In terms of career paths, I pride myself on being a true millennial. I’ve worked as a full-timer, a part-timer, a freelancer, a consultant, and now a founder. It’s been a whirlwind, but I don’t regret a career move I’ve made yet.

I started my career teaching for three years and made the switch to freelancing when I realized how much I enjoyed working on several different projects at once. After lingering for a while on a blog about art, I decided to make the official jump to freelancing. It wasn’t an easy decision—in fact, I freelanced for only three months before I got nervous and took a full-time job. It took six months of working for this company to confirm that I function best in a non-traditional environment, working on multiple projects that utilize different parts of my ability. It wasn’t an easy path, but I’m glad I took all of these steps to get to where I am.

Lately, I’ve been getting more and more questions about making the transition from full-time office job to full-time freelancer. And the first thing I’d say is that freelancing isn’t right for everyone. There are obvious positives, but there are uncertainties to consider, it takes a lot of hustling, and your parents will consistently ask you if you’ve “gotten a job yet.”

The second? If you think you’re ready to take the leap, there are three steps you should take now—before leaving your job. Here’s how to get started on your own freelance life.


1. Test it Out

This is perhaps the most crucial step to take when considering any career change, but it’s even more important with freelancing. Try taking on side projects (paid or unpaid) in order to get your feet wet—it will mimic the networking necessary to actually get paid gigs, the tumult of working on multiple projects at once, and the trials of working in non-traditional settings like your home or a coffee shop.

A large part of testing out a new career is also asking yourself the tough questions. Here are a few to consider about freelancing:

  • How will I get health insurance?
  • Where will I work each day? Am I self-motivated?
  • Can I create thorough to-do lists and set my own deadlines?
  • Am I comfortable working with many different types of people?
  • Am I comfortable networking and hustling to get jobs?
  • How much do I want to get paid per hour?
  • How many hours a week do I need to work to make enough money?

It can be really helpful at this stage to talk to people in your field who have made the leap to get their suggestions and advice. Once you’ve tested the waters and worked through some of those questions, it’s time to move on to step 2.


2. Define Your Skills

When you’re a freelance writer, you usually have a list of topics that you’ve covered and are comfortable covering. It works the same way with all freelancers: You need to define your business so potential employers know exactly what they’re hiring you for. The list can be as long as you want, but the more defined it is, the easier it is for someone to hire you.

For example, if “social media management” is one of your skills, break it down. Include which social entities you’re familiar with, which analytics you use for tracking, what type of content you specialize in, and any other details that will specify what you can actually offer. Before going full-time, I decided to build skills in key areas including instruction design, community building, and technology in the classroom, in order to specify my offerings for potential projects. This not only pushed me to narrow and define my interests, it also helped me choose projects where I would be most useful and productive.

This is something that I notice many freelancers don’t do, but I strongly encourage working through defining your skill set. It’s a great way to assess your strengths, figure out what your weaknesses are in order to improve upon them, and consistently deliver on your promises.


3. Build Your Business

So, at this point you’ve tested out the whole freelancing thing, you’ve defined your offerings, and now you’re ready to go. But there’s one more step to take before heading out the door.

Before leaving your job, you’ll do yourself a huge favor if you set yourself up for immediate success. Spend your nights and weekends working on your new business, reaching out to your network, and browsing potential opportunities. Build a website featuring all of the projects you’ve worked on, the skills that someone can hire you for, any other relevant information (articles you’ve written, your bio and resume, whatever makes sense for you), and your contact information. (This can take a while, so I suggest you get started early.)

When your site is ready to go, start asking your network if their companies or contacts are looking for freelancers. Another great way to find jobs is to find a company you like, set up an informational interview, and pinpoint an issue you’d be willing to come in and solve. It’s not necessary to wait until you have your first paying freelance job before you leave your current full-time job, but it does help ease the transition.



A final piece of advice I always tell those who are still hesitant: Remember that you can always change your situation. If you try out freelancing and realize it’s not for you, there’s always the option to find another job.

But, if it is for you? Well, take it from me: You’ll enjoy extra freedom, exciting projects, meeting new people, and the complete satisfaction of working in your PJs.


Photo of freelancer courtesy of Shutterstock.