Originally, I had hoped to host a phenomenally epic 40th birthday party and invite tons of friends and family to celebrate. If you’re reading this blog post, you would have likely been invited. As an extrovert, I get energized by being with people. For my birthday last year we hosted a chicken-wing tasting party and I invited our entire church to come. When I turned 30 we had a 30-hour birthday party and friends and family dropped by whenever they wanted over the course of two days.
Unfortunately, given the current circumstances, my dream of a big party couldn’t come true. However, it allowed me to plan a party creatively that would hopefully still be somewhat epic (and if not epic, then at least memorable).
What I love most about a big party is being able to have many meaningful conversations with people I care about. So, for my 40th birthday I wanted to to have meaningful conversations with 40 people on Zoom over the weekend. Each conversation would be 10 minutes long and would be spaced throughout the weekend.
With 10 minutes, I proposed to my friends that we make the most of our time by asking one question each. They would get to ask me one question, and I would get to ask them one question. We’d skip the small talk and get right to the good stuff.
That was the idea. But being an Enneagram 6, I started thinking about worst case scenarios. What if people thought this was a stupid idea? What if no one signed up to chat with me and it was a failure? With the encouragement of Olive and a few friends, I went ahead with it and I’m glad that I did.
My friends and family asked me some amazing questions. Some questions were deep and reflective and others were fun. Their questions were gifts for me and helped me to reflect on this milestone birthday. I was also able to ask them a question that allowed me to know them in a deeper way.
Although I didn’t have great answers for all the questions, I know I will be reflecting on these questions over the coming weeks. Here are a few questions I did have answers for that I wanted to share with you.
What is one of the best hard-earned piece of wisdom you’ve learned so far?
This was asked by my journalist friend. I think the “hard-earned” part of the question makes this one especially interesting. My piece of hard-earned wisdom is “Let your life speak.” This is the title of a book by Parker Palmer that changed my life. What he says in the book is that instead of telling your life what you intend to do with it, let your life speak. He writes, “Vocation does not come from willfulness. It comes from listening.”
In my 20’s, I made career decisions that led me to six seasons of depression over a decade, because I chose to do work that did not align with who I was. I had not spent much time listening for my vocation. It wasn’t until I turned 30 that I started understanding my calling, and shifted my career towards work that was life-giving and aligned with who I am more closely. This is probably my most hard-earned piece of wisdom.
What superpower do you wish you could have?
Asking good questions at the right times. In recent years I’ve discovered how a thoughtful question can be a great gift. In the past, my go-to method of helping others was giving advice (often unsolicited, and usually unhelpful). Through coaching and clearness committee training, I’ve started understanding how question asking is usually more helpful than sharing advice.
Also, I’d like to have Jedi force powers.
How does your life’s game plan change after turning 40?
There’s a shift towards taking on more of a mentoring and coaching role. As my kids grow up, I think my role as a father shifts from being a teacher and instructor to becoming a mentor and coach. If I want our business to outlast my own career, I know I have to shift towards coaching and mentoring others to do the work, more than doing the work on my own.
Turning 40 feels like I’m entering the second half of my life. I’m starting to think more about my legacy and what I want to be remembered for.
Do you see yourself as fundamentally the same, or different?
Fundamentally the same. When I was in my teens and 20’s, I had less self-confidence and clarity about who I was, so in many circumstances I acted a lot differently than how I act now. But underneath it all, I haven’t changed. For example, most people (including myself) thought that I was an introvert as a younger person. But I was really an extrovert (like I am now), acting like an introvert because of insecurity.
If you could ask God one question, what would it be?
“How much do you love me?” I know God loves me, but I think if I could have a better understanding of just how much He loves me, it would make a big difference in my life. Understanding more of His love for me would help me to love myself better, and love others better.
—
I’m grateful that despite the pandemic, I was able to have a meaningful and fun milestone birthday. My kids woke up at 5:30am this morning to excitedly create decorations, hanging them from the ceiling all around the house. Olive cooked me waffles, bacon, and sausages for lunch, and ribs and chicken wings for dinner (all my favourites). She and the kids also teamed up to bake me fresh cinnamon buns (also my favourite). I feel loved and celebrated. And I’m looking forward to more conversations with friends and family tomorrow as well :)
—
Edit (Jan 17, 5pm):
Several people have asked me what other questions I’ve been asked, so now that my 40 conversations are done, I’ll share some of these questions with you:
- What question would you want to put toward 20-year old Tim that would have made the most positive impact in his life?
- What is the most life-giving practice you’ve been doing to help you rest, and to help you be productive?
- What are you proudest of in your life?
- To get the most out of your next decade of life, would you focus on your mindset, your motivation, or your methods?
- How do you nurture your children to discover their calling in life?
- If you were 16 years old and could see into your life at 40 years old, what would surprise your 16-year old self the most?
- How do you make time to plan and to dream as a couple?
- If you could take your family anywhere in the world for a month, where would you go?
- In the darkest moments in your life, how did you hold on to hope?
- What is the most significant turning point in your past 40 years?
- As you look back at your 40 years, what would you do differently?
- What are you reflecting about as you turn 40?
- If you could choose to play one sport at the highest level for a game or a specific situation, what would it be?
- How has your declining health impacted how you live out your calling?
- What has been the one thing that has changed the most about yourself, and the one thing that hasn’t changed?
- How has growing up as a first-born child impacted how you parent?
- How do you want to be remembered?