Employee to Contractor: 10 Tips for Making the Switch

By Kristen Harris

Is one of your New Year’s resolutions to (finally) go out on your own as a freelancer or contractor? Have you been building a side hustle that’s getting big enough to become your main hustle? Maybe there’s “something in the air” at your current company, and it feels wise to explore your options.

If 2020 is your year to make a move, here are ten tips for making the switch from working as a full-time employee within a company to working independently on your own.

  1. Treat it like a job. Get up, get ready, and go to work, even if “work” is your dining room table. When we first started Portfolio Creative, my wise business partner told me, “get up every day, take a shower, and put on real pants.” Plan your work schedule (the days and hours you’ll be working) then commit to it just like you’d commit to any employer. Be at your workspace on-time and ready to go. 

  2. Treat yourself like a brand. You are no longer just a talented individual. You are a business and a brand. Everywhere you go, and everything you do represents your brand. When introducing yourself, lead with the service your company provides, not what you do. Say, “I own a branding firm that helps health practitioners grow their practice” not “I’m a graphic designer.” Be sure anything you put out into the world, IRL or online, is representative of the brand you want to build.

  3. Treat it like a business. Often when people start working independently, they think they’ll spend all day doing the thing they are great at and love. The good news is, you’ll get to do a lot of that and work on projects you enjoy (mostly). The bad news is that there’s more to running a business than executing the work. A classic book on this topic is E-myth by Michael Gerber; he provides some free online resources as well. The point of the book is that you need to set up systems to function as a business, not just as an individual doing work. Find efficient ways to track hours and expenses, invoice clients and collect payments, market your services, and anything else necessary to maintaining an inflow of work and income. 

  4. Treat yourself like an employee. Have the same expectations of yourself that you would have of anyone who might work for you. Do great work, give it your best effort, meet timelines, show up for meetings, listen to understand client needs, and accept feedback graciously. In return, give yourself what an employer would provide to their employee. You deserve frequent feedback, constructive criticism, fair pay, opportunities to develop skills, and the resources you need to do great work. This can feel a little awkward like you’re having a review meeting with yourself, but taking time to reflect on what you’re doing well and how you can improve is valuable.

  5. Have a financial plan. Figure out how much money you need to make and expenses, then price your services accordingly. Estimate how long of a runway you have with savings or other family income, then double that timeframe because nothing happens as fast as you think it will. Make sure anyone who financially relies on you is on-board (spouse, kids, roommate, family); the decisions you are making can impact them. Plan for how you’ll cover any income gaps as well as provide for healthcare, retirement, or other benefits that came with your full-time job. Have a back-up plan and a back-up to the back-up. For example, can you work part-time until your business ramps up? Take a side job just for the benefits? Will your spouse continue or start working? 

  6. Plan for taxes. Taxes are financial but deserve a section of their own. Most people don’t save enough for taxes, especially in the first year or two. Either they underestimate how much will be needed or, even worse, think it’s the same as when they were a full-time employee. It’s not! Employers pay a portion of your income taxes, and now you have to pay that portion too (congratulations, you’re both the employer and employee). Every time you receive payment for your work, immediately divert a set percentage to a separate savings account just for taxes. Consult a tax professional for your situation; we like to save 40-50% to have a safety cushion. Having too much never hurts, but too little is painful.

  7. Plan for being “out of the office”. When you are working independently, no one is providing sick, vacation, or PTO time. Still, there will be days when you can’t or don’t want to work. When planning your prices and projected income, take into account a certain number of days that you won’t work due to illness, vacation, funerals, and life. Have relationships with a few trusted professionals that could cover your work or where you can refer clients. Which leads us to…

  8. Build partnerships and alliances. Even if you’re working on your own, you are not an island. It’s essential to build relationships with others, looking for skill sets similar and complementary to your own. Yes, this is networking, and it doesn’t have to be painful. Look for people you enjoy and work well with to partner on projects, share resources, and refer opportunities. People with skills similar to your own can provide back-up for vacation or illness; complementary skills can help you take a team approach with a larger project. 

  9. Find your co-workers. There’s a reason that co-working spaces are popping up like mushrooms, and half the people at my local coffee shop are working on laptops and taking calls. While working for yourself, by yourself, can sound like a dream come true, it really can be lonely. People tend to underestimate how much they gain from conversations with co-workers, whether it’s casual chitchat by the coffeemaker or in-depth creative brainstorming sessions. Find places to have human interaction and creative conversation every so often. 

  10. Be open to opportunities. Have a plan. Be open to throwing that plan out the window. Often an opportunity, a big client, or growth of a side hustle seems stable enough to decide to start working independently. This is great! Put together a plan, know what you’re offering, your target audience, and how long it will take to make enough income to be sustainable. But also be open to opportunities that come your way. That unexpected client, project, or job offer could be the catalyst to the next stage in your business or career. 

If 2020 is your year, congratulations! Going out on your own can be exciting, scary, and everything in-between. We love supporting creatives in their independent ventures; if you’d like to chat about opportunities that could help you take the leap, we’re here to help.