Being focused and productive within a distracting and noisy day

In a world that is full of distractions it can be challenging to find the space to work uninterrupted. The physical space or mental space. To be effective and have a high work rate, I find that it requires consistent stretches of time that is interruption free. This is especially true when I am writing or programming. Since the Awesome Inc Web Development Bootcamp started, I have worked at fine-tuning how I can achieve such an environment. At the moment, I have found a system, that works for me. Here is my current process, I hope that it gives you some ideas. I would love to hear your process, if you are trying to work on your productivity.

Taste, Smell.

The first step I take in creating the right environment is to think about all the senses and how they can impact the work. I do not normally have to worry about taste or smell, however I do like to sit in A Cup of Commonwealth to write. The smell of coffee shops is wonderful, plus I tend to drink a lot of coffee and their coffee is much better than anything I ever brew myself.


What about the distractions created by other customers? When I am at a coffee shop, I almost never program. I instead spend that time writing (as I am right now). The advantage of  doing this is that I can close my eyes and type without looking at the screen. This is a trick that I picked up from Luke Murray when he came and spoke to the bootcamp. The idea being that when you look at the screen while you write, your mind is on constant edit mode. It causes your writing to be slower and overly critiqued. On a first draft, the idea of being overly critical is not a good one. By closing my eyes to write, I can just work on letting the thoughts make it to the screen, I then go back and edit at least once, sometimes more. (This post is pretty basic, so it’s had one edit). The only distraction I have with this part of my process is that I can begin to feel self conscious as I type in public with my eyes closed.

When I need to program, I have to be in a different setting to optimize things visually. I have not yet figured out how to effectively and productively program with my eyes closed (still working on the eyes open programming). I also love to have multiple monitors when I code. That way I can have the editor (currently using Atom) and terminal open on one screen, with another screen free to run a browser.

To minimize the visual distractions, I also turn on the mac’s ‘Do Not Disturb’ setting, along with closing any messaging applications such as iMessage, Slack and Riot. Having the little notification number go from zero to 1, or 1 to 5 becomes very difficult to ignore when you are trying to be focused.


I can be distracted by visual pollution, however I have found that sound is a much bigger problem. In the coffee shop it is the sound of customers ordering an interesting drink, or the random conversation by strangers that you want to avoid but don’t seem to be able to. In order to fix this I always try to write and program with headphones on, listening to Spotify. Here are some of the things I have done to optimize this:

1. I used to use my standard Apple headphones, but I often found noise leaking into my bubble. I ended up getting some Beats Headphones, which was a major improvement. At some point, I could see the investment in some noise cancelling, over the ear headphones being another step forward.

2. I listen to the Spotify ‘Focus’ channels. I change it up at times, but my three favorite channels tend to be “Chill.Out.Brain”, “Deep Focus” and “Mellow Beats”. I use these channels because they are background tracks to my work, which do not include song lyrics. I have tried to use normal channels with music I like to listen to, however the right song can really ruin my concentration. I can be writing a post about productivity hacks one minute, then be taken to an old dirt road back home the next and be completely lost. That doesn’t happen with the tracks on the focus channel. A second upgrade I recently made was to start paying for Spotify Premium. I found that the commercials were interrupting my concentration, so for $10 a month I solved that issue. I listen to Spotify at home on my Amazon Echo and when I run on my iPhone, so $10 a month is amazingly cheap, in my opinion.


The only requirement that I have in regards to touch, is making sure that the chair I am sitting in is satisfactory. I don’t require a super comfortable seat, but something that is comfortable enough that I can sit for 25 minutes at a time and feel like I’m not being tortured is helpful.

Managing time and focus.

No matter what type of environment I have created to write or program, I can only maintain focus for so long before my mind begins to drift into another place or time. This is something I used to fight, but today I just accept that it is human nature. I know that there is a decent amount of research on the topic. For performance in athletics, I used to study all I could on getting into a Flow State (read ‘Rise of Superman’ if you are interested). I would love to say that getting into a flow state, where time disappears was a common practice, but that has not been reality. Therefore, I take advantage of this understanding and utilize it.

I use a pomodoro timer to manage these “focus” and “relax” periods throughout the day. I have my timer set for 25 minutes of focus, with 5 minutes of break time. This has been effective for me. Thomas also uses a pomodoro timer, which I believe he has his set to 15 minutes of focus and 5 minutes of relaxing. I would encourage everyone to test out using a timer and see how it works for them. Once you have determined if using the timer is something you want to stick with, begin to test different intervals and find where you feel most productive.

A tip that I have learned from Thomas, has been to use that 5 minutes of relaxing to completely shift the type of activity I am doing. When I am programming, I am thinking logically and trying to solve puzzles, therefore I try and switch to something that is less analytical. During the bootcamp, I would stand around and talk programming during breaks with other students. I didn’t think about it at the time, but it didn’t give my mind the space it needed. I have completely copied Thomas’ approach, which is to read something different during the breaks. I am currently working through ‘Zen and the Art of Motorcycle Maintenance’.

What have been the benefits of working in this way:

I don’t use this process for all of my work. For example, I do not always use a timer while I am answering email or responding to various networking pings. I use this process when I have work to get done that needs focus, consistency and progress. I have enjoyed the habit of using the timer, because it creates a process that I can repeat each day. It makes the days that I don’t feel like sitting down and programming or writing much easier to initiate. In many ways, it is similar to the run/walk strategy that I have used to coach some of the runners I have helped finish marathons. A task is much easier to start when the challenge is to run 2 miles (or whatever your splits are), then take a break and reassess, compared to getting started with the task of running 26.2 miles. The same is for my 25 minutes of focus.

The other benefit to this process is tracking my productivity. By using the pomodoro timer, I have a log of how many cycles it takes to work on a project. For example, I’m 2 cycles and 20 minutes into writing and editing this post, completed over two days. This type of tracking allows me to manage how I allocate my time and look back on how it matches what my intentions are. To continue with this writing example, I have a goal to do some personal writing for two pomodoro cycles each day (a total of 1 hour). I can see that this week, I have only accomplished it 2 of the 5 days.

Creating an environment where you can be successful, productive and focused can be a challenge in a world designed to distract you. Hopefully some of these ideas are helpful, if you have similar needs for your work environment that I have. If you have other ways to improve upon this practice or processes, I would love to hear them.

Reflections from the waiting room: When is it ok to not be ok and other fake new.

Not that long ago I was sitting in the waiting room, waiting for my father to get out of his quadruple bypass surgery. It had been a pretty stressful week and in many cases I was able to handle the stress. That is, on the outside when people would ask how I was doing. When asked this question, I default to two answers: “I’m doing well” and “busy”. The only accepted negative feelings that I feel comfortable enough to share are when I say something to the effect of “I feel like crap.” Or “my body really hurts”.

These responses are mostly a culturally learned response. At least that is the way I understand it from many hours of reflection and some therapy. As I grew up in a rural town in Nebraska, it wasn’t common for men to walk around talking about how they felt. How they were depressed, anxious or sad. I always felt like a pretty emotional kid and learning how to stuff those emotions was part of growing up. The four most prominent methods that I saw people around me use to avoid their feelings were:

1. Religion. I learned that being sad, anxious or depressed probably meant you were not faithful enough and needed to simply trust that God would take care of you.

2. Alcohol. Self medicating with alcohol is something I became good at pretty early, especially to manage anxiety related to social settings.

3. Being busy. If I had time to worry and be sad, I began to feel guilty that I wasn’t being productive enough. Time should be spent more wisely than worrying about things.

4. Anger. While it is an emotion, it’s not an incredibly productive one. It is however an emotion that was tolerated for the most part. This is especially true if it was in response to some socially supported endeavor such as responding to an athletic event as a player or fan.

The reason that I share all of these lessons is to set up an exchange I had the week that I left for Kansas, which had me feeling guilty for weeks. I had a local runner reach out to ask when the spring training group was about to start. It was a fair question, however given my stress levels, I responded by laying out all the emotional baggage I had been storing.

I shared that since Thanksgiving I had been dealing with the decision that Nikki and my separation was permanent and moving forward with the divorce, unsuccessfully finding new employment in a health related field after the Bootcamp, starting two new companies to pursue this new career and was preparing to leave for Kansas to be there for my father’s surgery. I summarized all the issues, by stating that I was currently overwhelmed and hadn’t been able to get everything together.

It felt good for a minute or two after I pushed send. Then I began to feel incredibly guilty and anxious. I felt guilty because it seemed highly inappropriate to share all of these issues with her, even if I had known her for nearly six years. I felt anxious because I worried how she would respond. Would she want to trust me as a coach? Would she think less of me?

Generating my own fake news:

Through the reflections and self inspection over the past year, I have come to realize that I am really good at generating fake stories by responding to people the way I do. I respond in the ways I do, for all the reasons mentioned above, but it clearly is not always accurate or true. In this way, I realize that I am good at generating fake news regarding my own life. I imagine that I’m good enough that, at times, I begin to believe the false narrative myself.

I create these narratives through Facebook posts, Instagram photos, daily interactions with friends and random responses to strangers. In many ways, I justify this process because I see it as a necessary part of ‘branding’ myself as successful, healthy and happy. It fells necessary to get a new client, fit into social circles and to relieve awkwardness of tough conversations.  The challenge is that by creating this false narrative, I never open myself up to friends and family, who can provide support when I need it.

When the narrative needs to be managed.

I have never been diagnosed with depression or anxiety. I have never been prescribed any medications by a professional to alleviate a depressed mood or state of anxiousness. But then again, due to the stigma associated with both of those, and based on the cultural learning that “Boys don’t cry” I have never been willing to seek out any help when I’ve had periods of unhappiness. Almost two years ago I started seeing a counselor to understand my unhappy marriage, and I can say with strong conviction, it’s one of the best things I have ever done. I wish I could have had the courage to seek out a therapist years ago to just deal with things I’ve wanted to deal with, along with uncovering the things I didn’t know I needed to.

If there’s one lesson in this whole story that I hope you take away, it’s that the stigma associated with depression and anxiety is nonsense. It’s a real issue and seeking supportive environments is always worth the effort. Much better than trying to self medicate and self manage.

I can recall a few times in my life where things felt like they sunk into a deep, deep pit that became difficult to climb out of. The one time that is the most prominent in my memory started in 2011. I have spent a lot of time contemplating, reflecting and stumbling over the reasons why it happened. I have some theories on why this period occurred, but the more important piece to this story is not about the cause, but the response. At the time, I was actively seeking a job. I had been working on Endurance Base Camp for around 5 years and it was doing ok, but with Nikki returning to school, it wasn’t sustainable. Part of that situation was that a majority of the revenue was brought in through personal training clients at Fitness Plus. One truth about falling into a depressed state and increasing anxiety is that the last thing you want to do is spend all day talking to people, specifically when they expect you to be the energetic, motivated and happy person they need you to be.

Having a life full of good fortune, I became very lucky. I was able to get a job at Retrofit as the Lead Exercise Physiologist. In so many ways, it was the job I wanted. It allowed me to pursue and understand the technology side of fitness and wellness more deeply. I was able to join a team of people who wanted to change people’s lives and create a great company. This was a big difference to the years of being a one-man executive team. It also was my first experience working with a startup that followed the traditional investor and venture capital path of startups. Everything I had ever done was bootstrapped.

I went into the position with a lot of hope, that a new job, a change in daily routine, a steady source of income and a new challenge would allow me to:  “wake up”. The reality was that for months after I joined Retrofit, things got much worse. It became really easy to find ways to create an environment that only increased the depressed moods. At Retrofit, I worked remotely with occasional trips to the home office in Chicago. This meant that I lived in my basement for many hours a day, with some days having no human interactions with others, which wasn’t done via Skype. Many days the only person I would talk to would be the barista at the drive through coffee shop that Kelty and I walked to.  During this time, Nikki and I developed very different schedules. She had school, where she’d be gone by the time I woke up. I had work and would often leave my office after she’d gone to sleep.

At the time, I thought this isolation was a good thing for me. I of course didn’t have the awareness at the time to realize this was happening. In the moment, I found myself just telling friends and family that I was “busy” with my new job. While there may have been an element of truth to the story, I also used it as cover to avoid nearly all social gatherings. This was despite Nikki and friends trying to get me involved in various activities on a regular basis. Here are some pretty obvious things that happened during that time that I can now look back on that are examples of this period:

  • After training for and racing in triathlons for over a decade, I stopped. I used the excuse that it was too expensive and I didn’t have the time to appropriately train. Deciding to quit triathlons removed a lot of my social interactions. I no longer had group rides nor swim lanes to share.
  • I stopped taking most phone calls. I still don’t like talking on the phone, but it became a standard to never have my ringer on or return a call. I’d often ask people to text or email.
  • I kept a couple personal training clients early in my time at Retrofit, but I ended up stopping all training within the first 6 months.

The biggest issue with this period is that I was able to hide how I really felt and how big the hole really was, by creating my own fake news. If you look back on my social media posts during this period of time, it’s unlikely that you’d find anything that hinted at my mindset. I painted a picture of being happy, healthy and successful. When I look at my life at that time, I would love to be able to go back and ask, “Why are you not happy”. Everything that a person might want in life was present: family, friends, challenging work, interesting hobbies and financial stability.

Asking the question, “Why”, is a natural response that I would have when someone is depressed or anxious. I used to think that it was the central question to ask when someone was feeling this way. Once we know the reason why, we can get busy trying to fix it. My reasoning was that if you are feeling depressed something is wrong and when things are wrong we should make them right. That is what I used to believe.

I do not want to make this reflection to become an analysis of why I became depressed. I also do not want it to become a self help discussion, where I share the various activities and methodologies I used to finally break free. The truth is that any observation would be a retrospective analysis, where I would have to make meaning out of actions that more than likely are not associated with one another. For now, I’ll keep those theories to myself.

What I want this to be is a simple reflection upon a time period in my life where I was depressed and anxious.

I started the reflection with one question: “When is it ok, to not be ok?” In various conversations over the past year, I have heard people make strong statements about others who open up about their negative feelings on social media. I will admit that I also feel uncomfortable when I read a status update where someone shares their sadness. I also see the courage it takes to willingly share these emotions. I have come to the conclusion that if we are going to accept Spring Break photos, vacation get-a-ways, sporting events, engagements, graduations and all of the happy moments in life, then maybe we should also be a little more accepting of someone sharing the challenging moments also.

My only hope is that a person that feels this way finds additional supportive environments and people to engage. Identifying these emotions and sharing them is a great place to start, however I do not know of any support systems that effectively help people manage depression and anxiety via social media as the only channel.

Shaking Free.

Sometime around November of 2012 I started to come out from under the cloud. When I think back to this period, I remember a co-worker asking me what I did to handle the work stress in a much better way than I had been the previous 5 months. I recall my response at the time, but I think it was wrong. I believe the answer was that I had finally started to shake free from being in the depressed mood. I do not know if that is a good analogy, to ‘shake free’, but that is what I recall it feeling like. Responding to life’s daily stresses and challenges becomes more manageable when there isn’t an underlying depressed mood.

By spring of 2013, I was finally in a place with a stable mood. That being said, the period did not end without a variety of side effects. The habit of responding to people with “busy” did not stop. It actually is one habit that may have became more common place. Recently, one of my best friends asked me: “Did I do something?” He was referring to the fact that we had historically talked very frequently. The calls were often long meandering discussions about all of life’s activities. However, the last few years we’d only talked a couple of times.

The after effects are something that will likely take time and forgiveness. The forgiveness that is most needed, is not from others, but from myself. An understanding that this period was not a failure of character or something to hide from. It was something that I went through, that has made me a more complete and better person today because of the insights I have gained from it. I only hope that should something similar happen in the future, that I will be less ashamed and more willing to share those emotions in the moment.

I have the same wish for others. If this is you, that you feel less shame and thoughts of failure regarding how you feel, and an openness to share those emotions. I am confident in saying that no matter how challenging the moods are to manage, no matter how alone they make you feel, there is someone that has empathy for your situation. There is someone who cares.

Kelty, the Black Swan

The other day I wrote a post about waiting on serendipity, and that it can be an ineffective approach to living. Waiting on serendipity can be a romantic narrative, but unless one has the emotional ability to manage the swings, it can be a challenge. The other lesson, from Zen and the Art of Motorcycle Maintenance was that the classical and romantic understandings are not able to mutually exist. Therefore, it’s also valuable to understand which type of understanding you lean towards.

I was thinking about another fairly important character in the storyline of my life, my dog Kelty. If truth be told, she’s probably been one of the central beings in my life. I was thinking about her introduction into my life in terms of randomness versus intentional action. She was a clear result of taking an intentional action, both on my part and her rescuer’s, Nikki. The reason that this story is worth sharing is that my intentionally made efforts were not in an attempt to adopt her, but in an effort to discourage her adoption.

It’s almost painful to write that, as I think about it today.

At the time I was just getting started on my first ‘real’ job post graduate school. Living in a small one bedroom apartment in Divide, Colorado working for the Teller County Public Health Department. Nikki was living in Lexington, working on finishing her masters degree. The hope I had at the time was that Nikki would be moving to Colorado as soon as she finished. I do not remember the timeline accurately, but the condensed storyline is that I thought adopting a dog made that transition harder. Nikki thought otherwise and adopted her.

I don’t have a list of cons I had for adopting a dog, but here were a few that I can recall:

  • It will limit the ability to travel, because it will need someone to watch after it.
  • If it travels with us, we will be limited to activities that could happen while it was in the car.
  • My landlord doesn’t allow dogs and it’s hard to find one who does. It’s impossible in Divide (given I lived in the only rentals there).
  • It will require a ton of attention and effort to train.
  • It will cost a lot of money to feed, take to vet, etc.

I probably had a lot of other reasons I would share when discussing the issue, but those were the big reasons why I didn’t want a dog. It’s always nice to be able to look back and realize that you are wrong, especially when you were wrong and the outcome was very positive. Here’s what ended up happening:

Nikki and Kelty moved to Colorado. Nikki ended up living with a co-worker of mine in Woodland Park, while Kelty came to live with me. My landlord never knew and for the most part, it was never an issue. Kelty took nearly zero training, as she was already house broken. She had some anxiety when she first lived with me, but after a short period she grew to be more relaxed. I worked in an office that was under my apartment, so I’d often see her looking out the window at me as I walked around the building and into the office (or she could have been checking out the beautiful views of Pikes Peak I had out my sliding glass doors?). We also started going for daily runs together at the Divide Park across the highway. It was an open field with an approximately 2.5 mile trail and unobstructed views of Pikes Peak. I’d run a couple laps, while she’d run circles around me the whole time. She acclimated to the 9,200 ft. elevation in a much better way than I did! On weekends, we would find trails to run together. I think her favorites were at the Crags which were not that far away, but presented wonderful views once you reached the summits.

Kelty was a great runner, which might be one of the reasons we got along so well, so quickly. My hard lined opinion about not having dogs, especially a ‘house dog’ quickly melted away during these early days. I remember being certain I would never let a dog sleep in a bed that I was in, however it took a few short weeks before she found her way to overcoming those objections also. As she’s aged, she can no longer run. However we’ve had a lot morning walks to get coffee, which provide much of the same opportunities to bond.

The past six months it has been sad to watch her age. There are times that she doesn’t even seem to be herself. However, having tried nearly all the anti-anxiety meds the vet suggested, we finally found that SAM-e gave her some since of peace. There are moments that she’ll act like a 3 year old puppy again, with energy and vigor. Though most of the time our lunch-time walks are limited to 30 minutes, where we make it 4 or 5 blocks.

The clear result of Kelty becoming a part of my life is nothing but positive.

I see the adoption of Kelty as a Black Swan event within my life’s narrative. Here’s a summary of the three characteristics of a Black Swan from Nassim Taleb:

I stop and summarize the triplet: rarity, extreme impact, and retrospective (though not prospective) predictability. A small number of Black Swans explain almost everything in our world, from the success of ideas and religions, to the dynamics of historical events, to elements of our own personal lives.”

I can rationalize the events of her adoption, piece together the storyline to make some sense of it. But it’s mostly a storyline that is artificial, created to give myself some context to share with others when they ask. The truth is that her introduction into my life is one of those random and wonderful events that happened.

I concluded my previous post with: “For the time being: live intentionally, yet remain aware and open to the randomness life provides”. That seems like a pretty excellent way to end this post also.

Counting on Serendipity

“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.