The Blog

    Less admin. More clients.

    Bookkeeping

    Why self-employed people struggle with financial management software

    Most financial management software is built for consumers or businesses with employees. Self-employed people sit in between, which is why the tools often feel too basic or too complex.

    The Sumly Team
    Bookkeeping

    Best self-employed finance apps for 2026

    A straight comparison of the best financial management apps for self-employed people in 2026, including Sumly, Wave, FreshBooks, QuickBooks, and Keeper, with where each one actually wins.

    The Sumly Team
    Deductions

    Myth-buster: does writing something off mean it's free?

    Writing something off does not make it free. A deduction lowers your taxable income and saves you a percentage of the cost, not the full amount, which is why tracking every legitimate business expense still matters.

    The Sumly Team
    Going Independent

    From side hustle to full-time: how to go independent and stay organized from day one

    Going from a side hustle to full-time independent work comes down to three things: building enough runway, lining up clients and coverage, and setting up organized systems from day one.

    The Sumly Team
    Bookkeeping

    Why your QuickBooks numbers are wrong: 3 silent errors that cost self-employed people

    When your bookkeeping totals look complete but still feel off, three silent errors are usually the reason: dropped transactions, duplicate payments, and buried deductions.

    The Sumly Team
    Bookkeeping

    How to avoid a surprise tax bill when you're self-employed

    Avoid a surprise tax bill by tracking all your income and deductions in one place, so you can see what you owe before the quarter closes instead of after the year ends.

    The Sumly Team
    Bookkeeping

    QuickBooks alternatives for freelancers: what to use instead

    QuickBooks was built for businesses with employees, inventory, and payroll. For 1099 freelancers, a tool built for self-employed income is usually a cleaner fit.

    The Sumly Team
    Going Independent

    When your freelance business and personal money live in the same place

    Mixing freelance income and personal spending in one account makes 1099 taxes harder than they need to be. Here is why separation matters and how the right expense-tracking system can turn bookkeeping back into background noise.

    The Sumly Team
    Bookkeeping

    Taxes and bookkeeping for fractional CFOs and fractional executives

    As a fractional CFO or fractional executive, you are self-employed in the eyes of the IRS, which means you owe income tax plus the 15.3 percent self-employment tax on your net earnings.

    The Sumly Team
    Bookkeeping

    Do freelancers need a bookkeeper, or just a CPA at tax time?

    Freelancers need both functions, but not necessarily two separate hires. A bookkeeper keeps your income and expenses accurate throughout the year. A CPA or tax professional files your return and handles tax strategy.

    The Sumly Team
    Bookkeeping

    Bookkeeping for independent consultants: the admin-light system that works

    The simplest bookkeeping system for an independent consultant is three habits: one separate business account, categorize expenses as they happen, and set aside a fixed tax percentage from every client payment. Here is how to stay organized without spending your evenings on admin.

    The Sumly Team
    Going Independent

    LLC vs. S-Corp: Which one actually saves you money?

    An LLC and an S-Corp are not the same kind of thing. An LLC is a legal business structure; an S-corp is a tax election that can reduce self-employment tax once net profit is high enough.

    The Sumly Team
    Bookkeeping

    How to manage your 1099 finances (without it becoming a second job)

    Independent income gets scattered across Stripe, PayPal, Venmo, and direct deposits. Here is a practical way to bring the money side of your 1099 business into one place so the year adds up on its own.

    The Sumly Team
    Deductions

    Mileage deduction for the self-employed: how to track it the right way

    Self-employed people can deduct business driving using the 2026 IRS standard mileage rate of 72.5 cents per mile, or by tracking actual vehicle costs. Either way, the log is the deduction.

    The Sumly Team
    Deductions

    Taxes for creatives and content creators: deductions and quarterly basics

    If you make money from content, you owe tax on it whether or not a platform sends you a form. You can deduct the gear, software, and workspace you use to create, and once your creative income is steady you will likely owe quarterly estimated taxes.

    The Sumly Team
    Bookkeeping

    Bookkeeping and taxes for independent healthcare practitioners

    If you run a private practice, the right bookkeeping system keeps your business finances clean and separate, captures the deductions specific to clinical work, and connects to your accounts through secure, read-only access so nothing can be moved or touched.

    The Sumly Team
    Going Independent

    CPA vs tax software: How should self-employed people file?

    Tax software is cheaper and works fine for simple returns, while a CPA brings judgment for complex situations. But the real gap is whether your year is already organized.

    The Sumly Team
    Going Independent

    1099 vs W-2: What actually changes when you go independent

    You left the W-2 job. Now your taxes work differently. Here's what changes with self-employment tax, quarterly payments, and bookkeeping when you go independent.

    The Sumly Team
    Tax Tips

    Quarterly estimated taxes for the self-employed: a plain-English guide

    Quarterly estimated taxes are payments you make to the IRS four times a year to cover income and self-employment tax. Here are the 2026 deadlines and how to know what to send.

    The Sumly Team
    Deductions

    The home office deduction for the self-employed: a complete guide

    If you are self-employed and use part of your home regularly and exclusively for business, you can deduct it. The simplified method is $5 per square foot, up to 300 square feet.

    The Sumly Team
    Tax Tips

    How much should you set aside for taxes when you're self-employed?

    Self-employed? Set aside 25 to 30 percent of every payment for taxes. Here is how to calculate your real number and never get surprised in April.

    The Sumly Team
    Tax Tips

    Why coaches keep getting surprised by their tax bill (and how to stop it)

    Coaching income arrives from Kajabi, Stripe, PayPal, and Venmo with no running tax total. Here's why coaches get hit with surprise bills and how to stay ahead of them.

    Maggi