What Does Success Look Like To Me?

What does success look like to me? Obviously to have a shit ton of money, but more specifically what does it look like? Does it look like a CEO position of a major corporation? With hundreds of employees? Fueling your passion and leading your company to the day for that successful IPO?

For a long time, this is what I dreamed about, this is what my answer was to that important question. My hero was Steve Jobs, and I wanted to be exactly like him. I read his biography by Walter Isaacson, and was amazed by all his triumphs. His obsession with creating great products was so inspiring. His intense focus and tenacity, the ability to strip away what didn’t matter, and his shear will that fueled his return to Apple, it was legendary stuff. And I loved watching his keynotes. They were absolutely mesmerizing. He is what success looked like to me.

Over the years my vision of what success looked like started to change. As I trace it back, there were several key things that happened that kickstarted this change.

I reread Steve Job’s biography with a different interpretation
I was hired at a startup company as employee #1 and worked there for 4 years
I read Tim Ferriss’ 4-Hour Workweek for the first time

Let’s look at these one by one.

When I reread Steve Job’s biography I was engaged with my wife, Lacey. A little backstory here, my wife and I have known each other for a very long time, and I pursued her for over 3 years before actually going on our first official date. She was always dating someone, or I was involved with someone, the timing never seemed to match up for a long time. Persistence eventually became my ally, and the rest is history. Ok backstory finished!

So I reread Steve Job’s Biography. What struck me this time around was how horrible he had dismissed his high school sweetheart, Chrisann, and their child Lisa. Why did he do that? Was it because he felt like they were in the way of him being successful? An obligation he did not want?That’s crazy right? You don’t need to alienate the ones you love to build a successful company… right?

That strong focus that I admired so much about Jobs was now shown in a different light. Focus, by definition, means ignoring other things. This same pattern of successful people alienating loved ones showed up in people like Elon Musk, Jack Welch, Craig Mccaw, all successful CEO divorcees. I realize that these are just a few examples among many successful CEO’s, many of whom have great relationships, but it did change my view a bit. Steve Jobs became a cautionary tale. I did not pursue the love of my life for over 3 years just to throw it away. Or perhaps even more realistically, I wasn’t going to accept being anything less than the best husband I could possibly be for her. I am fantastic at focusing, which also means I am great at ignoring things, and Lacey is not someone I wanted to be great at ignoring.

I started as a software engineer at a startup company called RIGPA in early 2012. I was employee #1. It was just me, my boss, and the VC that was funding us. I loved it. I was learning so much about web development, sales, marketing, basically everything about how to run a business. My boss was my idol, he was also an engineer. I remember working 12+ hours crunching out code with him for several months, week days and weekends, and I loved it. I slept, ate, and breathed that startup.

Among other things, there was two takeaways from my 4 years there. One of the two, I learned very early on: At this level of intensity, balance was hard to come by. When I was crushing it at work, I felt my marriage was suffering. When I was focusing on my marriage, I felt my performance at work could be better.

The second takeaway didn’t appear until my time at the company was coming to an end. I had told my boss early on that I was leaving the company, I game him a year’s notice ( crazy long right? ). Before I left, he gave me some parting advice. This is what he told me.

“Don’t take money if you can help it.” Strange advice indeed. Here was a man, the CEO of his own company with several employees, who was able to get to this point with help from funding… telling me not to follow in his footsteps. What I failed to see in the four years of working under him was this: He may have been the CEO of the company, but he was not the boss. That title was for the VC himself. My boss couldn’t always do what he thought was best for company because our VC thought different. How frustrating that must have been. It’s like getting told by a complete stranger that you are raising your child incorrectly, and feeling obligated to do it their way.

These two takeaways left an impression.

During my 3rd year at RIGPA, I came upon a book by Tim Ferriss called The 4-Hour Workweek. This was a game changer. Up until then, there wasn’t many different variations of what success looked like to me other than the CEO of a huge company. Tim Ferriss changed all that. Here was a guy who had the lifestyle of a successful CEO, without the chains of obligation to a VC, or employees, or shareholders. He designed his life in such a way where he could work when he wanted to, where he wanted to, all the while enjoying these long vacations he called “mini-retirements”.

He designed it that way because he did start out as a CEO of his own company, working 80+ hours, feeling obligated to work otherwise the business wouldn’t go on, having relationship torn because of the grueling hours that was required of him. He was the cautionary tale… and became the Fairy Tale.

Sometimes you don’t see any other way until you are shown. I was shown. Ferriss became the epitome of what success looked like to me.

The idea of truly being my own boss, working on what I want to work on, when I want to ( I sleep in most days now, but I work better at night anyways ), and where I want to ( poolside is becoming my new favorite workspace ), not feeling the pressure or obligation from bosses or VC’s, to have the time to work on my relationship with my wife, to be able to spend time with her and not feel guilty for not working, having the freedom to truly choose my day and do what I want to with it…

This is what success looks like to me now.

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