How to Take the Freelance Leap


The way we work is changing. Where once we expected a long career with a single company, the modern workforce is becoming increasingly nimble, distributed, and interested in impact over stability. In many industries, thanks to digital technology, seamless communication, and the decline of gatekeepers, corporate hierarchy is out and horizontal loyalty is in. With all of this, of course, comes the rise of the freelancer.

While many people are attracted to the freedom and autonomy of freelancing, contemplating a big shift to the way you work is difficult when stability and a regular paycheck have been the norm. Not everyone is suited for the peaks and valleys of a freelance lifestyle, so it can be hard to know if this kind of upheaval is right for you.

If you’re considering the leap, here’s a look at some ways to make that transition easier, how to really know that you’re ready to make your living as a full time freelancer, and what structures you should have in place before you do.

Know what makes a good freelancer

Are you already doing something valuable for free, as a favor, or in your free time: Giving advice? Making jewelry? Baking cakes? Editing reports? Taking photos? Is the way you spend your time as important to you as the amount of money you earn? Do you like switching up your routine on the regular and dislike being told what to do? Do you think about your to-do list for next week while you’re still getting through this week’s? Are you passionate about something? Is the idea of working while you travel appealing? While answering “yes” to every single one of these is not essential, the more of these you feel describe you, the more likely it is that you are well-suited for the freelance game.

Decide what kind of worker you want to be

Entrepreneurs make money while they sleep. They can walk away from their business for a month without it falling apart and then walk back in the door and disrupt what’s not working. Freelancers put their hands on all of their work, and at the end of the day, they can point to something and say “I made this.” Side hustlers build or make something on the side, while having another job that pays some or all of the bills. It may turn into one of the above, or it may just stay a side project. Knowing the difference between these three models—and deciding which one will work best for you—is key.

Recognize the importance of an anchor client

Whether your hustle is marketing, writing, coaching, or something entirely unique, it really helps to have an “anchor” gig or client when you first start out. This means a relatively stable or certain gig that comprises a set chunk of your income every month, which you don’t have to devote time to securing in the month prior. While this doesn’t have to be the most awe-inspiring work you do—it could be, say, writing newsletters for a corporate client or managing a corporate social media account—it helps cut down on the stress of looking for all your work, every month. The more you freelance, the more confident you’ll be that work will come your way via your network, referrals and contacts. But in the early stages an anchor client can help you stake out your hustle with a semblance of stability.

Have a cashflow plan

Ask any freelancer—the biggest struggle of the freelance game is not not having money, but not having money when you need it. Good freelancers are prepared for this and always have a plan when it comes to these cashflow crisis moments. Whether that means a comfortable savings account, credit cards that you don’t abuse and pay back as soon as you get paid, or a partner whose income can tide you over until money’s in the bank, you must have a plan in place for when checks don’t arrive when they should. Because—spoiler alert—sometimes they wont.

Redefine work life balance

When you freelance, work life balance comes in waves, not on a day to day basis. Some weeks you’ll be in the weeds and working through the weekend, while others you’ll be able to say yes to a random travel opportunity and not have to tell anyone but your cat-sitter. It’s a misconception that freelancers have to work “all the time” to make it. Some weeks, that will be the case, but most weeks you’ll have the satisfaction of creating a schedule that suits your lifestyle and preferences.

Embrace that branding yourself is now your job

Make no mistake, if you’ve entered the freelance game, social media and online branding is now a big part of your job. When it comes to your online presence, never make someone work to figure out what you do and how to contact you. You need to think about a searcher’s journey when they’re vetting you online and never assume they’ll start on your website. If they land on your Twitter or LinkedIn or Instagram as their first impression, are you putting relevant professional info there as well as the means to contact you and/or find out more about you? Are your bios consistent across all your platforms? Are you showing that you’re active and engaged in your community or industry rather than just promoting your own work? Also remember to focus your efforts on networks that are not “double opt in” (that means relying on Facebook and/or making your Twitter or Instagram private is a bad idea). People often prefer to vet anonymously and without you knowing, so give them what they want.

Don’t go it alone

As a freelancer you are not only your own marketing department, but also your own HR and accounting department, too. It’s best not to try and manage these things all on your own. There are lots of resources out there to help you navigate things like healthcare and your tax status (check out The Freelancers Union in the US and the Federation of Small Business in the UK, for starters). Most importantly, grow a network of other freelancers so you can do things like ask around to find a great freelance accountant (and please dear god, hire an accountant) and what healthcare solutions have helped for other freelancers you know. Your network is not only a way to get work, it’s a way to feel like you’re not going at it alone.


Tune in to new episodes on the 1st & 15th of every month!

About Author

JosephineJane are boutique career and brand strategists and the creators of Career Cardio. We overhaul your employment profile online, on paper, and in person. Visit us at and @JJ_careercardio on Instagram & Twitter.