You’ve had enough. Maybe your boss micromanages every email you send, or your workload has tripled without a corresponding bump in pay. Perhaps you’re simply bored out of your mind, watching the clock like it’s moving backward. Whatever the reason, you’re ready to walk out that door and never look back.
But hold on a second. Quitting your job is one of those decisions that feels urgent in the moment yet demands careful thought. Sure, something is thrilling about the idea of handing in your resignation letter and starting fresh somewhere new. But there’s also rent to pay, bills stacking up, and a whole lot of life that keeps happening whether you have a steady paycheck or not.
Before you march into your manager’s office with your two weeks’ notice, take a breath. Here’s what you need to think through first.
Things to Think About Before Quitting Your Job
Leaving a job is rarely as simple as we’d like it to be. These considerations will help you make a choice you won’t regret three months down the line when reality sets in.
1. Your Financial Safety Net
Let’s talk money first because everything else hinges on this. How much do you have saved right now? Not what you hope to save or plan to save, but actual cash sitting in your account that you could access tomorrow.
Financial experts typically recommend having three to six months of living expenses tucked away before making any major career move. That means if your monthly bills total $3,000, you should ideally have $9,000 to $18,000 saved up. This isn’t just for rent and groceries either. Think about your car insurance, that streaming subscription you forgot about, your gym membership, and yes, the occasional coffee run that keeps you sane.
Here’s the thing though. Most people don’t have that much saved, and that’s okay. What matters is being honest with yourself about what you can actually afford. Can you cover your basics for two months? Three? If the answer is less than one month, you might want to start building that cushion before you quit. There’s nothing worse than the freedom of unemployment turning into the panic of unpaid bills.
2. The Health Insurance Puzzle
You probably don’t think about your health insurance much until you need it. Then it becomes everything.
When you leave your job, you’ll lose your employer-sponsored health coverage. COBRA exists, sure, but it’s expensive because you’ll be paying both your portion and what your employer used to cover. We’re talking potentially $600 to $800 per month for an individual plan, sometimes more for family coverage. That’s a chunk of change.
Before you quit, figure out your options. Can you get on a spouse’s or partner’s plan? Does your state have affordable marketplace options? How long can you realistically go without coverage if you’re young and healthy? And if you have any ongoing medical needs or take regular prescriptions, factor those costs into your budget. Breaking your ankle during a gap in coverage is a financial disaster you don’t want to experience firsthand.
3. What the Job Market Actually Looks Like
You’ve been scrolling through job listings at midnight, and it seems like there are plenty of opportunities out there. But are there really?
Take a hard look at your industry right now. Are companies hiring or freezing positions? Tech layoffs, retail restructuring, and industry-specific downturns happen all the time. What looks like a robust job market on the surface might actually be dozens of people competing for every single opening. Check sites like Glassdoor or industry-specific job boards. See how many positions match your experience level. Better yet, reach out to recruiters in your field and ask them what they’re seeing. Their candid feedback will tell you whether you’ll land something in three weeks or three months. That timeline matters enormously when you’re living off savings.
4. Why You Really Want to Leave
This one requires brutal honesty. Why are you actually quitting?
Is it your boss? Your coworkers? The work itself? The commute? The pay? Lack of growth opportunities? Write it down if you need to. Sometimes seeing your reasons on paper makes them clearer. Because here’s what happens: if you’re leaving because you’re burned out, that exhaustion might follow you to the next job if you don’t address the root cause. If it’s a toxic manager, great, a new company solves that. But if you’re bored with your entire career path, switching companies won’t fix the problem.
Be real with yourself. Are you running away from something or running toward something better? There’s a difference, and it matters.
5. Whether You’ve Actually Tried to Fix Things
Before you burn the bridge, have you tried repairing it?
So many people quit without ever having that difficult conversation with their manager about what’s bothering them. If you’re overwhelmed with work, have you asked for help or raised concerns about unrealistic deadlines? If you feel underpaid, have you researched market rates and made a case for a raise? If you’re bored, have you requested more challenging projects or a role change?
You might be surprised at what’s possible when you actually speak up. Maybe your company has a transfer program you didn’t know about. Maybe your manager has been oblivious to your struggles and would genuinely work with you to make things better. Or maybe you’ll get confirmation that nothing will change, and then you’ll know for certain that leaving is the right call. Either way, at least you tried.
6. Your Next Move
Here’s a question that stops people in their tracks: what are you doing after you quit?
Do you have another job lined up? Are you taking time off to regroup? Starting a business? Going back to school? Freelancing? Each path requires different preparation and different financial runway. Quitting without a plan is like jumping out of a plane without checking if you packed a parachute. Maybe you’ll figure it out on the way down, but why take that risk?
If you don’t have your next move mapped out, spend time on it now while you still have income. Update your resume. Start networking. Take that certification course. Having a direction, even a rough one, makes the transition so much smoother.
7. Your Professional Relationships
Your coworkers might drive you crazy sometimes, but they’re also your professional network. How you leave matters.
Will you need references from your current company? Do you have allies who could vouch for your work? Are there people you genuinely want to stay connected with after you’re gone? Think about the relationships worth maintaining. Even if you can’t stand your boss, maybe there’s a colleague in another department who respects your work. Maybe there’s someone junior you’ve mentored who’ll remember your kindness.
People change companies all the time in most industries. You’ll run into former coworkers at conferences, see them on LinkedIn, maybe even work with them again someday. Leaving on decent terms, even from a bad situation, keeps those doors open.
8. Life Timing
Timing isn’t just about the job market. It’s about your life.
Are you about to close on a house? Lenders really don’t like it when you change jobs mid-mortgage process. Are you getting married in three months? Planning a big move? Dealing with a family member’s health crisis? Expecting a baby? All of these things create additional stress and financial pressure that compounds the challenge of changing jobs.
Sometimes you don’t have the luxury of perfect timing. Life is messy and unpredictable. But if you can control when you make this change, consider what else is happening in your world. Maybe waiting two months makes everything else fall into place more easily.
9. The Benefits You’re Giving Up
Your paycheck isn’t the only thing you’re walking away from.
Add up everything else: your 401(k) match, paid time off, sick days, that free gym membership, commuter benefits, employee discounts, stock options, annual bonuses, professional development budgets. Companies often offer perks you’ve stopped noticing because they’ve become routine. But they have real monetary value.
Let’s say your company matches 5% of your salary in your 401(k). On a $60,000 salary, that’s $3,000 of free money every year. Add in three weeks of PTO, health insurance premium contributions, and other benefits, and you might be getting an extra $15,000 to $20,000 in value beyond your base pay. Your next job needs to account for that total compensation package, not just the salary number.
10. Contractual Fine Print
Pull out your employment paperwork and read it. Really read it.
Do you have a non-compete agreement? Non-solicitation clause? Are you bound by any contractual obligations that restrict where you can work next or what you can do? These agreements vary wildly by state and industry. Some are enforceable, others aren’t, but you need to know what you signed.
Also check if you owe anything back to your company. Did they pay for your master’s degree with the agreement you’d stay for two years? Did you get a signing bonus that requires repayment if you leave within a certain timeframe? Did they relocate you? These clawback provisions are real, and ignoring them can result in unexpected bills landing in your mailbox after you’ve already left.
11. Your Emotional State Right Now
How are you feeling today? Not just about work, but about everything.
If you’re going through a particularly rough patch personally, if your mental health is struggling, if you’re dealing with grief or major stress, that colors your judgment. What feels unbearable today might look different in two weeks. This isn’t saying your feelings about your job are invalid. They’re probably completely justified. But making massive life decisions while you’re already emotionally depleted can lead to choices you later regret.
On the flip side, if this job is actively harming your mental health, if Sunday nights fill you with dread, if you’re having physical symptoms from stress, then leaving might be the healthiest thing you can do. Just be honest about whether you’re making a decision from a place of clarity or crisis.
12. Your Market Value
What are you actually worth right now?
Research what people with your experience, skills, and location are earning. Sites like Glassdoor, Payscale, and industry-specific salary surveys can give you ballpark figures. Talk to recruiters. Join professional groups where people discuss compensation openly. You might discover you’re underpaid and have leverage you didn’t know about. Or you might find out you’re actually compensated fairly for your market, which changes your negotiating position.
Understanding your value also helps you set realistic salary expectations for your next role. If you’re making $55,000 and hoping to jump to $85,000, that’s possible in some scenarios but unlikely in others. Knowing the realistic range helps you evaluate offers and negotiate effectively.
13. How You’ll Actually Leave
There’s strategy in how you exit.
Two weeks’ notice is standard, but is it enough time to wrap up your projects properly? Do you have critical knowledge that needs to be transferred? Are you in the middle of something that would leave your team in a terrible position if you left abruptly? Leaving professionally doesn’t mean you owe your company everything, but it does mean thinking through the logistics.
Write your resignation letter before you need it. Keep it brief, professional, and positive. You don’t need to explain all your reasons or air grievances. Just state that you’re resigning, provide your last day, and express appreciation for the opportunity. Save the honest feedback for an exit interview if you choose to participate in one, though know that exit interviews rarely lead to company changes.
14. Unemployment Benefits Eligibility
If things don’t go according to plan, can you fall back on unemployment?
Here’s the catch: if you quit voluntarily, you typically can’t collect unemployment benefits. They’re designed for people who lose jobs through no fault of their own. There are exceptions like quitting for good cause or constructive discharge, but those have specific legal definitions that vary by state.
This matters if your next job falls through or takes longer to find than expected. If you get laid off, you have that safety net. If you quit, you don’t. Sometimes it makes sense to have a conversation with your employer about a mutual separation agreement, especially if the relationship has deteriorated. But understand what you’re giving up when you voluntarily resign.
15. Retirement Account Decisions
What happens to your 401(k) when you leave?
You have options: leave it where it is, roll it over to an IRA, move it to your new employer’s plan, or cash it out. That last option is almost always a bad idea unless you’re in dire straits. You’ll pay taxes on the full amount plus a 10% early withdrawal penalty if you’re under 59½. On a $30,000 balance, that could mean losing $10,000 or more to taxes and penalties.
Rolling it over to an IRA usually makes the most sense. You maintain the tax advantages and often get more investment options. Just don’t miss the 60-day window if you do an indirect rollover, or you’ll face those penalties. This stuff matters because that retirement money needs to keep growing for your future.
16. Your Reputation in Your Industry
Industries are smaller than they seem, particularly specialized ones.
Word travels. How you conduct yourself at your current job becomes part of your professional reputation. If you leave projects unfinished, if you badmouth your employer publicly, if you burn bridges on your way out, people remember. Hiring managers check references. Colleagues from your old job end up at companies you’re interviewing with. The recruiter you ignored might be at your dream company five years from now.
This doesn’t mean you can’t leave a bad situation or that you owe toxic employers anything. It means being strategic about how you do it. Professional doesn’t mean being a doormat. It means handling your exit in a way that protects your future opportunities.
17. Alternative Solutions You Haven’t Considered
What if you don’t have to quit?
Some companies offer sabbaticals or leaves of absence for personal development. Could you take unpaid time off to recharge without fully severing the relationship? Is there a different role in your company that would solve your problems? Could you negotiate remote work if your commute is killing you? What about going part-time temporarily while you figure things out?
Sometimes we get so focused on leaving that we miss creative solutions. Especially if you like your company overall but hate your specific situation, internal moves can give you a fresh start without the financial risk of unemployment. At minimum, exploring these options gives you more information to make your final decision.
18. Your Dependents and Family
Who else is counting on your income and benefits?
If you’re supporting kids, a partner, aging parents, or anyone else, your decision ripples out to affect them too. This doesn’t mean you should stay in a miserable job forever for their sake. It means factoring their needs into your planning. Do your kids need to stay in their current school district? Does your spouse’s job provide backup benefits? What’s your family’s risk tolerance for financial uncertainty?
Have honest conversations with the people who’ll be affected. They might surprise you with their support and flexibility. Or they might raise concerns you hadn’t considered. Either way, making this choice together, when possible, leads to better outcomes for everyone.
19. Location and Relocation Factors
Where you work matters as much as what you do.
Are you willing to relocate for the right opportunity? If not, how many suitable jobs exist in your area? If you live in a small town or specialized market, leaving your current employer might mean either accepting a significant commute or moving entirely. Remote work has opened up possibilities, but not every industry or role offers that flexibility.
Think through the practical realities. If you’d have to move for your next job, can you afford that? Do you want to uproot your life? If you’re staying local, what’s your backup plan if options are limited? Geography constraints are real, and they narrow your choices in ways that matter.
20. Your Long-Term Career Vision
Zoom out for a minute. Where do you want to be in five years?
Does quitting this job move you closer to that goal or further away? Sometimes taking a step back or sideways is necessary to eventually move forward. Sometimes staying in an imperfect job for another year to gain specific experience is the strategic choice. Sometimes leaving immediately, consequences and all, is exactly what your long-term trajectory needs.
Think about the skills you want to build, the reputation you want to have, the lifestyle you want to live. Does your current job support any of that? Would your next move, even if uncertain right now, create better possibilities? Your career is long, and one decision rarely ruins everything. But being intentional about the direction you’re heading makes each choice count more.
Wrap-up
Quitting your job isn’t just about having enough or feeling done. It’s about having a plan, understanding what you’re walking away from, and knowing what you’re walking toward.
Take your time with this decision. Talk to people you trust. Run the numbers. Sleep on it. The right choice will still be the right choice in two weeks, and you’ll feel more confident about it.
Whatever you decide, make it with your eyes wide open. That’s how you avoid regret and set yourself up for whatever comes next.