In 1997, I moved from El Paso to Austin, Texas with my husband and our 13-month-old daughter. Moving to a new city where you don’t know a soul is always hard, but I felt especially lonely staying at home with only a baby for companionship while my husband worked. Craving connection, we started church-shopping, visiting a different church every Sunday. People seemed friendly and welcoming, but the depth of our connections only went to a “handshake-and-smile” level. Until we visited one particular church.

By chance, we sat behind a couple that looked to be around our age. At the obligatory “meet-n-greet” time that seemed to be the norm at all central Texas churches, this couple turned around and introduced themselves. We chatted for a few moments, and as the worship music gently cued us to wrap it up, Shelley asked the question that began a decades-long friendship: “Would you like to join us for lunch after church?”

Kevin and Shelley turned out to be great conversationalists. Over chips and salsa at Chuy’s, they asked us a ton of questions about our move, our new home, our baby girl, and what life had been like on the Mexican border. Whenever our answers intrigued them, they would follow up with: “tell me more about that.” Their probing questions didn’t seem at all nosy or come across as an interrogation. They took a genuine interest in getting to know us.

Kevin and Shelley taught me that asking great questions is the key to deep understanding. And there’s no better way to more fully understand yourself than by asking yourself powerful questions.

Questions for Personal Reflection

We always carry a running conversation in our heads, but often it’s just background chatter. It takes focused attention to ask, with purpose, the questions that drive self-awareness. So when I set aside time for a Personal Retreat Day, I reserve a good chunk of that time to ask myself reflection questions and journal the answers. Reflection questions force you to look back and learn from the past. Some of the questions I like to ask myself are:

• What are some “wins” that happened this month that I can celebrate?
• What was a “mistake” I made this month, and how can I avoid making it next time?
• What’s making me feel anxious or fearful right now? (Follow up: What can I control about that situation? What’s outside of my control?)
• What have I learned this month?
• Who did I have an important or interesting conversation with, and what was it about?
• What’s something that recently made me laugh out loud?
• Do I feel my life is in balance? (If not, what’s taken up too much of my time and what’s suffered as a result?)
• Who has helped me this month, and how can I express gratitude for them?
• What’s one big thing that happened this month that I want to remember? (be sure to write it down!)

These are just a sample – you can probably think of hundreds of other reflection questions. Don’t think you have to answer all of them! Choose a few questions that speak to you, or come up with your own list. The main idea is to look back over the time since your last Personal Retreat Day and review the events, interactions, and epiphanies that have occurred. Interview yourself like a reporter searching for a good story.

Forward-Thinking Questions for Looking Ahead

While reflection questions motivate you to examine the past, forward-thinking questions can help you shape your future. Again, there are countless possibilities, but here are a few that I like  to use:

• What’s one thing I’m really looking forward to next month?
• What am I dreading the most? (Follow up: is there a way to make it more pleasant or even fun?)
• Which of my relationships do I need to invest more energy into?
• Is there something new or fun I want to try out? (such as a recipe, a TV show, or a relaxation technique)
• What’s one small thing I can do to improve my health (physical or mental)?
• When I look at next month’s calendar, do I feel stressed out? If so, what can I delegate or give up entirely?

Again, this is just a starting point. I suggest keeping a running list of questions like these and adding to it over time. At each PRD, pick a few from the list to ask yourself. Journal the answers so you can look back to see if the month panned out the way you expected!

The Bonus Question

• What day will I choose to take my next Personal Retreat Day?

Before you walk away from this month’s Personal Retreat Day, take out the calendar and pencil in the next one! By doing so you’ll reinforce the habit and keep yourself accountable. Then go do something fun and relaxing to reward yourself for the mental energy you just expended answering all those questions. You deserve it!

PRD Activity Cheat Sheet:

1. Take out a fresh sheet of paper or open a new word document

2. Write down at least 5 questions you could ask yourself at your next Personal Retreat Day (have a mix of reflection and forward-thinking questions)

3. Add to the list whenever you come across a new power question

4. Be sure to bring your list and a journal to your next PRD!

One more question before you go:

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