The 5 End of the Year Questions That Will Transform Your Life

• 5 min read
The 5 End of the Year Questions That Will Transform Your Life

How To Automate Your Life

This is the second part in a series of how to do an annual review. If you want check out my first newsletter that talks about it, you can find it here.

Today we are going to talk about the annual reflection --it's a better name than annual review (thanks Jen and Donna for the suggestion).

Last week I asked you to answer the following question:

What would your future self (10-year older version) think about the life you're currently living? How about the 20-year older version? 40-year older?

I've modified the question since to this:

What would 10 year old me feel about my past year? What would he advise me? What would 100 year old me feel about my past year? What would he advise me?

It's simpler, but it also makes it more clear what the intention of the question is. You are calling on the wisdom of your past and future selfs to reflect with you. During reflections it's helpful to have an outside perspective that puts your year into context. You may find that you are too hard on your yourself, or that you're distracting yourself with achievements instead of living. Asking your old self and your young self what you thought about the year gets you to reflect in a deeper way.

After I answer that question, I reflect on and answer the following 5 Questions...

  1. What did my year look like in terms of metrics? (health & mood, personal finance, screentime, routines, etc)
  2. What did I achieve? (Bold the most valuable and feel f**king proud).
  3. What was the 20% that delivered the 80% of my results this year? How can I double down on that 20%?
  4. What were my disappointments? What did I learn?
  5. What was my bottleneck (the answer is almost never time)? How do I address the bottleneck?

Let's quickly walk through them.

  1. The first question helps me jog my memory. This year was especially long and it's important to remember what really happened in the year. Often my thoughts about what happened don't match up with the reality.

    I tend to look at how I spent my time (using, my finances (using copilot), and my mood/routines throughout the year (using It allows me to understand the year on a day-to-day, intimate level. I usually try to spend some time figuring out when my most productive happy days were. I also make note of when my sad, non-productive days were. Both of these are useful to think about as I move through the questions.
  2. The second question is essential in allowing myself to feel my wins. Too often we don't allow ourselves to feel proud of our accomplishments. To see what you've done in a year on paper is really fun and really heartening.
  3. Then it's useful to figure out... what is driving those accomplishments? How can you I more of that? When I hone in on exactly what drives those results I am able to double down on my past year's strengths in the future.
  4. Next it's useful to think about your disappointments. I like the word disappointment because it brings your feeling into the mix. If something is disappointing it's something you want to think about more deeply.
  5. Then the last (and I think most important) question in the annual review consists of figuring out what your personal bottleneck is.

    The bottleneck is the one place in your life that's preventing you from being your best. Here's a picture to demonstrate what I'm talking about...

It's like when you have a knot in your garden hose. You can turn the water all the way up, but it won't change the water flow much. The only thing you can do to have the water come out fast is to untie the knot.

Personal bottlenecks are the knots in your life that are preventing you from being great.

Often we think that we don't have enough time to become great in our life. But if you look closer it's almost never "time" that's the problem. Usually you lack courage, a good system, or aren't trying hard enough to come up with a creative solution. The point of this question is to make sure you know front and center what your bottleneck is and what will be the biggest place for personal growth.

You don't want to be like the wannabe entrepreneur who reads a bunch of books, gets good at time management, and learns a bunch of skills...But doesn't work on the one thing that's preventing them from creating a  startup--their courage.  

If you still don't understand what a bottleneck is, email me. It's one of the most useful personal growth concepts I've learned.

And that's it! After answering these 5 questions you now know what you should do more of, what you should less of and what specifically you need to work on for the next year.

This week, book an hour to think about these questions. Trust me it will level you the f**k up.

Then next week, we'll be talking about how to actually achieve your new year resolutions (spoiler: you have to abandon resolutions and build systems instead). See you here next week.

Be More Alive

I'm going through this annual review with you all!

Last week I asked myself this question (referenced above):

What would 10 year old me feel about my past year? What would he advise me? What would 100 year old me feel about my past year? What would he advise me?

Here's my answer:

10 year old me would tell me not to forget to play. He would remind me to have fun. To spend time with my friends and my family. The profound part of my 10 year old self would also tell me to be more open and not prevent myself from really experiencing connection.

100 year old me would emphasize focusing on being more alive. Not being so hard on myself and reminding me that if I put in the work (the inputs) then the outputs will happen. He would also remind me that courage is one of the most important qualities for getting what I want. He would tell me to recognize what really matters in life and to sacrifice the good for the great. Most of all he would advise me to trust my preparation, trust my process, and trust myself. The future is chaotic, uncertain, and full of suffering... this much is true. But I have to believe that I can deal with it (because I can and because it's a self fulfilling prophecy).

Both would advise me not to let the future moments of profundity, presence, aliveness, intimacy pass me by. They would remind me to live within those moments, to sip deeply because those moments don't come often in life.

We are often so afraid of being sad in the future that we forget to notice that we're happy now.

And well, writing this letter to you...

I'm happy now.


← 5 Steps To Achieve The Best Year of Your Life
2 Quick Questions You Need To Ask This Week →

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