Pursuing Your Greatest Imaginable Challenge


Your Greatest Imaginable Challenge is the ultimate pursuit of an inspiring, significant and challenging goal, intending to be experienced over a long period, perhaps a lifetime.  It represents your personal Mt Everest to climb, from the initial base camp to the summit, and perhaps beyond, experiencing and relishing every milestone along the way.

Everyone has different levels of ambition which may influence the scale of the challenges people may choose to pursue. Still, it will nearly always be entirely personal to you, and your motivation to complete the challenge primarily comes from within.

To begin discovering what your Greatest Imaginable Challenge(s) might be, start by asking the following questions and documenting your answers in a journal or something similar:

  • What are you most passionate about in work and life?
  • When have you been at your very best?  What were you doing?
  • Where have you added the most value to yourself or others?

Expanding on these initial statements, consider the following:

  • What do you love doing most?
  • What aspirations have you had for your life, in the past and the present?
  • Ponder what exceptional talents you have that propel you to success, almost without fail.
  • How do you typically measure the value you deliver to yourself or bring to others?

After identifying your goal(s), it is time to take the second step and start your journey. Build momentum by taking one small action each day to make progress on your Greatest Imaginable Challenge, even if that is simply to spend 5 minutes reflecting on the joy you will experience reaching the objective. 

Achieve your Greatest Imaginable Challenge

  • Take three different coloured post-it notes and have a blank wall or table to display them on
  • For each coloured post-it note, write:
    • What do you love most? Your passions in work and life.
    • What do you do best? Your natural talent and skill.
    • Where do you add the most value? Your contribution to yourself or others.
  • Identify 6+ items for each category, and spread them out over your wall/table.
  • Randomly, or with some insight, combine all three colours into a Greatest Imaginable Challenge potential combination – what are you inspired to be, do, give back?
  • Reflect on your various combinations and identify ONE significant greatest imaginable challenge that you would like to pursue
  • Plan the milestones of your GIC
  • Take at least one action within 24 hours that gets the ball rolling.

Be inspired to achieve your goals

“Never, Ever Give Up” by Diana Nyad

At 64 years old, Diana Nyad achieved something never completed. A 100 mile straight swim from Cuba to Florida, on her 5th attempt! ‘Find a way. Want to reach your goal? Find a way’ is her legacy. 

Similarly, my role model for the achievement of Greatest Imaginable Challenges is my wife, Fiona.  While I have spent a lifetime investing in goal-setting and achieving processes, my wife seems to glide with ease from one significant achievement to another, smiling and laughing every step of the way.  Fiona made me realise the difference between a goal and an intention.  For many, a goal is a hope with a deadline in the future. For Fiona, her intentions occur when she envisions them.  There is no possibility of failure, as deep down, she has committed herself to the journey of achieving each intention.

What does a Greatest Imaginable Challenge look like?

The first example of this occurred when my wife woke up one morning in Edinburgh and, over breakfast, announced the fact that she intended to cycle from Land’s End to John O’Groats, the length of the United Kingdom from the south to the north.  At the time, my wife had a love of cycling (one of her passions). She in no way was cycling distances that might justify her commitment to cycle the length of Britain.  Very calmly and in a focused way, my wife set aside time each day to plan her training, her route up the country, accommodation for us as a family as we traversed the nation and even planning her daily diet to get her to the end.

At the heart of this Greatest Imaginable Challenge lay the following key elements:

  • Passion – Fiona loved cycling solo
  • Do Best – Fiona finishes everything she starts; once she put her mind to this end to end cycle, very little gets in her way.
  • Value – Fiona’s self-assurance is enhanced each time she accomplishes a new challenge.

Weeks of training and planning led to the start-gun in Land’s End, Cornwall, on the 23rd July 2007.  Every day my three-year-old Cameron and I dropped Fiona off for her day of cycling, and every evening we would pick her up to take her to our pre-arranged hostel or B&B, only to return the very next morning to her finish point from the night before.  Through scorching sun and torrential rain, Fiona plotted her way up the country one day at a time. 

We celebrated on the 2nd August when she crossed the border into Scotland and celebrated again on the 8th August when she and a friend rode into John O’Groats, in the northeast corner of Scotland.  Seventeen days of cycling, one day of rest, Scottish legs accompanied by a friend, the rest done entirely solo, for the sheer bliss of it, and to be able to say she had done it.


About the author

Christopher Miller

Christopher Miller

I am passionate about helping and inspiring small business owners to create their purpose, live their values and experience success, happiness and fulfilment by owning a business they can be proud of.
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