Lisa Kavanaugh breaks down The Crossroads of Should and Must, inviting us to get clear on our intention for our time and our life.

I was attending the Modern Elder Academy in Baja last April with Barbara, when The Crossroads of Should and Must called to me from the bookshelf. It’s the kind of book I wish I’d written, light and easily read in a day, with the depth and wisdom to last a lifetime.

Being a coach I can’t escape the topics of life, purpose, and passion. Yet, I’ve always struggled with the heaviness of those words and the paralysis that can come from feeling clueless to your life passion and purpose. The author approaches this inquiry in a way that is approachable and inviting and leaves the reader excited to start exploring and playing their way forward as they examine who they really are and what they really want.

The concepts are simple. Should and Must. Shoulds are how other people want to live. In choosing a should-led life, we are choosing to live as, or for, someone else. Sit with that for a minute. How often do we refer to what we Should be doing with loaded judgment?

How often do we refer to what we Should be doing with loaded judgment?

She goes on to explain that living a life satisfying “the shoulds” leads to what she calls “the pain,” which cuts across gender, location, and age without discrimination, leaving those affected by it feeling dissatisfied. Her belief is this: you are not living the fullness of your life because you are not expressing the fullness of your gifts.

This is where Must comes in. Must is who we are, what we believe, and what we do when alone with our truest, most authentic self. Must isn’t something we need to go looking for or figure out, it’s who we already are. Yet we often forget, having contorted ourselves into another shape to satisfy all “the shoulds” we’ve been taught to conform to since the moment we got here.

Where are you letting The Shoulds lead your life?

So if Must is the Nirvana, why aren’t we all living there already? Because most of us don’t even realize we are living within the constraints of our should-based belief system. The first step, is awareness (isn’t it always?) As many of my favorite books do, this book offers powerful journaling exercises to get to know your Shoulds because it turns out in order to learn what you Must do, you first need to unlearn what you Should do.

On the journey to the land of Must, you will encounter many stumbling blocks: money, space, time and the dreaded sea of vulnerability. The Crossroads of Should and Must offers practical tools for overcoming each to create the space and freedom for your innermost desires to bloom and for your dreams to become reality.

“Don’t ask what the world needs. Ask what makes you come alive and go do it. Because the world needs are people who come alive.” – Howard Thurman, philosopher

In 2013, I quit my fast-paced CTO job to take a year off and backpack around the world with my husband. I knew deep down that I must travel, and read, and swim in the ocean, meet new people, and have foreign experiences in far-away lands without having any idea where it would take me. That pathlessness allowed me the space to connect with a deeper curiosity around personal development, transition, freedom and how I might be in service of other’s wanting to make their version of the heart-led leap.

This book is for anyone who feels that pull to break free but isn’t sure where to start. Find a sunbeam, curl up with this nugget of actionable wisdom and be open to what emerges!

What makes you come alive? How might you invite more of that into your life?


Lisa Kavanaugh combines over a decade of experience leading large software teams with her talent for “situation redesign” to partner in the creation of more meaningful impact in her client’s personal and professional lives. She brings a wealth of experience in the positive transformation of individuals, teams, organizations & culture. 

A Look at a Book is a series I’m hosting to help keep you informed about the latest books having to do with adult development and middlescence. A Look at a Book is an efficient, enjoyable way to stay informed. 

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