How To Survive Your First Year As A Freelancer


When Disneyland first opened its doors in 1955, nothing was ready

The night before the opening ceremony, workers were still hammering nails and painting the rides. In the sweltering Californian heat, pavements melted and the food ran short. The park was twice over its capacity, and there was a 7-mile tailback just to get in.   

Yet, Disneyland survived its first day.  And over 650 million people have visited since its opening. 

This survival story reminds me of the weeks before becoming a Freelancer (a freelance marketing strategist to be exact). I remember frenzied thoughts of: ‘Am I ready?’, ‘Do I have a business bank account?’, ‘Have I got enough money in the bank?’, ‘Where do I find work?’, ‘Do I need a website or just a LinkedIn page?’


Yet, one year later, I was a first-year survivor

I was frequently asked: ‘What’s it like going freelance?’. To save repeating myself, I wanted to get down on paper what the first year is really like. I wanted to share three things that got me through it:

  1. Skilling up everyday
  2. Working for a few agencies (but not too many)
  3. Always having 3 months’ salary in the bank

So, first things first… 


Why is skilling up every day so important? 


When you start out as a newbie, you realise that you're not the only one looking for work. There are more seasoned freelancers who are there to steal your lunch money. I won’t lie: this realisation scared the living sh*t out of me. I have a family and London-priced bills to pay, you know.


I made a specific commitment to ‘skill up’ five days a week

Looking back, I am glad that I committed to this. It accelerated my learning better than any training in a permanent job ever did.

And my first step to skilling up was also my best one: to find my own mentor, my very own Mr Miyagi. (You know Mr Miyagi? He’s the ace karate teacher from the Karate Kid films.) I needed a teacher that I could rely on to be there most of the time, someone to guide me, someone who was a seasoned pro.

I was adamant that I wanted someone who sees marketing differently

And I found one. In New Zealand. He’s called Sean D’Souza, who runs Psychotactics and I haven’t regretted spending a single New Zealand dollar with him since. (And no, he doesn’t look like Mr Miyagi).  

Since finding him, I spent £2k in 12 months (which is quite a financial commitment when you’re starting out on your own, I can tell you). I have studied in detail: content strategies, uniqueness, and consumer psychology.

Over the past two months, I spent one to two hours a day on a content writing course costing £900. And when you have work, a family and a commute, that’s also quite a big deal. 

However, I realised that I needed more than specific skills.


I needed breadth too

To get this breadth, I signed up to Audible and I rinsed though two audiobooks a month (it costs about £15 a month). Anything to do with consumer psychology, decision-making, habit-forming, content writing, storytelling, speech-making – I soaked it in through my ears.


Audible is like a supercharger to the brain

I like to spend 30-60 minutes most days listening to Audible walking to and from work. So, when I start a new contract, my brain is full of fresh perspectives for projects.

And, I still read marketing industry news and indulge in reading the ‘weird stuff’ too. But Audible is such a wonderful service. It pushes you from a steady stream of insight to a Niagara Falls of insight within a short period of time. Once you start Audible, it’s hard to stop. 

Yet, developing one’s skills aren’t enough to survive your first 12 months. I learnt that it’s also the number of businesses that you freelance for that’s important.


I liked working with three to five

Working for a handful of businesses is rewarding. Quality over quantity. It’s tempting to finish a contract and look for a new contract with as wide a range of businesses as possible. But it’s better to get to know a few businesses’ needs well over time. It feels good when you do.


The idea of gigging from one business to the next had limited appeal to me

I’m not one of those people who visits countries for a week and then moves to the next one, claiming "That’s it, I’ve done Japan. Now onto the next country”. It feels hollow. Finding meaning in my work and who I worked for was always a high priority.

This all sounds lovely. Like an episode of Little House On The Prairie, perhaps. Except, the rosiness runs out when you check your bank account.


Which brings me to my final survival tip...


Have three months’ salary in the bank – always!

One massive barrier to freelancing is the fear of not being able to pay the bills. It’s a scary prospect when you don’t have enough work lined up. My stomach churns daily at this thought, even at weekends.

I’ve found that having at least three months’ salary in the bank at all times is a huge mental relief. A healthy salary-cushion stops me assuming the foetal position and rocking myself to sleep.

To keep this buffer of cash untouched means that you must make new contacts – all the time. Even when you are working and don’t need the income.


My biggest mistake was not making enough contacts early enough

I relied on recruiters a lot at the start (for which I am lucky because they made my first year a prosperous one).

Yet when Christmas, Easter and summer holidays arrived, the phone didn’t ring so much. Unless I’d been smart and had a contract that took me into holiday periods, it could be a bit of a 'twitchy bum time'. 


And it’s not just holidays that make bottoms twitch

When businesses cut budgets, I still got interviews. But these interviews don’t turn into more than a pleasant chat. I’d notice my ‘conversion-to-sale’ rate dropping. It especially didn’t help if businesses have their own black book of freelancers too, who they know well and didn’t carry hefty recruiters’ fees.

This means that you must go out and hustle
Avoid the mistake of relying on recruiters only. It’s about keeping the top of the funnel full by any means possible. You’re your own New Business Director now.
Hustle, Hustle, Hustle. (A phrase I mutter like a loon under my breath most mornings.)

And this is what Disneyland did well before their opening day
Despite not being ready, they still had the top of their funnel full before Day One. They had done their hustling and got lines of hungry customers lining up in the sweltering heat. 

Yet hustling alone won’t do it: it's skills, relationships, and a cash buffer that kept my funnel (and bank account) healthy enough to survive. 
Otherwise, bottoms twitch.

Would I go back to a permanent job?
There’s an awful lot to say for being permanent. The lack of loneliness, the stable income. But I rather like the ups and downs of freelancing. And, those first 12 months gave me the time I need to work on my own business. It became quite addictive really.


Plus, I get to see my two-year-old daughter more
She’s growing faster than I imagined and I won't get those years back. I'm around for most bedtimes, in the mornings, on quiet days. It means that any worries about ‘how to survive’ are worth it. 

Thanks for reading. For now, over and out, tally ho and toodle pip  :o)

Simon | The Chief Brain



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