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Four Signs You’re Not Cut Out For Freelance Work, and What to Do About It

Four Signs You’re Not Cut Out For Freelance Work, and What to Do About It

From the surface, it seems like freelancers are living the dream. Privileges like being able call their own shots and be their own bosses are more than a lot of people can ever hope for in the workplace, so if you’re freelancing, 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 that fit starts to feel a bit off for you? Here are some red flags that suggest freelancing might not be your thing. But don’t fear — these warning signs come with solutions if you’re determined to strike out on your own.

[Related: Got a Hobby? How to Turn What You Love Into a Paying Business]

1) The security of regular employment sounds good to you.

Accepting work when you want it, customizing 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 life circumstances that count on a predictable income stream, freelancing’s flexibility can become a double-edged sword.

What to do about it.

If the potentially up-and-down nature of freelance work makes you nervous, one surefire way to shore up the consistency of freelance income 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.

[Related: A Side Hustle Can Enhance Your Career]

2) Organization and productivity aren’t your strong suits.

If organization and self-directed productivity don’t come naturally to you, freelancing can quickly start to feel like a swamp of procrastination and looming, deferred work. The more stuck you become, the more you might start rethinking freelance work. But, with a little bit of adjustment and dedication, you can easily bring some of that office-style structure to freelancing.

What to do about it.

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

The most 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 every day, and more about sticking to a regular schedule when it comes to getting your varied freelance assignments done in a timely fashion. The best part about sticking to a regular schedule as a freelancer is that you get to decide exactly what that schedule looks like.

[Related: Meeting Your Strengths' Needs in Order to Thrive]

3) You feel isolated and miss being part of a team.

Every person’s mileage varies when it comes to social needs. Some people thrive working alone, while others feel isolated even in a busy workplace. 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.

What to do about it.

While freelance work, by nature, is never going to be as actively social as a regular job, it doesn’t have to be hermetic, either. 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 e-mail or voice phone calls) when appropriate and possible will add some much-needed connection to your day.

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 amenable to your specific needs.

[Related: What Does it Take to Become a Successful Female Entrepreneur?]

4) You’re not a natural salesperson.

Trying to sell your skills and experience without coming across as overly-confident or delusional can be nerve-wracking. For freelancers, every new client is a new job, which means your work life is an ongoing series of job interviews. If you’re not a natural-born salesperson, this can feel like a freelancing deal-breaker.

What to do about it.

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 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, look at your freelance job search as a chance to showcase what it is you’re capable of doing.

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. 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.

[Related: Making Money and Meaning: Freelance Writer Nancy Monson Turns a Side Job Into a Six-Figure Career]

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Written by Scott Morris for Skillcrush.

Skillcrush is an online community an interactive learning community that teaches coding to total beginners. Their classes give you the skills to make serious, positive career change into more fulfilling, flexible, and higher-paying jobs.


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