I have recently read two books on the topic of “Questions” from my mentors, John Maxwell (Good Leaders Ask Great Questions) and speaker coach and mentor, Roddy Galbraith (Go Out and Make a Mess). These books could not have come at a more opportune moment for me as everyday I am stretching my life into unchartered territory both personally and professionally.

Both books forced me to take a deeper look at how questions unlock the doors to the unknown. They raise awareness and bring answers. Questions are utilized to connect with people, collaborate with team members, build ideas, and develop personal leadership. Questions give us a different perspective.  

By asking questions and listening carefully to the answers, we can begin to understand valuable perspectives other than our own. This is critical because we can often make faulty assumptions about other people:

  1.       We believe people are good at the same things that we are good at – they are not
  2.       We believe people are energized by the same things that energize us – they are not
  3.       We believe people see the big picture in the same way we do – they do not

Of the one hundred or so reflective questions these two books ask the reader, these four questions stood out to me most:

  • What would a dream life look like?
  • What are the five most things you desire out of life?
  • If you knew you could do something that you would not fail at, what would it be?
  • What are the fears and attachments holding you back?

I do not know about you, but typically, when books ask me reflection or application questions, despite all my good intentions, I never go back to answer them. I know that if I want to change and grow I need to be a better follower. So I gave it a go and began journaling on these questions:

What would a dream life look like?

Crickets…I was stuck! I was letting personal doubts and a senseless need to know ALL the details get in the way of my reflection. Needless to say, I was a little disappointed in myself that I struggled to put in words what a dream life might look like to me.

Instead of having a pity party I moved on to the next question.

What are the five most things you desire out of life?

  1. To live like a tourist (I want to travel and experience life from all corners of the world with friends and family).
  2. For my children not to have the burden of student loans (I have over $100,000 in loans. It is nobody’s fault but my own. I have a responsibility to ensure I do not pass this on).
  3. To have peace of mind when it comes to daily living and family time.
  4. To have my wife not feel guilty buying new slippers when her old ones get a hole in them.
  5. To do something for others, that outlives me, which will provide people with opportunities to achieve their goals and dreams.

If you knew you could do something that you would not fail at, what would it be?

A full triathlon. I have completed four marathons and one ultra-marathon (50km); however, swimming is definitely my kryptonite. I bought a book this year, Total Immersion, to learn how to swim and completed a few laps this summer. Baby steps…but that is my answer.

What are the fears and attachments holding you back?

Drowning with this last question!

While looking at the five things I desire out of life, four of my answers (or perhaps all of them) have a financial requirement. I learned that cash is not everything, but it is right up there with oxygen if you want to achieve your goals.

One area I do struggle with is the idea of being wealthy. Weird statement coming from someone who gambled almost every day for a decade. What was my goal besides being a constant loser?

Perhaps I feel guilty having gambled away a small fortune (half-a-million) over ten years on a teacher’s salary. I feel like I do not deserve wealth because of the great heartache I caused those closest to me. Maybe it was the way I saw the desire for wealth tear my mother and stepfather apart when I was a teenager? Or could it be the fact that until I was 35 years old, I blamed my money problems on everything and everyone except myself?

Could it be the guilt I feel asking people for money as independent business owner for the fear of looking greedy?

I remember when I was a state consultant, we analyzed those companies who profited financially from school support.  Now I am one of those “for-profit” companies we judged.  

I realize that I have a bias, guilt or under-serving feeling towards the idea of being wealthy.

A mentor helped me through this attachment and asked me, “Tom, how much of your own money and time have you invested in yourself so you can meet the needs of your clients?”

This was indeed a question I never thought about before. Just off the top of my head, I knew the financial investment was in the tens of thousands of dollars in tuition, professional development and certifications. In terms of self-development hours, it is well over a thousand hours a year in trainings, reading books and listening to leadership podcasts. This helped me better understand my value, and the value my company has in the charter school world. Without my constant investment in me, our clients will not receive a very high return on their investment.  

How to overcome fears and attachments

Pain is not doing the things that are hard. Pain is dropping the attachments in order to do what is necessary. When you are comfortable, the very act of dreaming stops you from actually achieving anything. The first step in achieving anything, I believe, is to doing the thing so you can build the energy, momentum and experience to really do the thing! Adapt, adjust and overcome.

I love this video – The opening quote is, “Some people like to build mountains. I like to build planes…as they fly.”

For me, in order to achieve my five desires, and as a result “my dream life,” I need to recognize my own value and put my fears aside. This is how I plan to do it:

  1. Exercise my mind like a professional athlete exercises his/her body in order to increase my ability to attain financial stability while working in a field I love  
  2. Not lose time caring what other people who are not in my inner circle think
  3. Stop spending time on items that do not take me closer to any of my goals

Courage is a muscle. It grows by overcoming resistance. This is why you need to own the choices you make and not blame others for where those choices take you. If I get stuck, I will revert back to my action steps which I listed by goal. Some of these items are tangible and some require more thought. This is where collaboration with your partner is crucial.

My challenge to you is to take the next 24 hours to list out the five things that you desire most out of life. Sit with your partner share these items. Meet at least monthly to discuss action steps to continually progress towards achieving those goals. Enjoy the process and celebrate each win!

My team and I are hosting a mastermind study on Good Leaders Ask Great Questions starting September 18. Join us over the next month and begin unlocking the doors that contain the answers you need!


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