If at First You Don’t Succeed…

An overhead shot of a writing desk, containing a pen, a pad of paper and a cup of coffee.How many of us grew up with the old saying, “If at first you don’t succeed, try, try again”?

And how many of us have had moments in life thinking that this societal expectation is… well… a load of nonsense?

I think it would be safe to say that for a kid endowed with only a modest helping of patience, the advice holds some degree of merit.

For an only child who was all too happy to throw in the towel and give up a game after one unsuccessful try, it might also be value-added.

For a short, academically-oriented kid for whom athletics was never in his wheelhouse, the advice was probably reasonable… to a point.

In all three cases, that was me!

But as an adult when we are more in touch with our likes, our aptitudes, our affinities and our passions is “try, try again” without any footnotes, asterisks or any sense of boundaries really good advice?

Shouldn’t there be a cut-off point, when there really isn’t a point to continue?

I realize that to grow as individuals, stepping outside of our comfort zone is necessary to develop wisdom, experience, confidence and currency. Then when a similarly challenging situation is on the horizon, we should be better equipped to handle it.

But when I look back over my life and my career, I see too many times when I was doing my best to adhere to society’s advice to “try, try again” and wasting precious time, energy and headspace on situations that never really came to fruition.

For example, who hasn’t encountered an individual or two who were a challenge to deal with? I have.

Despite my best efforts to “try, try again” and to be kind, courteous, respectful and professional with them, the courtesy and respect were never really reciprocated.

Was it because I was a borderline extrovert? Was it because I was too cheerful? Was it because I was (and still am) a morning person?

How many sleepless nights did I spend trying to figure out what I was doing wrong? Was “try, try again” really the best advice?

I now accept that you can’t please all of the people all of the time. So why did I beat myself up, trying and trying again? In hindsight, I should have just kept my distance. If our paths were to cross, I should have kept conversations short, professional and respectful.

Later in life, it took five limited-duration assignments in management for me to decide that it just wasn’t for me. The pace of decision-making was just too fast for me, not allowing enough time to weigh the pros and cons to reach a decision that would sit well with my gut. I also found myself spending more time dealing with administrative requests and less time coaching the team. To me, the red tape took the fun out of the job.

By that point, I was so tired of trying to find my happy place in the world of management, a hard boundary was drawn in which I turned down all future offers. Maybe I tried too hard to make it work, if that’s possible.

Outside of the office, let’s just say it didn’t take “try, try again” too many times to realize that I will never enjoy blood sausage, I have no natural talent for golf and that winter is my least favourite season… and that’s OK.

Let’s face it, no matter how many times we try to insert a square peg in a round hole, it’s just not going to happen unless you break the board.

But on the other hand, there were times when the advice to “try, try again” did work out pretty harmoniously.

It was through that lens that I discovered and nurtured a love of running.

With the right recipe and a little practice, I have mastered gluten-free pie crust that I think would hold up in a contest.

Also, more recently, my first steps into screenwriting have been productive and very enjoyable. Whenever I have a finished product in my back pocket (to prove to myself that I can do it), I would not be deterred if/when one of my story pitches might get turned down. For screenwriting, I will “try, try again.” I enjoy it and to me, it is worth the effort!

But with the old saying to “try, try again”, at no point is success guaranteed. For that reason, I had to fill in the blanks with my own asterisks and footnotes.

Ironically, I now tend to gravitate to a sports metaphor: the three strikes rule. If I’ve tried my best, with an open mind and an open heart, and it doesn’t work out after three attempts to “try, try again”, it is time to draw the line and move on.

With a world of possibilities at our fingertips, why not empower ourselves with boundaries and permission to move on and to try something else?

I don’t think there is anything wrong with giving things a good try and if things don’t work out, having the ability to confidently assert, “No thanks, I tried it. It’s not for me.”

Life is just too short!

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Sincere thanks for reading!
Have a great day,


Filed under 50+, mental health, stories

2 responses to “If at First You Don’t Succeed…

  1. I like the way you think. There is definitely something to be said for knowing what your limits are and being able to gracefully bow out if a situation, or a person, or a hobby is something that doesn’t improve no matter how often you try, try again.

    • Hello Lydia,
      Thank you very much for the positive feedback.
      It certainly wasn’t without struggle that I reached that conclusion, but in a few situations, it became apparent that the concept of “trying” without a cutoff point was becoming a drain on my energy and my optimism. Three strikes seemed to strike the right balance!
      Cheers and have a great day

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