Designing Your Life: 3 Books to Help You Decide Your Second Act - Prime Women

Designing Your Life: 3 Books to Help You Decide Your Second Act

Designing your life means figuring out what you want.

The Top 3 Books for identifying and stepping into your Second Act

Through my work as an Executive Coach I have collected resources that I consider ‘crown jewels’  for designing your life — helping clients identify and step into growth goals that bring them more satisfaction, vitality, success and joy.  I’m sharing with you books that have helped my clients get unstuck, identify where they want to go (professionally, spiritually, attitudinally), and how to get going!

1. Finding meaning in the 2nd half of life: How to Finally, Really Grow Up by James Hollis, Ph.D.

This is one of several books helpful to designing your life.


Dr. Hollis is a renown author, Jungian psychoanalyst and former academic with a background in Humanities. He uses his research, teaching and clinical background to successfully translate Jungian analysis into language that is understandable. (With a little work on the reader’s part!)  To what end?  To help us recognize that we need to make our own meaning in each phase of life.  To understand that the things that gave us purpose and meaning in the 1st half of our lives will fall short sustaining us in the 2nd half of our lives. To grow you need to acknowledge, trust and value your inner compass.

What will you get out of this book?

  • Knowledge about personality development
  • Encouragement to bravely enter into soul searching
  • How to live a larger life grounded in integrity and authenticity
  • Affirmation that life is more about meaning and less about pleasure
  • Means to identify and challenge your belief system so you can choose a healthier one going forward
  • A way to reframe mid-life from crisis to transformation
  • The space and grace to address the question, “Who am I now?”

This book gave me a new filter for understanding maturity. Maturity is not static but in fact is a launching pad for new ways to look at, understand and react to the world with heart and eyes wide open.

Hints for getting the most out of this amazing book:

  1. Plan on reading and rereading (over the years)
  2. Read it bits at a time and allow yourself the space to ponder
  3. Keep a journal for reflection within arms reach
  4. Have access to a dictionary. It’s worth the challenge!


Designing your life: How to Build a Well-Lived, Joyful Life by Bill Burnett and Dave Evans


Leave it to the folks at Stanford to help us apply “Industrial Design thinking” to an approach of building our future life in a way that is creative, effective and FUN! A key premise of the book is that “Designers don’t think their way forward. Designers build their way forward.” Curiosity is key to “help you ‘get good at being lucky.'”

Building a joyful life can be done by design

What will you get out of this book?

  • How to use your curiosity and creativity to build a ‘what’s next for me?’ set of visions
  • Implementing the notion of prototyping these visions, testing them out, adjusting and iterating until you get to something you REALLY like
  • Identifying dysfunctional beliefs and then re-framing them. 


Jill’s dysfunctional belief — “I have an MBA and a Degree in economics — training not geared towards writing magazine articles!”

Jill’s reframing — “People are lifelong learners and welcome being exposed to the thoughts and styles of others on topics that are interesting to them.”

You’ll start with a way of taking stock of your current situation using a tool of the Health/Work/Play/Love dashboard. The writers offer several reflection prompts that relate to this dashboard. Then you are off to the design races!

Hints for getting the most out of this amazing book:

  1. Imagine yourself when you were a kid finger painting – fingers and colors flying all over the page – designs being erased or improved in real-time – new designs emerging fast – an experience that is both messy and liberating (a metaphor for the design experience)
  2. Buy a fresh journal to be used for the “Good Time Journal”


Ask Outrageously!: The Secret to Getting What You Really Want by Linda Swindling

Confidence plays a key role in designing your life


Linda Swindling has written what could be considered a field guide to overcoming the fear of asking for what it is you want and then going after it.  Her quick-read book offers cogent examples of the language to use and highlights great case studies, including her own failures and successes around asking.

She sets the stage by making you realize how much you have already sacrificed by not asking outrageous questions! She makes a strong case for venturing forward and asking for what you want and need. Success means getting outside of your comfort zone. 

What will you get out of this book?

  • Determine how to take calculated risks
  • Develop the skills to ‘ask’ in a way that respects the other person
  • Be clear and specific about what you’re asking for and then make it easy for them to say yes, and simple for them to follow through

Hints for getting the most out of this amazing book:

  1. Take the online assessment.
  2. Download the “Rules of Engagement” PDF.


I have a full library I want to share! Stay tuned for future articles!



Did you like this article? Sign up (it's free!) and we'll send you great articles like this every week. Subscribe for free here.

Related Posts

Second Acts Tina Frey
Reasons to Adopt a Cat after Retirement
Retiring on the West Coast
time to move on to your second act
Best places to retire in Arizona arrow sign
Tennessee Retirement feature
Reasons to love an empty nest feature
Retire in florida feature
Staying relevant after retirement
Retirement home vs nursing home
Changing paths at almost 50
PrimeWomen Award