Time to Quit Your Job: 3 Signs to Get to Know

How do you know when it is time to quit your job? There could be any number of factors at play other than work. How do you know it’s the job and not you?

Here are 3 critical signs to keep in mind.

Know When It Is Time to Quit Your Job

James Dickey was an advertising man in the late 1950’s—think Mad Men with less sex.

The position demanded a lot, and Dickey was always trying to steal time to work on his literary projects. “Every time I had a minute to spare, which was not often, I would stick a poem in the typewriter where I had been typing Coca-Cola ads,” he said.

Dickey kept his office door shut at all times. If a coworker knocked, he’d hastily clear his desk of poems and books.

As chronicled in Daily Rituals by Mason Currey, a colleague recalled Dickey’s efforts to steal time at the office:

If they said, “Alright, today we need ten television commercials and five radio commercials and two print ads; this is your assignment for the day,” he’d say, “OK.” He’d shut the door and within an hour he’d have it all done. Then he’d spend the rest of the time working on his own work—his correspondence, his poems. But of course they didn’t know that. They figured: “That’ll keep him busy all day.” But he was so smart and so fast, he could get it all done.

It’s possible Dickey was happy with his job. It’s possible he was happy hiding from his boss and his co-workers, working on his passion projects in secret. Many of those who advocate never quitting your day job might see it that way.

It’s just as possible that all that secrecy, all that subterfuge, wore down Dickey’s psyche and threatened to kill his passions.

Dickey was quoted as saying, “I was selling my soul to the devil all day … and trying to buy it back at night.” Thankfully, he did go on to produce his great works and show them to the world.

But he was eventually fired from that advertising job. He couldn’t navigate the balance anymore.

My hope for you is that you don’t let it get that far. That you listen to the pull of deferred dreams and unexplored interests before the hour gets too late.

Before you get fired like Dickey. Or worse.

How do you know when it’s time to quit your job?

Know When to Quit Your Job: The #1 Mistake People Make

According to Craig Ballantyne at Early to Rise, the short book The Richest Man in Town offers seven wealth secrets garnered from the richest person in 50 of the largest cities in the United States.

The seven secrets are:

1. Owning their own business (“stop working for the man as soon as you can,” they all said).

2. Working a lot (at least 60 hours per week).

3. Focusing on VALUE creation, not making money.

4. Focusing on unique talents and abilities and delegating everything else.

5. Partnering only with those who bring something critical to the table.

6. Getting addicted to ambition.

7. Persistence. Never giving up. In fact, most of them believe that persistence is the ONLY reason they have gotten farther ahead in life than other people. Not talent. Not luck. But simple persistence.

It’s a good list. We’ve covered many of these topics on Agile Lifestyle before. They all contribute living a life full of agility and purpose.

But let’s focus on #1 in that list for the moment.

According to another Early to Rise article, a survey of 1,500 of the wisest Americans identified the #1 mistake in life as staying in a job you dislike.

This research, conducted by Karl Pillemer of Cornell University for his book 30 Lessons for Living: Tried and True Advice from the Wisest Americans, revealed that these folks generally agreed with the following two statements:

“Staying in a job you dislike is a recipe for regret.“


“Spending 2,000 hours a year in a job you hate is a waste of your life.”

Agility requires we opt out of lifestyle choices we grow to hate. Staying in a job you dislike to please people you don’t care about is the path to burnout on the job.

But how do you know if it’s the job or if it’s you?

How Do You Know If You Are Unhappy in Work? 3 Signs

1. Good vs. Bad Organizations

In his tough-talking 2014 management book, The Hard Thing About Hard Things, respected Silicon Valley entrepreneur and venture capitalist Ben Horowitz expertly distinguishes working for good organizations versus working for bad ones:

In good organizations, people can focus on their work and have confidence that if they get their work done, good things will happen for both the company and them personally. It is a true pleasure to work in an organization such as this. Every person can wake up knowing that the work they do will be efficient, effective, and make a difference for the organization and themselves. These things make their jobs both motivating and fulfilling.

In a poor organization, on the other hand, people spend much of their time fighting organizational boundaries, infighting, and broken processes. They are not even clear on what their jobs are, so there is no way to know if they are getting the job done or not. In the miracle case that they work ridiculous hours and get the job done, they have no idea what it means for the company or their careers. To make it all much worse and rub salt in the wound, when they finally work up the courage to tell management how fucked-up their situation is, management denies there is a problem, then defends the status quo, then ignores the problem.

Are you working for a good organization or a poor one?

I’m sure one of these descriptions jumped out at you immediately.

If you’re working in a poor organization, it’s time to face up to reality: Things probably aren’t getting better for you. This is exactly the prospect I faced when I quit my job this past winter. In a bad organization, surfacing problems is seen as a disruption rather than an opportunity.

Your path is clear in this case.

But what if you’re working for a good organization and you still feel the tug of quitting?

Here’s where things get tricky. Ask yourself, Would you be happier in a different role in the same organization? The lure of job-hopping is strong, but the danger is you’ll end up exactly where you were before (minus a chunk change to moving costs, stock options, seniority, etc.). The politics can be difficult to navigate, but if you’re in a good organization, consider transferring to a different role or department before quitting outright.

And finally, if none of these options appeal, then it might be time to take the plunge and do what entrepreneurs do.

2. What Have You Actually Accomplished?

Time to Quit Your Job: Resume Thinking

Photo Credit: flazingo_photos via Compfight cc

In The Tom Peters Seminar: Crazy Times Call for Crazy Organizations, management guru Tom Peters calls on employees to use the ”fit-for resume” mindset to take a hard look at their career prospects.

Thinking in “fit-for-resume” terms means asking yourself the following questions:

1. What the hell do I do?

2. What have I actually done?

3. Who among my customers will testify to it?

4. What evidence is there that my skills are state of the art?

5. Who new do I know, far beyond the company’s walls, who will help me deal with an ever-chillier world?

6. Will my year-end resume look different from last year’s?

There’s an old story about the departure of an 18-year-veteran purchasing staffer from a company. “It’s a shame to lose all that experience,” one executive said to another. “We didn’t lose 18 years’ experience,” replied the second, “we lost one year’s experience repeated 17 times over.”

The world doesn’t owe you a living. If you can’t specifically describe how you made your organization a better place after each year, then you don’t deserve to keep your job.

There are millions of unemployed people out there who can do what you do, but better. Or maybe your position doesn’t need to exist at all.

“Given the reality of today’s entrepreneurial … economy, there are few jobs awaiting any of us out there,” career development expert Bill Charland states. “Instead, most good jobs today are co-created. Jobs are joint venture [with an employer] in problem solving. They’re strategies to solve pressing problems in organizations.”

It works like this: You get hired with a certain job description in mind, but this is really a guideline, not a hard-and-fast boundary. It’s your job to figure out what your job is, to find internal “clients” that you can serve and add value to the organization.

You prototype, learn, and adapt. Once you know what needs building, the organization expects you to take action.

Another way to spin this:

What 3 things can you learn specifically from each job? What can you learn next?

I wouldn’t necessarily tell your manager, especially if they’re the type who only wants you to do work they delegate to you.

But often the challenging, knotty problems of your organization that give you the most career and self-improvement benefits are exactly the ones they want you to tackle.

If you have enough courage.

3. Do You Have a Plan B?

Serial entrepreneur and author James Altucher advises coming up with a Plan B … and Plans C through J, just in case.

The problem isn’t that “Plan A” is a bad plan necessarily. It’s that it doesn’t work for the vast majority of people:

The “system” we were trained to grow up in (standardized tests, college, low-level jobs, own a home, have a family, owe more and more to the banks and the government, higher and higher level jobs, decent retirement account, retirement, some travel, death) works for a small percentage of people.

Many people try to make it work for them. Maybe 80% of people start off in the system. Maybe 5% of people remain in the system.

The rest of us are stabbed in our attempts to hang onto that final rung in the ladder. “If only”…”If only”….I can climb up one more rung in the ladder I’ll be safe. SAFE!

The reason we don’t come up with a Plan B (and C and D …) is the fear of failure. More precisely, the fear of being called a failure.

But as Altucher says, “It’s not a failure if you have to resort to Plan B. Or even Plan Z. You will be stronger, happier, the people around you will benefit, and society will benefit from having toughened you up for what you now deliver to it.”

Quitting your job isn’t the end of the journey. Believe me, I know.

As long as you’re willing to face the hardship, the struggles, the setbacks, Plan B (and C and D …) are the beginning to true independence and freedom.

Let your fellow agilists know in the comments:

When did you know when to quit your job? What were the signs?

Top Photo Credit: slworking2 via Compfight cc

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