How to Turn a Side Hustle into a Career

You don't need to quit your job tomorrow or have a five-year plan to start something.

I spent years placing people in high-paying, high-stress roles I would never have wanted for myself.

I was good at recruiting;

I made sure I understood my clients and presented them with candidates they could get excited about. I built relationships with job seekers who came back to me three, four, five years later because they trusted me. Recruiting taught me how to read people, how to sell without being pushy, and how to have uncomfortable conversations.

In 2013, looking for extra income, I started taking on copywriting and proofreading work on the side, website copy, blog posts, proofing reports for non-native English speakers. What I didn't expect was how quickly resume requests started coming in, and the more I thought about it, the more obvious it seemed. I had spent years on the recruiting side of the table. I knew exactly what made a resume land, so I started offering those services as a side gig.

The Fiverr gig I almost didn't bother with

My first instinct was to keep it professional. Build a website, post ads, let referrals do the work. A colleague mentioned Fiverr almost as an aside, and I dismissed it immediately. I associated it with five-dollar logo jobs and bulk article spinning, but I was wrong and it took me a while to admit it.

I set up a gig with low expectations, mostly out of curiosity and orders starting coming in from people I had no connection to, finding me through search on a platform I barely understood. They needed what I was offering: someone who knew how hiring actually worked, not just someone who could reformat a document.

Moving to Thailand

The early stages of starting a business can be unpredictable, and I was cautious about quitting my full-time agency role and not earning enough to survive. 

So I moved to Thailand. 

A practical decision to cut my cost of living while the business found its feet. If I could live on significantly less, the income I was already generating would stretch much further. It bought me time, and removed a lot of social pressure. I was working more consistently, taking on more orders, refining my process. The Fiverr gig that had started as a test became something I was genuinely investing in. The platform rewarded that consistency, and for the first time, the whole thing started to feel it could replace my full-time income at home.

Selling on Fiverr, and selling via ads.

I've made over 2 million dollars on Fiverr, but at the beginning, it was nerve-racking. Using a marketplace where strangers with no reason to be generous leave you public feedback means you have to be good at what you do; it's very exposing. 

My other income came from my own website via Google Ads, and later via LinkedIn, but these were never as consistent, and LinkedIn has always been full of people trying to guilt people into providing services for free.

How freelance headhunting became a second income stream

As my profile and reputation grew, the enquiries started coming in. Alongside individual candidates came companies. Businesses trying to hire internationally who found traditional recruitment agencies too slow or too disconnected from what they actually needed.

They wanted someone who understood both sides of a hire. Someone who could search quietly, across borders, with discretion. Someone who knew how to build trust and understood that bringing a senior person into a business is not the same thing as filling a vacancy.

What leaving employment actually felt like

There were months at the beginning when income was low, and I had to watch what I spent. I definitely had doubts, but leaving full-time employment is definitely the best decision I've made. Keeping costs low in those early years meant I could build without the kind of financial pressure that makes people take on the wrong clients or underprice themselves. It gave me room to be selective, and being selective, over time, is what builds a reputation worth having.

Where things stand now

Now, I live in rural Portugal and work with clients across multiple countries. Some days it's rewriting a CV for a Finance Director in London, others it's a resume for Lawyer in New York. It all started with a copywriting gig in 2013, a Fiverr listing I nearly didn't create, and a temporary move to Thailand.

If you have a skill that people keep asking you about informally, take that seriously; it's the market telling you something.