Serendipity: A Perfect Ingredient to help Solve the Challenges Facing the 50Plus Demographic

   A "serendipitous" four peak day on Jan 10, 2016 near Portland, Oregon on a 2 hour drive never more than 45 miles from my front door all taken from Oregon vistas. Clockwise: Mt. Saint Helens, Mt. Rainier, Mt. Adams and Mt. Hood.


A "serendipitous" four peak day on Jan 10, 2016 near Portland, Oregon on a 2 hour drive never more than 45 miles from my front door all taken from Oregon vistas. Clockwise: Mt. Saint Helens, Mt. Rainier, Mt. Adams and Mt. Hood.

Serendipity was the subject of my first two blog posts in September and October 2013. Both posts were different takes on how we can create our own serendipity. I have been a long time believer in serendipity since I can point to a fair amount of it in my own life. I have had enough of it that I strongly believe there are a number of different ways you can increase your odds of experiencing it. I highly recommend conferences and other well chosen gatherings as starting points since they have been a primary source of serendipitous interactions with people, organizations and ideas that have changed my life. In most cases I likely would not have encountered them in any other way.

In 2015, as my focus for this blog shifted from millennials to the needs of the 50Plus demographic, I hadn't yet thought to touch on serendipity again. It was an article in the NY Times the week before last by Pagan Kennedy entitled Cultivating the Art of Serendipity that put it back on my radar screen. Her subtitle makes a point that caught my eye right away, "Innovation isn't all hard work or dumb luck: It's about paying attention". Kennedy’s timing was itself serendipitous because I quickly realized that I had overlooked that serendipity can be a key ingredient in helping the 50Plus demographic to face its major financial challenges in the coming years.

My message to the 110 million strong 50Plus demographic is this: we have to begin to embrace entrepreneurship to generate the additional income needed to overcome the structural problem of outliving our financial plans. In short, for many, “entrepreneurship will be a necessity, not a choice”. Just to be clear, when I use the term entrepreneurship I start with entrepreneurial thinking. Learning to think like an entrepreneur isn’t based on genetics, it is not a trait that you either inherited or you didn’t. It is a learned behavior accessible to all of us. I am not suggesting it is an easy learning curve, but I can speak from experience as a serial entrepreneur, as well as from teaching others, it can be done.

Tina Seelig, a leader of Stanford University's preeminent entrepreneurship program, provided a definition of entrepreneurship in her book Insight Out. In her words, “entrepreneurship involves building the knowledge, skills, and attitudes needed to see problems as opportunities and to leverage resources to bring ideas to fruition.” In her book, Seelig presents what she has dubbed the four part Invention Cycle. This cycle is  rooted in using curiosity to spur your imagination, which then seeds creativity to allow one to visualize innovations, which finally opens the door to the act of entrepreneurship to bring them to fruition. Seelig doesn’t mention serendipity. However, reflecting on the first part of Pagan Kennedy’s subtitle, “Innovation isn't all hard work or dumb luck”, I would suggest that "cultivated serendipity" is “smart luck”, which I assume is why Kennedy describes it as being, “about paying attention”. I would hold that smart luck based on paying attention is a perfect additive to the Invention Cycle. My gut says Seelig could agree with that.

The 50Plus demographic is loaded with experience, knowledge and well honed skills. Cultivating “smart luck” by paying attention with the right attitude seems like what the doctor ordered to get us on track to solving our own problems. If any demographic can do it, we can.

Having defined the scale of the problem in my last post, coming up with another key ingredient here, in the next few posts in this series I will explain my thoughts on how this all fits together and most importantly why I am confident that if we stay focused we can succeed in controlling our own destinies. It is not too late! I will share more details of my own experiences and those of others, including stories of folks who have cultivated serendipity in various ways to succeed as entrepreneurs. My focus is going to be heavily skewed towards micro-entrepreneurship, starting small to create our own jobs without taking huge financial risks. This is in contrast to trying to fulfill the dreams of economic development officials looking for the next Facebook, Google, Apple or sharing economy startup to create massive numbers of new jobs in their geography. I will emphasize that working smart in this day and age means acknowledging the power the Internet, not ignoring it. A few more posts will take us to the launch of my offering to the 50Plus community based on a new website later this month or in early February. I am excited to share it with you!

Stay tuned a little longer… the meantime please continue to comment here or e-mail me at




Diversity drives innovation .... don't forget age diversity .... #AgeDiversityMatters

    An unlikely athlete entirely changed the sport of the high jump via a simple innovation.   (AP Photo)


An unlikely athlete entirely changed the sport of the high jump via a simple innovation. (AP Photo)

My friend Roger Wu wrote an interesting and timely article this week on diversity and why it matters. Although Roger, an Asian-American, didn't believe diversity mattered growing up, founding his own startup quickly convinced him that it does matter. Leading his startup Roger came to understand clearly that diversity, broadly defined, is a key to innovation. Recognizing that innovative startups have been the engine of the US economy, creating the lion's share of jobs in recent decades, there should be no debate that innovation is critical to all of us. 

Silicon Valley, a major source of innovation, has been fielding lots of complaints of late about its utter lack of diversity. Look no further than the complete dominance of young white males on the upper rungs of the tech industry ladder. Are they the only ones with good ideas? If nothing else their dominance suggests that something is out of whack. Where are we going next, will we continue on the same path? Look at the current output of the tech community and what you see are, in Roger's words, "lots of startups attacking frivolous first world problems".  More apps for dating, other social needs satisfiable by seconds long bursts of images or words that often disappear, food ordering and a panoply of other "me too" products are being churned out by the dozens. If the goal is to actually change the world, it is time to get on the radio and tell Mission Control, "Houston we have a problem"! 

Roger goes on to provide numerous examples to demonstrate that we can improve our innovation outcomes with diversity of seeing, doing and thinking. There can be no doubt that our odds of real success degrade substantially without them. He concludes that there is hope because some early adopters in the startup world are beginning to push a range of diversity initiatives. However, the initiatives he highlights have to do with various incubator, bootcamp and accelerator programs emphasizing diversity of race, gender and sexual orientation. I don't discount any of those, they are all important. However, there is a jarring omission on this list - age diversity.

In my last blog post I began to focus on age, a theme I intend to stick with by actively covering the needs of the 50Plus demographic going forward. There are 108 million of us in the US alone. If we formed our own nation we would be the 12th most populated nation on earth. Most of us are getting ready to, or have already begun to, make major life changes. "Finding purpose" is high on the list of key attributes of what many of us want to do next which is why I entitled my first post on age Finding Purpose. My prescription for my 50Plus brethren on how to find purpose includes a strong dose of "entrepreneurial thinking". However, that same prescription can also apply to innovation. 

Let's face it, we are going to be around longer than most of us ever expected. We still have lots of current needs but will have new ones soon, some that are a direct result of the biological aging process, but others that will arise just because we have more time. Some of our needs going forward may be classified by other generations looking over our shoulders as frivolous but I know there will be a lot that can't. The elephant in the room is the fact that not all of us made the financial plans needed to make it through the extra decades we are likely to have. Alternative sources of income are going to be a critical need that many will have to address while also searching for purpose. There is no question that we are going to have to innovate.

Who is going to drive this innovation? Technology will undoubtably play a role in many solutions given the pervasiveness of the web, tools based on the web or connected to the cloud via the web. I am not going to wait for a homogeneous team of millennial males in Silicon Valley to read our minds. Don't be afraid to step up. Join me and let's collectively lead innovations, tech-based and otherwise, to solve our own problems and fill our needs. We all have an "inner entrepreneur", not all the same, but very valuable when it's unleashed. Whatever we do it's important to take to heart the lesson of Roger's article and avoid taking too narrow a view. We need to gather in small groups purposely diverse on as many dimensions as makes sense, include younger and even older generations and take advantage of everyone's experience, talent and knowledge.

#DiversityMatters   /   #AgeDiversityMatters


Creating serendipity ....

I spent Friday and Saturday this week at a truly amazing conference, the Work Revolution Summit (WRS) at the Center for Social Innovation in NYC.  Jessica Lawrence Executive Director of the NY Tech Meetup (NYTM), Julie Clow and Josh Dykstra of Work Revolution, with lots of help from Andy Saldana, organized the gathering. I am a big believer in creating one's own serendipity. WRS for me was true serendipity.