The most difficult aspect of quitting your job isn’t figuring out what to do next. After all, you could go climb a mountain. Build out any number of 100 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 current employer that you plan to leave.
It doesn’t matter if you’ve been working with them for six months or six years — when you’re spending more time with them than your own family, it can be an agonizing endeavour 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.
Here, I cover five different approaches to leaving your job, the potential objections and 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.
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 six 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 realised 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 organisation.
2. The Entrepreneurial Pursuit
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. And 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. 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’re 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?”
3. The Remote Work Agreement
This can be a great approach, depending on a few key aspects:
- Your job is 80 per cent “removable.” 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 got this back: “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.
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, and open up a whole new client base due to your new location.
If you work for a small company in the U.S., they could even use you as their “international” office and make themselves seem like more of a global institution.
4. The Bluff
The bluff isn’t really a tactic for quitting, but rather understanding the importance of your place in the company.
Jennifer did this and didn’t even realise 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, 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 realised in that month just how valuable she was. So 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.
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, then you should probably stick around for a while longer or try a safer approach.
5. The Budget Cut
Ah, the dreaded budget cut. The re-org. The downsize. 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. That’s one less person they have to break bad news to, and that also means that you could be eligible for severance, or at the very least, unemployment benefits.
Approach this one delicately, as your boss could simply fire you (justly) on the spot. 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. Worst case is they fire you and you don’t get severance. Best case, you stay good friends, and get a head start on your new path.
Moving Forward After Quitting
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.
What did I miss? How did you break it to your boss that you were heading elsewhere?
A version of this post originally appeared on Location180.
Sean Ogle is currently doing the things that most people just talk about doing — travelling the world, building businesses and helping others doing the same thing via Location Rebel.
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