#117: The 21 Questions I’m Asking Myself This Week

This is my favorite time of year.

Not just because of the holiday cheer, festive mood and time spent together as a family. But also because of the opportunity to look back at the year.

This is a great time to pause and reflect. To take stock of where I am. What went right. What didn’t go the way I expected (and why).

For me, this process used to be pretty straightforward. I would simply look at my goals and identify what I accomplished and what I didn’t accomplish. And I’d then rush through a planning and goal-setting session for the following year.

Recently I’ve gone much deeper than that. As part of my planning process, I now read, journal, study, reflect and try to get away from my environment for a day or two. I’ve found this really helps.

This year I’m adding something else to the mix. I’m giving myself a series of prompts to guide this effort. These prompts are in the way of questions that will require me to focus my thinking and reflection.

I spent some time recently developing these questions. As I thought of more, I added to the list. And then, as I was wrapping up my final list, Tim Ferriss published a podcast episode where he detailed 17 questions that changed his life.

I found a few of his questions very relevant for me, so I incorporated my own version of them into my list. And after a few days of letting it brew, I came back to the list and did some trimming, editing and organizing.

I ended up with 21 questions. And I’m using them as journal prompts over the next couple of weeks.

As I answer these questions I’m quickly seeing how helpful this process can be. So that got me thinking: This might be helpful for you too!

I think you’ll find most of these questions to be fairly straightforward. But I’m going to spend some time in this episode discussing some of them in more detail. I’ll explain why I chose the question. And I’ll provide some context and commentary for a few.

The notes that follow are a very basic, unedited summary of the show. There’s a lot more detail in the audio version. You can listen to the show using the audio player below. Or you can subscribe in iTunes to get this show delivered straight to the Podcasts app on your smart phone, tablet or iPod.

  1. What am I most proud of this year?
  1. What are the most important lessons I’ve learned this year?
  1. What goals did I meet?
  1. What goals did I NOT reach? What stood in my way?
  1. Where am I still feeling stuck?
  1. What part did fear play in all this? (Note: check out my recent episode with Coach Jennie on this topic.)
  1. When I think about a typical work day, which activities do I look forward to the most? And which activities do I dread?
  1. What would I spend my time on if I was forced to spend only 2 hours a week on my business?
  1. What would I do if I inherited $50 million today? I would I work on? What would I try? What would I do differently in every role of my life?
  1. What 1 big project/initiative, if deployed properly, would have a massive impact on my business next year?
  1. Where (or on what) am I spending a disproportionally amount of time and energy, considering the impact or ROI I’m getting in return?
  1. What were my top 2 or 3 worries this year? And looking back, how productive was this worrying?
  1. What if slowed down my work pace dramatically for a week?
  1. How did I spend my free time this year? And what other leisure activities do I wish I would have spent more time on?
  1. How well did I take care of my body?
  1. How well did I feed my mind and soul?
  1. Which personal relationships need improvement?
  1. Whom do I need to forgive?
  1. What do I need to let go of?
  1. What do I need to STOP doing?
  1. How could I be nicer and kinder to myself?

BONUS QUESTION: What 5 habits do I want to develop in 2017? And what mini habit could I develop as the first step for each one?

Note: If you haven’t read it, The Power of Habit is one of the most important and fascinating books on the subject.

Mini Habits by Stephen Guise is also excellent and a very quick ready.

And James Clear publishes excellent content on this topic every week.

But I encourage you to noodle on some of these questions over the holidays. Use them as journal starters. I think you’ll be surprised by what you uncover.

This is the last episode of the year. I’ll be back with a best-of blog post next Friday. But in the meantime, I wanted to thank you for all your support over the past year! I appreciate all the comments, questions and feedback. And I appreciate your support (and sharing) of my message.

I have some really cool stuff planned for you next year, and I can’t wait to help you build a better freelance business.

I wish you a happy, peaceful and prosperous 2017!