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6 Simple Clues to Know When to Walk Away

Updated Dec 11, 2022

I once held the hand of a stranger who had just found out she was about to die. She was in her late 60s, diagnosed suddenly with terminal cancer and weeks to live. I was an awkward young seminarian, training to be a minister, and doing a mandatory hospital placement for chaplaincy. I was woefully unprepared for dealing with the heavy realities in that hospital. But I also happened to be the first person to stumble into her room after she’d had the news. She had no family, and I sat and listened as she wept about her regrets, all the things she’d never done.

I’ve never seen such great pain in my life. And it wasn’t the cancer. It wasn’t death. It was the feeling of wasted time that imprinted on my mind. She’d convinced herself that she still had time to do the things she wanted to. And then she didn’t.

It taught me something real about life that I’d only really seen on bumper stickers.

Life is too short.

And regret is terrifying.

We all know on some level how scary regret is. But this is actually part of the problem. The fear of regret causes a similar reaction in our brain to the actual pain of regret.

It’s ironic, because our brain tries to keep us safe, keep us from feeling regret, but in doing so keeps us in situations that will create regret in the long run. Your brain tells you that you’ll regret losing a paycheck, but it never tells you how much you’ll regret never chasing your dream.

Our fear of regret keeps us from knowing when to walk away from situations that are not good for us.

How do you know when to walk away? From a job you hate . . . From a career that’s not right . . . From an advanced degree that’s going nowhere . . .

How do you get past the objections of your very-normal, self-preserving brain? It screams at you:

You’re going to regret it!

Give it a bit more time!

What if you end up even more lost?

These fears are real and sometimes worth listening to. But you need a process to help you get past it.

For those of you who are stuck in a dead-end something, here’s how you know when to walk away. 

1. When it’s almost certain that there’s no future

Sometimes we get stuck in a role that feels like it’s probably a dead end. It’s almost certain there’s no future.

I say almost here because you’re never going to be really sure that there’s no future. And many of us stay in shitty situations for way too long because of that tiny hint of hope.

They’re going to see the good in me. I’m working so hard for them. Soon they’ll recognize me for what I do and reward me.

It’s going to change. They said they’re going to change—they promise they’re working on it.

People stay in the worst situations because of that sliver of hope that it will get better.

That job you hate has a tiny fraction of a possibility that you may get promoted.

In academia, it was the tiny slice of hope PhDs had of becoming a tenure-track professor.

In relationships, it’s that tiny sliver of hope that a person might change.

You will rarely be 100% certain that there will be no future. So, walk away when you’re 95% certain. Don’t let that tiny sliver of hope trap you and waste more of the most valuable resource you have, your time.

2. When you are not growing

There is one thing that I am certain of. When you are in a situation where you are not growing, it kills you inside. You get into a cycle of existing rather than improving. Growth is what makes us happy. Growth is what gives us the drive to keep moving.

If you are working for someone who micromanages you, who won’t give you new responsibilities, who likes to keep you in a little box and never give you anything that challenges you, that is a threat to your survival.

You are not growing.

I had a job. It was good money. It came with a pension and benefits.

But my brain was dying. I could get all my work done in two hours, and I sat there for five more hours every day doing nothing. I would beg my boss to give me more work, but there wasn’t any more to be done. We had more staff than we had work to do. I would make up things to do to keep me busy, doing extra work.

And I felt like this would be the rest of my life, doing two or three mind-numbing hours of work a day, and then continuing to waste my time. I wasn’t growing, and so I felt like I was dying.

Growth is vital.

3. When you have lost yourself

Have you ever lost yourself? It’s a scary thing. Whether you’ve lost yourself in a job, a degree, or even a bad relationship, the feeling hurts.

Maybe you don’t even know who the real you is anymore. Or maybe you never did. Some of us are masters at living the lie, pretending to fit into a life that’s not ours. Nobody on the outside could tell the difference, but when you go home at night and lie down on your pillow, there’s a deep feeling that this is not you.

If you feel lost, it might be time to walk away from what you’re doing. I say might. We all have bad days. But if you consistently feel that you don’t know who you are anymore, it’s time to figure it out. (Read How to Find Yourself Again – 6 Powerful Beliefs for Starting Over)

4. When you’re being held back

If you’re working for a boss who will never let you reach your potential. If you’re a PhD student trapped in an endless cycle of meaningless adjunct positions that never let you blossom into the powerhouse you were meant to be, it might be time to go.

You’ve got some great things to do, and if you can’t get them done because of people or situations crushing your spirit, sometimes it’s time. You’ll know when to walk away.

5. When you are being mistreated

Most of us have such an easy time looking at people who are in terrible relationships and recognizing what they need to do.

Have you ever heard yourself saying, “She needs to dump his sorry ass.” Or, “She’s not good to him.”?

It’s that thing. We see it in others.

But it’s so hard to see it in ourselves.

And in some ways, relationships are easier. We have a better threshold when it comes to relationships. We recognize mistreatment more.

I meet a lot of amazing people who are mistreated. They have so much potential, but they are talked down to, shoved into crappy positions that don’t pay well and keep them precarious. They’re given more work than any human should ever get and they’re paid as much as a McDonald’s worker to do it.

But they don’t walk away. They desperately want an employer to wake up and pay them what they’re worth. When I worked in a university, this was true of the adjunct teachers. They had a dream that someone would see the great teaching they’re doing, all the great support they’re giving to students, their cutting-edge research.

For most, that’s not going to come.

If you are being treated in a way that is emotionally, physically, or spiritually damaging to you, walk away.

6. When you don’t believe in it anymore

Most places where humans spend their time or form their identities have a constituting myth. These myths give our organizations purpose and give people a reason to fight for them.

We’re the best anthropology department in the U.S.

We’re the top hotel chain in the world, known for our quality.

Our graduates are better prepared for research than those from any other school.

We sell the best used cars in Manitoba.

If you devote your energy and years of your life to one of these places, it can be a scary moment when you realize that you don’t believe the myth anymore. Your identity is wrapped up in that myth. So is your sense of purpose and the direction you are taking in your life.

Walking away means losing a part of yourself. But, if you don’t believe it anymore, it might be time.

So, you’ve realized that it’s time to walk away. But how do you walk away? And when?

It might be time to walk away right now. Today. Quit everything, pick up your books, and walk away. Sometimes we need those drastic moments–especially if we’re being mistreated.

But, if you’re not going to quit today, flip your desk over and scream “I quit you shithead,” at your boss, or write a strongly-worded email, make a plan.

Walking away often requires a plan.

Figure out how and when you’re going to walk away.

And set a firm deadline. Don’t say to yourself, Someday I’m going to quit this shitty job. Say to yourself, I’m going to quit this shitty job by May of 2021, and build a plan for how you’re going to get there.

Just so you know, you’ll never have all your ducks in a row, so don’t wait for that moment. There’s a great metaphor Dave Ramsey always uses: You just need to get the boat a little closer to the dock before you jump.

Start moving. Start building connections on this side. Start your new thing now. Work on clarifying your vision, or finding it in the first place.

Putting a plan in place is the easiest way to counteract the fear of regret you’ll feel from taking a giant leap. It is the easiest way to silence those voices in your head that hold you back.

Here’s what you’ll find. Your destiny will be like a solar eclipse. Your new life will slowly overshadow your current life. It will take some time. But one day you will wake up and realize the reality you know today is no longer your reality, and you will be very okay with that.

You’ll step out of the place you don’t belong, and into one you do. And even if you flounder for a while, which you probably will, you’ll at least be growing and moving.  

And you won’t regret it.

Now Read: 8 Steps to Believing in Yourself When Nobody Else Does

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