CIO Leadership

When To Leave, When To Stay

I have stayed and left to my regret; I have stayed and left to my reward. I’ve become a bit wiser in knowing which is called for.

Joe Woodruff


November 23, 2022

I have left too soon.

I have stayed too long.

What should have been a send-off ended in a break-up. 

We stay too long because what we thought was comfort and a guarantee proved to be conformity and a graveyard for our soul. 

We leave too soon because we jump at an opportunity for a fresh start when what we need is to forge our own maturity.

After a while, you come to recognize that there is a rhythm to coming and going, to beginning and ending. It’s not a matter of right and wrong or best and worst. 

There is a then. There is a now. What is helps until it doesn’t. What frees is great until it binds.

The past has provided for you systems in which you grew. And then you outgrow them. Something happens in you that no previous form can contain.

Something must change.

When Not To Leave

  • You don’t quit in the middle.
  • You don’t leave because times are tough.
  • You don’t give up because of relational conflict.
  • You don’t end things for more money elsewhere.
  • You don’t escape problems. They will find you.

When To Leave

Great leaders know the right time to leave and how to do so with excellence, honor and celebration. 

You leave for three good reasons - on behalf of your identity, your capacity, and your purpose.


Your identity is an expression of your personality, talents and values. In a certain sense, it is fixed; it is who you are before anyone else in life tries to raise you, mold you and develop you.

On the other hand, your identity matures. Things that once defined you no longer do. It’s why we say, “You do you.” You break out, break free, break up and give yourself a break - all to be more true to who you sense you really are.

You leave when your values are no longer congruent or consistent in what you do.

When you find yourself doing what you don’t want to do, or not doing what you want to do, you are living incongruent with your values. If you can not easily adjust and realign to your values, you are in a place where you must leave.

Values are the non-negotiable behaviors by which you function best in life and work. They are not beliefs; they are how you must do what you do. You know it is a value if you want to put time, energy, ability and money towards it. You can audit your values based on those four attributes.

Sometimes you stay too long because you cling to an identity that is no longer true of who you are. If you cannot craft your identity, bringing it to full expression, it is time to leave.


You have talents, gifts, and aptitudes that cry out for growth, development, and expression. Your capacity will either expand or contract.

If you are not expanding your capacity, you are in a place where you must leave. You must do the same thing differently or a different thing the same way. You change your environment (such as a new company) and/or change your role (such as a new position). 

When I started CIO Mastermind, I decided to do the same thing a different way. I remain a technology leader (same thing). But I advocate for other technology leaders by providing value for their own growth and development.

Four questions to know if your capacity is tapped out in your current place and/or position:

  • Am I growing at a personal level to be a better professional? This is about mental, physical and emotional health.
  • Am I growing at a relational level to be a better leader? This is about advocating, leading and course correcting.
  • Am I growing at a positional level to be a better executive? This is about strategy, political savvy and stakeholder influence.
  • Am I growing at an industry level to be a better expert? This is about your brand, influence and legacy?


It’s time to leave when your purpose is losing depth. It’s one thing to have a mission, it’s another when you multiply it through developing leaders to do the same. 

It’s one thing to accomplish a great thing, but it’s another when you build a network of accomplishments.

It’s one thing to revolutionize within a company, it’s another thing when you birth a movement in your industry.

The moment you feel that your purpose has settled, that investing in it feels drab rather than deep, it’s time to move on.

Endings are necessary. Leaving is life. So is staying. 

I have stayed and left to my regret; I have stayed and left to my reward. I’ve become a bit wiser in knowing which is called for.

I trust that I have helped you to do the same. 

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