meta_pixel
Tapesearch Logo
Log in
The Art of Accomplishment

Should I Stay or Should I Go? How to Commit Without Losing Yourself

The Art of Accomplishment

Brett Kistler

Management, Mental Health, Personal Development, Education, Self-improvement, Business, Health & Fitness

4.8269 Ratings

🗓️ 5 June 2026

⏱️ 34 minutes

🧾️ Download transcript

Summary

"Should I stay or should I go?" is one of the most common questions people bring to coaching, whether about a relationship, a job, or any major commitment. What if the hang-up is in the question itself? In this episode, Joe and Brett explore what's really being asked underneath the surface and why the path forward rarely lies in pros and cons lists. Together, they unpack two distinct versions of this question, the deeper fear that drives it, and what it actually looks like to commit to something without losing yourself in the process. Together, they explore: - The two types of people asking this question: chronic askers vs. those facing it for the first time - Why this question is really about enmeshment vs. self-abandonment - How childhood experiences of being asked to please a parent create fear of commitment - Doubt as the surface emotion - "Will I get more growth if I stay or if I leave?" when this is wisdom and when it's avoidance - Why idealizing the future (staying or leaving) keeps you stuck in the present - The Buckminster Fuller move: showing up uncompromisingly as yourself - The trap of "being yourself" with a chip on your shoulder - What real commitment actually means — and what it doesn't - Drawing boundaries without closing your heart

Transcript

Click on a timestamp to play from that location

0:00.0

When someone comes to you with a question, should I stay or should I go? What do you look for first?

0:08.6

Yeah. So usually that falls into two buckets, right? The first bucket is the person who's constantly

0:15.8

asking, should I stay or should I go, has been asking it through multiple relationships,

0:21.8

multiple jobs,

0:27.3

constantly in that question. And then the other one is somebody who's been in a relationship for a while and now they've come across this question. They've been in a job for a while,

0:30.9

and now they've come across the question. And so the first thing I look for is which of these two

0:36.5

are the case. Now, there's something that's very similar

0:39.3

about both of them, but there's stuff that's very different about both of them. And so that's,

0:44.8

that's what I first look for before we like look for any kind of resolution or how to get

0:49.3

to the other side of it. Great. So how do you look for that? How do you, how do you tell which of

0:52.8

these it is? I just ask them. Okay. So I come to you and I'm like, hey, I've been in this job for a while. I don't know if it's the right job. I feel like I should leave. Maybe if I'd lose all the benefits and the money and I don't know what I'd do otherwise. Yeah. Maybe I should stay.

1:11.0

It's safer.

1:12.4

Yeah.

1:12.7

So the first thing I find out is how long is this been happening?

1:17.6

Is this something that's been occurring over and over and over again?

1:20.4

And then with those folks, I try to understand what's the background that allowed that to

1:26.9

occur.

1:27.4

So typically, the way that that pattern works is somehow or another commitment felt really horrible.

1:35.3

Like commitment didn't feel good.

1:38.3

And typically what that means is that they were asked to be deeply ameshed in a relationship with a parent or a teacher or a

1:46.1

grandparent or something like that, where you can't be yourself, you have to do, you have to

1:51.0

bend yourself around me, please me, you know, whether that's through like excessive guilt or

...

Transcript will be available on the free plan in 27 days. Upgrade to see the full transcript now.

Disclaimer: The podcast and artwork embedded on this page are from Brett Kistler, and are the property of its owner and not affiliated with or endorsed by Tapesearch.

Generated transcripts are the property of Brett Kistler and are distributed freely under the Fair Use doctrine. Transcripts generated by Tapesearch are not guaranteed to be accurate.

Copyright © Tapesearch 2026.