How to Face Your Fears and Embrace Freelance Life

You’re on your own but you’re not alone as an independent contractor.

You’re on your own but you’re not alone as an independent contractor.

Starting out as an independent contractor is exhilarating but it can also be terrifying. In this Q&A, we catch up with freelance writer Chelsea Schuyler, who is bringing her course Setting Up as an Independent Contractor to PUGS in March.

Q: Why is it important to plan your first steps in freelancing?

A: Ever procrastinated a task by doing some other task? Like instead of cleaning the house you spend hours organizing your shoebox photos? The initial excitement and energy you have to become a freelancer are precious; you don’t want to burn out on menial tasks that don’t end up getting you anywhere! When I first started, I ended up spending six hours making the perfect business cards. Two weeks later, I had 500 business cards with no one to give them to, no other actions accomplished, and no idea what to do next. (After some research, I later realized I had to redo the cards anyway.) It’s tempting to want to go out and do something productive that will validate your ideas, but too often these efforts add up to only money spent and motivation gone. I’ve known folks to rush out and pay for their business registration, and then never do anything with it, or pay for a website yet never make it live.

In this class, I hope to offer the tools to focus that initial excitement to make a plan that manages your time and activities in small, doable increments. Getting things in the right order can also save you so much time and money in the end. Don’t buy a domain name before knowing what web host you’ll use. Start a journal to track your miles instead of trying to go back and remember your travels two days before taxes are due. Planning is a time saver that can make all the difference!

Q: What are three things you wish you knew before you went independent?


A: How to organize myself so that taxes wouldn’t be a nightmare. What computer programs to use that would actually be affordable and helpful so I didn’t have to spend hours researching the best ones or finding out in the fine print later that they wouldn’t work for me. I wish I had been given templates for budgeting, work proposals, and work term contracts. So much agonizing over wording, legalities, and other boring details are done for me? Yes, please!

Q. How did you get past your fears and stuck points to finally go independent full time?

A: There are so many thoughts and emotions that go into starting out on your own. We tend to think we should push down our fears and just go for it, but fears that go unacknowledged can turn into procrastination, dread, or other buzzkills to your productivity and success. Spending some real time getting my passions and fears down on paper helped me process and ready myself for the journey of freelancing. Knowing my passions helped me narrow my business focus to what I really enjoyed and valued. Nailing down my fears to paper allowed me to work out real strategies of dealing with them. Some of those fears were more nebulous, but even just having them identified with words helped me move past them, or at least accept their presence in a way that wouldn’t allow them to take over.

Q: What should contractors be doing to prepare themselves and their businesses for the future?

A: Before you take any action, allow yourself a learning phase. Set aside dedicated time to research on the internet or at a bookstore. Start conversations with friends and family, even strangers you only have a thin connection to. When someone asks you “So, what do you do?” skip to the part where you say “I’m looking into being a freelance ____.” You’d be amazed at the generosity of people that will come right out of the woodwork. If you hear that someone does what you want to do, offer to buy them a coffee if you can pick their brain, and take notes. Get a mentor, attend networking events. Use simple tools to hold yourself accountable and stay on track! Revel in the satisfaction of your own productivity and turn your initial energy into a machine that makes more energy driven by small successes.

Join Chelsea for Setting Up as an Independent Contractor from March 3.