A midlife crisis — or even a quarter-life one — can change a lot of things.
When you hit these age milestones, you can end up questioning even your core values and beliefs.
I’ve gone through a few midlife crises myself — from changing careers to wondering if I should stay single forever — I think I’m more than qualified to write this article 🙂
Here’s a list of questions to have a conversation with someone who’s going through one. You can also use these questions for your own reflection… like I did!
When and how to use these questions
No hard rules per se, but here are a few suggestions:
- Ask these questions only if you built some rapport with the other person — and they have indicated interest to talk about their midlife challenges. As these questions can go fairly deep, even friends might feel uncomfortable about sharing their honest thoughts.
- Ask one question at a time. Gauge their response before going deeper. If they seem disinterested in the topic, switch to something else instead.
- Balance between asking and talking. Make sure that you share your answer to the same question, or comment on their answer, so that the conversation doesn’t become an interrogation 🙂 I’ve been guilty of that.
- Most importantly, modify the questions and brainstorm new ones based on what sounds/feels most natural to you.
Why is that important? Different people have different ways of saying things. The more you can tailor the conversation starter to your tone of voice, personality etc., the easier (read: less awkward) you will find using it.To make this more usable for you, I’ve tried introducing variations of the same question 🙂
With that said, let’s jump in!
Work through your emotions
- How do you feel right now?
- When do you feel <a specific emotion>? What triggers it?
Why do you think you might be feeling <a specific emotion>? - What might <a specific emotion> be telling you about yourself?
- Could it be that everything is fine and complete as is? (Credit: Tim Ferriss)
- How can you move towards your goals/lifestyle despite <a specific emotion>?
- How can I best support you? (What support do you need the most?)
Reflect and learn from the past
- What is your greatest career accomplishment?
- What is your greatest personal accomplishment?
- What’s the most valuable/surprising lesson you learned in your career?
- What’s the most valuable/surprising lesson you learned in your life?
- What’s the most valuable/surprising lesson you learned about yourself?
- What has brought you the most joy/made you the happiest?
- What/who are you most grateful for?
- What do you regret not doing?
- What fear is holding you back?
- What hurt haven’t you processed?
- What are you avoiding?
Revisit your core beliefs & values
- What do you believe in the most? Why?
- What do you no longer believe in?
- What are your core values? (Have they changed, if so why?)
- What would it be like to fully live your beliefs and values? (How would you live your life differently?)
- Who do you want to become?
Look into the future
- If there’s one thing you want to accomplish, what would it be?
- What’s the one area of your life that you want to focus on, if any?
- What would you regret not doing?
(Here’s Jeff Bezos’s version: “At the end of my life, will I regret not having done this?”) - What’s the next chapter of your story? (What’s the one word that represents it?)
- Imagine that you’re the character of your own movie. Where will you be? What will you do? Who will you be with?
- What’s your dream lifestyle?
(If you want to go deeper, here’s a list of lifestyle conversation starters. I also recommend checking out Cal Newport’s article.) - Where do you want to stay in the next ten years?
- What do you really want to do for the next ten years?
- Who do you want to be with for the next ten years? (For a lifetime, even?)
Question #7 – 9 are inspired by Naval Ravikant:
“Spend more time making the big decisions. There are basically three really big decisions you make in your early life: where you live, who you’re with, and what you do.
We spend very little time deciding which relationship to get into. We spend so much time in a job, but we spend so little time deciding which job to get into. Choosing what city to live in can almost completely determine the trajectory of your life, but we spend so little time trying to figure out what city to live in.”
Reinvent your career
- What excites you? (What makes you come alive?)
- What drains you?
- What do you want to stop doing?
- What do you want to try? (What are you curious about?)
- What do you want to build?
- What new skills/mindsets do you need to learn?
- What do you need to unlearn?
- What relationships do you need to build for a new career?
- What if it’s OK to settle in your career?
- Are you playing someone else’s game or your own game?
Reevaluate your relationships
- Who do you want to spend more time with? (Who do you want to build deeper relationships with?
- Who do you love, and do they love you back? (Here’s why Warren Buffett says that’s so important.)
- Who do you want to reconnect with? (Who have you neglected — that you regret?)
- Who do you want to cut out of your life? (for example toxic people)
- What relationships do you need to let go of? (relationships that aren’t serving you)
- What boundaries do you need to set or lift? (could be in a specific relationship, could be in general)
- Any new people you want to get to know?
Do a final gut check with these two questions…
1. Is this a Hell Yes or No?
This question came from Derek Sivers, the founder of CD Baby.
“When you say no to most things, you leave room in your life to really throw yourself completely into that rare thing that makes you say “HELL YEAH!”
2. If it was the last day of your life, would you want to do what you’re about to do?
Death is a fairly morbid topic. But it shakes you up and gets you to see your life differently.
As Steve Jobs shared in his 2005 speech:
“Remembering that I’ll be dead soon is the most important tool I’ve ever encountered to help me make the big choices in life.
Because almost everything — all external expectations, all pride, all fear of embarrassment or failure — these things just fall away in the face of death, leaving only what is truly important.”