How do you know it's time?

Over the summer, we took a wonderful road trip in our campervan (Lolly) covering four countries and a few miles across Southern Europe with many memorable experiences. On our travels, taking a break from the digital, always on world, I had time to reflect and regroup after a particularly busy period this spring and early summer launching our book as well as taking on my first advisory board chair role (as well as the day to day of running several businesses).

Launching the book has been fascinating, challenging, inspiring – and so many other things. One of the activities I have really enjoyed as part of the process is talking to a variety of groups about it! At one of these sessions, I was asked an insightful question which has stayed with me, and I’ve spent time noodling over during my travels.

For those who may not be familiar with the focus of the book – it’s about inspiring experienced professionals through storytelling and practical advice on how to transition out of longstanding organisational careers into what Mike Mister, my co-author, and I refer to as fulfilling encores.

Back to the insightful question, we were asked: “How do you know it’s time?” On the face of it such a simple question, but when you really start to hone in, the answer is not straight forward. So many of us experienced professionals have huge amounts tied up in our professional identities, our routines well established with our work colleagues often forming our core friendship group (read family) – to change this can be both daunting even if offers excitement for some.

We have found through our book research as well as our own professional experience that many experienced professionals struggle to face and acknowledge this transition even if they are excited! Universally, we observe that the majority fail to dedicate sufficient time to reflect and plan adequately. As with many major life transitions (and arguably this is one of the biggest as it often coincides with other major life transitions like empty nesting, ageing parents, increasing health concerns etc), it takes courage to acknowledge that the time is approaching.

But the question after all that we were asked is HOW do you know it’s time? The answer I’ve concluded is complex and different for each individual. However, there are some consistent elements across the board:

  • it starts with an awareness of self and your relationship to your work and professional identity,
  • a willingness and commitment to explore an identity and a purpose beyond your current ones and openness to excitement about the art of the possible (even if fear is the dominant emotion),
  • an understanding of transitions (here we often reference William Bridges’ work on transitions) and how to manage these,
  • crucially, flexibility – as often happens – the time may be sooner than you anticipate or hope for.

It looks so straightforward when presented in black and white, however, it requires courage to be open with oneself and others, to embrace ones agency and to identify and recognise when the time is right to take the bold step of talking to ones organisation to make and act on a plan!

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