In a world where freedom is often sold as a marketing hook, Aditi Chakraborty has managed to create her own version of it and help others do the same. As a six-figure ghostwriter, founder of Side Hustle OS, and coach to more than 2,000 freelancers, she has built a thriving career for herself. I spoke with Aditi about what it really takes to build a sustainable freelance career, why authenticity is her strongest marketing tool, and how she helps burnt-out professionals build a life they never need a vacation from.
1. Freelancing gave you time, money, and peace, which is something most of us only dream about. How did you build systems that brought freedom instead of burnout?
It was a slow process of learning and evolving. My first few clients were difficult. I agreed to work with them at really low costs, and had to work much more than I was doing in my full-time job. Each new experience helped me put a system in place.
My first big step was informing clients of my fixed work timings. Then over time, I built systems for prices, offers, how to service and deliver to clients, the quality I expected from people I hired, and so on. Each of these systems is recorded as a document or a Loom video.
2. What do most people misunderstand about what it takes to succeed as a freelancer?
I have been freelancing for 12 years. I created my first e-commerce website in 2014 to sell ethnic wear for women. It takes at least a few years to become an established freelancer with consistent revenue. When people in the market know your name, they start reaching out to you as well.
So while one can make money even as a new freelancer, it takes time to build a solid reputation and business. As is the case with any industry. Freelancing is about systems, not luck.
3. Many 9-to-5 employees want to freelance, but fear of instability or failure keeps them stuck. What helped you overcome your fears?
Getting a bad rating! I have always been ambitious and worked hard at my job. I wanted to freelance for a while, but like you rightfully said, fear holds you back. So I slowly started building my side hustle, making money, and building up backup and confidence.
This helped me create a buffer to quit a difficult job if need be. When I saw my performance review in my full-time job, I realized it did not reflect the effort I put in. That gave the final push to take up freelancing full-time.
4. Your businesses, Side Hustle OS and Brown Beagle Design, are built around authenticity. How do you stay true to yourself, especially when the Internet tends to reward polish over honesty?
By focusing on the purpose around which I am building these businesses. I am building Brown Beagle Design to help leaders tell their stories and Side Hustle OS to help women achieve financial freedom. Keeping this in mind helps me stay on track.
With consistency, self-belief, and the right systems in place, you too can build a career that works for you. If you are ready to quit your 9–5 job or just set up a second income stream, join Aditi’s Side Hustle OS Community today.
