I started doing annual reviews back in 2017 after reading Nate Green’s annual retrospective. Since then, I’ve been influenced by James Clear, Tim Ferriss, and Matt Gray on their planning and reflection processes.

I say this every year, but damn, this year flew by!

Writing and using journaling for learning and reflecting is the most powerful habit I’ve cultivated over the years. Writing is something that is a clear thread through all the people I look up to and gives far greater clarity of thought. It’s a fantastic habit to reduce repeating the same mistakes.

When I interviewed Dan John, he noted the word research, means that we re-search the answers we have forgotten. He’s also been journalling for 30 years and makes a point to write down a mistake anything it happens so he learns.

Give yourself 60 minutes to go through this process. If you’re time poor, just focus on one of the 4 categories but in reality, these are all connected.

Here’s an overview of the annual planning

These are the 4 categories to focus your answers around:

  1. Health
  2. Wealth/Business
  3. Relationships
  4. Experiences

I’m going to split this annual review process into 3 parts:

  1. Fill out your energy calendar
  2. Answer the questions
  3. Map out your dream week and day

Let’s jump in:

Part 1: Energy Calendar

I got this idea from Tim Ferris:

  1. Grab a notepad and create two columns: POSITIVE and NEGATIVE.
  2. Go through your calendar from the last year, looking at every week.
  3. For each week, jot down on the pad any people or activities or commitments that triggered peak positive or negative emotions for that month. Put them in their respective columns.
  4. Once you’ve gone through the past year, look at your notepad list and ask, “What 20% of each column produced the most reliable or powerful peaks?”
  5. Based on the answers, take your “positive” leaders and schedule more of them in the new year. Get them on the calendar now! Book things with friends and prepay for activities/events/commitments that you know work. It’s not real until it’s in the calendar. That’s step one. Step two is to take your “negative” leaders, put “NOT-TO-DO LIST” at the top, and put them somewhere you can see them each morning for the first few weeks of 2022. These are the people and things you *know* make you miserable, so don’t put them on your calendar out of obligation, guilt, FOMO, or other nonsense.

Now that your clear on the activities and people that are giving or taking energy you’re in a better position to answer these questions.

Part 2: Annual review questions:

2023 was a massive year from a wins standpoint. A lot of things started to really take off from a business stand point.


  • Daily steps around 10k.
  • Fewer mouth ulcers this year.
  • Big improvements in stress eating.
  • Energy levels and mood very consistent.
  • Started working with a PT in person in Timisoara.
  • Maintained body composition around 12 % all year
  • Little to no injuries again this year. Very consistent training.
  • Started latin dancing which helped a ton with energy and mood.

Wealth/ Business


  • Spent time with my brother for 1st time in 4 years.
  • Got back to Ireland 4 times this year to see friends and family.
  • Connected with much more coaches online with collabs and podcasts.
  • Made good friends in Timisoara coworking community and dance school.

Xmas day swim in sunny Killaloe, Ireland 😛


  • Moved to Romania in April.
  • Met GMB crew in Madrid in June.
  • Went to first latin dance festival in November.
  • Lived in Las Palmas for the first 3 months of 2023.
  • Went free diving in Italy with my buddy Cathal in October.
  • Networked with Keegan Smith & uncommon success community.
  • Started studying Spanish for 30-60 mins 5 days a week from October.

Catching up with Ryan Hurst from GMB.io in Madrid.

Lessons from Wins?

The recurring lesson with all the wins has been embracing failure. This is the magic that has allowed all this to happen. Business is just learning from failures, starting free diving, dancing, and Spanish is being okay with the discomfort of failing and looking like an idiot repeatedly. This skill has made other parts of my life feel much easier by simply getting used to failure and discomfort.

Created energy?

Dancing was a huge source of energy that surprised me. It’s been such a nice addition to my lifestyle and a great way to socialize and travel. The impact of rhythm and movement is something I’m going to explore a lot more in 2024 and have a few people lined up to talk about this on the podcast. The therapeutic benefits of dance and rhythm is something I’m excited to learn more about more too.

Working in a coworking space was a big help from an energy standpoint also along with not traveling every month like I did in 2022.

Getting fresh air and going for a walk for 20 minutes at the local park in the morning phone-free was a big help along with staying off social media until after 11 am. Also, ensuring I worked out during the day had a big impact too.

Drained energy?

The big things that came up here were checking social media first thing in the morning, taking morning calls, and not having set breaks within the workday. When I have set breaks for a few minutes each hour and I train in the afternoon, I feel way better and I’m much more effective with work.

Unclear work boundaries were another draining activity. At certain points in the year, in particular the first half, I overworked a lot. I took no days off and felt way too busy and racing around.

Once I quit the other mentoring job I had in August, this gave me more control over my time again.

Where did I fall short/let others down?

I had some body composition goals that I struggled with this year. I have wanted to drop some body fat to get to under 10% as a goal but struggled with consistently staying on track with food for a lot of the year. This improved a lot when I moved to Romania and even more in the second half of this year. It’s something I will be in a better position to work on this year with more stability.

With the new staff, delegation is still something I need to improve as it makes everything much more efficient when I delegate, so that’s still an area to work on this year.

What would my 80-year-old self regret?

After this year, my 80-year-old self would be proud. This time last year the answer was to learn Spanish and dancing so even though I’m not as good as I think I should be, I’m so happy I’ve started the path of both of these activities. I’ve also heavily worked on community and relationship building this year which had been severely lacking over the years, so this is an area I’ll continue to work on in 2024.

Part 3: Map out your dream week and day

One of the big changes in my happiness over the years was realizing I had control to create my dream week, if I just took a few moments to figure out what that would look like. You have much more control over this than you might think. And what I find is if you’re on autopilot mode, your days will get filled up with social media and Netflix, and you’ll be frustrated that you’re never doing the things that make you feel better about your life.

My Dream week example:

I want to stick to themed days this coming year where I have a clear goal of each day for the business. The weeks where I focus on one task each day, I get so much more done with less overwhelm. When I get into a cycle of trying to do too much, I end up half doing a lot of things and not finishing tasks.

I also want to stick to a full day off on Saturdays and leave Fridays more open than they have been so I’m not trying to cram stuff in on Fridays.

My dream day example:

This has become more and more consistent over the last few months of 2023. This layout of the day has worked really well when I stick to it.

Here’s the file to download all the tasks I walked through today so you can create your own annual review and dream day/week.

I hope you’ve found this annual review helpful and find clarity in doing this process for yourself.