Can I Afford to Quit My Job? Savings Calculator

Wondering if you can afford to quit your job? Use this free calculator to see how many months of savings you'd need to go full-time on your business, including self-employment tax and Connecticut health insurance, or run a simple savings runway check before retiring. Checked November 3, 2026.

For general education only. Not tax, legal, insurance, or investment advice, and not a promise of any result. Tax rules and due dates change, so confirm with the IRS (irs.gov), the CT Department of Revenue Services (portal.ct.gov/DRS) or your town before you act, and ask your tax preparer about your own situation.

Can I afford to quit my job and go full-time on my side business?

Enter your own numbers. The calculator estimates self-employment tax, sets aside income tax at the rate you choose, adds the health insurance you'd now pay yourself, and shows how many months of savings you'd need.

Your business (monthly, once you go full-time)

Expected business revenue per month

What customers would pay you, before expenses. Be realistic for the first months.

Business expenses per month

Software, supplies, mileage, insurance, rent and so on.

Income tax set-aside rate, federal + CT (%)Your own estimate of income tax as a % of profit. Ask your tax preparer. Self-employment tax is calculated separately below.

Your household (monthly)

Health insurance premium you'd pay per month

Replacing employer coverage, for example a plan through Access Health CT. Enter your quote.

Household living costs per month

Rent or mortgage, food, car, debt payments, everything not counted above.

Other household income per month

For example, a partner's take-home pay.

Your cushion

Months until the business covers its share (build-up period)Your guess at how long revenue takes to reach the level above.

Revenue during the build-up period, as % of the full amountFor example, 50 means you expect half of the revenue above during the build-up period.

Emergency cushion to keep, in months of living costsMoney you don't plan to touch.

Savings you could use

Cash you'd draw on, not retirement accounts.

Before you quit your job: costs people forget

Self-employment tax. Employees split Social Security and Medicare with their employer. Self-employed people pay both halves: 15.3% on 92.35% of net earnings (12.4% Social Security up to $184,500 of combined wages and net earnings for 2026, plus 2.9% Medicare), once net earnings reach $400. IRS
Quarterly estimated taxes. Without a paycheck there's no withholding, so you generally pay federal and CT estimates four times a year. See our quarterly tax guide and deadline reminders.
Health insurance in Connecticut. Losing job-based coverage is a qualifying life event: Access Health CT generally gives you 60 days from the event to enroll, and you'll need proof (such as a termination letter) within 30 days. Quitting your job ends the employer coverage; a voluntary cancellation of the plan itself doesn't qualify. Access Health CT: Special Enrollment Periods
Health premiums may be deductible. Self-employed people may be able to deduct health insurance premiums (IRS Form 7206). Ask your tax preparer whether it applies to you. IRS: About Form 7206
Lumpy income. Client payments arrive late and some months are slow. That's why the calculator has a build-up period and a cushion.

Thinking about retiring early? What this runway check leaves out

The retirement tab only counts cash: no growth, no market assumptions, no product picks. For decisions about Social Security timing, account withdrawals or investments, talk with a qualified, licensed professional. Medicare is generally for people 65 or older (Medicare.gov), so if you retire before 65, plan for the cost of other coverage.

Frequently asked questions

How much savings do I need before quitting my job to work for myself?

It depends on your numbers. This calculator adds your living costs and health insurance, subtracts what the business would bring home after self-employment tax and an income tax set-aside, then multiplies any gap by your build-up months and adds the emergency cushion you choose.

How is self-employment tax calculated?

For 2026 it's 15.3% on 92.35% of net self-employment earnings: 12.4% Social Security on up to $184,500 of combined wages and net earnings, plus 2.9% Medicare. It applies once net earnings are $400 or more.

Can I get health insurance through Access Health CT after I quit my job?

Losing job-based coverage is generally a qualifying life event. Access Health CT says you generally have 60 days from the event to enroll and 30 days to submit proof, such as a coverage termination letter.

Does the retirement calculator assume investment returns?

No. It assumes your savings earn nothing, so it's a simple cash-flow count, not a forecast or investment advice. You can test rising living costs with your own yearly percentage.

Is this calculator financial advice?

No. It's an educational tool that does math on the numbers you enter. For your own decisions, talk with your tax preparer or another qualified professional.

Sources (Checked November 3, 2026)

Planning the jump to self-employment? We can help you set up estimated taxes and your books before you go.

Request a quote Book a 15-minute call

Or call (475) 242-7941. Services are priced by quote.

Enhance Finance is a small-business finance practice serving Connecticut.