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October 07, 20233 min read

In the darkest days of COVID, April and May 2020, I was faced with a stark reality: my business was dying (or was it dead?!) 

The online business I founded with my wife back in 2006 was on life support. (A travel business with a dozen employees - but nobody could travel due to the pandemic!)

And the lifestyle and financial freedom I had enjoyed from it for so long were crumbling. The various "hobby businesses" I was involved in at the time weren't bringing in the income I now needed. I had to get serious. What was I to do? How was I going to reinvent myself? 

Faced with these realities and yet a newfound sense of opportunity, I took a personal day retreat here in Florida and asked myself a series of the following questions. I took a good hard look at my journey thus far - from college until that day. Assessing my skillsets, interests, how I'd changed, who I was becoming, what I wanted for me and my family and so much more. 

What follows are many of those questions and some of the favorite coaching questions I use with my clients. May they help you as you clarify where you're going and how you desire to create a lifestyle of freedom and adventure. 


Direct questions to ask yourself as you make a major life pivot, moving toward an ideal version of what you’d like your life to look like. 


Chris’ Top 3 existential questions for any point of life to remember:


Who am I?  Why am I here?  Where am I going? 


Clarifying questions to dig deep: 


What am I interested in? What am I good at? 


What did I study? What work abilities and talents have I cultivated over the years? 


What topics could I talk about easily for an hour? 


What am I known for? 


Who do I want to help? 


How do I want to help them? 


By what methods and means do I want to help them? 


Financially, what do I want and need to make?  


What are my next steps? Sequentially? 


When will I offer my product/service? 


What is important to me right now? 


What would you like your life to look like three years from today?


What short term pain are you willing to sustain to reach this goal? 


Looking at your life from a high-level, what would you tell yourself to remember?


How could this (challenge/difficult change) work FOR you? 


What does this (challenge/opportunity) make possible? 


If your situation is the same in 24 months as it is today, will that be acceptable? Why or why not? 


What will you stop doing, or start doing differently to make time for the new opportunity? 


What failures are you using to grow yourself? 


Let’s say you have a real magic wand, where would you like (your business, relationship, health, or life) to be in the next 6 month to a year? 


What do you think could be holding you back, slowing you down or stopping you from having all that you desire in life? 


What has hindered your progress in this area in the past? 


What are you willing to do differently to move forward? 


What do you really want? 


What are you afraid to say you want? 


What are you hesitant to say out loud that you really want? 


Where is that (limiting) belief coming from? 


If you knew you couldn’t fail, what would you do? 


What’s an action you can take today (tomorrow, this week, this month) to move forward on your goal? 


What are your goals for the next 90 days, 1 year, 5 years and ultimately 10 years?

I'm happy to talk more about these with you sometime on a complimentary call. Book HERE.

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Chris Niemeyer

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