9 Steps to Going Freelance

Reinventing the wheel and trying to cobble together a freelance career is largely a waste of time. It can work, but will take longer than tapping into your existing framework of contacts. Starting with the company that’s already willing to pay you is a smart idea, but needs finessing to execute successfully. Here are some tips to help guide you through the process.

Before Going Freelance



Most freelancers I know (myself included) mentally and physically check out of their last staff jobs, disgruntled by the unfair disadvantaged of doing crap work and not being able to live out your dream of freelancing on the beach. But the first (and most crucial) step in asking your boss to keep you on as a freelancer is to do amazing, irrefutable, and incredible work.
Start by showing up motivated, digging into your projects and going above and beyond anyone’s wildest expectations. Come up with new ideas that could benefit the office whether it’s a new filling system, streamlining your sales autoresponder email, revolutionizing your product copy, or figure out how changing vendors could save the company big bucks.
But the point isn’t to become irreplaceable in your current job, otherwise your boss will just find excuses and small incentives to keep you doing exactly what you’re doing – or train someone else to do it just like you.
The point is to be so amazing at everything you do that they can’t afford to keep you in your current position. They’ll either want to promote you or give you new, exciting responsibilities to tackle. This can lead to invaluable new skills for your resume, and also put your employer in a position where they couldn’t possibly say no to hiring you as a consultant or freelancer.


It’s not your boss’ job to figure out how they can use you as a freelancer. Sure, they may have a good idea of how and where to use you, but chances are they’ll expect you to come up with the game plan.
Figure out which skills at your job could be outsourced and benefit the company at the same time. It’s not enough to just be really great at your job. Your company needs an incentive to outsource work, whether it’s because you’ll save the company time and money, or because you know the system so well it’s not worth their time to hire and train someone new.
It’s normal to list all the sexy responsibilities you want for freelance work like taking clients for a sales lunch and writing the company blog. But don’t overlook small, mundane jobs. Need some ideas on skills you could offer as a freelancer to get started? Thy these:

  •  Project management
  •  IT work
  • Bookkeeping
  • Creating client pitches
  •  Research

Once you’ve identified what skills you could offer as a freelancer, position yourself to be seen in those specific roles at work. If you want to be a project management freelancer, develop a streamlined system that helps everyone stay organized and makes their work load, and lives, easier.


My clients usually praise my flexibility and ability to just go with the flow and get things done autonomously. They’re not necessarily looking for the best writer, video editor or creative mind. Instead, they want the project to:

  1.  Get done well.
  2.  Get done without a ton of nitpicking questions and panic attacks.
  3.  Go pleasantly. No one likes working with a control freak.

Don’t mistake being flexible with being a pushover. It’s okay to stand-up for yourself and come up with better solutions than being made the grunt. But being flexible also means shedding your ego.


Many employees cower around their boss, dashing off to the break room to avoid face time. But even having passive face time with your boss like saying hello, showing up early and staying late or asking for a quite 5-minute meeting to discuss a project is crucial.
According to an article by MIT Sloan Management Review, “There seems to be a norm that anyone hoping to move up in the management ranks needs to be here late at night and on the weekends. If you’re not willing to do that, you’re not going be seen as dedicated enough to get promoted.”
Remember asking to go freelance or become a consultant is essentially a promotion. You’re asking them to see you in a new role and as a dedicated, capable person. You can’t do that if you can’t look your boss in the eyes or build-up the momentum to developing a lasting relationship with.


Diving into the freelance waters without any type of self-promotional tools in your arsenal will only leave you floundering in cold water. Now is the time to start thinking about how to promote yourself, collect testimonials and set-up your social media channels to showcase your skills.

  • Collect testimonials from your previous employers about your work ethic and add it to LinkedIn or your online portfolio.
  • Set-up your LinkedIn profile, connect with everyone you know, and complete the resume section.
  • Seek out press from HARO (help a reporter out). You can volunteer to be a source for journalists looking for a sound byte. Your position as an IT expert could pop up in news around the world and can be added to your online portfolio as “expert source for XYZ industry.”



There’s a chance your boss will either say “no” to you freelancing due to budget constraints or other issues, or tell you it will take a few months to sort out. This is okay. Freelancers should never have all their work in one pot risk losing it all. Curate a list of your company’s competitors handy that don’t present a conflict of interest. Your boss may tell you they’ll use you as a freelancer, but only if you sign a non-disclosure or decline work from competitors for a specific period of time.
To branch outside the box, think about B2B (business to business) companies. If you work for an architecture company servicing private clients, think about companies that act as vendors for architects. Examples might be architecture software, suppliers or conference planners.


What’s your competition up to? When I was exhausted by trying to seek out new freelance writing and name consulting clients, I started googling my competition. “Atlanta freelance writers” “Naming consultant” “Writing for custom content publications” and any other phrases I could think of. Suddenly I had insights to what type of work and clients were within my reach.
Seeing what your competition is up to can tell you if you’re lagging behind their skillset, but also tell you what clients hire freelancers. Look through their client roster and see which ones might be a good match for your skills. And if you feel your experience isn’t up to your competition’s level, figure out how to land some pro bono clients or help out a friend’s company to gain the experience you need.


It’s time to get your feet wet as a freelancer. Seek out freelance work from friends, family or from Upwork (formerly Odesk) to get some experience under your belt. Getting your first gig will help instill confidence, and also help you see where kinks might lie before working with your company as a freelancer. For example, learning how to manage client expectations, troubleshooting issues and meeting deadlines are all things that can’t be learned until you’re in the thick of it.
If your boss says “no” to your freelance offer, it’s also essential to already have a client or two waiting in the wings. Even if they’re small clients who won’t pay the bills forever, those first clients can offer testimonials, word-of-mouth referrals and future work.


The time has come. Ask your boss for a quick meeting and open with saying how much you love working at the company. Get to the point and let them know you’re interested in becoming a freelancer or consultant and how your services can impact the company for the better. Offer up a bullet point list of how it could work, why it’s in their best interest, and ask for feedback on your ideas.
Regardless of the outcome, the key is never to burn bridges. You never know when they might come calling weeks, or even a year later. They also may not have work for you, but be so impressed by your overall performance that they pass on your name to other colleagues.
Chances are high your company will offer some type of work whether it’s contract based or the type of freelance you’re looking for. But if they don’t, you’ve successfully positioned yourself to go out and snag work with their competition. You are on your way!

Susan Finch

Freelance Writer at Freelance Parenthood
Susan Finch is a freelance writer and creative Jill of all Trades working with major brands, publishers and entrepreneurs. She blogs about breaking into the freelance world to live a flexible and rewarding lifestyle at FreelanceParenthood.com.




  1. Jenny Powers

    This was just what I was looking for! Thank you. I’d love to learn about breaking into freelance writing for magazines and blogs.

    • Megan Barnes

      Hi Jenny 🙂 So glad to hear that Susan’s article is timely for you! Best of luck in researching — drop us a line when you go for it and we’ll toast to your success!

    • Susan

      Hi Jenny,

      Great! So glad to hear it was inspiring. Feel free to get in touch anytime through my blog at FreelanceParenthood.com. I’m happy to lend an ear or give you some ideas.

  2. michelle

    great article. I am already a freelancer so the part relating to asking my current boss to make me a freelancer doesn’t apply, but some really great tips here!

    • Megan Barnes

      Thanks for sharing, Michelle! Hope Susan’s advice propels your freelance career forward. Check out her website for more resources — she is a treasure trove of experience.

    • Susan

      Got any good freelance tips? I’m always looking!

  3. Morgan

    I left my job a couple of years ago to stay home with my kids but have been able to continue doing freelance work for my former employer in spurts. I’m looking to expanding my freelance jobs from small clients with small hours per month to article submissions for my writing pieces. Such a different beast!

    • Megan Barnes

      Congratulations, Morgan! 🙂 You’ve been selected in our drawing to win free admission to Susan’s course “Break Into Freelance Writing Without Experience”…best of luck in your pursuit of expanded freelance work! You’ll receive an email shortly about retrieving your prize. Thanks for sharing!

    • Susan

      Sounds like you’re off to a great start! You can leverage those projects and past experience to find like-minded employers looking for contractors. It’s tricky figuring out the freelance game, but well worth it in my opinion. You really have to look at the big picture and take the long view.

  4. Meagan

    Loved this article! And it’s total serendipity, because I was *just* looking for a course about breaking into freelance – so thank you! I’ve had the writing bug since I was a little girl and I can’t ignore it any longer…time to jump in! 🙂

    • Megan Barnes

      Glad to hear you’re going for it, Meagan! Wishing you tremendous success with your writing. 😉 Thank you for sharing!

    • Susan

      Yay! Great to hear it. Get in touch if you have questions or want to talk about freelance. I’m always eager to hear others’ stories and help refine my courses and content on my blog.


Leave a Reply to Megan Barnes Cancel reply

Your email address will not be published. Required fields are marked *

Pin It on Pinterest