Dating “Out Of Your League”

“She’s a model dude. I know she is out of my league, but damn, I would love this girl”

It is a story heard again and again, with me often times the one lamenting the thought. It typically does not end well. This time, it is the situation of a good friend, told over a marginally-intense game of bocce ball.

My friend I speak of has a hell of a lot going for him.  At the young age of 26, he is a director at a company you have heard of, with a team of men hired by him to do the work he thinks is important. These are smart, educated men all his superior in age. He’s fit and has a sense of style. He is the guy women dream of bringing home to mom and dad. Yet here, he had a sudden loss of bravado. In the name of making both his AND this model’s dreams come true, I had something to say…

Think of the life of an entrepreneur. When it’s ones own ship to sail, he/she ponders hard the big risks. Though decisions have to be made, the type of decisions kill the whole venture if wrong. For these fledgling businesses to blossom, core philosophies are developed to guide these thousands of decisions to be made. A company’s identity is developed, and a culture to it arises. Think Steve Jobs getting apple to Think Different as an obvious example of such

Where things go wrong is, once successful, the entrepreneurs who start the business suddenly have something to lose. The lightness and freedom of being an unknown suddenly fades.Worried about losing a status earned over years of nose to the grindstone work,  the previous chutzpah harnessed to take the necessary risks with uncertain results is undermined.  Becoming too precious with their success, puts their efforts into maintaining the status quo. Refusing to adapt any further, they atrophy.  Soon they those philosophy and behaviors that got them to the mountaintop in the first plays. The company then dies a slow, meandering death.

It is fear of losing it all that did these businesses in.  The people who worked so hard to build something real worry that doing anything  drastic may make it all disappear.  Suddenly those behaviors of taking necessary risks to create become safe decisions aiming not to lose. The “Not lose” approach becomes the prevailing wisdom, the company plateaus, then decline no longer armed with the creative driver for growth

Let us go back to the 2000’s. Blockbuster was THE movie rental giant. They were unmovable in their position in society’s go to for a night in with ice cream. Netflix took the scene as a small boutique agency that would mail you DVDs. Netflix was an interesting something new, but inevitably an afterthought to the blue rental giant. Times began to change however and as the internet modems became faster, Blockbuster remained stagnant. Netflix didn’t, building such an impressive streaming library that “Netflix and Chill” is now a cultural code word for “Let’s fuck all night”

Netflix didn’t stop there however. Keeping true to the forward thinking that cemented them as a force to be reckoned, they committed to the ever growing phenomenon of binge watching by commissioning smart people to create original television series to all be released in one big dump, something never done before. I assure you that small mail you a dvd company of the early 00’s considered the winning an Emmy drastically out of the realm of possibility, out of their league if you will. When the opportunity arose though, they didn’t flinch. Staying true to the spirit that gave them the opportunity to compete in originally programming, they put big money into the develop such series.

After a particularly fine Bocce shot that would make many any old italian man proud, I finish off my rant telling my friend to be Netflix, and to play the game that got him the date with the model in the first place. To suddenly play it safe and conservative now, as if he had something to lose, would doom him just like blockbuster. I told him to continue to value his time when it came to dating this girl, and do not suddenly become more accommodating to her wishes. Don’t concede that “She is the one” and start showing her all the nice things he could provide her. Keep to the attitude of not knowing whether she was the girl he wanted. It had only been 2 dates, and impossible amount of time to really know another human being. We do not know yet whether she is worthy of his full attention.

When we perceive ourselves operating “out of our league”, we get conservative. We worry we will blow the opportunity. The truth is, we very well might. There is uncertainty in all things new, especially in a new relationship. I say embrace the risk, and keep true the individual that got you the opportunity in the first place.


Nerding Out: Improve Your Dating Life With Metrics

I recently acquired a fancy GPS running watch –  A Fitbit Surge. It includes a heart rate monitor and a GPS. It tells me how fast I’m running and even buzzes every mile informing my mileage time. When my run is over, it conveniently exports into my computer where I can look at my pace and heart rate per mile. Tomorrow I will do the same, and see if my kale smoothie breakfast affects the numbers. Soon I’ll have a mountain of data, and I can experiment further. Will a pre workout supplement improve my times? Maybe I’m better running in the morning than in the evenings. I plan to start messing around with Heart Rate training to build my endurance. I’ve gotten pretty far with the lace-up the shoes and go model of running. I want to improve though, and do so efficiently. By monitoring the statistics, and can confidently work towards hitting target marathon time come November. Knowledge is power!!!

What does this have to do with dating? Well, the metrics part of my training I borrowed from my dating life. I experienced the biggest improvement when I kept track of my personal stats. (Math nerds, this post is for you.)

Like with my distances ran, I would keep track of how many women I approached in a given month. The goal being to approach at least 30 women with intent.  By intent, I mean someone I actually wanted to go on a date with. This gave me a baseline, and was a measure completely in my control. Next, I put my engineering degree to use. (Finally!) Of those 30 approaches, I tracked the outcomes. What does a positive interaction with a women look like? Well, a phone number, a make-out, a date, doing the hanky panky, or simply a nice long conversation(greater than 5 minutes). Anything really that looking back can be measured works.

There were several benefits to this. First, I was kept accountable to take action 30 times month. Once rolling, I would well surpass my goal, never coming up short. My clients regularly surpass this number in a single day during a one-on-one coaching session, so one month is completely reasonable. I found people to keep me accountable to this as well, and made my efforts known outside myself in some form. A good buddy with the same goal could do this for you. The point of all this is accountability, which is essential development of any new skill.

Suddenly, once I hit 30, I have numbers that gave me an overview of how the month went. The first month being a baseline, I now could see improvement at a glance. Each subsequent month I would work on one aspect of myself, and I could measure the improvement in my dating life. If something didn’t work I dropped it. It became a self-experiment. Did those new boots and fancy leather jacket help? Perhaps a mustached would be good for me (For all of you curious out there yes. Yes! It was.) The bottom line to all of this was I saw the improvement, and could monitor what worked and what didn’t
The beauty of metrics such as these is that they eliminate the deadliest sin to one’s psyche, comparing yourself to others. I made the process all about me. I celebrated my wins, meditated upon my losses, and chugged away until one day all my goals had been met. You should do the same.