Running a business is not for the faint of heart — and that’s true for a reason. Over the years I’ve learned many lessons running Studio DIY, and I’m still learning new ones every day. One of the most requested topics from readers is what it really takes to be self-employed, so here are 10 things I wish I had known when I started my business seven and a half years ago.
This post was created in partnership with TurboTax. They offer a product tailored for self-employed people, freelancers, and side-hustlers called TurboTax Self-Employed, and several of the lessons below relate to taxes — one of the most intimidating parts of starting a business.
1. Emails Are Everything: Social media followers are valuable, but you don’t own them. The two assets you truly control are your website and your email list. Email provides a direct line to your audience and often converts better than social posts. I didn’t prioritize building an email list early enough, and I’ve had to work hard to grow it since. My email list is a fraction of my Instagram following but drives the largest share of product sales. That focus would have saved time and effort if I’d started sooner.
2. Learn Tax Deductions from Day One: Self-employment taxes differ significantly from taxes for people with traditional full-time jobs. Early on I lost money by not understanding which expenses I could deduct. Having tools that help you identify industry-specific deductions is essential. TurboTax Self-Employed can help you find eligible deductions for your situation. If you want additional confidence, TurboTax Live Self-Employed lets you connect with a CPA via one-way video to answer questions, review and file your return, and provide personalized audit assessments.
3. Names Matter: A business name doesn’t literally have to be permanent, but changing it is risky and costly. It makes sense to start with a specific niche for focus, but avoid names that lock you into one narrow category if you plan to expand. My business name includes “DIY,” which hasn’t crippled the brand, but it does require more explanation whenever I branch into areas outside of DIY.
4. Don’t Put All Your Eggs in One Basket: It’s tempting to focus on the most lucrative part of your business, but overreliance on a single revenue stream is risky. Plan to diversify long-term and build short-term actions that move you toward multiple income sources.
5. Value Community Above All: Running a business can be isolating, so cultivate relationships with other business owners and nurture them beyond strictly business matters. Equally important is the community of customers and followers who support you — stay engaged with them, listen, and learn from their feedback.
6. Have a Receipt System: If you’re ever audited (rare, but possible), you’ll need proper documentation for every deductible expense. Don’t rely on shoe boxes or random piles of paper. Establish an organized system for saving receipts — digital if possible. We use QuickBooks Self-Employed to track expenses and capture receipts year-round, which removed a lot of daily anxiety and streamlined tax time. For many filers, TurboTax Self-Employed includes an offer that pairs with QuickBooks Self-Employed for integrated tracking and filing.
7. Manage Cash Flow Carefully: Income can be seasonal. When money flows in, plan and save for the leaner months. Keep variable expenses under control and build reserves so slow periods don’t disrupt operations.
8. Set Financial Goals and Break Them Down Monthly: Track income and expenses in detail and set clear booking goals for the year. I reviewed past earnings and expenses, set an annual booking target with my team, then divided that target by twelve. Each month we tracked bookings against the monthly goal on a simple spreadsheet and color-coded progress. This gave structure: when we hit the monthly goal early, we could be selective; when we lagged, it motivated extra effort. That approach helped us reach the year’s target early.
9. Embrace “Yes” and “No” Seasons: Early on you’ll be in a “yes” season, accepting many opportunities to grow. Later you may enter a “no” season, becoming more selective. When you want to pivot or expand again, a new “yes” season will return. Accept this ebb and flow — it’s part of business growth.
10. Bigger Isn’t Always Better: Don’t let business growth drive you toward a life you don’t want. It’s easy to pursue growth for its own sake, but keep personal goals in view. A smaller, well-run business that fits your lifestyle can be the right choice.
Photos by Jeff Mindell
What lessons have you learned that I missed? Share them below. If taxes make you anxious, consider TurboTax Live Self-Employed for access to a CPA who can answer questions and guide you through filing.
This post was created in partnership with TurboTax. All content and opinions are my own. Thank you for supporting the sponsors that help keep Studio DIY going.