Three Things I Wish I Knew Before Starting an Agency

Planning

I was initially introduced to Dreyfus model of skill acquisition by Merlin Mann, one of my favorite go-to’s for anything around productivity and the world of work. This concept changed the way I thought about problems and about expertise. The model basically describes a stage in the learning cycle where we are “advanced beginners”, which follows the novice stage. The advanced beginner stage is best described as a period where we have a lack of situational awareness.
This means that you’ve built enough expertise to the point that you believe you’re an expert, without the true experience to know where your deficiencies lie. This period is incredibly dangerous because it causes people to quit jobs, take risks, and overall do things that they simply shouldn’t because of a false arrogance about their true skills in whatever they call a career.
As with anything, I, in many stages of my career and life, reached this stage. I particularly reached this stage as it comes to three aspects of building a company and overall building a life, with strong associations to starting an agency that others might empathize with (or be glad to know before it happens).
1. Stock Trading is Not a Path Best Occupied by the (Tech) Obsessed
When starting an agency (and before starting an agency), I finally started to learn what having a few bucks in my pocket felt like. And of course, once you start making a few bucks, what you want more than a few bucks is a few more bucks. So I started investing. I invested in stocks and started following a dude named Jim Cramer, who is a generally well regarded stock expert in the space, mostly because of his show Mad Money.

Believe it or not, that guy pictured above generally knows what he’s talking about. He helped me start making more money. I thought I was a genius. Then early 2014 hit, and the shit hit the fan.

The thing is, with the stock market, everyone thinks they’re a genius when things are going well. But in a downturn, the experts start to show their face – and so do the advanced beginners. Early this year, I realized that I was not ready to be trading individual stocks, and it ended up costing me a significant amount of money until I realized exactly why that was.
The reason I lost a lot of money aligned pretty closely with my job as an agency owner:

I was obsessed with my company, and it was the most prominent thing on my mind.
I did not have time to properly study the stocks I was trading.
My job involved sitting in front of a computer all day, and I didn’t have the willpower to not take action on daily stock moves.

Jim Cramer recommends spending an hour each week studying the stocks that you trade, and also recommends having a portfolio of at least five stocks from different sectors. I did not realistically have time to spend five hours a week studying stocks, especially with a full-time girlfriend, and even if I did, that would have been time better spent building Siege. I had two obsessions, Siege Media and my girlfriend (now fiancé) – and I didn’t have time for a third.
And to add to the problem, my job involved sitting in front of a computer all day. Stock swings and downturns meant my stress had an outlet to sell low and buy high, and do it repeatedly. I could see running some company with a ton of travel or a night shift and perhaps not falling as heavily for strong swings, but when I can sit three seconds away from hitting sell, and a stock is down 5%, it’s really hard to overcome the instinct of selling. And to add to the problems, because I worked in tech I invested in tech – meaning that the swings were more aggressive and brutal than in any other industry.
Of course, lots of these problems could have been solved by getting over my instinct to day trade, or otherwise learning from my initial mistakes (that all will experience to some degree). However, after countless stressful days immediately triggered the moment I read the stock ticker at 6:30AM, and several other times reading how difficult it was to beat the market in general, I gave up – and not a moment too soon.
From the period of 2-1-14 to 5-31-14, my stock positions lost 11.39% of their value, relative to a 8.73% gain for the S

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