The 27 Dilemmas Every Freelancer Faces And Ways To Solve Them

The freelance life: it’s got its ups and downs.

If you’re a freelancer, you know how much stress and anxiety come with operating in a world of unpredictable hours, unreliable clients, and the feeling that you can never get totally caught up in your work. But you also know that independence and freedom are worth it.

I have assembled some of the most common freelance dilemmas along with tips to help you navigate them. We hope that they help make your freelance life easier!

Table of Contents

1. I Have No Idea How To Price My Services? 

Pricing is one of the trickiest parts of freelancing, especially if you’re just starting out. There’s no magic formula for what to charge, but there are ways to think about pricing that can help clarify things for you

First, figure out what your hourly rate needs to be in order for you to cover basic expenses (don’t forget health insurance!) with some room for savings or investments in your business. Then think about how many hours of actual work time you can realistically put in each week (not including marketing time or other administrative stuff). Divide your hourly rate by the number of work hours per week; the result is the minimum project fee you should charge.

2. How Do I Politely Ask For Payment?

There are some situations where it’s almost guaranteed that you’ll be paid on time: when you have a signed contract in place with a large company, or when you have an established relationship with a client who’s always paid you promptly in the past. But what about those situations where you aren’t sure if the client will pay—or when they’ll pay?

You’ve got nothing to lose by being transparent about your concerns early on. When you first bring up money with a new client, make it clear that getting paid is your priority. If the client says they can only pay after the work is submitted, ask them to put it in writing—then sign a contract so that both of you have a document to refer back to in case there’s ever any confusion about payment.

3. You’re Worried That Your Client Won’t Like Your Work?

The best way to avoid this kind of worry is by having a good brief and clear contract in place before you begin working for the client. Having these things will help set expectations from the start so that neither

4. Figuring Out What to Charge?

Doing your research is essential here—and don’t be afraid to ask questions! When I was first starting out, I asked other freelancers what they charged for projects similar to mine (and at the same level of experience), and that gave me a good idea of what was reasonable in my area. 

Don’t be afraid to talk about money with your fellow freelancers—once you get started on your own, you’ll see that this is often considered an unspoken “rule” in the freelance community. If something seems too good to be true, or too low

5. How Do You Get A Project That’s Not Too Appealing?

First of all, don’t panic! You’re not alone. Money is the number one issue for new freelancers, and it’s also the top reason why people give up freelancing as a career choice.

But there’s hope! And there are options! First of all, many (if not most) freelancers have to take on a project or two that they don’t really like. That’s just how business works—and it’s especially true when you’re starting out because you haven’t yet built up a client base and a stable income.

So here’s what you can do:

Take the gig! It might not be your dream job now, but at least you will have a steady income while you look for more interesting projects that pay better—AND the experience will help build up your portfolio so you can get even better-paying jobs in the future.

6. Feeling Like You’re Not Good Enough

We’ve all been there. You need to write a piece, and the voice in your head sounds like your fifth-grade teacher is telling you you’re terrible at writing, and this piece is going to be the worst thing anyone has ever seen.

You know what? Most of us don’t get into freelance because we’re already perfect at it—we get into it because we want to learn and grow as writers. So if you’re feeling like you’re not good enough, just remember that this is an opportunity for growth, and that’s a good thing!

7.  Feeling Like Your Work Isn’t Worth What You Should Be Charging?

This one’s easy: It’s worth whatever someone is willing to pay for it. If that doesn’t convince you, ask yourself this: Would you pay someone else for the work you’ve done? If the answer isn’t a resounding yes, then maybe you need to rethink your approach next time around. And if the answer is yes, then why wouldn’t someone else be willing to pay for it?

8. The Client Doesn’t Get Back To You?

A client doesn’t get back to you, so you don’t know if you’re still working on the project or not.

Solution: Don’t chase clients down. Let them come to you. Write them a friendly email stating that your time is valuable and you’d like to know whether you’re still working with them or not. If they don’t respond in a reasonable amount of time, move on.

9. You Have A Client Who Takes Forever To Get Back To You But Pays Well

You can’t wait around to hear back from them while they take their sweet time, because you don’t want to lose other opportunities. But you could lose money by making the wrong call.

This is one of the most difficult situations in freelancing because there’s no perfect answer. But in general, you should try not to work with clients who are notoriously unresponsive—the opportunities that come from these clients aren’t worth the massive headache they cause you later on. 

If someone isn’t willing or able to be responsive now, it’s likely that they won’t be any more responsive later on, either. And even if their money is good, it’s not worth the stress and lost time that comes from working with them.

10.  A Project Goes Over Deadline Due To Factors Outside Your Control And You Need More Time?

First, try to predict how long the extension is going to take. If possible, ask for the extension on a per-project basis. If you’re working on multiple projects simultaneously and one of them is delayed, offer a discount on that project and make sure that it doesn’t impact the rest of your schedule.

11. No One Knows Who I Am?

Solution: Network! Get out there and let people know about you—go to events, do some free writing for local businesses, tell your family and friends that you’re available for hire.

13. I Don’t Know Where to Find Jobs? 

Solution: Check out job boards like UpWork, Fiverr, or, or join a business community like BNI (Business Networking International).

14. I Can’t Find The Time To Do My Work? 

Solution: Schedule your time. If you don’t have a calendar system yet, you need one ASAP to keep yourself organized and track all your deadlines.

15. I Feel Unproductive?

Solution: Make sure all of your work is as efficient as possible with tools like Grammarly and Hemingway App—no more spending hours searching for that quotation mark key!

16. I Don’t Know How To Present My Work In A Way That Makes Me Look Like An Expert?

Bad news: Clients often judge you based on aesthetics alone. The good news (I think): That means you don’t have to be the best at what you do—you just have to present your work like you are a total expert. The key here is consistency. If you’re a designer, make sure your portfolio uses your own design aesthetic throughout; if you’re a writer, use the same house style for all your writing samples.

16. I Dont Have Enough Work?

Sometimes there’s just not enough work to go around. Whether you’re just getting started and haven’t built up your network yet or you’ve been freelancing for a while and your favorite clients have hit a dry spell, it can be tricky to find enough work.

Solution: Start looking for work as soon as possible! This can be done with Upwork, LinkedIn, or even by cold-calling companies or sending out emails. You should also try to expand your repertoire of skills—and if you don’t currently know how to do something you think will be helpful (like HTML), learn it!

17. No Clients

In order to make money for your projects, you need clients who will pay for those projects. But how do you get clients? One way is by networking with people in your industry, whether in person or online. Another is by checking job boards for freelance work. 

If you’re just starting out, consider trying out a few different platforms—some are better than others at matching freelancers with the right clients based on the type of work they’re looking for (and vice-versa).

18. Clients Who Don’t Pay (Or Pay Late)

This is a problem that a lot of freelancers run into at some point or another, and it can be really frustrating to deal with. When clients don’t pay or pay late, it can throw off your whole budget—which is why it’s important to have a good contract in place before you start working on any project. 

Make sure that it specifies when payment needs to be made and what the consequences are if payment isn’t made within that time frame

19. You’re Not Sure If You Should Just Quit Writing And Get A Job?

Do your research before you commit to freelancing full-time. There are a lot of costs to going freelance, and it takes time to develop a steady client base. Additionally, freelance writers earn an average of $20 per hour (according to the Bureau of Labor Statistics), which might not be enough for you to support yourself, depending on where you live. 

Research how much other freelancers make in your city and state, how much you’ll need to make to comfortably support yourself, and what it will cost for you to go freelance before you quit your day job. If it doesn’t look like freelancing is currently a financially viable option for you, then don’t quit your job!

20. You’re Working On 2 Projects At Once And Realize You’ve Accidentally Sent A Client The Wrong Document?

Don’t panic! First things first: reach out to your client immediately to let them know they have the wrong document. Then, get back on track. If you’re having trouble doing so, try taking a small break before trying again—it can really help clear your head and set your priorities straight. 

Try to avoid making this mistake in the future by keeping better track of which documents go with each project, even if it means color coding them or writing yourself a note in WordPad when you start each project.

21. You’re Working On A Project, And A Client Texts You Asking For An Update Or Has Other Urgent Questions?

Be upfront with clients about check-in times, especially if they want to text you during work hours (if they don’t, it’s okay to let them know that too). If the client is insisting on that.

22. Please Send Us An Invoice For The Hours You Worked?

There are tons of helpful invoice templates online that can guide you as you fill in the blanks for yours. The main thing is to make sure it contains the details about the work you did, what you charged, any extra fees or discounts, your business name and contact information, and all relevant payment terms. If you don’t have your own business name, consider just putting your full name on it instead.

23. Client Is Very Demanding? 

Solution: Be firm with this client right up front by letting them know that payment is expected upon completion of the project (or upon receipt of the first draft), not at the end of revisions. Be polite but firm when you send them an invoice as soon as the work is

24. You’re Having Trouble Keeping Up With Your Clients

Set up a calendar, and try to set times each week for scheduling calls and meetings.

25. You Have A Steady Stream Of Work, But Not Enough Money To Live On

Have an open conversation with your boss about salary and compensation. Tell them what you think you’re worth and why. Then listen to their feedback and come up with something that works for both parties. If they don’t have anything to offer you, consider looking for other work or working more freelance hours.

26. You Don’t Know How To Set Professional Boundaries With Your Clients

Be honest and upfront about your availability and timelines, so there are no surprises down the line. Add in clauses in your contracts that protect you from unreasonable expectations from clients, like asking for unlimited revisions or expecting you to be available 24/7. Don’t be afraid to say no if a client is overstepping those boundaries—just make sure you back it up with a clause in your contract if possible!

27. I Don’t Have Any Money But I Want To Be A Freelancer?

Most people don’t have any money when they start, but there are some things you can do to make the process easier for yourself.

First, save up as much as you can before you quit your job. If you don’t have any savings at all, it’s probably not a good idea to quit your job right away. I know that sounds annoying—you want to start doing what you love and making your own hours, right? But if you’re dead broke, it might be better to try to get some freelance gigs while you work on the side. 

That way, when you do quit your job, you’ll have some extra cash in the bank so that you don’t have to worry about rent and bills while you’re pursuing your dream.

Second, start with freelance gigs instead of trying to find a full-time job. That’s what I did! And it worked out great for me because there were more opportunities for me than there would have been otherwise.

Final Thoughts

Freelancing is challenging, to say the least. The freedom to do what you love doesn’t necessarily mean that life is easy as a freelancer. In this guide, we have looked at 27 dilemmas that freelancers find themselves facing, and provide tips for solving them. Freelancers are individuals who take responsibility for their own well-being. Keeping a positive attitude throughout it all helps. And when in doubt, always remember to be kind to yourself 🙂

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