Side income & gig work
The money mechanics nobody hands a gig worker
Gig platforms drop income into your account with zero tax guidance, then April is a shock — that gap is the system's design, not a personal failing. This track covers the practical money side of a side hustle before anyone forms an LLC: how 1099 income differs from a paycheck, tracking the deductible expenses that lower the bill, the self-employment tax surprise and quarterly estimates, and the slow shift from hustle to real business. Warm, judgment-free, never pushy.
4 lessons · about 30 minutes total · 100% free
Saved on this device only — no account needed.
1. Getting paid as a gig worker
Gig and 1099 income lands very differently from a W-2 paycheck: nothing is withheld, the whole amount hits your account, and the tax bill arrives later. This lesson explains the forms a side hustle generates (1099-NEC and 1099-K, with its lowered thresholds), why 'it's all my money' is the trap that makes April a shock, and the set-aside mental model that keeps the tax part separate from day one. Worked in real dollars, never a directive.
7 min read
2. Tracking income and deductible expenses
The thing that quietly decides how much tax a side hustle owes isn't the income — it's whether the expenses got tracked. This lesson explains why separating business money from personal money matters, what an 'ordinary and necessary' business expense actually is (supplies, mileage, a phone or software portion, the home-office concept), the standard-mileage vs. actual-cost methods as ideas, and how good records turn real costs into lower taxable income. Educational only, never a directive.
8 min read
3. Self-employment tax and quarterly estimates
The biggest surprise in gig work is a tax most people have never heard of: self-employment tax, the full ~15.3% for Social Security and Medicare that a W-2 job quietly splits with an employer. This lesson explains where that number comes from, the deductible half that softens it, why the IRS expects estimated taxes paid quarterly, the rough four dates and the safe-harbor idea, and what an underpayment penalty is. Worked in real dollars, framed as how-it-works, never a directive.
8 min read
4. From side hustle to real business
At some point a side hustle stops feeling like pocket money and starts looking like a small business — and a few decisions change with it. This lesson explains the hobby-vs-business line the IRS draws (and why profit motive matters), when separate finances and real bookkeeping start to pay off, the point where an entity like an LLC or S-corp becomes worth considering as a concept, the retirement accounts built for self-employed people, and the reinvest-vs-pay-yourself tension. How-it-works framing, with cross-links, never a directive.
7 min read