You know what they say: the grass is always greener on the other side of the fence. And when that fence is the brick, steel, or glass facade of your office building, the grass outside can start to seem like a veritable playground where freelancers and full-time telecommuters go to frolic.

However, ask any freelancer — at least any who’s been working remotely or from home for more than, say, a couple of years — and you’ll find that this lifestyle isn’t for everyone. Before you quit your role as a corporate cog and go running for greener pastures, ask yourself these questions to find out if freelancing is a good fit for you.

Am I Truly a Self-Starter?

Sure, you might have phrases like “self-starter,” “takes initiative” or “works well independently with minimal supervision” on your resume, but be honest. Can you motivate yourself to power through your daily to-do list without being under the watchful eyes of coworkers or supervisors?

Motivating yourself can be much more difficult than you might think. That’s particularly true if you pride yourself on “working well under pressure” or having a tendency to procrastinate. Keep yourself accountable by quantifying your productivity. There are tons of ways to do this, and it may take some experimentation before you find the method that works best for you. But for some folks, there’s simply no better motivator than that biweekly paycheck with a corporate logo in the upper left corner. And that’s OK!

Do I Need Social Contact to Thrive Professionally?

Whether you believe that the world is divided into extroverts and introverts, or that each of us falls somewhere on the spectrum between “supreme loner” and “extreme people person,” it is true that some of us work better when we’re by ourselves. Some of us thrive on not just collaboration — that’s possible when telecommuting, thanks to tech — but on social contact and the companionship, even if it’s silent, of colleagues.

Part of this has to do with the fact that freelancers or those who work from home don’t tend to “dress the part.” And that can not only affect your performance on the job, but it can be a psychological drag, too. Some folks find that they really miss having a reason to do their hair and makeup, or showing off their fashion sense at the office.

And if you live alone or don’t have an active social life, isolation can set in pretty quickly. In some ways, introverts might do better if they “have to” head into the office on a regular basis.

Do I Have Someplace to Host Clients?

Going it on your own professionally offers a number of challenges. Smaller-scale freelancers can work from their home office or the local coffee shop, but if you must meet with clients or potential clients, host meetings, or give presentations, you’ll need access to a space that offers all the amenities.

“In a business meeting, like in life, first impressions can mean the difference between a successful partnership or a meaningless encounter,” say the experts at

Make sure that you’re able to make the best possible first impression — whether you are Skyping with an international client or laying out a proposal in person, you will require a dedicated, professional environment to use when necessary.

Can I Find a Balance Between Flexibility and Distraction?

Hands down, one of the biggest perks of freelancing or telecommuting with a flexible work schedule is the ability to take time during “normal business hours” to do what needs to be done. This includes picking up the kids from school, shopping when the grocery store isn’t an after-work madhouse, attending doctor’s appointments or just being able to hit the gym when the mood strikes.

Flexibility can be a slippery slope, however. Sure, it’s convenient to be able to throw a roast in the crockpot between conference calls. But unless you safeguard against complacence, you might find yourself “procrastibaking,” “procrasti-cleaning” or even “procrasti-watching-daytime-TV-because-Will-Smith-is-on-Ellen.” 

Too, many freelancers suffer from a sense of being constantly on the clock. Because they never officially start work, they never officially stop, either. For most folks, it’s a good idea to set — and abide by — fairly strict working hours. Build in breaks during which you take care of chores like laundry, chauffeuring children to and fro, or prepping for dinner. But if you take an hour off midday to catch up on last night’s episode of America’s Got Talent, work an extra hour in the evening to compensate. Otherwise you might find your productivity suffering.

Takeaway Thoughts

There are ways to stay connected while working from home, of course. And plenty of remote employees or independent contractors thrive when they have more control over their schedule, working environment, and contact with colleagues. Just know that the grass on the other side of the freelance fence isn’t necessarily as green as it may appear from your office window. It all depends on your personality and your perspective.

Richard is an experienced tech journalist and blogger who is passionate about new and emerging technologies. He provides insightful and engaging content for Connection Cafe and is committed to staying up-to-date on the latest trends and developments.