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.
In the three 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.
My goal with these was to make the departure as positive as possible for both parties, however there are a couple that may lead to hard feelings. Keep this in mind if going one of these routes.
Also as you’re preparing to make the leap, there’s definitely some recommended reading before jumping right in and peacing out:
- 6 Questions You Must Answer Before Quitting Your Job. Use this as a guide to figure out if you’re actually ready to leave your job.
- How to Get More Value and Enjoyment Out of Your Day Job. If you’ve answered the previous questions, and come to the conclusion, you aren’t quite ready yet, then use this post to ensure you’re still making the most of the time you have.
#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.
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 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:
- Your job is 80% “remotable”. Meaning, if given a computer and internet connection you can theoretically do your job from anywhere. Note: This could mean you’re making major changes to your routine, but if this rule holds true, there’s always ways to make it possible.
- You’re willing to leave sooner rather than later if it doesn’t work out. I pitched a remote agreement and it ended in “we will not accept your proposal, but we will accept this as your resignation” – be prepared for this response.
- You’re truly committed to working hard if the agreement is accepted. If you just want to use this as an excuse to slack off, don’t bother.
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 for a few weeks late last year, 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.
“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, WorkingRemote.ly.
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.
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
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.
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?
Featured Image: The Moderate Voice