How Freelancers Face The Inevitable Fear Of Failure

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Fear of failure is an inevitable human emotion. It doesn’t feel good, but it crops up more than we’d like.

The dreaded premonition of looking like a dork can make your cheeks burn, your energy droop and leave you hiding in the shadows.

This couldn’t be more true than for freelancers.

As a freelancer, you are the boss, therefore it is up to you to secure work, get the job done, plan for the future of the business, pay the bills and even support your family.

In fact, if you hate your work, that is your fault too. All failure lies squarely on your shoulders.

But believe this or not, failure can actually be a blessing.

In this article we are first going to look at some awesome freelancers and the role that failure has played in their monstrous successes – then we are going to send you packing with a ton of awesome tools that you can put to use to battle the fear of failure. Yes, we are going to show you just how freelancers face the inevitable fear of failure.

Spoiler alert: It’s kind of like drown-proofing, but less wet.

Let’s start with lingerie. Because, why not.

Sara Blakely


Sara Blakely, one of the youngest ever self-made billionaires attributes much of the success of her ‘Spanx’ business to her father. He asked his kids every evening what they had failed at during the course of the day – always encouraging them to keep trying. Failure was not something to fear in their household, so when Sara touted retailers with her chopped up pantyhose, no amount of rejection could keep her down. And women across the world are grateful as they can now have their cake and eat it too!

If you have an amazing idea like Sara but are unsure where to start with building your billion Dollar empire then start with our Starter Kit.

Click Here to Start your Freelance Journey Today: Learn about the 5 freelancing tasks that even beginners can have success with on Upwork.

You can see Sara’s positive philosophy for yourself in the following clip.

Elon Musk

From Spanx to SpaceX….. Elon Musk – widely recognised as an all round hero, engineer, inventor, explorer, over-achiever, who’s current project is to colonise Mars, is one guy who readily accepts that failure is a natural part of the journey to success.

“Well, I have tried to learn as much as possible from prior attempts,” says Musk. “If nothing else, we are committed to failing in a new way.”

Sure, Elon has cash in the bank, and no debtors on his doorstop, but his stakes are way higher than what we are probably facing on a daily basis. So the lesson to take here is that failure is going to come. The trick is to be prepared, and to try again, no matter what.

Elon Musk
Elon Musk

Colonel Sanders

We surely couldn’t write about overcoming fear of failure without mentioning the Colonel. After a life filled with hard knocks, he hit the road in his 60s with a delicious chicken recipe and nothing more. He spent 2 years living in his car, trying to sell the recipe to restaurants – receiving 1,009 rejections before finally ‘getting lucky’.

It is a good time to reframe that idea of ‘getting lucky’, because in reality we can see that he worked his butt off, when many would have walked away long before. At the age of 75, Colonel Sanders sold KFC for $2,000,000.


Michael Jordan

Okay, he’s not a freelancer, but he’s a brand right? Just take a look at this quote from the big man himself.

“I have missed more than 9,000 shots in my career. I have lost almost 300 games. On 26 occasions I have been entrusted to take the game winning shot, and I missed. I have failed over and over and over again in my life. And that is why I succeed.”

Gary Vaynerchuk

If you have yet to discover the energetic powerhouse that is ‘Gary Vee’ then make sure you are sitting down before you watch this following clip.

Gary runs VaynerMedia, and one of the world’s hottest digital agencies. In his own words, he is a prolific angel investor and venture capitalist, investing in companies like Facebook, Twitter, Tumblr, Uber, and Birchbox before eventually co-founding VaynerRSE, a $25M angel fund.

This video is a wake up call, be warned, he has no time for fear of failure, and whatever you do, don’t describe him as ‘an overnight success’. He just might show up on your doorstep.

That is just 5 examples of bad-ass people that have looked fear in the face, like we all do, but rather than shrink into their excuses they stepped it up and became humungous successes. We can all do that too.

Guess what, they probably still face fears constantly (okay not the Colonel). Fear doesn’t vanish, in fact as success grows, fear often does too. But we can learn to manage it, to live with it and to learn from it. That is what the second part of this article is all about.

What Scares A Freelancer?

We are all individuals for sure, and some of us are tougher cookies than others, but there are common themes of fear that emerge amongst most freelancers and wannabes. I am sure you will recognise a few of these.

  1. The thought of leaving a secure job, with regular guaranteed pay
  2. Turning down a client
  3. Saying no to an aspect of a project
  4. Rate negotiations
  5. Getting something wrong
  6. Baring too much of your soul (especially for writers)
  7. Looking like a fool in general

Fortunately the fear is in your head. Yes, you will most likely look like a fool sometimes, but you will make it through, despite what we have been told for most of our lives.

School taught us to strive to succeed, and that failure could lead to some pretty mean stuff (let’s not go into that here – too painful!) So as lazy, 21st century humans we have learned to err on the side of caution, and opt for comfort as much as possible.

So let us tell you the truth…..Comfort is the freelancer’s enemy, not failure!

How To Face Freelancing Fears

Stretch Ourselves

The opposite of comfort is vibrance! So break out of your rut and go for your dreams.

You can only get used to the fear of failure by getting used to it. Much like resistance training, we need to stretch ourselves, just until it is a bit more uncomfortable than we would like. Our fear muscle needs those tiny tears just like biceps, to ultimately grow stronger.

The best ways to do this are listed here.


Become active online and in person with networks in your industry. Making meaningful connections is the best way to see what everyone else is doing, and to hopefully dispel many of your fears. We are all hustlers, crushing life one day at a time. The freelancers in the communities that we are a part of are imperfect humans like all of us, but they are pretty awesome and always keen to offer up suggestions to help one another.

When networking in person, don’t sit in the corner nursing your cappuccino. Get up and talk to people, there are no stupid questions. Really, we have tried them all.

Asking For Critique

This is one of Elon Musk’s secrets to success; continually asking for honest, critical feedback. It is no good simply sending your manuscript to your best mates so that they can tell you how clever you are. That is how these dreadful singers end up auditioning for the X-Factor, not that we watch of course ;).

What you need is honest feedback that you can learn and grow from – and you can get this from your peers in mastermind communities, and on LinkedIn for example.

Asking For Help

Aside from critique, you can also reach out for help if you find yourself totally unsure of which way to turn next. Other freelancers are a valuable source of information and guidance, find yourself a mentor, and pay it back by offering support to others in need. Your peers are your unofficial office friends, and a superb network for future work if you invest time and energy into making connections. As a freelancer you don’t have to be isolated.

If there is nobody that you feel that you can turn to, you can also hire an expert to answer something specifically for you – and for a fee they will impart their amazing knowledge unto you.

Public Speaking

This is an advanced suggestion, but one of the fast track ways to join the heavy weight fearless ranks. Find yourself a public speaking engagement, where you can talk about your awesome business. You could even try your hand at creating a podcast or a Youtube video channel to get yourself out onto a public domain.

Taking Action

Regardless of how scared you feel, always try to take action. Take the first step, pick up the phone, send the proposal. It is almost never as bad as you anticipate that it will be.

Additionally, don’t wait to take action, if you arrive at your desk with a feeling of dread, deal with that first. Everything else will be a breeze afterwards.

Always Learning

Consider learning to be an ongoing process, you are your greatest asset, so invest. If you keep that mindset you will be acutely aware that you can’t know everything. Even if you have a ton of experience, something could come along tomorrow to make it all irrelevant. So stay flexible, know that you are not invincible and always seek opportunities to develop your knowledge.

Making Space For Failure

Don’t expect perfection. Give yourself loads of chances to fail, and accept that failure is proof that you are trying. Playing too safe is bad for business after all, some risks are necessary. The path to success is rarely a smooth gradual incline.

Getting Pumped

Follow in the footsteps of Sara Blakely and fill your idle time with confidence boosting words from motivational experts. She memorised Wayne Dyer’s ‘How to be a no-limit person’ and claims that it prepared her for business success. You can check it out here.

Personally, we love Og Mandino’s ‘The Greatest Salesman on Earth’ for freelancers. Scroll 3 in particular resonates with the fear of failure.

I will persist until I succeed.

I will never consider defeat and I will remove from my vocabulary such words and phrases as quit, cannot, unable, impossible, out of the question, improbable, failure, unworkable, hopeless and retreat; for they are the words of fools.

I will avoid despair but if this disease of the mind should infect me then I will work on in despair. I will toil and I will endure. I will ignore the obstacles at my feet and keep mine eyes on the goals above my head, for I know that where dry desert ends, green grass grows.

I will persist until I succeed.

So don’t speak those words of fools! The main takeaway today is to remember to embrace the fear of failure, it won’t ever vanish. All you have to do, is take action regardless. Experience is what you get when you didn’t get what you wanted, and sometimes, that is just as valuable.

How do you deal with fear? Or are you someone who doesn’t know the meaning of the word? If you are feeling overwhelmed by fear in your freelance business, please grab our 5 Lessons to Fast Track your success on Upwork below

Click Here to Start your Freelance Journey Today: Learn about the 5 freelancing tasks that even beginners can have success with on Upwork.

Either way, we would love your input, so go ahead and comment below.

I help talented Freelancers use Upwork to leverage explode their online careers, add a serious boost to their sales and develop their ideal dream lifestyle. All of the strategies and techniques that I teach to others are ones that I have used myself and things that I have learned from building my very own multiple six figure content marketing agency. Gingerbread Marketing.

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