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39: New Year’s Angst Anyone?

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I don’t know about you, but New Year’s used to be a lot more fun ten or twenty years ago.

It was the biggest party of the year, right? Well, maybe Halloween was—depends on the year I guess.

The point is that when I was in my twenties I was not cursed with the need to reflect over time.

After all, when you’re twenty years old there isn’t much to reflect on—you are in the process of creating those memories in the first place.

Now, in my forties, every birthday and every New Year seem to be getting heavier.

Every year that passes, I ask myself more and more probing questions about my life—did I make the right choices? Am I on the right trajectory? What is the meaning of my life?

I can be pretty tough on myself. How about you?

Well, being reflective isn’t always fun but it is worth doing as a sort of a checks and balances on yourself.

Here is one exercise that I do yearly that I’d like to share with you. Hopefully you will find it useful.

Identify where you want to be in life. Be careful with this one. You have to keep asking yourself “why?” over and over again to get to get to the truth. For example, “I want to be rich” should be followed by “why?”. What you really want is often not the first thing you say but rather the product of asking yourself why several times to get to the root of what it is that you REALLY want.

Identify where you currently are in life. Ie… “I am a 44 year old surgeon working for a hospital who works 50 hours per week and makes $400K per year. I have three children under eight and a house in Chicago.” You get the idea I’m sure—the more detail the better.

See if you can draw a line between where you currently are and where you want to be in life. Do you see a clear trajectory there?

If so, congratulations! You are on the right track. Keep doing what you’re doing.

If not, try to figure out why there is not a clear path between where you are and where you want to be.

For example, maybe your dream is to own a professional football franchise someday. If you are a surgeon making $400k per year working for a hospital, you are making a nice living but you’re not ever going to be in a position to buy a professional football franchise or even be a minority owner in one.

If there is not a clear path to get from where you are to where you want to be, then you have to figure out where the problem is.

The good news is that there are really only 2 choices here.

Maybe you have misidentified where you want to be.

If that’s the case, go back to number one and start asking yourself “why?” again. Hopefully that will fix the problem.

If not, you might have a bigger problem on your hands and a harder one to admit. If your life today gives you zero possibility of getting to where you dream of being, you might have to change your starting point all together.

Ok—I know you might be reading this thinking—“No way, Buck. I’m too old. It’s too late, etc.” Listen, I get it.

Just remember a few things:

Most people over-estimate what they can accomplish in one year but grossly underestimate what they can do in ten (I think Bill Gates said that). Where were you ten years ago? Would it be impossible to push the reset button? Why?

As far as I know, you’ve only got one life to live.

Most of the limitations we believe we have are self-imposed. At 44 years old, I honestly believe that if I truly wanted, I could still do just about anything I want (except be a professional athlete). I bet if you really thought about it, you would say the same about yourself.

Anyway, this line of thinking has helped me a great deal and I think it’s my perspective as a business owner that has made me view my life this way.

Business owners often talk about the notion of “working on your business” rather than “working in your business”.

That is–It is critical to a business for the owner to step out of operations and look in with an objective eye to see whether the business is headed in the right direction.

Working on your own life should be no different, right?

Happy New Year!