Should I Stay or Should I Go: How to Know Whether to Leave Your Job & If So When

Posted on May 15, 2024 by Brandon Whittaker, One of Thousands of Executive Coaches on Noomii.

I have received a lot of questions lately about how to decide whether to leave one’s job or to stay. This article should give you some tools to figure out what your options are and to determine whether those options would be “better” or “worse” than remaining where you are. Given the enormity of this topic, I haven’t discussed in detail changing roles and/or geographies within one’s current company, nor have I directly covered deciding whether to attend grad school or start a business. That said, the tools here should be able to help you make those decisions as well.

Here are the steps I’d encourage you to go through when deciding whether to stay or go.

1. Take stock of where you are. Being aware of your progress toward realizing your long-term goals is important, as it helps you plan next steps accordingly. Doing this exercise also helps you to acknowledge the progress you’ve made and to leverage the confidence and knowledge gained to achieve future goals.

2. Know what your values are. There are many jobs that you could do well if you put forth sufficient effort, so why not focus on doing the one that’s best for you right now? Deciding what job that is depends on what’s most important for you, which at a high level will be determined by what you value. Skipping this step means potentially doing a job that is incongruent with who you are as a person and/or who you want to become, which can cause issues in the long run.

3. Know your options. Before thinking seriously about leaving your current job, know what your alternatives are. You may want out of your current situation only to find that it’s actually the best fit for you given where you are in your life. Conversely, your dream job may be hidden in a corner of reality you’re unaware of because you haven’t explored thoroughly enough. Identifying and evaluating your options periodically can help ensure that you are in the role most suited to you.

4. Narrow things down. It’s important to develop a systematic way to zero in on the job prospect that is best for you. I offer a way for you to do so.

5. Make a decision. Ultimately, deciding whether to make a move requires some subjectivity. I provide some thoughts below about how to leverage that subjectivity for your benefit while being informed by a more objective standard.

6. Other things to consider. Whether you stay at your current job or take another path, there are a number of things to consider, including how to “leave well” if you decide to make a change and how to “stay well” too.

Take stock of where you are

Before you decide whether to change jobs, do an inventory check. Reflecting on your career journey can help you get clear about where you want to go next and whether you have the skills, experience and capacity to move forward. Here are a few questions you should ask yourself:

- How have you grown as a professional in your current role?
- What knowledge have you acquired about yourself through your work?
- How happy are you with how your life is going generally?
- Do you have concrete values-based work-related goals? If so, are you on track to meet them or not? If not, what has gotten in your way, and what is your plan to get back on track?
- What do you have to be thankful for about your current work situation?

This is not a time to beat yourself up if you don’t measure up to your expectations. While it’s important to address the goals you haven’t reached, this exercise is more about acknowledging where you are and what you’ve achieved and knowing where you have gaps. It is also meant to help you remember what all of the work is for and to see whether you’re enjoying your life on the way to meeting your professional goals.

Don’t rush this step. What feelings come up? There may be happiness and feelings of achievement tinged with regret and disappointment. Stay in your feelings for a while and see what’s there. Doing this exercise will help put you in the right mindset as you begin to think about what you want going forward and whether or not your current role is the best place to get it.

Know what your values are

Your values are your north star. If you know what they are and you follow them, you will be acting in alignment with who you are at all times, which is another way of saying that you’ll always act in ways that are respectful of your own worth and dignity.

The word values is often used, but many people have not taken time to identify with precision what their values are. If you can’t name your top 2 values immediately, take some time to figure out what they are. There are a number of exercises you can do, such as selecting your values from a “values list” or thinking of people you admire most and digging into what qualities you see in them that you’d like to emulate.

A few things to keep in mind as you identify your values:

Don’t worry about appearing shallow

Things like vanity, money and success can all be valid values. You don’t have to share your values with anyone else, and there’s no one to impress—including yourself. If you’re not honest about what you care about, this process won’t work well. Dishonesty with ourselves leads us to live other peoples’ dreams

Limit your values

While you may have many values, select no more than your top three. Otherwise, it can prove difficult to use your values to make decisions.

Values need not be immutable

At different life stages and as we grow, what we value will most likely change. As such, you should revisit this exercise from time to time. I’d say at least yearly

Know your options

Before we get into what you should do, you need to know what you can do. You may have a general idea already or you may need some direction. Either way, ensure that you have spent enough time grasping all of the possibilities and writing them down so you can keep track of them. Spend some time suspending reality. If there were no restrictions on what you could do, what job would you take on? Many of us don’t make sufficient time to think about this. You can always rule things out later, but first, see what’s possible.

There are many ways to do this, but here are a few:

Researching

Use all of the tools around you, including the internet, periodicals, books and recruiters/job consultants so you have a good lay of the land as it stands today and you understand what the business landscape is likely to look like into the future. Your reading should include topics like business, economics and finance, but you should also follow trends in fields such as technology, science, art and sociology.

Talking to others

Find the people in your circle who are thinking about new ideas and who are well read. Have people who are from varying fields of knowledge in your regular social orbit. These people can help validate what you know and to show you what you don’t so you can better ensure that you’re covering all your bases. What you end up doing in the future may be something that’s not even a job today. Speaking with a diverse set of people can help you be more creative so you don’t just go for what’s already out there.

Getting inspired in nature or otherwise.

If meditation in its traditional form is your thing, do that. (And if you haven’t tried it, you should so you know if it works for you or not). If it’s not your thing, think about an activity you can do that helps you clear your mind and get into the present moment. For a lot of people, getting out into nature is a way. For others, it might be going to a concert hall or a museum or playing extreme sports or any other number of things. Doing the activity or activities that work best for you will help give your mind the space to come up with better ideas and reach better conclusions.

Getting extended rest and relaxation

Your body and mind need time to rest for them to perform at their best. To do this, find sustained time away from stressors. It’s likely that you’ll need more than a couple of days to get the most benefit from this exercise. If you can take a week or two—or longer, take it. If you can’t, perhaps you need to cancel plans for a long weekend and stay in and focus on yourself rather than doing chores and running errands. When you’re always in fight-or-flight mode, it’s hard to think about anything outside of the current situation. So free your mind of those troubles to get it focused on answering your career-related questions. I know this can be difficult to do, but make time for it. There’s no need to try to come up with answers during this time. You’re probably exhausted. Focus on resting.

Ideating

You’ve heard from others, done your own self-study and rested up. Now it’s time to put it all together. This will involve spending real time thinking about what you’re good at, what you can do with ease, what is valuable to you and what you either enjoy or are at least willing to bear. Synthesize all of the knowledge and inspiration you’ve gotten and filter it through your values and work objectives. This process is something that others can’t do for you, and that you won’t find on the internet (yet), so you have to spend the time on this yourself.

Speaking with a coach

Coaches are trained to help you clarify what you want and the underlying reasons why, so if you’re feeling stuck and don’t know what else to try, a coach can be a great resource. They can also help you accelerate getting to the answers you’re seeking, so if you’re in a hurry to figure things out, find a coach and work with them. It will cost, but if you work with the right person, you’ll get back far more than you invest.

Narrow things down

After exploring all that you could do, you need to decide what you’re going to focus on. Here’s a framework I’ve used when having to make tough career decisions. It grew out of something someone told me a long time ago about flipping a coin and then seeing how I felt about the outcome to make my decision. (You can learn more about that approach here.)

Make a list of all of the attributes that you care about with respect to your career. Here are a few examples, but you may have a completely different list with more or fewer items.

• Ability to move abroad
• Ability to move into different roles
• Balance
• Benefits package
• Familiarity with the role
• Freedom
• Institutional goodwill you’ve built up
• Money
• Networking opportunities
• Perceived Security
• Prestige
• Sense of purpose
• Skills attainment
• Working with smart people

Once you have your list, weight each attribute based on its importance to you now. Another way of stating that is to weight attributes that you think will help you to be in a place to achieve your medium- and long-term goals. In this way, your items linked to your long-term, visionary goals may actually be of less importance now than items linked to your short-term, tactical goals.

Here’s the process:

- list up every attribute about your life and career that is important to you given your values and short- medium- and long-term goals;
- weight those attributes based on importance;
- assign each potential opportunity (including your current job) a score from 1 to 10 based on how likely it is to satisfy each attribute you listed;
- multiply each score by the applicable attribute weighting; and
- add up the resulting scores for each potential opportunity

The highest scoring job should be the one you choose—with caveats described below.

Make a decision

Unless you have already done very thorough research, you may find that it’s hard for you to determine whether a new job opportunity will allow you to realize the objectives you have identified as important. The good thing is that instead of just having a list of possible jobs and wondering endlessly about which one to do, you know what gaps in your knowledge you need to fill. Not sure if you’ll be working with smart people at a company you’re interested in? Maybe that means finding out by asking people in your network and going to networking events that people from that company attend, among other things.

Sometimes, despite your best efforts, you won’t be able to answer all of your questions using the resources you have. The good news is that this gives you things to ask during the interview. Asking nuanced questions that you really want the answers to will show that you’ve actually looked into the company a bit on your own and thought about your situation and how working at the company will impact it. Depending on the nature of the question, you might wait until after you receive an offer, as opposed to asking it at the interview stage. But either way, make sure your most important questions are all answered before accepting an offer.

Now that you’ve got your answers, you can run the model and see how things shake out. Look at the results and see how you feel. Does the job choice the numbers are telling you to make feel good? If so, then it’s probably the right one.

If you don’t feel good about what the numbers say or there’s some resistance, ask yourself why. It could be because you’re struggling with making a choice between two things that you believe will give you the same amount of utility. It might be because leaving the comfort of what you know behind to do what you know you should do is hard. It could be because you haven’t included all of your most important attributes about your career in your model or that you haven’t weighted them properly. Being honest is key. Don’t change the weightings or the items just to keep yourself feeling comfortable. If you’re not clear on whether you’re changing your answers for the right reasons or the wrong ones, you could benefit from talking the results through with a neutral third party, such as a coach, who can help you think things through in a logical and objective manner.

Other things to consider

You’ve decided to stay in your current role or to leave. That’s just the beginning. Keep the following in mind is crucial to your success going forward.

If you decide to stay

Recommit yourself to your job and treat it like it’s a new gig (see “Joining a new company” below). Be grateful for the role and give it your all. See where you can improve and do so. If you need to strengthen your reputation or grow your reach in the organization, make a plan and execute it. Even if you’ve decided that you’ll do one last year before leaving, make it your best year ever.

If you decide to leave

Let’s say you’ve looked at the scores your model gives you and you’re feeling good about taking an offer elsewhere. In most situations, you’ll be best served if you leave well. You never know when people from the company you’re leaving will come back into your life (as a client, boss, reference, etc.), so it’s best to treat everyone with professionalism and respect at all times.

Leaving well doesn’t mean the same thing everywhere, so if you’re not aware, make sure you know what you’re contractually required to do and then what the norms are in your industry and your organization, which often exceed what’s technically required. You should also communicate with your future employer early so they know how much time you need before you start your new role.

The advice above assumes that your employer has treated you with professionalism and respect. If that’s not the case, the timing of your departure and how much you contribute after you’ve given notice may need to be adjusted. But even if you are leaving under less than cordial conditions, think about how you want to comport yourself given the circumstances, and potentially roleplay it out, so that you don’t react in a way that is disproportionate to the situation.

I won’t get into everything here now, but there are a host of other things to consider when leaving your company, such as when and how to tell them you’re leaving, how to deal with counteroffers if you receive one, handing over work and creating manuals, whether or not to work long hours after you’ve given notice, and the exit interview (if that’s still a thing at your company). Make sure to think all of these things through.

Joining a new company

Before you join a new company, remember that this is a chance to reset. Part of that is having a vision for yourself of what you want to achieve. Another part of it is to assess who you were at your old job and to decide what worked and what didn’t. What more do you want to achieve here that you didn’t in your former role? How can you grow into being that person? What do you need to stop doing? Do you even want to put in the effort required to reach your potential in that area? Be honest. There are multiple ways of being successful in a role. And maybe you’ll find that you need to redefine your role in order to make it work best for you and the company. You might have to bide your time for a little while before you realize what you want. It’s all a process.

In short, take the best of you to your new role, and leave any pain/trauma behind so you can give the new role your all.

Things to keep in mind regardless of where you work:

Ultimately, we’re responsible for our own success and happiness at work. No matter where you end up, make the most of it by doing these five things.

• Know what your company expects of you, and what you need to do to put yourself in the best possible position to beat those expectations
• Know all of the resources that your role provides you personally (discounts, chances to meet new people and to travel, etc.) and professionally (chances to upskill, chances to raise your profile, the reputation of a large, well-known company, access to industry knowledge/reports/databases, etc.)
• Effectively network in your department, company, industry and beyond, regardless of your role
• Know what role you want next, either inside of the company or outside, and what steps to take every day to move you toward it
• Make time for your mental and physical health so you can enjoy life but also come to your job turned on and ready to do it in a sustainable way

Constantly evaluate

The work of deciding whether to stay or go is never done. Stay in your current role for as long as it’s the best role for you and leave as soon as it’s not.

After making your decision to stay or go, regularly reassess your situation—preferably quarterly—to ensure alignment with career expectations and personal satisfaction. Avoid reactionary decisions based on transient negative experiences; instead strive for objective evaluations. So don’t decide when you’re angry or fed up with work. Likewise, though, don’t be lulled back into doing something you know isn’t right for you when work is slow or you’ve just had an amazing time away or your bonus has just hit. I’m not saying to ignore those things, but don’t give them more weight than they should have.

Return to your decision model and rerun the scores often. Be careful though: our values and needs may shift as we learn and evolve, and as personal and professional needs change. Update your model as you need to, which also means doing work on what’s important to you regularly, both personally and professionally.

Note that in every role there are expectations as to the minimum tenure of staff. Under normal conditions, I am not suggesting that you should leave prior to such time, as doing so may give the impression that you lack the requisite qualities and/or commitment to remain in a role, which could be seen negatively by employers and peers. The quarterly check-in is, in part, meant to help you reaffirm that you are in a role because you choose to be there, and should therefore make the absolute best of your current opportunity. Once you have exceeded the threshold tenure (or before if you have serious convictions for doing so), you should consider your options seriously if there are opportunities better suited to you elsewhere based on your model. Keep in mind that opportunities do not exist purely outside of your organization. You may find that you love your company but want to assume a new challenge in another department or geography. Internal moves generally require a shorter tenure, though you would still benefit from knowing how long of a tenure is expected prior to making an internal transfer.

As you decide whether to remain in your current role or seek a new one, the key is to engage in a periodic reflective and strategic process. The crux of making a consequential decision about your career lies not only in the evaluation of tangible benefits and the allure of new challenges but also in the resonance of these choices with your deeper sense of purpose. By identifying and staying true to your values, being open to new possibilities, and committing to personal and professional growth, you can navigate the complexities of career transitions with heightened confidence and clarity.