Should I Stay or Should I Go?
- Jun 8
- 8 min read
Updated: Jun 25
Whether to stick with a job or pursue a new opportunity is both a perennial and universal dilemma. If you’re even reading this article something is already awry.
You now need to make the should I stay or should I go career decision emotionally, practically, and strategically for yourself and loved ones.
Sometimes staying holds us back and sometimes it's exactly what we need.
Making that decision can be a sensitive one laden with fears, hesitations, and what ifs. To nurture your intuition, here's a workflow that's usually only available to EverMore users, but we loved it so much, we wanted to share with everyone.
Want access to more resources like this and your own coach to reflect with you?
This decision-making framework covers:
Where’s your head at?
We’re going to assume you’re reading this because you’re trying to figure out whether to stay or leave your job. So, let's do an emotional inventory.
Are your feelings more of a stab or an ache?
An ache is daydreaming about leaving for greener pastures or feeling that you're missing something at work that matters to you (e.g., flexibility, money, autonomy).
At the beginning, an ache might not feel so bad, but it's death by a thousand cuts.
Being in a role or company that doesn’t mirror our values or needs can break the spirit over time.
A stab, on the other hand, feels acute. It could be a bad day that feels toxic, unexpected, or even like a betrayal (e.g., being lied to about growth).
Should the stab mean you’re not safe, please document it and let someone like your manager or HR representative know. Some wounds don't heal until you leave.
Reflect on:
When did the feeling start and when did you first notice it?
Did something acute happen or is it a pervasive feeling?
What is the thing you’re missing from your current role or company?
Is what you're feeling an expected pressure or stress of the role or industry?
A stab can dull into an ache and an ache can widen into a stab. But we recommend if this is the first stab to take even more care in processing.
Processing could look like going through this reflection more than once, calling a friend, or consuming music, film, or other media that grounds you.
Envision your ideal situation
Before the decision, pause to conjure up your dream life/work scenario.
Try to imagine all the bits and bobs of your day
Examples: What time you wake up, how you dress, if there’s a commute, the people you interact with, your mood, whether you’re in meetings, working with others or async, the time you have for family, friends, or hobbies.
Consider the environment as well
Examples: The company’s mission, emotional undercurrent, pace, compensation and promotion practices, culture (e.g., cooperative v. competitive), what it’s like to be sick or take time off, leadership’s mood and expectations.
Catalog what's happening in your current situation
How much of your ideal situation already exists in your day-to-day?
Sometimes we underestimate how much we’re getting positively from our work experience, and sometimes it’s the opposite, we underestimate how much work is harming us.
Try to answer the following questions with a gut response of yes or no.
The Essentials
Do you have a supportive manager or mentor advocating for you?
Does your compensation feel like a fair exchange for your talents?
Is the situation + environment conducive to the life you want?
Ideal Environment
Consider what motivates you—things like money, status, stability, balance, growth, relationships. Does your role or company provide those things?
Consider what’s most important to you in your career. Do you have it?
Are you being positively challenged by the work that you’re doing?
Identity
Do your friends and family feel that you’re content and yourself in this role?
Are you connected to the identity and purpose that comes with the role?
Do you have the mental energy and time for hobbies and non-work activities?
Are the things that aren't working or misaligned deal breakers?
What's your cataloging telling you?
Take some time to mull on what's working and not working with your current situation or consider an offer through the same lens of your ideal scenario.
There's no right formula for interpreting your yes/no answers. At face value, if you answered mostly “Yes”—it’s worth considering if staying makes sense. But, that needs to be balanced with how important each individual item is to you.
For all the things you said “No” to—Are those deal breakers? Another factor is whether the issues are more about your role or the company. It's much easier to adjust your role within a company you like, than the other way around.
If you’re thinking about staying...
What needs to change for you to feel good about staying?
Pinpoint what it would take to stay.
What needs to change in order to feel good about staying and who can you talk to about it? Change could look like increased compensation, crafting your ideal role, a different manager, and so on.
If those things don’t change, what will be the impact on your life?
What would be a signal or catalyst to push you to leave?
Deciding to stay, doesn’t mean you’re accepting this role “as is” forever. It’s just the best decision for you in this moment. That’s why that last question matters—give yourself a signal, so you’ll know when to revisit this reflection in the future.
If you're thinking about leaving...
The top consideration for most folks when considering leaving a role is about risk. For most people, it’s not tenable to leave without an exit plan.
That exit plan often looks like a new job, but it can also look like freelancing, starting a business, or hitting a savings goal that gives you some optionality.
Clarify your motivation and timeline
If you're running to something...
If you have an offer or new opportunity that you want to run to—why are you here?
Is there something in the essentials, environment, or identity that’s stopping you?
If something is holding you back, sit with that feeling to see what it's telling you.
When you feel drawn to something new, give yourself the benefit of trying.
Consider an offer through this lens:
If you have an offer and you’re not sure whether to accept it, try envisioning yourself in either role. Which version feels most like you?
Are you afraid to lose something from your current company temporarily or long-term? (Examples include bonus compensation, equity, generous benefits, sponsorship.) If this is the case, propose delaying the start date or try to negotiate them into the new offer.
Is there anything that’s happened in the past with a job that’s inflaming old wounds? For anyone who’s been let go, it’s reasonable that a job change could bring past fears or griefs to the forefront.
Are you feeling any hesitation that’s perhaps a natural or expected discomfort with starting something new?
Sometimes uncertainty is telling us something, and sometimes it’s just the friction of change and growth.
There’s a cultural tendency to interpret any friction, discomfort, or awkwardness as a lack of alignment. This isn’t to say you should abandon your instincts, but rather that the act of growth is filled with friction, discomfort, and awkwardness.
If you're running away from something...
Do you have a job offer already?
Starting a new role is always a little scary, but perhaps more so when you’re running away from something. If you have an offer and end up in a job that's for survival or a stepping stone—just be crisp about what the role currently is to you.
It's rare that a role or company is meant for us forever, but it's also easy to get stuck in the familiar. Keep rooting yourself in the idea of wanting and deserving more. Write it on a post-it, your planner, phone reminder, anywhere to check-in.
If you don't have an offer, do you know what you want to do next?
No: Pause to consider what you want because it could be available in your current role. Try talking to folks about their career or looping in your manager.
Yes: Beyond the process of finding a new job, start putting together some practical next steps, so that you have the optionality of leaving. Talk to your family or friends about the risks you’re able or willing to take as well as at what point a situation is too unhealthy.
If we’re in a role too long that doesn’t align with our soul or systematically destroys our self-worth, it can make us withdrawn, cynical, or resigned.
Getting Practical
The question of should I stay or should I go, usually means you’re going to leave eventually. It comes down to a matter of when. So, let's tackle the practicalities of leaving, which heavily influence our “when.”
Here are a some practical options:
Set a savings goal and map out how to build a financial safety net. In the meantime, get as much as you can from your role in learning and mentorship.
Consider bridging jobs by using your talents in freelance or contract work. If your company policies allow for it, you may even be able to test this first.
If you’re in a hostile work environment, document and report everything. If you resign for your own safety, you may still be eligible for unemployment benefits.
Push yourself to network—start by reconnecting with any former colleagues. Take 'em to coffee, let them know you're passively on the job market, ask for intros, and see what they need help with right now. Community whether 1:1 or through mingling events is one of the best ways to find something new.
Keep a happy file that captures all your wins and problems solved, so that you're ready to speak to your value casually or in an interview. You can do this in EverMore, where we even have a Tell Me About Yourself guide.
From an emotional standpoint:
You're the constant in your career.
The roles and companies will come and go, but you'll be the constant in all of it. As your career evolves, as you decide whether to stay or go, try to root yourself in the fact that your identity isn't tied to any role or company.
Make your decision the right one
It can be scary to take a career risk and it can be rash to assume a new job will be an easy fix. Often, we’re faced with the impossible task of trying to predict what we’ll regret more, while managing our own comfort with risk and the optionality that life has afforded us.
We only know the outcomes we pursue and experience. It's only in the decision we make that we experience regrets or to feel validated. There’s no perfect way to predict if you're going to have regrets or validation.
Be intentional in choosing to stay or go and make your decision the right choice.
Final thoughts
Nothing can replace your judgment, but we hope this choose your own adventure guide gave you the language and space to deeply reflect on your decision.
xoxo,
Courtney
Want access to more resources like this and your own coach to reflect with you?
