Stayer’s Guilt: Why Didn’t I End the Relationship, Leave That Job, or Make That Move Sooner?

When I work with people who have decided to make a major change in their relationships or careers, one of the most common themes I hear is regret about having waited until now:

“I knew things weren’t going well. Why didn’t I end it sooner?”
“I wasted so much time.”
“I could have been over this and moving on a year ago, but instead I stayed stuck.”
“All those years and nothing to show for it.”
“I lost x months/years of my life.”
“I knew in my heart it was time to go…but I stayed for years.”
“All my friends told me I should leave, but I didn’t listen.”
“If only…I just wish…Why couldn’t I have…”

Today I want to teach you a 6-step process that will help you banish the guilt and self-punishing and help you turn that “doomed” relationship or “dead-end” job into one of the best things that ever happened to you—even after the fact.

(Note—while I offer examples in terms of particular kinds of transition, you can use this process and apply these questions to any situation you feel you stayed in for too long—a relationship, an apartment, a job, a career, a city, etc.).

This is a process I developed for my private coaching clients, and it’s so juicy and impactful that I want you to have it!

If you’re ready to get rid of the guilt and find the gold, then get out your notebook and pen, roll up your sleeves, and dive on in.

1. Accept the choices you made as fact, recognize that you’re only human, and trust that it’s all unfolding perfectly.

Relationships don’t come with instruction manuals! And while some careers do, they aren’t clearly stamped with expiration dates (or even “best before” dates!).

It can be really hard to know when to walk away—and just as hard to summon the courage and conviction to leave once you do get that clarity.

When you start to beat yourself up for staying “too long,” try lessening the judgment and the emotional charge by shrugging your shoulders and saying (maybe even out loud):

  • “Yup, I’m human.”
  • “Yeah, it took me a while to see it/accept it.”
  • “Yup, it took a while to get up the courage to leave.”
  • “Yeah, it took me some time to figure it out.”
  • “Yeah, it took ____ for it to finally click into place.”

Our greatest growth and learning often ends up coming from situations that we deemed a mistake at one time. When you are ready to learn, your hardest relationship or worst job situation is ready to teach you.

The “wrong” relationship or job can be the very catalyst or key to put you on a path that is completely right.

If you’re willing to do the work of mining, there’s gold in that “wrong” place.

2.  Get crystal clear about why you now consider that to have been the “wrong” relationship/job/situation.

Taking the time to mine the relationship for what was wrong can help you get much closer to what’s right. 

Situations that don’t work for you are rich with information that you can use to create a happier, more fulfilling life now–one that does work for you.

Ask yourself:

  • What about this relationship/partner/job/home did some deep part of me reject?
  • Which of my values weren’t being honored or lived into in this situation?
  • What were the red flags?
  • What drove me crazy?
  • What buttons were pushed?
  • What parts of myself were hidden or unrealized?
  • What undesired behaviors or tendencies in myself were brought out or illuminated?

Get out a piece of paper or a journal and a pen, and actually take the time to list all of these things. Think of it as conducting research with a case study.

3. Identify and celebrate what you gained and the gifts you received by staying as long as you did.

It might sound counterintuitive to celebrate when you’re feeling down on a relationship or job.

However, you almost definitely gained some positive things in the time you stayed.

Don’t let yourself get away with labeling the whole relationship a waste.

No matter how “bad” it was, there are positive experiences you had that you would not have had otherwise, had you left sooner.

Ask yourself:

  • What did you gain by staying?
  • Who did you meet that you would not otherwise have met?
  • What positive experiences did you have that you would not otherwise have had?
  • What personal qualities did you develop?
  • What skills did you learn?
  • What did you learn about yourself?
  • What about the “wrong” are you grateful for?

This isn’t an argument for staying in a relationship or job you know is wrong for you. But since you did stay as long as you did, there’s value in gleaning the gifts.

Making a list of all the things you gained by sticking around longer helps you to snap out of your black-and-white thinking and allows you to see the gains as well as the losses.

Reflecting on what you gained can also get you out of victim mode–a powerful and crucial shift if you want to get in the driver’s seat of your life.

4. Identify the thoughts and beliefs that led you to stay.

Often, people who carry regret about not ending a relationship tell me they “knew” on some level, and for some time, that they “should” leave.

Specific thoughts and beliefs compelled them to stay. 

So: why did you stay? If you stuck around, you did it for a reason.

What thoughts are underneath your decision to stay?

Some common ones:

  • I’ll never find anyone better.
  • If I break up with him, no one else will want to be with me.
  • I’ll hurt her too much if I leave.
  • Other people will judge me if I mess this one up.
  • Leaving means I failed.
  • I’ve already invested so much—I don’t want to start over now.
  • If I can just make myself (smarter, more patient, less demanding, more into sex, less into sex, less myself, more someone else) this relationship will work.
  • It’s better to be with the wrong person than to be alone.
  • I’m too old to start again.

Which of these thoughts resonate with you? What’s missing from the list?

Make a list of all the beliefs and thoughts that kept you in the relationship or situation.

5. Get curious about those thoughts and beliefs.

These thoughts and belief can tell you exactly where your inner and outer work needs to be.

Looking over the thoughts and beliefs from step 3, ask yourself which of these thoughts are supporting you and which are holding you back.

Star the ones that hold the most limiting energy for you.

For each thought or belief, ask yourself:

  • How true is that thought or belief, really?
  • Where did that belief come from?
  • How is that belief limiting me or supporting me?
  • In what other areas of my life does that belief show up?
  • How might my life be different if I released that belief?

Take your time working through these questions, and give yourself the space and time to process what you discover.

6. Create a personal development plan based on your discoveries.

Now that you’re clear on what exactly was wrong for you in your last relationship, job, or other situation, what the gifts were, and the thoughts and beliefs that limited you, you can use that information and those thoughts and beliefs to make the map for your personal evolution.

Ask yourself:

  • How can I replace or turn around each toxic, limiting belief with a supportive, empowering thought or affirmation?
  • What beliefs am I ready to let go of?
  • What beliefs do I need more help or work to let go of?
  • What can I put into place to help me live into the more supportive beliefs?
  • What patterns did I notice that I want to change? What steps can I take to change them?
  • What aspects of the “wrong” do I actually want to keep with me and carry forward?
  • What qualities must exist in my next relationship/job that did not exist in the last one?
  • What do I plan to do with the awareness that I am gaining?
  • How will I use what I’ve discovered about my own buttons, patterns, and tendencies next time?
  • In what areas do I need to do some personal or professional development?
  • What resources and people do I need to help me with creating and following through on my plan?

If you need help, consider moving through these steps with the help of your therapist or coach.

By taking the time to explore your experience through this lens, you can turn your “wrong” into a golden opportunity to zoom in on the thoughts and beliefs that are likely holding you back in many areas of your life. Once you’ve done that, you can replace them once and for all with ones that will support you, and ultimately get you closer to finding your “right.”

Stayer’s Guilt, be gone! Awareness is power, and experience is your teacher. You may be closer than ever to that perfect fit.

So get going–and then come back and share your discoveries here!

Do you deal with “Stayer’s Guilt”? How do you handle it?


Are you ready to use your last “waste of time” relationship, job, or other situation to launch you into the life you want? I can help.

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2 thoughts on “Stayer’s Guilt: Why Didn’t I End the Relationship, Leave That Job, or Make That Move Sooner?”

  1. Point #3 reminds me of the power of gratitude to turn something negative into something positive. If you can think of one thing to be grateful for in a person you don’t like, you can change your response to that person. The same goes for a job, etc.

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