16 Things That Make Freelancing Tough & How To Overcome Them

Working as a freelancer can be awesome. You get to build your own schedule, work from wherever you want, and take on projects that are fun and interesting to you. And while there’s a lot of freedom in freelancing, there are also some downsides. The key is knowing how to navigate these tricky parts of the job. 

Here are 16  big things that can make freelancing tough, and how to overcome them:

Highs & Lows of Freelancing (an honest update) – YouTube
Takeaways
1. Identify your biggest challenges and create strategies to overcome them.
2. Build a strong support network of fellow freelancers or mentors for guidance and encouragement.
3. Practice effective time management techniques to maximize productivity and avoid burnout.
4. Develop strong communication skills to establish clear expectations with clients and manage conflicts.
5. Continuously upgrade your skills and stay updated with industry trends to remain competitive.
6. Maintain a healthy work-life balance by setting boundaries and prioritizing self-care.
7. Create a financial plan to handle irregular income and ensure long-term financial stability.
8. Embrace self-motivation and resilience to overcome setbacks and persevere in your freelance career.
9. Diversify your client base and income streams to mitigate risks and increase stability.
10. Stay organized by utilizing tools and systems that help you manage projects, finances, and deadlines effectively.
11. Be proactive in marketing yourself and building a strong personal brand to attract clients.
12. Continuously seek feedback from clients to improve your skills and deliver better results.
13. Prioritize professional development by attending workshops, webinars, and industry events.
14. Develop a thorough contract or agreement for each project to protect your rights and clarify expectations.
15. Cultivate a positive mindset and practice self-belief to overcome self-doubt and imposter syndrome.
16. Celebrate your successes and milestones along the way to stay motivated and inspired.

1. Managing Your Time

When you’re used to a 9-to-5 schedule, suddenly being responsible for managing all your time can be a big adjustment. You might find yourself working all hours or none at all! The way to combat this isn’t by creating a strict schedule, though (although that can help). 

Instead, try taking advantage of your increased freedom by experimenting with different methods until you find one that works for you. Try doing deep work for six hours every day, or working in three-hour chunks throughout the day—whatever feels right!

Building a successful freelance career requires dedication, perseverance, and a strong work ethic. However, freelancing is hard, and the challenges you face are not always what you expect. Check out our article on why freelancing is hard, but not for these reasons to gain insights into overcoming the common obstacles in the freelance world.

2. Learning New Skills

It’s a given that you’ll need to be willing to learn new skills from time to time. But even so, the idea of tackling new skills can be daunting for many freelancers. Here’s where having a mentoring relationship with another freelancer can help. One of my first freelance jobs was with a writer who had been doing freelance writing for ten years before I met him, and he helped me out on my very first project by being willing to share his tips, tricks, and real-world experience. 

Working with him showed me how easy starting from scratch could be if I just applied the experience he had gained over the last decade. Later on, I’d be able to pass along that same knowledge to others who wanted to learn more about freelance writing.

3. Being Too Hard On Yourself

The truth is freelancing can be hard and freelancers tend to be their own worst critics. We put too much pressure on ourselves to succeed and win each and every project we take on, which can be exhausting at times. 

The best thing you can do, especially when you’re just starting out, is not to get down on yourself when things don’t go your way or the way you expected them to, but rather, learn from those experiences and make changes accordingly to improve your business.

Impostor syndrome can be a significant hurdle for freelancers, affecting their confidence and performance. If you’re struggling with self-doubt and feeling like a fraud, we’ve got you covered. Discover effective strategies in our guide on how to deal with impostor syndrome in freelancing to regain your confidence and excel in your freelance career.

4. Feeling Isolated

Ultimately, the biggest challenge a freelancer will have to deal with is isolation. This goes back to the point above about accountability. People who work in an office setting or otherwise have people they can see on a regular basis will have a social network to help them stay focused and accountable. 

Freelancers rely on themselves for everything, so it’s up to you to create your own social structure. Most freelancers will likely turn to communication technology like Skype, instant messaging, and email, but that’s only the beginning of what you could do to make yourself feel part of a community. 

The more you find ways of staying connected—physically or virtually—the easier it will be for you to stay focused, motivated, and productive at work.

5. The Pay Isn’t Always Steady

This is a big one. We’re all used to having a regular paycheck every two weeks. But when you’re freelancing, the pay can be inconsistent. If you’ve got a client who isn’t paying on time, or you’re between projects, it can be tough to keep your finances in line. One thing I like to do is keep an eye out for jobs that have bonuses associated with them. 

This way, at least if I don’t get paid right away, I’ll get something extra down the road. And if you have trouble finding clients, maybe it’s time to refresh your portfolio!

One way to overcome this is to get as many clients as possible, and then set aside some of the money you earn so that it’s there when you need it.

6. You Don’t Always Know What The Future Holds

Freelancing comes with a lot of responsibilities, but one of the toughest ones is making sure you have enough money to pay your bills.

You don’t have a steady income from a full-time job, and it’s up to you to make sure you’re making enough money to cover expenses. You might feel like this pressure is hard to handle, but there are some things you can do to make it easier:

  • Make a list of all your expenses and compare them against your monthly income
  •  Figure out which expenses are “needs” and which are “wants,” then cut down on anything that’s not necessary
  • Set aside money each month so you have a “cushion” in case something unexpected happens!

Many people hesitate to explore freelancing due to misconceptions and fears surrounding it. The truth is, freelancing is not as scary as everyone makes it out to be. In fact, it can be a fulfilling and rewarding career path. Learn more about the realities of freelancing in our article on why freelancing is not as scary as it seems and embark on your freelance journey with confidence.

7. Finding Work

One of the most difficult aspects of freelancing is finding work. Whether you’re new to freelancing or have been doing it for years, finding clients can be challenging.

Make sure you’re taking advantage of all the opportunities available to you. If you’re a graphic designer, for example, have you made a profile on Dribbble? What about submitting your work to creative directories like Awwwards? Are you connected with other designers on LinkedIn? Building your portfolio and sharing it with your network will open up a lot of doors for potential clients.

8. There’s No Schedule

How to overcome it: Set a structure for your day. While freelancing lets you set your own schedule, this freedom can make it hard to keep yourself disciplined and accountable. A lot of freelancers find that by creating a routine, they’re able to stay focused and motivated throughout the day.

It helps if you have a dedicated workspace in your home, but even just setting aside a corner of your living room can help give you a sense of consistency during work hours.

9. You Have To Negotiate Every Payment

The struggle is real. Freelancers have to negotiate every payment. It’s a part of freelancing that can be really hard, especially if you’re not used to being in the position of asking for what you want.

It’s important to remember that your clients are businesses, and they want to make a profit, too. So don’t feel bad about asking for what you think is fair—but do it nicely! If you ask in a way that shows respect and responsibility, they’ll be more likely to work with you. The best way to get paid fairly as a freelancer is by negotiating well and getting on your clients’ good sides.

10. You Have To Do All Of Your Own Taxes

If you’re employed by someone else, they take care of your taxes for you. When you freelance, you have to do all of your own taxes. You have to pay estimated taxes four times a year, and if you don’t do this right, the IRS will come after you with penalties and fines.

It’s not necessary to go out and get an accountant just yet. If you’re just getting started on your own as a freelancer, use tax software like TurboTax or TaxAct to help guide you through the process. Also, try services like FreshBooks or Wave, which provide tools for managing your business income and expenses throughout the year.

Freelancing comes with its own set of unique challenges, and it’s important to be prepared to navigate them. If you’re wondering why freelancing can be surprisingly difficult and how to overcome the obstacles, our comprehensive guide has got you covered. Explore why freelancing is surprisingly difficult and how to deal with it to gain valuable insights and strategies for a successful freelance career.

11. Not Getting Enough Work

This feels like the obvious one, but it’s the one that’s probably kept you up nights the most. You’ve put all your eggs into your freelance basket and you’re waiting for things to work out, but nothing is coming in.

What can you do?

  • Get a side gig: Find a way to make money on the side while you’re waiting for work to pick up. There are many ways to make extra cash online, and they can even be ways to network with people who might hire you as a freelancer!
  • Build your portfolio: Don’t have much of a portfolio yet? You can still start building one right now by doing volunteer work for non-profits. It won’t pay, but it will give you something to show potential clients who are considering hiring you. And if you do good work, they just might become a regular client!
  • Take on pro bono work: If you’re looking for more paying work, but your portfolio is lacking, consider taking on pro bono clients. You’ll get paid less than usual (or not at all), but it will give you some experience and more pieces for your portfolio that will help you get higher paying jobs in the future.

12. You Need To Be A Jack Of All Trades

When you freelance, you are the business. Not only do you have to provide your core service, but you also have to be in charge of your marketing, accounting, and more! This can be overwhelming and make it hard to feel like you’re doing anything well.

The best way to cope with this is to prioritize what is most important—your work. It’s a good idea to outsource or hire help for things that aren’t your core service, like bookkeeping and administrative tasks. These tasks take up time that could otherwise be spent earning money or growing your business.

13. Finding The Right Clients

You might be wondering: how do I get started? Where do I find people who need my help?

At first, this may seem like a huge mountain to climb. It is, but it doesn’t have to be that hard. One of the best ways to find clients is through referrals, so start by reaching out to people you know. Let them know that you’re looking for work and ask if they know anyone who needs help with [type of work].

You can also find clients in places where your target market hangs out online. For example, if you freelance as a social media manager, try joining some Facebook groups for small businesses and letting them know what you can offer.

14. Working With Difficult Clients

The next thing that makes freelancing tough is working with difficult clients—the ones who want to micromanage every detail of your work or who push back on deadlines and rates..

Having a strong contract is probably the most important thing you can have when it comes to working with difficult clients. Your contract will spell out your rights as a contractor, as well as what the client is expected to provide in order for your contract to be fulfilled.

It also spells out how these issues will be handled if they come up. So if your client refuses to pay on time, you can point them to the contract that says they must pay on time in order for services to continue being rendered. It helps take some of the emotion out of the situation by providing an impartial document that both parties agreed on at the beginning of their relationship.

15. Lack Of Feedback

When you’re starting out, it can be difficult to get a steady stream of clients, and when you do not have regular clients, it can be difficult to get feedback on your work.

This is especially true if you’re working with a marketplace like Upwork where potential clients are looking for freelancers with lots of experience. It can be challenging to break into the market in the first place.

If you’re struggling to find clients and get feedback on your work, try offering discounted or pro bono services for friends and family members. This will give you an opportunity to show off your skills and get some testimonials for your portfolio.

Also, try reaching out to businesses that are just getting started or are growing quickly—they may be willing to take a chance on someone with fewer reviews but a great rate!

Freelancer burnout is a real concern, but there are proven steps you can take to overcome it and maintain a healthy work-life balance. Our article on 8 proven steps to overcome freelancer burnout provides practical tips and techniques to prevent burnout and sustain your productivity and well-being as a freelancer. Take charge of your mental health and thrive in your freelance journey.

16. There’s No Real Job Security

When you’re sick, and you’re a freelancer, it’s not a given that you’ll get any paid time off. Sure, your boss might be understanding, but if they don’t have to pay you for the time off, then there won’t be much incentive for them to grant it. And if you’re in a position where the only person who can do your job is you, then there’s no way around it: it doesn’t matter how sick you are—you’ve got to get up, get to work, and get back on the horse. 

What’s worse is that in some cases, when your freelancing work is dependent on something like web traffic or ad revenue, not being at your best could mean losing out on some of your income.

This one comes with a few possible solutions. First, make sure that you have a backup plan in case this happens so that you don’t have to do all the work yourself. If it’s an illness that requires medical attention, make sure that treatment is an option (or even just an over-the-counter remedy). Second, take extra care of yourself when times are good.

Final Thought

In short, It may seem like there are a lot of things that can hold you back and make freelancing difficult. But don’t be disheartened. Freelancing is still more than possible and you can overcome those hurdles to continue doing what it is you love. Just remember the tips and tricks above, ask for help when you need it and remember why you started in the first place!

Further Reading

Here are some additional resources that you may find helpful for further reading:

Time Management Tips for Freelancers: Discover effective time management strategies specifically tailored for freelancers to enhance productivity and maximize efficiency in your work.

Overcoming Common Fears About Freelancing: Explore the common fears that people often have about freelancing and learn practical ways to overcome them, allowing you to pursue your freelance career with confidence.

Avoiding Common Freelancing Pitfalls: This article highlights common pitfalls that freelancers may encounter and provides valuable insights on how to avoid them, ensuring a smoother and more successful freelancing experience.

People Also Ask

Client Who Doesn’t Pay On Time?

In your contract, have a very clear payment schedule so there’s no confusion about when the payments are due, and come up with a plan for what happens if they don’t pay on time. And make sure there’s an interest rate on those late payments—they need to understand that it’s not just annoying for you when they pay late, but that it actually costs you money.

Client Changes Their Mind Mid-Project What To Do ?

That’s why you have contracts! Make sure your contract includes a provision for how many revisions are included in the original project price, and how much any additional changes will cost. Also, include a clause that details how quickly you expect them to give feedback and approve work so that your work isn’t held

How Do I Set My Rates?

This can be a tough one, especially if you’re just starting out. If you don’t have any experience yet, the best way to figure out your rate is by researching what others in your field are charging per hour and going from there. 

How Do I Get Clients?

One of the best ways to get clients is by networking like crazy—making sure everyone knows what you do and that you’re looking for work! You can also use social media to find companies looking for freelancers or post ads on sites like Craigslist or Fiverr.

What Is It Like Being A Freelancer?

It’s pretty great if we do say so ourselves! You set your own hours, you get to work with great people who are passionate and excited about what they do, you have freedom in how you approach clients.

Working From Home Is Super Isolating?

Overcome it by Getting a dog or cat to keep you company and make working from home more fun for you!

It’s Hard To Avoid Distractions?

Overcome it by: Creating a distraction-free workspace in your own home, ideally with a door that closes.

You Need To Work To Find New Clients All The Time?

Overcome it by: Networking, networking, networking! Go to meetups, get on social media, and do all you can to put yourself out there!

There Are No Hard And Fast Rules For How Much You Should Charge Your Clients?

Overcome it by Researching what other people in your field are charging and using that as a starting point for what you charge your clients.

Do I Need Any Special Equipment?

All you really need is a good computer (we recommend Macs) and an internet connection.

How Can I Get Clients To Recommend Me?

Getting clients to recommend you can be difficult. You want to complete the project, but you don’t want to bother the client and make it seem like you’re just trying to get a recommendation from them. So, how do you get a recommendation without bothering the client?

There are a couple of things that you can try. One, you can offer the client a discount for their next gig with you if they can provide a reference that turns into a sale. 

Two, you can ask them if they know someone who would be interested in working with you and offer them a discount as well. 

Three, you can ask them if they’d be willing to write an article about your work or give an interview on your site. Whatever method works best for your situation!

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