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When Should You Quit Your Job? Questions to Answer First

by Sean Ogle | Last Updated: July 22, 2019

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 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.
Build a Lifestyle Business Giving You Freedom You've Always Wanted

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