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Avivah Wittenberg-Cox FRSA looks at the crossroads we come to at various stages of our lives – and explores how we can make those transitions less daunting.

There is a small, disheveled baby robin making her very first steps in my garden today. She looks a bit dazed and exhausted, her lovely yellow down all awry. I know exactly what she feels like. She looks like a lot of people I know right now. At almost every age, everyone seems to be on the cusp of a similar transition: taking their first steps into an uncertain and illegible new world. Overhead, World War 2 planes are flying in formation to celebrate the British Queen’s official birthday. Like my own mother, who shares her birthday, she is turning 93. They are both remarkably well, and not finished with transitions.

At just shy of 57, I feel poised at late mid-life, equi-distant between these beings, the bird and the queen/ mother figures. From this Middle Kingdom, I can observe my entire family hanging, in a seemingly collective cliff ritual, on the edge of change. We are all transitioning – quasi simultaneously and quite unexpectedly – into our next chapters. My daughter is graduating college this summer. My son is starting his first company. My husband is recomposing into something he resists calling retirement. My mother has just been fitted with her first hearing aids and is suddenly complaining about the noise of the sirens in the city. Not to mention my trio of good friends, one who lost a job, one who moved countries and one who split from her partner.

Every one of this cross-generational crew is struggling to let go of what was (identity, community, colleagues, and competencies) to embrace what’s next (as yet unknown, undefined and ambiguous). There is a mixture of fear (who am I?) and excitement (I am SO ready for a change), confusion (what do I want?) and certainty (it’s time to move on).

Thanks to amazing increases in longevity and healthspans, I’m sitting in the garden, watching Robin Jr. test her fledgling wings, researching how to prepare for the several decades still ahead. The sixties and seventies are decades that used to be considered retirement age but are – slowly – being reclaimed as an entirely new, and potentially rich, phase of adult life. Not so much the ‘golden age’ at the end of the rainbow, filled with cruises and age-segregated communities, fashionable in the past few decades. But rather the revelation of the human within. A time of self-acceptance, engagement and, if you’re lucky, cross-generational generativity.

A variety of writers are struggling to name this new period, snuck in between empty nests and the delayed onset of ill-health, mental or physical. From Marc Freedman’s The Big Shift to Mary Catherine Bateson’s Composing a Further Life to William Bridges’ The Way of Transition, everyone is exploring how to gracefully move into what these writers are calling the Third Age, Portfolio Life, Adulthood 2, the Encore Years…

My favorite is Gloria Steinem’s coinage of the term Perennials. While it is a very different phase from that of the millennials now trying to enter the world of work, a lot of the emotions seem to rhyme. Turns out it is neither easy either to enter decades of working-striving-proving, nor leave them. The shift is an emotional process, usually involving four phases:

LEAVING

There comes a time in some jobs, life phases or relationships where you know an arc, or a story, has reached its end. There is nothing much left there for you. Colleagues may start noticing the passive-aggressive resentment that oozes from your continued presence in this space. This is the land of burn out and depression and exhaustion. It is also often an essential pre-requisite to re-creation. It is not an easy time – for anyone involved, at work or at home. We can spend quite a lot of it loitering unproductively, wondering whether we should stay or go. The fear of letting go of the known is a powerful brake to breaking free. Who will you be without this title, this salary or this position? You have to literally wean yourself off the branch you’ve been sitting on, sometimes for decades. Usually, in the end, the choice to leave becomes one of survival. In order to breathe, you need to move on. Grow, or go.

LOOKING

Looking is the exploration phase into the next country on your life map. Where will you travel to and with whom? Before you can begin to answer, especially in later life transitions, you first need to figure out two things: who you are now and what you want next. This is usually the hardest part, and impossible for millennials to do quite yet. What Michael Ury calls Getting to Yes With Yourself. Do you even have the faintest idea? A few questions to set you on your way include:

• What have you most enjoyed in your career to date? 
• what kind of people energise you?
• what kind of environments shut you down?
• Do you want to transfer skills or start from scratch and reinvent?
• Build on accomplishments or never hear of them again?
• Move from for-profit to for-purpose or the other way?
• Focus on one thing or cumulate a series of side-hustles?
• Anchor security or toss it to the winds?

In this phase, which can take several years, you’ll want to pack a comforting travel bag: an advisory board of trusted supporters, a realistic timeline, a financial plan and clearly negotiated support from your partner if you have one. Rome wasn’t built in a day, and preparing for the next third of your life requires more than updating your LinkedIn profile. Invest in this phase as you would in any 20-year project. Seriously.

LOVING

Happy later life transitionists often let their hearts lead. This can be hard for the disciplined, successful rationalists who have let reason rule the roost for decades. But this phase involves road testing things you love doing and care deeply about. The more you enter later life investing in people and issues that you care about (and not in those you don’t, or no longer do) the more it will re-invigorate you and carry you into your later years with purpose and passion. Both Harvard and Stanford have introduced programs aimed at successful Perennials interested in putting their talents to broader uses. This phase is often about moving from a focus on self, nuclear family, and career to giving back and broader impact. What have you always dreamed of doing? Envied others for doing successfully? Or fervently believe in? What passion, or hobby, or community have you connected with? What legacy would you like to leave? Or what long-ignored inner garden is yearning to blossom?

LEAPING

When you see people who have found their feet, and invested in something they truly care about, sometime for the first time in their lives, it is an inspiring sight. Like the book I wrote on Late Love, where people often found their soulmates in their latter decades, some people only really find, or allow themselves to find, their calling after they’ve fulfilled all their duties – to their own earlier expectations, to parents, to family. The freedom that comes from finally aligning with yourself is profound. Neither fame nor fortune can feed the unsatisfied soul, as recent tragic suicides remind us, but the meaningful work of a mature human can – and often does – feed the world.

As Erich Fromm wrote half a century ago, “The whole life of the individual is nothing but the process of giving birth to himself; indeed, we should be fully born when we die – although it is the tragic fate of most individuals to die before they are born.” 

Now that we have a few extra decades to grow wings that air lift our true selves into sight, we may see many millions of those tremulous, frumpy little birds take flight. We need them urgently.


 This is an introduction to my next book on Late Work: Finding Meaning in Maturity. I’m looking for RSA members to interview who made a significant career switch after the age of 50, and who discovered a whole new lease on life and purpose through the change. If you’d be interested in participating, thanks for sending me a short summary of your story (to avivah@20-first.com) and I’ll be in touch. Look forward to connecting!

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