Considering quitting? Ask yourself these 6 questions first

“I heard a Jeep fell on you,” I said.

“Now where did you hear that?”

A wry smile sent wrinkles across the face of my high school English teacher.

We were waiting for a show to start — Jersey Boys at the Tennessee Performing Arts Center. Seeing as it had been 10 years since I’d seen him, the Jeep question was the most interesting thing I could think of to say.

I glanced at my brother, trying to wordlessly confirm the story. Wide eyes told me that yes, something had happened, but no, I probably wasn’t supposed to talk about it.

After a long stare, my old professor chuckled.

“It didn’t fall on me. It ran over me. I was working on it in my driveway.”

“Weren’t those the first sick days you’d ever taken?” my sibling chimed in. (I think he was relieved we wouldn’t be sent to detention for asking.)

“Pretty much,” the teacher responded.


“Yeah. I had somewhere around 400 when I left the school.”

“Did they — ”

“Oh yeah … they paid them out.”

— — —

Dr. Jones wasn’t “renowned” in our small town high school. “Legendary” probably would have been the more accurate adjective. You likely learned about him the first day you stepped into the building.

I can’t even remember his first name. It only occurred to me a few sentences ago it isn’t “Doctor.”

Is it Bob? Fred? Larry?

Nothing sounds right. “Mister” might be it.

First-nameless Jones spent 48 years in the same job. 48 years. In a row. Contrast that with, over 40% of millennials who leave a position in less than 1/10th of that time. There are more options these days, sure, but I can’t help feeling we quit sometimes because there is nothing better to do.

I have quit a lot of things in my life — choir, golf, and a mime troupe (don’t ask). Other times people have quit me — friends, bosses, or iHeart Radio (that one you can ask about).

Once upon a time, big decisions were knee-jerk reactions. Now, I try and ask these six questions.

1. Did I do what I said I would do?

Recently my friend told me about the greatest compliment he had ever received.

On a call with his client, the person on the other end of the line struggled to find the words to describe Kyle’s performance. They couldn’t exactly put their finger on what he had done.

After a moment, they finally spit this out:

“It’s weird … you said what you were going to do. And then you just did it.”

I have started to believe integrity is the first, last, and only marker of success. Who cares whether or not you proclaimed a new years resolution? So long as you follow through on that decision. Who cares whether or not you started a business? So long as you made the choice.

Take your time to decide on your goals, but by the time the words come out of your mouth, by God you better be able to see them to fruition.

No matter the cost.

2. Have I been further than I’ve ever been?

Right now, my 59-year-old father is teaching himself how to build an app.

The program, designed for a very specific job role in a very specific field, is a product of his own creation. It does not exist anywhere else in the world. It will solve a problem for many.

(I’m telling you that part because I am sick of hearing people say things like “there are no more good ideas!”)

But what might happen if things don’t take off the way he thinks they should? If he read the market wrong or doesn’t figure out how to sell it or simply gets bored?

I asked. He said this:

“Well. I’ll have learned how to build an app.”

Nothing in life is wasted, so long as you extract the lessons. I love what Dave Ramsey says about growth:

“[Consistent growth] is the only difference between having 20 years of experience and having 1 year of experience 20 times.”

3. Is this becoming a pattern?

One bad trend popping up in this decade is a market I like to call “The Escape Industry.”

Culprits and key agitators of The Escape Industry include the dream mongers, those who urge others not to run to something, but from something.

  • Culture of your company a little off? Quit the job!
  • Significant other says you aren’t committed? Quit the relationship!
  • Facebook page not going viral after 2 weeks? Quit the effort!

I hate to say it, but my generation specifically is terrible about this. We want what we want NOW, and if we can’t get it, we will go elsewhere. This applies to stores, jobs, relationships, or our Netflix account.

It makes me sad.

At times, there are very good reasons to quit. But other times, serial surrender is a symptom of those who lack the courage or will to implement change where they are. They will bounce from job to job, idea to idea, person to person, never achieving the depth life has to offer in any arena.

I hope that isn’t you.

4. Am I going to be able to quit without regret?

If you can’t go without looking back, don’t quit.

There are obviously still issues to be resolved.

5. Have I executed this position to fulfillment?

Don’t tell anyone, but Dwayne Johnson is one of my favorite people.

Regardless of how you feel toward the work he does, how many other people do you know who have completely switched industries and were still able to make as deep an impact?

Excellence begets excellence. The Rock was not able to undergo such a radical shift in activity because he is lucky or blessed, but because he executed his wrestling career to fulfillment. He became the absolute best he could be before making the change. He went as far as he could go.

Then, with the leverage already provided from his commitment to the WWE, he leaped into a whole new world.

6. Have I asked the opinion of other people who matter in my life?

Whenever I’m struggling with a decision, I like to remember these words:

“Plans fail with no counsel, but with many counselors they succeed.”

My wife is a genius. Every time I make a dumb decision, it’s because I didn’t ask her thoughts. Sometimes, she affirms what I was already thinking. Other times, she tells me I am being an idiot. All times, I only have half the information for making my choice when I refuse to include her.

The solution for gaining the right answer on any decision typically looks something like this:

Time + Advice + Advice + Advice + Your Own Intent = Clarity
Notice that “emotion” does not appear anywhere in this equation. Emotion is fickle and fluid and all to often influenced by your level of hunger. Gathering advice, on the other hand neutralizes any misguided whim you might be feeling due to a lack of Larabars.

Do your diligence. Get the information you need.

Then, if you must, take the leap.

Much love,

— Todd B

Additional reading

Note: After 3 years of writing weekly on the Internet, I’ve found I become less and less tolerant to people who spit out what we must assume to be facts with no actual foundation.

The worst offenders of this are typically people like me — Motivators who are too busy “hustling” to dig deeply. In an attempt to offer further education or invite critique if I am misled in my thinking, here are the works which influenced this piece:

**By far the most entertaining source

This article first appeared on Medium.