Lessons from a first-time freelancer

Exactly 12 months ago I launched my little website and officially entered the world of freelancing. At the time it felt both scary and exhilarating to be setting out on my own and putting myself out there so openly, but I trusted my gut and held on tight for the ride, without really knowing where it would take me. Rather like an action research project.

So far it’s taken me to some interesting places, and I’ve learned a thing or two along the way.

I’ve worked with some amazing people on projects that I really believe in, and in ways that are completely new to me. I’ve been touched by the support, generosity and custom of people I have worked with previously, of friends, and by the trust that’s been put in me by those I have met in more recent times. Importantly, I’ve been liberated by the flexibility that comes with the freelance life — the kind of flexibility that allows me to say “See you at three” to my three daughters when they leave for school each morning.

I’ve also had days when I’ve wondered what the heck I was doing. I’ve been surprised by feelings of uncertainly and self-doubt, agreed to projects that didn’t feel quite right, and put too low a price on my work leading to unhelpful feelings of resentment. I’ve had days when maintaining focus is such an effort that things like reorganising the cupboards and removing the burnt-on specks of grime from the stainless steel cooktop suddenly become emergencies requiring my immediate attention.

So, getting back to those things I’ve learned along the way, here are five.

  1. Begin by being kind to yourself.

The decision to freelance generally coincides with a desire to do things differently. Take as much time as you need to think through the purpose of your work, who you want to work with and, importantly, how you want to work. Initiate some new routines and practices that help bring your goals into focus, and resist carrying over established habits that don’t serve these. Don’t be hard on yourself if you don’t feel like you’re making much progress or if things feel uncomfortable for a while. Some of the best insights can come to you while you’re off doing other things. It took a six-week family holiday to put a stop to my endless to-do lists edited at 3am and need for extreme structure. Above all, never lose sight of the reasons you decided to go out on your own. 

  1. Establish a group of trusted advisors.

These are the people who are, in a sense, ‘in it with you’ — not in the day-to-day, but in a way that supports your bigger picture. These are people who understand you and your goals, and who you can turn to for an honest viewpoint and sound advice when needed. They know the value of not always telling you what you want to hear. They are your biggest fans and your toughest critics. They may be people you have worked with in the past, people you know who also run their own businesses, or a member of your family. They can also come from places you might not expect. I have benefited greatly from the experience, counsel and care of someone I met through my daughters’ school, and while we have become friends over the years, she’s someone whose wisdom I value and judgement I trust.

  1. “Don’t be good at something you don’t want to do.”

There’s a character called Rodrick in Jeff Kinney’s Diary of a Wimpy Kid children’s book series, and this is one of his ‘Secrets to an Easy Life’. While Rodrick applies this rule to the chores his parents give him, I’ve found that saying no to work that you ultimately don’t want to do to be the most respectful approach all round. Take time to think through an opportunity, and to consider what forces are at play in making your decision. It’s easy to feel flattered by an opportunity that holds prestige, is financially lucrative, or has come to you from someone who you respect, value or admire, but these are not reasons to take it on. Signing up to work you don’t want to do attracts more of that kind of work, and takes you away from the work you really want to be doing. Rather, use it as an opportunity to recommend someone you know and trust who would be great for the job.

  1. Make space for ‘stretch’ projects.

Taking on projects that challenge or extend your skills in some way can be a great motivator for self-directed professional development, opening the way for new opportunities in the future. Building my own website from scratch was my first stretch project, the process of which gave me some helpful insights that I took into other website development projects I’ve managed over the past 12 months. Mastering new skills and exposing yourself to different ways of thinking is inherently motivating, and we are fortunate to live in an age where many of the tools and resources needed to do this are available online. Don’t be afraid to step into different spaces. Subscribe to newsletters from other industries or sectors, sign up to online tutorials on Skillshare or Lynda.com, participate in webinars, listen to podcasts, or watch TED videos that open your mind to new possibilities.

  1. Find simple ways to turn your day around.

Working on your own can be really lonely at times, especially if you’re used to a stimulating office environment where your days are punctuated by meetings and regular interactions with colleagues. On those days when you feel a bit stuck in your head and your Beats To Think To playlist is no longer doing the trick, unplug your laptop and take yourself to a café, call a friend who also works on their own and invite them to set up with you at your kitchen table, or schedule a 30-minute walk or gym class in your diary to give yourself a deadline. This is about being aware of how you’re feeling and having some simple strategies in place to help move you through the flat bits.


Thanks for this great article Vicki - it describes my world perfectly. You wonderful words have given me a sense of relief that it's not just me! The doubts and fears, the time needed to transition, the value in mentors and advisors - can't hank you enough for sharing. Just what I needed today.

Congratulations on your first year in business. This is a great reflection of what you have learnt and I can appreciate your lessons from my own journey. One of the things I loved the most in my first year or so, was the new connections I made. I learnt so much from those I invited into my business life, it has made my journey so worthwhile. 
Cheers to the future years. 

Thank you for your feedback @MarieOrtquist and @execva. I'm so pleased the points resonated with you. Being kind to myself and letting go of the perceived expectations of others - and the high ones I place on myself - has been perhaps my biggest learning. Everything became a lot more fun after I got over that, although there are still times when I'm self-critical in a way that's not helpful. I think this is only natural when we have such high visibility over the achievements of others through social media etc. Sam, I too have loved the people I have invited into my business life, and am in an almost constant state of amazement by how supportive and generous some people can be - particularly other women. Your comments are an example of this. I've loved being able to pass work on to people within my network when I don't have capacity, as having finite capacity is perhaps the biggest challenge of them all for the independent freelancer. Thank you again.


Thanks for the article Vicki - I began freelancing in addition to full-time work 8 months ago by accident rather than design, but now i am thinking about making the full transition. It will be a while away from a financial perspective, but you have highlighted for me the things I need to keep front and centre - taking work that I want to be doing that enhahnces my professioanl development and specilisation, and not just all and any work that comes my way. I have also loved the wonderful people I have met recently who have really supported me, even when I have no idea what I am actually doing! 

Great insights Vicki. 

Thank you for your feedback @northorbit and @Nadineingram. I think you're wise to maintain full-time work while freelancing on the side, @northorbit - while you can manage it. It gives you some time to experiment with the kind of work you want to focus on, and test some of your systems and processes without compromising your financial security. I also started out with no idea what I was actually doing, and I actually see this as a good thing. Freelancing gives you a blank sheet of paper to do things 100% your way, and working it all out is a part of the fun!  You will know when the time to transition is right. I found the process of writing my website - finding the words and pictures to externalise some of my thinking around what I had to offer - to be very helpful. It gave me the impetus to do the deeper thinking. Having said that, my little website is in need of a big update! Wishing you all the best for your bold and exciting move into the freelance life.

Great advice! Just wanted to add that in terms of support, you might like to look up The Freelance Collective, an Australian community of local freelance talent! We are all each other's wingman/woman! 

@NinaHendy, thank you for the info about The Freelance Collective. What a great resource!