Dare again

Dare again
July 6, 2018 Janine Doggett
In Business

Dare and dare again

Going freelance is rewarding but tough. Here’s what I learned about DIY business from setting off for 1000 solo miles.



Going solo is scary

I’m a big fan of Brené Brown’s work around vulnerability. The research professor-turned courage advocate often talks about the idea that if you’re human, you most likely don’t want to be vulnerable. We’re taught that it’s weak, it’s bad, that it’s synonymous with failure. But to succeed as a freelancer, you must also fail, because you have to test stuff that might not work and, what’s more, no matter how great you are at what you do, no matter how much you care about it, not everyone’s going to like you. Sooner or later, you will get zero response from that pitch or, worse, you’ll get negative feedback. It’s in times like these, that the choice can feel tangible: sink into a safe place where you won’t get hurt again, or stand up and be vulnerable – again. Ugh.



Switching safety for freedom is worth it

When I left my full time job, I took away the safety of guaranteed money dropping into my account every month and in return gained freedom from that employee auto-compliance with the things that I fundamentally disagree with. You know, the stuff that makes you feel like you just took a Dyson to your soul.

I love my work and I love working hard; there is nothing that makes me happier of a working day than sinking into a flow. Bewitched by the task of writing to brief while the hours fly by, and waiting on the other side, a satisfied me and a happy customer. Freedom isn’t time or hard work related. It’s not freedom to nap, to watch Love Island at 3pm or to push off early on a Friday (although sometimes it’s definitely the last one). Freedom means making my own rules: working near an open window (if I’m offering a non-controversial example), or as far away from sexism and bullying as possible (if I’m offering an honest one).

Simplify the task

Choosing open windows and kindness – or whatever it is that you value – also means choosing grit; you can’t work under your own rules without vulnerability, can you? So, where does that leave us sensitive-types? Well, honestly, it sucks – a lot. But I believe you can be sensitive and robust at the same time, and that you don’t start out robust, you practise it, and when it gets tough, you keep practising. Here’s an example.

When I set out with a plan to ride my bike 1109 miles from Land’s End to John O’Groats on my own to face a long-held fear of physical isolation, I did so feeling exceptionally vulnerable. There were times during those three weeks of cycling that my POC shades steamed up so much from the tears that I couldn’t see where I was going, when my legs shook as they pedalled and when I ducked into a public loo to have a quick wee and a cry while praying that my bike would get stolen while I peed so that I could go home.

After a coffee and some food to mop the tears up and refuel, oh the endless food, I told myself that the answer was so very simple; that for right now, in this moment, all I need to do is keep pedalling. I wanted to reach my goal and, sometimes, boiling it down to the absolute baseline was the only way. There were many times that I wanted to quit, and acknowledging the excessive noise while focusing my attention on two simple words made the so-big-it-needs-flipping-jazz-hands plan so much easier to achieve: just pedal. Is my bike working? Yes. Do I care about getting to John O’Groats? Yes. Do I know the way? Yes. Okay then, just pedal.

As a freelancer facing the challenges of building a business, it’s no different. My bike is my skill-set, my goal is quality work for great clients, the route is my expertise. There will be hills, there will be punctures; damn it, there will be tears – I just have to keep pedalling.



Dare and dare again

If you’re a freelancer like me, and find it tough to get going, just pedal. Call another person, send another email – push another door. Absolutely learn and change what you’re doing, but don’t stop the doing. If you’re in a job that isn’t aligned with your values and you can create the opportunity to switch safety for freedom, I wholeheartedly believe you should do it. Dare greatly, and when it gets hard, dare again. It is the only way, and it’s worth it.


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