24 Questions to Help You Reflect and Plan for a Happier, Healthier and More Prosperous 2018

I started a new practice at the end of last year.

It involved asking myself a series of interesting and thought-provoking questions.

Questions that would help set the stage for my year-end brainstorming and planning session.

Last year’s exercise was so helpful in giving me clarity, I decided to do it again. And so I recently kicked off my year-end ritual with a similar set of questions.

Many of these questions are the same as last year’s. But I’ve included some new ones and edited others. I’m sharing them here, hoping they’ll inspire you to try something similar.

You might note that some of them border on being extreme. There’s a reason for that. When you exaggerate a situation, you almost always generate powerful new ideas and insights you wouldn’t have come up with otherwise.

If you decide to tackle some of these questions, take your time with them. Answer them in detail. (Hint: many of them are excellent journal prompts.) And use your answers to set better goals and commit to new habits in 2018.

Finally, I’ve created a handy PDF worksheet with all 24 of these questions. It’s an easier way to go through them. You can download that free PDF below.

Happy new year!

  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 episode with Coach Jennie on this topic.)
  1. What were my top 2 or 3 worries this year? And looking back, how productive was this worrying?
  1. For the goals I did not meet—or the areas in which I still feel stuck—how would I rate my effort level in those areas? (Be brutally honest.)
  1. If I could visit the future and look at my life one year from today … what would need to have happened this past year in order for me to feel happy with my results in this area (or areas)?
  1. What if I didn’t reach that result by this time next year? Could I find a way to be happy anyway? Why or why not?
  1. What would I do if I inherited $50 million today? What I would I work on? What would I try? What would I do differently in each role of my life?
  1. At the end of every week, do I typically feel happy, fulfilled and accomplished? Or do I typically feel behind on my work? Why?
  1. What one 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. If I landed in the hospital tonight with hours left to live, what would be my biggest regrets?
  1. What if I slowed down my work pace dramatically for a week? What would happen?
  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. How did I nurture and grow my most important personal relationships?
  1. Whom do I need to forgive?
  1. What do I need to let go of?
  1. How could I be nicer and kinder to myself?
  1. If I could call myself on the phone five years ago … and I had only 30 seconds to say something to my younger self … what would I tell him/her?

BONUS QUESTION: What ONE habit do I want to develop in 2018? If I could only pick one, what would it be? And what simple action could I take TODAY to kick start that habit?

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.