It’s time to quit your job

Last summer I was tired of my job and struggling to understand why it was hard to leave. I am writing this article to share my experience, which will help you in reflecting on your own.

In August I was having one final work conversation with the Badger. I struggled with unrest at work and now seeing my good friend leave, I wanted to know when I was justified in doing the same. (If you don’t know who I am referring to, feel free to get more context about the Badger and my job search here. Needless to say, he was a coworker in the midst of moving to another company). I grew up with the mentality that contentment wasn’t a natural state. Was I just struggling with contentment? What does contentment even look like at work? He gave me this analogy:

A Horse walks into a bar and asks for a glass of scotch.

The bartender is amazed that he has met a talking horse, and after pouring his drink walks away to call his circus-owning friend.

Bartender ~“Do you want to hire a talking horse? I just met one!”

Friend ~ “Uhhh yeah! I would pay him $1000/day”

Taking another scotch over, the bartender says

Bartender ~ “Boy, do I have a deal for you. Would you be up for a new circus gig? It would pay $1000/day!”

Taken aback, the horse responds:

Horse ~ “Yeah maybe, but uhh…. why do you need a programmer in the circus?”

“You gotta want something.” The Badger concluded, “Are you going to get that here?”

The unrest I had faced was not due to a lack of contentment but was indicative of a bigger problem. I am currently looking to specialize in animation as a frontend engineer. This ambition was not being fostered. I was the horse being paid to do things that didn’t move me any closer to my personal goal.

My “something” was a desire to grow and specialize in my field. We all want something and our employment is taking us on a path. Where is that path leading you? If it’s in the wrong direction, then it is time to change jobs!

a concept I learned in The Slight Edge

Why is it important to want something?

Because inertia applies as much to our mind as it does to the physical world. Everyone wants meaningful work and most people theoretically agree with phrases like “easy choices, hard life; hard choices, easy life.” But where does this rubber hit the road for you?

Misconception: You have kids and they're in a good school district. You can’t just move and ruin their childhood, right?

Reality: Moving will be a growing experience if you support them through it. Don’t let the pervasive operating belief of “What doesn’t kill you makes you weaker” convince you otherwise. In reality, humans grow the most in hard times. Be careful! You could be robbing your kids of a growth opportunity while unconsciously modeling that “you must settle for a job you hate.”

Misconception: I have four weeks of vacation. I don’t want to risk the benefits I have and try something new.

Reality: That’s really generous of your employer to give you four weeks of your own life back. Humans work more efficiently when they have (adequate) rest anyways — don’t you want an employer who doesn’t act as if they are entitled to your time?

Your thoughts may differ, but likewise need to be examined for emotions that aren’t realistic or healthy, such as fear, apathy, and low self-worth.

I have found that returning to the questions of “what do I actually want?” and “does this job get me there?” gives me a much more centered approach to determining when to leave a job. It helps me block out my lizard brain (tendency to prioritize safety) and make a better decision.

I say these things to move you to action, not to make you wallow in your own situation or lust after someone else's. If you are not on track toward what you are after then don’t get discouraged — change.

When should you look for a job?

Do you “want something?”

Now that we have established that “wanting something” is the basis for making the job move decision, ask yourself: “what do I want?” Only you know whether your current situation is moving you toward that goal.

Ok, pause. A thought that just popped in your head about me being a delusional Millennial. Suspend it for just a second. What if you are a delusional Boomer? No, I am serious.

What do humans do when they are hurt? They put up walls, isolate, or hide. Don’t build a wall on yourself.

Most people hear that I am a Christian and think my faith is similar to a child believing in the tooth fairy. This is because faith and belief are often taken as equivalent. Faith is realizing what I don’t know, seeing what God has done in my past, seeing what he has revealed in scripture, and looking forward to what he will do in the future. Belief is some blind wish that good things will happen. It robs its victim of any sort of impact on their own situation.

You need to have some sort of faith in yourself. What if, instead of saying “this is me and this is what I will be,” you told yourself: “this is what I was and this is what I am going to be.”

You aren’t going to move up unless you can imagine yourself moving up. I had to picture myself as a programmer long before I ever was one technically. Now I am picturing myself as a freak with web animations and picturing myself making some delightful applications in the future. Have I done the reps before or walked that path yet? No. I haven’t. But I have walked other paths. God has brought me through them and I made it to the other side.

Similarly, you need to have faith enough to give yourself a chance to take risks and fail. Without this faith, it becomes impossible to stick it out and be creative in the face of numerous rejections.

Can you make it through the Dip?

So you’ve mustered up some faith in yourself? Just remember that starting things is fun and exciting and in the case of a job search it’s fun to change your status on Linkedin and come up with a new online persona that’s going to make you sellable. The distance between you and knowing how to job search well; however, really comes down to the hard work of applying and not getting any interviews. Before you get a job there will be a period like this where you will have to slog through. That period is called the Dip.

My adaption of a concept pioneered by Seth Godin

Sticking it out through the dip is what separates those who succeed and those who quit prematurely. Are you willing to put in the hours even when you are failing? Do you care enough to fail one way and try another, enough times to stick it out and get a better job?

This question is critical because if the answer is no, then you need to quit thinking about a job search now and work on being content where you are. Don’t false start and waste your time. If you can’t make it through the dip well or if getting what you want isn’t worth it to you then don’t try. Trying will only get you another crummy job or better yet will get you no prospects at all.

Some kid on Medium got a job at Google from one application, but don’t let his experience taint your reality. Getting a job is difficult. My job search took 250 hours. I had high expectations for what I wanted and I had to wait, try, wait some more, and try again before I finally got my “something.”

So what is stopping you?

Ok so you can make it through the dip and you have faith in yourself to get where you think you should be. Swyx describes people on the scale from “My Company is My Life” salaryman to “Stick it to The Man” ronin. If you are the ronin then hopefully I have convinced you, but in case you are not here are some questions I think will help you sort through the details.

1. I don’t know man, I have some great benefits?

I know you have X weeks of vacation and a good boss but circling back to the story of our good friend the horse; what am I here to do? Am I just working for X weeks of vacation and a good boss? No. I want to learn, so changing my environment is necessary. If you frame the decision in terms of what your “something” is, the decision becomes simpler.

Plus many companies have great benefits.

If you are prepared to wait out the dip, you can find your “something” without compromising great benefits.

2. What about all my unfinished work?

… get used to it.

18 I hated all my toil in which I toil under the sun, seeing that I must leave it to the man who will come after me, 19 and who knows whether he will be wise or a fool? Yet he will be master of all for which I toiled and used my wisdom under the sun. This also is vanity.

Ecclesiastes 2:18–19

Ecclesiastes is my favorite book in the bible. Solomon, one of the most wealthy and wise kings in all of history, examines his life and tries to find his meaning. His conclusion on work and career is that there is no end to our toil and like the grass, it will fade.

One of the things the Elephant (Aleksey Gurtovoy) taught me was that work is about the people you impact not the projects you work on. Keeping my priorities in this order helped me leave a project that was no longer taking me where I wanted to go.

On that note…

3. How do I leave all my work-friends?

If you have spent the time building those relationships, you can still maintain them once you leave. You can even use a calendar to make sure you do so! Remember, relationships aren’t unique. There will be new people and new relationships. I know friends are hard to make, but that has more to do with your lack of vulnerability (another way people are afraid to fail) than it has to do with anything else. Don’t let great relationships cheat you out of your “something.”

I hope this article was helpful to you. I don’t want to spark discontent in your life, but I do want you to examine and eliminate your apathy.

Remember the horse… 1000$/day sounds great, but he is more than just a talking horse. He is a programmer. What will you be?

Huge thanks to 🦡 Misha Bergal, the Badger. He is a great friend, had stories for every situation, and helped me to learn many values I hold strongly today.




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Joshua Wootonn

Joshua Wootonn

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