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Two Questions to Determine Whether to Stay or Go

Updated: Apr 10, 2022

Tucker Miller | President and Founder of Day 6 Leadership, LLC


Whether to stay or leave a job is a prevalent question for many. Millions left jobs in recent months in what is referred to as the mass resignation. This article offers some insight regarding what's on people's minds, how to decide whether to stay or go and how leaders can help support valued team members in deciding to stay.


Contemplating A move?

Forty years ago, the English punk rock band, The Clash, posed the quintessential question for these times with their epic song: “Should I Stay or Should I Go?” While the song wasn’t about work or careers, it could easily become the rallying cry for a generation of post-pandemic professionals who are voluntarily resigning in unprecedented numbers. The chorus of the song warns:

If I go, there will be trouble And if I stay it will be double

often It’s Hard to Leave.

Tendering your resignation is scary. Will people be mad at me for leaving? How will I live? Where should I go? Who will hire me? Will I be able to find a more satisfying position or discover my “right” livelihood?


And It May Be Harder to Stay.

If you feel yourself dying inside, you may think you have no choice but to save yourself and leave. In fact, whatever you're feeling, you're not alone. Today's workplace is stressful.

Here's just a brief snapshot of what employees are experiencing:


Stay or Go: How To Decide?

I do not wish for anyone to stay where they are if they are destined to suffer (and likely cause others around you to suffer). At the same time, it’s important to recognize that just jumping into something new may offer an escape, but it may not get you closer to your dreams. Distraction is not the goal. My hope for you is that you will decide between staying or going that honors what you want and I believe it’s possible regardless of whether you ultimately decide to stay or go. So, for those who wonder, here are a few thoughts on deciding whether it’s time to leave.


Note: the following suggestions do not apply if, by staying in your current position, you are at risk of physical or psychological injury. If you are at risk or unsure, seek out a professional or your organization’s HR or employee assistance program for additional help.


only you know the Answer.

With no disrespect to The Clash, when they sang: So you got to let me know, Should I stay or should I go?, I think the better line is this:

Should I say or should I go? Only you can know.

Certainly, you will talk with others, gather their viewpoints, seek out the support of those who depend on you, etc. While they offer feedback and perspective, the decision is ultimately yours to make.


This is about more than livelihood. Deciding whether to stay or go requires putting your heart, soul, and grit on the line.

In working with dozens of clients facing career decisions, I've discovered a few questions that help identify priorities and disrupt overwhelm and indecision.


TWO questions that will Help You Decide.

The two most clarifying questions I've found to help determine whether and when it's time to go are these:


#1 What regrets do I not want to have?

This question allows us to think broadly about new possibilities and challenges us to consider our vision, purpose, goals, and legacy. What are you here for? What do you want to achieve? Will it be where you are at or will it need to be somewhere else?


At the same time, the sneaky thing about how this question is worded – what regrets do I not want to have – is that it necessarily asks you to consider what regrets you will have if nothing changes. How satisfied are you with how things are? In particular, are you comfortable with the category of things inherent in your work situation that are outside of your control?


#2 Who do I want to hang out with?

The happiest people I know are the ones that have found their tribe. Work seems less like work when we love and learn from the people we are around. Who are the people that bring out the best in you? Do you work with people with whom you are proud to be associated? Those are the people that make up your tribe and as much as you are looking for them, they are looking for you. You deserve to be with people that are fun, engaging, caring, honest, smart.

There's No Rush.

Give yourself time to decide. Urgency can kill a dream and sever ties. When we feel rushed, we can make rash decisions from a place of discomfort just to stop the present pain, if only temporarily. Instead, slow down. Incubate a vision for your next, best step. Trust that options abound. You are right on time.


A Final Word for Leaders

As much as you might be thinking about your own career decision, take note that your team members are probably doing the same. Turnover costs are skyrocketing; companies are bleeding institutional knowledge; the majority of US companies report that it is easier to hire people than to retain them. The bottom-line impact associated with these turnover costs can be crippling. One mid-size company of approximately 7,000 employees calculates its annual turnover costs in the billions of dollars.

The most important question for leaders is not whether employees will decide to stay or go, but what will you offer to encourage employees to stay?

Over 90% of employees report that they would stay longer in their current roles if they had opportunities to explore career advancement or development of soft skills. Mentoring and coaching programs have been shown to make a difference in stemming turnover. More importantly, personalized coaching offers valued, high-potential leaders the opportunity to re-imagine and reinvent themselves as members of your team.






Day 6 Leadership, LLC is a consulting and coaching company specializing in helping to prepare women leaders for expanded responsibility, influence, and impact.


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Tucker Miller
Tucker Miller
Feb 01, 2022

Thanks, David. "Have I stayed too long?" is an excellent question -- it leads to inquiry into whether there are diminishing returns for the individual and/or the organization. Great add.

One of the things that I learned from you is that we will all leave our jobs sometime -- in one way or the other. Our opportunity is in finding ways to leave on our own terms. That insight has been a huge guiding light in work with clients and in making decisions about my own career. Thank you!

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Excellent information Tucker!

You helpfully frame the growing issue of turnover and changing jobs/careers, including the price exacted on individuals as well as organizations.


I think of one additional thing for individuals and organizations to candidly consider, especially related to emerging and established senior leaders. It is to address the question: “Have I stayed too long?” On this issue, are the organization and the individual leader on the same page or not?

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