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Never Good Enough: The Futility of Striving to Meet Others’ Expectations

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Note from Ashley: I asked Randy to write a guest post for me, after coming across his book and story in a Facebook group. His post on his blog, The Question I Never Asked Myself, hit me in all the emotions and I may or may not have teared up. I asked him to expand on that feeling in a guest post, and he delivered. I hope this blesses you as much as it did me.

How does a person arrive at a place where they feel doomed to fall short, no matter the goal?

“He ain’t nothin’.”

I’d just started attending a new high school, and one of the basketball players had seen me in a casual setting trying to shoot some hoops. I’d overheard him sharing his evaluation of my skills with some fellow players. Frankly, he was right, at least when it came to basketball. No way could I meet the high expectations required to join their club.

Failing to live up to others’ expectations was hardly limited to the basketball court. From academics to business acumen to God, over the years a haunting feeling that I’d never measure up became a subtle but ever-present reality.

Truth be told, I was—and am—actually pretty good at some things. No, playing sports wasn’t one of those things, but I excel in many other areas.

How does a person arrive at a place where they feel doomed to fall short, no matter the goal?

Here are just a few reasons:

  • Spiritual and other authority figures setting impossible standards
  • Lack of parental or caregiver affirmation
  • “Discounting” (Successes are attributed to good luck or other reasons.)
  • Setting oneself up for failure (Poor choices in relationships and other areas.)
  • Perfectionism
  • The WPT (What People Think) factor.
  • Secondary gains. For example, others may feel sorry for you or enjoy the jokes you make about your failures. The emotional rewards of secondary gains can be powerful and lead to further unhealthy psychodynamics.

In my case, a constant sense of failing to measure up resulted in “imposter syndrome.” This term hails from the sense that every success can only be attributed to the fact that you somehow managed to pull the wool over someone’s eyes. No way could I actually earn a master’s degree (which I did) without some of my professors looking the other way, right? Or how about being a successful magazine editor? Surely that was only because the publisher’s standards were so low!

You catch the drift.

The good news is that I spend a great deal less time these days worrying about measuring up. Why? One reason is because, by now, my successes in life have multiplied to the point where it’s hard to chalk them all up to good fortune alone. In the spiritual area, understanding the role of grace has helped to set me free.

But something else has been key in helping me to stop looking for affirmation in all the wrong places. I finally realized that, in one way or another, we’re all inadequate (perhaps even incompetent) in some areas.

In other words, we’re all human! That may sound trite, but in the matter of failing to measure up to spoken or unspoken expectations, we all need to get a life.

Here’s the deal. I could probably write circles around Katy Perry or Tom Brady, but they’d laugh me off the stage or football field if I tried to emulate their abilities. Even if our core skills don’t reach celebrity status, there’s no denying that we all have strengths and weaknesses. Some of us just take our shortcomings too seriously!

Celebrating our successes is a much better use of our time than whining about how we once again fell short. We all have successes, minor or otherwise.


Don’t waste your time and emotions trying to measure up to someone else’s standard(s) for your life. You own that life, and you must choose the benchmarks for it.

Striving to meet others’ expectations is sure to add anxiety to your life. Pressing toward a reasonable goal that you’ve set for yourself will bring a sense of purpose and achievement, even if you don’t quite reach a specific goal.

The important thing is that you’ve pursued that goal on your own terms and not someone else’s. It feels kind of good to be you, doesn’t it?


Randy Fishell lives in Smithsburg, Maryland. He is the author of the soon-to-be-released book, An Anxious Kind of Mind. Learn more and sign up for his blog and email list at

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  1. 4 Ways To Overcome Perfectionism on June 30, 2017 at 11:52 pm

    […] Previous post: Never Good Enough: The Futility of Striving to Meet Others’ Expectations […]

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Sitting on top of Pike's Peak in Colorado, a little over 2 years sober.

Hi! I'm Ashley, and my sobriety date is May 6, 2015. I write to share my experience, strength, and hope in recovery. On any given day, you can find me developing websites, writing, or chauffeuring kids around.  Read my story...

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