The Portfolio Life Transformation… Five Words to Guide You

Take a close look at the graphic above. Do these words appeal to you? Is this five part description an attractive alternative to what you have seen, heard and read about retirement? If so, let me add five words that will help guide your portfolio life transformation: patience, trust, experiment, curiosity and generosity.

In my thirty year career transition practice, I have mostly served high achieving clients in their fifties and sixties. Many decided they were not going to return to the all consuming demands of an executive level job. If some version of retirement was a viable option, a portfolio life has been a common goal for them.

I pride myself on staying in touch with my former clients, many of whom are now in the retirement stage of their life. As I think about my most successful and happy former clients, their stories and reflections are framed by the words patience, trust, experiment, curiosity and generosity. This blog is about how these words can help you find a path to your portfolio life.


It can take one to three years to settle into a portfolio life. I rarely get pushback on this suggested time frame when asking former clients about their experience. Think about the typical forty plus year professional career. How can a person let go of a powerful working identity and embrace a transformative new identity without the benefit of patience and pacing themselves over an extended period of time?

It is natural to want to move quickly from an ending to a new beginning, but this rarely happens. In fact, there are missed opportunities and many other risks when one tries to move too rapidly from one life stage to another.

I used to run a career transition workshop that included taking class time to ask all participants to read a one page document and comment on what they learned. The most common response to reading that document was, “This should be required reading for everyone going through a career transition. After reading these words, I now feel that what I have been going though psychologically and emotionally is normal, and I am going to be more kind to myself in the future, be more patient and less hurried.”

Here is the link to that one page document. Read it, and you will understand how normal and necessary it is to be patient and self-forgiving as you experience the stages of a major work/life transformation.


Often the best advice, and the best opportunities, will come with an element of surprise. Trust that if you are open to new opportunities, and actively pursue them, answers will gradually come your way. Stanford psychologist, John Krumbholz, coined the term “planned happenstance.” Krumbholz has said, “A satisfying career, and a satisfying life, is found through actively creating your own luck and making the most of new and unforeseen experiences.”

The first word in the Krumbholz term is “planned.” The last blog I wrote was about the planning process associated with creating a portfolio life. Read Creating Your Future, Guided By Your Past, to learn how to do your self-assessment and exploration. Remember that happenstance can be both good and bad, and that your planning process will help you vet opportunities in each of the five portfolio life elements.

For many, trust includes the belief that a higher power is helping guide your life. If this is true for you, this will provide comfort and peace during your journey. For those who don’t hold this same belief, trust will more likely be found in the lessons of life’s experiences and the generous people who will help you along the way. Either way, trust will help you remain optimistic that a portfolio life will one day come together for you.

Experiment & Curiosity

I am a big fan of author and Harvard educator Herminia Ibarra. I have recommended her book Working Identity countless times, and consistently receive favorable reviews. Ibarra’s recommendation for big changes, like creating a portfolio life, is to not risk getting stuck in “analysis paralysis,” but rather to craft experiments and shift connections in order to reality test and learn from others about future possibilities.

Be adventurous by crafting experiments

In her book, Ibarra explains crafting experiments this way, “Try out new activities and roles on a small scale before making a major commitment to a different path. We don’t, as a rule, leap into the unknown. Instead, most of us build a new identity by developing the girders and spans as “side projects.”

Ibarra also offers a cautionary note in her book, “By far the biggest mistake people make when trying to change is to delay taking the first step until they have settled on a destination. This error is so undermining because we learn about ourselves by doing, by testing concrete possibilities.” Don’t just keep thinking about or planning to run experiments in the future. Do them now, or do them soon.

Satisfy your curiosity by shifting connections

Here again are Ibarra’s words of advice, “Shifting connections refers to the practice of finding people who can help us see and grow into our new selves, people we admire, would like to emulate, and with whom we want to spend time. All reinventions require social support. New or distant acquaintances — people and groups on the periphery of our existing networks — help us push off in new directions while providing the secure base in which change can take hold.

We cannot regenerate ourselves in isolation. We develop in and through our relationships with others — the master teaches the apprentice a new craft; the mentor guides a protege through the passage to an inner circle. Yet, when it comes to reinventing ourselves, the people who know us best are also the ones most likely to hinder rather than help. They may wish to be supportive but they tend to reinforce — or even desperately try to preserve — the old identity we are seeking to shed.”


Follow a path with a heart

Read this passage from The Teachings of Don Juan, by Carlos Castaneda.
It will help keep you on a path of generosity. I have framed a copy of this passage, and read it often. It keeps me grounded and reminds me that I both need the gifts from the world, and the world needs my gifts. My goal is to follow a path with a heart all the way to its end. Is this your path as well?

Lead with generosity, but take good care of yourself at the same time. A few months ago I wrote a blog entitled, Balance… What Have You Done For Yourself Lately? In this blog I reference the book Give and Take by Adam Grant. The book compares givers, takers and matchers.

The moral of Grant’s story is that both the most successful and least successful people are the givers. The least successful are the “martyr” givers. They give too much, then burn out and can no longer give abundantly if at all. The most successful givers are what Grant calls the “otherish” givers. They focus first on the needs of others, but have a healthy selfishness and self-protection that prevents them from burnout or becoming a martyred, failed giver.


Patience, trust, experiment, curiosity, generosity… these five words will help guide you towards a portfolio life that has sustainability, satisfaction and purpose. Keep these five words top of mind, and in your daily practices. They will help lay the foundation, and a path, to your portfolio life transformation.