Should I Stay or Should I Go?

Jan 16, 2025

Questions, frameworks, steps, and a coin flip.

Once, a long time ago the Clash’s “Should I stay or should I go?” would start playing in my head as I took my seat at a weekly admin meeting. I took it as a sign. Not sure I read it correctly, but it was still a sign.


Are you staying or are you going?

Here’s the funny thing. We rarely put much effort into thinking about staying, but we get all fired up when we think about going. Yet they are both significant life decisions that can result in satisfaction or dissatisfaction. Makes one wonder if maybe flipping a coin is the better approach.

So …

Do you think about leaving your job?

How do you feel and think about the job that has perhaps defined your career and your sense of your professional self?

Are you uncertain or unsure about how to think about this, how to disentangle the emotions from what is happening now and what you want to have happen next?

What is your story? What do you want your story to be?

What are your next steps, resources, and supports for working through this?


Job therapy?

This “should I stay or should I go” is not uncommon among the clients that I work with and so I was intrigued by this author talk from McKinsey & Company with Tessa West, author of Job Therapy: Finding Work that Works for You.

West frames the relationship we have with our work, particularly when we have been in a job for a long time and have built up expertise and knowledge, as similar to any other long term relationship, such as a marriage or a friendship, where a variety of situations (she refers to five) can leave us with complicated feelings and unsure of what might be next without this relationship.

I have just finished the book and I appreciate how West offers a framework for getting curious about staying or going. I also have thoughts and questions for each of her five challenging situations that I offer as a caution against using the book as a sorting tool for staying or going.

  1. Crisis of Identity
    1. If a strong self-identification with the role, the profession, or the organization, is a barrier to our achieving what we want from work, what might this be pointing to for our own growth needs regardless of staying or going? How might we shift it into a healthy part of our job satisfaction?
  2. Drifted Apart
    1. If we, the role, the organization, or the world changes, we may find ourselves in a situation where we and the job have drifted apart. Given that we and everything around us is in constant change, what can we learn about riding the waves of change, rather than being sunk by them, regardless of staying or going?
  3. Stretched Too Thin
    1. If we are doing more, longer days, double and triple home, family, and work shifts, … and the coping strategies no longer apply or work, what will be different at another job? We need to take time (yes the time we don’t feel we have) to do the internal work, so that moving jobs isn’t a jumping from the pan into the fire or actually taking the same fire and unhelpful coping habits with us into the next job.
  4. Runner Up
    1. If we are experiencing barriers to moving up at our current organization, will moving jobs make a difference? Given the evidence of how poorly most organizations provide feedback, advisement, and career support, most likely we don’t know why we are a “runner up” and we run the risk of experiencing those barriers again.
  5. Under-Appreciated Star
    1. If we are not feeling valued will a different job make us feel different? Perhaps, but perhaps not. The story we tell ourselves of being under-appreciated is a tricky one and may have to do with our own unwise habits, views, and expectations on work and life than what is really happening, particularly if we are caught in a comparative mindset (see my post Fear of Missing Out Professionally). Or we may truly be an under-appreciated star. As always, it’s the work we do on the inside about our vision, values, and how we want to show up that will help us know the difference.


In my coaching practice I have worked with leaders on staying and I have worked with leaders on going. Either way, knowing why we want to stay or go and how we want to stay or go is key to making a wise, healthy, and good enough decision.

Why and how do you want to stay or go?

I’m here for you.

Babs


Too many P.S.s?


1. You can find out more about me and my coaching services at courageousleaders.ca.

2. This post is based on a LinkedIn post I wrote last November.

3. I was recently asked if I buy all the books I read. No I don’t. With much thanks to the Regina Public Library and the University of Regina Archer Library.

4. Image from Getty Images / Unsplash.


How about some extras?

“An Economist’s Rule for Making Tough Life Decisions”, Quartz

  • I am fascinated by chance and it’s less appealing cousin chaos (see my November 19th List and my thoughts on Brian Klaas’ Fluke – perhaps my favourite non-fiction read of 2024 that wasn’t about birds or birders), so a huge thanks to the reader who sent me this article which invites us to “flip a coin” and to “reclaim agency” when stuck on making a life change.
  • If you are overthinking and overanalyzing your “should I stay or should I go?” in the search for certainty (spoiler alert, there is none), skip the other reads in this post, grab a coin, and revel in this one.

The Journey of Leadership: How CEOs learn to lead from the inside out

  • While I follow and sometimes share the work of Mckinsey and Company, in general I find that their work on leadership tends to play it safe by trotting out the tried and true with a few tweaks here and there. There is nothing inherently wrong with the tried and true, until there is. 🙂 Yet this one did grab my attention. Why? Because we so desperately need to pay more attention to leading from the inside out. A bigger than self vision, well-being, self-awareness, self-regulation, equanimity, and ethics (my list, not theirs) is too often lacking in leadership and our organizations and communities are suffering for it.

Job Moves: 9 steps for making progress in your career

  • Similar to the above, first we need to know what makes us tick when we are considering a job move or our job path, then we can better assess the “pushes” (those things we don’t like about our current job) and the “pulls” (what we find appealing about a different job). I appreciate that the 9 steps are not about getting a dream job (please don’t trust anyone who is selling you that) but about setting a course for finding fit, understanding compromise, and moving from being a “puzzled job seeker” to a “satisfied job mover”. It also has cute illustrations to move the reading along.

Why work with me as your coach?

Because life and work is a demanding journey that requires attention and care.

I’ll help you expand and hone your self awareness and awareness of others, your expertise, and your wise and ethical behaviours while celebrating your resilience and courage for what is before you.

You can find out more about my work as a coach and facilitator at courageousleaders.ca.

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