Introduction

Starting my freelance career marked a pivotal turning point. After leaving full-time work, I sought a flexible path. I wanted something that matched my skills and let me travel while I developed Project 50 on the side. I wanted to find energising work with interesting people in new industries.

This was my first time searching for freelance work as my main source of income, so I knew this project could be a challenge!

Project Motivations

Every decision we make has a trade-off in some way. Work is no different.

When deciding on your set-up, I always advise clients to look at their wider life goals and where they want to be spending their time, both in and out of work.

Applying this advice to myself, I realised I was in a life phase that prioritised health and flexibility.

I still wanted to deliver high-quality work without chasing a corporate ladder. Freelance consulting felt like the best fit for those goals and my risk tolerance.

What I was looking for:

• Find energising work: When work truly energises you, you show up more fully in all areas of life. After some restorative time off from my previous job, I reflected deeply on where I found my energy and how I wanted to sustain it going forward.

• Psychological stability: Always a saver, I could have taken more time off financially. Yet I missed the routine and structure of work, plus the sense of contributing to a greater purpose. With new intentions, boundaries, and a clear place for work in my identity, I felt ready and actively wanted to work again.

• Explore a new industry: After years in startups, I wanted to see how big companies work. I also wanted to know what makes a startup appealing to investors. I knew startups were my long-term fit, as I love their fast-paced nature and growth opportunities, but I wanted to know what “good” at scale looked like.

• Set up a business: A sole trader is the simplest structure. It allowed me to test if running my own (albeit one-person) business matched my expectations and justified the trade-offs. I wanted to validate my assumptions about being self-employed.

Preparation & Research

In preparation for starting the job hunt again, the first thing I did was take stock. What were my biggest assets that I could bring to my own job hunt? For me, my top five were:

• My network: Having run an online community platform for three years, helping hundreds to change careers, I had vast knowledge of industries, sectors, and contacts to explore work styles.
  
  

• One-on-one connections: I see myself as a digital introvert. I avoid mass social media posts but focus on nurturing quiet, meaningful interactions with my network. This proved vital for my job hunt.
  
  

• Creativity: Tailoring outside-the-box applications is something I love. As a career mentor, this helps clients stand out and signal genuine interest.
  
  

• Curiosity: I sought roles that allowed me to learn and included a selfish growth goal alongside getting paid. This distinguished exciting, challenging jobs from those that wouldn’t stretch me.
  
  

• Tenacity: Job searches rely on numbers alongside quality. Prioritising time, job boards, and steady applications was second nature.

Knowing how to work with yourself saves time and energy. A large component of understanding your next steps is understanding what you want from work and what you can bring (more on that here).

I then started researching. I reached out to network contacts at admired companies and interesting roles. I checked job platforms like Escape the City (mission-driven companies) and Otta (10 curated job ads weekly to cut overwhelm).

Alongside this, I told friends, family, and contacts I was job hunting, describing the work type and people I wanted to be around. Even without exact roles in mind, this sparked opportunities from my existing network.

What happened next

I found my first true freelance role via LinkedIn. Two people I had met through my last company were looking for an events coordinator for the venture capital firm they worked for in London for an upcoming event, with the potential to extend.

It fit my goals of working with people I admired and in a company I could learn from. For me, understanding VC and getting exposure to cybersecurity, defence, and technology experts and leaders across startups and FTSE100 companies was a huge draw and an area I was interested in.

Knowing both of the hiring managers was a huge advantage and allowed me to negotiate my salary and working terms, as they had first-hand experience of what I was like to work with. In addition, the event was coming up soon, so they needed someone who could hit the ground running.

Since I started freelancing, the scope of my role has grown to help with other marketing and digital projects, which has made me feel part of the wider team.

Overcoming Imposter Syndrome and Gaining Confidence
Starting fresh as an external freelancer brought anxiety and unknowns. Handling a major launch event was daunting without full knowledge of previous setups. Support from an internal friend and a successful event gave me confidence in my value, skill set, and communications.

Expanding Freelance Work and Building Stability
Over two years, I shifted from hourly rates to packaged contracts, gained client referrals, and found other freelance opportunities within GALLOS’s network. This financial stability allowed me to pursue business ventures, charitable projects, travelling, and my Project 50 initiatives in a sustainable manner. I couldn't be happier.

Skills & Lessons Learned

• Mastering client communication and setting clear contract boundaries

• Negotiating prices and understanding value beyond cost

• Effective time management through defining my flexible working hours

• Overcoming discomfort around invoicing and money discussions

• Balancing client expectations and delivering quality results

• Gaining business financial literacy and separating freelance and entrepreneurial roles

• Leveraging mentorship and professional communities for growth

Personal Reflection & Next Steps

Freelancing completely shifted how I think about work. It’s boosted my confidence, sharpened my business instincts, and helped me find a better balance between independence and collaboration. It’s opened some brilliant doors too and, maybe most importantly, reminded me how much I love building things from the ground up, especially as part of a team.

Next, I plan to keep freelancing in a sustainable way while exploring new and exciting projects alongside it. I want to keep supporting people who are starting something new or changing careers, through my work, volunteering, writing, and mentoring. At the same time, I’ll keep developing my digital skills and broadening my experience by learning from different teams and people along the way.