I wrote this short article for another project I’m working on…and thought I’d post it here as well.  I’ve collected a huge list of questions that I like to ask myself on a pretty regular basis, and watch as my answers evolve over time.  I started doing this a while back as a mindfulness/mediation technique while reading some books on, and watching a few documentaries on the great Indian sage –  Ramana Maharshi.  He spent most of life, and most of this teaching based on asking one simple question: “Who Am I”.

 Of course, it feels like there is an obvious answer to that question, but when you probe a little bit deeper, you realize that he or she who thinks they have the answer, becomes subject to the same question.  Pretty soon you realize, it’s turtles all the way down.  (and this is supposed to lead to the great enlightenment experience and A-ha moment that arises when you recognize, that there is really no one there to ask the question, nor to offer up an answer – just the energy of aliveness itself)

Anyway – I can’t offer you enlightenment in a conventional sense.  But I can offer you some ideas on how this teqnique can be equally as effective for getting crystal clear and equally as enlightened about the work that makes you feel alive, and offers an enthusiastic insight into what the world really wants of you.  (even if you don’t believe the world is watching 🙂

I will be posting about 50 of these questions in a PDF on a group project I’m working on, and will post them here as a download as well.  The abbreviated version is below.

There is a guy who lives in my building, who I see from time to time in the parking lot.

 Every time I see him he asks me the same question, undoubtedly trying to make harmless small talk:  “Heading to work?”

Each time I see him, I say some variation of the same thing:

“No, headed to the store.  I actually work from home”

Or –

“No, headed to the beach.  I work out of my condo”

Or –

“On my way out to meet a friend for lunch.  I actually work from here.”

And every time he seems to nod knowingly, offers up a quick wave, and off we go in different directions.

It occurred to me a while ago, that while he may be a very nice guy, I really don’t like seeing him.  Not because we’ve ever had any really acrimonious interaction, or anything much beyond what I described above.

It’s the question that he asks, each time, that reveal something really important about how much he cares about me, my life, and my answer at all.

Not much.

I had this moment where I realized that the quality of the questions we ask offer up an amazing insight into the level of passion and sense of purpose we have about ourselves, and others.  The truth?  The quality of the questions you ask about your blog, your brand, your business, your content, your community will have a direct affect on your bank account to boot.

I want to give you a series of questions I started to ask myself a bunch of years ago that have had an incredible effect on my business, my content, my community, and more importantly, how much I actually enjoy my work.

Important note:  NONE of these are really “my” ideas, and all are, in some form or another, extrapolated from the ideas, insights and experiences with others.  This is the beauty of asking empowering questions.  They endure from niche to niche, market to market, person to person and even over generations, and remain phenomenally effective for getting hyper clear about your mission, your manifesto and what matters most.

Tribe Questions:

  1. Who is my ideal audience?
  2. Who are my people?
  3. What do they love?
  4. What do they need?
  5. How can I serve them?
  6. What do they fail to do or understand?
  7. What service can I offer to make them better?

Brand/Business Identity Questions

(I call these clarity questions)

  1. Who am I?
  2. What do I do?
  3. Who do I do it for?
  4. What do they need?
  5. How do their lives change when I do what I do BEST for them?

If I absolutely couldn’t fail, what would my blog and business look like in 30 days?

  1. What would I have?
  2. What would I do?
  3. What would I be?
  4. If my life were a book, and I was the author……what would I write?
  5. If my life were a movie, and I was the HERO, what would I do NEXT?  (this is very powerful for me)
  6. If my life were a movie, and I was the HERO and millions of people were watching my story right NOW, how would I act next?  How good would I be?  How kind could I be?  Who would I serve?  How can I help?

Lastly, questions that simplify whatever you are working on are often the very best ones to ask.

  • What is the absolute MINIMUM I need to make this product/project/program helpful to others?
  • What is ONE key thing I can teach that will save people time/money or pain.  (based on my own experience or expertise)
  • What would this look like if it were FUN?
  • What would this look life if it were EASY?
  • What would this look like it were SUPER simple, and taught just ONE thing that made people better

IF there is one great lesson I’ve learned in life as a creative, it’s this:

Your relationship to life is really about the questions you ask.  You prioritize yourself when you are diligent enough to keep probing your psyche for answers that empower and inspire you.

But ask with passion and purpose and with a genuine curiosity to connect with truth.  (rather than to make small talk with yourself like a neighbor who doesn’t really care 🙂

When we don’t ask questions, we are pulled and poked and prodded in a million different directions, and even when we arrive at out destination, how we got there remains a mystery.



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I am an author, artist and entrepreneur. My 2 passions are writing about, and teaching Marketing and Meditation. I like to think I'm a lot like Eckhart Tolle, if only he was taller, and a much better tennis player. (it turns out in person, he's super short, has a terrible backhand and wears this weird scottish hat thingy that makes it really difficult to concentrate while serving) Plus he refuses to keep score and says " it's always NOW" when you ask who is up. Enough about me. We barely know each other. Stop staring. You're making me nervous.