The Art of Reflection: Transforming Insights into Action

2023 is coming to a close. 

I don’t know about you, but this year has been transformative for me. 

I moved into a home with my partner and our 5 combined pets.

I luckily avoided being laid off by my company.

I spent a combined 2 months traveling outside the country.

Hell, I decided to start this newsletter and create an entire business around it.

Even if you didn’t do all of that, I bet you still had a big year too. 

2020-2022 changed all of us, and 2023 was supposed to be a return to normal. Whatever that looks like.

And like any other year, regardless of the life events that occurred, I always perform a Annual Review. 

This process is amazing and provides me with an insane amount of clarity. And I want to share it with you, so you can pave the same clear path.

• Clarity on the changes that you have made.

• Clarity on the people in your life.

• Clarity for your new path forward next year.

But before you can gain that clarity, you have to ask yourself a few questions. 

For the next 3 weeks, I am going to share with you the questions I ask myself every year.

• Questions reflecting on the year behind

• Questions reflecting on the year ahead

• Questions on who I want to become

To kick things off, in this edition of Win Some | Learn Some, I am sharing with you my Annual Review questions to reflect on the past year.

And to make this even more exciting, I have a free copy of the Win Some | Learn Some Annual Review work book at the end.

Let’s dive in…

#1 What did I change my mind about this year?

Understanding what changed your mind can reveal how you’ve grown and adapted over the year. It’s the first step towards embracing continual learning.

Ever look back and think, “What was I even thinking?” I have. Plenty of times this year alone.

Reflecting on your 'aha' moments isn't just for laughs; it's more like admitting you were wrong without having to say sorry. 

Dive into what opinions or beliefs you flipped this year – bonus points if it's something more significant than wether to not pineapple belongs on pizza.

Think about it like a software update on your phone or computer. It is a necessary step towards improvement. Well, usually after a few bug fixes anyway.

Here is one to ask yourself, “What small habit did I change that a big impact on my life?”

For instance, my view on journaling shifted dramatically this year. 

What was once a sporadic activity mostly for stand-up comedy material has now become a daily practice of self-reflection. 

Shifting from sporadic to daily, has been transformative. 

How about you? 

Maybe you've had a similar experience, where something seemingly small transformed into a significant part of your life?

Ask yourself, “What software updates did I have this year?”

#2 What created momentum for me this year?

Let's talk about momentum. It's often elusive, isn't it? 

We're told it's crucial, yet it can be hard to grasp. 

In my experience, recognizing what drives us positively is key. 

For instance, when I embraced journaling, it wasn't just about writing more – it was discovering a strategy that brought clarity and focus to my days.

Ever say to yourself, “Man that was easier than I thought.” Or, “I feel really good after that.”

Those snapshots in time represent your real momentum. Take note of the next one.

For reflection, think of the things that got you rolling faster than a snowball headed downhill. 

What pushed you forward this year – a project, person, or maybe a newfound love for espresso shots? 

Identifying these can help you figure out if you’re on a roll or just rolling with it.

Momentum even on small things can bleed into larger things.

What did that for you this year?

Right them all down and then make a plan to do more of them in 2024. 

Much like my journaling example above, that small little thing gave me momentum and it had positive effects all through my life. 

Ask yourself, “Can I identify a habit or practice that consistently boosted my productivity or positivity?”

#3 When did I feel most out of my comfort zone this year?

Now that we’ve looked at what propelled us forward, let's examine what might have held us back.

Where did the wheels come off?

We all have those facepalm moments when things just fizzled. Pinpointing these 'well, that happened' times helps us learn, grow, and stock up on metaphorical spare tires.

Take a look at your calendar and identify what robbed you of momentum.

Was it a bad event at work?

Did you have some tragedy in your life this year?

Where did you get knocked down or shifted off your path to success? 

And when those things happened, did you course correct in real time? Or is that something that needs to be addressed in 2024?

Ask yourself, “What was the biggest risk I took this year, and how has that experience shaped my perspective or approach now?”

#4 Who were the boat anchors in my life this year?

Now, let's delve into a more challenging, yet crucial aspect. Reflect on the influences in your life. 

Were there people or situations that seemed to weigh you down? 

Understanding this can help you make empowering choices about your relationships and responses in the future.

So ask yourself:

• Who dragged you down this year? 

• Why? 

• What did you do about it? 

• What do you still need to do about it? 

There is a famous quote that says, “You are the sum of the 5 people closest to you.” If that is true, are those 5 people bringing you value and enriching your life? 

A few years ago I had a falling out with a friend. 

I made the choice and the events that happened after showed me that it was the right choice. After I made my thoughts and feelings about our relationship known, they ghosted me. 

And this was a very close friend, the best man at my wedding even. 

When things got real though, they just gave up. 

Kind of made my decision for me. 

And guess what happened? I felt better. I felt like I just shed a heavy coat that was always making me hot! I no longer had to put in lots of hard work to just have some social time with this person. 

While this was my experience, it’s important for you to evaluate your relationships.

Reflecting on the other people in your life can be just as important as self reflection at times.

The key lesson is recognizing and acting upon what truly serves your own well-being, a principle that applies universally.

Ask yourself, "Who in my life seemed to consistently bring negative energy or challenges, and how did I handle these interactions?"

#5 What did I NOT do this year, because of fear?

Here’s a thought that really resonates with me and might with you too…

When did you decide NOT to do something because of fear.? Imposter syndrome. Possibility of failure. Perceived lack of resources. All of these can stop you from breaking through to the other side. 

Here is another quote from someone I respect greatly, Micheal Hyatt…

“The best things in life are just beyond our comfort zone”

What he is saying is that you need to overcome a little bit of fear every now and then. Especially if you want to grow, achieve, experience new things. 

Do you remember the first time you rode on a roller coaster as a child? I bet you were scared. You may have even been pushed into riding by an older sibling or parent. They knew that your fear would subside and the thrill of the coaster would take over. 

And then what happened? You either loved it and wanted to ride more like I did, or you decided that’s not for me. 

Either way, you had to overcome some initial fear to figure out for yourself.

Ask yourself, "What opportunity or idea did I pass up this year due to fear or self-doubt, and how do I feel about that decision now?"

#6 What were my biggest hits, and worst misses this year?

This is straightforward, isn't it? 

Consider your big wins and losses. 

But here's the twist: delve into the 'why.' Write them down. Reflect. 

What fueled your successes? 

Conversely, what were the warning signs before a setback? 

Understanding these nuances can provide invaluable insights.

Our natural biases will distort our overall views on our past year. 

Optimists will remember the good more than the bad. 

For pessimists, its the opposite. 

Through this exercise, you can benefit from learning from both. 

Ask yourself, "What am I most proud of achieving this year, and what were the key factors that led to this success?"

#7 What did I learn this year?

And we come to the finish line. 

If you cannot think of anything for this, I am not sure how much of the above will help you either. 

Each and every day of your life is filled with learning opportunities. 

Are you seeing them? 

It can be easy to lose sight of your personal growth when you are in the trenches day in and day out. This is the time to look back and reflect on those lessons and the growth they brought to you. 

I learned a lot about my negative biases towards situations and people. My judgmental ways have probably prevented me from understanding people better. 

One thing I learned is to treat each and every new idea as a stand alone. 

What do I mean by this? 

Well, at work there are some people who I do not think too highly of. And past me would discount any idea they brought to the table. 

This closed mindset hurts me, not them. 

If you remove the person from the idea, then you are open to exploring all of its potential.

Ask yourself, "What is the most valuable lesson I've learned this year, either personally or professionally?”

Through our Annual Review, we've explored various facets of our lives, uncovering insights and lessons that shape who we are and who we aspire to be. 

Let's quickly recap the ground we've covered:

• Mindset Evolution: What did I change my mind about this year?

• Driving Momentum: What created momentum for me this year?

• Stepping Out of Comfort: When did I feel most out of my comfort zone this year?

• Influential Relationships: Who were the boat anchors in my life this year?

• Overcoming Fear: What did I NOT do this year, because of fear?

• Reflections on Success and Setbacks: What were my biggest hits, and worst misses this year?

• Lessons Learned: What did I learn this year?

As you close the chapter on 2023, carry forward the wisdom gleaned from these reflections. 

I encourage you to ponder these questions, jot down your thoughts, and perhaps share them with someone you trust. 

Use my copy of the Win Some | Learn Some Annual Review workbook.

Remember, the end of a year isn't just a conclusion; it's a stepping stone to a new beginning, rich with potential and possibilities.

And with that, I will see you next week for 7 forward thinking questions to plan for a great 2024!

• Get your free copy of the Win Some | Learn Some Annual Review (Link)

• A video on the power of reflection (Link)

• This video guides viewers through a process of breathwork and journaling, aimed at reflecting on the past year.(Link)

• This article discusses how self-reflection enhances self-awareness and improves decision-making (Link)