The Reality of Independent Contracting: Not All Cushions, Not All Pins

By Tom Bentley, Contributor, on December 7, 2016

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People considering or just stepping into freelancing have presumptions that can run the gamut from “I’ll have to work 19 hours a day!” to “I can lie in a meadow for two hours a day and wait for a visit from the muse.” Not quite.

While you might face some number of long days, and may occasionally be able to steal away for a meadow meditation, the reality of independent contracting is much more mixed. While the challenges can be considerable, there’s never been an easier time to move into freelancing: The wealth of freelancer information resources (from online to print to in-person) is vast.

Mind Matters

Before we discuss some of those resources, let’s look within: What are some of the internals that a person should have or develop to succeed in independent contracting? A few to chew on:

  1. Motivation: Independent contractors don’t have a boss to assign or supervise their work. They must be and stay motivated to understand their own skills (and skill needs), as well as if there’s a market for those skills. They must energetically enter that marketplace and continue to present their developing skills and successes to it—there is no, “Wow, glad I got that one contract. I can relax now.”
  2. Discipline: Independent contractors often have to juggle multiple projects with varying deadlines. Everyone has an occasional missed deadline, but few clients are happy with even one. The freelancer who tracks how long projects take, learns to build in timing flexibility and regularly hits his or her deadlines is a contractor who gets return business. Oh, and it almost goes without saying, but hours spent twiddling on Twitter or fencing on Facebook are … not exactly helpful.
  3. Cordial Communication: Nobody wants to work with a sourpuss or a robot. Even when you’re negotiating hard numbers, never forget that the person who will be paying you is, indeed, a person. Open, respectful and friendly communications never put a contractor in a compromising position.

The reality of independent contracting demands as many emotional skills as occupational ones, so get your mind in line.

Take a Stroll Through the Tool Yard

Depending on your field, you might have to make a substantial investment up front in the tools of your trade. I’ve been in the independent writing and editing biz for more than 20 years, and my equipment needs aren’t heavy. I’ve got a Mac laptop that’s several years old running Microsoft Office 2011, and a years-old desktop machine out in my old Airstream office (which itself is running 1966 on a continual loop).

Of course, I need a reliable internet connection and maybe a decent pen. But if you’re an independent house painter, you probably can’t use paint-caked, 5-year-old brushes. But perhaps for some of the expensive equipment, like your airless paint sprayer, you could buy used. Shockingly, some equipment can even be repaired. Ebay is often the freelancer’s friend; over the years I’ve bought and sold lots of computing equipment there.

Don’t forget: Whether you’re a painter or a painter of words, building a website that lays out how you’re going to solve your customers’ problems with verve and talent isn’t a nice-to-have these days; it’s a need-to-have.

That’s So Taxing

One surprising PBS piece notes how few people stepping into independent contracting know that they are supposed to pay quarterly taxes on their income. In a word: Yes. You’re your own payroll now (and, often, your own accountant, purchasing agent, source of noontime sandwiches and more).

Laws can differ on state taxes, but the IRS is happy to clarify any questions you have about quarterlies. It can be tricky for first-time freelancers to determine projected income the first year or two, but continue to slice, dice and measure. Put those quarterly dates in your calendar and remember that you can be penalized for being late.

Support for Soloists

The notions above only skitter on the surface of what independent contractors face. But there’s a remarkable amount of support out there for freelancers, no matter their trade, thanks to the U.S. Small Business Administration.

The reality of independent contracting is that you are in charge, for better or for worse. That can be scary for some, liberating for others. But a little research, a lot of persistence and a willingness to tackle the unexpected goes a long way.

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