Bookkeeping for Solopreneurs: Where Most People Struggle (and What to Do Instead)

Kimberly Green | 2025-05-05

Solopreneurs wear every hat—CEO, sales, customer service... and usually, bookkeeper too. But just because you can DIY your books doesn’t mean it’s a vetted use of your time. This guide breaks down where solo founders get stuck with bookkeeping, the bare minimum you should be doing, and when it makes sense to hand it off. Common Struggles We See from Solopreneurs “The biggest issue we see? Waiting too long to hand it off. By the time they hire a bookkeeper, the books are a mess, tax season is a nightmare, or they’ve unknowingly been cash-poor for months.” — Kimi, Co-founder of Sam’s List Here are the most common struggles: Not setting up a separate business account Forgetting to reconcile monthly Categorizing everything as “miscellaneous” Falling behind and scrambling at tax time Spending hours trying to learn QuickBooks when they should be selling or building Your Bare Minimum Bookkeeping Checklist Task Frequency Tools or Notes Separate business finances Once (ASAP) Business checking + business credit Track income + expenses Weekly Wave, QuickBooks, Xero, Excel Categorize transactions Monthly Use automation, double-check Reconcile bank accounts Monthly Match bank feed to your books Save receipts & invoices Ongoing Keep digital records or appls like Dext Review P&L and cash flow Monthly At least glance at your numbers Prep for taxes Quarterly Track estimated tax payments 👉 Check out our full list of accountants and bookkeepers specialized in working with Solopreneurs on Sam's List! When to Stop DIY and Hire Help “Once you hit $250K+ in revenue—or you’re spending too much time tracking transactions—it’s time to bring in help.” — Kimi Signs it’s time to stop: You have multiple income streams or contractors You’re falling behind each month Your CPA needs to ‘clean up’ your books every tax season 👉 Browse Bookkeepers for Solopreneurs Bookkeeping Options for Solopreneurs DIY Software + support Outsourced bookkeeping ...based on business complexity and revenue stage. FAQ Can I do my own bookkeeping as a solopreneur? Absolutely, especially at the beginning. Just make sure you’re tracking income, expenses, and reconciling monthly. Do solopreneurs need bookkeeping? Yes. Even simple businesses need organized financial records—for taxes, planning, and peace of mind. What’s a vetted bookkeeping software for solopreneurs? QuickBooks, Wave, and Xero are solid picks. Bench adds human support if you’re ready to outsource...