Over time I think we all make choices in our career that either pay off or don’t. Lately I’ve witnessed a few friends go through some bitterness about how things played out recently for them. I’ll be the first to line up in the bitterness line. Back in 2004 I sold my remaining shares in Apple Computer at $22 pre split to pay for my last year of college. That money now would be worth about 40x what I sold it for. Am I bitter, not particularly because it was a choice I made because in the long run I thought it would pay off.

I always ask myself a few questions when deciding to work at a company. Beyond salary and benefits will the team make me better? Is there something to learn from the people who run the company? My thinking here is if you are going to give up your time and opportunities to work elsewhere you absolutely should feel the team you will work with will make you better.

I look back at a few of these decisions often.

1. Working at Apture. The minute I met Tristan I said to myself this guy is going to make me better. He is going to push me to better examine interfaces and think that much more about building a better product. It turns out beyond that I learned a whole heck of a lot about the psychology of users and how you should make them “feel” while using your product.

2. Working with Steve Susko, Doug Moony, Jerry McDougal and Corey Fugman. When I interned on the Apple Merchandising team these guys really taught me how to negotiate and stand your ground when it comes to value. They turned the Apple Retail Stores into a high value/high margin machine. When you walk into a store and see particular items featured you’ll be damn sure most of them are paid for. Most importantly they taught me to have standards when it comes to what you’ll feature. I remember being in Jerry’s office when he asked me what I thought of a specific pair of headphones. Over the next five minutes he destroyed my opinion telling me the packaging is terrible, they look atrocious and the packaging would never let them stock them within a store. When you hear things like this you really start to realize how much thought goes into their stores and that its not all about the money.

I could’ve spent my Sundays watching football, but instead lived in excel building planograms for Apple’s Retail Stores because I knew in the end they would make me better.

In closing I always tell people worry less about the $. Think more about the who you’ll work with and the what you’ll learn. The $ will become a bi-product.

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