From the shallow, it seems like freelancers are actually living their dream. Being able to call their own boss as well as not having a boss who’s always after you, is a desire which everybody has in today’s scenario.

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.

Why Freelancing?

  • Firstly, Working whenever you need,
  • Secondly, Making your own schedule of work,
  • Thirdly, Outside agreement,
  • Fourthly, Flying above the day-to-day grind,
  • Lastly, Not stickled to 9-5 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 people to care of a severe 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.

Job Security is threatened

Sure you’ll be able to pick up your kids from school without worrying about clearing it with your manager, but you might be worried about whether you’re making
enough to pay for their expenses this month instead.

The more the security of a regular paycheck as well as dependable benefits sounds good to you, the more you might not be cut out for the sometimes spontaneous nature of freelance work.

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But it doesn’t have to be an either/or situation.

Need a Freelancing Job? Here’s what all you need to do

Establishing Anchor Clients

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

Committing to an anchor client will narrow your freelance flexibility.

Practice long term freelancing

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-time 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.

Organization and Fertility Aren’t Your Vigorous Suit

If an organization, as well as 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 as well as 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.

What to do to make yourself organized?

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 knotty, arduous, or evocative of a manager breathing down your neck in a cubicle.

Some basic processes to help you stay focused as well as efficient will do just fine.

What’s Essential?

The most essential way to bring focus and organization to your freelance work is to regular, daily schedule.

The best part about sticking to a regular schedule as a freelancer is that you get to decide exactly what that schedule looks like.

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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 as well as stretching periodically through the day, or whatever else helps to give you work day flow.

Being a part of a team is what you miss being a freelancer

When it comes to selling the flexibility and benefits of freelance work versus the rigidity of a 9-5 job, there’s one vital part of an office culture that’s sometimes overlooked—working on a team and having regular social interaction with co-workers.

Every person’s mileage varies when it comes to social needs.

Some people flourish working alone, while other people can feel confined even in a busy workplace.

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

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.


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As a Senior Tech Enthusiast, I bring a decade of experience to the realm of tech writing, blending deep industry knowledge with a passion for storytelling. With expertise in software development to emerging tech trends like AI and IoT—my articles not only inform but also inspire. My journey in tech writing has been marked by a commitment to accuracy, clarity, and engaging storytelling, making me a trusted voice in the tech community.

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