When Should You Quit Your Job? Questions to Answer First

By Sean Ogle •  Updated: 07/22/19 •  9 min read

In the months leading up to the day where I left my job, I was terrified.  I didn’t know what I was going to do, I was fearing the uncertainty of it all, and I didn’t have much of a plan together.

I knew deep down that I wanted to travel and be running my own business. But I realized that simply knowing that wasn’t going to get me very far when it came to making one of the most difficult decisions of my life.

I spent the better part of a year in this job purgatory where I didn’t know what I truly wanted, and what the best course of action would be.

However, in the summer of 2009, I started putting together the pieces that would allow me to make one of the best decisions of my life: leaving my job to become a full-time entrepreneur.

So how do you go from clueless to confident when it comes to your career trajectory and employment situation?

Well for starters, you have to ask yourself some difficult questions.  You need to have detailed answers to them so that you can move forward knowing that you made the right decision for you.

Today we’re going to talk about 6 questions that cannot be compromised on.

You need to have solid answers to each of these if you want to be confident going into your job change. Use this as an assessment of where you’re currently at and where you want to be.

Nearly every day I’m asked “how do I know when it’s right to leave” well if you put serious consideration into the following, you’ll know when it’s right for you.

When Should You Quit Your Job?

#1) What is your true risk tolerance?

It’s easy to say you’re going to quit your job, start a business or travel the world – actually following through with it is a whole different story.  One of the biggest inhibitors to this is our propensity to seek comfort and security.  Even if it’s not a conscious realization, most of us crave both of those things.

If you quit your job, there’s a good chance that for awhile both of those things will be in short supply.

In order to start my business, I moved to Thailand, and while leading to 6 months of excitement and adventure, it wasn’t necessarily the most comfortable time of my life.  I lived in a $200 apartment with only the basic necessities to get by, and ate $1 street food every day.

How willing are you to sacrifice your paycheck for the unknown?  What sounds more appealing right now buying a new $1,000 TV (or another big ticket item) or spending your money and savings on living expenses to help you grow your business or support you while you’re waiting for a new job offer.

Be honest with yourself here. If your true risk tolerance isn’t as high as you think it is, the stress of quitting could be more harmful than the job itself.

#2) How much money do you need for baseline expenses over the next 6-12 months?

This is a good exercise to go through regardless of whether or not you want to leave your job.  What are your baseline expenses? This means, what’s the cost of the absolute essentials you need to get by for a period of time.

Once you’ve determined your risk tolerance, you need to figure out how many months of baseline expenses you need to have saved up in order to feel confident about your decision. These expenses will vary wildly based on where in the world you live, current fixed costs, and social habits.

When I left for Thailand, I assumed I’d be able to get by on about $1,000/month. I’d hoped to have 12 months of baseline expenses covered before leaving, but I wasn’t quite there.  When I left on my trip I had about $10k saved up.

Dan does a really good job here of outlying the baseline expenses for someone living in Bali.

When calculating baseline expenses, make sure to factor in each of the following:

If you’re serious about setting a baseline and sticking to it, I highly recommend setting up detailed budgets in Mint.com. I used Mint religiously when I left my job, and it helped give me the peace of mind that I wasn’t overspending.

Other options are also Adaptu, and if you’re looking to track business expenses check out Outright.

Check out this post about budgeting to help you too.

#3) What are you going to do when you quit?

It’s amazing to me how many people don’t have an answer to this question. Yes, your job may suck, but you know what’s even worse than that? Not getting paid and having nothing productive to work on.

Sure that might be great for a week, or even two, but then reality sets in.

If you’re going to quit your job it should be to focus on something better, not something stagnant.

In the first few weeks of leaving it’s absolutely essential that you layout healthy habits and routines. I know that World of Warcraft and Full House reruns are extremely appealing, but to say it’s a slippery slope is an understatement.

Here are some things to consider regarding your post-corporate life that you should have nailed down before you quit:

#4) Is your decision based on emotion or necessity?

Why do you want to leave?  Knowing the answer to this question is really important, because if it isn’t for the right reasons, you may find yourself quitting, only to end up in a similar job 2 months down the road because you hadn’t really considered why you were doing it.

Do your best not to make snap judgments.

Don’t quit just because you and your boss got in a fight, or because you couldn’t get the specific days off you wanted. Those are relatively superficial reasons, and if you’re acting on short term emotions, you may end up regretting the decision down the line.

That said, if you want to leave out of longer-term unhappiness and necessity, then start planning accordingly and craft an exit strategy.

#5) Do you have a support system in place?

This might be the most important consideration out of all of these.

Having a support system in place is absolutely vital to making a smooth transition into the next phase of your life.

Regardless of whether your goals are travel, entrepreneurship, or simply finding a new job, surround yourself and get to know both those that have been successful in doing what you’re striving for, but also those that are currently going through the same situation.

This allows you to have a group of people who can help mentor you through the transition, while also having people that can directly relate to you on a deeper level because they’re experiencing the same things simultaneously.

There are all sorts of ways to find this support system.

I started a blog and started forming my own group of people that would eventually give me the support I needed.

If you don’t want to put in the time and effort to do that, then find 3-5 blogs written by others and become a part of their community. The more active you are with comments and emails, the more you’ll get out of it.

Do you have close friends that are in a similar boat? Start a mastermind with them and chat a couple of times a week about your ups and downs.

You can also check out a community like Location Rebel, where everyone involved is deeply invested in making big things happen in their lives.

It’s been really inspiring to see so many people make such dramatic changes to their lives in just a matter of months.

#6) Is the pain of staying worse than the pain of leaving?

Quite simply, whenever anyone comes to me wanting to know when the right time to leave is, I tell them simply:

When the pain of staying is worse than the pain of leaving, it’s time to make a change.

Consider that.

How bad is it really? How unhappy are you? Is that unhappiness in your job, manifesting itself negatively in other aspects of your life?

If so, continue thinking about the other questions posed today and start planning for your release date!

Once you have solid answers to each of these questions, you should know whether or not quitting is the right move for you.

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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29 comments on "When Should You Quit Your Job? Questions to Answer First"

  1. Jeffrey says:

    I recently read an easy way to calculate what you need to earn to cover your basic living expenses. It was as simple as this: Take your monthly expenses (ideally already known using Mint or similar), multiply by 12 (months in a year). Add 25% for taxes then 10% for just rounding up, and you’ll have what gross income you need per year. Divide by 365 to figure out what you need to earn a day to make this possible.

    This is useful not just for escaping a job but figuring out what you need to earn in the long run to live the life you want.

    1. Sean says:

      I knew someone would come in and give a more scientific way to figure that out 🙂 Thanks!

  2. Knowing what TO DO after really is key. If there is no plan, then don’t quit. If there is no action, don’t quit.

    Living in America and subsisting isn’t that hard. There is always the option of moving home with the parents.

    Have you read this post on Untemplater yet Sean? “Quit Your Job And Die Alone”? It provides 4 examples of people who earn a good amount of money online, who still can’t do it. A couple hundred comments, b/c it’s true. Everybody could very well die alone if they quit their jobs and don’t plan things out.


    1. Sean says:

      Good post Sam – at the same time, I also think there’s something to be said for, if you don’t give it a shot, you’ll never know. I can think of just as many success stories as I can failures – but these are also very good things to keep in mind as you figure out if/when leaving is best for you.

      1. It is very true. If we never try, we will never know, which is why all of us who have that desire for entrepreneurship should definitely try and take the leap of faith!

        The only bad thing that will happen is failure, and a re-entry into the Borg! Just don’t take too many years to figure out the failure that’s all.

  3. Scary how timely information can be sent to your inbox… Am currently investigating the location independent lifestyle. Well actually more than investigating as currently looking in to when I will finish my current unhappy office job to pursue (what hopefully isn’t just my latest craze).
    Four Jandals Adventure Travel Blog

  4. Brad says:

    Great post! The one thing I find as the biggest challenge is to generate revenue. I know that other fields have very tangible products where sales and such are a pretty clear cut process. Mine on the other hand is more of a service-oriented area. I have thought of ebooks of course but wanted to branch out and diversify my offer of products to the public. Any insightful thoughts?

    1. Just wait until you need to generate Operating and Net Profits after expenses and taxes!

  5. Melissa says:

    Such a great post! I actually learned (perhaps the hard way?), that planning to quit your job without a day 1 after plan, doesn’t tend to work so great. I had money saved, but did not look into any of the other things you mentioned above – what my budget and expenses would be; what would my days look like; and most importantly, what came next.

    Sometimes it’s easier to focus on the “end date” that you forget the WHY behind quitting. I learned a ton during my first leap with a net or plan, but I think most people would find it nerve-racking and perhaps plain stupid. My plan was a non-plan, which created a lot more anxiety, especially around money and filling my time, than perhaps a majority of the things from my actual job-job.

    Great questions to ask, and even better advice!

    1. Melissa,

      Even though you learned “the hard way”, it’s still not that bad right? It doesn’t seem like it takes much to survive and be happy in America. Whatcha think?


      1. Melissa says:

        Sam – Honestly, was the best thing I have ever done. I learned more than I ever could have imagined, if I had planned everything out perfectly. And it better prepared me for the next step – I just needed a mini-in-between before I transitioned fully. Definitely didn’t take nearly as much to survive and be happy, as I thought it would. But it did help me better understand and allocate my expenses and examine how I dealt with money, in order to prioritize. All good things in the long-run!

  6. Jason Martin says:

    Great post Sean.

    These are all important factors to consider before quitting a career and taking your life in a new direction. Definitely food for thought 🙂



  7. Hey Sean, I’m paying attention this time. 🙂 I’ll let you know how it goes on the 2nd try; whenever I get there.

  8. Chas says:

    Thanks for bringing the reality of making this move back down to earth. A $200 a month apartment and $1.00 a day street food isn’t the vision most people have of becoming a ‘Location Rebel’. It is usually a picture of laying in a hammock watching a tropical sunset, while sucking some exotic drink out of a coconut.

    1. Sean says:

      Well thats where the next project “Hacking the Highlife” comes into play 🙂

  9. Emma Brooke says:

    Thank you for this! I’ve been planning and saving for a while but like you and the others said, you have to know what you’re going to do afterwards that’s the biggy for me. I have a plan, but I need to be honest with myself and really nail down the details…that said, I have to be flexible enough to know it’s highly likely to go t*&ts up anyway but that’s half the fun! 🙂

  10. Thanks again for mentioning Adaptu! We love how we are able to help people achieve their financial dreams.

  11. Ben Holt says:

    Great post, Sean. As I’ve learned, not having a job is quite a lot of work. I quit mine last year to take up blogging full-time. It’s been more “work” than ever, but it hardly feels like it.

    The benefit, as you likely know, is that you can do the work that you love and that builds your own platform and wealth.

  12. Mark says:


    This is what I pay attention to your site for. I LOVE this sort of well thought out, practical advice that makes making the move so much more doable. Whimsical idealism can be nice in (very) small portions, but knowing that you were able to spend so little on rent and food brings it into perspective. I’m in the process of eliminating the distractions that are keeping me from starting my music mixing business, which will let me put my time first.

    Your formerly cynical ass-hat,


  13. Fin says:


    Nice timing on the post. I’m leaving my job in 2 weeks. My company is downsizing and I was the last one in. I’m not to fussed though. I’ve got about 12 months runway and a ton of ideas.

    I’m going to concentrate on 3 blogs, but one main one which I’m planning to start as soon as I leave.

    I don’t have support. My family think I’m mad, but then they don’t understand how anyone can make money on the Internet, even though I’ve made a few thousand.

    I don’t hate my job, in fact it’s OK. The truth is, I know what life I want so now is the perfect time to work at it. I’d love to go to Thailand, and I did toy with the idea, but for now I’m quite happy to stay at home in my room and work 16 hours every day until I’m making money, then I’ll be straight on a plane to Asia.

    I’ve been preparing myself for my “new” job. I’ve bought a nice expensive leather chair, a comfy dressing gown and a big pair of monster feet slippers. Life’s never gonna be so good, lol.

    Nice post.

    1. Ben Holt says:

      Hey Fin – you seem like you’re in about the same place as me and, like me, it seems you’re prepared to work your tail of. Best of luck to you!

  14. Luke says:

    This post really brings some reality to the Location Rebel idea. It sounds good to quit a job you don’t enjoy and move off to find a new career and an advenerous lifestyle; however, as this post highlights there was more to it than that. There was a significant savings. That savings may be easer to come by for a financial analyst than it is for a blue collar worker who work 3-4 jobs to almost pay the bills.

  15. Brandon says:

    Thanks for the very considerate post. The thing that stuck out most to me was the very last piece, “Is the pain of staying worse than the pain of leaving?” Said in a positive light, “leave when the call from within is so strong that you can no longer deny it.” I left my job about 2 years ago with a decent chunk of savings and a bit of consulting work to bring in some money. I primarily focused on traveling very inexpensively and trading work for places to stay and food. I definitely did not have a plan, and I’m really glad about that. The last two years have been an adventure beyond what I could have imagined. I’ve been all over Europe, China, India, Bali, Thailand and Cambodia. It’s been a beautiful experience primarily, I believe, because I was following a deep call from within – a call that said, “It’s time to go even though you have no idea what’s next.” Listening to that call has been the best decision I’ve ever made.

  16. Jamie says:

    Great post – thanks Sean.

    This is something i’ve been seriously contemplating and needed to find some answers and you’ve gave me some.

  17. Daniele says:

    Oh yeah!
    I quit, still 7 days before freedom. Freedom to do what I love and work online!!!

  18. andy says:

    I want to quit because all I do is create systems that make money. I could just create those systems for myself, couldn’t I?

    I’m a bit confused… My job actually consists on that, and I do like 99% of the work on each project. I also have savings to live 4 years with no income.

    On the other hand, my job provides no bonuses and I haven’t had a single day of vacation in the last 2 years.

    It’s a high paid job though, and I guess that is what makes the decision hard. :/

  19. Rahul Kapoor says:

    I’m from India, just started on my first job about 4 months back. I am really struggling here, the office set-up is quite small, and there’s not a single colleague of my age that I can talk to or discuss anything with. In fact, the people i work with are almost 25-30 years elder to me, so there’s a huge generation and communication gap.
    I joined this company because i thought I’d be learning good stuff here, the profile seemed good. But I really haven’t learnt anything substantial here till now. There are days when I literally have almost no work, and without anyone to talk to, it is pretty much unbearable.
    Also, my boss is a jerk. I respect his dedication and his skills etc. But the fact that it’s my first job, and that NO formal training has been provided to me related to how to work in a particular manner (be it answering mails or preparing presentations etc) does not concern him at all. Rather, he takes jibes at me for not being able to work as expected and how i am just adding to his stress level.
    This job is also affecting my life a lot. I broke up with my girlfriend because she had an amazing job, and couldn’t/didn’t appreciate what I was going through.
    The only thing is, I do not have anything solid planned for the future. I am in talks with a few alumni and friends in other companies, and have a few interviews lined up. I know I want to work, but I do not have a job in hand right away.
    I read your blog on ‘How to quit without burning bridges’, and it helped me a lot.
    Please suggest whether I should reconsider my decision to quit, just because I don’t have another job lined up ?
    All suggestions are welcome.
    Thank you

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