How Netflix’s ‘Girlboss’ Accurately Summed Up The Freelance Experience

In 2017, Netflix created and released ‘Girlboss‘ – a 13 part comedy series detailing the early days of Sophia Amoruso, the CEO and Founder of Nasty Gal, as she first creates her iconic eBay store. The show rattled through the life of a twenty-something Sophia, struggling to find her place in the world, before eventually stumbling into business as a vintage clothes seller online. It detailed the struggles of making a name for yourself in the virtual world, dealing with critics, the financial stumbling blocks and social pressures of being an independent business owner and was, honestly, a joyous throwback to early 2000’s culture.

But more importantly, it documented a journey that many freelancers will undertake as they both discover their passion and struggle to make it work as a full-time job. It explored the idea that talent isn’t enough to support you financially and that even the best of us will make mistakes and fall short of expectations sometimes. It connected with me, a newly graduated marketer at the time, on a level that inspired so much of my own freelance career and truly struck a chord with the digital freelance community.

So how exactly did Girlboss represent the freelance journey?

Passion vs Practicality

No one could argue that the character of Sophia was lacking in passion and determination for her business. An avid fashion icon, she took an inspired knowledge of clothing and transformed it into an income – something that many a freelancer can relate to. Many of us, at the start of our freelance journey, can get overwhelmed with excitement about a project that we completely forget to work out the practicalities of the freelance lifestyle and the demands it can put on our lives.

As Sophia valiantly battles stock demands, lack of storage and competitor feedback alongside her deteriorating physical health, as a freelancer we can’t help but relate. A passion project can take up so much space in our lives that we often put other responsibilities on the backburner. We can get so wound up in our future prospects that our personal relationships, our financial circumstances and our living spaces can be neglected in our absence.

Success Won’t Last Forever

One of the most important lessons Sophia learns throughout the series is that her fashion choices won’t work for everyone. After an initial spike in success in her online store, she mistakenly believes that her customers will blindly shop for every single item she lists online. They don’t, and there’s an iconic moment in the show where she growly furiously at the undersold dresses and tears them to the ground in frustration – truly demonstrating her own hatred for both the failed product and herself.

As freelancers, we will all experience highs and lows throughout our working careers. Whilst the few months of freelancing might feel incredibly busy and productive, there will come a point where the work simply dries up and you’re left with an empty inbox and clients that ghost you at the first opportunity. It’s not a personal critique, it’s simply the nature of the industry. But unlike Sophia, we don’t need to turn that frustration inwards or blame our products, services or website. The work will always return, even if we have to wait a little longer for it than normal.

Side Hustles on Side Hustles

There’s a certain stereotype about freelancers and the amount of money they can make in a single month. Honestly – it’s probably a lot less than you imagine. Once the tax has been paid and without the security of a consistent monthly paycheck, our finances can be a little rocky from time to time. So sometimes, freelancers can pick up side hustles or side jobs to help support themselves – much like Sophia does in Girlboss. She decides to work security on an art school campus to help fund herself whilst her main business takes off and reaps the rewards of health insurance, rent and more money to put towards office space and merchandise.

No matter where you are in your freelance journey, establishing a secondary source of income is nothing to be ashamed of – whether you pick up some freelancing writing jobs, become a barista at your favourite coffee shop or commit yourself to checking the IDs of several thousand art school students.

When It’s Good, It’s Great

Throughout the show, one of Sophia’s greatest achievements is being able to afford to drink Starbucks every single day. Using the money she’s earning from her eBay store, she gets to splash out on fancy coffee, walk down the street like a woman on a mission and enjoy the true ‘Girlboss’ lifestyle we all dream of having. And this feeling can also be found in freelancing.

When we’re on our way to an exciting meeting, when we send off an invoice for a significant payment, when we create something beautiful for a happy client – that feeling of achievement is like nothing else. You feel indestructible, and even more so because you did it all on your own. You’re not a team of people committing to this, you’re just one person, working their fingers to the bone to achieve your goals and you’re doing it in style. There is an element of glamour to the freelance lifestyle and we might as well enjoy it while we can.

Life Doesn’t Stop For Freelancing

Despite the upwards trajectory of Nasty Gal’s profits, Girlboss does a great job of showing the other elements of Sophia’s life that aren’t going as well – from her cheating boyfriend to her health problems, to her estranged relationship with her parents. Her business might be booming but her apartment is still small, she still has to work at a job she hates, she still has to have life-threatening surgery and she still feels cripplingly alone.

This is an important realisation for many freelancers – especially those who have just left their full-time jobs for the self-employment rollercoaster. Although your career might be flourishing, it’s important to try and keep a steady balance between your work-life and your home life, no matter how often they might cross over. Don’t give up on your friends if they don’t understand your choice to work from home, don’t let your hectic schedule stop you from taking care of yourself and don’t let the pressures of freelancing isolate you from the people you love.

Sometimes You Will Need Help

There comes a moment where every young freelancer will need some help and support in progressing their career. Whether you need some advice on a client contract, your yearly taxes, your legal support or your motivation, asking for help is nothing to be ashamed of. In Girlboss, as Sophia begins to earn more money than she knows what to do with, she has to go to a friend for help in truly understanding her business plan and her profit margins. He lays it all out for her in helpful and simple terms (on bar napkins) and gives her the push she needs to finally start taking her company seriously.

It is always better to ask for help than to get yourself into a tricky situation you don’t understand. Even if that means calling the HMRC hotline twenty times a day, bugging your mathematically inclined friends to teach you how to build a spreadsheet or paying for an accountant to manage your money for you, it’ll be worth it.

You Might Not Always Get The Right Support

One of the most significant relationships in Girlboss is the dynamic between Sophia and her father. Whilst she has so much passion and energy for Nasty Gal, he struggles to see it beyond a child’s lemonade stand at the bottom of the garden. He doesn’t understand the nature of her industry or the market she’s carved out for herself and this causes a lot of tension between the two characters.

In a similar vein, many people in your life might not understand exactly what goes into running a freelance business. They might not see the hours you put into it, they might not understand why you’d voluntarily give up paid holidays and they might be constantly waiting for you to crash and burn. It’s important to understand that this attitude comes from a lack of education and understanding, rather than malice and that you don’t need to have everything figured out before you announce your plans to your loved ones. But in the end, you will always be the best form of support for yourself, and no one can take that away from you.

Everything is DIY

A lot of what makes Girlboss such an appealing show to watch is the idea that one woman can achieve so much from having so little. It truly is a rags-to-riches story that explores every inch of the hard work she put into delivering for her customers. From setting up DIY clothing shoots in her apartment, to hand-delivering items, to managing her inventory, customer feedback, pricing and business plans all by herself – it’s a true testament to the strength and determination of Sophia’s character.

As a freelancer, you need to imitate the exact same strength and multi-tasking ability to set up your own business and career. You need to be a one-woman band of marketing, service provider, client manager, recruitment, cleaner, secretary and accountant, all rolled into one. You need to be able to promote yourself and your services, send off invoices, reply to emails, source new client work and run your workspace simultaneously – all whilst doing the actual work for your clients. Versatility is vital when starting out as a freelancer and you will pick it up over time, but it’s important to stay organised to help keep your one-person team as structured as possible.

As a TV show, Girlboss was not without its flaws and it was sadly cancelled after just one nostalgia-covered season. However, the lessons it instilled in its viewers about the nature of self-employment, hard work and the power of the grind were some of the most relatable and thought-provoking I’ve ever seen in a series.


Did you watch Girlboss when it aired? What did you think of it as a show? If you have any thoughts you’d like to share, or any recommendations for similar shows about self-employment, let me know by emailing [email protected].

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