The five biggest challenges for female freelancers

Why the path to scaling isn’t so clear-cut for the female freelancers: The greatest challenges they face and the number one (not-so-secret) tool to tackle them head-on. 

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The five biggest challenges for female freelancers and the number one tool to tackle them

“I scaled my business to 6-figures in under a year”. 

If you haven’t heard this phrase from at least one Instagram account in the past few months, we’d be surprised. 

At Freelancing Gems we celebrate all kinds of business growth. Especially the kind that affords the entrepreneurs freedom, wealth, and abundance they crave. 

But we also acknowledge scaling the ladder to success isn’t as clear-cut for some – especially mums and young side hustlers. Their biggest barriers to success are the kind that wear away at their self-confidence and diminish their self-belief to culminate in one in five suffering from ‘imposter syndrome’. 

This is why now more than ever, collaboration over competition rings true. A phrase empowering us to support one another, lift each other up and break through challenges to write our own story of success. 

In this piece, we look at:

  • The five biggest challenges facing female freelancers in 2021
  • Which kinds of freelancers are struggling most
  • The #1 way to overcome these challenges as a freelancer

We’ll explore the current hurdles female freelancers must overcome in a world charged with both liberating empowerment and intense competition. We then uncover the number one way every freelancer can navigate it all, grow their business, and own their value.  


The five biggest challenges facing female freelancers in 2021

It’s not shocking to discover money, mindset, and making sales are among the biggest challenges for women in business to scale. But it’s not just our recent Women on the Rise survey that says so. Across the board, these are the five greatest struggles for female freelancers around Australia and the globe:

#1 Attracting clients

Despite relying on their networks for referrals, 12% of freelance women still struggle to organically attract leads and clients. Be it a competitive landscape, struggling industry, or tumultuous economy, we all know clients and sales make a business go round. Which means this challenge can make or break even the most established of side hustles and startups. 

#2 Lack of stability and direction

Business is a rollercoaster. Ebbing and flowing in the best of times, and volatile and fragile in the worst. Almost two in five female freelancers believe a coach or mentor to guide their journey would help them navigate the financial, strategic, and emotional unpredictability of their business. This proves lack of a guiding light is still holding women back from flourishing in the gig economy. 

#3 Inconsistent income

21% of freelancers claim a lack of steady wages makes day-to-day growth difficult. For many, mystery paychecks make scaling and investing in their business challenging. From applying for loans to hiring a team and building out internal infrastructure, freelancers are heavily impacted by the lack of financial consistency a move from the traditional 9-to-5 brings. 

#4 Fear of failure

We said it before, and we’ll say it again. Imposter syndrome continues to plague the majority of freelancers, with an additional 15% saying fear of failure is holding them back from scaling. Additionally, embracing their value often feeds into other challenges, like converting leads and generating consistent income by charging their worth. 

#5 Loneliness

Big bottom lines and glamorous ‘digital nomad’ lifestyle aside, the mental and social strain of life as their boss leaves female freelancers feeling lonelier than ever. Without the team support and accommodative culture of a traditional corporate, many feel isolated and subsequently crave connection and collaboration to help their business grow. 

While most female freelancers are not immune to these challenges, there are two key groups disproportionately affected. 

Which female freelancers struggle the most?

While even the most successful women in business have experienced these challenges, as we heard on our Women on the Rise IWD panel, mums and young freelancers often bear the brunt. 

Time-poor and responsibility-laden, freelance mums perform the ultimate juggle between their professional and personal lives. It culminates in unstable income, domestic support, and social connection being their biggest barriers to scaling.

Meanwhile, younger freelancers (under 34) say it isn’t inconsistent wages, but lack of direction, leads, and mentorship that are their most significant challenges. 

Be it lack of experience, time, or support, comparison, and competition, such challenges weigh heavily on these freelancers’ journeys. It often leads to comparison, with women seeing strengths in their competition but failing to acknowledge their own. 

Luckily, there’s one key way to overcome it all. 

The best way to succeed as a female freelancer

…is to get a fresh perspective. 

To connect with someone who sees your value. 

To celebrate with someone over the big struggles and even bigger wins.

To ideate with for new visions and goals. 

A mentor. A coach. A business bestie. 

Call them what you will, there is strength in the freelance sisterhood. 

Here’s why finding a business friend can help overcome any challenge: 

  • Broadens networks
  • Instills confidence
  • Provides an outside look into your business operations and goals
  • Boosts referrals
  • Increases variety of offerings (outsource and offer new services)
  • Shares resources, knowledge, and experience
  • Provides emotional support on the lonely days
  • Helps celebrate exciting accomplishments
  • Inspires to do bigger, better, and bolder
  • Gives you the advice to make tricky decisions
  • Connects you to additional support as needed
  • Is a sounding board for new ideas

And with so many benefits, how do you go about finding the right ‘biz bestie’ for you?

The best types of business mentors for female freelancers?

At Freelancing Gems, we believe there is strength in sisterhood, meaning the more mentors the better! 

Some ideas to start you off include the kind of mentor who:

  • Is from the same industry as you
  • Is from a different industry to you
  • Is older than you
  • Is younger than you
  • Could mentor you
  • You could mentor
  • Complements your service suite

Can you think of a mentor or business friend you already have that fits one or more of these criteria? If not, here are a few ways you can find them (or more of them)!

How to expand your freelance network to overcome challenges

Some great places to connect with a new biz bestie or mentor include:

Work with what you got, girl! Reach out to old colleagues, take the plunge with a quick DM to someone you admire on Instagram and join the Freelancing Gems Facebook Community

And perhaps the best way? Get paired with a business friend perfect for you by becoming a Freelancing Gems Ruby member! You’ll be connected to a fellow Gem through custom matching based on your industry, interests, goals, and stage in business. It’s a great way to collaborate, inspire and empower each other on your unique freelance journey!


Ladies, it’s time to ditch the imposter syndrome and find strength in sisterhood!

Let’s make a pact to combat challenges of lead generation, stability, self-doubt, income, and connection by championing collaboration over competition always. 

With 1 in 5 female freelancers held back by imposter syndrome, it’s time we made that number ‘zero’ by seeking out women who lift us up, inspire and support us. 

A great place to start is to join a community of women already championing their worth and connecting to grow and bloom in the gig economy. Become a Gem today!


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