40 Self-Reflection Questions I’m Asking Myself Every Year.


After a year long academic hiatus, I am back! Thank you to all who have supported my year of magical thinking at Oxford. A year really gives you a long time to think and think, I have. A dear friend this year passed this list of questions to me called a ‘general life examination.’ At the time I had no time to answer them. So I stuffed the list safely into an iPhone note and thought— ‘someday’. But as I hit the submit button on my 12,000 remaining words left for my theology degree, I slammed the computer shut and thought about the list . The weight of all of that hard-won transformation, pain, heartache and joy caught up to me like someone hit the fast forward button on a VHS tape of the past year. I didn’t sleep much for the next 3 nights. My mind was like a giant paper jam of ideas, emotions, nostalgia and ecstatic gratefulness. So, one of those sleepless nights, I pulled out the questions and wrote them down in my journal.

It might seem surprising to know that journaling is a relatively new practice to me as a writer. About five years ago, I stopped keeping a daily record of my thoughts. Why? I felt annoyed of myself. Annoyed like when you hear the sound of your own voice playing on a recording and you think— ‘Really, is that me?’ Reading what I’d written down felt like a chore. Like navel-gazing. Like an irritating checklist task that I’d rather not do. Because I write for work, sometimes that margin of reflection gets lost to a client project or something else I’d rather do, or the laundry needed switched over so I couldn’t finish that thought. So I shelved the whole journal thing, even though every year, people gave me a new journal on my birthday, and I said thanks and threw it on top of the empty stack I already had.

But in 2019, I broke open the page again because I had something to say.

Sometimes you don’t right now, and that’s okay. When that sense of burnout happens in your vocation or personal life, you will know it. It will feel like nothing you have to say works. Like it’s falling flat, or that someone has let all the air out of your tires. You might go through a health crisis or a bout of apathy or just feel a general angst rising up in you. You’ll get so much writing advice that says— ‘go to war with writer’s block!’ ‘don’t let it win!’ Dry seasons happen, but barring a deadline, my unconventional little piece of advice is just to go with it. Dig into a newer, more richer undiscovered aspect of life. Let your mind rest. Shelf the journal. Come back when you are ready.

So this September, journal or no journaling practice, I’ve committed myself to doing this annual general life examination. I encourage you to join me for a year-in-review of your most impactful moments. And whether or not you are working on writing a memoir, you should do it. The reflection process allows us to slow down enough to appreciate the big heavy rocks we moved around in our lives, whether those rocks were fears, doubts, insecurities about ourselves or the opinions or others, or old life scripts that we no longer allow to play in our minds. Whatever it is, I encourage to adopt some kind of process that works for you. This works for me and so I am sharing it.

Five categories are covered in the life examination: spiritual, physical, relational, emotional, and vocational. I like only having to review the last year because you can go into more detail. Use your morning quiet time to answer them in your journal, or do it in the evening before falling asleep. Slam the list down next to the coffee pot the night before if you have to. Also, don’t make the mistake of waiting until December to do this. Holidays are a notoriously chaotic time of the year and you may not have the space you need to it done. September is a great month because it’s calm and that’s when the sweaters come out from under the bed, things slow down a bit , and you can sip a hot drink without overheating .That’s all. Enjoy these and write me with how it’s going!

General Life Examination

  1. What are the most important events that have happened to me or in me this year?

  2. What are the greatest breakthrough’s in any category of life this year (i.e. physical, emotional, relational)

  3. What has been the greatest struggle for me this year?

  4. What has been my greatest and deepest loss this year?

  5. What area has consumed my thinking, attention, or focus?

  6. In what area of life did I feel the most vulnerable, the most naked and susceptible or exposed? Was that a good or a bad experience?

  7. Where have I most experienced the presence of God in this year?

  8. In the last 12 months, what area of life have I experienced the greatest sense of consolation (i.e. peace, happiness, contentment, security)?

  9. In the last 12 months, where have I felt the most desolation? (i.e. pre-occupation, distress, sadness, depression, fear, brutality).

  10. What one word sums up this year?

Section 2—Physical/Mental Health

  1. What 5 words best describe my health and wellbeing this year?

  2. How many hours of sleep do I honestly say I get per night? (8 is recommended).

  3. What choices have I given attention to regarding my health (i.e. weight fluctuation, caffeine or alcohol intake, drinking water).

  4. What specific health goals do you want to achieve next year that you didn’t get to?

  5. Have I consulted a professional counselor or psychologist and would it be beneficial to next year?

Section 3—Emotional Health

  1. Which 5 feelings (positive or negative) dominated my outlook on this year?

  2. When was I happiest, what was I doing, who was I with, and where was I?

  3. What was I doing, who was I with, and when did I experience my greatest feeling of sadness this year?

  4. What area of life gives me the greatest sense of internal stress?

  5. How was my emotional well-being this past year? (i.e. rollercoaster emotions, calm and steady, numb).

Section 4—Vocational Health

  1. Which 5 words best describe your current job/vocation/career.

  2. This past year, circle one that is true: ‘I lived to work.’ or ‘I worked to live.’

  3. How are you feeling about your vocational journey?

    • I want to make a wholesale career change next year

    • I want to continue, just as I am

    • I want to do research in another field or prepare to make a vocational change

    • I want to change some aspect of my same job next year

    • I want to pursue schooling/training in my career field

4. I believe I currently work ( ) hours per week.

5. Next year, I want to work ( ) hours per week.

Section 5—Relational Health

  1. How has it been for my friends and family to be on the receiving end of me this year?

  2. Make a list of people who have been life-giving to spend time with this year.

  3. Give a letter grade to my overall sense of community and sharing life with a few other people.

    a. Excellent

    b. Very good

    c. Average

    d. Lacking in friendships

  4. Of the friends I have spent significant time with, has the impact on my character been overall positive, or negative, and why? Are there friendships I need to reevaluate or go deeper with?

  5. Is my lifestyle and work schedule conducive to having the kind and number of relationships you want and need?

    Section 6—Spiritual health (Last one!!)

    1. Describe my prayer life this past year.

    2. What 5 words describe my spiritual health overall (i.e. distant from God, apathetic, hopeful, consistent).

    3. How do I feel how I have worshipped God this year? (i.e. financial investments, volunteer time, community investment).

    4. What was my experience of church this year?

    5. What feels lacking in my relationship with God and what do I think is the source?

    6. What 5 words best describe how I think about God?

    7. What are the biggest points of challenge to my relationship with God?

    8. What are the top spiritual takeaways or breakthroughs I experienced this year?