Living to Learn
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Living to Learn

Becoming the CEO of You: Conducting a Monthly Review

Photo by Isaac Smith on Unsplash

When you are on the journey to becoming the CEO of you, one of the most important items to have in your toolbox is taking time to reflect.

Why reflection is important as it allows you to unpack and assess where you are at and where you want to go. To look at your experiences and see what insights you’ve gained from them. Most importantly, taking the time to engage in a monthly reflection allows to gain insight and meaning from what you are doing and see if all that doing is moving you towards a life you love or further away from it.

It is important to note that if you haven’t done a monthly review in the past, it can feel a bit overwhelming. Remind yourself that you are on a journey to becoming the best version of yourself and that to do so you need to be curious and designer-ly in your approach.

What do I mean? When you embrace curiosity you put yourself in the position of asking questions about why things did or did not work and to adopt a mindset that life is a constant evolution of designing and making adjustments what could be changed to help you be more successful. By adopting this approach you also stop seeing everything as a pass/fail and more as an opportunity to learn and grow.

If you are doing daily and weekly wrap ups, this also becomes a much easier process as you can quickly pull the reviews forward into your monthly review.

Monthly Reflection Questions


  • What is my #1 personal accomplishment?
  • What is my #1 professional accomplishment?
  • What were the big events of this month?
  • What were the key things I learned?
  • What moments that I want to remember?

Level 10 Life

Level 10 Life is one of my favorite tools for getting a handle on the areas of your life that are most important to you. By tracking how you are doing in each of the areas, you start to paint a picture of where you need to focus more attention and what activities that you are doing are helping or harming that area of your life.

Questions to ask:

  • Where do I sit in each of my 10 areas?
  • How does this compare to where I was at last month?
  • What activities did I do that moved up my ranking in a particular area?
  • What moved down my ranking in an area?


This exercise should function like a brain dump. On a piece of paper, write the words “start”, “stop”, and “continue” spaced apart on the page. You want to have enough room to right any and all thoughts that come to mind. Set a timer for 10 minutes and write down what parts of your life you would like to start, stop or continue something when thinking about each of your level 10 areas.

Habits and Routines

I’ve said it before, but it is worth repeating: habits and routines are the foundations of success. If you want to well positioned for success and not feel like you are constantly swimming against the current, you need to cultivate habits and routines. Having these in place helps accelerate your progress and steers you into the flow of progress. Ask yourself:

  • What progress have I made against my habit(s) this month?
  • What roadblocks did I encounter?
  • What routines do I have in place?
  • What worked or didn’t work about that routine?
  • What parts of my life could benefit from a routine?


Reviewing your calendar for the upcoming month at this stage is helpful as it gives you a clear picture of how much time you are going to have to dedicate to your goals and projects. I used to do this at the end of my monthly review and quickly became frustrated as I would find that I had to then go back and revisit each of my goals and projects again to adjust them to the time I had available.

Questions to ask about your calendar:

  • What birthdays, anniversaries or celebrations are coming up?
  • What does the school calendar look like for this month?
  • What does the kids sport schedules look like for the month?
  • What big work events do I have coming up this month?
  • Are there appointments I have or need to schedule?
  • Where do we have evenings where cooking dinner will be a challenge?

Goal Progress

Your big, audacious goals take time and dedication to make happen and it is critical that you take the time to reflect on your progress. As your goal is probably something that you’ve never done before, reflecting on your goals also allows you to see what you learned in the past month. During this reflection, you might find that tasks you thought you needed to do actually aren’t important for you to do, aren’t important right now, or that you already accomplished by doing something else.

  • Did I accomplish the tasks I had for my identified goals?
  • Which tasks did I not do? Why?
  • Are there tasks that I need to add for this goal? If so, where do they fit?
  • Are there tasks I need to remove or adjust? If so, why and where?


Projects are items typically related to work or household items that you have. Ask:

  • What projects are next up?
  • What projects are in progress?
  • What projects are up next?
  • What are the key tasks against that project?
  • When do I need to have these tasks done by?
  • Do the tasks depend on others to get done?

Career Review

This is something that most of us do twice a year for mid-year and year-end performance reviews. Unfortunately this approach puts considerable stress on you during these times to remember everything that you did, obtain feedback, and wrap up goals that you had for the year.

Instead of cramming this into a frenzied twice yearly activity, check in monthly with yourself and those you work with. It not only keeps you on track, but elevates your impact. Make sure that the responses to these questions get documented and you update whatever performance trackers you might use.

  • What were the top things I accomplished this month?
  • What did I learn from these accomplishments?
  • Were these accomplishments aligned to my work goals and priorities?
  • What roadblocks did I encounter?
  • Where do I need training or mentorship?
  • What did I do to build my network?
  • In what areas can I work smarter, not harder?
  • What 2–3 skills do I want to strengthen?
  • What risks can I take that would make me bigger and bolder?
  • What are the priorities for my group and the company for the next month/quarter/year?
  • What is my #1 priority for the upcoming month?

Keeping Track of Your Reviews

Ideally, you should keep track of your reviews all in one location so that it is easier to look across them month over month. However, you might find it easier to keep your personal items in a notebook or bullet journal and your work reflections in a file on your computer and within your performance system.

Don’t stress too much about what this location is or if it is setup correctly. The key is to get started and then keep doing on a monthly basis. Go ahead now (yes, right now) and schedule time this weekend to do your monthly review and to get on your calendar next month’s review. Your future self will thank you!

If you’re new here…

We are on a journey to helping you Become the CEO of You so that you can become the best version of yourself. Over the course of the month, we’ll cover knowing yourself, creating goals, adopting mindsets, embracing habits, and practicing self-care. You can find all the posts in our publication Living to Learn. You can also find my random musings on my personal page here.



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