Simplify Your Life By Asking Better Questions

“If the truth was complicated, everyone would understand it.” Walt Whitman

Brian PennieSep 13 · 5 min read

Photo by Saketh Garuda on Unsplash

Tim Ferriss is a highly successful author, podcaster, entrepreneur and investor. He has written five #1 New York Times bestselling books, and the success of his podcast, which recently exceeded to over 300 million downloads, has seen him named “the Oprah of audio” due to its influence.

In 2017, however, as he turned 40, several of his close friends died in quick succession. It was a harsh reminder that time is a non-renewable resource, and life’s big questions started bubbling to the surface.

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

“How much of life have I missed through underplanning or overplanning?”

“How can I be kinder to myself?”

Overwhelmed by the gravity of his personal interrogation, he asked himself one more question…

“What would this look like if it were easy?”

By journaling on this question, one idea jumped out from the page…

“What if I had a tribe of mentors to help me answer these questions?”

What followed was his most recent book Tribe of Mentors, where Tim reached out to his dream list of interviewees and asked them the very questions he was struggling with himself.

The result of this book is a deconstruction of the tools, routines and tactics from 130 of the world’s top performers. This book is a masterpiece on the secrets of success and happiness. If life is getting you down right now, the chances are you will find a solution in there.

Information Overload

When I sat down to write this article over a month ago, I wanted to tell readers about a tool I came across from that very book. It’s a journaling technique I use when life gets busy.

I wanted the introduction to shine, so I began writing about fancy concepts such as cognitive biases, memory capacity, decision-making, information overload, and even neuroscience.

The words were spewing out of me…

I was on a roll…

It was going to be brilliant.

I excitedly read back over it when I finished. To say it was not good is an understatement. It was crap. When I read back over it, I couldn’t figure out what was wrong. It was a complicated mess, and it was giving me a headache.

Then it hit me…

I was struggling to implement the very technique I was writing about. I was overloaded with information and trying to solve the problem in my head.

But solving complex problems doesn’t work like that. If you want to get answers, you need a technique. And if you want to get to the heart of something, you need to get specific.

Reflective Writing

“Our life is frittered away by detail. Simplify, simplify.” — Henry David Thoreau

A powerful tool for getting to the core of a problem is reflective writing. You simply put a heading at the top of the page and write anything that comes to mind. It is very important that you give yourself time, a minimum of 10–15 mins. Then just let it flow.

Don’t worry if it doesn’t make sense at first. The idea is to create links that might connect to something you’re missing.

Now here’s the critical piece…

If you’re trying to push a project forward, and you write ‘project goals’ at the top of the page, that’s far too vague.

Use something specific: “What can I subtract from the current project that will help me to accomplish things quicker?”

Subtractions work great and specific questions provide cues to get to the heart of an issue.

I once used this method to make an important career choice. I wasn’t sure whether I should focus on my new self-development business, or continue with my studies.

So I asked myself two questions:

“What is it about research that makes me come alive?”

“Why do I want to pursue my business so quickly?”

Notice the specificity of the words in bold. This is what guided my answers.

I won’t go into the details, but I found that both options were interconnected. It made sense to do both, so I did. More importantly, however, I made an informed decision, and my mind was clear.

Thinking Clearly

I also use this method to clarify my thinking and track my life progress.

Here are five questions I ask myself on a regular basis:

“What excites you, what are you passionate about?”

“What new things are you learning right now?”

“What have you done in the last two weeks that is potentially a waste of time?”

“What is your number one goal? Where do you want to go in life?”

“Have you failed at anything recently, are you pushing hard enough?”

I had a remarkable insight when I first used this method, which is why I hold it so dear. Three years ago, I asked myself the first question: “What excites you, what are you passionate about?”

Source: Entry from my journaling diary

I scribbled down anything that excited me… meditation, language, mental health, helping people, skiing, making connections, public speaking, research.

But there was something missing, something big.

I sat with it for a while, scribbled some more, sat with it for a while, and scribbled some more. Then it came to me. I was shocked.

For the previous three years, I couldn’t shut up about a book I wanted to write. But the busyness of life had clouded my mind. I had not thought about it for months. I’m not saying that it was gone forever, but if I had forgotten something that important, what else might I be missing?

What’s more, when I wrote the words ‘my book’ on the page, it was connected to everything else I was passionate about. Writing is now my greatest passion and the focus of my future career.

Would this be the case if I had never used this tool? I’ll never know for sure.

All You Need To Know

Modern life is frantic. There are so many moving parts. If you want to get to the heart of something, there is nothing better than sitting down with a pen and paper.

But if you want to go deep, it’s all about the questions. Vague questions give you vague answers, so you need to get specific. This is the power of reflective writing. You’ll also be able to think, talk, and express yourself better.

Henry Ford was right: “Whether you think you can or you think you can’t, you’re right.”

So maybe it’s time to get specific and find out what that is.

Liked this article? Check out for similar stories, and get the FREE program I developed to make remarkable changes in my recovery from 15 years of chronic heroin addiction.


Brian Pennie

Change is possible. I write to show that. Recovered addict | Speaker | Writer | PhD candidate.

Why Listening is the Most Radical Act

An article from the Gratefulness website


When we think we already know what there is to hear, we are simply moving a little too fast to really listen—That’s where meditation comes in.

Pain and suffering may often seem to be calling us to jump in and fix things, but perhaps they are asking us first to be still enough to hear what can really help…

Photo by Korney Violin/Unsplash

Pain and suffering may often seem to be calling us to jump in and fix things, but perhaps they are asking us first to be still enough to hear what can really help, what can truly get to the cause of this suffering, what will not only eliminate it now but prevent it from returning. So, before we act, we need to listen. When we do become quiet enough and “listen up,” the way opens, and we see the possibilities for action.

We give very little attention to learning to listen, learning to really hear another person or situation. Yet think back to the moments with other people when our hearts were engaged and we felt fed by being together. In those moments, weren’t we hearing one another? In times like those, when we have listened to and heard one another, we have felt life arising from a shared perspective.

Why We Miss New Opportunities

Each situation, each moment of life, is new. We and this other person or group of people have never been here before. Oh, we’ve been in moments like it, but the present moment is new even if we have performed the same action with the same person hundreds of times before. Of course, it’s easy to think, “Well, it’s just like the last time, so I’ll do what I did last time,” and then not have to listen to the new moment. But if we do that, our lives become boring replications of what we have always done before, and we miss the possibilities of surprise, of new and more creative solutions, of mystery.

For our often humdrum lives to retain the taste of living truth, we have to listen freshly—again and again.

For our often humdrum lives to retain the taste of living truth, we have to listen freshly—again and again. A human interaction includes both the uniqueness of each being and the unity of the two, which transcends the separateness. For our minds to take such a subtle process and trivialize it to “just this again” or “nothing but that” is to reduce us to automatons, to objects for one another. And for action to be compassionate, we need to eliminate the idea of object, we need to be here together doing exactly what needs to be done in the simplest way we can. We need to listen.

How Mindful Listening Leads to Real Change

When we begin to act by listening, the rest follows naturally. It’s not so easy, of course—it requires us to give up preconceived ideas, judgments, and desires in order to allow space to hear what is being said. True listening requires a deep respect and a genuine curiosity about situations as well as a willingness just to be there and share stories. Listening opens the space, allows us to hear what needs to be done in that moment. It also allows us to hear when it is better not to act, which is sometimes a hard message to receive.

There are many people and organizations teaching techniques for clear active listening and appreciating the role of listening in the process of change. One such group is Rural Southern Voice for Peace, which has developed The Listening Project, a process by which members of grass-roots groups go door to door or to familiar gathering places as they are beginning a project. They ask “open-ended questions in a non-judgmental but challenging way that encourages people to share their deepest thoughts” about the area of the group’s concern.

Listening to others clearly opens the way to understanding the helping situation. But listening to others requires quieting some of the voices that already exist within us.

They report that “remarkable things happen as this process unfolds: Activists empathize with former ‘opponents,’ replacing negative stereotypes with understanding and concern; barriers are overcome as both sides experience common ground and see each other as human beings with deeply held hopes and fears. People being surveyed feel affirmed, sensing that what the listeners really want is to know their opinions; some start to change their opinions as they explore, often for the first time, their deeper feelings about social problems.”

Listening to others clearly opens the way to understanding the helping situation. But listening to others requires quieting some of the voices that already exist within us. When this happens, there is space not only for the voices of others but for our own truest voice. And, as Alice Walker has said, “The inner voice can be very scary sometimes. You listen, and then you go ‘Do what?’ I don’t wanna do that! But you still have to pay attention to it.”

Three Ways to Practice Mindful Listening

1. Begin by listening to yourself.

We need to take time to quiet down and listen to ourselves with attention—not only in the midst of action but when we are alone, walking in the woods, making tea, praying in church, fishing in a stream, or sitting in meditation.

2. Try a breathing practice.

A simple breath meditation can be helpful, because it returns us to a basic connection with the world. As we breathe in and out, and bring our awareness gently to our breath, we are experiencing the world coming into us and ourselves going back out into the world. We are reminded, in a simple physical way, that we are not separate from the world but continually interacting with it in the very makeup of our being.

3. Give your undivided attention to others.

We need to listen fully. It’s the basis of all compassionate action. Such full listening helps us hear who is calling and what we can do in response. When we listen for the truth of a moment, we know better what to do and what not to do, when to act and when not to act. We hear that we are all here together, and we are all we’ve got.

Reprinted by kind permission of Mirabai Bush. This article was adapted from Compassion in Action: Setting Out on the Path of Service by Ram Dass and Mirabai Bush. All rights reserved.

We are delighted that Mirabai Bush will be participating in our upcoming symposium: Radical Aliveness and Belonging: Exploring the Intersections of Spirituality and Social Change. Please join us for this special event on September 27, 2019 in Amherst, MA.