Articles - 5th December 2019

What the Startup Mentality can teach you about being a freelancer

Words by Steff Green
Illustration by Will Francis

Before I quit the day job for the wildlife of a freelance author, I worked in the burgeoning tech startup scene in New Zealand. I loved my years in the startup and tech world – there’s a vibrant energy surrounding the people that’s hella inspiring to the creative soul. You have to muck-in and get things done, which means you’re frequently learning new skills on the fly with the freedom to test creative ideas as soon as you can make them live.

But there was a dark side, too – the long hours, the industry shake-ups, the sometimes toxic workplace culture. All jobs have their highs and lows, but the important thing is that you come away after your time having learned from your experience. Here’s what I learned from the startup world that I carried over into my freelance business.


Move fast and break things.

 This is the famous maxim coined by Facebook founder Mark Zuckerberg. In the startup world, shipping product is the most important thing. That product can’t sit on some engineers computer while they tinker with the code for five years, because someone else will get to market first. You can fix the inevitable bugs later – the important thing is to be always iterating and innovating.

I’ve taken this to heart in my business. I’ve found that it will take me the same amount of time and money to get a novel from 95% perfect to 100% perfect as it will be getting it from 0-95%. And the vast majority of readers won’t care about that final 5% – a few missed typos. Now I’m able to feed their desire for more stories at a faster rate, and my audience has grown because of it.

“Move fast and break things” also refers to being a leader in your industry. It means you don’t rest on your arse when things change around you – instead, be the change and adapt to new trends and new clients. 


If you need something done, you’re going to have to step up.

In the startup world there often aren’t enough people to tackle all the work that needs to be done. What this means is that you’ll adapt to new roles and learn on the fly. As a digital copywriter, I often found myself editing videos, manning customer support, and running webinars. If someone says to you, “Steff, can you do this thing?” you learn to say, “Sure. I’ll figure it out.” The sentence, “that’s not my job,” never leaves your lips.

This prepared me well for the life of a freelancer, where every aspect of the business needs to be managed by me. If I need a book cover designed or an ad campaign run, I have to do it myself or find someone to do it for me. I love learning and I developed a barometer for understanding my own strengths and weaknesses.


Work on a thicker skin.

In the startup world, new and crazy ideas aren’t just welcome, they’re actively sought. However, once you lay out your ideas, be prepared to have them eviscerated by everyone in the room. If your idea emerges triumphant and becomes product, it will then go out in the real world where customers and commentators will tear it to shreds.

I learned quickly that I couldn’t take this criticism personally. If people thought my ideas were crap, I wouldn’t be allowed into the room. I was there because I was good at what I did, and I had to believe in myself. But decisions have to be made quickly so it’s good for all sides of an idea to be examined before precious resources are devoted to it. 

Learning to separate myself as an artist from my work has helped me to handle the criticism I receive with grace and good humour. Whether it’s negative Amazon reviews or comments from beta readers, I know they’re not attacking me as a person. I’m also able to critically evaluate my own work and make strategic decisions while parking my emotions and passion.


Your idols aren’t infallible.

Everyone in the startup world worships some founder – whether it’s Sheryl Sandberg or Elon Musk or Mark Zuckerberg. They put these founders on a pedestal and often use them as a model for their own business decisions. The hero worship can feel a bit like blind veneration, especially when many founders have a dark side that isn’t openly discussed.

Instead of looking for validation and direction from an outside source, I use my own values as a compass to make my career decisions. I do look to other authors and ask for advice, but I always run that advice through my own moral filter to make sure it aligns with who I want to be as a person.


Don’t marry your business.

This was the biggest and most important lesson I carried away. At the start-ups where I worked, employees were actively rewarded for being “married to the company.” They’d work long hours, including taking work home with them and being in the office over weekends. Managers would notice this and praise their efforts at team meetings. Loyalty to the company and time spent on the clock seemed to be more highly valued than the productivity and utility of your contracted 40 hours.

Often, these expectations were out of alignment with the reality of the job. My manager would often message me at 8 PM about urgently proofing or editing some piece of writing. The project was never urgent. It could wait 12 hours until the following working day, where I would approach it with fresh eyes and do a better job.

For many employees, co-workers formed their core friendship group. For founders, this blurring of work and pleasure was even more pronounced. Too many of the founders I worked for barely saw their families and had little life outside of work. They poured all their energy and passion into making the business successful, and had nothing left for anyone else. The long hours and concept that “work = family” meant that personal dramas and petty feuds often played out in the office and impacted otherwise successful projects.

I knew this was exactly what I didn’t want to do. What is the point of having freedom as a freelancer if you use that freedom to shackle yourself to a desk?

This is the hardest lesson to implement for me, because like a founder I genuinely love what I do. I’m excited to get up and work every day. But I have to set boundaries for myself around my evenings and weekends – they are my hours to rest and play, to enjoy and be grateful for what I’ve built for myself. That rest and time outside my writing gives me fresh inspiration and drive to succeed.

Have you worked in the startup space, or do you have clients in this space? What have you learned from them?

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