People Pleasing and Leaving Well: How to Prioritize Yourself 

Leaving a job is hard enough for those of us with healthy coping skills and boundaries. It can be a minefield of emotional navigation for folks with a history of people-pleasing. 

People-pleasing isn’t just being a “yes man” and volunteering for more than one’s fair share. It’s often based in long-seated trauma. You’ve probably heard of the “fight or flight” response, but there are two other possibilities when facing danger–freeze and fawn. 

The fawn response is something that happens when we learn to keep ourselves safe by becoming helpful to someone who might hurt us. Instead of standing up to a bully, we try to kill them with kindness. Instead of running for help, we change who we are and become social chameleons to avoid being ostracized. Instead of freezing in place and waiting until the danger has passed, we busy ourselves with other people’s responsibilities to please them. 

It’s exhausting, and people who have grown up mastering this kind of coping strategy often have a long road of recovery ahead of them to re-learn the basics of boundary setting and their own personal autonomy. 

What does people-pleasing have to do with Leaving Well? Everything. Because it’s very hard to make the decision to leave if you prioritize everyone else’s needs over your own. 

More Than Intuition: Knowing When It’s Time to Leave

Human intuition is an extremely powerful tool for decision making, but the decision to leave needs more than just intuition. In order to be as reliable as possible, your intuition must be shored up by the sturdy riverbanks of your boundaries and values. 

If you have a gut feeling about what you should do next but still feel a bit wobbly about the choice, this is an opportunity to check in with yourself. 

Reflect on Initial Commitments 

Start at the beginning. What outcomes were you hoping to achieve in this position or project? What were you brought in to do? Why did you accept the position? What did you commit to achieving? 

Once you’ve answered some of those questions, then the next step is to ask yourself whether you’ve accomplished those things. Did you have to pivot to other important initiatives? Did the project or role lose some of its importance? Is the effort complete? Did you accomplish your goals?

Try not to fall into judgment here. There are a thousand reasons that project priorities change over time. Maybe funding has dwindled or the initial folks in leadership have moved on from the organization. If you didn’t achieve the original goals, work on these reflections until you’re confident standing up for the work you did accomplish–and you’re not apologizing for pivots and changes in priority.

Reflect on Your Connection to the Work

Perhaps the question about leaving has arisen because you’ve lost your connection to the work. Ask yourself whether the project or role needs to be examined, pivoted, or picked up by someone else. 

If it needs to be picked up by someone else, how can you make the most of this current time to leave bread crumbs about the work that has been accomplished and what remains to be done, for whomever comes behind you?

In some cases, your decision to leave may become the natural end of the project or role. Especially for people-pleasers, this adds an extra layer of complexity, because you will likely have feelings that you’re abandoning your post, or that you’re quitting before it’s time. 

Reflect on the Team Impact 

Deciding to leave an organization, project, or role doesn’t just affect you. It affects the people you leave behind, and this can bring on some guilt and shame for people-pleasers who don’t want to make anyone feel bad or take on additional work because of their decision to leave. 

Whether these “Stayers” are the community you’ve served or colleagues that you’ve worked alongside during the project, leaving people behind is a difficult part of the decision to Leave Well. It’s one thing to say goodbye to a project or a role, but to also factor in the emotional case of having to also say goodbye to humans makes it exponentially difficult.
— Naomi Hattaway

It can also be incredibly challenging to navigate the leaving of a project or role when your decision impacts other people who are working in a cohort or committee. If possible, open up transparent, honest communication as soon as possible with the team during your leaving process. Share with them what you’re most proud of during your time of working together. Tell them what you will remember the most about your relationship with them. Ask them what they may need from you, before you go.

Protecting Your Energy When Leaving Well

Making the decision to leave can be exhausting, so I also want to encourage you to be mindful of your surroundings and current circumstances. Whether you realize it or not, the emotional and mental toll of leaving can lead you toward coping strategies that end up draining you instead of supporting you. 

Dr. Abbey Houde, known on Instagram as the Brain Health Doctor, is a functional neurology expert who introduced me to the concept of Energy Takers and Energy Givers. Take a look at the following lists–do you tend toward more energy takers or energy givers? Do you find a balance, or are your self-care behaviors a little out of whack? 

Allowing yourself to prioritize activities that give you back some energy can be very difficult for people-pleasers who have spent a lifetime deprioritizing their own needs in favor of others’. Even if it’s just a few minutes at a time, you can begin to practice more appropriate priorities by using this list and other mindful techniques. 
— Naomi Hattaway

Energy Takers

These activities and behaviors drain you of your energy and “spoons.” If you’re not familiar with “spoon theory,” consider yourself lucky–it’s a theory used to describe the ever-changing amount of physical and mental bandwidth that chronically ill folks have at their disposal on any given day. 

  • Focusing on the past

  • Inconsistent sleep

  • Mess and clutter in your physical environment

  • Social media distraction / over use

  • Dehydration

  • Screen time

  • Negativity

  • Junk food

  • The news

  • Alcohol / Sugar / anything your body doesn’t thrive on

Of course, none of these are inherently world-shattering. But if you notice a pattern that involves a lot of these energy takers, and fewer energy givers, you’d benefit from paying attention to that balance and making a conscious effort to seek more supportive self-care behaviors. 

Energy Givers

Energy giving activities replenish your mental and physical capacity. Again, start small–you don’t have to overhaul your entire coping strategy in a single day here. Start with easy steps, maybe a five or ten minute walk outside to get some fresh air and sunshine, or committing to a sleep routine that leaves you feeling rested in the morning instead of groggy because you stayed up for hours reading stressful news. 

  • Music

  • Nature

  • Resting

  • Sunlight

  • Hydration

  • Meditation

  • Movement

  • Decluttering

  • Sleep

  • Whole foods

Holding Your Boundaries While Leaving Well 

Let’s revisit the metaphor of riverbanks to represent boundaries and values. From your answers to the previous questions reflecting on your initial commitments, your connection to the work, and the impact on the team, what do those riverbanks look like in your imagination? When your values aren’t clear, you’ll find yourself straying from your boundaries, letting the water seep over the river banks–and you risk making bad decisions and impulsive choices, or letting the decision drag out too long.

Without firm boundaries around your Leaving Well plan, you might end up extending your notice, continuing your work on a freelance basis, or staying on “until we can find a new hire.” You do not have to do any of these things–even if they truly would help the organization. 

One way to keep your boundaries and intention to Leave Well front and center during your transition out of the organization is to weave your reflections from earlier into your conversations with colleagues and community members.

For example, I once ended a contractual relationship with a nonprofit. When I asked myself those reflective questions, I realized that the specific outcomes I committed to achieve were complete. I started weaving in comments like “Since the initial desired outcome was XYZ, and the team achieved that last quarter, I feel so proud to have been a contributor to that work,” or “Can you believe that two years ago, all of these deliverables were just a bunch of words on a white board? This team has accomplished so much.” 

These statements have a dual purpose: First, they establish that I had done my thinking about it and knew that my time with this project and organization was complete, on my own terms. It’s hard to argue with that, which is why it’s important to reflect first and know that your intuition is supported by strong evidence to support your boundaries. Secondly, notice the way I always directed the accomplishments back to the team as a whole. Our accomplishments were not just down to me, they were a team effort, and the team will continue to achieve their goals now that my part in the work is done. 

It’s hard to stand by your boundaries if you haven’t given them the thought they deserve! Spend time reflecting so that your gut instinct to leave is supported by firm evidence that your participation has come to an end. 

If you are struggling with a decision to leave, I encourage you to listen to season one of the Leaving Well Podcast, in which I interview individuals who made decisions to leave. It can be helpful to hear how other people made their choices to Leave Well, and how they prioritized their needs during the process. 

Additional Reflection Prompts

These questions can help you reflect on yourself and your needs outside of your job or career. Leaving can be a very emotionally difficult process, especially if you identify strongly with your career as part of your identity. Take some time to think or journal about these prompts. 

  • Who are you outside of your career?

  • What transitions have you made in the past?

  • How can you end things well?

  • How can you begin things well?

  • What do you know about what brings you joy?

  • What feels unavailable to you?

  • What would happen if you ask?

  • Where do you most need decision confidence?

  • What choices come with the most ease?

  • Where do you tend to shirk or abandon your leadership?

  • What are you letting get in your way?

  • What old ways of thinking about transition are you holding on to?

  • Where do you hold power or choice in how you navigate transition?


If you are an organizational leader, board member, or a curious staff member, take the Leaving Well Assessment to discover your organization's transition readiness archetype at  naomihataway.com/assessment.


To listen to an audio version of this article, tune in to Episode 45 of the Leaving Well Podcast: Self-Awareness and Boundaries.

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