Reflecting with YearCompass Pt. 1


Introspection is a super power.

“The definition of insanity is doing the same thing over and over again, but expecting different results.” -Albert Einstein

To become more conscious of the traps you fall into, it’s helpful to have a journal. When you read through your old journals you will likely notice that you still have some of the same problems you were dealing with then. This experience can be painful. But that pain might be just what you need to make a change.

After a couple years of sporadic journaling, I was open to the idea of a YearCompass. YearCompass has you review your calendar for the past year and pull out key events, good or bad. I would also recommend that you flip through the photos you’ve taken from the past year.

Afterward, it asks you a series of questions to translate all of these thoughts into concrete takeaways and plans for the upcoming year. This part goes by quickly, especially compared to the ~4 hours you might spend going through your calendar and photos.

The magic of the YearCompass comes when you enter year two and beyond. You can review and see which of the goals you’ve achieved, what you’re still working on, what you’ve abandoned, etc.

2019 was my second year completing YearCompass. It has been wild to reflect on everything that happened in 2019. I honestly couldn’t believe all of the events that happened in the same year.

And I still missed most of the aspirations I had outlined in the box labeled DARE TO DREAM BIG. At least no one can doubt my ability to dream.

Dreams that I planned for and realized in 2019:

  • Wrote and published a book
  • Went to Oktoberfest
  • Made friends while abroad (in: China; Warsaw, Poland; Sofia, Bulgaria; Barcelona, Spain; Tel Aviv, Israel…and more)
  • Invested a small amount of money in $BTC

And I didn’t:

  • Win the German Chancellor Fellowship
  • Spend a week skiing in the Alps
  • Get an A in my marketing class
  • Get 1,000 followers on Twitter
  • Write 20 blog posts
  • Meditate for 100 hours
  • Deadlift 315 pounds
  • Date many beautiful German women
  • Achieve near fluency in German (from all the dates mit schönen Frauen!)
  • and oh so much more…

I missed out on most of my big goals but 2019 still might have been my best year yet. I don’t know if the YearCompass played a role in that, but in the pursuit of a great 2020, I’m looking for all the help I can get.

If you have some time, I’d encourage you to complete your own YearCompass and consider inviting a friend by sharing this post. I’ll be writing up a few more reflections from 2019 over the next couple days.

Thank you for reading! If you want to support me on my current adventure, please consider purchasing a copy of Lead The Future, leaving a review on Amazon, joining my newsletter, or helping me to secure speaking opportunities in-person or on media platforms.


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