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Probing Questions to Reflect on 2020

Probing Questions to Reflect on 2020
In this episode, we answer some reflective end-of-year review questions. We introspect about new ways we've had fun in 2020, new ways we've suffered in 2020, and what lessons we'd teach to others.

In this episode, we answer some reflective end-of-year review questions. We introspect about new ways we've had fun in 2020, new ways we've suffered in 2020, and what lessons we'd teach to others. Enjoy!

The list of questions that we discuss were as follows:

  • How did you have fun differently in 2020?
  • How did you suffer differently in 2020?
  • What kept you up at night with excitement this year? Was it worth it? Would you want to do more of it?
  • If you had to teach one thing that you learnt this year that would improve one’s quality of life, what would it be and why?

Here are some of the other highlights from our discussion:

There is always a big difference between how well you can evaluate the art and how well you can produce the art. We can all evaluate what good piano playing sounds like to a much greater extent than we can actually replicate that sound. This difference, between knowing what is good and recognising what you can actually produce, induces a level of discomfort that dissuades many people from continuing to develop their skills in a particular art form such as playing an instrument.

Dealing with colleagues at work can be difficult especially if that colleague is in a senior role and addressing the issue would require directly confronting them about your concerns.

The way that we think about things in terms of positive and negative is quite reductive to the point where it loses its utility. It misses out on some valuable nuance which is outside of simply giving something a score out of ten.


If you want some extra questions that you can ask yourself as we reach the end of the year, then please subscribe to Ali’s weekly newsletter, Sunday Snippets, which you can sign up to here. Here are just a few of the questions from the latest email:

  • What people/kind of people did you spend less time with in 2020?
  • What people/kind of people did you spend more time with in 2020?
  • What did you feel guilty for in 2020?
  • What 3 people are you the most grateful to in 2020 and why? How can you thank them? How can you find more people like this in your life?
  • What have you learnt about the way that you deal with uncertainty in 2020?
  • What new habits did you create in 2020? Which ones would you want to keep?
  • Did you feel you spent enough time with your family/significant other in 2020? How would you change this in 2021?
  • What things did you stop caring about in 2020?
  • What new thing did you spend a lot of money on in 2020?
  • What new thing did you spend a lot of time on in 2020?
  • What do you feel you’ve gotten a lot better at in 2020?
  • What did you rediscover pleasure in in 2020?
  • When you felt at peace this year, what were you doing?
  • Which of last years goals did you not achieve? Why did you not achieve them? Will you carry them on to 2021 and if not why?
  • How much closer are you to your “by this age” milestones (if you have any)? Do you find yourself caring less or more about these?
  • At the end of next year, if you are drastically exceeding your expectations, what would you be doing?

This episode is kindly supported by Skillshare. Sign up at skillshare.com/notoverthinkingpod.

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