5 Most Important Things to Do Before You Quit

Written By: jeff

Posted On: July 25th, 2011

career break advice

Almost time to leave it behind. Copyright

If you’re contemplating a career break, the thrill of the upcoming adventure may be only matched by the anxiety of prepping for it. Before you can get on the road and start relaxing and rebalancing, there are lots of things to take care of, details about your life and your trip to get in order. The fun stuff is obviously the trip planning, buying your backpack, researching your destinations, reading travel blogs, connecting online with the travel community and, dare I say, figuring out your travel budget and getting an unlocked cell phone. Now that you’ve figured out that you can do it, that you can afford it, it’s time to quit your job. But, be sure to take this bit of career break advice: yes, there are lots of details to take care of before you leave. But…

I don’t want you to quit your job until you’ve gone through this list and do everything.


It’s simple. While it’s likely that you are going to be leaving on good terms, some bosses get weird when you tell them that you’re quitting. Even if you aren’t planning to burn any bridges before you leave (even if you secretly want to), you can’t predict how your boss will react. Even more, depending on your position within the organization, company policy may dictate that they ask you to leave immediately.

So, I want you to be prepared for the worst, even if it doesn’t come to pass.

The ¨Before-You-Quit-For-Your-Career Break¨ Checklist

1. Check your company’s leave policy. If you would like the option to go back to your employer, check its leave policy. You never know, there may be a policy that allows you to take extended paid or unpaid leave and still keep your job, maybe even your position. At a minimum, you’ll be well informed of what your company’s policies are before you talk to your boss.

2. Get your finances in order. There are lots of components to this. And, it may seem obvious. But, there are some things I don’t want you to forget.

  • Pay off your debt. OK, this is the most obvious one. But you don’t need to service a debt while you’re traveling and start over afterwards in the hole.
  • Get a Visa credit card. As much as I love American Express, the reality is that Visa is the most accepted card around the world. If you don’t have one (and I didn’t at the time I gave notice), go online and find one and apply while you still have a job and an income. Luckily, I applied before my last day on the job.
  • Think through your budget. You don’t have to have a detailed budget for your trip completed (in fact, it will likely change as you travel), but as I’ve written before, you can figure out if you have enough for your trip and how long it should last. And, if your meeting doesn’t go well with your boss, can you absorb the extra couple of weeks?
  • Create/Update your will. Maybe even create a trust. When it comes to traveling, I’m not a big proponent of over-planning. But, when it comes to your personal affairs, I believe you need to plan for the worst…just in case. In the unlikely event you don’t return, have all your affairs in order so no one left behind has to guess what you want done with your remaining assets.

3. Get your health in order. You’re still employed which means you likely get your health insurance through your employer. So, take advantage of that coverage to get yourself ready for your trip.

  • Get your checkups. Even if you get annual checkups, go ahead and get one more before you go.
  • Get your shots. Depending on your health coverage, the shots you need may be covered by your insurance. Some insurance plans won’t pay for travel shots, so keep your trip on the down low with your doctor. Another option. Finally, consider getting your shots on the road which will likely save you money if your insurance won’t cover them.
  • Spend your Flexible Spending Account (FSA). If you’re not working in the US, then you can ignore this one. But, if you are putting money away for your healthcare expenses, spend it BEFORE you quit. The day you are no longer employed is the day you can’t use this money anymore. Unless the rules have changed, you don’t have to have the claim filed by the time you leave your job. But, the expense must occur before your final employment date. Of course, check your FSA’s rules.
  • Investigate travel health insurance. There are lots of options so do your homework. But, go ahead and figure what you want and need before you leave. Most won’t start covering you until you leave the US
  • Stock up on extra meds, contacts, etc. as needed. If you have some special medical needs, go out now and stock up. Again, it’s a great use of your Flexible Spending Account. Of course, with more common meds, you might be able to get additional supplies on the road.

4. Update your resume and portfolio. You’re taking a career break because you have a career to break from. You have lots of accomplishments, important details that will make you attractive to your next employer after your break. So, take the time NOW, while they are fresh in your mind, to update your resume. If you have a portfolio, gather your work products while you still have easy access to them. You’ll be ready to hit the ground running when you get back. And, if you happen to get any solicitations while you’re traveling, you have something polished to send them.

5. Think through these scenarios with your boss. You’re going to talk to your boss about taking time off to travel. Maybe your goal is to negotiate your time off. Maybe you are going in simply to give your two-weeks notice. Whatever your plan, make sure you think through all the possible responses and have your answers ready. They might even be simply curious, so think about what you are prepared to share.

¨Hi boss, I want to take some extended time off to travel and take care of some personal things. Can I have the time off?¨ Possible responses:

  • No
  • Yes, but not now
  • Yes
  • Yes, and why don’t you go ahead and leave immediately

Finally don’t burn bridges…no matter how much you may want to or feel justified. Remember, this is your last impression you leave with your colleagues and employer. Make them happy to see you return to your career after you come back!

Let me know what you think and if you have any questions in the comments!

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7 Responses to “5 Most Important Things to Do Before You Quit”

  1. Great tips for a career break. For me, budget, finances, and even a will are the most solid ideas. I think it would be tough to leave a job right now because it may be incredibly hard to get it back. Hopefully, you could work things out so that you could come back after a period of time. However, the most important lesson in this is to think everything through and plan before you make the big decision.
    Jeremy Branham recently posted..Airlines increase the price of airfares as FAA taxes expire

  2. Natalie says:

    I like the one about not burning bridges. I made that mistake.
    Natalie recently posted..My Short-lived Membership of the Elite Turkish Housewives Club

  3. jeff says:

    @Jeremy, maybe a shorter career break, say a month, could be negotiated with your boss?
    @Natalie, I think a lot of people do it. It’s so tempting and when you are burned out and want to leave, it’s hard to think of a good reason not to burn that bridge.
    jeff recently posted..Lioness Overlooking the Veld in South Africa

  4. Before I took off for my career break, which was indefinite at the time. I had some serious shrink action. Believe me, it really helps. I actaully took off on my journey with no emotional baggage. It was weird hanging out with people who had it.

    New baggage enters your life, but when you finally head out the door, it helps to be cleared.
    Marina K. Villatoro recently posted..Picture This! Macaw’s in the Rain Forest Wild

  5. Marc Passion says:

    Great article. It’s how I operate. I work in mining so I smash out long stints saving and saving then once the contract it up – boom! I’m off. We’re lucky because in the camps are gyms, excellent chefs and of course its good money.

  6. [...] 5 Important Things To Do Before You Quit [...]

  7. Clark Vandeventer says:

    All great tips. I would add at least 1 more: be prepared for the possibility that nothing will go as planned.

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