Dear Coach: How Do I Figure Out My Next—and Probably Last—Move?

September 14, 2023   |   Julie Diamond

What’s the Problem?

Dear Coach, 

I am a 53-year-old woman—a senior VP—and I feel like I have one more big push left for my career, but I don’t see an obvious path forward at my current company. I feel loyalty to this place that has given me so many opportunities; on the other hand, I’m getting calls from recruiters, and one company in particular has expressed very serious interest. I know that if I want to max out my potential, I likely need to leave. 

I’m torn! 

I’ve had a fabulous career, I’ve made it really far and have done a lot of great work., We’re basically set financially for me to call it quits. That said, I still have a ton of energy and drive and am not sure I’m ready to be done for good.

So, my question is, should I pursue a new role at a new company? Should I go to my current company and have a hard conversation about what’s next? Or should I just retire and finally spend more time with my family and do some traveling

How do I figure out my next—and probably last—move? 


Stuck at a Crossroads


What Do We Think?

Dear Stuck at a Crossroads,

Congratulations on a long and fruitful career! This is an exciting time in your journey, so let’s unpack your situation.

First, your question tells us that:

  • You’re not sure what the central motivating factor is for you. 
  • Therefore, you can’t decide what to do because you are missing the “what” and the “how” to thoroughly evaluate. 

So, exactly how is your problem a power problem? We think:

  • When you don’t know what motivates you, you’re in a powerless state. You’re swimming in possibilities because everything is equal, and you’re likely to change your mind with each passing breeze.

What’s the Solution?

To be able to move forward, you’ll need to consider what you know is true. 

Here are some thought starters for you; look at this list and ask yourself, “What do I know for certain?” 

  • “There are no roles in my company that I am truly interested in.”
  • “An outside promotion would stimulate my growth and learning.”
  • “I have the family/outer support to take on a huge new role.” 
  • “I’m a primary breadwinner, and I feel confident negotiating for a higher salary in a new role/company.”
  • “I have the energy to push hard/ learn something/ be at the bottom of a steep learning curve for the next couple of years.”
  • “I just need to just get off the treadmill.”

Choose 1-2 from this list that speak to you (or add your own). Then, write about it, talk about it with a friend or coach, and get clarity about what is motivating to you. Use that knowledge as a measuring stick to weigh your options.

It can feel overwhelming when you’re stuck at a crossroads—especially with the added pressure of thinking it needs to be perfect since it could be your last career move. But if you feel strong in your foundation of what matters most to you now, you will feel stronger in making a decision and sticking with it. 

We can’t wait to see which path you take!


Each month, we answer questions we often get from the leaders we work with and unpack how, at the end of the day, every problem is a power problem. If you have an issue you just can’t solve, get in touch! We’d love to answer your questions in an upcoming Dear Coach post. Find us at [email protected], or on LinkedInFacebook, or Twitter.