3 Lessons from Matt The Storyteller

Read time: 5 minutes

Welcome to The Ascend Archives Friday Edition where I share insights from the brightest minds in business and life and how I'm applying them to my life.

If I make a list of my top 10 favorite things to do, having conversations with interesting people would easily be in the top 3.

Last month I had one of these conversations because of my friend Mike. We were on the phone in January and I was telling him about everything I was excited about: my writing, wanting to create experiences for people, and starting my own business. A guy in Mike’s business mastermind named Matt had come to mind as someone who talked like I did, thought like I did, and did some of the things I was aspiring to do.

Mike connected us and after two months of back and forth, Matt and I hopped on a Zoom call. We had one of the most engaging and insightful conversations I have had in years.

Typically these networking calls all follow the same cadence:

1. Open with awkward small talk of “How’s your week” or “Where the weather”

2. The less experienced person gives their 2-minute elevator speech of who they are and why they set up this call

3. The more experienced person sheds some knowledge

4. The less experienced person then asks questions until time runs out

But this was different.

With a pen and paper in hand, Matt jumps right in, “So great to meet you, Andrew. Mike tells me we share a lot of common interests in storytelling and creating experiences for people. I would love to learn what excites you about these topics and what you’re working on”

For the next 60 minutes, we had an effortless conversation of me telling my story with Matt taking notes and asking questions to better understand who I am and what I’m about. He would then seamlessly insert stories and experiences from his own life that were inspiring, motivating, and insightful. I didn’t get to ask any of the 6 or 7 questions I had planned to ask and yet they all got answered or became irrelevant.

Matt showed me what it looked like to be interested and how to pour into others. It’s been a month since our conversation, but I was recently looking at my notes from the call. Here are 3 lessons from Matt I am starting to apply in my life.

1. Questions Invite Revelations

Matt constantly reminds himself of this quote, “questions invite revelations”.

I’ve been thinking a lot about asking better questions: both to myself and to others. It’s funny because the company I used to work for, Ernst & Young, would have signage in all of the offices around the world with the slogan “The better the question, the better the answer” that I never gave much thought to. That was a mistake because it’s so true.

I’m in the middle of re-reading 10x is Easier than 2x: How World Class Entrepreneurs Achieve More By Doing Less. The main takeaway from this book is that when you aim for 10x results, you are forced to ask yourself different questions than if you are trying to get 2x results. The 10x approach requires thinking differently.

After my conversation with the NYT best selling author, I decided to explore what would it look like to build a life where I only need to write two or three books a year and charge $70,000-$100,000 per book. That question leads to very different answers than if I just asked what is the best way to make $6,000 this month.

The first question comes from a long term mindset aligned with my values of autonomy over my schedule, flexibility to work from wherever, and working on something I enjoy. The second question comes from a short term mindset of covering my expenses no matter what it takes.

By asking these questions, I have decided to focus on writing my own e-book. This book most likely won’t make any money in the short term, but in the long term could help me build a proof of concept to land future ghostwriting clients and will be good practice for my writing skills. Without asking myself the question of how do I 10x my results, I would have never decided to start writing a book.

2. Not everyone wants to hear your story

Not everyone will want to hear your story and that’s OK.

As I continue down this creative journey, I’m not going to please everyone. Some people won’t like my writing style. Some people won’t like the topics I write about. Some people won’t like how long my newsletters are. Some people won’t like the platforms I use. And that’s totally OK.

All I want is to find the small subset of people who do resonate with my style and the things that I’m writing. I’m not writing for other people. I’m writing for me. I’m writing to improve my thinking and frameworks. I’m writing to connect with those people who share similar interests and want to collaborate on ideas. If you try to please everyone, you will end up pleasing nobody.

3. What story are things around me trying to say?

Matt challenged me to look around at things in my everyday life and ask, “How can I look at everything in a different way” and “What story are these things trying to tell me”?

It could be the barista at the coffee shop. The flowers starting to sprout. The abandoned building on East Riverside Drive. The desk I sit at every day.

How did these things get to where they are? Why are they the way they are?

At first, this seemed a bit too spiritual and ra ra for me. But I gave it a shot when I’d go out for walks or when I was in new environments. I found that there were some times these questions sparked my curiosity and other times not so much. Do I really care about where the desk came from that I sit at? Not really. I bought it for $100 off Amazon. But if it was a vintage desk that had been passed down from 5 generations, I’m sure there would be some cool stories about the desk and the men & women that sat there.

In particular, I found that I’m curious about people. Last weekend at my Ironman race, I said Go Blue to a guy wearing a Michigan shirt and started to ask him questions. That led to receiving great advice for the race and a memorable experience.

While I agree with Matt’s advice on asking these deeper questions about the things around me, I realized that it’s ok to not be curious about everything. There are going to be some things that I am curious about that other people are not and vice versa.

Final Thoughts

I learned a lot from the 60 minutes I spoke with Matt. From his demeanor to his outlook on life, to the power of storytelling and asking better questions. I’m sure that conversation was one of many for him that week and he hasn’t thought much about me since.

But I’ve been thinking a lot about what he taught me and applying it to my life. I was about to write “One day in the future after applying what I learned from him, we’re going to cross paths and I’ll tell him how much that conversation meant to me”.

Instead, I’m going to make that day today. After publishing this, I’m going to drop him a quick email just to say thank you. Why wait?

Thank you for reading! As always please reply and let me know what resonated, what didn’t, or what you question. I love chatting about this stuff!

Cheers,

Andrew