Starting as a freelancer: 11 lessons & reflections

Inspiration on how to start a business of one, finding the right projects to work on and designing he life you want.

Me during one of my first client calls

“What has been your journey into freelancing?” I often get this question, so I thought I write an article about my initial journey and the lessons I learned in those first years.

The lessons cover three main themes:

• Starting as a business of one;

• Choosing the right projects and;

• Designing the life you want.

Starting as a business of one

• Start with a “freelance prototype”. I ‘officially’ started freelancing in 2019. I worked four days a week at Idean (now frog) in London. Luckily, side hustles were seen positively, so I could try out being my own boss for 20% of the time. Initially, I only provided workshops or training on service design in the social innovation space for Italian organisations. This allowed me to test the waters in Italy. I knew I wanted to move back to that country at some point, and this was a great way to run a test and build my network. I spent 80% of my time on a ‘safe and stable’ job and 20% on a more ‘risky’ exploration. If freelancing didn’t work out, at least I would still have my job. As it turns out, though,  I was more successful than anticipated, so it felt ‘safe’ to take the leap. As my friend Gene says: “You applied the Barbell strategy to your career”. The “Barbell strategy” is actually an investment concept that argues that the best way to balance risk and reward is to go for a mix of extremely risky (10%) and extremely safe assets (90%). The result: You can’t lose a lot, but you can gain a lot.
  In my case, thanks to the pandemic making remote work the “new normal”, it didn’t matter where I lived. I could easily run online workshops for Italian businesses from the UK. I also started collaborating with my former boss, who was building a small consulting company in my home region. Work picked up until it wasn’t possible to do both jobs anymore. I quit my permanent position in London and moved to Verona.

• If you can, take a break between your permanent and freelance jobs. For a couple of months, I had two jobs and worked around 14 hours a day. It was a lot, especially during the lockdown. Looking back, I wonder how I managed to be so productive and focused. I can also see its impact on my relationships as well as my physical and mental health. If you take a plunge into freelancing and have the privilege to take a break, don’t think twice. Do it.

• Acknowledge that making the jump feels scary and prepare for it. Handing in my notice felt overwhelmingly frightening. For a couple of months, I felt a sort of existential anxiety. “Will I find enough work as a freelancer?” “Is this the right thing to do?” Visible proof of my fear and stress was reflected in my period tracker. The image below shows how my menstrual cycle changed during this time. I tried various mindfulness and relaxation practices, creating an emergency fund and other coping strategies. In the first months, I put most of my profits in a separate savings account called “When 💩 goes wrong”. This gave me peace of mind. I had a financial cushion that allowed me to survive without client work for more than six months. Now I also regularly detract a percentage of my revenues and put it in a separate savings pot for taxes, so I don’t have any unpleasant surprises from the tax office.

Screenshot of my period tracker, showing how my cycle length went up to 47 days after quitting my job in February 2021 and slowly went down to 28 days a few months later. The second screenshot shows my bank account and the different saving pots I created: Tax, Treats, and When s*t happens.

Choosing the right projects to work on

• Take the first year as an experiment. This was the best piece of advice that I was given (thank you, Andrea Fischer 💙). I was convinced I needed to have everything figured out before I started as a freelancer. My offer, my positioning, my website, etc. With this advice in mind, I decided to try different projects and see what I liked the most. I realised I enjoyed working on climate adaptation, how we adapt to the consequences, and how we reduce emissions. (Here, you can find a link that explains the difference between climate adaptation and mitigation). Another unexpected discovery was the possibility of remote work that the pandemic opened up. Instead of focusing solely on Italian clients, I could continue working with organisations across Europe.

I used Notion to quickly build a portfolio and showcase my work to potential clients instead of creating a fully flashed-out website.

• Be aware of the domino effect and choose your projects wisely. It might be tempting to take on the first project that comes your way, especially when you fear there is not much work out there for you. The reality is that every project is a learning opportunity. I started with workshops and still get called for facilitation and training. I can see how the knowledge I gained in Fintech and climate-related topics makes me a more attractive candidate to work in these fields. If you have the privilege to choose or to wait for the right project to come your way, do it.
  However, striking the right balance between experimenting and waiting for the right opportunity might be tricky. That is why defining your values can be such an essential first step. You can use them as the main criteria that can help you create your personal values-based scorecard to assess opportunities that come your way.
  There are different ways to define your values; here is one example from a workbook by Blended Sense.

• Trust your gut or your values when choosing your projects. Sounds basic, right? It’s not. In the beginning, I thought joining the small consultancy as a partner was what I wanted. I have dreamed of building my own business since I was 20, and this was the perfect chance. It turns out it wasn’t. I said ‘no’ to this opportunity when the press release was all ready to go. It was damn hard, but it was the right thing. Fast-forward one year, we still collaborate on specific projects. I’m sure it would not have taken such a positive turn if we had gone ahead as planned.
  Maybe this U-turn wouldn’t have been necessary if I had defined my core values earlier and given myself permission to dream big. When you keep questioning a decision and need confirmation from others, it signals that something is off. It’s good to stop for a moment and get quiet to listen to yourself. If you struggle with this, find someone you trust and who can help unpick your doubts.

• Transform your limitations and constraints into strengths. A few weeks ago, a fellow freelancer asked me, “How did you get such cool strategic projects?” It made me realise that it’s partly due to my weaknesses. There are many more jobs in Product Design than in Service Design. My scarcity mindset initially told me to become a Figma Wizard. Instead, I focused on what I was most passionate about. I invested in learning more about Business Design (By the way, I can highly recommend the d.MBA). As a result, I became a more strategic designer. I got asked to help create new value propositions and ventures. The lesson: invest in what you like, not what others like.

Designing the life you want

• Design the life you want and make it happen. Freelancing can be stressful, lonely, and anxiety-provoking. But it has been an empowering experience for me. When I worked in agencies, I was assigned to projects. Now, I choose the clients I want to work with. I can be in sunny Italy whilst working for organisations all over Europe. If you had told me a few years ago that this could be my life, I would have laughed out loud. Now, I allow myself to dream big and work hard to make it happen.

• “Your quality of life is determined by the quality of your relationships” — This is a quote from Esther Perel, and it wholeheartedly resonates for me. When I started freelancing, I was scared of feeling lonely and losing connections. Actually, the opposite happened. I was able to extend my network and invest in my relationships. Amongst other things, this allowed me to spend a month with my sister when she needed me. I also found communities that supported and empowered me in my journey as a freelancer, including IndeCollective, where I can grow alongside inspiring and ambitious independents, and Upfront, a group of women founded by Lauren Currie on a mission to change confidence for women.

• Work on your scarcity mindset (if you have one).  I grew up on a remote mountain farm. We had enough to live a good life, but I never experienced economic abundance. I got my first job when I was twelve, filling up shelves at the local supermarket. To self-finance my studies, I always needed to find ways to make ends meet. It made me a hustler and shaped my relationship with money and opportunities in life. Instead of taking risks, I naturally prefer the safer option. I fear there are not enough opportunities, money, work, etc.
  To overcome my limiting beliefs, I intentionally take action to practice abundance. Sharing knowledge generously, I donate part of my profits and say no to projects because I know there will be others more aligned with my values and goals.

• Protect your energy: it is your most precious asset. I love what I do so much that I often get lost in work. I used to spend hours in front of the computer to the detriment of my health and relationships. My caring friend Gene recently helped me with the following mental shift, which I simplified in this visual:

My pyramid of priorities: Focusing on movement and mindfulness to have the energy and spark ideas I can share. By sharing and connecting with others to give value, I can generate new collaborations that lead to projects and commitments. This, ultimately, leads to new possibilities.

Before, it was projects and commitments that formed the basis of my pyramid: I thought all I needed was to work hard. I would share my ideas and connect with a small group of people through mentoring and one-to-ones. Then, if I had any energy and time left, I would care for my body and mind. Not very sustainable in the long term, right?

Now I want to prioritise movement and mindfulness. It gives me energy, helps me build resilience, and sparks ideas. I can share those ideas with the broader world and connect with different people. The aim is to provide value to others. This value generates new projects and new collaborations. Ultimately, those lead to more possibilities and allow me to dream even bigger.

So, here you go: these are some of the key takeaways of my first years as a freelancer. Your journey might look different. Are there any practical learnings that I haven’t listed?

If you are on a journey to becoming independent you can shortcut some of the trial and error by joining IMMA’s Get Ready to Work for Yourself workshop and accelerate your personal and professional growth. 💙
I’ve packed it with everything I wish I had known as I considered and started my journey.