Working Out Loud Circle – Week Seven

This is part of a series of posts documenting my journey with a Working Out Loud circle, as defined in John Stepper’s book; Working Out Loud: For a better Career and Life.  You can read the rest of the series here.

Our circle was reduced to three this week, does that make it a Working Out Loud Triangle?  Still, as usual the discussion was an interesting & energising way to start Friday.

So what did we do this week?

Our routine is well established now, we spend our first minutes checking on progress since the last meeting, and hearing about peoples successes is a nice way to set the tone for this week.

Moving onto the exercises, we read through the ‘letters from our future selves’ and I was impressed with how the rest of the circle had done this. The letters seemed to have very definite visions of the future and some clearly defined pathways.

For me, this was the hardest exercise so far in the WOL journey.  I didn’t manage to achieve this before the meeting, and afterwards, I spent a lot of time struggling to get this down.   I pride myself on being able to ‘grind’ something out when it gets tricky, but a letter from my future self just seemed impossible.

We discussed the challenge, and the rest of the group were supportive – with their own experience as good input to helping me tackle this.  I’ve reflected hard on why I found this difficult, and I think it’s down to how I approach work as a whole.

I am usually very execution focused, my entire role revolves around taking vision and strategy and breaking it into small steps that mean I can constantly move forward.  Whilst I can contribute well to the vision, I have to see a roadmap and a plan – and this exercise didn’t take me there.

Apart from that, I never really make plans for my life – I pride myself on being agile and flexible and this ‘crystallisation’ of the future is not something I find easy.

We discussed how writing the letter is one thing, but reading it back was really powerful, and how we might share aspirations in our online profiles and world.


My key takeaways

  • Envisioning the future is not easy for everyone, but it can be a powerful tool.
  • Reading back your goals and aspirations can really increase the impact of the exercise.

What did I do after this weeks meeting?

  • Reflected on the difficulty I had in completing the exercise
  • Wrote a draft of the letter, which I’ll spend more time on the future
  • Resolved to ‘forget’ this weeks exercise  and look forward!


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