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  • Brett Simpson

In my experience…I wish I had done it sooner


My wife used to have one of those colorful, semi-transparent iMacs (hers was teal) with a handle on top.  It felt and looked more like a bowling ball than a computer.  I didn’t care for the Mac OS at the time, instead preferring Windows, and was thrilled when we finally sold it to one of her friends.  From that day forward I only used Windows laptops, which despite the occasional blue screen of death, I was comfortable with since that’s what my employers issued.


During that time friends, colleagues, magazine ads and TV commercials kept telling me how much better Macs were than Windows machines.  I didn’t believe them.  Then I bought an iPhone.  My disdain for Apple had prevented me from buying one of the first several versions, so needless to say, I was on the backside of that adoption curve.  Shortly thereafter I bought an iPad.  With my iPhone and iPad in hand I decided to take the leap into total technology interoperability in October 2012.  I sold my Dell laptop and bought a MacBook Air.  I fretted over the decision, worried that I’d again hate the OS and had wasted my money.


As I write this story now on my one-year-old MacBook Pro I’ve had an epiphany.  In my experience, I wish I had done it sooner.  Twice now actually with MacBooks.  This isn’t an advertisement for Apple products, although they do work seamlessly together.  Rather, the point here is that I’m kicking myself for not making the switch earlier.  How many times have you said that about anything?  It doesn’t have to be as something as silly as a computer.


I’ve lost count of the number of conversations I’ve had where the other person said the words, “I wish I had done it sooner.”  Scenarios include but are not limited to:

  • Change jobs / employers

  • Hire / Fire someone

  • Learn / Try something new

  • Take a risk

  • Enter / Exit a relationship

  • Start / Terminate a business

  • Make a purchase

  • Begin exercising

  • Read a book


Cause for Pause

I’ve done every one of the items listed above and am confident most other people have as well.  At first glance, it may seem like I’m a slow decision-maker.  That may be true in some cases, but more often than not the hesitation is a result of an aversion to some actual or perceived risk associated with each scenario.  A less than certain outcome gives me cause for pause.


The more I encounter these types of scenarios the higher my tolerance for risk becomes as it pertains to making a decision.  Notice I didn’t say making a ‘tough’ decision.  While some decisions are tough, they become easier over time because they’re the right decisions.  Additionally, the decision-maker becomes more confident in the decisions made and their ability to handle a variety of potential outcomes.


Relief in the Result

Depending on the decision, switching costs may be high.  For example, deciding to change jobs causes more consternation than deciding to read a book.  Because of that we put ourselves though seemingly endless bouts of exploring the cost-benefit of each possible outcome.  Once the decision is made and someone says, “I wish I had done it sooner”, it’s because there’s relief in the result.


When the result meets or exceeds expectations, the conclusion is that the right decision was made.  Typically, that realization is followed by the unspoken promise to oneself that, “Next time I won’t put myself through that analysis hell.”  The challenge is that it’s rare that the exact same scenario with the same pluses and minuses arises more than once, so the decision may not be as easy as we want it to be, but at least we know we can handle making it.


I’ve found that the more I put myself in situations that require me to make decisions about change (even small change), the more comfortable I become making those decisions.  I expect and hope the result of this to be that I won’t be saying “I wish I had done it sooner” as often.


Special thanks to Jorge Cadenas, who I respect for his talent to turn new opportunities into successful realities, and to Chris Goode, whose ability to assess the viability of locations for his business and make the decision to stay-the-course or move-on is admirable.

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