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3 Strategies to Break Through Freelancing Mental Barriers

Have you ever honestly considered what’s holding you back as a freelancer? Is it lack of time to invest in your business, or lack of self-confidence?

Is it fear of failure? Or the fear that you might actually succeed?

Stefanie Williams joins us today to share the three ways in which she’s managed to overcome the freelancing metal barriers that were holding her back from starting and growing her business.

Great advice, Stefanie!

Twenty years ago, I almost went to college for journalism. Fear stopped me in my tracks. Then, for far too many years, I wondered, “How does someone get into freelance writing?”

I was thrilled to find the answer in the course 30 Days or Less to Freelance Writing Success. Even though the course gave me specific steps to make it happen, months after I finished it, I had little to show for it.

I was writing for myself, and I was learning about being in business. But mostly, I was just consumed by thoughts of starting a freelance writing business; I wasn’t taking the actionable, income-producing steps necessary to actually having one.

You know, sort of important steps … such as pitching.

(Gina’s Tip: In mid-December, I came up with a pitching challenge with a visual twist. We already have some readers who’ve started to reap the rewards. Yup, they’re getting new clients.)

I had plenty of excuses for my lack of action, and lack of time was my number one. I always had a plan for a day in the future, when I would “just start.” I told myself, “When the school year ends and I’m off work for the summer … that’s it!

3-strategies-to-break-through-freelancing-mental-barriersTime to Face the Facts

June came and went. Mid-July, I was still just thinking about it.

Clearly lack of time wasn’t my only problem. It was time to deal with reality or proceed with a “real” full-time job for the school year.

Starting a freelance business someday, while spending all my hours obsessing about it, wasn’t going to cut it.

If you find yourself wanting a freelance business, but time is passing you by without results, then it’s time to figure out what’s holding you back.

To do that, I started asking myself two simple questions daily. The answers to the questions were a bitter pill to swallow. But “getting real” led to officially starting my business and (hurray!) a freelancing income for my family.

Two Questions That Can Transform Your Life or Business

These two questions can help you anytime a problem has you stuck in life, including with your freelancing business.

Ask yourself:

  • What’s your obstacle?

  • How are you going to overcome it?

Surprise; surprise! It turned out that I was the only obstacle, at least most of the time.

I was my own worst enemy. Here I was, pushing 40, and finally coming to terms with how often my own mindset had interfered with achieving results in life.

4 Freelancing Mental Barriers That Derail Productivity

Let me know if any of these sound familiar:

  • Perfectionism;
  • Anxiety;
  • Lack of confidence;
  • Fear of failure/fear of success.

When it comes to starting and growing a freelance business, these mental obstacles can stop you in your tracks. In a worst case scenario, they might even prevent you from even starting if you don’t identify them and conquer them up front.

When you begin freelancing, you will not have all the answers; but if you want results, you’ll have to take action anyway. You will hear from fellow freelancers: “Just start,” and “Pitch before you are ready.”

It’s the best freelancing advice you will ever take, but if you are prone to perfectionism, anxiety, lack of confidence or fear of failure/success, then you’ll likely have to dig deep to make it happen.

Here are three ways I overcame freelancing mental barriers and moved forward with my business:

1. Decide It’s Happening

Giving up is not an option.

Too simple, right?

Actually, it’s not. It’s everything.

Don’t decide, “I’m a starting a freelance business, but first I have to … (insert excuse) …”

Instead, decide, “This is happening. I am blasting through whatever obstacle is holding me back.”

The right mindset is the key to making progress.

There was no way I was waiting another minute. I had already let twenty years go by!

Decide that this is happening. NOW. Decide that today is the day things will change.

Instead of piling up excuses as to why your business hasn’t started yet, or hasn’t grown to its potential, start problem-solving. This is the turning point that will take you from someday to just starting. Success or lack of progress (not failure!) begins in the mind. The mind is where a plan forms and actionable steps begin.

It was true, lack of time was an issue to a certain extent, but I was using it as an excuse. However, once I decided this was happening, now, I was able to let go of the excuse and to start working on solving the problem.

I rearranged my schedule to allow for part-time freelancing. I opened a business bank account and set up a new PayPal for freelancing only. Now, I was officially in business, treating freelancing like a “real” job, with a set amount of minimum hours to work per week.

2. Change the Way You View Failure

The most successful people define failure differently. Failure is inevitable on the road to success. So learning from your mistakes turns your so-called “failures” into successes. Failure is the most effective way to learn because those are the lessons you will never forget.

There are many great quotes about failure. My personal favorite is:

“Fail harder. You cannot be successful without failure.”  (Robert Kiyosaki)

I came across the quote accidentally; the words “Fail harder” were on the back of a T-shirt I “acquired.” (Yes, I need my own wardrobe! Borrowing from my kids is a problem to address another day.)

Every time I wear the T-shirt, people question me: “Fail harder? What’s that supposed to mean?”

They are totally baffled by it, but it makes perfect sense to me. To me, it means you have to go for it with all you have, even if it means you are going to go down hard. (It’s a volleyball T-shirt).

Every day, I remind myself to “Fail harder.” It’s the prime way I get my perfectionism issues under control. I accept that I am going to make mistakes as I learn. I commit to learning from them.

Furthermore, I accept that I’m going to fail, and I attempt to FAIL HARDER today than yesterday. It seems counter-intuitive, but it WORKS.

If you’re prone to perfectionism, anxiety, lack of confidence, and/or the accompanying fear of failure or success, then these traits will likely resurface on a regular basis.

Keeping a quote like the one above front and center can be as important as your “Why.”

3. Embrace the Discomfort

That “gut-wrenching, I can’t believe I just did that, I think I am going to be sick, now I have to do what!?” feeling – it’s a good thing.

When you experience that feeling, acknowledge it for what it is: growth. You are stretching your capabilities. You are taking yourself, and your business, to the next level.

Another great quote to keep front and center is from Jon Acuff: “Be brave enough to be bad at something new.” Proceed in spite of any fear.

Seek out that uncomfortable feeling! Teach yourself to celebrate it because it means that progress is on its way. You can read Gina’s take on it in her post How Pushing Out of Your Comfort Zone Will Get Results.

I’ve been pursuing the feeling of discomfort in several areas of my freelancing business, which includes freelance writing and editing, piano teaching/accompaniment, and future plans for “passive” income.

Writing/editing: At first, sending out a pitch left me reeling. Then the discomfort came when I had to negotiate rates. At this point, completing and sending the work still gives me anxiety. The work never feels “good enough,” but I do my best work, commit to “failing harder,” and hit send.

Piano accompaniment: I’ve upped my playing from once every three months to twice a month. It terrifies me every single time. I do it anyway. Parts of it are getting easier. I’ve screwed it up pretty epically (at least, that’s how it feels, but I am learning what not to do each time I mess up).

(Gina’s Tip: I wholeheartedly believe in “doing it scared.” It’s what prompted me to accept and deliver my first public speaking gig.)

Passive income: I have plans to develop a passive income by the end of 2017. As part of promotion, I’m going to get in front of the camera. (Yikes!) I’m going to experiment with YouTube and Facebook Live.

If I wasn’t willing to embrace uncomfortable feelings, my business would have never started at all. Being willing to step out of your comfort zone is a necessary part of growth.

Don’t Let Another Second Pass You By

For twenty years of my adult life, I allowed mindset issues to prevent success. Don’t let that happen to you. Imagine the possibilities, identify your obstacles, make a plan (with a deadline) to overcome, and go for it, today!

Where could you be in five, ten, or twenty years if you “just start” today? Are you getting in your own way of success? How can you jump out of your own comfort zone today? Please share in the comments below.

Click Here to Get Gina’s 8 Tips to Start Your Freelance Career

Stefanie WilliamsStefanie Williams is a freelance writer with an educational background in communication sciences and disorders. She is a wife, mom to five boys and one rowdy princess, and an aspiring minimalist. You can read more by Stefanie on her blog, Streamlined Freelancer.













Gina Horkey

Gina Horkey


Gina Horkey is a married, millennial mama from Minnesota. Additionally, she’s the founder of Horkey HandBook and loves helping others find or become a kickass virtual assistant. Gina’s background includes making a living as a professional writer, an online business marketing consultant and a decade of experience in the financial services industry.

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