Bonnie Ware spent her life taking care of the elderly and spent time with many people in the final moments of her life.  Her work would result in one of the most read blog posts on the internet, “Five Regrets of The Dying.” The most common regret that people grappled with towards the end of their life is that they did not live a life “true to themselves,” pushing their dreams aside to do what others expected of them.

Our fears are not a mystery, yet when we explain them to people, they are often in the form of excuses rather than the underlying fear.  Instead of saying “I’m scared that I’m not good enough” we say “I can’t do that because I can’t be unemployed.”  The fascinating thing is that while our bold admission of vulnerability may be more honest, it is the latter response that is more persuasive.  Dr. Robert Cialdini has shown that offering a reason, even if it is absurd – “I can’t leave my job because I am allergic to tootsie rolls” – can be convincing even if it does not make sense.

The Four Most Common Fears

In my work with clients over the past several years who are “stuck” in jobs they hate or even worse, deep into careers that they regret, I have discovered that there are four common fears that hold people back.  Some of these are solvable, while others are not.  The four most common fears are:

  1. “I might not be able to achieve my goals”
  2. “I might go broke”
  3. “My health might fail”
  4. “I might be judged harshly or not accepted/respected by people”

The common factor in all of these fears is a large element of uncertainty or lack of control.  Some, such as an unexpected health crisis, may be completely out of our control while others such as not being able to achieve goals, may be mitigated by identifying small actions that may alleviate our fears.

The Fear Setting Exercise: Taking Fears From Your Imagination To Reality

Tim Ferriss has grappled with insecurity and fear of failure all of this life.  He was able to finally tame his fears after being inspired by Stoicism and specifically, a quote from the ancient Stoic philosopher Seneca, who said, “We suffer more often in imagination than reality.”

He took the spirit of this mindset and created a process really grapple with his fears and bring them to life.  His belief, like mine, is that we don’t adequately define our fears.  Instead, we grasp on to general concerns and use them as reasons why we can’t take action to move towards the things we want in life.  While I am less concerned with one’s action or inaction, I love helping people look at their fears and say wow, that’s not as scary as I thought.

Fear Statements: Being Specific About What You Are Afraid Of

I work with many people who are taking the leap to self-employment and help them work through the exercise mentioned by Ferriss as well a “fear sentence” exercise I developed.  People have a hard time moving from a general fear (e.g. “being broke”) to the specific definition of that fear (e.g. “making less than $36,000 in a year).  To address this, I ask questions that help people be very specific about what failure entails:

  • I am okay not having any paid work for ____________ (time period).
  • If I do not make _________________ in a month/year (circle) I am a failure
  • I am willing to commit to self-employment for _________ (time period)
  • The worst case scenario for me is when __________________.
  • It is irresponsible for me to _________________________.
  • I will know I have failed when ________________________.

An interesting thing happens when people are forced to be specific about their fears.  First, the fears lose power over them.  The act of writing something down forces them to stare at the fear with an external lens, almost as if it is someone else’s fear.  Second, it shifts the mind toward actions you can take to start to lower the odds of “failure” as you have defined it.

Following this, I have people work through Ferriss’ “Fear Setting” exercise.  My slight tweak on the exercise takes people through the following six questions:

  1. Identify the “shift” or change you are making
  2. List the worst possible outcomes
  3. Identify actions you could take to mitigate those actions
  4. List some steps or actions you might take to get back to where you are today
  5. What could be some benefits of an attempt or partial success? (What might you learn? What skills might you develop?)
  6. What is the cost of inaction (in 3 months, 12 months and 3 years)?

The Fear Setting Toolkit Is Included In The Reinvent Toolkit

Reinvent Toolkit (Includes Fear Setting) – $50

How To Re-Frame Fears

After working through the exercise, I dive into the fears with people.  There are different approaches for grappling with the four kinds of fears:

#1 “I might not be able to achieve my goals” – People often do not think small enough and are skipping many steps on their journey.  Once people take a leap to entrepreneurship or self-employment, they find that the journey is much longer (while more rewarding) than expected.  Whether acknowledge of not, there is often a shift from a goal-oriented way of thinking to a systems approach.  Instead of trying to build a million dollar business, you are focusing on building one-high quality relationship each week, delighting every customer or working on your craft every day.  Finally, as many know, not achieving your goals is part of the journey.  The key is to begin that journey and build up your resilience to those inevitable small failures.

#2 “I might go broke” – We’ll get to this in a second…

#3 “My health might fail” – While unexpected health crises are often looming, this is one of the easiest fears for people to address.  Often when someone mentions their health, they identify an exercise or nutrition regimen that can help help keep this fear at bay.  Major health crises don’t schedule themselves conveniently in your life and are a reality of life.  For me, a major health crisis helped me realize that I had nothing to lose because I realized that my worst case scenario was not working surrounded by my loving family.

#4 “I might be judged harshly or not accepted/respected by people” – The idea of self-sufficiency is strong in the West and it makes people blind to the love around them.  Our fears of lack of belonging often stem from this fear that we will be rejected once we have failed or are not living up to expectations.  This is rarely based in reality.  Just ask someone what they would do if their friend or family needed help.  To address this fear, I have people visualize themselves broke and without shelter. Then I have them make a list of the friends and family that would feed them, give them shelter and support them. Many people are surprised at how many people make the list.

Dancing With The Money Fear

When you start dancing with fear, money inevitably demands a spot on the dance floor, if not the entire ballroom.  Almost everyone I have worked with has a complicated and emotional relationship with money.

Some equate money with their own self-worth and to be broke (or sometimes merely making less than they currently make) is to be worthless. Others feel like they will never have enough and constantly yearn to need more.  Some even struggle with money in the reverse, not feeling that their work or creations are good enough to be paid for.  Regardless of the specific fear, understanding your emotional relationship with money is something everyone should spend the time to reflect on.

A lot of these fears are driven from our current state of modern employment which gives you a steady paycheck for the partial or total relinquishment of your unique skills or passions.  After years of this, many people assume that a steady paycheck is just a fact of life.

When people start exploring alternative paths, they quickly give up when they are not able to imagine an alternative path that also has a steady paycheck.   Most entrepreneurs and freelancers will scream from the rooftops “It’s worth it trust me!” but that rarely changes any minds.  Shawn Achor explored this fear and chalked it up to a failure of imagination in his book, Happiness Advantage:

“Just knowing this quirk of human psychology—that our fear of consequences is always worse than the consequences themselves—can help us move toward a more optimistic interpretation of the downs we will inevitably face”

I’ve written a bunch more on grappling with financial insecurity and lifestyle creep as well as re-framing how I think about retirement here.

You Will Eventually Run Out Of Time

Professor Shai Davidai at The New School for Social Research and Professor Thomas Gilovich at Cornell University published convincing research on regret suggesting that we should be more willing to follow our dreams.  They found that people’s biggest regrets have to do with failing to live up to their “ideal selves” rather than their “ought selves” which is what others expect of you, rather than your own hopes and ambitions.  The reason for this is that people are “quicker to take steps to cope with failures to live up to their duties and responsibilities” than taking action towards their dreams.

When you take the long view on life or talk with the elderly, like Bonnie Ware did, fears seem to shrink in importance.  While some fear may be in our imagination as Ferriss says, some of our fears will be realized.  When it comes to health, Ware shares her insight, “From the moment that you lose your health, it is too late.”



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