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Freelancers and the self-employed

10 moments for freelancers and the self-employed.

Name the moment, not the job title. Each one has a hook line to open a post or video with, its ringtone (the letter, bill or date people react to before they think) and what's at stake.

  1. First 1099

    “Your first 1099 means nobody is withholding tax for you. Set aside 25-30% now.”
    Ringtone
    The first client payment
    What's at stake
    Self-employment tax and quarterly estimates surprise first-year freelancers.
  2. First quarterly estimate

    “Quarterly estimated taxes are due in April, June, September and January. Miss one and the penalty starts.”
    Ringtone
    The estimate deadline
    What's at stake
    Underpayment penalties and cash flow planning.
  3. Health insurance on your own

    “Leaving your employer's health plan? Your income estimate decides your marketplace subsidy.”
    Ringtone
    The marketplace application
    What's at stake
    Premiums depend on projected income; misestimating means paying back subsidies.
  4. Opening a solo 401(k)

    “Self-employed with no employees? A solo 401(k) lets you save as both employer and employee.”
    Ringtone
    A big income year
    What's at stake
    Solo 401(k)s and SEP IRAs allow large tax-deferred savings.
  5. Lumpy income year

    “Best year ever, followed by a slow quarter? Budget off your worst month, not your best.”
    Ringtone
    Two months without a payment
    What's at stake
    Irregular income needs a cash buffer and a pay-yourself system.
  6. Forming an LLC or S corp

    “Should your freelance business be an S corp? It depends on your profit, not your pride.”
    Ringtone
    Paying more in self-employment tax than income tax
    What's at stake
    Entity choice changes taxes and paperwork.
  7. Home office and deductions

    “Working from home? The home office deduction has rules. Know them before you claim it.”
    Ringtone
    Tax season
    What's at stake
    Deductions reduce tax but need records.
  8. Applying for a mortgage

    “Self-employed and buying a house? Lenders want two years of tax returns, not your invoices.”
    Ringtone
    The mortgage application
    What's at stake
    Write-offs that cut taxes also cut qualifying income.
  9. Disability with no employer coverage

    “If you couldn't work for six months, who pays you? Freelancers have no sick leave.”
    Ringtone
    An injury or illness
    What's at stake
    Individual disability insurance replaces lost income.
  10. Going back to a W-2

    “Offered a full-time job after years freelancing? Compare the benefits, not just the salary.”
    Ringtone
    The job offer
    What's at stake
    Benefits, retirement plans and taxes change.

Make a video about one See advisors for freelancers and the self-employed

General education, not financial advice. Check rules and figures against current law before you publish.