5 Common Fears People Have About Freelancing and How to Overcome Them

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Hi, I'm Chris and I'm super glad you're here. 7 years ago I taught my self-web design and freelancing. Now, I do my best to teach others what I've learned so they don't have to struggle as much as I did.

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Want to know the one thing I’ve found holds most people back from getting started as a freelancer?

It’s not a lack of ability.

It’s not even a lack of opportunity.

Plain and simple, most people don’t start freelancing because they’re afraid.

Before they even try, their brain goes through all of these scenarios that freak them out and leave them paralyzed. And ultimately, what could have been an amazing business never gets off the ground because of fear.

I’m No Stranger to Freelancing Fear

I’m no stranger to freelancing fear.

I’ve had seasons where my days were riddled with literal panic attacks because of what I was facing as a freelancer and it was extra tough to just keep going and not give up altogether.

BUT, I’m still here despite the fact that my fear was trying to tell me it was all over and I should quit.

The good news is the fear you feel is almost always an overexaggerated reality.

In English, Chris. Okay…here’s a better way to say it.

The fears that you have of becoming a freelancer are not nearly as bad as ACTUALLY becoming a freelancer.

There’s a great acronym to help frame what fear actually is: False Evidence Appearing Real.

I know we’re getting cheesy but sometimes cheesy things are easier to remember.

Fear always makes our problems or challenges feel way bigger than they actually are.

Does that mean we should not worry about our fears?

Hell no.

There are some things you should be afraid of:

  • You should be afraid of walking out into traffic blindfolded
  • You should be afraid of walking in the jungles of Africa at night with raw lamb chops tied around your neck while you chant, “Here, kitty, kitty”

Fear can actually be a useful emotion that can keep you from a lot of pain and heartache.

But, I’ve got a hunch that fear isn’t really helping you as a freelancer. You’ve probably found yourself in the same situations I’ve been in where fear was keeping you back from something you know you could accomplish and you’re ready to move forward.

How to Overcome Fear as a Freelancer

The best way I’ve found to overcome fear as a freelancer is not to avoid it or dismiss it and pretend like it isn’t there.

The best way I’ve found to overcome fear is to pinpoint what the fear really is AND THEN speak some truth to it.

In other words, it’s time to sniff your fears out and show them who the boss is.

You’re the boss in case you were wondering. It’s you.

So, here are 5 common fears that people have about freelancing and how to overcome them.

1. How to Overcome the Fear of Not Knowing What to Do

In grade school, were you ever called on in class by your teacher and had no idea what the answer was? The dread you feel in that moment rivals any other type of fear you might experience in life.

It sucks not knowing what to do or say especially when the pressure is on you.

A lot of folks never get started as freelancers because they’re worried they don’t have enough skills to offer their clients.

People with this fear often find themselves in constant loops of taking courses, reading books, and doing everything they can to gain the knowledge to become a freelancer in their field, BUT THEY NEVER GET STARTED.

They’re trying to avoid that same grade school scenario that we all have literal nightmares of being called on without knowing what to say.

But, here’s the deal. You never feel like you come to a place that you know everything you need to know to do everything you need to do as a freelancer.

In other words, we’re all making it up as we go.

The people who become successful as freelancers are those that know how to move forward despite not knowing exactly what they’re doing.

I got the chance to interview Chris Do on my podcast and one thing he said has stuck with me in a profound way:

“The people who do well, almost always have this one trait. They have a heavy bias towards action.”

The idea that you’re going to learn everything you need to learn AND THEN go out and be a successful freelancer is a fairytale. In fact, you learn much more by going for it without having it all figured out.

There are some things you simply can’t learn without trying and failing.

So ignore the lie that you have to know everything before you get started.

Instead, embrace the fact that you don’t have to know everything to get started. You just have to be willing to keep going until you figure it out.

2. How to Overcome the Fear of Not Being Able to Get Clients

Next up in our lineup of the 5 most crippling concerns for freelancers is the fear of not being able to get clients.

I’ve been freelancing for almost 7 years now, and I struggle with this one to this day. I’m always worried that the last client I got will be the last client I’ll ever get.

Like maybe all the clients I got up until this point were pure luck.

And, therein lies the source of the fear.

For some reason, it’s easier to believe that people are able to get good, high-paying clients because they were just lucky. And, if luck is the deciding factor for freelancing success then what if your luck runs out?

Are you screwed?

But, here’s the good news, getting clients as a freelancer is not magic. It’s something that can be done over and over again through repeatable steps that anyone can do.

How do I know? Because a lot of people have been doing these same repeatable steps for years now and have been successful.

So, overcoming this fear is all about coming up with a game plan for finding and landing clients and then just getting out there and doing it.

Thankfully, you’ve got plenty of options as to how you find clients these days.

Here’s a shortlist:

  1. People you know
  2. Upwork
  3. Craigslist
  4. Social Media
  5. Linkedin
  6. Job Boards

And, that’s just a start! So, pick one of those and then start going for it.

Will it be awkward at first? Yes, most definitely. But, if you keep doing it long enough and you pay attention to what’s working and what’s not you’ll eventually find a few patterns that emerge.

Then you take those patterns and you start doing them over and over again and you refine what you’re doing even more until you become more and more successful.

Here’s the deal, if somethings not working, you don’t have to keep doing it.

I hate it when I see people post on social media about how they sent out 200 resumes for job applications and didn’t get any responses. After the 50th, you should have stopped and asked yourself what you were doing wrong and come up with a new game plan.

Don’t let this freelancing fear hold you back. Come up with a game plan for finding clients. Work that game plan until you see the success you want.

3. How to Overcome the Fear of Having Conflict with Clients

Conflict sucks.

And, this is coming from someone that isn’t all that conflict-averse. I rarely ever avoid a good argument if I feel like it’s worth it. But, I still don’t like conflict.

It’s not fun. And, a lot of people never start freelancing because they’re afraid they’ll one day face a demanding client who just can’t be pleased. OR, they’re worried they’ll have to keep hounding someone down to get paid.

Whatever the scenario it all centers on conflict. And, truthfully, conflict is unavoidable. But, there are plenty of things you can do to ease the pain of the conflict you will no likely face.

NO is your friend

Saying no isn’t wrong. In fact, it’s really important to know how to say no in life. A quick path to burnout and failure as a freelancer is saying yes to everything all the time.

So, if you dislike saying no you’ve got to realize that having boundaries and saying, “No” is actually a good thing and will lead to more success in the future.

You aren’t responsible for how people respond to what you do or say. You are only responsible for how YOU respond to what happens to you.

So, here’s a fun exercise. I’ll give you a few scenarios and then you can respond.

The client asks: “Can you give me a discount?”

Your response (say it with me): “No.”

See, wasn’t that fun? Let’s do it again.

The client asks: “Can you do one more round of revisions even though we’ve already reached the limit in our contract?”

Your response: “No.”

Take whatever scenario you’re afraid to say no in and do it yourself. It may seem silly but it helps.

Put Clients in the Business Relationship Category

Do you like personality tests? I don’t but I find myself doing them all the time. Go figure.

One test I’ve done a lot and almost always gotten the same results is the Meyers-Briggs Test. You can take the test yourself for free at 16personalities.com.

I’m an ENFP. Each of those letters stands for some trait of your personality. The third letter can either be an F or a T which stands for either Feeling or Thinking and it determines how we make decisions or cope with emotions.

Feelers make decisions and cope with emotions based on feelings and thinkers make decisions or cope with emotions based on thoughts or rationalization.

It’s important that in a client relationship you put everything into the “Thinking” category and don’t respond with emotion. So, when they say, “I don’t like this.” You don’t hear, “Your a horrible person and you shouldn’t be freelancing.” Because that’s not what they said.

For some people, this will come easy. BUT, if you’re a feeler like me, you’re going to have to work on it.

This is what I call a business relationship. It’s not about your worth or value as a person. It’s just a business interaction.

This makes it easier when conflict arises because you can realize that it’s not an attack on you personally it’s just a business issue that needs to be addressed.

4. How to Overcome the Fear of Asking for More Money

At a certain point, you’ll want to raise your rates as a freelancer. And, when that happens there’s always a bit of fear that goes along with it.

After all, there’s a lot of “what ifs.”

  • What if I can’t get clients at my new rate?
  • What if I’m not actually worth that much?

But, if you let this fear keep you from moving forward you’ll eventually get frustrated with the work you feel like you have to do at rates you hate working at. And, that only leads to poor quality deliverables for your clients which can cripple your business altogether.

So, for the sake of longevity, you will HAVE to overcome this fear eventually. Here are a few things you can do to get past it.

Increase your rates gradually

There’s no need to go from charging $20/hr to $200/hr. That’s a huge jump that doesn’t make any sense. BUT, what you can do is after every project, increase your rate by 10%.

You’ll eventually come to a place where you’ll find the majority if not all of your clients will say, “No.” And, that’s okay. You’ve just reached what I call your “price ceiling.” When you reach that ceiling you’ve got a couple of options.

  1. You can come down in price
  2. You can figure out a way to offer more value to your clients

You can do that through the services you give them OR simply by how you communicate your value.

Oftentimes, perceived value is way more about psychology than it is true value. That’s why some Nike shoes cost $10 to make and sell for $200.

But, you don’t need to go for the gusto at the get-go. Instead, take your time and increase your prices in small increments.

Prove Your Worth

I’m not on the “value-based” pricing bandwagon. A lot of that is self-esteem, psycho babel wrapped up in marketing jargon.

If you’re worth a certain price you should be able to prove it with more than, “That’s just what I feel like I’m worth.”

How do you prove it? Demand and ROI (return on investment).

If you have other clients that were willing to pay X amount of dollars for services rendered then that’s a good sign that what you got paid is what you’re actually worth. And, you can take that data and tell that to other clients who might press you on why you’re worth that.

That’s happened to me before. I had a potential client tell me that 4 other freelancers quoted half of what I was asking.

My response was that I had plenty of clients pay me what I was asking and sometimes more than what I quoted him. My price wasn’t what I felt like I was worth. It was what I knew I could get.

The other way to prove your worth is to show a client data for the return on their investment. In other words, show them that your last client was able to make X amount of dollars more after working with you.

So, if a client is going to pay you $1k but they’ll be able to make $10k more in their business as a result then it’s a good investment on their part.

The key is you need to make sure you keep track of that information as you help your clients.

5. How to Overcome the Fear of Not Making Enough Money

Finally, a lot of freelancers struggle with worrying they won’t be able to make the money they need to make from freelancing.

But, here’s the thing, you don’t need to quit your day job in order to start freelancing. In fact, my advice is that you shouldn’t unless you have to!

There’s this romantic idea in freelancing that you need to do something drastic and just go for it. But, the reality of most successful freelancers is a lot more boring.

A lot of freelancers keep a separate full-time job for years while they work to build up a freelance business on the side before they go all in. And, you can do the same.

Adam Grant’s book “Originals” talks about how “Stephen King worked as a teacher, janitor, and gas station attendant for seven years after writing his first story, only quitting a year after his first novel, Carrie, was published.”

STEPHEN FREAKING KING didn’t quit for a year after writing a best seller. So, why do you feel like you should put your two weeks in tomorrow?

A better idea is to try and build up a freelance side hustle that brings in at least half of what you make annually from your full-time job before you start entertaining the idea of going for it full-time.

That way when it’s time to quit there’s a lot less fear involved. And, the decision is more freeing than it is overwhelming.

Fear Never Goes Away

At the end of the day, fear never completely vanishes. Yes, you can reduce it. Yes, you can pinpoint the source of it and drown it out. BUT, you’ll eventually have to come to a place where you just put one foot in front of the other and go for it.

I love what Nelson Mandela said, “Courage is not the absence of fear, but the triumph over it. The brave man is not he who does not feel afraid, but he who conquers that fear.”

So, the next time you feel fear holding you back look it square in the face and do what you’re afraid of anyway.

I know you can make it past that fear and find success as a freelancer AND I’m cheering you on the whole way.

A woman with her hands on her face in fear to symbolize the fears freelancers face and how to get over them


Hi, I'm Chris and I'm super glad you're here. 7 years ago I taught my self-web design and freelancing. Now, I do my best to teach others what I've learned so they don't have to struggle as much as I did.

Every week, I write an article and release a podcast episode. Sign up if you want to get notified when that happens.



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