4 Ways To Know If You’ll Loathe Freelancing

By Scott Morris

From the surface it seems like freelancers are living the dream. Being able call their own shots and be their own boss are more than a lot of people can ever hope for in the workplace, so if you’re currently freelancing (or planning to do so), congratulations! It sounds like you’ve got it made. Of course, things often look different from the inside. While freelancing is a perfect fit for some people, what happens if—for you—that fit starts to feel a bit off? Here are some red flags that suggest freelancing might not be your thing. But don’t fear—these warning signs you shouldn’t freelance come with solutions if you’re determined to strike out on your own.

The Security of Regular Employment Sounds Good to You

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Accepting work when you want itcustomizing a schedule that suits your unique needs and outside obligations, and flying above the day-to-day grind of regular, nine-to-five employment—these are the key perks of freelancing, and exactly what makes it an appealing work option for so many people. But what if factors in your life make this kind of extreme flexibility feel too uncertain? If you have children or other dependents, a chronic health issue, a mortgage to pay, or any other life circumstances that count on a predictable income stream, freelancing’s flexibility can become a double-edged sword. Sure you’ll be able to pick up your kids from school without worrying about clearing it with your manager, but you might be worrying about whether you’re making enough to pay for their expenses this month instead. The more the security of a regular paycheck and dependable benefits sound good to you, the more you might not be cut out for the sometimes spontaneous nature of freelance work. But it doesn’t have to be an either/or situation.

What to Do if You’re Craving Freelance Job Security

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If the potentially up and down nature of freelance work makes you nervous, one surefire way to shore up the consistency of your freelance income and workload is to focus on establishing an anchor client. Anchor clients are individuals or businesses you develop an ongoing relationship with and do a steady amount of work for every month. Closer to having a regular part-time job, committing to an anchor client will narrow your freelance flexibility—if you’re dedicating a significant amount of time each month to one job, you’ll obviously be limited in what else you can take on—but if you aren’t comfortable with the feeling of each month being different and unpredictable, using an anchor client as the foundation of your freelance work will give you a reliable income base while adding smaller and shorter-term jobs to supplement it.

As for where and how to find anchor clients, look at clients you’ve enjoyed working with so far and identify opportunities where you can do more work for them and get further involved with their business or organization. By billing yourself as able to shoulder an employee-style workload without requiring a full-time employee’s salary and benefits, you’ll be a good fit for clients who have work available but aren’t currently in the position to hire someone full-time. If those opportunities aren’t jumping off the page from your list of previous or current clients, start actively seeking out individuals or companies looking to hire longer-term freelancers.

Meanwhile, when it comes to freelancing and security, it’s helpful to keep in mind that the grass isn’t necessarily greener on the other side. As this Forbes article points out, the conventional wisdom of a full-time job equaling financial security is overblown at best. Relying on a single income stream means that if anything happens to that single stream you’re out in the cold entirely. While freelance income can fluctuate, your diversity of income sources is its own kind of security that doesn’t exist in the world of singular employment.

Organization and Productivity Aren’t Your Strong Suit

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If organization and self-directed productivity don’t come naturally to you, freelancing can quickly start to feel like a swamp of procrastination and be looming, deferred work. The more stuck you become, the more you might start rethinking freelance work and looking wistfully to the structures of full-time office life. But with a little bit of adjustment and dedication you can easily bring some of that office-style structure to freelancing—and, if you take a moment to step back and get some perspective, you might see that your productivity is better than you think (and even on-pace with what goes on under the watchful eye of a supervisor).

What to Do if You’re Feeling Disorganized and Unproductive

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You’ll never feel organized as a freelancer until you implement some organizational systems—that’s simply a fact. But those systems don’t need to be anything overly complicated, onerous, or reminiscent of a manager breathing down your neck in a cubicle. Some basic processes to help you stay focused and efficient will do just fine.

The essential way to bring focus and organization to your freelance work is to establish a regular, daily schedule. This may seem counterintuitive (since not being tied to a regular schedule is one of the hallmarks of freelancing), but this is less about doing the same tasks for the same people day in and day out, and more about sticking to a regular schedule when it comes to getting your varied freelance assignments done in a timely fashion. And the best part about sticking to a regular schedule as a freelancer is that you get to decide exactly what that schedule looks like. Whether it’s using a daily to-do list, taking some time on Sunday evening to plot out your calendar for the week, deciding on fixed chunks of work time followed by planned breaks, building in time for walks and stretching periodically through the day, or whatever else helps to give your work day flow and definition, picking out some of these daily rituals and sticking to them will help your day feel like less of a chaotic montage—knowing for sure what you’re going to be doing and when you’re going to be doing it removes the randomness and guesswork that leads directly to procrastination.

But chances are—even if you stand to benefit from introducing a bit more structure to your daily work schedule—you’re probably more productive than you think. From the perspective of working from home or a coworking space, it can sometimes feel that full-time office workers spend their entire eight or more hours a day in a productive fugue state, but statistics suggest otherwise. A 2016 study of nearly 2,000 UK office workers found that the average amount of time spent on work during an eight hour work day amounted to a whopping two hours and 53 minutes—the human brain, it seems, is simply not wired to concentrate on tasks for hours at a time. That being said, while the breaks you take in between bursts of productivity might stand out and seem excessively long when you’re working for yourself and not immediately accountable to an in-person supervisor, you’re probably on pace for what’s going on in a full-time office environment—in fact, you might even be outpacing your full-time peers.

You Feel Isolated and Miss Being Part of a Team

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When it comes to selling the flexibility and benefits of freelance work versus the rigidity of a nine-to-five, there’s one vital part of office culture that’s sometimes overlooked—working on a team and having regular social interaction with coworkers. Every person’s mileage varies when it comes to social needs (some people thrive working alone, while other people can feel isolated even in a busy workplace), but if you’re the kind of person who gets lonely easily, adjusting to the lone wolf nature of freelancing can be a hard pill to swallow—going to the kitchen sink by yourself to get a glass of water just isn’t the same as a trip to the water cooler with colleagues. But does an onset of loneliness mean you need to ditch your freelance business for an adjoining cubicle? Not necessarily.

What to Do if You’re Feeling Isolated as a Freelancer

working love it GIF by WeWorkWhile freelance work, by nature, is never going to be as active, social or team-centric as a regular job, it doesn’t have to be hermetic either. Although freelancers aren’t working on a team per se, no work happens in a vacuum. On any given day you’ll be interacting with clients and other freelancers or employees involved in the projects you’re working on. If you feel your social meter running low, something as simple as communicating with these people through video chats (versus email or voice phone calls) when appropriate and possible will add some much-needed connection to your day. And don’t feel shy about injecting a reasonable amount of non-work related small talk in these interactions. Of course you don’t want to veer into the realm of oversharing, but some basic, “how was your weekend?” or “read any good books lately?” questions can go a long way to establishing a personal connection with others, even if you’re not working side by side in the same office.

And speaking of working side by side, if you find the confines of your home office are getting you down, consider looking into joining a coworking space—by coworking, you WILL be working side-by-side with other human beings, but not for the same company or on the same projects, which means all of the social benefits with none of the workplace politics or drama. In addition to coworking, you can also mesh your work and social life by seeking out industry-oriented meetups in your area. Freelancing won’t give you the same built-in social network that you’ll get out of a full-time workplace, but freelance flexibility gives you the opportunity to create one for yourself that can be even more amenable to your specific needs.

You’re Not a Natural Salesperson

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It’s not just you—lots of people don’t like anything resembling job interviews. Trying to sell your skills and experience without coming across as overly confident or delusional can be nerve-wracking. The good thing about regular employment is that interviews only come up when you’re looking for a new job, maybe once every few years or even less. For freelancers though, every new client is a new job, which means your work life is an on-going series of job interviews. If you’re not a natural born salesperson, this can feel like a freelancing deal breaker—just like everything else that comes with freelancing’s flexibility, landing clients is all on you, which means if you want to get paid you’re inevitably going to have to sell your services. If selling makes you feel about as comfortable as diving into a pile of thumbtacks, it might be tempting to just get a singular job interview over with and retreat back to the nine-to-five. But before you take any extreme measures, consider that selling your skills doesn’t have to be as bad as all that.

What to Do if You Don’t Feel Comfortable Selling Your Skills

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Something crucial to keep in mind when it comes to landing freelance clients is that you’re not going door-to-door selling gimmick kitchen knives—you’re actually providing essential services that employers want and need. Instead of feeling like you’re pestering potential clients by selling them on something they don’t want, simply look at your freelance job search as a chance to showcase what it is you’re capable of doing. One of the best ways start doing this is to really drill down on your portfolio game. Between creating your own portfolio site and establishing a presence on portfolio services like Behance and Dribbble, when you court clients you’ll be marketing your services in a crisp, clear way that doesn’t feel like an overbearing sales pitch—you’ll simply be letting your work tell its own story.

Similarly, another effective way to naturally showcase your abilities sans marketing speak is to stay busy with personal projects and pro bono work between paid gigs. Even doing one job a year for a nonprofit organization or an unpaid project that speaks to you personally will give you a chance to hone your skills without the pressure of selling them, while also giving you concrete examples of work to point to when it is time to sell to paid employers. Remember, there’s nothing phony about selling your very real services. As intimidating as job interviews can be, they exist because employers want to hire people. Think of landing your freelance work more like interviewing for a long-term job than selling someone a product that they didn’t ask for—there’s always anxiety around trying to get hired, but if you remove the pressure of sales stigma, it can feel a lot less daunting.

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