A Freelance Writer Reflects on Five Years In

In early 2018, I left my corporate career in human resources to go on what I then called a sabbatical. Five years later, I’m a freelance writer, business coach, and writing mentor. The in-between is a journey I reflect on often, and I’m grateful to… A Freelance Writer Reflects on Five Years In as published on Women Who Money In early 2018, I left my corporate career in human resources to go on what I then called a sabbatical. Five years later, I’m a freelance writer, business coach, and writing mentor. The in-between is a journey I reflect on often, and I’m grateful to have the opportunity to share it with you. Why I Started Freelancing I started freelancing accidentally. During my sabbatical, I launched a blog that partially focused on personal finance. I made connections within the niche via social media and, after a while, wrote a guest post for a prominent website in the space.  When I got paid for my work, a lightbulb went off. If I could earn $50 writing, I could earn $500, $5,000, and more. So I immediately started looking for platforms I could contribute to regularly. My first steady client was Women Who Money! As a few dollars turned to thousands, I realized I had met the goal of my sabbatical: finding a location and schedule-independent way to earn a living. That way, I could fully show up for myself and those I loved. I could work around my life rather than live around my work. Want to know more about my backstory? Check out this Women’s Money Talk article. Benefits of Freelancing During the last half-decade, I’ve enjoyed many benefits from freelancing — some expected, some a surprise. Of course, I’ve loved:  Creating my own schedule, entirely in charge of where and when I work. Being able to scale my freelance business up or down based on the ebb and flow of my life. Choosing which clients to work with and which assignments to accept. But I’ve also deeply appreciated: Forging relationships with other freelancers and entrepreneurs (they are your friends, not competition!) Gaining confidence when it comes to asking for money. Getting pushed out of my comfort zone (time and again!). Being able to fully step away from my business for more than three months when my dad passed away in 2019. I knew from the get-go that freelancing would provide the freedom and flexibility I wanted. But I didn’t realize how much that would matter until my father got sick. Then, I got to put everything else in the world on hold to focus on him, my family, and my mental health after his death. Freelancing gave me the precious gift of time. I also couldn’t predict how much growth I would experience as a small business owner. I’ve met more people and gained more knowledge in the last five years than in the 30+ years before! Related: Should I Quit My Job to Freelance? [The Pros & Cons] Challenges of Freelancing Naturally, my journey hasn’t been all chai lattes and impromptu naps. Despite mostly enjoying the ride, I’ve also dealt with my fair share of challenges. There have been obvious issues, such as: Not having employer-sponsored benefits (namely health insurance and a retirement savings plan match) Not getting paid when I don’t work Having to navigate paying my self employment taxes (I recommend getting an accountant as soon as you start making real money.) Having to always hustle for new and better clients Budgeting with variable income (the feast or famine phenomenon is real!) But I’ve also experienced some unanticipated hiccups, like: Losing multiple clients in a short period Having potential clients express interest in working together and then ghosting me  Dealing with projects that didn’t play out as advertised Chasing payments for completed work (I thought I would need a lawyer to collect several thousand dollars from a client. Fortunately, it didn’t come to that.) My biggest takeaways from these challenges are continuously fostering connections in your network and getting all gig details ironed out in advance and documented in writing. That way, you can call upon your circle when you run into tough times, and there’s never