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Guided Exercises That Can Help You Evaluate Your Life in Your Writing Journal

by Jacki Andre July 19, 2020

Guided Exercises That Can Help You Evaluate Your Life in Your Writing Journal

I'm closing in on the half-century mark and I'm still seeking my true purpose. How about you? 

Do you wonder if you’re reaching your full potential? Do you do something every day that brings you joy? What do you dream about? Early retirement? Cruising in the Caribbean? Starting a family? Joining a roller derby team? Running away to be a tambourine girl for Jim Cuddy? (Wait. That’s probably just me.)

I have a dear friend (and distant cousin) who takes stock of her life at each birthday. What has she achieved in the past year? Where does she want to go in the next year? As for me, on my big day, I just eat cake. (With buttercream icing, thanks very much.) I’m not good at pondering life’s big questions at the best of times. Give me the option of considering whether my five-year plan is still viable or eating cake while scrolling through my birthday wishes on Facebook, and the latter choice wins every time. Because. Cake. And also: I don’t have a five-year plan. I don’t even have a five-DAY plan.

A goal without a plan is just a wish.
Failing to plan is planning to fail.


Yeah, yeah, yeah, yeah, yeah. I’ve heard. Whatevs.

I don’t feel like my life is a study in mediocrity, due to a lack of goals of planning. Nor do I feel like I’m stuck in a rut. Still, I could probably use some direction. Am I living my best life to the fullest? Do I have untapped potential? Do I have to take tambourine lessons to join Jim’s band, or can I just *ahem* shake it?

Maybe I should think about these things.

The fine folks at wellcat.com encourage ALL of us to think about these things.And, in fact, they created “Evaluate Your Life Day” for this reason. The occasion is celebrated annually on October 19. (Which means I can limit the deep questions on my own December birthday to: “Which buttercream icing tastes best on chocolate cupcakes? Chocolate, cherry, or mint?”)

What’s the Point?

Don’t ask me. I’m a newbie with this philosophical stuff. Oh. Wait. Right. The point of “Evaluate Your Life Day.” THAT, I can help you with.

Taking some time to evaluate your life can provide a lot of clarity. It can help you identify things that you would like to change or improve. It can also provide a chance to pat yourself on the back and realize that there are things you are already happy with.

Evaluating your life can also help you articulate your dreams. Sometimes dreams are so big and seem so unfathomable that they can be difficult to verbalize. But articulating your dreams can help you understand and refine them. Is my dream about being a tambourine girl for Jim Cuddy actually about running away from my current life? Or, is it about being brave enough to get up on stage? Or, is it just about enjoying life by going to more concerts? Once we articulate and finesse our dreams, we can start working on goals to achieve them. And who wouldn’t want to live out their wildest dreams?

Sasha Graffagna at SuperheroYou explains that when you evaluate your life you can then transform yourself “physically, mentally, and spiritually … using your newfound knowledge to make the world a better place.” Sounds pretty amazing, doesn’t it?

The ONE Question to Start With

There are a ton of possible questions to ask during this exercise. But one has the power to unlock all kinds of insights and to give voice to your dreams.

A number of bloggers, including Sasha Graffagna, Shawn Lim over at Stunning Motivation, and Rosalie Bardo at Elite Daily suggest imagining that today is your last day on earth. The question then is two-fold. First, how would you want to spend your last day? And, second, what will be your legacy? What do you want to be known for? What will people say about you once you’re gone?

This set of questions would bring up a lot of other things for me to consider, like:

  • Am I happy at my job? Would I want to spend my last day there?
  • If I knew it was my last day and I could plan to do anything, what would I do?
  • How are my relationships with the people I spend time with?
  • Have I made a positive difference in the world?
  • What dreams do I want to achieve before I die? What’s on my bucket list?
  • Do I have regrets?
Other Questions to Consider

There are a ton of websites and blogs with suggestions on how to evaluate your life. Take some time. Google them up. Find the questions that resonate with you. Some of the questions that I would love to reflect on are:

  1. Did today matter?
  2. What do I run from? What am I afraid of?
  3. Do I trust myself?
  4. How often do I step out of my comfort zone and in what ways?
  5. How do I stand up for what I believe in?
  6. Am I happy? What I can do to find more joy?
  7. What are the top five lessons I learned in the past year?
  8. What’s missing from my life? How can I fill that void?
  9. Am I doing enough creative things? What would I like to create?
  10. What kind of self-care am I practicing? Is it sufficient and effective?
How to Explore your Questions

You had to ask? Pfft. Break out your writing journal.

Cracking open a cute notebook and jotting down your thoughts will help you delve deeply into this exercise. As I explained in a blog about working through grief in your notebook, writing journals “provide a safe space where we can express ourselves openly and honestly, without fear of judgment. They give us a place to say those things that we would struggle to put into words or have difficulty saying.”

Choose a question to focus on and then practice stream of consciousness writingDon’t censor your answers. Don’t make corrections. Don’t worry about spelling and grammar. Just write freely in your notebook. This style of writing is proven to help self-awareness and provide clarity.

If you’re getting bogged down and beating yourself up over things that have gone wrong and dreams that are still unfulfilled, try writing yourself a letter instead. Pretend you’re writing that letter to a friend. Writing in this manner can help you be more objective, non-judgmental, and compassionate towards yourself.

Whatever tack you take, it’s important to write. As Kent Healy points out at The Uncommon Life:

passively thinking is not the same as writing. Retention, creativity, and engagement is higher when physical activity is required. [Y]our notes will serve as a map and source of inspiration for the duration of the year.  And [also], your notes will be important to review when looking back on the year.

Next Steps

So, you know what you’re happy with, what you want to change, and what your dreams are. Good job! But: how do you start the ball rolling towards a better life?

One suggestion: use a vision board journal. In a terrific piece over at Goddess Provisions, Kristen Hess explains:

Putting energy into a vision board will not only help you get crystal clear on what you want to create in your life but will also make your dreams become more actionable. … Having a visual reminder will help you stay focused and your vision board will also act as a benchmark for which you can measure your progress.

I have never used an actual vision board myself, but I have had a vision board journal for years. I like how easily new dreams and goals can be added. I have one page for different themes: places to travel, bucket list items, financial goals, health goals, etc. I like the privacy of it and how easy it is to tuck it away when need be. It’s also easier to flip back through it and see the progress that you’ve made. And finally, as Kristen points out, it’s highly portable.

So there you have it: that's  how you evaluate your life. I just might give it a whirl myself, on Evaluate Your Life Day. But, first: cake. With buttercream icing.

Photo by Jeff Sheldon on Unsplash

Jacki Andre
Jacki Andre

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