10/07/2013 02:12 pm ET Updated Dec 07, 2013

Think or Act? A Deep Thinker's Dilemma

I'm a master at complexity. I love to over think, ponder and explore. This has served me well -- especially in business. I think through things. I find new options. I identify the optimal solution.

But at what point does my ability to think deeply hinder my results?

It depends. I've learned there's a fine line, and it moves based on the situation. Here's what I've figured out in my 37 years of being a deep thinker.

Always think deeply, if:

  • The penalty of failure is severe. When I started my first business, it was a big cash outlay and a notable sum of debt. Success wasn't assured, but meticulous planning and thinking through every detail served me well. (And don't let this prevent you from taking calculated risks... you have to in life!)
  • Consideration affects your mental or physical health. This includes losing sleep or a change in your mood. When this happens, your mind or body is trying to tell you something is off. This is a clue you need to think it through. For me this happens when I haven't truly acknowledged the degree of risk is high for me.
  • You're suspicious. This includes feeling like it's too good to be true, I must be missing something or why would someone behave that way? I do my best to surround myself with people I trust and admire. I also try to be in situations that promote fairness. Of course, I can't always do that and I have to listen to my gut. Interpret the people and situation around you. Slow down and be a deep thinker if something's not right.

Take action or move on, if:

  • Your matter is trivial. Some things are just not worth it. I've been known to stand in my closet tirelessly debating in my head which tie to wear on an interview. The truth is I just need a conservative, professional tie and I don't need to psychoanalyze how red is could be seen as more powerful but aggressive and blue could be seen as calm yet passive. Just pick the tie.
  • You're reinventing the wheel. In business, if your team has decided don't get left behind trying to make something good enough brilliant. In a past life, my team completed a targeting project and I was determined to make it perfect. I wasted hours agonizing and developing market-specific targets that never saw the light of day.
Evaluate the situation to make a decision, if:
  • The risk is high. When it's a risky choice you must look at the downside. If you fail, can you tolerate the worst case scenario? If so, go for it. If you can't, think a little more but not at the risk of missing a deadline. I made the choice twice in my life to pick up and move. Once I moved having a no job and knowing only one other person. The other time I moved with a job but knowing no one. In both situations, I felt that the worst possible case was that I would have to move back. In both situations, I grew substantially as a person.
  • There's ambiguity. It's okay to be comfortable with the unknown or not perfect. Too much ambiguity is a cause for thinking. But ambiguity on small matters will hinder you.

Do you unnecessarily complicate things? Do you reinvent the wheel? Are you a deep thinker? Cool, join the club. Let me know what other guidelines you have.

For more by Ryan McKeever, click here.

For more on emotional wellness, click here.

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