Should You Look for a New Job?

Today, we're examining one of the most common yet consequential career dilemmas: should you look for a new job? Rather than making this decision based on emotion or a single frustrating day, these questions can help you gain clarity on next steps.

I often talk to people about the “push and/or pull” of career transitions. Are you being pushed from your current role for some reason(s) and/or pulled into another role? “Pushed” doesn’t necessarily mean that it’s involuntary and the company would like for you to leave, but rather it might not be a great fit for you anymore.

Either way, you have some questions to ask…

Great Questions

Here are five questions to help determine if you should look for a new job:

1. What are the top three most frustrating things about my current job?

   Your answer could be one of many things, but some common answers are: having to work with a particular person or two, a long commute, any commute, being underpaid, managing specific tasks, it feeling too transactional and not enough relationship building among colleagues, being too busy or not busy enough, etc. A common saying goes: “People don’t quit jobs—they quit bosses.”

2. What are the top three things I would miss most about my current job if I were to leave?

   Common answers are: people, mission, flexibility, stability, etc.

3. What are you optimizing for right now in your life?

   Get a great mattress and a great job, as you spend at least two-thirds of your life sleeping and working. A great job aligns with what you’re optimizing for in this current season. There are different seasons in life when it’s okay to lean in or out of work based on your priorities. Do you have elderly or sick parents? Young kids? Mounting debt? No debt? No spouse? A demanding spouse? Aligning your work commitments with overall goals is important in helping you achieve them.

4. What frustrations in question one above can be improved with hard conversations?

   The best company cultures are responsive to people when they are frustrated. It may be difficult to start and have the conversation, but ask yourself if some or many of your current frustrations could be solved by your team or manager. If so, the devil you know at your current job may be better than the devil you don’t know at the next one.

   Further, it’s worth thinking about your growth potential before you make a move. If you've learned everything you can in your current position and lack clear paths to new challenges, it may be time to look elsewhere. But if you're still developing valuable skills, consider whether a move within your organization might provide fresh challenges.

5. Using your response to question three as your guiding principle, evaluate how much weight to give the frustrations listed in question one and the positives in question two—should you find a new job?

   Often, your gut already knows when it's time; this process simply helps your head catch up and put words to the feeling.

Great Finds

I live in Boston and recently, during the 2025 Boston Marathon, Brazilian runner Pedro Arieta stopped just short of the finish line, sacrificing his pursuit of a personal record to help fellow runner Shawn Goodwin make it across the finish line.

Who can you help get to their finish line? Read more here.

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Onward!

Mike