Is it Time to Move on?

Fall always feels bittersweet to me.   

I love the stillness of the air, the waning warmth of the sun and the vividness of the trees just before they shed their leaves for the season.  

I also feel a slight sadness.  Without being fully conscious of it, I notice that this time of year makes me want to shed a few things of my own.  Some of what I’m letting go of is small and insignificant.  It’s the equivalent of cleaning out my closet.   

But other things are more daunting to release - work that had once made me happy but no longer does; relationships that haven’t worked for a long time; and dreams that I have outgrown.   

Here’s the thing though, endings are hard. They are full of ‘what-ifs’, ambiguity and sadness.  Letting go also takes time.  We can’t expect ourselves to have an intellectual knowing and then move straight into action.   


A client recently told me that he knows it’s time to move on from his organization.  He has been there for 15 years and hasn’t been happy for a long time.  He chastised himself for not taking action sooner, using that as evidence of his procrastination.   

I don’t see it that way.  I see a 15-year relationship that was once fulfilling and meaningful that no longer is.  I see someone who is coming to an intellectual understanding that hasn’t yet made its way into his heart.*  I see a person who is deeply intentional rather than reacting impulsively.   

So, as you pull out your sweaters, dive into your favorite pumpkin flavored deliciousness, and snuggle up to your pet, your partner or your body pillow, here are 5 reflection questions to help you release what is no longer working and make room for what is next: 

  1. What do you suspect is coming to an end? 

  1. What are you putting energy into that is not coming back? 

  1. What relationships have you outgrown? 

  1. What no longer brings you joy? 

  1. What do you yearn for and how can you make space for it? 

I struggle with endings. They feel like a ‘no’ or a rejection of something or someone. Instead, I am working on being grateful for what I am releasing – reflecting on how it has contributed to where I am now and, at the same time, seeing that it is no longer generative. 

Here’s to making room for what wants to emerge.

*If you would like to understand how we come to make changes in our lives, you can learn about Prochaska’s stages of change here


Starla Sireno is an NYC-based Executive Leadership Coach. She has helped develop leaders in some of the most recognized organizations ranging from Fortune 500 to fast-growth technology companies. Starla has partnered with more than 500 leaders in over 60 organizations around the world. Inquire how you can work with Starla or her team.