5 Lessons Learnt From a New Freelancer

Thinking about taking the leap into full time self-employment? Come and find out the 5 lessons learnt from a new freelancer in the first three months since going it alone!

“Entrepreneurship is living a few years of your life like most people won’t so you can spend the rest of your life like most people can’t.” -Unknown

I was under no illusions back in December when I made the HUGE decision to walk away from my steady, reliable, full time job that this whole freelance thing was going to be tough. But did I really fully understand just how tough before I took the leap? Probably not!

Being a self-employed girl boss is all the rage at the moment, there’s been a massive influx of books, magazine articles, blog posts and podcasts all talking about the positives that come with having a freelance lifestyle and its something that a lot of millennial women now aspire to achieve.

Now I don’t want to burst the bubble or come across as a negative Nancy because of course there are lots of aspects of freelance life that I’m loving but I thought I’d talk about some of the realities that come from making the leap to working as a one woman band and subsequently some of the important lessons I’ve learnt over the past three months.

Thinking about taking the leap into full time self-employment? Come and find out the 5 lessons learnt from a new freelancer in the first three months since going it alone!

What I’m Wearing:

Jumpsuit* – JOY!

Leather Jacket – Topshop

Converse – ASOS

Bag – H&M


Get Clued up

This is a VERY important step that you want to make sure you have ticked off BEFORE you decide to take the all important the leap. Everything happened very quickly for me in terms of deciding to hand in my notice and dive head first into the world of full-time freelancing. I didn’t dedicate the time into putting the important processes in place that would cover my back if something were to go wrong. I’m talking drafting up a contract, getting professional indemnity insurance, putting payment terms in place etc etc. This oversight could have potentially left me in an extremely vulnerable position but it’s a mistake I’ve learnt from and I won’t be making again!

There are tonnes of resources out there when it comes to making sure that you’re running your freelance business all above board but here are just a few of my favourites:

Easy as VAT – For everything finance related

A Branch of Holly – For all things blogging and freelance related

Blogtacular podcast – To help answer some of those business bloggy questions

I also highly recommend finding some sort of mentor in the same industry who you can look up to and call upon for some advice here and there. I have a couple of people who I often reach out to if I need a little bit of guidance and it’s great to just get some reassurance from time to time.

Thinking about taking the leap into full time self-employment? Come and find out the 5 most important lessons I've learnt as a new freelancer.

Thinking about taking the leap into full time self-employment? Come and find out the 5 lessons learnt from a new freelancer in the first three months since going it alone!

Get Involved in the Local Freelance Community

Finding fellow freelancers and creatives to share my experiences with has been a key factor in my self-employment journey so far. Working from home can get real lonely, real quick so having like-minded people to bounce ideas off is essential. I’ve started going to a fortnightly meet up for local creatives based in Nottingham and it’s been a great excuse to get out of the house and speak to people face to face instead of from behind the comfort of a screen. It’s so comforting to hear that you’re not the only one battling those common freelance issues and there are other people in the same boat as you to moan about those annoying late payments and troublesome clients!

Networking is also my most effective approach to finding new work, there’s no better way to make a connection and prove that the services you provide can bring someone value than through a conversation IRL. It’s so easy to get bogged down in the day to day and make yourself believe that you’re too busy to go and have a chat with a room full of strangers but I can guarantee it’ll be worth your while!


Be Prepared For the Quiet Periods

When I decided to take the leap into full-time freelancing it was because I had a full roster of clients on board. My whole week was accounted for in terms of time which meant that the change from full time job to freelancing didn’t feel too daunting, after all it was basically just substituting one job for another right?

Wrong! Freelancing is no where near as secure as being employed by a company, clients have the freedom to choose on a month by month basis whether they still require your services. If you no longer fit into their business plan or they are forced to cut the budget on a certain month then it’s bye-bye contract and bye-bye money! This can be super difficult when you’re trying to work out your own income but one thing I’ve learnt is that there are always going to be quieter periods, it’s how you prepare for them that really counts!

To try and future-proof myself for any quiet periods ahead I’ve been attempting to get way smarter with how I handle my money and implementing a strategy that was shared with me by one of my mentors. I have begun putting any money that comes in throughout the month straight into my savings account and then come the end of the month paying myself a set ‘salary’ which has been carefully budgeted based around a (very intense looking) spreadsheet. This process is something that seems to work for me coming from the world of employment as it feels more structured to receive a ‘paycheck’ once of a month instead of in dribs and drabs dropping into my account randomly, it also helps me to set aside a portion of my income with the idea that it will be there should I need it on the quieter months.

Thinking about taking your freelancing full-time? Check out the 5 most important lessons I've learnt in the first 3 months of self-employment.

Thinking about taking the leap into full time self-employment? Come and find out the 5 lessons learnt from a new freelancer in the first three months since going it alone!

Grow a Thicker Skin

This is a lesson I unfortunately ended up having to learn very early on in my freelancing journey. When it comes to being your own boss you need to learn to stand up for yourself, no longer is there a HR department on hand to offer advice and guidance when a problem arises. You’re essentially on your own so this is when it’s essential to make sure that you’ve done the groundwork that I mentioned earlier in terms of putting in place contracts and terms and condition etc. They are your fallback when things get tough.

I’ve had a couple of setbacks over the past three months which are obviously inevitable when working for yourself and there’s definitely been days when I’ve wondered if it’s all really worth it. I’m not the toughest cookie in the jar so it’s been a real steep learning curve to get to grips with growing a thicker skin and not letting things get to me as much. At the end of the day I’m running a business so there’s days when I need to put on my best business woman head and be firm.

It’s something I’m working on…


Don’t succumb to Impostor Syndrome

One of the most common things that bloggers/freelancers tend to suffer from once they go full time is impostor syndrome. Some of the questions I find I ask myself on a daily basis are:

Why me? Do I really deserve this? Surely there’s tonnes of other people out there that are WAY better than me  at X, Y, Z?

This is such a dangerous mindset to get stuck in and is a cycle I’m 100% committed to breaking out of. The reason I’ve got to where I am today is through hard work and determination. Yes, some opportunities may have presented themselves to me as opposed to the other way around but this is all thanks to contacts I’ve made at various stages of my career and not through luck as some people will believe.

We all need to be a little kinder to ourselves and not beat ourselves up at any opportunity which is going to be my approach from here on out. Hard work = success and although I may still have a long way to go it’s going to be a damn sight harder with me doubting myself every step of the way so positivity here I come!


I’d LOVE to hear about your experiences if you’re a fellow freelancer or if you’re considering taking the leap too. What lessons have you learnt so far since going self-employed?


JOY were kind enough to let me choose an item from their women’s clothes range but as always all thoughts and opinions are my own. 


Photography by Creativetiff Media.  

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Author: Jessica

I’m Jess, a twenty-six year old self diagnosed Instagram and brunch addict. Whilst browsing Jess Who expect to find a hint of relatable personal style, Pinterest-worthy interiors, drool-worthy food and all of the latest happenings in Nottingham!