Tony Leighton is a Canadian writer happily retired and attempting to help others feel the same.

The Particulars of Misery

One of the people I appreciate online is Shane Parrish, the hardworking proprietor of Farnam Street, a blog “devoted to helping you develop an understanding of how the world really works, make better decisions, and live a better life.” Occasionally, Shane throws out a thought on Twitter and crowdsources further thoughts on the same subject from anyone who wants to wade in. Recently, the title of his tweet was, “Guaranteed prescriptions for misery.” I’ve assembled many of them here. The first seven are from Shane. All those below his are from others adding to the list.

What struck me, as it usually does, is how this relates to retirement. It relates because we have the time (and hopefully the desire) to eliminate self-generated miseries. Shane’s big Twitter-sourced list is like an enormous checklist. Check first to make sure you aren’t experiencing or exhibiting any of these miseries. And if you are, check them off one by one as you remove them, like encumbrances, for this final fabulous run at life. (Then check in periodically, because encumbrances have a way of sneaking back into place.)

Substance abuse

Being unreliable



Seeking vengeance

Inability to learn from the mistakes of others

Inability to handle failure

Marry the wrong person

Engage in an occupation you don’t like

Surround yourself with people you don’t like

Earn a reputation you’re ashamed of

Have a bad relationship with your family

Alienate the people you care about

Not being grateful

Lack of humility

Philosophical void (no belief system)

Inability to admit error

Lack of intellectual curiosity

Misunderstanding of what brings you happiness

Believing everything is happening “to” you

Feeling anxiety over everything you eat

Being fearful of what you have to say

Unable to be present with others in the moment

Comparison to others


Poor diet and lack of exercise

Goals in lieu of identity

Inability to take feedback

Not learning how to manage money

Living beyond your means

Inability to delay gratification

Lots of sugar and junk food

As little sleep as possible

No contact with other people

Staring at a screen all day

Avoiding the outdoors

Unrealistic expectations

Perpetual victim mindset

Always blaming others

Greed and selfishness

Inability to see reality

Search for magical solutions to complex problems

Attempting to maintain a lie

Dependence on certainty


Taking your spouse for granted

Being driven by short-term motivators (money, fame)


Being a know-it-all




Failure to develop mature coping styles

Lack of intellectual curiosity and critical thinking skills

Inconsiderate attitudes

Chronic lying

Living for the approval of others

Focusing on things outside your control

Not solving toxic shame

Forgetting time is very limited and precious





Not being able to let go

Believing the locus of control is outside your reach

Not being in the present

Making decisions based on what others will think of you

Inability to apologize and seek help when in need

Chronic pain

Engagement with media and social platforms


Letting grief consume you

Gambling compulsion

Taking yourself too seriously

Seeking excitement constantly

Inability to enjoy small things in life

Lack of discipline

Not leaving enough room in life to decompress




Withholding forgiveness

Compromising personal values

Inability to follow through

Fear (False Evidence Appearing Real)


To what end?