End of Year Reflection Questions

One time a friend asked on social media “how do you know if therapy is helping?”

I think of that every time I prepare for a Reflection Session at the end of my coaching package, Painless Productivity. I never want one of my clients to wonder whether coaching was helpful for them—much less to not even know how to tell if it was helpful for them!

So in the final session of the package, my client and I look back at how far they came, and then look forward at how they want to carry their progress into their everyday life.

I find this kind of reflection important in my own life, too. I don’t want to just float through the year without taking stock of what happened and consciously planning what I want to do next. It doesn’t necessarily have to be about self-improvement and New Year’s Resolutions. The important thing is just that my eyes are open, that I’m watching the passage of time, and my own personal evolution.

Even when you’re not in coaching, therapy, or other dedicated personal development work, you’re still growing and developing. Each year contains many moments of challenge, insight, and breakthrough. So I think my reflection questions can apply to the end of our year, as well.

So, join me in an End of Year Reflection!

Since I don’t have notes about how your year went, I’ll give you some end of year reflection questions to jog your memory. I’ll ask about the year for simplicity, but I suggest thinking back through the seasons or the months to really access your memories from the entire year.

Review what you learned

With clients, my first end-of-package reflection question is about learnings, so that they can remind themselves of those learnings and hold onto them better.

• What did you realize about yourself this year?
• What did you learn about life this year?
• What did you learn in your area of expertise this year?

Celebrate your accomplishments

Too often, those of us with a perfectionist streak are always chasing accomplishment, never seeming to catch it. Because as soon as we catch it, we think “well, this isn’t actually good enough. I need the next thing.” So, although there’s more to life than accomplishing things, I think there’s something really healthy about stopping to notice what you did accomplish.

Now, I know some of you are going to have a hard time filling out this section with accomplishments that don’t feel “big enough.” So feel free to tell your brain that in order to get an A in this End of Year Reflection, you have to count things even if they’re small. You can use that overachiever energy for good.

• What projects did you finish this year?
• What did you quit or say no to, knowing it was the right decision?
• What did you get better at this year?

Form your end of year narrative

At this point, I share my own narrative of what unfolded in the coaching package, using my background knowledge about parts work to boil down all the detail into an overall arc. Then, I ask the client to respond with their own narrative. My narrative is, I hope, helpful input, but ultimately we each have to form our own understanding of ourselves and our lives. Since I can’t tell you about your life in a blog post, you’re on your own here, but again, I’ll give you some prompts to help you get started.

• What were your primary struggles this year?
• How did you grapple with those struggles?
• How did grappling with them change you?
• Where are you in those struggles as the year ends?

As my coaching teacher Steve March says, we always begin and end a session “in the middle of life.” And it’s the same with years. There’s nothing wrong with coming to December 31st without having solved all of your problems. It’s the taking stock that counts.

Reflect on what’s next

Regardless of whether the client chooses to continue coaching, we discuss what habits they can weave into daily life to maintain the progress we’ve seen, and what goal they want to work towards next. You can do the same!

• Given where you landed in your current struggles, what is your next goal?
• What step do you need to take next to work towards that goal?
• What’s a small daily habit that could help you work towards this goal?

This habit can be directly or indirectly related to your goal. For instance, if you have a goal to write a book, a directly related habit could be to write a little bit each day. An indirectly related habit could be to spend five minutes each morning deciding on your top priority for the day, because you know that if you get your top priority done by 5pm, you’ll be willing to write in the evening. Indirectly related habits can often be short and sweet, which makes it easier to adopt them.

To choose a habit that can stick:

• set up a reminder for it. This could be an alarm on your phone, or something natural like putting the book you want to read in a place where you’ll see it.
• remove obstacles to doing it. If your habit is to journal, make sure you have pens handy. If your habit is to exercise, pick out your gym clothes.
• make decisions about it beforehand. By the time you commit to the habit, it should be crystal clear in your mind what you’re asking yourself to do. The more decisions you have to make at game time, the harder it will be to follow through.

Do you want to make next year different?

As you review your year, you may end up with beautiful goals for next year. And, we all know that it’s really hard to stick with those goals. In fact, the second Friday of January is known as “Quitter’s Day,” because there’s some evidence that most people quit their New Year’s Resolution by then.

So join me on Quitter’s Day — January 10th in 2025 — for Productivity Office Hours. I’ll help you work through whatever you’re stuck on so you can keep putting your hard-won 2024 insights into action in 2025.