There’s not going to be a company training program, a paid seminar, or a built-in community of other smart, cutting-edge people. Cutting edge you must be.

5. You’re not afraid to stand up for yourself.

Because clients will surely stand up for themselves. Good freelancers know what they’re worth, and aren’t afraid to communicate that value.

6. You don’t like to take vacations.

You’ll be taking these eventually, but in the first nine-twelve months…probably not.

7. You have a safety net.

Save up for a bit before making the plunge. Starting your own business is stressful enough — you don’t want to be worried about paying rent the first few months. Give yourself a cushion.

8. Your family/friends are supportive.

Make sure your family/friends understand the potential impact of you going freelance. Like hogging the computer in the office. Or good stuff, like actually being home for dinner. A supportive spouse can be worth more to your business than an Angel investor.

9. You have a solid (online) portfolio of work.

And as one of my favorite freelancers Sean McCabe says, come up with a reasonable target number of portfolio items — and then double it.

10. Your boss is boring/annoying/mediocre/cramping your style.

Certainly not a prerequisite to freelancing — many happy freelancers were also happy employees — but having a bad boss can really highlight the basic problem of the 9-5: your work belongs to someone else. Hopefully when you become your own boss, you won’t end up thinking that you are annoying.

11. You’re hungry.

This is the most important of the list. You need to want it. Freelancing isn’t the option you take because you’re lazy or don’t want to wake up in the morning. You want to make a name for yourself, you want freedom, and you want it now.

12. You love your pajamas.

You may be spending a lot of time in them. I hope they’re cuddly.

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This post was originally published on Freelancersunion.org.

Disclaimer: General Assembly referred to their Bootcamps and Short Courses as “Immersive” and “Part-time” courses respectfully and you may see that reference in posts prior to 2023.