To the Aspiring Contractor, Expert Freelancing Tips from Our Team

Cheriann Cain
Posted: May 16, 2019

So, you are thinking of freelancing – the allure of being your own boss, choosing the projects you want to take, and having the flexibility to work from home is quite attractive. However, it’s not for everyone. Make sure you take an honest inventory of the way you naturally function. Do you like change? Are you okay with the ebbs and flows of contract work? If your answer is “heck yeah!,” then you will love these freelancing tips and bits of advice from our expert consultants with a combined 50+ years of experience contracting!

“Each and every project is different, with different clients, different requirements and different styles. You must be nimble and shift gears quickly and easily from one project to the next.” – Valerie Groce

1. Give yourself some space!

Here’s my tip: Working at the kitchen table may suffice for a short time, but if you’re serious about freelancing, you will eventually want a dedicated office space somewhere in your house. This allows you to stay focused and minimize background noises (dogs always seem to want to chime in every time you are on a conference call). Having a separate space for business also allows you to “leave work.” We know it’s all too tempting to run back to the computer every time you hear a ding! And another added bonus – dedicated office space can be a tax write off!

If you just can’t stand staring at that basket of unfolded laundry, you might even consider renting some coworking space. There are many great options to choose from, like office evolutions.

2. It starts with a good plan

There are many employer benefits that you won’t have access to as a contractor, so you will want to do your homework. It’s a good idea to meet with a small business accountant or tax attorney and decide if you are going to incorporate (since many clients / contracting agencies require incorporation) so you can understand the tax implications. After all, Uncle Sam still wants his cut of your earnings! You can dive deeper into this topic here.

Plan for the distant and not-so-distant future. Do you have access to health insurance? Check into coverage options for self-employed contractors. Have you thought about retirement? Look into a SEP IRA to start saving for retirement. And what about slower times? Financial experts say you should have a minimum of three months’ worth of living expenses saved, but you should consider doubling that. Even the best freelancers will have some downtime between gigs.

“Setting up a ‘liquid’ savings account for those months that your work is lean is a good idea. In this world, it can be feast or famine.” – Cynthia Brendza

3. Work hard, play hard

Our freelance experts had a lot to say about this topic! Contracting gives you the flexibility and freedom to plan your own schedule. Do yourself (and your clients) a favor by scheduling your available time and communicating that to your clients. You won’t always be able to make your favorite yoga class, but blocking it off on your calendar gives you a better shot at it! On the flip side of that coin, there will be days that you are glued to your computer for hours and eventually realize that all you have eaten is a stale cracker you found on your desk. Getting up and taking a brisk walk around the neighborhood will really re-energize you.

“Set a timer to switch from work time to personal time.” – Julee Travis

Make sure your family or other housemates understand the boundaries of your workday and try to keep to that schedule as best as possible. Children are more apt to leave you alone during work hours if they know you have specific time blocked for them. You can even enforce official business time with some helpful signage. Check out these great “Do Not Disturb” signs from our very own Kesha Dougan!

Download the signs

“Be prepared to keep the kids busy during snow days and summer break.” – Kristine Burrichter

Here are 9 ideas to keep those kiddos occupied.

4. Pick me, pick me

As a freelancer, you are your own marketing department. Click To Tweet

Connect regularly with your contracting agency, making sure they are aware of your most current availability. Don’t ever assume they know when projects have been delayed or cancelled, resulting in your availability opening up.

“Keep in touch with your clients and let them know you appreciate the work.” – Jane Graves

Also, keep your online profile up to dateand stay connected with others in your industry. Most importantly, stay in tune with the latest industry trends. Free webinars are bountiful!

“Join local associations (like ATD) to network with others and build relationships that support your business.”  – Teresa Chiapputo

With these tips, you will set yourself up for contracting success. Happy freelancing!


Are you a learning professional interested in a collaborative virtual environment that offers flexible hours, competitive pay, mentorship, and access to professional development?

Learn more about the perks of contracting with ttcInnovations and view our open positions!


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