Michael West Financials · Conversation guide
Starting gig or 1099 work.
A gig pays you directly — no HR, no benefits portal, nothing withheld. That freedom is real, and it quietly hands you four jobs an employer would normally do for you. This sheet is for picking them up on purpose, together, before they pick you.
1 · Which kind of gig?
"Gig work" hides the question that decides everything else: who the tax form says you are. Tick the one that fits — when in doubt, ask the payer which form you'll get.
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1099 contractor
ride-share, delivery, freelancing — nothing withheld; taxes and retirement are yours to set up
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W-2 agency employee
catering, banquet, staffing — taxes withheld, but benefits usually still don't come with it
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Paid in cash
babysitting, odd jobs — still taxable; keep a log, because only documented earnings can fund a Roth
The rest of this sheet assumes the 1099 or cash case — that's where the surprises live.
2 · Four jobs an employer would do — now yours
Check each one off as you set it up. They didn't vanish with the employer; they became yours to assemble.
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Buy your own health coverage
use the ACA marketplace (healthcare.gov or your state's exchange) — subsidies scale to income, and a lean gig year often means a cheap plan. Don't go uninsured to save the premium.
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Set aside your own taxes
nobody withholds. Park about a third of every payment the day it lands, and pay the IRS in four quarterly estimates — skip them and penalties stack up.
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Build a bigger cash buffer
no paid time off means a sick week is a week of lost pay. Aim closer to six months than three.
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Open your own retirement account
no match to capture, but no vesting clock either — a Roth IRA is yours the day you open it.
3 · Talk it through
- Which form will this gig actually pay on — 1099, W-2, or cash?
- Where will the tax set-aside live, so it's not spent by mistake?
- What's a realistic per-month buffer goal, given the income swings?
- Does a higher gig rate still win once taxes, health, and unpaid days come out of it?
4 · One move this week
Four jobs is a lot to pick up at once, and health, taxes, and the buffer can be set up over the coming weeks. One move can't wait, because every week it slips is a week of compounding you don't get back.
Open a Roth IRA and set one small automatic contribution from your gig income. No employer will ever do this for you — which means none can ever stop you either.
No employer means no floor — and no ceiling. Assemble the pieces on purpose and a gig can pay better than the salaried job it stands in for. Based on the gig-work lesson.