Quit your 9-to-5 to travel when three things are true: you have income that does not depend on your current job, you have enough savings to survive a slow few months, and you have already tested working remotely from somewhere new. If any of those is missing, you are probably better off asking for remote work, taking a sabbatical or building a side income first, and quitting later with a plan rather than a hope.
This guide helps you make that call honestly. It covers a readiness checklist, the alternatives worth trying before you resign, what you actually give up when you leave a salaried job, and how to quit well if you decide to go. If you have already decided and want the practical steps, read our guide on how to become a digital nomad with no experience.
You are probably ready to quit if…
- You have a remote job offer in writing, or your side income has covered at least half of your essential costs for three months in a row.
- You have savings for six to twelve months if you will freelance, or three to six months if you are moving into a salaried remote role.
- You know how you will handle health insurance, both abroad and if you come home.
- You have done at least one trip of two weeks or more where you worked normal hours remotely.
- You have asked your employer about remote work or leave, and the answer was no.
- You are moving toward something specific, not only escaping a job you dislike.
Tick five or six and you are in a strong position. Tick two or three and the rest of this guide will show you what to fix first.
Why “quit first, figure it out later” is risky right now
Most of the stories online are from people it worked out for. Two pieces of data explain why it often does not.
Fully remote jobs are scarce and heavily contested. Robert Half found that fully remote roles made up only about 4% of US job postings in the first quarter of 2026, with 19% hybrid and 77% fully on-site. LinkedIn reported in 2026 that fully remote roles were roughly 9% of US postings on its platform but received more than 40% of applications. Whatever the exact figure, the pattern is the same: many applicants chasing few roles. Searching for one after you have quit, while your savings shrink, is the hardest way to do it.
Self-employed income is bumpy. In the US Federal Reserve’s survey of household finances, 56% of self-employed adults said their income varied from month to month, compared with 26% of people who work for an employer. Freelancing can pay well, but you need a buffer that can absorb the lean months, especially in your first year.
The readiness checklist, in detail
| Area | Ready | Not yet |
|---|---|---|
| Income | Signed remote offer, or side income covering 50%+ of essentials for 3 months | “I’ll find clients once I’m free” |
| Savings | 6 to 12 months of costs (freelance) or 3 to 6 months (salaried remote) | Enough for flights and the first month |
| Skills | Portfolio or track record clients will pay for | Planning to learn a skill after quitting |
| Health cover | International plan chosen, home-country plan understood | Not looked into it |
| Lifestyle test | Worked remotely for 2+ weeks away from home | Only holidays, no work |
| Commitments | Lease, debts, dependents and pets have a plan | Open questions you are avoiding |
| Motivation | Clear idea of what the new life looks like | Mainly exhausted and want out |
The last row matters more than it seems. If burnout is the main driver, a change of scenery will not fix it on its own, and working while traveling can add stress rather than remove it. Our guide on avoiding burnout as a digital nomad covers the warning signs.
Try these before you resign
Quitting is only one way to get location freedom. These options keep your income while you find out whether the lifestyle suits you.
1. Ask to work remotely, from abroad
More employers say yes than people expect. In MBO Partners’ 2025 research, 18% of digital nomads with traditional jobs said their company has no nomad policy but their boss gave them permission anyway. Make it easy to agree to:
- Propose a time-limited trial, such as one month, with a review at the end.
- Name the country and confirm the hours you will cover in your team’s time zone.
- Address security (VPN, no public Wi-Fi for sensitive work) and backup internet.
- Offer to handle the visa side properly, since HR will worry about tax and immigration exposure.
MBO Partners publishes a free digital nomad request template you can adapt. Whatever you do, do not go without telling your employer. The same research found 13% of nomads with traditional jobs say their employer does not know they are nomadic, which can cost you the job if it comes out.
2. Take a sabbatical or unpaid leave
Some employers offer sabbaticals after a few years of service, and many will consider unpaid leave if you ask early and plan around busy periods. A two to six month break lets you travel, test freelancing or learn a skill with a job waiting at the end.
3. Make your employer your first client
If your role cannot go fully remote, part of it might. Offer to keep handling specific projects on a contract basis after you leave. Your employer keeps continuity, and you leave with a paying client on day one.
4. Build a side income on evenings and weekends
Treat your current salary as funding for your transition. Aim for a side income that reliably covers a meaningful share of your costs before you rely on it. Check your employment contract first for rules on outside work and conflicts of interest. For ideas, see how to create multiple income streams as a remote worker, and for help choosing a path, freelancer vs remote worker.
5. Move to a remote team internally
Large companies often have fully remote teams even when your department is office-based. An internal move keeps your benefits and seniority, and you skip the crowded external application process.
What you give up when you quit
Salary is the obvious loss. These are the ones people forget until they need them.
Health insurance
In the US, leaving a job usually ends your employer health plan. You can keep it through COBRA, usually for up to 18 months, but you pay the full premium yourself. Losing job-based coverage also opens a 60-day window to enroll in a Marketplace plan, and if you choose COBRA instead you generally have to wait for the next open enrollment period to switch. Keep in mind that most domestic plans offer little or no routine cover abroad, so you will need international or nomad insurance for your travels as well. Outside the US, check what happens to any private or employer cover and whether leaving the country affects your public healthcare rights.
Retirement contributions
Employer pension or 401(k) matching stops when you leave, and unvested employer contributions may be forfeited. Check your vesting schedule before you pick a resignation date. A few weeks can make a real difference.
A safety net if things go wrong
In most places, unemployment benefits are designed for people who lose their job, not people who resign voluntarily. Assume you will not have that fallback and size your savings accordingly.
Easy proof of income
A salaried job makes it simple to rent an apartment, get a credit card or refinance a loan. It is also often what digital nomad visas ask for, in the form of pay slips, employment letters or bank statements showing regular income. Before you resign, request an employment reference letter, download your recent pay slips and tax documents, and apply for any travel credit card you want while your income is easy to verify. Our guide to credit cards for travelers and digital nomads can help you choose.
Do the money math
Work out a “quit number” instead of relying on a feeling. Here is a simple way to do it:
- Price your new life. Estimate your monthly costs in your first destination: rent, food, coworking, transport, insurance, phone data, subscriptions and any bills you still pay at home.
- Pick your runway. Multiply that figure by six to twelve if you will freelance, or by three to six if you have a salaried remote job lined up.
- Add one-off costs. Flights, deposits, visa fees, gear and a flight home in an emergency.
- Subtract reliable income. Only count income you have actually received for three months or more, not what you expect to earn.
For example, if your destination costs $1,800 a month and you plan to freelance, nine months of runway is $16,200. Add $2,500 for one-off costs and your target is about $18,700. If your side income already averages $900 a month, the gap you need to cover from savings each month is halved, and so is the risk.
Once you are on the road, pay yourself a fixed monthly amount from a separate account and let good months top it up. This smooths out uneven income. For more on stretching your budget, see how to travel full-time on a budget, and for where to park your runway, high-yield savings accounts for digital nomads.
Be honest about the emotional side
A job gives you more than money. It provides structure, colleagues and a sense of progress. Many new nomads underestimate how much they will miss those things. Ask yourself:
- Can I set my own schedule and stick to it without a manager or an office to go to?
- How will I make friends when I change cities every month or two?
- How will I feel missing birthdays, weddings or a family emergency at home?
- What will I do if I try it for six months and want to stop? Is that a failure, or simply useful information?
Having answers does not mean you will never struggle. It means you will recognize the problem early. Our guides on work-life balance as a digital nomad and making friends while traveling solo cover the day-to-day side.
Which situation are you in?
| Your situation | Best next move |
|---|---|
| Your job could be done remotely | Ask for a remote trial from abroad before anything else |
| You have a signed remote offer | Check the offer allows working abroad, then resign and plan your move |
| Side income covers half your costs for 3+ months | Set a quit date, keep building, and save toward the full runway |
| Savings but no remote income yet | Keep your job, build a skill and first clients, then reassess in 3 months |
| Burned out and need a break | Ask for leave or a sabbatical; decide about quitting once you have rested |
Run a test trip first
If your employer allows it, spend two to four weeks working normal hours from another city or country. If not, use holiday time to do a short freelance project from abroad. Track whether you met your deadlines, what you really spent and how you felt in week three, when the novelty fades. A test trip turns a big, abstract decision into one based on your own experience. Our slow travel guide and best countries for digital nomads will help you pick somewhere suitable.
If you decide to quit: how to leave well
- Time it. Check bonus payout dates, vesting dates and whether unused holiday is paid out.
- Collect your paperwork. Employment letter, recent pay slips, tax documents and contact details for references.
- Sort health cover. Decide between COBRA, a Marketplace plan or your home country’s options, and buy international cover for your travel dates.
- Give proper notice. Offer a clean handover and mention you are open to contract work.
- Keep in touch. Former colleagues are one of the best sources of future clients and job referrals.
Frequently asked questions
How much should I save before quitting my job to travel?
Plan for six to twelve months of living costs if you will freelance, or three to six months if you are moving into a salaried remote job, plus one-off costs such as flights, deposits and visa fees. Base the monthly figure on your destination, not your current city.
Should I quit or ask to work remotely?
Ask first. If your job can be done online, a remote arrangement keeps your salary, benefits and seniority while you test the lifestyle. You can still resign later if it does not work out.
Is it a mistake to quit without a remote job lined up?
It is risky rather than always a mistake. Fully remote roles are a small share of postings and attract far more applicants than on-site roles, so a job search can take months. If you do quit without an offer, have a larger savings buffer and a clear plan for finding work.
What happens to my health insurance if I quit to travel?
In the US, your employer plan usually ends, but you can often continue it through COBRA for up to 18 months at full cost, or enroll in a Marketplace plan within 60 days. Neither is designed for long periods abroad, so most nomads also buy international or nomad-specific insurance.
The bottom line
Quitting your 9-to-5 to travel can be one of the best decisions you make, but the timing matters more than the courage. Line up income, build a runway, test the lifestyle and exhaust the lower-risk options first. When you do resign, you will be doing it from a position of strength rather than hope.
Last reviewed: September 2026. Insurance, benefits and employment rules vary by country and change over time. This article is general information, not legal, tax or financial advice.
