I became an entrepreneur by accident.

It all started after I gave birth to my second child. I decided to take on freelance writing gigs to earn extra cash and make ends meet while I stayed at home with the kids. I wasn’t planning to work full-time again, at least not until my children were all in school. Writing would be my side gig, or so I thought.

It didn’t take long for my part-time venture to balloon into a full-time job as the assignments — and checks — poured in. I wasn’t prepared for it. I wasn’t organized. And I vastly underestimated the growth potential of my “side” business. As a result, I was putting the brakes on my own financial success.

Every single day I’m learning new ways to improve as a businesswoman, but it wasn’t easy in the beginning. If I could go back in time, here are four mistakes I would avoid.


    I never planned to become a writing entrepreneur, but I wish I would have adopted that mindset anyway. By not treating my side gig like a business from the start, things got muddled quickly. For example, I had my freelance payments deposited into our primary checking account, which is the same account I drew from for business expenses.

    As you can imagine, this got messy as the business grew. I was receiving multiple deposits each month and my business expenses were all mixed up with family expenses. Whether you are just starting out, or are a few years into your business, take a few minutes to set up a business account. Separating business and personal finances is the first step toward an organized balance sheet.


    I figured my writing job would remain a small source of income, so I didn’t mind whipping out a calculator and crunching the financials on my own. After all, I was trying to make as much money as I could in a small amount of time, why would I pay someone else with my hard-earned cash? This logic prevented me from hiring professional accounting help for a very long time — mistake number two.

    As my business grew, my finances became increasingly complex. Since I wasn’t getting any professional help, I spent way too much time trying to make sense of my earnings and expenses in preparation for tax season. Don’t wait until you’re in over your head to hire accounting help. It’s a headache you can easily dodge, and it’ll free up more time to grow your business. Seriously, I’ve been amazed by how much I learn by spending an hour or two every month with a finance pro. My financial picture is clearer, and I often get great advice about next steps.


    I had only planned to be a freelancer until my second child stopped breast feeding. It was all about making ends meet until then. I soon stretched that deadline to the day my kids started school. And then the timeline continued to grow. Self-employment always seemed temporary in my mind, and because of this I never constructed a roadmap to retirement.

    Now, I’m finally thinking about self-employment for the long haul, which means I’m saving for retirement for the first time since I left my traditional job in 2014. Self-employed individuals are notorious for putting off retirement savings because they don’t have employer sponsored plans. Be different. Care for your future self with regular contributions to a retirement account.


    I underestimated myself. I never imagined the growth potential I was tapping into when I started all of this. Now, I’m at a point where I’m thinking about ways to scale my business for profitable expansion, and I’m completely overwhelmed.

    My trouble with growth is that my business wasn’t set up for growth. I never standardized the processes of pitching new clients, onboarding contract workers or handling an increased workload. I simply handled these things as they came. Nowadays, I’m developing a system to manage multiple daily tasks that come with a freelance business. I’m planning much farther ahead, rather than putting out fires as they flare.

    I’ve made a lot of mistakes in my first few years as a freelance writer. I’m taking note of my blunders, correcting my failures and putting in the work to set myself up for long-term success. If you’re planning to venture out on your own, you’ll make some errors along the way too. But here’s the thing: While I’ve tripped up a few times, I’ve also done a lot of things right. I make a point to celebrate my wins, and so should you.

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