Does this sound familiar to you? You really wanna give freelancing a go. You've read about people who are successful at it, but you're not overly confident in your skills. Heck, you're not even sure if you have any skills that you could use to even kick off your freelancing business. Oh well, maybe in 12 months you'll be able to give it another shot…

I get it. Starting something new, stepping out on your own and banking on yourself is scary. There's a lot of unknowns, particularly around how often you'll get paid, and how do you even start?

[Tweet “Starting something new, stepping out on your own and banking on yourself is scary”]

A few of my friends tell me that I can be a little glib sometimes. I can struggle with empathising when someone feels scared or unsure because my mentality is to just jump straight in and figure the rest out … but I know that doesn't work for everyone. So rather than give you some glib piece of advice, which would basically sound like:

“Suck it up, give it a try and if you don't succeed, try again or do something else!”

But I'm not going to give you that piece of advice…

A New Freelancer's Fears

Some of the biggest fears you might face as a newbie freelancer could include the following:

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  • Not being able to find clients that pay well
  • Being rejected for every job you apply for
  • Getting a horrible tax bill that you've no way of paying
  • Missing deadlines because you are juggling too much
  • Paying too much tax because business setup scares the bejeezes out of you
  • Being a complete failure and facing your friends and family


When should you use a pen name?Those are some pretty scary things right there. They are enough to stop anyone in their tracks. So I get it. I'm not saying that I've never felt scared about my freelancing business. There were times when I wondered how on earth we were going to pay the bills, particularly when my husband was laid off from his job…

But life happens, right. You have no control over anything other than the actions you take in your life. You can't control others around you and you certainly can't control your country's economy or anything else. Which is why it's far easier to forget about all that crap and focus on what you can do—take action in your own life.

Tips for Overcoming Freelancing Fear

Again, I definitely don't wanna sound glib, but sometimes you do have to feel the fear, embrace it and then meet it head on.

We often make our fears bigger than they actually are. Who needs to watch a scary movie when you can just tune into your internal chatter?

If you are completely paralysed by fear and unable to move forward and start your freelancing career or step up your freelancing business, follow these tips. I've used them at some point throughout my freelancing career and in other areas of my life.

Not all of them will work for you, but at least give them a try and then repeat those that work.

[Tweet “Who needs to watch a scary movie when you can just tune into your internal chatter?”]

Picture the worst case scenario…

This is my top go-to fear buster. Remember those scary movies? They've got nothing on what you can imagine! Every time I'm presented with a fear or I'm worried about the outcome of a situation, I simply picture what the worst possible scenario could be.

Once I ‘see' what the worst looks like, I'm able to deal with it. Part of the power of fear is the in unknown and unsureness it provides. Once you've pictured the worst, it can only get better from there, right?

I find that by doing this exercise, it also kicks my brain into problem-solving. Once I've seen the worst, I then start thinking of ways to fix it or get myself out of it. Try it and see if the same is true for you.

Upgrade your skills…

This is a fear I hear a lot. You might be thinking that your skill set isn't as good as another's, or that the skill you're looking at freelancing in is one you've only just started. Guess what? You can upgrade your skills. Don't let the fact that you might not be an expert in a particular skill hold you back.

There are plenty of options open to you to upgrade your skills. Here's a couple to get you started:

  1. Udemy
  2. Skillshare
  3. Guides

Don't use this excuse to stall your freelancing career. You can do something about it, so DO something!

Learn from others…

Look at what other successful freelancers are doing in your specific skill base and learn from them. Are they doing something different to land clients? How do they increase their rates? What about business setup and tax? Learn from others who are successful. Emulate what they are doing and if you get stuck, ask for help.

Research the issue…

If you're worried about how much tax you should be paying or how to setup your business the right way, then do some research. Again, fear grows largely from the unknown. So find out what you need to know and then take action.

Look for actionable advice…

This is another way of learning from others and then taking action. Look for simple and practice advice that you can implement into your business. The key being that you actually take action and follow through.

Write down the things you need help with or that you want to find out more about, and then each day, look for actionable advice. At the end of each week, start implementing what you've learned.

Create a file of job sites…

If one of your biggest fears is that you won't be able to find work, then start compiling a list of freelancing job sites right now. There are literally thousands available.

I have an Excel spreadsheet of the sites I use. I keep it updated so that I know that the sites listed are legitimate and working. To kick things off for you, here's my top 5 outsourcing sites and my top 5 freelancing job board sites:

Top 5 Outsourcing Sites

Number 1: Upwork (formerly oDesk)—I’m definitely biased when it comes to Upwork, but I have never (aside from the one time!) had any issues with clients that I’ve worked with here and 9 times out of 10, I have continued to work with most of the clients I’ve secured roles with on Upwork. It’s a great way to get started as a freelancer and provides a quick way to get yourself into money within 7 days.

Number 2: Elance—Elance is very similar to oDesk but tends to provide higher quality jobs but with this comes the additional layer of needing to prove yourself. It can be difficult initially to get started on Elance, but once you’ve got a good rating and have done a number of jobs, you’ll find getting good paying clients becomes a lot easier.

Number 3: GuruOne of the great things about Guru is the ability to set up five different freelancing profiles. This means that if you’re looking to diversify your skill base, you can create a profile specifically for that skill set. They also handle tax reporting so you don’t have to worry about sharing your tax details with them.

Number 4: Freelance SwitchYou’ll find a lot of classified jobs on this site, even though it is listed as an outsourcing site. It mainly caters to IT jobs, although you can find a few SEO, design and some writing jobs here. It will cost you to access the jobs, with a monthly fee of $7 to be able to bid on a job.

Number 5: FreelancerSimilar to the other sites, you sign up as a freelancer and can bid on jobs. They have some unique differences in that you can enter contests to win jobs as well as bidding on them. There are a lot of average jobs and clients on this site, so tread with caution.

Top 5 Freelancing Job Boards

Number 1: FlexJobsThis is the best freelancing job site, in my opinion. They basically aggregate freelancing jobs from all over the web, but they have real people who research those jobs and sort through them to only display the legitimate ones, including jobs for telecommuting, part-time and remote based roles. You’ll have to pay a monthly subscription fee of $14.95, but it’s well worth it in my opinion.

Number 2: TextBrokerIf you’re a writer, this is the best site to start with. One of the best things about this site is that they use Paypal and cover all fees when paying writers, so it’s unique in that respect. The quality is high and clients are looking for quality over quantity.

Number 3: 99DesignsAs a designer, this is your number one job market. You can showcase your work and accept 1-on-1 projects or design for a ‘contest.’ If you win a contest, then you get paid. It’s free for you to access and is a great way to build your portfolio.

Number 4: GetACoderIf you’re in the IT industry, then this site is just for you. If you’re looking to start your freelancing business on the side by  utilizing your IT skills, this site is for you. You have the option to pay for a monthly membership, or just pay a fee per project you accept, which could be ok while working part-time.

Number 5: FiverrI use this a lot in my freelancing business, but it is also one of the fastest ways to get started as a freelancer. It has a low barrier to entry and you control how often you work. Granted, you only actually receive $4 per gig you complete, but if you can complete 5-7 gigs an hour, that starts to add up. And then once you have a good reputation, you can add additional gigs to your existing gigs to increase your rate. It’s free to join.

The bottom line or my key takeaway for you when facing your fears is to take action. Don't give the fear any more power than it already has. Don't allow it to stop you from doing something you really wanna do.

Freelancing is one of the most rewarding choices you can make in your life. You just have to make the decision, bank on yourself and step out.

More Fear Busting Resources:

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Do you have a fear you just can't shake? Leave a comment below and I'll suggest ways to ‘fix' it!

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Lise Cartwright
Lise Cartwright

Founder of Hustle & Groove and your creative business strategist. If you want to get notified of new posts just like the ones you see here, then make sure you join the awesome H & G community — Join Now!

    2 replies to "The Ultimate Cheat Sheet for Mastering Freelancing Fears"

    • Virtual Helpmate

      Great advice Lise. I remember my greatest fear was lack of skills. It hindered me from taking the plunge to freelancing though later I managed to overcome it. I’m now a full time Virtual Assistant. I boast of 2 good years in this field.

      • Lise Cartwright

        Yes, starting out definitely causes fear of having a lack of skills and which skills to even focus on. Congratulations on being full time for 2 years, that’s awesome!

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