How to Quit Your Job Without Burning Bridges (13 Easy Strategies)

By Sean Ogle •  Updated: 05/02/18 •  24 min read

Note: We updated this post on how to quit your job for accuracy in May 2018.The 13 Approaches to Quitting Your Job (Without Burning Bridges)

Oftentimes the most difficult aspect of quitting your job isn’t figuring out what to do next.

You could go climb a mountain. Build out any number of a hundred business ideas you already have. Sit on a beach in the tropics for a month.

There’s no shortage of things to do with free time.

No, the hardest part of quitting your job is often the simplest: telling your boss or current employer that you plan to leave.

It doesn’t matter if you’ve been working with them for 6 months or 6 years when you’re spending more time with them than your own family. It can be an agonizingly personal endeavor to tell them you want to go elsewhere. It’s almost like going through a breakup after years of dating.

Throughout the years, I’ve been working with people to help them quit their jobs and build sustainable businesses. I’ve seen all kinds of different ways to approach that fateful day where you march in and say “hey boss, I’m outta here.”

Sometimes it goes really well.

Other times? Well, not so much.

So if you’re thinking about quitting your job, how are you going to approach it? What’s your reasoning going to be? How are you going to get them to understand exactly why you’re doing this? What do you need to do in order to prepare for the big day?

Easy, you’re going to read this guide.

Here we will talk about 13 different approaches to leaving your job, the potential objections/responses to each, and how you can prepare yourself beforehand to give yourself the best shot of remaining on good terms after your last day.

Also, here’s a really cool story about how a photo of me and one of the most successful entrepreneurs of all time led to me quitting my job.

On Quitting Your Job Nicely

My goal with these was to make the departure as positive as possible for both parties.

In an ideal world, you don’t want to burn bridges when quitting your job.

There are a few reasons for this, but here’s one most people don’t think about:

Your old boss or company could make an awesome new client.

We just had this scenario happen inside the Location Rebel Forums. Someone who had joined a few years ago after quitting her job on good terms with her boss was just hired to consult for her old company.

Since she already worked there, she understands company culture and what they are looking for, which is awesome.

And the kicker? They are paying her way more now as an outside consultant than they ever did as an employee.

So keep that in mind, this isn’t the first time we’ve heard this type of story.

One last note on this though, sometimes hard feelings are just going to be there, no matter how you approach qutting your job. Your boss just might not be happy. It’s not the end of the world, but keep it in the back of your mind.

Alright, ready to dig in?

Now, onto the 13 approaches for quitting your job!

#1: The Quarter Life Crisis

One of the most common approaches to leaving your job comes from those who have graduated within the last five years and are often still in their first job out of college.

This is a tough place to be.

I’m willing to bet your first job out of school wasn’t your dream job, yet here you find yourself still working away without much to show for it.

Even worse, you may have a completely unwarranted sense of obligation to your employer.  I did. I felt like since they took a shot on me, I had to stick around forever.


You can use the quarter-life crisis approach in numerous ways. Tell them you need more life experiences, need to figure out what gets you excited.

This is the absolute best approach when the only thing you know is school and this one job. You need to have a myriad of experiences so you can figure out what’s actually right for you, not just what’s easiest.

Common Objection: Are you sure you know what you’re doing? You’re just going to have to start over again in 6 months.

Reality: Taking time off to travel and figure out what you want out of life is only going to make you more marketable to employers in the future. If you get back and have realized exactly the type of work you want to be doing in the future, they will have more confidence in your long term commitment to the organization.

#2: The Timebomb

So you know you want to leave, but you know you won’t be ready for another 6-12 months.  You also know that you don’t want to leave your boss out in the lurch and want to make sure he isn’t blindsided.

So what do you do? You adopt the Timebomb Principle like John Devries and others have done.

What does this mean?

Essentially you pick a date in the future that you’re absolutely, no matter what, going to leave.  Assuming you have a good, trusting relationship with your boss you tell them about your plan.  You explain all the reasons you need to go (of which I’m sure there are many), and work together on your exit date.

During the final few months, you can help to find and train your replacement to ensure there is no lost progress. This leaves your boss ahead of the game, and you’re able to really put a good exit plan into place over the long term.

John Devries on his motorcycle

John DeVries perfected the Timebomb Method

Common Objection: Why shouldn’t I just fire you right now?

Reality: Knowing that you’re going to be leaving helps keep things on the right track during your final months.

If your boss knows you’re going soon, and you’re one of their star employees, they’ll want to utilize you for every day they have.

They are also getting the benefit of a new hire, trained by the expert (you) rather than having to start from scratch.

Again, this works best if you have a really good relationship with your boss, and I’ve seen numerous people have success with this in the last couple years.

#3: The Entrepreneur

If you’re anything like me, you want to own your own business.  You want the freedom, responsibility, and rewards that go along with being an entrepreneur.

If you’re stuck working for someone else, regardless of how sweet the job is, your lust for entrepreneurship will never be satiated until you give it a shot.

Until you do it, you’ll always be left wondering “what if” – a feeling no one should have to experience.

So if this is you, think long and hard about the type of business you want to run.  Get started on the weekends and in your spare time, and once you’ve got some proof that the idea is viable, it’s time to break the news.

Talk to your boss and tell them about your entrepreneurial visions.  This works especially well for small businesses where they are also entrepreneurs – they’ll get it, trust me.

Depending on the type of services or products you’re offering in your new business, your current employer could potentially be a great first client.

For instance, my friend Zach quit his job as a developer so he could focus more on the projects he was actually passionate about.

His company couldn’t stand the thought of him leaving, so they asked him to continue to do some work part time even after he left. He now gets to work remotely, works half as many hours, and still makes almost as much as he was making before. Talk about a Linchpin.

Common Objection: In this economy, you’ll never be able to make it alone, you should be lucky to have any job at all, why would you want to throw that all away?

Reality: Even if you stay there are no guarantees. They can sack you anytime they want, so by working for yourself you’re beginning down the path of true job security or job security 2.0 as I call it in Location Rebel.

Worst case scenario? You go back and get a job when you need to – but at least you’ll no longer be wondering “what if?”

#4: The Remote Work Agreement

This can be a great approach depending on a few key aspects of where you’re at:

I love the remote work agreement because it gets you one step closer to becoming a location rebel.  It allows you to go somewhere new, set your own schedule (usually), and shows you what it’s really like to be on your own.

This can be a great test case for whether or not you’re really ready to branch out on your own accord.

Evan Lovely is one of the best examples of this.

He talked his boss into letting him travel through Asia for 6 months while still taking a full salary and working on the road.

We hung out in Bali a few years ago, and don’t get me wrong, he worked hard, but he essentially had all the benefits of being on his own, while still having the stability of a real job.

This can be good either way. If they accept your proposal, sweet! You’re one step closer to your goals. If they don’t, well then you gave it a shot, and you and your boss may just realize your employment isn’t a good fit.

Or door #3 is they simply say no, and you have to move onto one of these other approaches to quitting your job.

Common Objection: Why should you be able to take off to Bali, Belize or Boise while we’re still here in the office?  You’ll be way less productive.

Reality: If you’re serious about this, your remote work can actually be a huge asset to the company.  It has the potential to save them money (depending on the agreed upon terms), bring their business into the 21st century with improved security and remote computer access, while also potentially opening up a whole new client base due to your new location.

If you work for a small company in the US, they could even potentially use you as their “international” office and make themselves seem like more of a global institution.

#5: The Upping the Ante

Maybe you want to leave your job, but it’s mostly because you aren’t being compensated fairly, or you’re otherwise not happy with the effort vs return.

With the upping the ante, we strive to get to the point where you’re either getting the compensation you feel you deserve, or you cut all ties and move onto something more worth your time.

My friend Beau moved down to the Bay Area from Portland last year after his company asked him to head down for a series of projects.  He was only supposed to be there for 6-12 months, but then they asked him to stay longer.

He owns a house in Portland, has a large social circle up here, and really would prefer to be in Oregon than California.  So he initially told his company he wanted to head back to PDX.

They said:

“How much would it take for you to stay?”

The result: He ended up with a huge raise, better benefits and an increased living stipend to stick it out for another year or two.

When you know your company needs you and you’re willing to stay for a price, don’t mess around.  Give them the real number or offer that will make it worth your while to stick it out for awhile.

If they can’t get reasonably close to matching it, then find someone who will.

Common Objection: We’ve never given anyone a 50% raise! That’s insane!

Reality: What’s more expensive for them? Give the dude that’s killing it for them and making them millions of dollars a year a little extra money?  Or have to go through the entire hiring and training process all over again?  If you’re legitimately good at what you do, they’ll understand why they need to pay you.

#6: The Bluff

Similar to upping the ante, the bluff isn’t really a straight up tactic for quitting, but rather an understanding of the importance of your place in the company.

Jennifer did this and didn’t even realize it. We’d been talking back and forth on strategies for building her new writing business, while also getting her to the point where she was willing to take the nerve-wracking step of quitting her cush job.

After finally getting to the point where she worked up the nerve to do it, you know what her boss said?

“No.  I can’t let you quit.”

How’s that for a momentum killer?

She was already nervous enough as it was, and then her boss took away all her confidence and she didn’t know what to do.  She agreed to stay on for a month, which gave her boss more time to plan out what was next.

She realized in that month just how valuable she was – she knew there was a way to get much more than she was currently, while still setting a timeline for her departure.

After some back and forth, she agreed to a big raise and to stay on until the rest of the year.  All the while, she’s still been growing her business and has landed a couple HUGE writing gigs.

Now not only will she have the money to really pursue her new business early next year, but she’ll already have the brand, contacts, and confidence in place to do it.

Common Objection: You can’t quit no one will ever hire you again, you need this. (This was the experience Jennifer actually had).

Reality: You don’t need any job, however, there’s a very good chance they need you.  If you know this is the case, leverage it, and consider a bluff.

That said you should be prepared for them to call it. If you aren’t in a place where you’d follow through with your resignation if they don’t give in, then you should probably stick around for awhile longer or try a safer approach.

#7: The Lack of Heart 

No boss can ever get mad at you for being honest about this one.  If they do – then you didn’t want to be there in the first place.

The best example of the “lack of heart” I’ve seen is from Lizzie Presson.  Here’s the email she sent to me detailing her situation:

I quit my job, packed my bags and moved to NYC one year ago (July 23rd to be exact). My mentor (Amber Rae) called me and said she wanted me to come work with her in NYC. My boss was on a two week vacation. I called him and told him that I hated to tell him over the phone, but I had to be upfront and honest.
I remembered that a couple of days before I had the news to share he said, “I don’t want anyone working here who isn’t in 100%.” I reminded him of that moment, and I told him that I’d never want to give less than 100%. I would be if I didn’t leave at that very moment (with proper notice of course).
After I landed what I thought was my dream job and taking the risk, it became apparent that the job was not the right fit. I was jobless for the first time ever, living in NYC alone and more confused and scared than ever.

That fear ended up being the best thing that’s ever happened to me. Now, I’m co-founding a new business with someone I respect, and I’ve launch a meaningful project,

Any good boss (you know, or human being) will respect this, and will likely do whatever they can to support your decision.

If you’re struggling with a lack of heart, then think about what would inspire you.  Start looking for opportunities that are in line with that, or simply create your own and become “the entrepreneur” 🙂

Common Objection: What could we do to help you rekindle your passion within our organization?

Reality: This is actually a valid objection.  Before you go to your boss and talk to them, consider an answer to that question. Is there anything that would get your heart back in it?  If not, recognize this and stick to your guns.

If you think there is a way you could re-find that passion, try setting up a meeting to chat about it before quitting.  Give them a chance to make the situation better.  If 2-3 months later nothing has improved, then say peace and move on to bigger and better things.

#8: The Budget Cut

Ah the dreaded budget cut.

The re-org. The downsizing. Whatever name you want to give it, it can be a terrifying thing for a lot of employees.

But what if you were already thinking about quitting?  Then maybe it doesn’t have to be such a scary thing.  In fact, maybe it can be a positive for both you and your boss.

If you know there’s a round of layoffs coming, go to your boss or whoever is in charge of making the layoff decisions and have an honest conversation, and see if it would help them out if you volunteered to be laid off.

Often times that’s one less person they have to break bad news to, and that also means that you could be eligible for severance, and at the very least, unemployment benefits.

Approach this one delicately, as your boss could simply fire you (justly) on the spot.  That said, if you have a good relationship, maybe go out for a drink or coffee.  Tell them what you’re thinking and see how they feel about it.  When executed properly this is one of the best ways to leave because every party wins, and you get some help financially while you start your business or figure out what’s next.

Common Objection: Why are you telling me you don’t want to work here anymore? You know I can fire you now because of that?

Reality: If you do it right, they should sense the empathy you have for their situation, as well as your desire to make a change in your own life.  If you’re considering this, then that means at the very least you aren’t happy there anyway, so worst case they fire you and you don’t get severance.  Best case, you stay good friends, and get a head start on your new path.

#9 The Ease Out

Still not feeling good about leaving your old company hanging out to dry? Propose easing yourself out of the position.  Pick a time frame, maybe 3 months or so, and come up with a plan for slowly taking yourself out of the position.

Part of that could include training new employees, current employees taking over your duties, and documenting all of your daily processes/tasks.

Month one could be you working full time, month two has you going down to 3 days a week, and maybe the final month is once a week or working remotely and simply coming in as needed.

The goal of the ease out is to reduce the shock, confusion, and stress of suddenly losing a vital part of the organization.

This also allows you some time to slowly ramp down your time commitment on the old job, which allows you to ramp up your new business, while still having some financial security during those first few months.

Common Objection: We have too many valuable things going on to deal with this, we should probably just let you go now.

The Reality: Offer to handle the details.  Before you approach, this lay out a detailed plan.  You’re already a part of the team, so make sure you think through how current projects will be finished up if you’re easing out.  If you’re unorganized or don’t have a plan, they’ll see no benefit to the ease out – they’ll just walk you out right then and there.

#10: The Template

Figuring out exactly how to word your departure, or exactly how what to say when you give your two weeks notice can be incredibly difficult.  Lucky for you there’s no shortage of templates out there to help you figure out exactly what to say.

If you want to cover your bases and make sure you cover the necessities, take this actual resignation letter that Barrett so kindly submitted, fill in the blanks, and set up an appointment with your boss.

Resignation Letter Template

Be honest.  Tell them exactly how you feel, and why it’s time for you to go elsewhere.  Don’t like this template?  That’s cool, just do a quick Google search for “job resignation template” and you’ll find all sorts of other routes you can take.

Common Objection (from Barrett’s Boss): Where are you going? What are they paying you?

Reality: Like any good person, after Barrett told his boss that he was setting out to start his own business, the response immediately changed to “how can I help.”

As with many of the approaches we’re looking at today, if your goal is genuinely to improve you life and do something meaningful, they’ll usually respect your decision.

#11: The Milestone

Oftentimes having a milestone in mind that you can use to fuel your fire for leaving is an incredible help.

Stuart gave me a great example of this:

On August 23 I will have been with my current employer for 5yrs and I thought there is no way I want to cross that milestone (for fear I may never get out). So, I decided that I should leave on August 22 and not look back.

The longer you’re on a job, the harder it is to leave, simple as that.  In my own case, the recession and financial crisis proved to be a blessing in disguise.  Had the economy gone the opposite way, my job situation would have been a lot more comfortable, and there’s a good chance I’d still be there today.

By picking a milestone, 5 years for Stuart, and saying I’m going to be out by then, it allows you to start planning accordingly.  This is similar to the Timebomb Method, but with “the milestone” you may or may not work with your employer to make it happen.

Stuart said both his coworkers and boss tried to convince him to stay, but he held true to his guns and mentioned that 5 years is a long time to be somewhere these days, and he needed to do this for himself.

Common Objection: Why would you want to leave now? At 5 years you get better benefits and an extra week of vacation!

Reality: Being anywhere for 5 years leaves you with a greater sense of commitment than ever.  If you’ve been doing it for 5 years, what’s another 5 or 10?  You have to know yourself and trust your gut.  If you know that you’re susceptible to routine and comfort, and are unhappy with where you’re at.  Pick a day, and never look back.

#12: The Globe Trotter

Did you go to college in the same city you grew up in? Still living in grandmas basement? Do you even own a passport?

If you answered yes to any of these questions, well hot damn son, it’s time to go out and see the world!  My former boss once told me the best two years of his life were when he bought a VW van and spent 2 years traveling over Europe.

While I was in my first job, I’d never really had that cool travel experience, and you know what? I needed it. 

If your boss is significantly older than you, there’s a good chance that they’ve had this experience.  They’ve had some kind of cool travel story that they got out of their system, which has allowed them to settle into their current position.

If you haven’t had a similar experience (or even if you have, and are lusting for it again) tell your boss this when you’re submitting your resignation.  What are they going to say? “No, seeing the world is for schmucks.  You should stay right here in Scranton and never go anywhere. Ever.”

I don’t think so.

Common Objection: It’s dangerous out there, why would you want to leave a place as great as America?

Reality: Once you’ve seen the world you’ll have an entirely different perspective on Americans, as well as most aspects of your personal life.  Studying abroad should be an obligation in universities, and if you haven’t done this yet, you owe it to yourself to go outside the US. This is an easy excuse.  Just make sure you mail your boss a postcard.

#13: The Sandbagger

This final approach falls into the category of “use with caution”.

Don’t have the balls to actually resign on your own?  Well, you could always go the route of the sandbagger.  Stop meeting deadlines, stop being reliable, show up late – essentially stop trying.

I personally don’t think this is the best route to go.  However, when I polled Twitter I got a few people who took different variations of this route.  Exercise extreme caution when becoming the sandbagger, because it could tarnish your reputation and hurt your chances for future employment.

Common Objection: You’ve been completely slacking off and not doing anything! 

Reality: They’re right, your ass deserves to get fired. Bridge probably equals burned, but hey, at least you’re free of your job!

Moving Forward After Quitting Your Job

Hopefully, this post has provided you with some creative ideas for how you and your employer can part ways on good terms, or at least come to an agreement that is more beneficial for both of you.

As you’re preparing to make the leap, there’s definitely some recommended reading before jumping right in and peacing out:

Quitting your job is never easy.

Emotions will almost always be high, and even if you have something else lined up or a good business in place, the uncertainty can be brutal.

Stay positive. The worst case scenario almost never happens, and remember, you’re leaving for a reason. Even if things get temporarily more difficult, I promise they won’t stay that way forever.

Once you finally do it? Check out this post about what to do immediately after quitting your job.

What did I miss? How did you break it to your boss that you were heading elsewhere?

Sean Ogle

Sean Ogle is the Founder of Location Rebel where he has spent the last 12+ years teaching people how to build online businesses that give them the freedom to do more of the things they like to do in life. When he's not in the coffee shops of Portland, or the beaches of Bali, he's probably sneaking into some other high-class establishment where he most certainly doesn't belong.
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55 comments on "How to Quit Your Job Without Burning Bridges (13 Easy Strategies)"

  1. Darlene says:

    Hey Sean

    In 2009 I was getting remarried and had been doing a sale rep job for a company in New Zealand for almost 9 years. I was tired and was ready for something else. They paid well so that part was hard to give up. I set myself a deadline which was a month before my wedding and said I was going to leave then no matter what.

    I took the straight up approach. They knew I wasn’t happy and I wasn’t giving them 100% any more as my heart wasn’t in it as it used to be. So it was an easy conversation. They (bosses and co-workers) have become good friends as well so I certainly didn’t want any bridges burned or friendships lost. I said I wanted to travel and get back to running my own business which is what I did before I worked for them.

    So I quit, got married and spent 6 months traveling around Canada and the US in an RV with my husband and our two cats. Took the time to figure out what I wanted to do next which turns out to be teaching photography, back to my roots, and it really works for me and I’m excited about it.

    1. Sean says:

      Darlene, that’s awesome! Sounds like the whole transition was much easier for you than it often is – very good to hear.

  2. Darlene says:

    Well I’ve pretty much been an entrepreneur since 1991 so going into the job I sort of knew I wouldn’t do it forever. My nature is to be self employed, I just much prefer that freedom. Now I’m working towards doing it again, I work part-time at a camera store right now just for some steady income and get out of the house twice a week. Eventually I’ll leave here too and have a business that is mobile which is my goal now.

    1. Hi Darlene,

      Was there an opportunity for you to volunteer yourself for the next round of layoffs to collect severance and any deferred compensation?

      I just retired myself, but was able to negotiate a healthy severance package to kick back for a while.


      1. Darlene says:

        No technically I was a subcontracter and self-employed already as the company I “worked” for is in New Zealand and legally they can’t have “employees” outside the country. So no that wasn’t an option. They also generally don’t do lay offs anyway, I’ve never heard of them doing it in the 9 years I was with them.

  3. Ashley says:

    This was a fantastically timed article for me!

    The opening text from #1 is almost word-for-word what I’ve been saying for the past 6 months. I feel so loyal to my company because I know I’ve gotten some really great opportunities to do things I would never have been able to do without their support and trust. I feel awful leaving them. But I’m just not in it anymore, and I need time for me (I’m 3 years out of college) to figure out what it is I want to do, because I know this isn’t it.

    I’m putting my notice in today. This article has strengthened my resolve, and given me some ideas on how to shape my resignation. Thank you so much!

    1. Sean says:

      Good luck Ashley! Keep us posted how it goes, you sound like you are in an identical situation to where I was 🙂

    2. Ashley, pls try not to quit. 3 years at one place is a good amount of time, and depending on which state you work, you could get 3-4 months of salary as severance plus health insurance. Make sure you think things through.

      But whatever you do, good luck!

      1. Ashley says:

        “Quit” is a catchall for “I’m not going to be working here anymore.” I feel comfortable enough with my bosses to discuss what it really means for me to no longer be involved in the company.

        We’re small, and I’ve made it through -3- rounds of layoffs, including one that happened a mere 3 months after I first joined the company. In that first round, they actually eliminated my position, but created an entirely new one because they loved me so much.

        I have seriously leverage here, so I won’t simply say “see ya!” unless I know it’s my only chance to make a break for it. Ultimately, though, it is time for me to head out. How that departure shapes itself is yet to be determined. 🙂

    3. Stanley Lee says:

      Way to go Ashley. Good luck! It shouldn’t be that hard for your employer to find a replacement cog.

  4. Darlene says:

    Wow Ashley, you go girl we’re with you!

  5. There’s one thing I really encourage all of you to do, and that is: NEVER quit your job or get fired. Get laid off of instead.

    If you quit, you don’t get health care. You don’t get a severance package. And you don’t get unemployment benefits if you need it.

    One guy quit after 10 years only to find out his department got laid off a week later. They each got 2 weeks of severance per year worked, and one year of COBRA. Imagine leaving $60,000 on the table.

    Managers and HR want people to quit to save them money. But, we also want people to come to us and negotiate something because laying people off is hard.

    It’s the reason why I wrote the book, “How To Engineer Your Layoff: Make A Small Fortune By Saying Goodbye”. People don’t understand their own rights, and their ability to create a win-win scenario.



    1. Sean says:

      Really good points Sam, thanks for sharing. When applicable this can be the best route for both parties.

      1. It is VERY difficult to lay people off, mentally and legally. Who wants to lay someone off and hurt a person’s well being? Even if you hate the person and think s/he is an underperforming, you can’t just lay them off. It takes probably a year of documentation of underperformance BEFORE you can lay someone off. It takes time and is painful.

        It is often a godsend to have employees ask to see if they can work out a deal to get included in the next round of Reduction in Force (RIF). A lot of managers won’t be surprised b/c if you have the courage to ask, you probably have been wanting something to do for a while.

        The goal is to ask wisely.


  6. Jacob says:

    I was laid off a couple months after my colleague quit. I got 6 months of severance and 6 months of COBRA. My colleague got nothing and is stressed out!

  7. I went with #12 when I left my job of 11 years in 2010. Admittedly I did have another corporate job lined up, but my reason for leaving was the desire to spend time outside the US. I first told my manager verbally in a 1:1 meeting and followed up in email. I told him I’d been looking for expat roles for 3 years & hadn’t found anything suitable within the company, so I was moving on to expat roles with other companies.

    I made sure to give plenty of warning and keep things friendly. I ended up extending my notice period from 3 to 4 weeks to cover coworker vacations. Keeping that good will turned out to be a really worthwhile investment. When I ended up not liking my Manila job, I was able to return to my old company as a contractor based in Penang, Malaysia for 40% higher salary than when I was working in US full time. Pretty sweet deal 🙂

  8. Nick says:

    I used the “for someone else” method. My wife’s business is getting busy and I want to give her the opportunity to succeed to I resigned saying I needed to help with our family (we have an 18 month old). My work doesn’t need to know that I’m able to quit because of a lifestyle business.

  9. Chas says:

    Note on #3~ “breaking-up can be hard to do” but, sometimes your job leaves you. Sean, when you left your position, you had some money saved up- I think this is key for anyone. Also, there was a great article in Forbes recently that addressed this very issue and gave great tips on how to prepare for the leap, before diving off the cliff.~

  10. I’m a Timebomb Entrepreneur and very happy about in just less than 2 months since quitting. Leaving my job was very friendly and amicable, and I’m happy about that since I think that’s what both sides deserved.

    You hit all the ones I could think of, Sean, although I think “the Sandbagger” should be renamed “The Peter Gibbons” since it sounds like it’s right out of Office Space.

    1. Sean says:

      haha definitely agree – and YOU were the other Timebomb, I knew I’d talked to someone specifically about that…

  11. Jason says:

    I have had a high stress corporate sales job for the past 13 years(couple different companies) and had been building a business the entire time. The goal has always been to quit the day job to live life on my own terms. The challenge was every year I kept making more and more money and fell into the rat race trap. I tried resigning a year and a half ago and the company made me an offer to stick around. I got roped back into the day to day grind. It truly helped me though as I was able to make sure I was completely prepared for being independent and that a corporate career is something I really didn’t want. I’m about to be laid off which makes this transition that much easier. I wish I would have had the cojones much sooner! But I have to say that I’m so excited for this next chapter in my life.

    1. Nick says:

      Nice. Make sure you get the serverance package and all that comes with it on your way out the door.

  12. Andrew says:

    One thing to always keep in mind when quitting a job is this: The company you leave will be fine without you. I know it’s a simple thing, but many of us forget it in the heat of the moment. We start feeling bad for leaving a company who gave us a shot, and we anticipate the disappointment that will come from our coworkers, managers, etc. At the end of the day though, the company gave you a shot because they thought you’d be a good employee. They didn’t exactly do you a favor — it was really just a fair trade. And, what do you think they’d do if you weren’t performing up to their expectations? That’s right, they’d fire you. So if you’re unhappy working there, then you really owe it to yourself to leave. At the end of the day, life is short and you have to do what’s going to make you happy. I’m not saying that you’ll be easy to replace. All I’m saying is that companies lose senior level executives all the time, and still find a way to continue. Sure, your company will be disappointed that you left, but they’ll get over it and move on in no time.

    1. Sean says:

      I think thats a REALLY good thing to keep in mind, that we often overlook. It doesn’t matter what company it is, or the size of it, they will be just fine one way or another – and in many cases better off over the long term.

  13. Michael Ten says:

    If a job is not a good fit and it likely won’t change, then the best thing to do is to leave it, eventually, it seems.

  14. Zack says:

    Just did this yesterday.
    I’m not necessarily going Location Rebel or anything, but…

    I work in post production for commercials, TV, movies. I’ve been working in a small market for the last three years, with the dream of moving to LA to pursue bigger and better things. Yesterday, I used the TimeBomb logic, and my boss was at first speechless, but later appreciative and respected my aspirations, boldness, and respectfulness of the situation I was leaving him in. I plan to spend the next month helping my current employer find a replacement and training him or her into the position.

    I literally read this 10 minutes before I talked to him, and I’m glad! I gleaned a few last minute pieces of wisdom that I hadn’t thought of!

    1. Sean says:


      Sweet man! Glad you got some use out of it, and let me know how everything goes over the next couple months!


      1. Zack says:

        Flying out to LA at the end of this month to work on getting a job. Know any buddies that want a roommate for a week? 😉

  15. Mara says:

    You were spot on in your previous post when you said, “When the pain of staying is worse than the pain of leaving, it’s time to make a change.”

    I’ve been teaching now for 4 years and I feel that my season for teaching is ending. It’s been in my thoughts for more than a year with many sleepless nights – like a nagging itch that just wouldn’t go away.

    I’m working on the steps on becoming location independent. I’ve saved up almost 6 months of living expenses. Because I know that it won’t be enough, and my risk tolerance isn’t that high yet, I’ve set my time bomb to explode in 2 years.

    I know, kinda long…but it would enable me to save up for a year and a half’s worth of living expenses. That’s what the emotional-financial side of my brain can tolerate at this time.

    It was such a relief setting that time frame and reading this post today affirmed my decision on my impending exit.

    Also, a common aspect that I saw in several of your approaches was that the employee-employer relationship determines the ease of how one leaves a job.

    In addition to all that you’ve said, I feel that building a great employee-employer relationship from the very start is an approach that will contribute to an easier departure where both parties feel a sense of loss without the foul smells of a burning bridge.

    This post is very much appreciated. It was the encouragement I needed. Thank you.

  16. Sabine says:

    Thanks Sean for this list. I must confess I have used quite a few of theses approaches in my 15 years of working overseas…Quitting a job is indeed never easy and that’s why, just like you, I decided to create my own business so that I don’t have to quit another job… From experience, I would say that being honest at the moment of resigning has helped me, before moving on to my next country of residence…

    1. Sean says:

      Thanks Sabine! It’s always good to hear from other people how they approached it and learning about what worked and what didnt.

  17. Harrison says:

    I fortunately, got lucky to be “paid” to be let go with my last (and my only) corporate job.

    It was strange, because I was only into my new job 3 months and I got weird vibes from my team that would be very contradictory in terms of my performance reviews. Just wanted me out of the team, and didn’t even give me chance to voice my opinion on where I’d help the company. Their loss.

    In my mind, I wanted to tell them to *expletive off* (kind of like funny scenes in TV comedies), but yea … like your whole post is about not burning bridges. So I didn’t burn the bridge, but I sure as hell, won’t be crossing that bridge for long time.

    Good luck to you all who have quit, or are in process of leaving, or thinking of leaving your corporate job. It’s a roller coaster ride, but one that’ll hopefully be an eventful one.

    1. Sean says:

      I’ve talked to more and more people who have ended up getting “paid” to leave in various capacities, and it seems like there’s more and more opportunity to work the situation to make that happen for people.

      Also as much as you may not feel that way at the time, NOT burning bridges is almost always the best approach.

    2. That is what I’m talking about! Getting paid to quit your job is the way to go!

  18. Nice catalog of ideas! I recently left my job and used a couple of these tactics – Sean, you’re right that so much is dependent on what your relationship is like at the time with your boss. I knew my heart wasn’t 100% in my work anymore, and I wanted more flexibility to work from home and be around my kids (to have the ability for finger-painting and snack time in the afternoon, instead of corporate meetings, and then work from 9pm-12am, for example). But I also knew that the remote-work agreement wouldn’t fly, as a colleague had tried that approach and been turned down. Over the course of 6 months, I began quietly seeking out freelance opportunities with small non-profits, and received positive responses from several firms, enough to make me think that I could make a go of it. While my bosses were surprised to see me go, being able to say that I planned to freelance was great – there was a relief that I wasn’t going to work for a “competitor.” Also, co-workers were hugely supportive of me “getting out” of the corporate grind and living the dream of being more independent, which many of them dream about… The separation went so well that they kept me on a contract basis to manage a special project. Win-win for everyone.

  19. Andrew says:

    This is so irrational, but does anyone ever wish they were just fired? LOL — I know it’s irrational and doesn’t make much sense (since if you want to be fired, you can just quit immediately), but sometimes I wish I was fired. I’ve decided to stay at my job for the next 6-12 months, pay off some debt, save up some money, and learn some location independent skills. However, sometimes I wish I was fired because that might speed up the process by forcing me to sink-or-swim.

  20. Mathew says:

    Hi Sean! thanks for this post, it has been my first time on your site and now I guess I will be coming often, I think anyway you miss another good reason to quit, In my case I want to quit my job because is taking me 12 -14 hours a day and even though its a good salary for a single guy to party and have nice things, it’s not enough for a family man who wants to give the best to his wife and kid, that above all is my reason to quit, my kid is 6 months old now and I can keep thinking how to do the best move for him without jeopardize his well being. Thanks for your blog!

  21. Andrea says:

    I have asked my boss for a week off 9 months ahead of time, he is now telling me after I made all my payments that he is “unsure” if he can give me the time off because now recently someone else wants time off that same week and they have higher seniority over me. I’m a student and I can’t work full time around my school schedule. The other person that asked for time off is a different part of the business that I am. He had nothing to do with the work that I do so it shouldn’t matter if we went on break at the same time because we do two completely different things. My boss just came back from taking 3 weeks off over Christmas break. He claims that he doesn’t think he can give me my break because we are short on staff, yet he’s letting another girl go next week. I think it’s unfair and because he’s had such a warning that I should get this time off and with less than 2 months away he won’t give me a yes or no answer and said he won’t until probably the last minute. Serious BS. I am going to talk to him again next week and I want to try and keep my job but let him know that I will quit my job within the next 2 months if i dont get the time off. I’m losing money if I don’t go and honestly it’s just disrespectful the way he’s giving up my hopes.

  22. Michelle says:

    Andrea, my boss just made a similar move. What you have on your hands is an authority-abusing idiot. I work at a PR firm and my boss said he couldn’t let me take one random day in March off to attend my best friend’s wedding because he wasn’t sure if we would be busy that day. Mind you, there are 4 ppl who could cover for me and it’s never been an issue before, and we have nothing in our schedule for that month, much less the day I want off. He said he can let me know 2 weeks prior if I’m allowed to take that day off. I’ve been a manager and it would never occur to me to treat employees in such an idiotic way. I’m 36 and know better than to put up with assholes at this point in my life, so last week I put in my notice, since I have 12 months of living expenses and some solid job leads. Bosses like that never change and don’t deserve good employees. Since I gave notice, I’ve felt much more peace and calm and have been sleeping better.p

  23. Shannon Nix says:

    Thanks so much for the awesome info. If I need further assistance, can I email you?

  24. Irene says:

    Hey Sean that was a great article which has helped me decide what I wanted. To do since I was considering quitting my job and focusing on school. At first I felt my reason was it wasn’t flexible with my school schedule but now I realize it really cause my hearts not in it. 1hen I mentioned my school conflict they flat out said I can’t quit and now they wanna work it out with me.How do I let them know that I don’t want to stay when they’re so dependent on me?

  25. John says:


    I know this is an older article but nonetheless… I own a seasonal business and was offered a position of CFO with a company about an hour and a half from my home. I have two young children that require daycare and preschool…problem being my wife also works an hour away from home. After 4 months I am already burnt out from the commute and now that my 3 year old is ready for pre-school I do not have a feasible way to drop him off at 8am travel 1.5 hours away and then travel 1.5 hours away to pick him up by 4pm… I feel really bad but I think resigning at this point is necessary…… My wife has a pretty sweet job and gets paid awesome considering she doesn’t have a college degree…. …

    I know that when I put my notice in I will be offered increased flexibility….but at this point really do not want to burden myself or the company……

    #3 I am an Entrepreneur
    #4 Remote Work Agreement (been offered)
    #5 and #6 are playable but more 15-25k doesn’t move me…
    #7 In 4 months I have went from heart to not carring.
    #13 Sandbagger…True I really don’t care…

    Any thoughts on best ways to resign. This organization doesnt have an outlined expectation of executive staff in resignation… my thought is 60 days is reasonable..but 30 days is all that is necessary…. I am thinking 30 days with an extension of 15 days part time..this way I do not fall into a remote trap..

    Thanks for your suggestions!

  26. Leilah says:

    Really like you’re article. Need some help, my dilemma might sound somewhat vague, but I really don’t know how to go with it.
    I studied reservations and want to do that , my teacher got me this job, (the company had an opening, my teacher recommended me)saying I’d have to help around with some stuff dealing with reservations. Started out well, but not much busy, I feel like I’ll forget reservations if I stay here longer, cause sales and marketing is what I get involved in a lot more- a field I suck at and really don’t like, especially when I have go deep in to it writing sales emails and stuff.
    Its just been two and a half months and I’ve applied at the place I’ve wanted to work at- they had an opening, hopefully I get it. I’m wondering if I do get the job, what do i write in my resignation explaining to my boss my reason for leaving??

  27. Lauren says:

    Thank you for writing this all up! I’m definitely a #3 gal. I’ve been successfully making and selling art for a full year now, and making more per month than what I make with my current employer. I have anywhere from 50 to 100 order requests per month but as I only work on orders in my free time between work and sleep, the number I orders ican take per monn is sometimes barely 20….I only work on them 4 hours a day, 5 days a week, plus manage emails, inventory, packaging, etc. Its a massive amount of work for just one person to handle but it excited me, makes me feel alive, and it’s what I know I was born to do. I’m tired of hearing so many objections from outsiders who firmly believe “you’ll never make money as an artist, you need a “real job” to survive!!!” To which I say is utter bullshit. 🙂 I have made and sold all manner of artwork for 12 years now, all in my spare time, and never once have I not been successful at it. There were times when my ability to create and sell digital artwork at $5 a piece was the sole reason my fiancé and I had food in our stomachs!! To hell with anyone who believes there’s no money in art and that the corporate world is for everyone.

    It’s time for me to bite the bullet and have the scariest conversation with my boss, my boss who is a mere 4 years older than I am and is a multimillionaire. She is pretty kickass but the company is no longer a good fit for me. It’s been the wrong occupation for me for the entire year I’ve worked here. I took on some free schooling and this job as a means to provide for my fiancé and myself. It was a blessing at the time and allowed us to live without being homeless and hungry but now that time has come to move on and chase my lifelong dream. I am not afraid, I have every confidence in the world that I will succeed, and best of all I have the love and support of my entire family, my friends, and my respectable following of the most amazing folks who purchase and promote y chosen craft. I began my current art a year ago and although it was first met with objection and a bit of hate, I stood tall against it and pushed forward. I’ve never felt more passionate about it!!

    I am terrified of how the conversation will go, but my boss loves my art and I believe she knows this has been coming. Please keep your fingers crossed that they will be kind! I’m putting it out into the universe, hoping we can come to an agreement where they let me go so I can get my vacation time paid out and part ways on friendly terms.

    Apologies for the lengthy post, what you wrote above has only strengthened my resolve to do this. 🙂 Thank you!!!

  28. JAYNE says:

    since i started workin i jst wanted to leave…. i magine u do ur work but ur boss constantly give u a warning coz ur didnt do ur work….. am so fat up now tht im goin to quit coz they pay me 1200nad but dont appriciate me, tel me someone the company throws a staff party on a friday while u have to work the next day and tels u blow to test ur alcohol level….. fuck thts totally stupid . ………. i am upset am jst goin to quit!!!!!!!!!!!

  29. Ashley says:

    This article couldn’t have been more timely for me! Thanks for sharing all of these incredible helpful tips entrepreneurs like myself can use 🙂

  30. Ali says:

    Interesting advice. In a volatile economy, its suggested to foresee some of your apparent stuff before making the leap out of your current work place. You should have a backup plan in case your new hunt doesn’t work out or perhaps your startup fails.

  31. Edil says:

    Good day!

    I really need an advise.

    I just got a job i thought was a good one. Im only a month old employee and it’s my first job. Im employed as a sales engineer. The company seems not to be ready for me, as this assigned department for me had just started. Our main office is great, but im assigned in a branch office which is managed by a boring and “not so approachable” brother of the owner.

    What to do? Can i just resign and not bridge the contract?
    I cant really perform well with this undynamic work place and co-workers.


  32. Emily says:

    I left a post-college “space-filler” job after 8 months to pursue a job that I thought had the potential to become a career. The new job is related to my college degrees and it is with a non-profit, so it sounded perfect.

    I am coming up on 3 months at this new job and it is a nightmare. I am completely uncomfortable when in the office every day, my boss and I have trouble communicating, and the job description that I applied for and accepted is not what my job is now. I dread going to work every single day, and it has reached the point where I am so upset by my job on a daily basis to the extent that it is affecting the other parts of my life, such as interactions with friends and loved ones. We are a small non-profit, 5 full time employees plus our President/CEO. 2 of these full time employees are leaving in a couple weeks for other jobs and family reasons, so I feel really bad quitting now, which would be the organization losing approximately 60% of its workforce. However, I know I need to leave for many reasons, including for my emotional and mental health due to the stress of this job and boss.

    Does anyone have any recommendations or encouraging words?

    1. Ellen says:

      Emily, Quit Now! I’m 33 and I’ve never regretted quitting a job–only wished I’d done it sooner. Giving the news about your departure is the hardest part; once you’ve done that it’s all downhill. NO job is worth your mental health. The failure of that organization is the CEO’s responsibility, not yours. You will be so much happier when you’re out of there.

  33. J says:

    I’m at an odd point in my career, now. Work has become increasingly disorganized since a corporate takeover. I haven’t been content for 2 years. In June, I was beginning to consider looking elsewhere. Then I got seriously injured (not even subconsciously on purpose). Out 2 months on Workman’s Comp. Then had a small injury unrelated to said claim and this is hampering my ability to ease back in. I’m going on 4 months without meaningful work. It’s like the work’s not there, but if I really applied myself I would find it. It’s a battle to even consider going back in. I never thought it would get to this point. It’s like two flows of pressure- one for easing back in and one for easing out and I’m floating in neutral.

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