The 5 Thinking Hats of Transitions: What they are, how to use them, and how they benefit any transition


I believe thinking is a skill and can be improved with the right help, frameworks, and methods to do so.  In a transition, according to author Nancy Schlossberg of Retire Smart, Retire Happy: Finding Your True Path in Life, there are five common ways people explore their retirement and the next stage of life in this important transition.  I'm taking this a step further and extending this idea into ALL Transitions as well as coupling it with some of famous creative thinking polymath Edward de Bono's thoughts (he's also a psychologist, philosopher, author, inventor, and consultant) from his book Six Thinking Hats.  The benefits of trying on each hat when thinking about, planning, or experiencing a transition may help to reframe, reorganize, or reinvigorate what the art of the possible is for you.  Ultimately, this will enrich your transition whether it's retirement, a career change, or even in an organizations transition in a larger sense.

The 5 Thinking Hats of Transitions

These 5 thinking hats are presented here in no particular order or importance.  Think of them as general ways people experience and explore a transition and that one does not necessarily experience one at a time.  More often then not, we traverse a mixture of these types at any given time or we "wear multiple hats" at the same time.  However, if you stop and think with a particular "hat" on and perhaps even pursue your transition fully embracing a particular "hat", you may find the experience more rewarding, enriching, simplified, and straightforward.  

  1. The Continuer
    1. This hat is simply an extension of your current identity or organizations identity.  It seeks to perpetuate the roles, relationships, routines, and assumptions that make up your work, home, or volunteer life and they remain central to who you are and what you find important.  This mindset can sometimes be more possible in one circumstance vs. another.  Perhaps you can move from a full time teacher to a retired teacher but a volunteer in the same school or school district, thus maintaining almost similar structure to your life. 
    2. Questions to explore:
      1. Can you continue your current identity and life structure but packaged in a different way or ways?
      2. Are there opportunities to maintain same or similar roles, routines, relationships, and assumptions post-transition?
      3. What are the pros/cons with this frame of mind and pursuit in your transition or your organizations transition?
  2. The Searcher
    1. With this hat on, you understand and act with the knowledge that you need to move on and transition to something new but you're unclear about the exact place you're seeking or going to end up.  There is space with this mindset for trial and error to gravitate to what fits best.  The key with this hat is to focus on perseverance to move through the transition and end up where desired.
    2. Questions:
      1. What are a few steps you can take to seek out new roles, relationships, routines, and assumptions for your next stage after you transition?
      2. Are you comfortable trying something new and dropping it if it doesn't suit you?
      3. What kinds of activities and resources might be required by you or your organization and spend some time exploring, searching, and experimenting?
  3. The Retreater
    1. This mindset happens to many of us at some point in our life, in some kinds of transitions.  Basically, its like giving up, and succumbing to the minimum level of roles, relationships, and routines in life.  Boredom or in some cases, depression, characterize this hat.  I believe this can be an important stage of transition as well as thinking about an upcoming one because it can be thought of as stripping away all distractions, complexities, and unnecessary aspects of your life or organization.  The adage "no where to go but up" exemplifies the realization of this perspective.
    2. Questions:
      1. What might happen if you "gave up" and stopped being deliberate, planning, and pursuing something new and different for your transition?
      2. What kinds of disabilities, ailments, or challenges might occur for you to become a true Retreater in your next transition?  How could you reframe these circumstances to step out and away from a Retreater mindset?
      3. What would it look like for your organization to put a stop to it's current initiatives and pursuits of growth (but still serve your customers well) and instead allow space to settle back and simplify for some amount of time?
        1. How would this benefit your organization? Harm your organization?
  4. The Adventurer
    1. This is a mindset of full of positive and new "what if's?" What if you stepped out of your comfort zone and learned a new athletic skill? Art skill? What about a whole new capability set for your organization like in-depth sales and customer service training for your whole organization? This is the "go big or go home" mindset.  I look at these transitions as taking a "big jump" away from your current roles, routines, relationships, and assumptions and exploring new horizons.  This can also be thought of as "stressing the system" in your life or organization.  Most biological systems thrive when stressed periodically, so they adapt, improve, and shed unnecessary and inefficient uses of resources and energy. This can also be true for your personal life or organization.
    2. Questions:
      1. What are 3 new, exciting, and uncomfortable skills you can pursue learning in-depth and practicing?  Perhaps even a whole new role for your paid work or volunteering work.
      2. What are some best case/worst case scenarios you can explore when thinking about 1 big adventure to take on (you'll have to define that too!)?  You may find the worst case scenarios, when written down and realistically examined, really aren't as bad as once thought.
      3. What kinds of circumstances would have to take affect in your organization or life to feel a sense of urgency, importance, and energy to transition and improve?
  5. The Easy Glider
    1. This is the "go where the wind takes you" mindset and is somewhat of a conglomeration of the rest of the hats of a transition.  More characteristically, it embraces each day and moment as full of possibility and allows it to unfold a bit more organically than the others.  However, there is some flavor of doing the activities you enjoy, engaging in stimulating relationships, etc. vs. pure trial and error (Searcher) or seeking dramatically new experiences (Adventurer).  They are often open to anything but are deliberate and in control.
    2. Questions:
      1. What's going on in your life or organization that you enjoy about it?  Take notice and pursue new versions of these activities and roles as they come.
      2. How has this hat shown up in your life or organization and what are some ways you see it happening in the future?
      3. What are some ways you can embrace and celebrate right where you are in life or in your organization?

These 5 Thinking Hats are useful tools for your personal life, career, or organizational transitions.  I think many of us can identify with one or all of them, in our individual lives or perhaps as persona's of our organizations as well.  No mindset is necessarily better than the others and I believe they all have a useful perspective to at least explore in a thinking exercise.  I am certain deliberately stepping into a different mindset or "hat" in this case is a valuable way to explore an upcoming or existing transition, in our lives or businesses.