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Posted On 05.27.10

I was talking with a really close guy friend this morning about overcoming personal obstacles to achieve success. He calls it “risk investment” and more specifically that you invest in your future success by taking a “risk” now. As an example, he used me leaving my comfortable and stable job in San Francisco, selling everything I owned and moving to NY to seek out and pursue my true passions. His also made the point that the younger you are, the more risk you have to invest. I totally agree.

He then went on to explain that his problem lies in not knowing what his true passion is and more specifically, which is worth taking the risk investment. I think his problem is more than not knowing, it’s not doing anything about it. (As I also explained to him.)

Here’s why: we’ll never find out which is worth the investment by sitting around and thinking through every potential possibility and outcome. We learn to know by doing and finding out, by experiencing the answer. No amount of thinking in San Francisco about what my passions are and which was worth investing in would have provided me the insight and comfort to get to where I am today. You just have to go do and figure out.

He then asked how I assess and figure out which is right. Good question.

Since getting to New York, I’ve been actively exploring a lot of different opportunities. I assess each in a few ways:

(1) what the company does/mission/vision: what do they do and how do they do it. do I have alignment?
(2) my role: does this complement my skill-set, enhance my experience, can I effectively help the company reach their business objectives?
(3) internal structure: how do they communicate, lead, manage and get things done? what can I optimize or improve? what can I not?
(4) how I’m compensated: can I pay for the quality of life I want in NY? can I create revenue streams? is equity an option?
(5) trajectory: where is this company going? can I go somewhere with it?
(6) concerns: do I have any?
(7) inner voice: every day I ask myself, how does the opportunity make me feel? what is my gut instinct? not only initially (because there’s always early excitement) but also over time.

Analyzing each opportunity in this way allows me to objectively assess both where the company is going, whether or not I can effectively insert myself and how it also makes me feel. All equally important to doing work you love, I think.

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Comments

05.27.10

Your thought process is great. I make lots of lists when I want to make a decision, but I never ever NOT make the decision. Like you said, if you analyze until the cows come home, but never do something, it's not going to matter. Things won't change.

05.27.10

Number 7 outweighs all the other points for me at this point in my life, but I love the way you outlined your criteria for accessing potential opportunities. Having a clear vision is important if you truly want to be successful doing something that you love.

I made a bad career decision in the past for the wrong reason (a big salary increase), but I quickly realized that I would never be happy doing something I am not truly passionate about. Those temptations come up and sound great at first, but it is always good to consider them carefully before making a career move for the wrong reasons.

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