‘The ultimate coaching question’

Many years back, I was over-stressed and unhappy, unsure what to do with my life, when a friend asked me ‘the ultimate coaching question’. Looking back, that’s pretty hard to believe: the conversation we were having took place on sun loungers in Indonesia during a long weekend break from our well-paid jobs in Singapore. I know, I know – just call me madam. Yet far from being incredulous, my Australian friend (so imagine the accent) simply asked me this: ‘What would you do if you won the Lotto?’ 


At first this was an easy question to answer; the usual suspects involving luxury travel and lavish living. ‘But when you’ve done all that, then what?’ These answers needed a bit more thought, but they were enlightening and very valuable, as they led to the realisation that there were ways I could start living like a winner – right away. So thanks, Peter!

Just try it: you’ve come up on the Lotto (or Lottery, or Euromillions, whatever) big-time. You’ll most likely have an initial splurge, but after that just what will you do all day? How will you spend the time and with whom? Where will you be? I recommend writing down your answers, no matter how outlandish they seem. If you want to take a break or sleep on it, that’s OK too.

Next comes the down-to-earth practical part: how can you bring elements of your answers into your life right now?

  • For example, if paying off your parents’ mortgage was on your Lotto list, that can represent you wanting to take care of them. You can do that in heaps of other ways that don’t need millions, such as spending more time with them, helping them with technology, or taking them on literal or conversational trips down memory lane.
  • Maybe you identified taking up a long-forgotten hobby such as ballet, painting, playing the drums, sewing or fishing. These pastimes might even have seemed onerous at the time (‘Oh Muuuuum! I don’t want to go to ballet class ever again!’), but you never know if you don’t give it a try. It could turn out to be a creative endeavour, physical exercise or just a great way to relax and unwind – or it could turn out to be a fulfilling passion you can indulge alongside work. See the artist’s example below.
  • Travel often comes up in the Lotto Wish List, and that’s something most of us can indulge – even if it’s not by private jet. Do your homework and cost out that trip: how many pricey nights out would you swap to turn that dream into reality?
  • Sometimes when the Lotto question comes up in coaching conversations, there can be answers that relate to helping others who are less fortunate. Again this is something you can do starting now, by volunteering your time and expertise, even if it’s only an hour or two a month. Check out Volunteering England for ideas and where to start.

Still not sure what you’d do all day if you won big? Then another approach is to get in touch with your values. Bringing your values to life each day is a great way to find fulfilment. You can identify your core values by simply reflecting on what’s really important to you; for more ways to explore them try this exercise.

Finally, I just want thank Alia al-Farsi for inspiring this post. At the weekend I had the privilege to meet this Omani artist, who worked in a government office for many years, studying and practising art in her spare time. Then in 2008 Alia quit her job, devoting herself to her dream full-time. This year Alia’s work will be at the Venice Biennale.  Find out more about Alia here. 


Dawn is the author of ‘How to be Zoomly at work’, available on Amazon


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