Freelancing: 5 Lessons from 5 Months

This is the best thing that ever happened to you… eventually.

Ab Brightman
5 min readDec 12, 2018

Hi, my name is Ab Brightman, I’m 24 and I’m a freelance Trainer, Coach and Consultant for socially impactful organisations.

I turned freelance in the summer of 2018 and phew, what a ride! If you’re considering turning freelance, or just have an interest in social impact and lifestyle design, I’ve shared my 5 biggest lessons from the first 5 months of building a self-business below. I really had no idea what I was getting into.

1. Take A Break First

If you’re making the jump to freelancing straight from being an employee like I did, for the love of God take a break first. Moving on from a workplace, however well or not it ended, is a big life adjustment and a pretty tiring process. So before you jump into the fray of trying to set up your new tax situation, or hustle contacts, take a break! I did not do this — which resulted in being too tired to make the most sensible decisions. People and organisations who really want to work with you won’t disappear with a week off but you will be in a much better mindset to make the most of opportunities after a rest. A hard refresh goes a long way.

2. Don’t Set Money Goals, Set Learning Goals

The learning curve of turning freelance is huge. The money curve… not necessarily. Which is fine. It can be very easy to feel pressured into taking less than ideal work in order to hit your financial targets ASAP and prove to yourself that this thing can work out long-term. However, you’re not getting into freelancing to compromise right away — you’re getting into it to carve out a better lifestyle for yourself! And you won’t know the actual boundaries of this until you can let go of immediate money stress and start exploring.

I recommend going into it with 3–6 months of savings, assuming worst case you made absolutely nothing (unlikely), to live on the tightest budget possible (tips on how to do this and be happy here), but picking up a 1–2 days of work elsewhere to tide you over is definitely a smart option too. This will alleviate pressure, leaving you the energy to pursue the huge learning potential which lies ahead of you. Set goals for yourself not around how many deals you want to close that month but what you want to learn — perhaps that’s sharpening skills of your trade, or learning to negotiate and invoice, or simply grow your understanding of sales. Whatever it is you will be far more satisfied, and your positivity will attract the clients you deserve. Play the longer game.

3. Prepare to Feel Very Exposed

Imagine carrying a plastic bag full with food shopping. In one second the bottom of the bag rips open, and food is everywhere on the floor. What a mess. Except that when you first start freelancing, the bag is you and the food is everything you’re not great at.

Working in a team, even a small one, allows you to avoid confronting some of your less positive traits, and less strong skills. Perhaps this is task swapping with colleagues, pushing back deadlines and making excuses, or just not feeling a huge investment in the success of the organisation. However, as a freelancer if you don’t get the work done in the right time frame, if you can’t learn how to do it, if you handle a conversation with a client or supplier poorly, or if you stayed up too late and want a quiet morning — you can’t hide in the noise of anyone else’s work for even a day, and there are no frameworks to follow in order to do a good job. Even though this sounds pretty uncomfortable its really interesting to go through — its much harder to grow as an adult, and as someone trying to create social change, without taking full responsibility for your abilities and actions.

Get used to that hustling bedroom vibe.

4. The Reality Is, You Are In Control

It’s funny; a lot of the reason to become freelance is to get to ‘be your own boss’. However, it’s very easy to actually end up with 10 different bosses, all who respect your working hours and deadline flexibility way less than your actual previous boss. Whoops.

Saying yes is especially easy at the start when you’re almost kinda grateful for the opportunity.

The important thing to remember is that you are 100% in control of the work you want to do, and the working relationships you want to have —you have full power to ask for what you need, be direct about any changes you’d like and bring the energy you want to and know that being poorly received, or ‘losing’ the work is far less likely than it feels. After some initial rough experiences I took a couple of months to really think about this as it was very new to me, and doing this gave me so much confidence to handle myself much better in future.

5. Don’t Wait

If you’re wondering whether to turn self-employed but don’t yet think you have the right experience or enough contacts… don’t wait for that day to come. Don’t wait until you’re older, or more experienced, or in the right mood, or more stable or more connected.

If you’re not the most experienced player in the game then you can price it appropriately, and you can carve out the time to learn how to get better. You should always be learning. If you’re not that connected then you can focus on adding value to your current network, or go in cold. Many people have generated business this way and there’s no reason you can’t be that person either. But likewise — if you don’t get the income you need, as I say in point 2, treat the whole thing as an accelerated personal development programme. There’s no rule that says once you go freelance you can’t go back again either, so the sooner you do it the sooner you will always have an option to do it in life, whatever else you decide to fill it with. This is the best thing that ever happened to you… eventually.

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Got some of your own tips to share? Wanna grab coffee and chat about life? Hit me up in the comments or at