I was terrified in the months leading up to the day I left my job.
I didn’t know what to do; I feared the uncertainty of it all, and I didn’t have much of a plan together.
Deep down, I knew I wanted to travel and run 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 or the best course of action.
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 covering six questions that cannot be compromised on.
You need solid answers to each of these if you want to be confident going into your job change. So, use this to assess 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 a while, both of those things will be in short supply.
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 and ate $1 street food daily.
Now, that doesn’t mean you have really go for it and move to SE Asia to get your business going, but chances are you will need to make a few sacrifices while building things up. Building a business is risky, so it’s something to be aware of.
How willing are you to sacrifice your paycheck for the unknown? What sounds more appealing right now is buying a new gaming system or VR headset (or another big ticket item) or spending your money and savings on living expenses to help you grow your business or support you while 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? What’s the cost of the essentials you need to get by while growing your business?
Once you’ve determined your risk tolerance, you need to figure out how many months of baseline expenses you need to save to feel confident about your decision. These expenses vary wildly based on where you live, current fixed costs, and social habits.
Again, this can depend on your risk tolerance. If you’re more risk-averse, you may want a full year of baseline expenses saved. If that’s the case, start planning now for how much you can save and when that means you can leave your job.
It’s stressful enough to start building a business. Having zero money in the bank at the start can make it even worse for a lot of people. So, I’d recommend having at least a few months of runway.
When calculating baseline expenses, make sure to factor in each of the following:
- Housing costs
- Any fixed expenses like a car note or student loans
- Utilities
- Cell phone
- Food and groceries
- Going out
- Health insurance
- Misc.
If you’re serious about setting and sticking to a baseline, I highly recommend setting up detailed budgets. Tools like Pocketguard, CoPilot Money, and You Need a Budget are all great. A simple spreadsheet can work, too.
Check out this post about budgeting, or read Ramit Sethi’s book, I Will Teach You To Be Rich, for more tips on getting started.
#3) What are you going to do when you quit?
It’s amazing 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.
- Do you have a business you want to pursue full-time? What are the short-term goals for it?
- Do you want to start a business? Is it something you can start before quitting your job? What’s the initial investment, and does that get in the way of your baseline buffer?
- Are you looking for a new job? Can you get recommendations from your current employer? Is there a way to leave without burning bridges?
In the first few weeks of leaving, it’s absolutely essential that you lay out healthy habits and routines. I know that World of Warcraft and re-watching The Bear 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:
- What are your new work hours? Yes, you have more flexibility, but you should have a base of rigidness to find your groove.
- When will you make time to exercise?
- Where will your primary workplace be?
- What specific actions will you be taking to find your work-life balance (i.e., Only golfing on the weekends, not having a drink before 7 pm, having two business-related zooms each week, etc.)
Remember that it’s also ok (or even great) to get a different or part-time job that still brings in some money and leaves you time to build your business. For instance, you may be able to snag a role working weekends and a couple of nights at your local library or big box store. Doing that takes some of the strain off your finances while still giving you plenty of time to work on your business.
#4) Is your decision based on emotion or necessity?
Why do you want to leave? Knowing the answer to this question is important, because if it isn’t for the right reasons, you may find yourself quitting, only to end up in a similar job two months later. After all, you hadn’t really considered why you were doing it.
- Is your working environment hostile?
- Are you getting closer to the goals you’ve set for yourself in this job?
- Are your reasons for leaving superficial or more deeply rooted in unhappiness?
Do your best not to make snap judgments.
Don’t quit just because you and your boss got into 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 regret the decision.
If you want to leave out of longer-term unhappiness and necessity, 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 who have been successful in doing what you’re striving for and those who 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 who 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, 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 about your ups and downs a couple of times a week.
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? How unhappy are you? Is that unhappiness in your job manifesting itself negatively in other aspects of your life?
If so, consider the other questions posed today and start planning your release date!
Once you have solid answers to these questions, you should know whether or not quitting is the right move for you.
This post was updated as of October 2024 for accuracy.
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.Join over 40,000 people who have taken our 6 part freelance writing course. Sign up below and let’s do this together.
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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.
I knew someone would come in and give a more scientific way to figure that out 🙂 Thanks!
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.
http://untemplater.com/business/quit-your-job-and-self-destruct-like-an-idiot/
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.
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.
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).
Cheers
Four Jandals Adventure Travel Blog
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?
Just wait until you need to generate Operating and Net Profits after expenses and taxes!
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!
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?
Sam
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!
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 🙂
Thanks,
Jason
Hey Sean, I’m paying attention this time. 🙂 I’ll let you know how it goes on the 2nd try; whenever I get there.
Sean,
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.
Well thats where the next project “Hacking the Highlife” comes into play 🙂
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! 🙂
Thanks again for mentioning Adaptu! We love how we are able to help people achieve their financial dreams.
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.
Sean,
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,
Mark
Sean,
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.
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!
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.
Sean,
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.
Great post – thanks Sean.
This is something i’ve been seriously contemplating and needed to find some answers and you’ve gave me some.
Oh yeah!
I quit, still 7 days before freedom. Freedom to do what I love and work online!!!
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. :/
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