6 Questions to Ask When Making Hard Decisions

Credit: Flocutus

Photo: Flocutus

Do you have a hard decision to make?

Life is filled with circumstances where we need or are forced to make hard decisions.  The reason these decisions are difficult is that there is not always a clear way forward and we are filled with anxiety about making the wrong choice.

In my life and in the lives of many people I’ve coached, I’ve seen people struggle with decisions around:

  • Starting or ending a relationship
  • Leaving a job or staying
  • Committing time to an activity or saying no
  • Starting a plan to get healthy or doing nothing
  • Making a significant purchase or holding on to your money
  • Moving a family for a work opportunity
  • Planning to retire or keep working
  • Starting a business or working for someone else

Whatever the hard decision you need to make, I find the following questions helpful in making the best decisions we can.

1. Is the option in alignment with my values?

One of the biggest stresses in life is when you act in ways that violate your deepest values. If we make choices that conflict with our values, then this is an indication that an option may not work for us.  Not all of our values have equal importance in life. I think it’s helpful to rank order your values so your decision falls within your highest priorities.

2. Is the decision about something where there is clearly a right or wrong?

Many decisions we struggle with have nothing to do with right or wrong, yet we have anxiety about making the wrong choice.  If you are buying a car and staying within your budget, does is ultimately matter if you buy a Toyota or a Ford?  If you are pursing a new job and have two offers, could both options be a good fit?  If there is no discernible right or wrong, what seems best to you? In these types of scenarios, you can’t make a bad decision so determine what may be the better option for now.

3. Do I have enough information to make the decision?

Sometimes we get paralyzed when making a decision because we don’t have all the details about the benefits or drawbacks of our options.  This requires that we take time to ask questions, do some research, or consult with experts.  Once you have the information you need, the path to making a better decision will be clearer.

4. Will I regret choosing or not choosing an option later in life?

Author Mark Twain has this great quote: “Twenty years from now you will be more disappointed by the things you didn’t do than by the ones you did do. So throw off the bowlines. Sail away from the safe harbour. Catch the trade winds in sails. Explore. Dream. Discover.

When making a decision about how I am going to spend my time or resources this is a question I often ask. I find that if I believe I will regret a decision later in life, then I have the insight of what I need to do now. Sometimes playing it safe is the best option, but sometimes taking a calculated risk, trying something new, or starting a new venture will lead to less regrets.

5. Have I talked through my options with people I trust?

Don’t go it alone when making tough decisions.  We all need an outside perspective to gain clarity on next steps.  Engage with good friends, family members, and colleagues.  Read books written by authors you admire.  Talk with a leader in your business or industry.  Hire a coach. I believe it’s a good idea to have a good mix between people we consult with, some who have personal interest in our outcome and some who don’t.  This mix will give you different feedback.

6. Have I given this decision enough time or too much time?

There are decisions we can’t rush. The outcomes have significant meaning in our life and relationships. The decisions could affect others and so we need to take time gather information, ask ourselves the above questions, and consult with people we trust.

The are also times when we are delaying a decision we know we need to make.  This heightens anxiety and leads to frustration.  If we are taking too much time it may be a signal that we don’t feel capable to make a good decision or that either option we choose has difficult components.  In these situations I encourage setting a deadline for a choice to made, gathering any missing information, and talking with people you can trust and who will hold you accountable.


A  challenge in making hard decisions is that sometimes there is information or experiences you can never know unless you try. When people are going through divorces, leaving a job, or moving to new cities there is anxiety of the unknown.

Will I be OK?

Will I succeed?

Will I like it there?

Sometimes we will make a decision that we later regret and here is the good news.  I don’t think any experience in life is wasted as long as we learn and grow as individuals. We all make decisions given the information and context of our life at a given time, so let’s have so compassion on ourselves.

One of the best decisions you can make is to be your best self. Start there and use the above questions as a guide on your way.



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Drive By Wisdom: Ask For What You Need














It’s hard for us to get our needs met if we are not willing or brave enough to ask for what we need. In this episode of Drive By Wisdom, we’ll explore how asking for help can improve your life.  Click on the video below:

Drive By Wisdom: Letting Go of the Outcome

In this Episode of Drive By Wisdom we’ll look at how letting go of the outcome can help you achieve your goals with less stress and more engagement.

Play the short video below.

Do Our Failures Define Us or Inform Us?

Credit: Harman Abiwardani

Credit: Harman Abiwardani

Relationship failures. Business failures. Career failures. 

Been there and done that.

What about failures in parenting? Failed partnerships? Vocation or educational failures? There are too many failures to mention, but we all know we have failed somewhere in our lives.

The question I have for you (and for myself) is do your failures define you?  What I mean by that is do we allow our failures to set our identity?  “I’m a divorcee.”  “I’m a dropout”. “I’m unemployed”.

Setting our self-worth and identify by our failures is a limiting experience. It limits our ability to see our life in the broader context of all that we do well and all that has gone well. It narrows our view on who we are to external events and actions.

When we allow our failures to define us we go to dark places in our minds.  We relive the past over and over and focus on our mistakes.  Dark places lead to dark emotions and there is nothing helpful about depression and anxiety.

The inner critic in our minds blames us for being stupid,making bad choices, or for being naive. It focuses our minds on the mistakes, the blunders, and the omissions.  The inner critic is not our friend, so don’t treat it like one.

Instead of letting failure define us, what about letting it inform us?

Hidden in every failure is a clue to our next success. We need to let go of the failure, let go of the guilt and shame, and let go of the discouragement. We can instead embrace a learning that will make us stronger and wiser.

Here are a few questions we can ask ourselves when we have a failure, whether it be big or small:

  • Why did I fail?
  • What would I do differently if I could do it all over?
  • What was within my control? What was outside my control?
  • What is the key learning I can take from this so I don’t repeat it?
  • Who do I need to help me figure this out?
  • Was it worth it, even though I failed

I’ve used this strategy to help me understand one of my failures.  From 2006 to 2008 I was self-employed. I was an independent consultant and was working hard to build my consulting business. After two years I was breaking even, which is better than losing money, but still not successful. Then the  recession hit in 2008 and I decided to fold my business and find a full-time job.

Here’s what I learned from that failure:

  • I started my business too early in my career.
  • I didn’t have a big enough reputation for what I do
  • My network was too small
  • I was gaining momentum in late 2007 but the recession hit
  • While I liked being self-employed I missed having colleagues

If I were to start my own business in the future I would have a greater chance of success, because I have 10 more years of experience, a bigger reputation for what I do, and my network is huge compared to 2006. (No worries to my employer, I’m happy where I am at.)

Was that failure worth it?  I think so.  The reality is that the company that I  work for was attracted to me because of all the work I did in my own business. While I didn’t make enough money, I still built the skills and experiences that my current employer was looking for. In that sense, it was worth it.

When I was a kid I used to be afraid of failure, so I excluded myself from things that would have been beneficial to me. As I matured I gained more courage to try new things and engage with new people. Some things were successful and some failed, but all of these experiences contribute to who I am today.

I’m a huge believer that nothing in life is wasted.  From all experiences, both good and bad, there is something we can learn.

Learning from our failure is one of the ways we become our best selves.


Slow Down to the Speed of Life. Interview with Psychologist and Author Joe Bailey


Feeling like life is moving too fast and you can’t keep up? Anxious and frustrated?

Then, Slow Down to the Speed of Life.

Slow Down to the Speed of Life is a phenomenal interview with psychologist and author Joe Bailey where we discover how to change our thinking in order to better handle the stress of life. Often we are looking for our circumstances to change in order for our lives to improve. They key to resilience to life adversity and overall mental health, is to change our thought process in order to change how we feel and respond.

Slow Down to the Speed of Life is one of the best books I’ve read and I plan to read it every year to remind myself how to slow down, live in the moment, and enjoy life to the fullest extent possible.

For more information about Joe Bailey, his books, and videos go to:  www.joebaileyandassociates.com

Crazy Things We Do When We’re Not In the Momement



Let’s be honest with each other. Sometimes we say or do stupid things when we are not paying attention.  My family has a good laugh when remembering one of the random things I said during a dinner time prayer.

It was one of those evenings when I was on autopilot.  It was my turn to say the dinner grace and my mind was anywhere but on that prayer. As I said thanks for the food and for family in the same way I usually do, my mind went somewhere else, but my words were on autopilot.  Instead of saying, “Amen” I said, “Thanks and good night”.  The laughter started in a nanosecond.  “Thanks and good night” while not altogether wrong, sounds more like someone ending a talk show than a prayer.

This is yet another reminder of how easy it is to live outside of the present moment. Our minds can pull us toward thoughts of past events and future events and the present moment before us gets lost.

I’ve had conversations with my wife where I was physically there but mentally far away.  When I get the question, “Are you listening?”, I have to admit that I wasn’t.

I’ve had too many mornings where I’m thinking of  the things I need to accomplish at work and I think, “did I brush my teeth?”. My thoughts were so consumed with the future that I wasn’t paying attention to the present task of getting ready for work.  I think that happens to many of us.

I’ve missed off ramps, turns, and  destinations because I’ve been so engrossed in something I was thinking about.   Some might call this ADD. I call it not living in the moment.

Living in the moment allows us to connect with the work we are doing, the people around us, and ourselves. But I’m learning that living in the moment is not something we do, but rather a skill we build.

It takes time and practice to live in the present and to not allow our minds to lead us to past events that we can’t change or the future events that haven’t’ happened yet. I find the more our thoughts are centered on the past or the future we are missing out on life because life only happens in the now.

Mentally living in the past or the future is not innocuous. It causes real stress in our lives and heightens our anxiety. It causes us to miss out on meaningful experiences in our relationships. It leads us to ignore the beauty around us. It slows down our productivity at work. It’s not helpful.

The culture around us doesn’t make this easy. We are bombarded with news, marketing, and advertisements that pulls our attention away from the present. Our lives our busy with work, family, and activity.  There is always something to do and somewhere to go.

In my life I’m working on practicing more presence in my day. Here’s what I try to do:

  • Take deep breaths throughout my day
  • Turn off the news and the news feeds
  • Stop checking my email every 2 minutes
  • Get off of social media when I need to focus at work
  • Go for a run/take a walk
  • Pull my attention to the present when my mind wanders

Like I said before, living in the present is a skill we build and with more practice the easier it gets.

My call to action for you is to adopt one or two strategies each day to pull your attention back to the present moment. Living in the moment is a life practice and small steps each day will make a difference.