Do You Plan For Serendipity?

Do You Plan For Serendipity?Some see serendipity as the hand of God. That divine intervention that saves or changes an outcome for the better. Others view it as pure luck, incredible coincidence or a happy chance.

For me, serendipity is none of those things. Serendipity is what happens when you are ready for change, open to innovation and informed about possibilities. Serendipity should mean a careful assessment of circumstances that then inform action.  Serendipity is also about stepping back and allowing natural curiosity and conversation to flow. It is only luck to those who can’t see the links between ideas, events and outcomes.

Not only do I NOT think serendipity is accidental, I would argue that we should think, plan and train for serendipity. In popular culture the word serendipity has come to mean a lucky discovery, while the origin of the word is something quite different.  The story of “The Three Princes of Serendip” is widely held to be the origin of the word serendipity. In the story, a king instructs a select group of tutors to educate the three princes in their collective wisdom. When the tutors feel that they have taught the princes all that they can, they are presented to their father.  Although the king is proud of their wisdom, he feels that they have been too sheltered and so sends his sons off into the real world.

The princes very quickly encounter a number of adventures and use keen observation and what later becomes the basis of the scientific method to discover the truth behind a number of mysteries.  The stories of the three princes can be considered the origins of the detective story. In fact, the observations of the princes bear more resemblance to the behavior of Sherlock Holmes than they do to lucky discovery. Which brings us back to our current use of the word.

Serendipity is about being curious and observing all information, not just those bits that fit comfortably within your own paradigm. It’s also about being informed. It’s impossible to apply deductive reasoning or even to see the relationship between events if you are not informed. Encouraging curiosity and allowing yourself to follow your nose to see what you discover is a great way to cultivate serendipity.

A few years ago I was attending a board meeting in Vancouver. Early on the second day I woke up as the phone rang in my hotel room.  It was my assistant calling me to tell me to look at the national newspaper before going downstairs to my board meeting. The story on the cover of the newspaper was one that would have my board members concerned. Rather than walking into an explosive situation unprepared, that phone call meant that I had time to gather information and do the necessary preparation to deal with their concerns coherently. As I walked into the room for our early breakfast meeting, I was calm as I knew how we could manage the unfolding events. My board members might have thought we were lucky, but  I knew that my assistant was smart enough to know that the newspaper article could critically derail our meeting if I was unable to leverage serendipity.

When employees find simple solutions to complex problems or seize on opportunities, there is often a temptation to consider those outcomes, lucky. That’s a dangerous response to innovative behaviour.  When we fail to recognize innovative behaviour, it’s like saying, don’t employ knowledge, experience and insight. Instead hope for luck. We know that when good behaviour is rewarded, it is repeated, so if we discourage the kind of inquisitive assessment necessary to make serendipitous events positive, then we risk missing out on transformative discoveries.  Discoveries like Aspirin, insulin, antihistamines, Scotchgard, Teflon, Velcro, Nylon and the Post-It Note.

Do you give yourself enough time to cultivate serendipity?

Image courtesy of Chaiwat /

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0 responses to “Do You Plan For Serendipity?

  • Arleen says:
    June 10, 2014 @ 12:26 pm

    I think we need to take advantage of unexpected surprises. I think that many of us do not succeed without the assistance of the unexpected. which happened to you before your conference. But as successful people we can also enjoy the skills of planned serendipity. A very thought thinking post.

  • I watched the movie “Serendipity” a couple of times in my life. I thought it was funny how the two kept meeting accidentally. It was like fate.

    In my life, I’m kind of like Jeri, always on the lookout for the next bit of good fortune to come my way. 😉

  • An enjoyable read, Debra. I fully agree with the power of preparation and the conscious creation of the right conditions as key influences for what is sometimes confused with happenstance. Still, every now and then, we seem to inexplicably wind up in the right place at the right time, or catch a happy accident that seems to transcend preparation and foresight. For me, those are the occasions when ‘serendipity’ comes to mind.

  • I Love the word serendipity. It brings back memories of when my young son learnt the word at school and was trying to explain the meaning to me. He is young and ambitious and willing to take a risk and I think the word suits him.

  • I’ve never really applied that word to my general way of living life mode, but now that I’ve read this post, I would say I do cultivate the opportunity for such chances, but not that I’m ever satisfied because I’m always on the lookout for the next bit of luck.

    • I think the very act of always looking means that you’re always in a position to find it. I don’t think of passivity as a trait that will draw serendipitous events. 🙂

  • I believe in preparation. If you prepare yourself for what ever it is your trying to accomplish you will be ready when the opportunity calls. I think many people believe serendipity happens by accident because they are not prepared. I love this post. I’m definitely working on serendipity.

    • There is something about waiting around and hoping something good will happen that feels pointless to me. Like you, I’d much rather stay alert and open to the possibilities while preparing myself for whatever comes next.

  • Hey Debra,

    I always looked at the definition of serendipity as finding desirable things by accident but I don’t believe in accidents. Although it’s really hard to stand by the saying that everything happens for a reason I do believe that things are planned. Most of the things that happen to us in life are suppose to whether we see them as such or not.

    I really haven’t given this much thought if I’m honest but because this is my belief then I would have to say no. Nothing as of late has come into my life in such a manner.

    I think that your definition is great though, it suits you just fine and it’s just like the example you gave with your assistant calling you. She was doing her job and looking out for you so I applaud her.

    Thanks Debra for sharing your views with us.


    • Thanks Adrienne. Your blog was a bit of serendipity for me. I kept coming across your comments on other blogs that I regularly visit and wondered, “Who is this lady?” Then, Susan Cooper did a guest posts and decided to go read it and voila, I was on you blog. Serendipity. 🙂

  • Hi Debra; I like what you are saying. sherlock holmes was successful because he was able to see the smallest detail and use it to build a theory that would solve the crime. I think I am open to possibilities but I don’t know that I notice all the small details that I should. I do listen with my full attention and whole heart and keep myself open to possibilities. I have ben blessed with many good friends who have helped me on my way simply by staying open. thanks for the history lesson and clearing up the meaning of serendipity. take care, Max

    • Max to me, you epitomize someone who plans for serendipity. You are always seeing and seizing opportunities. Where many people might hesitate or be reluctant, you jump in. I think that’s why you have such a wide network of people keen to support you.

  • Meredith says:
    June 5, 2014 @ 11:35 am

    This reminds me of the saying “Fortune favors the prepared.” I like your definition of serendipity better than the common usage that equates it to luck, which makes it seem arbitrary and capricious. Being in the right place at the right time usually takes a lot more planning that that!

    • I’m a big fan of that expression. I tell my colleagues to prepare for the worst and hope for the best, by doing that we are always ready to deflect challenges or take advantage of opportunity.

  • I love serendipity. It comes into play so often when traveling or trying new things.

  • jankedonna says:
    June 5, 2014 @ 10:50 am

    Planning for serendipity may seem an oxymoron, but I agree you can cultivate it by being open to things, observing the world around us, taking time to think and let the mind wander, and by journaling.

    • I really like the idea of journaling as a way to capture elusive links or solutions. When I kept a journal I found that I would discover patterns in my behaviour that I was unaware of, but by looking back at the journal entries over time they became obvious.

  • I think it is important that we embrace situations that bring about a bit of uncertainty. Although it is not easy, we learn so much by trying new things and preparing for change. Thank you for sharing!

    • Karoly, that sounds like an amazing way to live. Keeping yourself open to the opportunities that life makes available is bound to to take you to some interesting places.

  • I really enjoyed reading your post. I think often times we are too scared of the unknown and we miss out on a lot. I have of late been living in a serendipitous way and I am learning so much. Instead of freezing at the change of something new, I am making my way and enjoying the process. Thank you for sharing!

  • Hi Debra – first, thanks for the origin of the word serendipity – I love the word. Reading your definition of serendipity made me look up at a plaque I have on my desk. “When one door closes, another opes; but we often look so long and so regretfully upon the closed door that we do not see the one which has opened for us” by Alexander Graham Bell. Looking back at the closed door I think means we don’t engage serendipity.

    • Lenie I love the expression on your plaque. Whenever I start to get frustrated with a situation I try to ask myself what the benefit of it is. What am I being taught or what am I being saved from?

  • I always believe we can make our own luck..Proper planning and execution is the key. Most of the time it is the result of a number of actions which people term as luck. But again, there are some instances which testifies the fact that pure luck too exists.

    • I completely believe in pure luck, stuff happens. I was thinking that we could have more lucky streaks if we left ourselves open to possibilities. That’s where serendipity shows up, it’s our ability to see the possibilities and implications in the events that are unfolding around us.

  • Hi Debra, I did not know of the origins of the word at all. I have understood it to be when desirable circumstances come together to give a even more desirable outcome. In fact writing that was difficult as my understanding is not easy to articulate.

    I Googled the word just now and Wikipedia said The word has been voted one of the ten English words hardest to translate – that made me feel better!

    In answer to your question no I do not give myself enough time to create it. Having said that I am always open to innovation and mostly ready for change.

    A very thought provoking post.


  • To me, hard work and fore thought are the keystones to any successful venture; be it a business, a relationship, your health, whatever. It cannot be denied though that good fortune plays a part; the extent to which you attract it or fall into it is up for debate. To completely rely on fortune to shine on you is not good but neither is pretending that all success is 100% hard work. They work in tandem. It just depends on how much of the pie you are willing to put into work and how much you are willing to rely on luck.

    • I think that’s a good assessment Tim. Defining anything that is a reflection of complex parts is tricky. It’s all about finding that balance and recognizing that it’s not a simple answer.

  • Great post, Debra. I am very much in favour of rewarding innovative thinking. It’s so unfortunate that often, it is discouraged in governmental environments, as employees are afraid to ‘Rock the boat.’ There is much more flexibility in the private sector.

    • Well said. We create environments that either encourage innovation and creativity and subsequently have more serendipity or we create environments that are about following the rules and not looking outside the stated parameters.

  • First to answer your question: I have not of late. My mind has been way to cluttered with the consolidation of the two homes to allow for that. Second, I love and agree with the concept that serendipity is about being curious and observing. To often we stay within your own comfort zone because it’s safe. When we do that we miss the opportunities (and solutions) that are circling around us. Just my thoughts. 🙂

    • I agree Susan, when I start thinking feeling safe is the only objective then I know I’m missing out on a ton of good things.The same can be said about being so busy that we don’t have time to reflect.

  • In my mind, the word “serendipity” is uplifting and positive, with a feeling of excitement that something really great is about to happen when I turn the corner!

    • Serendipity is definitely about positive outcomes to me too. I think your anticipation of something great around the corner is what lets you see the opportunity.

  • Hi Debra. I agree that to a very great extent we “make our own luck”. It seems clear to me that serendipity stems from the story of the princes but I now use the word with caution because it is so frequently interpreted in a random sense. On a collaborative basis I think serendipity has much in common with an improv session that leads to great jazz; to treat the magical result as merely fortunate overlooks all of the practice, experience and skill that precedes it and the awareness and observation that causes it to gel. Another great post. I love it when you deal with these universal issues !

    • Paul my husband hates the word because it is so overused and so little understood. I think part of it’s popularity and many interpretations is because so much of how serendipity works is a mixture of luck and the ability to to take advantage of opportunity. Your example of a jazz group having a good improv session is a beautiful one.

  • I agree with you and then I don’t agree with you. To me, serendipity is coming up with a solution by using what is available both physically and mentally but, by pure luck, it works.

    • I think it’s interesting that you equate your innovation of coming up with a successful solution based on what’s available as luck. I think it’s a reflection of your experience and ability to problem solve. We’ll agree to agree and differ. 🙂

  • My father used to tell me all the time…be good, be careful and be curious. I’ve always believed that curiosity is the mother of invention and agree that it quite often births what we now know as serendipity. There is no substitute for careful planning and I think you’ve made a great case for controlling outcomes rather than being controlled by them. Love knowing the history of the word too!

    • I totally agree about curiosity Jacqueline. That little fire that makes you want to learn more is the same thing that sparks innovation. It means that when events unfold, rather than being a passive recipient or observer, you engage because your asking, “what’s this all about, why did that happen, what can we do with that….”

  • Have the same opinion as you on serendipity. We have to be flexible and be prepared to seize unexpected opportunities when we come across them. By the way, another person with the same outlook on serendipity was Potemkin. As you know he was the power behind Catherine The Great and a lot of their successes was thanks to serendipity.

  • I had no idea the origin and story of the word serendipity. I think of serendipity as fate, the Universe being aligned in order for certain events to unfold that will impact a situation positively and unexpectedly – kind of like your assistant calling you on that day. Enjoyed this very much and glad you shared it with us.

    • I think the world is always working for us or against us, It’s up to us to decide which way we want it to work. For me, our outcomes are a reflection of how we respond and anticipate what we’re presented with.

  • For me serendipity is a pure idea that there are charmed moments when stars align and the dice roll in our favor. If you can plan for it, it is not serendipity.

    • Ian a few years back Timberland, a company that made tough boots for construction workers saw a massive spike in their sales when young rap artists and their followers started wearing their boots. That’s luck. When the head of the company was asked about his new customers and the multi-million dollar jump in business, he said, “Everyone’s money is good, but we build boots for hard working people.”

      His response insulted and outraged the very people who had helped him triple sales.That’s not planning for serendipity. 🙂

  • We used to have a cat named Serendipity. I know, off topic but I figured it should be said.

    (Pulling out some geek cred here) there are no coincidences when you follow the ways of the force. Those who prepare and work are the ones who move ahead.

    The standard belief is luck. Sure occasionally some people get lucky, they have there moment in the sun and you never hear from them again. But then there are people who build there own luck. They work everyday to get better. You may or may not ever hear about them but they sustain so much longer than the flash in the pans.

    Did I manage to stay on topic?

    • Of course you had a cat named serendipity and yes, it had to be said. 🙂 You also stayed on topic.

      I’m always a little astounded when incredibly successful people are labelled lucky. Winning a lottery is lucky. Building a successful business by taking advantage of a trend is about spotting an opportunity and acting on it.

  • Debra — your post struck home because my late husband called his private press “Serendipity.” He had a zest for living and learning. He had a contagious enthusiasm when he learned something new. I agree, when we say something happened serendipitously, we’ve probably put ourselves in a place where it was impossible not to happen.

    • Jeanette, your late husband sounds like a fantastic person. I’m always drawn to people who run at life full on. We are all here for a short time so we might as well make the most it.

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