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Are you there yet?

How do you prepare for a life without a job title, agenda or executive assistant, Wendy Kay asks.

So, you’re a CEO, a company director or small business owner, and you’re about to retire.

Maybe you want to, maybe you don’t. Maybe you’re ready, maybe you’re not. Maybe you’re thrilled, maybe you want to throw up.

Whatever the sentiment, strap yourself in and buckle up because the next 30 years can either be the ride of your life, or a long, slow, road tarred with bitterness and regret.

The outcome depends entirely on how you reinvent yourself in a new world where often what you’ve achieved and who you were means diddly squat.

Leaders left without time to pursue anything else but their careers can be thrown into limbo when left with all the time in the world. They are confronted twofold when forced to let go of their incumbency, particularly those with The Commander or ENTJ (extraversion, intuition, thinking, judgement) personality type according to the Myers–Briggs Type Indicator.

Assuming the finances are sorted, the first few months of retirement can be a bit of novel fun. There’s that holiday you always meant to take, the home office to sort and the ongoing farewell lunches to enjoy. They fill the days, until the invitations dry up, the office is looking more bare than sorted and holidays just aren’t as exciting when able to be taken at whim.

There is no public exposure or contact; no influence or power; nothing to reflect what a legend you are or, more accurately, you were. Without proper preparation for this emotional backlash, retirement can be devastating.

The first most simple and obvious hurdle to overcome is the absence of a team to lead. With no-one in the morning to salute you, bar maybe a partner or a dog (although the latter might be more enthusiastic), the day looms empty of agenda. No meetings, no collaboration, no-one to fetch your coffee, or interrupt your thoughts. It’s a day in fact of nothingness.

The second whammy, less obvious but perhaps more profound, is the loss of title – the title that for years you relied upon to generate your self-worth and define your identity.

Former CEO, former Commanding Officer, former president, principal, or even former celebrity, will only cut for so long before you’re on your own. Then it’s up to you to remodel yourself and discover exactly who you are without the ‘former’ moniker to explain.

Letting go of power and responsibility can expose vulnerabilities never experienced before. Meeting others who have no clue as to who you are, nor care, can be confronting for those used to being in control, revered or even feared. Making small talk can be difficult when accustomed to strategising or troubleshooting; the art of waffling about nothing in particular was probably bypassed in all the busyness.

In the absence of a 24/7 Executive Assistant, discovering your spouse doesn’t want to cater to your every need can also be alarming. And don’t rely on the kids to fill in the gaps, they probably learned early on to live without your undivided attention.

The secret to getting on top of this brave new empty world is to start preparing for it in advance. Before you retire, spend time researching activities you can throw yourself into and discover clubs where you can meet with other like-minded people. Find an interest, you’ll probably be surprised to discover that your ENTJ mind can apply itself just as enthusiastically to a hobby as it did to business. Most importantly, try things outside your comfort zone. This will continue to push your buttons and apply the pressure needed to get the adrenalin flowing.

It has been said that people don’t grow old by living, they grow old by losing interest in living. Thirty years is a long time to be interested only in what you used to be. Embrace, instead, what you can become. Even without the title.

The dog won’t care. The cat never did.

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