Freelancer Tips

The Benefits and Challenges of Freelancing

Fiverr Team
July 20, 2017

For the past 10 years, Arestia Rosenberg (aka arestiar on Fiverr) has applied her unique background in film and television production, advertising, and media to one simple mission: passionate storytelling that makes a difference. She is currently a digital nomad, traveling the world while continuing to work as a freelance writer.It’s easy to dream of that #freelancelife.

Create your own hours, pick your own clients, build your own little empire...aaaaaah, freedom! As someone who has gone from full-time work to freelance, back to full-time work, and finally back to freelance again, I can assure you it can definitely have its highs, but it also comes with some lows. Sometimes you’re struggling for enough work to even make those hours your own.

Sometimes you can’t be choosy with clients because you just need the money. You might even get lonely. Every benefit to freelancing comes with its own challenges, but also the solutions to combat against them.  

Time Management

Benefit: Manage your own time. Freelancing means you don’t have to work 9-5 or any sort of set hours. You can decide to take that afternoon yoga class or surf in the morning before work. You decide when you work.

Challenge: Time management can be difficult or downright overwhelming.
When you don’t have set hours, it can be very easy to come off the rails and get to the end of the month when it comes to pay bills and realize you needed to work more. Or the opposite: You’re juggling a few clients and don’t understand how to balance when to do what work or you’ve taken on too much.

Solution: Put yourself on a schedule. Decide when you’re most productive and make that work time. I find I am most productive for a spurt first thing in the morning and then again between the hours of 2-6pm. For days when I know I have a lot of work, I make sure I am ready to work then, cranking it out. If I want to do something that cuts into that time, I don’t have to be rigid about it, but I’m mindful that I need to make that time up somewhere.

I know my monthly financial goals, so I make sure I have enough work coming in and the time dedicated to meet them. So if I’m not meeting my set project/hour rate one week because I am taking a day off, I better make it up another week to hit that monthly goal. And I make sure to enjoy that afternoon yoga class when I can because it’s important to be grateful for the flexibility to keep you in balance.

Working Remotely

Benefit: Work from anywhere. I’ve spent the last year and a half as a “digital nomad,” meaning I don’t have a home base and travel while working. Freelancing can sometimes mean you get to be location independent and work from anywhere. You can do a program like I did like Remote Year, Wifi Tribe, or Unsettled. Or if that’s not your speed, ditching the commute to work from home or the occasional café is its own luxury.

Challenge: It can be lonely. Once I finished Remote Year, I no longer had a community that I was traveling while working with and found myself pretty lonely. When you’re used to making friends at work and enjoy socializing like I do, you might find yourself missing the office.

Solution: Find a coworking space. There are other freelancers or solopreneurs like you out there looking to meet people! Joining a coworking space is a great way to meet people, find cool events, and even be more productive.

If you’re traveling around, I recommend looking at The League of Extraordinary Coworking Spaces or Croissant for location independent options, or if you’re not on the move, you can find a spot you like in your city, or check out WeWork which is one of the largest coworking companies with spaces all over the world.

Be Your Own Boss

Benefit: Be your own boss and choose your own work. You’re no longer assigned to difficult clients or put on projects you hate. You are in charge!

Challenge: It can be hard to find work and you might run into difficult clients. Especially in the beginning, you might find yourself taking on uncool projects or working with clients who make you cringe. Worse, you might be really struggling to find work to make ends meet.

Solution: Stay in action. You might find you spend half your time hustling to find work and that’s part of it. This is why platforms like Fiverr are so great because you’ve put yourself in a place where clients are looking for you! But don’t stop there. Let old employers, people in your professional network, and friends know that you’re looking for freelance work.

I’ve found it tremendously beneficial to have regular clients that I have more long term work with to make up the barebones of my monthly goal and then if I am looking to make more money that month for whatever reason, I go on more of a pitching and hustling spree. And it’s ok to take on less exciting work for because I find work begets other work.

Once you’ve built up more of a portfolio and reputation, start reaching out cold to companies you admire and want to work with. Send samples and let them know why you’re interested in working with them.

Make The Most Of It

Benefit: It’s all up to you. You don’t answer to anyone and you can make it all up based on your terms.

Challenge: It’s all up to you. You don’t have a team to rely on to help you with your work when times get tough. You are now CEO, as well as marketing, accounting, IT—you name it. If it goes right, it’s your win and if it goes wrong, it’s your fault.

Solution: Take it in stride and ask for help. I’ve found it has been a huge confidence boost to be freelance. I am really standing on my own two legs and making it all happen for myself. I celebrate that and you should, too. And I like wearing a lot of hats because it’s apart of what makes freelancing so rewarding. When I get stuck on something or am up against something not in my wheelhouse, I turn to my network.

Just today I was working with a client on their website copy and they had a few design questions. I turned to a few design friends who were able to help me out and my client was happy I could go the extra mile.

In return, I am always helpful with writing questions or quick help from my own network because we all need to support one another. The benefits of the freelance lifestyle often present challenges as well. But you’re resourceful! You’re a doer, so solutions and ways to combat these challenges are never far away. Utilize your network, your experience, and the internal resources you possess, and you can easily turn the freelance dream into a reality.

What are some of the biggest challenges you’ve encountered as a freelancer? How have you combat them? Share them with us, below!

Fiverr Team
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