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Should I Stay or Should I Go? Questions to Ask When You're at a Remote Career Crossroads

At some point in our careers, we have all had those moments we can call crossroads, where we need to make a decision about whether to stay in a job or take other opportunities.

This moment could be the result of a job offer, a burning desire to strike off on your own, or it could be the result of your current position not being the best place for you at this moment in your career.

The Remote Career Crossroads

"Should I stay or should I go?"

Before you can answer this BIG question, ask yourself the following series of smaller questions.

What does your ideal job look like?

Describe what you really want to be doing on a daily, monthly, and yearly basis. What kind of projects are you working on? What are you learning? What do you want to accomplish? And finally, how do these responses differ from what you experience in your current position?

Is your ideal job possible in your current organization?

If you can see real examples of people moving up in the way that you would like to advance, then there's a fairly good chance you can make that upward movement happen for you. If this is your situation, then outline some concrete goals for yourself to make this happen, like scheduling a conversation with your boss to discuss your future at the company.

Conversely, if there are no or few examples of people moving up, or the position you want just doesn't exist in your organization, that's a sign that your company might not be the best place for you to continue your remote career.

What do you like about your job?

Take some time to focus on the positive aspects of your job. What do you love about your work? How essential is it that you keep those aspects in your professional life? Then, ask yourself if you would be able to find or replicate these conditions in another environment. What would that take?

Is money the only thing keeping you at your current job?

For most of us, we work not only because we like what we do, but also because we have to put food on the table, save for retirement, and do all the other things in between that require money. If money is the only thing keeping you at your current job, that's a pretty good indicator that it's not necessarily the best place for you. If that's the case, think about how you can make some changes so that you do not have to make this decision based on money. Do you have an emergency fund? How long will it last you and your family? What can you do to contribute more to this fund? What can you do to have another position lined up that will pay your desired salary?

If you could change all the things you disliked about your job, would you still want to stay?

This question gets to the heart of what will make you happy—it will tell you whether the crossroads is about something missing in the organization or about something that is missing for you. 

If you could change everything about your current position—the salary, the responsibilities, the career path—would you still want to stay in that organization? If the answer is no, that means that there is something bigger that is bringing you to this crossroads. It could be that the organization is just not a good cultural fit for you, or you want to go out and start your own company. Or it could simply be that the time has come for you to move on to another stage in your remote career.


These questions have helped me make some big remote career decisions in the past, and I hope they help you, too. What other questions have you asked yourself (or others!) that have helped you make big career decisions?

Here are more career tips to help you advance your remote career:

Our Growplaceless - Remote Career Development Course is designed as a guided approach to help you create a personalized development plan, and to be combined across teams for career pathing.


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