I have a friend who I try to spend time with at least once a week.  We usually meet on Friday nights at some watering hole and have a few beers but calling her my drinking buddy is the understatement of the year.  Yes, we often catch ourselves complaining about the challenges of  life as drinking buddies do,  but the reality is our discussions span the gambit of topics including history, philosophy, interpersonal relationships, family dynamics, business, careers, and personal enrichment.   

 My friend is deeply intelligent and experienced in areas of the world that I have little exposure too.   She is unique in that she can both relate to my skewed view of the world as well as maintain a more mainstream outlook.   She’s also one of the very few people i’ve ever met who is accepting of my somewhat *ahem* eclectic personality yet challenges me to improve and develop beyond my current reality.  In one of our more recent conversations she used a phrase she speaks quite often, but this time it stuck with me.   I honestly forget what I was venting about but it most likely was a mistake that I may have made a second time without remembering the lesson from the first time.   Here response was in a tone that was commiserating and condescending at the same time.  She said “Yeah, let’s not do that again!”.  That got me thinking, why do we ‘do that again’?  Why do some people continually make the same mistakes over and over?  What even qualifies for ‘don’t do that again’ status, if such a thing can even be quantified?  

Iterations on a Concept  

In business, it’s a benefit  to try something again.  Think about how many people quit their jobs go into business for themselves and fail.  Yet the stories are legion about people who after failure upon failure eventually hit on the thing that explodes when just the right elements properly come together? The first obvious example of this is the Apple Newton.  Think of the Newton, a self contained portable personal digital computer you kept in your pocket vs. the iPhone.   One was a huge flop that was roundly parodied in popular media for its shortcomings.  After the disaster of the Newton you would think that Steve Jobs would never have ventured into those waters again.  Yet the iPhone came along about ten years later and fundamentally changed the world in so many ways it’s nearly incomprehensible.   

There is the age old adage of the definition of insanity being doing the same thing over and over again and expecting different results.  Jobs and company didn’t do the same thing over and over again.  They did many different things such as dropping handwriting of any kind in the interface, going touch only, and integrating the computer product with a phone. They centralized app distribution through a store and included a new business model hiding the cost of the device.  So at a very high level of ‘let’s not do that again’ they shouldn’t have.  If someone made the statement ‘We tried handheld computers, that market doesn’t scale’ we wouldn’t have things like instagram, selfies, and teen sexting.  OK, maybe someone should have said that because it would have saved the parents of the world uncounted ulcers.  Seriously, If Apple did make the decision to stay away from handheld computing then we wouldn’t have Facetime for grandparents to see the grans, DSLR quality cameras in our pockets and GPS’s that let us know when we are coming up on an accident in real time.  I could easily write several books on the changes brought about by the mind bending concept of a population that now has instant anywhere and anytime access to the world’s knowledge.  

It’s this concept of an iterative approach that justifies trying something again.  We do learn through failure, through lots of little ‘Let’s not do that again’s’.  Enter into a partnership without a contract or clearly defined parameters? I can promise you that you will be saying “Well let’s not do that again!” very quickly.    Over leveraging your business startup through loans?  After a couple of hard quarters and a bankruptcy you’ll be saying “Let’s not do that again!” I personally have experience with the decision to sell the products of others.   I will never do that again no matter how seductive the pitch is, but this doesn’t mean I won’t try to go into business for myself again.  I’ll just never fall for the multi-level du-jour.  All this being said, sometimes people do the exact same thing again and to the same results.  Why is this?  I think Emotions are to blame in part.   


There are some instances where it’s obvious why people repeat what could be argued as less than positive experiences.  The first one that comes to mind is childbirth.  I’m not a female, so I never had, and never will have the opportunity to experience the birth of a child.   That being said, I have witnessed the birth of two of my children.  I have to say, it didn’t look fun.  The process included anxiety, tremendous pain, nausea, some screaming, and spending four days in a room with chairs that had cushions which felt like they were chiseled out of granite.   We also had the distinct privilege of paying thousands of dollars for the experience, and that’s with being covered by health insurance.  Even ignoring anything related to the decades and expense of child rearing, this seemed to me to be clearly to be a case of ‘Let’s not do that again!’.    Why would anyone who has had a child one time wish to give birth again?  Obviously many people do because if each person only had one child, mathematically the human race would be wiped out in just a few short generations.  I’m told that there is a thing known as birth amnesia where all the pain and stress relating to birth disappears once the child is placed in the mother’s arms. After witnessing the birth of my first child and a few short years later hearing my wife tell me she wanted another one, I absolutely believe it.  

I have another example that isn’t so driven by biology. Many, many years ago I made some new friends right after I moved to my new home here in North Carolina.   As a Florida boy I mistakenly assumed that they had been to Disney World, because I was still under the impression that everyone goes to Disney at least once, if not multiple times, every  year.  I learned in one of our earliest conversations that this is not normal for kids who grew up in Maine.   I decided to rectify that situation by calling up another friend down in Florida who worked in the parks and who could get us tickets gratis and I planned their first Disney experience.   The trip was a total disaster.  My Carolina friends, a young married couple, were simply unprepared for the experience.  They didn’t bring enough nearly enough money, they bickered non stop for days and they didn’t seem to appreciate the lengths I was going to to give them a unique life experience.  They wanted to do things in the park that you could do anywhere and they ignored the attractions that were only available at Disney.   I was embarrassed for my friend who on a favor gave me several hundred dollars worth of Disney passes that he could have given to anyone and I was embarrassed for myself.  The arguments continued the entire length of the trip all the way until we got home.  I’m honestly surprised our friendship survived it and I swore to myself that “I won’t do that again!”.  The thing that shocked me the most about the trip actually happened a couple of years later when the wife of the couple was reminiscing about the trip.  She looked at me and earnestly said “That was so great, we should really do another trip to Disney!”.  I was flabbergasted.  Was she on the same trip that I was?  Did she not remember being pissed at me for days and for me being pissed at them?  Did she not remember arguing with her husband to the point of tears multiple times a day?  Did she not remember how miserable we all were?  

Admittedly she was at a bad point in her life when we had that conversation and she may have been reaching for any emotional life vest she could reach, but come on… there were a thousand other things she could have reached for.  Why did she have such rose colored glasses about a clearly miserable trip?  Was this just a different variant of birth amnesia?   Is every single repeat bad decision because of our tendency of forgetting the negative experiences or because of an emotional revisionist history?  Do we just forget the pain and problems brought about by a decision and that’s why we repeat them? The complex emotions in both of these examples would explain why repeating something that was clearly a bad experience seems like such a good idea as time passes.   So emotions are clearly one reason why we don’t say “Let’s not do that again”.  But what if we know the experience is going to be bad but still desire to do it?” What are the causes of that?

No Other Option

It’s a little known fact but the number one vacation destination for people in Florida is North Carolina.  Conversely the number one vacation destination for people from North Carolina is Florida.  Most vacationing carolinians target Central Florida and ground zero for Florida Tourism: Walt Disney World. This is why another of my examples includes a different trip to Disney World.  This time it’s a family trip including the core family of another friend and one of their in-laws.  The reason why the in-law was going is because my friend is of modest means.  She wanted to take her kids to Disney but had no money to do it.  Grandma offered to take everyone so the kids could go to Disney.   We can’t forget in this situation, if grandma is the one who pays she gets to have allot to say!  I’m sure you’ll find it shocking that there was much fighting, replaying caustic family scripts, and over all a generally bad experience.   The key this time around is my friend is both 1) experienced in bad trips with the in-law’s, and 2) smart enough to know better.  I asked her why she would do something so foolish as to go on another trip knowing it would be a disaster?  Her response, not surprisingly, is that this is the only way she could pull it off.    

This would lead to the belief that repeating bad experiences has more to do with family scripts and interpersonal dysfunction, right?  Nope.  Don’t forget that we are pigeon holed in our careers.   What if your straight commissioned sales and you got yourself into the cycle of getting fired every two years because that’s just how things generally happen in your industry?    You know the goals will be completely unrealistic.  You know the pressure is going to be intense.  You know that you are going to get fired sooner or later.  But what are your options?  Even if you are very good with numbers what are the odds that someone is going to hire you as a well paid bookkeeper?  Technically it could happen, but if you have things like mortgages, car payments, and a desire to eat then it makes sense that you will apply to jobs where you can get hired quickly to get that cash flowing again.  It’s not just sales, it’s any job at pretty much any level. What if your a Certified Nurse’s Assistant who has experience in nursing homes and you found out you really don’t like that environment?  It’s filled with low pay, intense regulations, and frustrating clients with their families.  It doesn’t matter if you technically can work in doctor’s offices and hospitals, If you apply to every place you are certified to work,  guess where most of your job offers are going to come from?

No matter if you had a horrible experience in a job or engaging with Family.  Sometimes you have to make a judgement call.  Is the pain worth the outcome?  Yes, the kids will be just fine if they don’t get to go to Disney until they can pay for it  themselves. Yes you can walk away from the mortgage.  This being said,  how many of us want to do those things to get away from a job or a family experience that we know we shouldn’t do again, if just for sanity’s sake?  How many week long scream fests will it take before my friend decides no amount of Mickey Mouse rice krispy treats and Character Breakfasts are worth dealing with the mother-in-law for a week?  These limitations in our choices are a big issue when it comes to making the same bad decisions again and again, but they are not the biggest problem.    

The Biggest Problem

That old phrase of “Fool me once shame on you, fool me twice shame on me” is sound but not perfect.  The biggest problem is not from how quick you can figure it out.  There are so many variables in the decisions we make, and there are so many experiences in the maturation process  that sometimes it takes a few times making the same mistake before we really understand that we shouldn’t do that again, whatever ‘that’ is.

The biggest problem comes from the conflict associated with the arrival of “Let’s not do that again” status for any decision.  For some it takes several times, but even the low self esteem girl who gets herself into abusive relationships time after time eventually stops repeating that mistake. It may seem to take forever but I can honestly say that I’ve not known any silver foxes who keep abusive men in their lives.   

We are all not hermits under a bridge by ourselves and only come out once a year during the solstice celebration.  We are engaged in very complicated ways with all of humanity.  The biggest problem comes from conflict when individuals who are connected hit that point at different times.   These can be deeply personal connections.  Imagine the couples i’ve discussed in this article.  What if my friend eventually tells her husband “Yeah, dummy i’m not doing that again” when the oh so generous mother-in-law decides she needs to pay for the whole family to go spend a week together in a cabin on some mountain so the grans can experience nature?  Her husband may have a hard time saying no to his mommy or may think the experience of having mommy pay for everything is worth the issues because he can deal with the dysfunctional family script better than she can as he’s used to it after a lifetime of playing his role.  Then you get to some serious marital conflict.  The same often happens when the cause of daycare and diapers falls into the ‘Let’s not do that again’ status for only one part of a couple.  This happens on the job too.  The boss will tell you to work a territory that lead to nothing the last three times it was tried because the competition owns it.    Maybe there is some product line the higher up’s want to invest in, but you know the company’s internal politics and mis-aligned core competencies doom the new line’s chances for success.  It’s really hard to go to anyone other than a confidant at work and say “we sell to a transient population with no money management skills so maybe it’s not a good idea to give them a 30 year mortgage”.   You would get walked out the door until the eventual economic meltdown happens and then there won’t be a front door left anyway.    

There are also macro versions of these situations where whole populations say “Let’s not do that again”.  This is most clearly seen in politics. Free trade with no trickle down resulted in a majority of the electorate thinking “Let’s not do that again” and acting on it at the voting booth.  That pendulum will swing back the other direction in a cycle or two.  For the most obvious concepts eventually everyone gets on board.  There was so much conflict about the elimination of slavery that it nearly destroyed the United States, yet today except for a few truly evil individuals human trafficking is universally considered an abhorrent practice.    

Setting familial boundaries, business priorities, and state policy can all be highly volatile areas when different people come to “let’s not do that again” at different times.  This disparity can lead to extreme consequences such as getting divorced, fired, or in some cases getting shot.  If we were all like the Vulcans from Star Trek then logic would mitigate most of these issues.  The obvious answer would present itself universally to all parties.  We may all wish to “Live Long and Prosper” but we all see the route to that result very differently which is why the biggest problem with “Let’s not do that again” is the conflict when one person comes to that conclusion and others in their world haven’t yet.   

If you have ever been in that type of conflict personally or professionally you know it can be a brutal life experience, and one you only would want to have one time if you couldn’t avoid it all together.  The experience of a conflict over a “Let’s not do that again” decision is the ultimate “Let’s not do that again” in and of itself.   Unfortunately we are not kings and do not have dominion over everyone and everything in our lives. We need human connections to meet our interpersonal needs, and that means we will continue to have conflict when one of the parties decides they don’t want to repeat something and the other does.   

The only solution I have found includes beers with my friend lamenting the complex challenges of life and working together to figure out ways to minimize the number of times I repeat my mistakes in life.  Luckily for me that’s one thing we both enjoy doing again and again.   

Posted by Mike Peluso

Mike Peluso writes about the collision between between the business / professional world and life. He also writes about the journey involved with the Peluso Presents efforts including the Blog, Books, and Podcast so that others may benefit from his efforts. From Mike: I spend hundreds of hours working on these articles every year with no compensation other than support I get through donations. You can support with a tip and by Subscribing to the Podcast (and writing a review on iTunes would be really appreciated as well!) One time tips: www.paypal.me/pelusopresents https://venmo.com/pelusopresents


  1. […] the rest of the stuff and there is value in nearly everything you do, even if it’s just learning not to do that again. […]



  2. […] while ago, I wrote a bit of a high brow article all about the concept of not repeating our mistakes and really exploring why we sometimes attempt […]



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