Over 2,000 mentors available, including leaders at Amazon, Airbnb, Netflix, and more. Check it out
Published

Taking the Plunge: My Personal Journey from Freelancer to Agency Owner

I discuss my personal journey from a freelancing professional to an agency owner, the advantages and the risks.
Harry O'Connor

Founder, multiple digital agencies

Becoming a freelancer

I remember clearly the day I walked out of my full-time job to become a freelancer. At the time, I believed that achieving independence and working without a boss was the ultimate goal. However, as a freelancer, I soon realised that my earnings were capped by the only resource I had - myself.

To earn more, I had to work increasingly longer hours, ultimately settling for a balance between a decent income and a manageable workload. As a freelance web designer, I quickly gained a reputation as one of the best in my city, which led to more work opportunities and higher prices. Despite this, my earnings still weren't fantastic, and payments from clients were often irregular and delayed.

Time to make a decision

And then something amazing happened. My wife told me that after years of trying, we were going to have a baby. Overjoyed but also concerned, I considered two options for supporting my growing family. Option one was to leverage my freelance experience to secure a better-paying, stable job. On paper, this seemed like the smart move. Alternatively, option two involved transitioning to an agency model, which was riskier but potentially more rewarding.

As you might have guessed, I chose the second option and have never looked back. The journey, however, was not without its challenges. It wasn’t easy, I had to abandon my previous notions about business and shift from being the doer to the thinker. I read books, spoke to other business owners, and eventually hired my own mentor - a fellow agency founder that built a successful business before selling it.

Working with my mentor

This is when things really started to come together. My mentor helped me navigate many of the pitfalls I was destined to face. I built my team up to around 10 staff and got a bigger office. We started to work with bigger and better clients and won awards for doing our best work. Even though he is no longer a mentor, I still keep in touch with him to this day, thankful for the advice he shared with me in those early days.

Over time I learned to charge more and understand my worth. As I write this, my agency charges 30x more than when I started out as a freelancer. I also learned that to run a successful and healthy business I needed to look at my agency as something separate from me and my ego. I had to be pragmatic and often have difficult conversations with clients and staff and learn to be ok with that. I had to push myself outside of my comfort zone.

I learned how to find new clients and how to approach them, how to write killer proposals and land better work. I learned how to hire and fire, automate much of my business, understand the financials and legalities of business and more. None of these things were taught to me in school or University, and none of the books or online courses seemed able to fully prepare me for the reality of running a business.

Work-life balance 

Over time, my perspective on business has evolved. To me, an agency or any business for that matter is no longer solely defined by the revenue generated, the size of the staff, or the extravagance of the office and car – all of which I have experienced in my journey. Instead, it's about retaining earnings, reclaiming time to engage in activities that bring joy, spending time with my family and achieving a healthy work-life balance.

With that in mind, I moved from my city in England to a large villa in the Algarve in Portugal, complete with sea views, a pool, a private school for my children and endless sunshine and happy days. I say this not to boast (although I am proud of my success) but rather to explain this would not have happened without taking the plunge in the first place. Had I gone back to regular employment I would be earning around 20% what I do now, and forever regretting what could have been.

Through my success, I was able to free up the time and income to do other things. I built a second agency, a property investment business, and a consultancy practice and used my spare time to mentor others earlier in their journey. I can spend time with my wife and children and be there for them when they need me, at the beach and skatepark instead of being bound to a desk, working for someone else and watching the clock.

I can't deny that my journey has been filled with difficulties and setbacks, similar to those faced by all business owners I've met. However, I wouldn't trade my experiences for anything. You only have one life, so why not make the most of it?

Managing risk

I remember that decision to build an agency seemed like a big one, a huge gamble. Bigger even than leaving employment to become a freelancer. But in hindsight, what is the worst that could have happened? I was already earning decent money as a freelancer, and I always had the option to go back to employment. The only real risk was the danger of not fulfilling my potential. I think one reason that so few people go out into the world and build a business is that throughout education we are conditioned to get a job. It doesn't stop there, during the early days of my agency numerous friends and family asked me when I was going to get a "proper" job. I don't blame them for not sharing my vision and gravitating to the safety and security of a regular job, but as I write this from Portugal, I wonder if any of them have changed their minds since.

Final thoughts

Getting a mentor was absolutely key to my success and why I’m proudly a top mentor here on Mentor Cruise. I love helping others navigate their own journey in the way I did, building a better life and business. If you are thinking about building or scaling your agency or small business and think you could learn from my 20+ years of experience, then let me know, I’ll be glad to help!

Find an expert mentor

Get the career advice you need to succeed. Find a mentor who can help you with your career goals, on the leading mentorship marketplace.