11 Questions to Ask When Making a Big Decision

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We have a lot of dialogue on the surface.

“Hi, how are you?”

“How’s it going?

“What’s new?”

Do you really care or is this just our society’s norm of salutation? These are probably just rhetorical questions but what if we stopped to answer honestly and thoroughly. While it may be too much of a commitment in a casual encounter, sometimes deeper conversation is welcomed or warranted. When someone close to you seems to be struggling with an issue or needs to make a big decision, asking thoughtful questions can help them arrive at the clarity they are seeking.

The Perils of Giving Advice

Oftentimes we turn to our friends and loved ones for support and advice because we value their opinion. To the one being called upon this can be a lot of pressure. It’s important to recognize that everyone everyone is biased with their own history, outlook, and philosophy and this isn’t necessarily a bad thing.

Peace comes from within. Do not seek it without.
— Buddha

But offering advice derived from our own point of view can be a hazardous course. Without proper care and deliberate objectivity, one’s point of view may make an issue even more confusing. Instead, we want to help someone get back to their basics so they can recognize their truest desires.

So how do we help others (or ourselves) get to the resolution that will be genuine and true? You offer them space to step back and reflect on what they really desire. You don’t counsel them, you guide them.

You do this by asking profound questions. Questions that probably no one else has ever asked them or they have not asked of themselves. By taking this approach we keep the decision maker and what he or she really wants at the center of the conversation.

The sculpture is already complete within the marble block before I start my work. It is already there, I just have to chisel away the superfluous material.
— Michaelangelo

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The Importance of Asking Insightful Questions

These are questions that cut through all the BS and get to the heart of the matter. It takes away the ambiguity. The fluff and pretenses are blown away. You put up a mirror to have them reflect on their core — their thinking, their beliefs, their gut instincts, and their emotional center.

This exercise helps sort out the unconscious tendencies, bad habits, and excuses that may be merely a distraction but viewed as an insurmountable and permanent condition or circumstance. At the end, when the core values are identified, the truth emerges. And it is from this knowing, action can be confidently taken.

What kind of questions do you pose? Thought provoking open-ended ones. The ones that hang in the air and need time to seriously contemplate. As you ask these kinds of questions give your friend (or yourself) patience and time to sit with them. Maybe let them sleep on it. Maybe the answers will spontaneously surface in the shower. But by posing the questions, it will sink into the recesses of their mind where the subconscious will work on it. And in time the gut and the heart and the mind will bring forth the true answer(s).

This can be just the tip of the iceberg but questions like these will initiate profound and meaningful thinking.

  1. What does this mean to you?

  2. Where do you go from here?

  3. How does this make you feel?

  4. What one thing would make you take action?

  5. What are your limits on this?

  6. If you had to decide right this moment, what would you do?

  7. Why is this or that important to you?

  8. What does your gut tell you?

  9. What’s your greatest fear about this issue?

  10. What are the positives that can come from making this decision?

  11. What is this action or inaction costing you?

When someone contemplates questions like these and gives them the time to process, clarity arrives. Like when spring arrives, you know it. The sun shines brighter, trees look greener, and the flowers seem to bloom with vibrant colors all at once.

Paralyzed By Indecision

I went through this exact process when I decided to make a big, scary life change.

For four years I worked in a job that was soul-crushing. It was the wrong fit from the very beginning but I was stuck for two reasons. It was 2008 (the depths of the recession) and the money I was earning wasn’t a luxury I could afford to walk away from. I never let myself consider quitting for the first two years because I felt like I had no other choice.

Hiking with new friends in thailand

Hiking with new friends in thailand

The first time I even contemplated it again was when I went on a trip to Asia. I squeezed in my two-week (too weak) vacation to make believe I really had some true time off. On the trip, I met some great people who all happened to be from the UK. Even though they didn’t know one another prior to the trip, they all had one thing in common. Each of them had either previously decided or planned during the trip to not immediately resume work or school when the trip was over.

Each of them had decided to continue traveling before other commitments began (like starting a new job). And one person, in particular, decided to radically change his life by relocating from London to Thailand after a recent job loss. Each situation was different but the common theme was freedom. They seemed to embrace it without any fear and anxiety attached. I thought to myself, “I want my freedom. If they can do this, so can I.”

From the time I convinced myself to quit (on the flight home) and the date I resigned was almost two years. Two long agonizing years! Over that time I felt torn about my priorities. I vacillated. I rationalized my staying easily a hundred different times. I became paralyzed by the fear of making such a drastic decision. I would set arbitrary deadlines of when x happens, then I’ll be ready. But the goal posts always kept moving.

In my opinion, what I was I unintentionally doing was buying into society’s expectations of what a productive career person does. She stays put in a high paying job because walking away would be irresponsible and foolish. I knew there were people who would kill for a job like the one I had and the income that went with it. I just convinced myself that being absolutely miserable was the price I had to pay.

I let all of these thoughts cloud my thinking and perpetuate my inaction.

Deciding to Decide and Taking Action

I finally found my resolution when I started asking myself some of these difficult questions. While it was challenging to get to the heart of the answers, the process was like clearing away the overgrown weeds. It forced me to call things for what they were.

It was the last question (above) that forced my hand. And for others, it’s usually the one that finally moves them off the fence. It is the question of cost. The financial cost, the emotional cost, the opportunity cost. If you go deeper, the question is ultimately about pain tolerance.

When I honestly examined the pain factor, I realized the cost I could no longer tolerate was potential regret and loss of opportunity. I knew that by maintaining the status quo I was cutting myself off from infinite possibilities for my life and my future.

That is what scared me and pained me more than anything else. Once I came to terms with this, I simply decided. I was able to clearly recognize that the time had come and I was able to take decisive action. I quit my job.

View of Rio De Janeiro Brazil from Tijuca national forest

View of Rio De Janeiro Brazil from Tijuca national forest

It was the best decision I ever made. Once I quit my job I left for an 8-month travel sabbatical to South America. It was a time to decompress, shake off the shackles of corporate thinking, and get back to myself. While the new life wasn’t always easy it brought me deep satisfaction because I was brave enough to choose something different and then finally act on it.

Asking questions like the ones above take bravery. But bravery is like a muscle that needs exercise and conditioning. The more you use it the easier it is to execute in the future. This conditioning has served me well. Now when I am faced with a difficult decision I come back to these questions as soon as possible. I don’t waste time and I stay true to myself always.

Take Action!

If you are wrestling with a big decision take some time to be alone and ponder some of these questions. Journal about them and just sit with them for a while. Wait for some clarity to surface. Sometimes revelations come when we are least suspecting it. When answers emerge, see if you are ready to make a plan of action.

Conversely, these questions can be posed to a friend or loved one who is weighing a big decision.

What process do you go through when making a big decision? Please share with others in the comments.