Counting on Serendipity
Written: 04-03-2017

“Classical understanding is concerned with the piles and the basis for sorting and interrelating them. Romantic understanding is directed toward the handful of sand before the sorting begins. Both are valid ways of looking at the world although irreconcilable with each other.”

Zen and the Art of Motorcycle Maintenance.

I often try to be highly analytical about decision making. This is a fairly new approach to life and it continues to be more true as I get older. As a younger person, into my mid twenties, I made many decisions based on emotional responses and romantic notions. The major decisions I put through a process, such as creating pro / cons lists and seeking advice from others – but I relied on gut feelings to a great extent.

A side effect of this approach to life meant that I also relied upon the randomness of life. I have regularly supported the notion that many of the key individuals I have met in life, were a matter of serendipity. The following is a reflection on serendipity in my life as it relates to my career and dating.

When I think about my career, I can pin point most of the opportunities I’ve had to just a few individuals. At first reflection, I would say that each of these individuals were found serendipitously. They seem to have entered my life in ways that were random. That is the story that I have told myself this past year, as I have focused on becoming a more skilled product manager and developer. The discussion that I have had with myself many times, goes something like this:

Voice 1: Question: What do you need to do to make this career change?

Voice 2: Response: You need to be a lot better programmer, so spend time behind the computer getting better. Put in your ten thousand hours.

Voice 1: Ok, but ten thousand hours is a long time. Can you wait that long to start sharing those skills with people, letting people know what you can do today?

Voice 2: Don’t worry about sharing the skills. Just get good and people will find you, they’ll discover what you can do and it will lead to work and customers.

While I have this internal conversation, I know logically it’s not the truth. Counting on luck, is a pretty poor process to count on. It’s nice to have when it happens, but what should a person do until that time? I have felt empowered waiting on that serendipitous moment because of the stories I mentioned previously. I have a narrative that most of the truly impactful and life-changing moments I have had, were a matter of good fortune.

Let’s explore two of those stories:

After graduating from the University of Nebraska-Lincoln, I was like many graduates: searching and lost. I knew what I wanted to do, but very unclear on how to achieve it. The prospect of graduate school seemed like a great ‘next step’, however I was completely broke and burdened with student loans. I made the decision to search for a graduate assistantship through NIRSA. I also concluded that unless I could not attend graduate school for free, I wouldn’t go. I attended the NIRSA conference in San Antonio that year and ended up pursuing assistantships at many schools (it was encouraged to apply broadly while there), with my top four being: Colorado State, Oregon State, San Diego State and the University of Texas. In each case, I either didn’t get accepted, an assistantship or a full scholarship. I continued searching the NIRSA site ( daily and at some point an opportunity for the University of Kentucky opened up. At the time, the concept of moving east of the Mississippi River seemed incredibly unappealing, especially to Kentucky (not that I had ever been there).

I ended up applying, which lead to a phone interview with Beth Atnip. That call lead to an assistantship at the University of Kentucky. Beth becomes the key figure for my life as a Kentuckian. Not only because she brought me here for graduate school, because I left Kentucky as soon as I finished my masters degree. She was also the individual who spurred my return to Kentucky a little over a year later, when I moved from Colorado to Kentucky, because I returned to take her position at UK.

The story that I have been telling myself these past (nearly) 15 years is that meeting Beth was lucky on my part. It was definitely a bit of good fortune. As mentioned she has been the key to my life as a Kentuckian, but she and her husband Eric are also two of my best friends. That being said, while lucky, it wasn’t as random as I generally believe. I often forget about all the applications I sent to schools, interviews I completed, phone calls I made. Ultimately, making the decision to journey east of the Mississippi River despite the initial apprehension.

The second story is how I lucked into coaching Brad Feld. Brad is a well known venture capitalist that lives in Boulder, Colorado. It has definitely been a piece of good fortune. Much like meeting Beth it’s not only because what it’s meant for my career, but also due to the fact that he’s a really genuine person that you want to associate with. It seems an unlikely, random and lucky set of circumstances that allowed me to become his coach. I had to reflect on this during the Endurance Coaching Summit hosted by Training Peaks in 2015, when Brad was a keynote speaker and multiple coaches asked how I started coaching him.

While there was definitely some luck associated with it, it also required some time and effort on my part. One reason I knew of Brad was because his blog combined two topics that I was passionate about: technology and marathon running. I don’t recall how I found his blog, but one of my strongest memories was applying for his entry to the North Pole marathon he chose to give away. I didn’t win the entry. I remember reading his blog for a couple years, occasionally commenting on a post and observing his running from afar. In 2008, Nikki and I self published a book on strength training targeted at runners. One night I got the courage to send a copy of the book to Brad. I said something about getting a lot of value from his blog and that I thought he might get some value out of our book. I’m pretty sure I was hoping he’d enjoy the book enough that he’d share it with his blog readers. What ended up happening was an exchange where he asked about coaching.

I share both of these stories as case studies. They have both been examples of my good fortune, which I have mostly attributed to luck. There is definitely an element of luck, but they both required some action on my part.

In the most recent months, I’ve met three people: Thomas Cothran (August 2016), John Cothran (November 2016) and Aalap Majmudar (February 2017). Meeting all three of these guys could be attributed to random circumstances that have lead to changes in my life. However, many decisions were made and opportunities taken that lead to meeting them. Including having started my new career with new business partners.

Thomas, John and I have a metric that we highlight which is the number of ‘mentors and advisors’ we connect with on a weekly basis. While we’re struggling to find good ways to collect the data, it emphasizes the importance we place on connecting with people. One of the best books I’ve read on this topic is The Startup of You by Reid Hoffman and Ben Casnocha.

The mindset of someone ‘waiting on serendipity’ does not isolate itself to career changes and business relationships. I have spent a decent amount of time considering how this mindset is involved in other types of relationships, such as dating. In fact, I would say that it’s much easier to put yourself out there and take chances in a business context than most other contexts. In business we are often told that action and boldness are rewarded with success. In the realm of dating, it doesn’t seem that well supported, unless you’re running a dating application or service.

When you are dating, the consequences of failing can be a lot more painful.  When you put yourself out there and something doesn’t work out, it can easily be internalized as a personal failure and shortcoming . A person begins to believe they do not have the personality, the looks, or the status thats needed to successfully meet the person that they want to spend time with and commit to.

When this mindset is present, it can be easier to wait for something to just “happen” to you. When you struggle to make the connections that you want to make, it then becomes easier to sit back and blame ‘bad luck’. Luck is a much better and easier antagonist then to accept that failure will happen. Failure can happen and that it’s ok and not a specific assault on your character or who you are. It sucks, but it is ok.

The difficulty in overcoming this mindset is that we are told that “love happens”, that we have that ‘soul mate’. If both of those statements are true then we would do just as well if we waited until it happens to us. At best, taking action would be frivolous, wasted effort. At worst, we could impede the trajectory of the magic within our lives.

But what I have been trying to understand recently is, in a time of dating apps and sites, what does it mean to wait on serendipity verses making the effort to build a desired connection? Here are a few things that I’ve come up with… WOS = waiting on serendipity, PSC = proactively seeking connections

WOS: obsessively scanning social media, thinking that there will be someone or something that jumps off the screen

PSC: testing your ability to take the right actions and start conversations with people you want to connect with

WOS: believing that other people know your intensions even when your intentions are not stated, expecting a moment of enlightenment

PSC: understanding that intentionally made actions can end up with failed outcomes and that is ok. It is not a condemnation of who you are.   

I know that in my early dating life, I was not very good at the whole process. Some of this was that I felt like it would happen serendipitously. I also seemed to be very bad at the whole process when I tried to put forth effort. I had zero game or social awareness. I realize now that a big part of it was a result of anxiety (that was self managed with alcohol), which made the social interaction difficult. My other observation that I did not understand at the time was that when failure happened, it was information I could use as a lesson learned. I could then move forward by applying those lessons to the next action. Logic and romance rarely are used in the same stories. In most of my stories, I took failures as an assault on me as a person. I also wasn’t sure how to deal with rejection. To say that I was not very self aware as a individual in my early to mid twenties is probably an understatement.

To reinforce the narrative that serendipity was the force behind key individuals in my life, it seems quite random how I first came to the conclusion that Nikki and I might have an opportunity to develop a connection. It was August of 2003, school was getting fired back up at the University of Kentucky. I found myself waiting in line to get into Two Keys (a local college bar) with Josh Axe, when we saw Nikki and Kim Ahr (now Summers) also standing in line. We ended up spending the rest of the night hanging out. The story I have told myself is that it was a matter of chance, however that wouldn’t give any respect to all of the decisions and efforts made to that point.

It’s just simpler and easier to tell the romantic story. As the quote from Zen and the Art of Motorcycle Maintenance at the beginning of this reflection states, the classical and romantic understanding are irreconcilable with each other. The classical understanding is never a fun story to tell.

All of these life lessons and observations provide context as to why I believe it’s easy to fall into a trap of leaving life to chance. This approach gives us cover if things don’t work out the way we anticipate they should. It gives us an excuse to share when we appear apathetic or unmotivated to find things we care about, such as a job we enjoy or a relationship we desire. It is also a more romantic approach to living life, which can be an appealing and interesting way to live. However, I don’t see it working out as well as our fantasy would lead us to believe.

I will end with one last thought.

While counting on serendipity is a less productive way to approach living and having intentional actions is likely going to lead to more positive outcomes, I do not believe that planning all of life’s details is a good approach either. I do not want people to confuse my assertion that taking intentional actions is the same as creating deep and details life plans. I hope to share more on how I’ve changed my opinion on the value of life planning.

For the time being: live intentionally, yet remain aware and open to the randomness life provides.