Goodbye, 2019: Journaling Prompts for Reflection and Intention

I have been working on a project recently that has involved poring through volume after volume of old journals I kept between six and ten years ago. It's been an eye-opening experience, as nothing shows you how far you've come quite like examining where you used to be.

There's a lot of colloquial advice out there, urging us to let go of the past and live in the now. Don't look back - only forward! I can appreciate the meaning behind these sentiments, but I cannot get on board with them entirely. While I do agree that dwelling on the past and steeping in regret probably never helped any of us all that much, I am a firm believer that healthy reflection on where we've been is one of our most powerful tools for future growth.

Why Reflect?

Many of us enter the new year with good intentions and big plans that border on grandiose. And while I don't see anything wrong with setting goals and looking toward where we want to be, I believe far too many of us neglect to really give the old year - the year we've just spent 365 days of our lives in - the send-off it deserves.

Do me a favor for a second: picture a big, beautiful, ripe, glistening, aromatic orange, sliced in half. Maybe by visualizing this alone, you can almost smell its perfume. Let's say you want that sweet, sweet juice. How do you get it?

You squeeze.

Reflection is like squeezing the orange to get to the nectar. When we reflect on a period of time, we are effectively extracting the good stuff. Each and every drop that falls is a gem of wisdom - wisdom that can lead us to small shifts and life-changing epiphanies alike.

But What If 2019 Was A Pile of Fresh Fuckery And I Want Nothing More To Do With It?

I've heard a lot of people talk about how rough 2019 was. Honestly? It was for me, too. It was most certainly not a carefree, easy, super-fun-happy-time year. But - and if you've been reading my blog and/or following me on Instagram for a while, you've definitely heard me say this before - there is so much value in the struggle. As delightful as it sounds to have a life that consists of nothing but sunshine and rainbows and fluffy baby animals, when the going is smooth, we're a lot less likely to be called to grow. To shift. To expand. The hard times, on the other hand, are what really teach us the things we need to know.

Our struggles are our greatest gifts, you guys. This may sound counterintuitive, but I am fully prepared to die on this hill.

What I'm trying to say is this: if 2019 felt like a rotting pile of rank garbage festering in the midday sun, chances are there are quite a few jewels buried in the filth.

And how can we find them?

We can squeeze the orange, as it were. Simply put, we can reflect.

Isn't Reflection Just Dwelling?

Not if you do it in a healthy way. Which brings us to the next question: what does healthy reflection actually look like?

Healthy reflection is not:

  • Shaming ourselves

  • Beating ourselves up

  • Focusing on our mistakes, failures, or perceived shortcomings

  • Thinking in terms of "shoulds" (as in, "I should have...")

Healthy reflection is:

  • Staying curious and open

  • Asking "what if?"

  • Focusing on what we learned

  • Being gentle with ourselves

  • Remembering that we've done the best we could with the tools we have

  • Asking "how can I use this experience to improve things moving forward?", how do I get started?

I'm glad you asked! Below is a list of journaling prompts - one set designed to reflect upon 2019, and another for looking ahead to 2020 with clarity and intentionality. Copy these questions into your journal, or click here to download a FREE printable worksheet!

2019: The Year In Review

  1. What are the most important lessons you've learned in 2019?

  2. What was the hardest part of the year? How did it serve you?

  3. What part of 2019 are you most grateful for?

  4. Who did you connect with?

  5. What brought you joy?

  6. What milestones did you reach? (Yes, even tiny ones, because our biggest achievements are made up of thousands of baby steps!)

  7. What emotions did you find yourself experiencing often?

  8. What did you not get that you wanted? How could it be good that you didn't get it?

  9. What held you back in 2019?

  10. What is your favorite memory from the year?

  11. How did you surprise yourself in 2019?

  12. Who were your heroes?

  13. What did you let go of in 2019?

  14. What did you call in?

  15. What do you wish you'd done more of?

2020: The Year Ahead

  1. What feelings and emotions do you want to experience more of in 2020?

  2. Looking back on the last question from the previous section, how can you integrate more of whatever it is you wrote down?

  3. If you could shift one habit, pattern, or belief to improve the quality of your life, what would it be?

  4. In what areas could you be more intentional in 2020?

  5. What do you need to let go of?

A Final Invitation

At the beginning of 2019, I decided to choose an Intention Word for the year, rather than setting a bunch of ambitious resolutions that I'd stick with for about three weeks, then completely abandon in favor of the comfort and familiarity of my old patterns. (Anyone else?)

At that point in my life, I was feeling stressed beyond belief, stretched in far too many directions, exhausted, and overwhelmed. I thought about what I really wanted to foster in 2019, and the word I eventually settled on was flow. Flow, to me, symbolized ease, peacefulness, and grace - all of which sounded positively divine.

Life went on, as it does, and in all honesty, I sort of forgot about my word for a while. I just went about my life, the same way I always had - until I had a mental health breakdown due to severe burnout. Out of sheer necessity, I had to take apart my life and rebuild it in a healthier, kinder, gentler way - a way that served me instead of harmed me.

It wasn't until then that I remembered my word. Oh, yeah - flow. And I realized that, even though it hadn't been on the forefront of my mind, flow had been making space for itself into my life anyway. I had planted the seed at the beginning of the year, and suddenly, six months later, there was more flow in my life than there had ever been before. It still wasn't perfect, mind you, because nothing ever is - but the improvement was astonishing.

This is what I love about Intention Words. They give us space to be curious, to stay open, to wonder - and often, even if we're not actively concentrating on them, they can help guide us from the background, providing clarity and direction where we otherwise might feel there is none to be had.

So, you are hereby invited to create your own Intention Word for 2020! Take some time over the next few days to think about it - and if you're feeling up to sharing, I'd love to hear what word you decide on! I'll be sharing my 2020 Intention Word on Instagram on January 1st - feel free to comment and share your word!

One more thought before I leave you to your day...

No matter how you feel about what transpired, or didn't transpire, in have done good work this year. You have grown. You have shifted. If it is not immediately apparent that these things are true, try squeezing the orange. Sometimes we have to dig a little deeper to find the buried treasure.

You're doing an amazing job.

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© 2020 by Ali Owens​