God and I had a talk about being rich on Hanson’s Point.

Last weekend my friend Tyson and I made our way to the Red River Gorge for our first camping trip of the year. I shared a little piece of that story last week in my post about Randomness. The trip was excellent, which has motivated us to spend the week thinking about how to get more camping and hiking in this year.

There was one experience I had that stands out above all the others. I shared that moment on Instagram. I was sitting on Hanson’s point taking in the view. In the moment, I was inspired to get out my Crossroads app and read the daily scripture.

For the majory of life, turning to God and scripture was a place of refuge when thinking through difficult decisions. That changed fairly significantly when I was around 33 years old. Maybe some day I will better understand that change and be comfortable writing about why it happened. At the moment, I have not been able to fully process it.

Despite this fact, I made the decision last fall to attend Crossroads. I started attending with a mindset in search of answers. I have sought guidance from various philosophers, psychologists, neuroscientists, buddhist teachings and self-help books. The realization was that I also wanted to find others who were willing to be open minded and in the process of seeking answers to life’s bigger questions. Crossroads has offered a non-judgmental place to do this.

That is a long story to explain why I had the Crossroads app on my phone. The view from Hanson’s point inspired me to read the scripture of the day. The reading was Proverbs 13.

The words that really stood out to me were from verses 7 and 8.

“One person pretends to be rich, yet has nothing;
another pretends to be poor, yet has great wealth.

8 A person’s riches may ransom their life,
but the poor cannot respond to threatening rebukes.”

This message really grinds at my soul in a couple different ways. If you have read my writings over the past couple years, it may not be surprising that it relates to work and dating.

In the startup world, there is a somewhat unhealty relationship with “funds raised”. While I am not exposed to a lot of startup communities around the US, I have a fairly high exposure to the one in Lexington, Kentucky.

The topic of how to start a business and raising money was also a topic that Thomas and I aligned on in our early days, which ultimately made me comfortable partnering with him.

The position that we have taken is that raising money should be done in very specific situations. The act of ‘closing a round’ should not been seen as a successful outcome itself, but rather a tool that is being used to move forward towards a more admirable goal.

I think Gary Vee said it best when he shared a lesson from his dad that said, ‘When you borrow money, it’s the worst day of your life’.

When I see people celebrating raising funds, I am now going to think about Proverbs 13:7. Celebrating this event, in my mind, is a sign of someone who has nothing, yet pretends to be rich. This may not always be the case, as there are legitimate times for raising capital. However, I rarely have conversations with founders in that position.

In terms of dating, I will simply acknowledge that the desire to put out a perception of having more wealth than exists is incredibly high. The ease to access capital for consumer purchases is a little unnerving for me at times. This access has been tempting in several situations the past two years, as I’ve worked to become ‘fully free’.

My personal definition of being free is:

  • zero financial obligations to anyone else
  • ability to work on projects that I’m excited to work on (always thinking about impact and legacy)
  • have control over my time (no requirements of a 9 to 5)

I believe I am 80% of the way to this goal. I am still working to get to where I can be very choosy on the projects I decide to work on. I know deep in my gut, that if I succumbed to the desires to access cheap money and “pretend to be rich”, I’d push this progress down to nearly zero.

As verse 8 says:

“A person’s riches may ransom their life”.

My current interpretation of the verse is that if riches is what you value, then there are many things in life you say you value, but will end up forfeiting in favor of those “riches”. I am probably taking that verse completely out of context?

This is where the lyrics from the song Suit and Jacket from Judah and the Lion comes in:

“Cause everybody I know, everybody I know Is growing old,
is growing old too quickly
And I don’t wanna go
So how am I supposed to slow it down so I can figure out who I am?
And I ain’t trading my dreams for no 401k
And I ain’t giving this fire for a cold, cold heart
So don’t say I’m getting colder
Cause I’ll say it when I do”

As I turn 40 this year, I have spent a lot of time thinking about the expectations I have had for my life. I expect a lot out of myself. When I moved to Kentucky, at 23 years old, I had ideas of what 30, 35 and 40 would look like.

The two lines from the song that I hear myself thinking about daily are:

“So how am I supposed to slow it down so I can figure out who I am?
And I ain’t trading my dreams for no 401k “

If my definition of having freedom is having the ability to pursue projects and work that I want to be a part of my legacy and that creates impact, then I can look back on the past 17 years with a great sense of accomplishment. I have been fortunate to have had different opportunities to direct energy into my personal mission statements. This has been true in different settings with various co-workers, multiple business partners and individually.

However, it comes at the “expesnse” of not having 401ks, pensions, guaranteed paychecks or at times health insurance. The instability of this lifestyle is one that any entreprenuer understands, but many people find undesirable or even foolish.

The ending:

There is no doubt I spend my days chasing “success”. That success is in terms of personal impact, but also financial gain.

The world in which we live makes money a clear way of keeping score, making it difficult to not be tied to it in some way.

This entire post can be distilled down into this question, which I ask myself some version of often:

“How can I be successful and create impact, all the while remain free from getting caught up in easy attempts at appearing ‘rich’?”

When I cross check that desire with the expectations I had for myself, I get discouraged.

A friend told me this week,

“If you are going to trust God for the process, then you also have to trust him on the outcome.”

To be completely real, I am not at a place I trust God with the process. I am definitely not ready to trust him for the outcomes.

What I do know is that we started a conversation on Hanson’ Point last Saturday. He apparently had a lot to say. At the moment, I am trying to be a good listener. We will see where things go from here.

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Lessons about routine and randomness, that I learned this weekend.

Friday night, the start.

We had a plan. Each of us had expectations for the camping trip. It was not a detailed plan. It included a trail that had been utilized on a previous camping trip. The path was less of a concern than the final setup at the destination. Then we turned left off of the highway to drive down Tunnel Ridge Road, when the plan ended. The road was closed. We improvised and went to Koomer Ridge Campground and headed out on the trails from there. We soon found ourselves without daylight. I was missing my headlamp. There were no camping locations to be found.

Saturday night, the start.

There were loose plans. The main goals being time spent hanging out, eating and drinking. The first two spots were pre-determined, but even the best constructed plans can be derailed with rain and lost keys.

How to embrace randomness.

I have spent a lot of time contemplating the value and benefit of embracing randomness over the past eighteen months. The main catalyst for this rumination is that I randomly met Thomas Cothran at Awesome Inc in August of 2016. At the time, he was a fellow student who became the exemplar of what being a student really meant. Since that time we have been working hard to accomplish fun and interesting things together. The short list of challenges we are taking on include:

  • Building a software consultancy business, focused on healthcare and law (Not simple markets to penetrate with innovation.)
  • Build a sports technology consultancy.
  • Partner with other like minded individuals to spin out products focused on the law, healthcare and sports industries.
  • Mentor startup founders who need product and technical advising.

All of these efforts are very focused. The time, money and energy we put into each of these four areas are done with efficiency, productivity and impact on the top of our mind. We have spent a fair amount of cognitive power over these eighteen months establishing, refining and iterating on the processes we use to do our work.

The reason I am highlighting the efforts we put forth is to help explain the value that pure randomness has upon the outcomes we have observed. I would argue that even with the rigorous approach we have to our work, a good portion of our success can be attributed to luck. If the word “luck” is hard for people to accept, then I’d suggest, “random chance”.

Are we all fooled by randomness.

I will circle back to the intersection of random chance and effort in a moment. First, let me acknowledge Nassim Taleb’s book “Fooled by Randomness”. I started listening to this book, for the third time, as I drove up I75 this afternoon. This book has always impressed on me the value of consistently evaluating your outcomes and being critical of your assessments. This is especially true if you start to attribute successes with specific actions.

It is easy to look back and find something to attribute your success to. The hours you spent doing sales calls. The years you spent in college developing an expertise. The networks you have made throughout your career. The decisions you made in your product specifications. If you are like me and tend to overly analyze the details, you are likely to also (like me) tie all the outcomes to those efforts.

This is when we become fooled by randomness. Or, I will simply say, this is where I am fooled by randomness.

As I have become more comfortable knowing that my actions are not as powerful as I thought they were and luck is just as responsible for my successes, I have become more accepting that I can not control the outcome of everything. This is a lesson that I wished I learned twenty years ago.

Armed with this mindset, I have the ability to embrace random events with a sense of excitement and adventure. These same events would have caused me great anxiety and frustration in the past.

Why routine is critical for me to happily accept randomness.

The words routine and randomness seem paradoxical. However, I find having well defined routines is essential for my ability to accept random chance with an open mind. Here’s a simple explanation why:

I need the basic structures of my life to be maintained with the least amount of congnitive load. This mental efficiency provides the space necessary for creativity, along with the extra mental and emotional costs associated with following random paths.

When I fail to cover the basics via routines, I spend too much brain power just getting through the day. The basics become exhausting, which means that randomness generates:

  • increased stress
  • tendency towards anger
  • decreased happiness
  • lack of empathy
  • prevalence of depressive moods
  • high anxiety
  •  …

What are the basics I have offloaded to routine

To provide a clear explanation of what I mean by this, here is a list. These have all been an evolving practice since around 2009. Some of these are a philosphical approach to life, others are environmental choices I have worked to establish.

  • The place I leave my running shoes.
  • Having a room dedicated to yoga, stretching and meditation.
  • What I eat for breakfast, every single day.
  • Where I place my keys, wallet and sun glasses when I walk in the door.
  • What day of the week I do laundry.
  • When I answer email during the week.
  • My choice for type and location of housing.
  • Decision to not use debt as a financial instrument for anything. (clears up decisions around monetary routines )
  • What phone numbers I answer (short answer: none as a general rule)
  • What routes I run for daily runs.
  • The brand of toothpaste I purchase.

This is a short list of items, as there are many routines that I have established that are subconscious operations today. I believe the list helps clarify the concept.

Why work hard, if randomness is so important.

The best answer I have for this is the Stoic philospher Seneca’s quote:

“Luck Is What Happens When Preparation Meets Opportunity”

While it’s not a great analogy, I equate being efficient and productive to buying a lottery ticket. The effort you put out is your currency to enter the Powerball. With that effort, you still are subject to the randomness of the balls, but without it, you are simply watching the world pass you by.

Friday Night, the end.

It was dark and we were both somewhat concerned about finding a place to camp for the night. (Even if we were not vocal about those concerns.) We had hit the trail we were looking for, hoping it was a better option. At the moment, it was not producing anything of use. Then we heard some small voices coming from behind. I turned to see a couple headlamps and a dog with a light coming towards us.

Those hikers were able to lead the way to a new trail, a new camping location and one of the best views in the Red River Gorge I had yet to see. Was it luck? I would say it was more than luck that night.

Saturday Night, then end.

When randomness strikes and it leads to a positive outcome, it can be simple to be easy-going. What happens when situations arise that are not fun? Like losing your car keys?

I know with a mindset that didn’t accept randomness. The one that had to control everything. The one that needed plans to work out. That person would have folded under the stress and become a negative and angry person.

In moments such as this, the number of starts and stops are so frequent that it doesn’t feel like randomness alone. It felt like a tilt-a-whirl at the county fair. There is hope, then you are jerked back from where you came. There is excitement, that is stolen. In the end, I was able to evaluate how I carried myself throughout it all. I hope it was with grace and kindness? I was also able to spend more time with someone, who I wanted to get to know better. This random event allowed me to see how she responded to a much more difficult reality than I faced. While not an idealistic situation, it provided better insight than had the night went exactly as planned.

The lesson in a couple sentences

Life can be difficult if you need complete control and for everything to go according to plan. Therefore, develop routines to put the basics on autopilot and remain open to the random blessings you will find along the way.