Jump

Preparation

Over the next couple of months, Patrick and I tossed around different ideas of The Big Problem that we aimed to solve in our future business.  In November 2012 on a trip with a few friends, Patrick waited in line at a restaurant far too long for his comfort and the idea was born: solve waiting with an app that shows wait times.

Up until this point I was a Windows guy.  In fact, I always used to chide my Mac friends, and then my conversion slowly began when I got my first iPhone; then an iPad; then an Apple TV.  Finally, the coup de grâce was the sudden realization that if I was going to become an app developer, I needed a MacBook.  Apple just happened to have a great Black Friday deal so I put out the fifteen hundred bucks and began using my spare time in the evenings and weekends to teach myself about app development.

The next nine months was a time of internal realization for me, as I began realizing each of my lasts at my job: my last Christmas party, my last time doing this or that, and so on.  However, I was thinking these thoughts only to myself, because I had not revealed my decision publicly and did not want to tip my hand too early.  Nonetheless, I was deeply-entrenched at the telecom company, so the path to departure was a long path of training people, delegating responsibilities, strategically handling various projects and, ultimately, leading the company to its independence from me.

I took my last vacation in June 2013 and when I returned, I began a countdown towards the day I gave notice to my boss, the company's owner.  It was very emotional for me, as I felt so much excitement over the future, depression over leaving my friends, and apprehension over leaving a paycheck behind and beginning something that promised nothing but the unexpected.  The day came, and I asked my boss for a few minutes.  I began to recall my initial promise of six-months and how it had become twelve years.  I was nervous.  I was shaking.  I was afraid of what he was thinking.  I was glad that I had rehearsed the speech numerous times to myself because I felt almost numb and detached from the moment in his office.

The next six weeks was difficult in all new ways.  I hated how the news broke, and I felt like I betrayed my friends.  I was in a race against the clock to make final preparations for my departure.  I was working sixty- to seventy-hour work weeks out of loyalty and commitment to leave the company in the best possible position without me, but I also felt like I needed to spend time getting ready for my future business.

My last day was Friday, August 30.  I walked out the doors that day at 5pm with no fanfare.  I received no gold watch for my twelve years and there was no party in my honor.  Shoot, I didn't even get a commemorative pen.  I just walked out the doors with my boxes of stuff from my office, packed up my car, and said my goodbyes to some of the closest friends I have ever had.  I took one long last look at my home of twelve years and in that moment, all of my adult life flooded my mind.  And then I drove away, medicating myself on a few Switchfoot songs.  I thought to myself, wallow in your emotions for only a short while David, for tomorrow there's no time for self-pity as your life's greatest challenge awaits.

My Background

Twelve Years of Telecom

Most of us will reach a point at our jobs where we become disheartened or lose interest in what we do.  Some of us will feel that sentiment numerous times throughout the course of our tenures, and for any number of reasons.  I began my career counting on it.  When I was hired at a telecom company at the age of twenty-two, I told the owner that I would commit for no more than six months because I wanted to start my own business, which at the time meant my own computer repair service company.

Ten years later, without ever truly committing myself to starting my own business, my job at the telecom company felt secure and prudent, and it felt like home.  Of course, through my tenure every several months I would feel the rise and fall of sentiments over my job but those feelings were often mitigated with the freedoms that I was given to explore new responsibilities at work and take the company to new heights.  I have a very strong competitive drive in me and I always felt like I needed someone or something to conquer.  The more I was given those freedoms, the more I conquered; the more I conquered, the longer I could suppress the feelings that I wanted to accomplish more in my career.

Beginning in 2010, we hit a stride as a team, and we saw unprecedented successes year over year.  However, it seemed that in the process, freedoms were restricted, trust was unjustly withdrawn and the status quo could no longer be challenged (something that I always thrived at).  I felt dejected and demoted.

The incredible irony during this time was that I was making more money than I probably ever would have imagined when I first started the job.  While it often felt like an obligated bribe just to keep me there, I couldn't deny that it was a successful strategy.  But I wanted more...more challenges, more opportunities, more adventures, more significance.  The money was nice and it provided security for my family but it felt like dirty money.  Why?  Why could I not just be happy with what I had, the amazing friends I worked with, the fun we enjoyed, the camaraderie?  Why could I not just be a "good employee", shutting up and doing what I was told?

Summer 2012

By the summer of 2012, I was completely burnt out.  Eleven years at my job and I now felt mistreated, misunderstood and like the token punching bag whenever the owners had a bad day.  What I didn't realize at the time was how my own paradigms and business mindsets had shifted dramatically the past couple of years.  As I achieved more successes at work, there was an evolution that occurred in my thinking.  Whereas fear and mistrust seemed to be settling in on ownership, determination and ambition was growing inside of me.  I could feel the inevitable creeping in on me but it was so difficult for me to wrap my head around the reality that I was working myself out of a job.  I began to send out warning flags to my closest friends at work but in a way it almost felt like more of a cry for attention than it was truly my intention to get out.  Was I really ready to leave?

As I began considering what other career options I had at the time (which probably were minimal), my longtime friend (and former neighbor) Patrick was bugging me to go into business together with him.  While the idea was appealing, realistically I felt like it would never happen.  I still felt too entrenched at my current job, it was my home.

One evening during this period of time, my wife Heather spoke some words over me that seemed to awaken my soul.  I'm sure if Heather knew then what she knows now, she might've spoken differently to me that night.  However, something in the words she spoke freed me to look beyond my current job, to not be afraid of the unknown, and to consider how I could take Patrick up on his crazy schemes to make me leave the telecom company.  The next day I texted Patrick and asked him if he still wanted to jump.