Freelancer roadblocks and how to overcome them

Here are the roadblocks that were stopping me from creating my dream career and how I undid them. By Emma Nolan.

If I added up all the hours I used to spend daydreaming about living out my best self-employed life I could have most probably definitely started my journey a little (read: a lot) earlier. Despite always taking small moves in the right direction, I’ve come to realise there was always something holding me back. Subtle cues that were not allowing me to fully devote myself to my craft. It is only now – hindsight is a beautiful thing isn’t it – that I can articulate these roadblocks and understand how I began to dismantle them.

It all started on one beautiful, sunny, booze-filled Saturday night (all the best stories do, of course). While spending a weekend away on the coast with friends, lots of laughs and a few too many margaritas, one of them asked me a simple question that in truth kind of derailed me. Are you ready for it? Drumroll please – “what are you actually waiting for?” I threw out a bunch of lousy excuses that seemed to revolve around money, stability, and waiting for the elusive ‘right’ time. I didn’t think too much of it at the time...

But then a funny thing happened, Monday morning came around and that question seemed to have stuck. I allowed myself to give the question some light, what am I actually waiting for. What is stopping me from creating this life I want so badly? I had motivation tenfold, but something was telling me I still wasn’t ready.

The good news is when we acknowledge these roadblocks we can begin to untie the mental blocks that are behind them. And the even better news, when we do, even by a little bit, we (and our businesses) will level up. Here’s how.

Roadblock 1: The fear of diving in the deep end

One of the best (and worst) characteristics of human beings is the ability to run countless simulations in our brains, thinking of every single possible negative outcome before we even take action, in business, this ultimately leaves you thinking ‘I’m just not ready’, ‘I don’t know X, Y, Z’. This is just resistance wrapped in excuses. The sad reality is, if you wait until you’re ‘ready’, you’ll never start. 

I know this is easier said than done, but to overcome this just have to bloody start. As the saying goes, when you’re thrown in the deep end, you have no choice but to learn how to swim. In this case, you download an invoicing system, you start networking and you read countless blogs on how the actual f*k taxes work. Plus, I’ll let you in on a little secret. Not many of us know much about how to run a business, but then one day, the invoicing doesn’t seem as scary and the client emails start feeling natural so go get ‘em tiger.

Roadblock 2:  Letting our limiting beliefs lead

When it comes to putting your work out in the world, usually, it’s ego and self-doubt that get in the way of kicking major goals. These negative thoughts are not unique to us. All business owners have probably experienced them in one form or the other. But when we focus on our own process, we aren’t as bothered or distracted by what others are doing.

Success comes from being your most authentic self, so look to your own work as a benchmark of progress and growth and feel confident in the work you are putting out there without worrying about others. As long as you know you’re doing the best you can and that is good enough, so go easy on yourself just do you, boo. 

Roadblock 3: Viewing our mistakes as failures

If there’s anything we can all agree on, progress is rarely linear. (we could make up a cute graphic like below for socials to talk about ‘viewing failures as positives’). The line to success is a lot messier, way more complicated and definitely not a straight line. Sadly, people often think one step back means they’ve gone all the way back to square one, which causes them to give up. This couldn’t be further from the truth.

Instead, you should celebrate these mistakes and turn them into lessons. Recognise that you’re going to mess up sometimes. But rather than declare yourself a dismal failure, use your energy to create a plan and get yourself back on track. It’s time to get comfortable in the uncomfortable and embrace every opportunity with a grain of salt. Without continual growth you become stagnant — so ask for that feedback, make some changes, improve your skill set, learn, grow, repeat.

Roadblock 4: Lacking a clear future vision

A vision is so much better than a goal; want to know why? Because it’s driven by passion. It’s an embodiment of everything you possibly hope to achieve and allows you to set yourself on the right trajectory for personal and business growth. It's unifying and inspiring and ultimately provides a clear focal point for future planning. Sadly, we rarely give ourselves time to sit with our thoughts and when we are forced to do so, we usually come up with some great ideas. 

Scheduling yourself some dedicated time, sans phone, sans people, sans anything and everything that isn’t coffee, a banger playlist or a blank word doc. If you’re someone like me who gets caught ‘hot-potatoing’ between tasks, then the Dream Bigger Workshop is for you. It’s the perfect opportunity to reflect, reimage and reset your business. It’s all about breaking out of conventional thinking and allowing ourselves to move into a realm of possibility, creating what we really want.

It’s time to say sayonara roadblocks, hello freedom

It is okay to have thoughts that hinder our attempt at running our own business or branching out into self-employment. We can take comfort in knowing that we are not the first ones to have such thoughts, and neither will we be the last. However, when we allow these things to dictate our lives it stops us from making moves forward. So count this as your official sign – pour yourself that big-ol cup of coffee and let’s kick all of those official limiting thoughts to the curb.


Written by Emma Nolan

A highly curious person by nature. Hates wearing shoes. Sometimes pens words on topics that spark passion, including the environment, self-development, and creative living. May or may not have an emotional attachment to her browser tabs. Connect @creativ.em.