8 Things You Need to Feel Relatively Okay Enough to Quit Your Job

If your job isn’t horrible, and you want to quit for hard-to-explain reasons, it’s pretty difficult to get to a level of 100 percent confidence. At its core, quitting means you believe there is something else out there for you – unknown, and as of yet, unseen.

It’s a leap of faith, a need for freedom, a little burning point in your chest that you can’t ignore any longer.

Getting to this point can take years. Or at least a really aggressive six months filled with a painful amount of introspection.

In my experience, you need a few minimum things to be comfortable enough to finally have the “I’m quitting” conversation with the boss.

this is a very accurate depiction of how I quit.
this is a very accurate depiction of how I quit.

1. Find a goal that you feel in your gut.

I’m not quitting just to sit around or go on cruises. That, I believe, is called retirement. Figure out what you want, and give yourself time to get it right. I went through about 15 different iterations of what I wanted over the course of two years before I finally figured out my goal at the bone-deep level.

Once you have the goal, focus on it, like a cat goes after a laser point. Be willing to run up and flip off walls for this thing. Some days will feel like it’s not possible. Stick with it.

start with a clear destination, then use Ways to route your path. unless you are independently wealthy, then you can wander and waste all the gas you want. but please don’t do that because it’s bad for the environment.
start with a clear destination, then use Ways to route your path. unless you are independently wealthy, then you can wander and waste all the gas you want. but please don’t do that because it’s bad for the environment.

2. You definitely need a timeline.

Assuming you don’t have unlimited funds, you need to set a time limit for trying to reach your goal, if you’re quitting your job fully.

I’m deadline-driven, so I’m setting a deadline of one year for seeing if and how I can meet my goal, rather than procrastinate and just travel around and visit 108 temples all over Asia.

Actually, that sounds heavenly.

BUT that will not get me to the point I want at the end of one year, and would just put me back in the position of needing to find a full-time job that treats me mildly okay.

3. You’ll want a budget.

I know, blerg.

BUT! What if we call it a SEXY budget (Halloween just passed, so I’m feeling inspired) and put Ryan Gosling on our budget spreadsheet?! Now this is motivation.

Cut out all the fat in the budget – be super honest about wants vs. needs, figure out the range of housing, food, transport. Be realistic and stay cat-laser-focused on that goal. Total up what you need against your timeline, and add a cushion for just in case this all falls apart.

Then start saving like crazy.

it’s okay, Ryan, I know numbers are hard. let’s do them together, that will make it better.
it’s okay, Ryan, I know numbers are hard. let’s do them together, that will make it better.

4. You’ll probably want a worst-case scenario.

This can function as both a comfort (you won’t live under a bridge, even a nice one) and an incentive to spur you on (you probably don’t really want to live in your friend’s unfinished basement).

So go through this exercise – if at the end of your timeline it doesn’t work out, and you can’t reach your goal, then what happens? You should have that cushion in your budget, so you’ll have a little money. Who can you live with, if you need to, while you apply to jobs in your previous or new field? Can you wait tables or work at a shop?

I’m not saying it’s ideal, but probably your worst-case scenario isn’t so bad. And you’d completely regret not taking this chance. And you’re awesome, so you’re not going to end up in that worst-case scenario anyway.

no way will your worst-case scenario be as bad as this day was for Alexander.
no way will your worst-case scenario be as bad as this day was for Alexander.

5. You’ll definitely need a support group.

As in, your friends, family, and other like-minded people. Whoever is supportive of your goal. Push those nay-sayers to the side for a while — they will not help you with your focus.

Talk to your supporters regularly. Buy them drinks and be liberal with hugs in exchange for support.

6. Lists!

With the amount of planning you’ll need to do to pull this off – if you can do this without a list, please let me know how.

Breaking big, scary things down into steps on a list makes quitting a job manageable. And then you can cross it off when you’re done with it, and doesn’t that feel amazing?! Put your end goal at the top of every list.

Admittedly, I love lists. I usually have a minimum of 4 sticky notes plus random other papers filled with lists on any given day, both at work and home. When I was around 10, I had a list of “places to go and things to do” on my wall. Something in staring at that list every day must have clicked in my brain, because 2+ decades later, I’ve visited and done almost everything on that list.

this is a list of things i love to make lists of.
this is a list of things i like to make lists of.

7. You’ll probably want to know at least one person toward your goal.

Before you quit, make sure you know at least one person in the field you are going into or in company you really want to work for. Probably you spoke to some such people when you were figuring out your goal. If not, now’s the time to find at least one.

I have a friend who really wanted to work in environmental resources for the state of Minnesota, and he went after that job with everything he had. He quit his just-okay job and just worked day and night being connected into the organization and applying to jobs and getting advice on applying to the jobs, until he got the position he wanted.

8. You’ll want a few intangibles too.

Stubbornness and flexibility. Stick to your goal and timeline, even when you’re inevitably told it’s not going to work. Recognize when you’ve got to shift and bend, and when you need to stay firm. Remember there are likely multiple routes to your goal.

A happy place. For the days when things go wrong, have a happy place to go to for a few minutes. This is mine. Or this. Both repeatedly if it’s a really bad day.

And maybe most important of all: Courage. The first step is the hardest. Nothing will stop your stomach from rolling over when you go to your boss and say “I’m quitting.”

But nothing will feel as free as the moment you’re out of the office after that conversation.

Seven weeks!

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