Asking the Right Questions: Question 1

Note: I actually wrote this post over a month ago, but then I started second guessing it and hesitating on posting it. But that mentality is counter to the purpose of this blog, which is to get me more comfortable with sharing my ideas and writing more regularly, even though they will always be a work-in-progress. I can edit a piece forever, and it will keep getting better, but there comes a time when you need to press publish and let go. So here it iswith no further editing or hesitation. More to come soon!

Lately, I’ve been feeling an odd mix of peace and purpose with feeling completely lost. 

It’s not what I’d expect with the way my life has been going so far this year. There have been a number of high points. 

I’ve been highly focused on a meaningful morning routine, making time for journaling, reading, yoga, and meditation most days before sitting down to write fiction and for this blog. These habits make my days so much more fulfilling and productive. 

I’ve been pushing myself to regularly stretch my comfort zone, and it’s been going amazingly (more on that in its own upcoming post).

I currently have more chess students than I ever could’ve imagined. To the point that I’ve had to do some mental jujitsu to fit all of them into my schedule. Around this time last year, I set out for exactly this. Throughout the year, as I tried to increase my number of students, I had a number of ups and downs in my attempts. It’s hard to believe that somehow I’ve made it here.

I greatly enjoy teaching. My students are wonderful, every single one of them. And my income is more steady than it’s ever been. 

Yet, with any endeavor I take on that’s not connected to my writing goals, I still wonder: Am I going the wrong direction?

When will I actually finish my novel? Did I really let a month go by without posting my blog? 

It’s a new year, and I feel opportunities all around me. I feel a version of myself I’ve been searching for for a long time starting to break through. Yet, I have these moments where it still feels like something is missing. What is it? 

In my search to figure out what’s still missing or blocking me, I’ve turned to an old favorite book of mine, Tribe of Mentors by Tim Ferriss. In the intro Tim explains reaching a point in his own life where he was in search of answers:

“To explain why I wrote this book, I really need to start with when.

Two thousand seventeen was an unusual year for me. The first six months were a slow simmer, and then, within a matter of weeks, I turned 40, my first book (The 4-Hour Workweek) had its tenth anniversary, several people in my circle of friends died, and I stepped onstage to explain how I narrowly avoided committing suicide in college.

Truth be told, I never thought I’d make it to 40. My first book was rejected 27 times by publishers. The things that worked out weren’t supposed to work, so I realized on my birthday: I had no plan for after 40.

As often happens at forks in the path—college graduation, quarter-life crisis, midlife crisis, kids leaving home, retirement—questions started to bubble to the surface.

Were my goals my own, or simply what I thought I should want?

How much of life had I missed from underplanning or overplanning?

How could I be kinder to myself?

How could I better say no to the noise to better say yes to the adventures I craved?

How could I best reassess my life, my priorities, my view of the world, my place in the world, and my trajectory through the world?

So many things! All the things!”

To search for his answers, he created a list of 11 meaningful questions he thought could help his life and sent them out to 100+ people whom he sincerely wanted to hear answers from, which led to the content of the book. 

According to Tim, the key is in the questions:

“The older I get, the more time I spend—as a percentage of each day—on crafting better questions. In my experience, going from 1x to 10x, from 10x to 100x, and from 100x to (when Lady Luck really smiles) 1000x returns in various areas has been a product of better questions. John Dewey’s dictum that “a problem well put is half-solved” applies.

Life punishes the vague wish and rewards the specific ask. After all, conscious thinking is largely asking and answering questions in your own head. If you want confusion and heartache, ask vague questions. If you want uncommon clarity and results, ask uncommonly clear questions.”

What I love about Tim Ferriss is how he works to see past his limitations by recognizing which ideas are vague and unsupported. From there, he focuses instead on the search for specific, tested answers on what actually can be done—when you apply a thoughtful, open mind to the task. 

If you’ve read my core values article, Core Values: What Matters Most to You?, you know that I believe that the first step to anything is a better understanding of yourself. So, in my own search for answers (along with reading the incredible answers provided in his book), I’m going to start by answering his 11 questions myself, one to a few at a time as posts in this blog. 

Some of the questions reach deep, like “if you could get one message out to millions of people, what would it be?”, while others are subtle yet meaningful, such as “what book have you given most as a gift?”

My hope is that this exercise will help me understand myself and my current predicament better while jumpstarting me posting more regularly on this blog again.

What questions do I have more answers for than I realize? What questions are areas I need more searching to answer better? What questions have I discovered answers to that I forget in the moment in practice?

Let’s find out. 

Tribe of Mentors: Question 1

What is the book (or books) you’ve given most as a gift, and why?

Or what are one to three books that have greatly influenced your life?

I love this question, and there is one book that is overwhelmingly the answer for me: Tiny Beautiful Things by Cheryl Strayed. It is the best expression of empathy that I’ve discovered at this point in my life. When I first read it four years ago, it helped me open up to my more empathetic self immensely. 

It’s the book that I reread more than any other periodically: to help myself reframe my experiences and perspectives on others. It’s the book that has taught me the most about human connection. It reminds me that: We are all more beautifully flawed as human beings, more connected, and more craving of connection in everything we do than we realize. 

I think every human being can benefit from this book. 

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