Freelancing: the dream vs. the reality

May 15, 2018
5 minutes read

Many of us live in what we call the “freelancer economy.” It’s been estimated that within 10 years, the majority of the workforce in the United States will be freelancers. Among millennials, this is already true.

Whether you end up freelancing by choice or through necessity, it’s a way of working and living that offers many advantages over the usual 9-to-5 job where you’re working for someone else. But it also comes with its own set of challenges. Let’s look at some of the ways that freelancing is seen as a dream gig, and the realities behind them.

The Dream #1:

Freedom! Freelancing is freedom to do what you want, when you want, and above all, to be your own boss.

The Reality:

Yes, you’re not working for The Boss anymore. Now you are The Boss. And that’s great! But that’s also a double-sided coin. Yes, you get to make the decisions, but you have to make all the decisions. You’re not just the employee; you’re the general manager, the finance person, the accountant, the marketing guru, the social media manager, the CEO and the cleaning staff.

To be a successful freelancer calls for a lot more dedication than a typical office job. It takes discipline and organization skills. But, hey, since when does anything worth doing come easy? Now you’re running your own show, and you don’t have to put up with those cockamamie decisions from the corner office; you’re free to come up with your own cockamamie decisions!

The Dream #2:

You can set your own hours, and only work a few hours a day or a few days a week.

The Reality:

You may reach that point eventually, but it probably won’t be like that in the beginning.

Yes, you can set your own hours, but when you’re a freelancer, you also need to set aside time to do things other than your main work, i.e., your billable hours. You need to put time in finding your clients, managing your accounts and finances, marketing yourself, and all the other stuff an employer does for you.

For most freelancers, there isn’t a lot of breathing room to allow them to maximize their leisure hours. Complacency is dangerous. You might be in a great place with a pool of fine clients and a good cash flow, but things can change quickly. If one or two of your clients have a bad year and need to revise their budgets and reduce their freelancing costs, you can suddenly find yourself scrambling to replace that missing revenue stream. That’s why most freelancers don’t get complacent. It’s better to have more work than less. And that means taking Fridays off to go fishing is a luxury you probably can’t afford—at least not when you’re establishing yourself.

But, like any new business, after you put in the hard work in the beginning, you may eventually get yourself into a good situation with regular clients who will pay you top rates; and then you’ll be able to dial back on the amount of billable hours you work each day, or work fewer days a week. It can be done, and for those who get there, it can lead to a wonderful work-life balance that most office gigs can’t match.

The Dream #3:

You can pick and choose only the work you want to do.

The Reality:

You can certainly decide which industry you want to focus on, or areas you want to specialize in. That’s a big plus about freelancing. You steer the ship. But very few freelancers get to decide precisely what they do and who they work for. In the beginning, when you’re trying to get established and build a portfolio and a reputation, you likely won’t be in a position to turn down any reasonable work that comes your way.

You may even need to look outside your comfort zone. Many freelance writers and editors, for instance, have found that to make a solid living, they’ve had to diversify their offerings and create alternate revenue streams. So in addition to writing articles, they also do marketing copywriting, or work as proofreaders, or teach a course at a community college. If they had their druthers, they’d probably just be writing for publications or clients, but if there just isn’t enough work in that line, they patch together a number of revenue streams and make a go of it that way.

But stepping outside your comfort zone can often be a very good thing that pays unforeseen dividends. So you may not be able to be so picky about the work you do; but on the other hand, it may open the door for new opportunities, challenges and rewards that you never dreamed of.

The Dream #4:

You can work from home, and work in your pajamas!

The Reality:

Sure, you can. But most freelancers will still need to leave the house from time to time—to attend client meetings, business lunches and networking events—maybe several times a week. And on those days, you’ll need to leave the bunny slippers at home, clean up nice and put on your grown-up clothes.

But, yes, there can be pajama days. And those will be glorious days indeed.

The Dream #5:

As a freelancer, you can set your own rates and rake in big bucks—more so than a 9-to-5 job.

The Reality:

Obviously the key to making a real go of it as a freelancer is to be able to charge your top rates. But most freelancers won’t be able to set their own rates and get top dollars right off the bat. So don’t expect to be rolling in it the minute you put out your shingle.

You’ll need to establish yourself as an effective resource that clients can rely on time after time. Then, as you build your portfolio and make a name for yourself and get lots of client referrals, you can start raising your rates. It often takes time and lots of effort, but it is possible to get there.

The Dream #6:

You can take off as much time as you want.

The Reality:

Most freelancers don’t take real vacations. Even when they do get away, they bring their laptop with them, and the work tends to follow them.

Because your continued work flow is not guaranteed, many freelancers end up making hay while the sun shines and find themselves working a lot and not saying “no” to any client. If you’re a freelancer, you’ll probably work harder than you’ve ever worked.

But, if you’ve chosen to do this work, and it’s your passion, and you enjoy it, maybe that’s just part of the cost of being your own business. And with some good old nose-to-the-grindstone determination and planning, you may be able to ultimately get yourself into a situation where you can work intensely for most of the year and then take a month off to sail the Caribbean. Just be sure to communicate that to your clients well in advance, so they won’t be trying to reach you. (You might also want to change your cell phone number.)

The Dream #7:

Since you can work from anywhere, you’re free to travel and work while you’re away

The Reality:

Maybe. If you have a laptop, an internet connection and a phone with a good plan, sure, maybe you can polish up that report for your client and send it off while you sip red wine and munch on cheese and a baguette in a café in Montmartre.

But not everywhere has reliable internet or cell service. You may find that trying to combine freelancing and travelling offers more headaches than you anticipated. Or maybe you’ll find a way to make it work? After all, you’re intrepid and resourceful—you’re a freelancer!

So while the freelance life does indeed offer many advantages and freedoms, it also comes with its own set of challenges and accountabilities. But the rewards are there to be had. Just be sure that you understand the realities of the work as you work towards the dream.

By Jim Kelly

The information and tips shared on this blog are meant to be used as learning and personal development tools as you launch, run and grow your business. While a good place to start, these articles should not take the place of personalized advice from professionals. As our lawyers would say: “All content on Wave’s blog is intended for informational purposes only. It should not be considered legal or financial advice.” Additionally, Wave is the legal copyright holder of all materials on the blog, and others cannot re-use or publish it without our written consent.

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