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Deconstructing The Value Of Goals And Plans With Utter Delight

I am an obsessive planner.  Andrew tells me that’s the understatement of the century.

…obsessive planning has this affect.

I always have goals or plans.  Whether it’s to do 500 jumps in a row (took less than 2 weeks), finish my first book by 30, climb certain mountains or save x amount in a year.  A lot of times I track and map.  i.e. I am currently on day 40 into a goal that started on day 90.

There are a few areas I fixate on where my head gets immersed and my mind gets racing:

  • Writing
  • Travel
  • Hiking
  • Exercise
  • Gardening
  • Business
  • Literature
  • Money
  • Cooking/baking

All of the above have their place in my current situation. Many flux and some equal constant fixation.  I think of these themes and codes often.

The Flywheel

I was at a meeting the other day with some therapists.  They were talking about the flywheel from a Jim Collins book.  I’ve never read Jim Collins, but knew of him and Good to Great.  (Clay and Andrew had been listening to the audiobook on their fly fishing trips.) goodtogreatflywheel I really liked the flywheel concept. The idea that you just have to put yourself in motion.  Get going and then breakthrough comes when you’re moving in the right direction.  Eventually…it comes.  I related to it. These therapists used it with parents and failure to launch young adults to explain a concept.  But, as Jim Collins demonstrates, the concept also clearly works beyond the therapeutic realm.


In my own life I constantly challenge the idea that a (premeditated) slip up is okay.  I know the power of momentum.  Sure, you cannot control everything.  But you can control… what you can control.  And you know when you are making excuses (too tired, too preoccupied, etc, etc).

No B.S. Time Management for Entrepreneurs

I am reading this book by Dan Kennedy for work.  It’s all about time management.  He talks about how you should religiously plan your day and stick to your timeline.  He plans checking email, responding to calls, wake up, sleep and relaxation.

To some readers, that probably sounds blasé and the opposite of living.  But the point of planning isn’t to be boring and predictable. It’s to make sure your day is full and driven.

Planning your next day the night before actually gives you momentum and prepares you better in a shorter period of time than sifting through the muck in the day time and avoiding as much as possible as long as possible.  Having an outline gives you clarity and focus, which isn’t so much being controlled as it is being in control.

The Why To Planning

When I ask myself why I obsess about goals and planning the reason comes down to me getting more out of life.  If I don’t, I may do some cool things here and there, but I do not get my best or fullest week/month/year.

Flaubert said, “Anticipation is the purest form of pleasure.”

Looking forward always makes me appreciate forward, when it comes. Doing what I set out to do is creating the life I want/stepping into my own shoes everyday/imagining who I want to be and being that person.

Aligning Actions with Goals and Values

Sometimes we are not who we want to be and we are afraid to face that reality.  Definition also becomes crippling when we define ourselves based on where we are instead of where we are capable.  It’s hard for me to stomach the disconnect between actions and values, especially in regard to its affect on my sense of personal empowerment and relationship with myself.

The disconnect between actions and values often happens casually.  Sometimes the disconnect is not recognized, sometimes it’s avoided and sometimes the inconsistencies are numbed.  Living “consciously” (numbed) in the in-between, denying your understanding that you are pushing against your values is a terrible feeling.  This is how fortresses of lies are built.  Lies to oneself and those around.  This is how we make living a less than satisfying life HARDER than the alternative we were so previously afraid to pursue or deal with (it cost too much vulnerability). It takes more work to defend a life we aren’t made for and don’t want, and somehow, that so often happens.

Learning to Accept the Humdrum (Habitually accepting defeat)

It can become a necessity to defend poor behaviors and choices for one’s own pride- at all costs.  We are wired for some type of consistency.  Our understanding of what is acceptable is shaped by our previous connections and agreements (even our most recent flawed ones we learn to complacently perpetuate).

David Foster Wallace Gets It

In Infinite Jest, one of the characters who tries not smoking weed for a time, chooses to smoke one night.  He preps for it. Wallace lists:

  • The food the character buys (it’s a long, entirely relevant munchie food list)
  • The setting he creates
  • The mindless activities he prepares  (lots of television)
  • The medications he will need to digest the abundance of food (lots of Tums)
  • How he will prepare for the next day and reintegration

Point? The amount of work that goes into doing something temporarily comforting is not worth the weight of the failure’s affect.

Bringing Inconsistencies to Light

When inconsistencies are brought to light for me, I need to deconstruct them piece by piece so I can get over such a and such a thing.  Or, look at such and such better (adapt my perspective or approach).  Sometimes I miss pieces or parts in my deconstruction process.  But I will often learn what I missed soon enough. A lot of times I set goals and fail.  I have to figure out the reasons why so I can be successful.

  • What part of my perspective is flawed?
  • How can I change my thinking?
  • Does my current schedule have too much power in dictation?

Purpose of Goals

The beauty of goals is NOT to represent success or failure.  People get afraid to talk about hard things because of what it represents.  “Oh no, failure.” “Oh no, I announced it to the world and didn’t measure up.” “Oh no, our relationship is not perfect.” “Oh no, I don’t ALWAYS [insert source of pride here].” “Oh no, I did something really wrong that I said I wouldn’t do.”  There has to be vulnerability, honesty and humility in goal setting.

The purpose of goal creation (to me) is to create movement.  Growth.  Forgive yourself when you need to, prioritize your values over your habits or your whims, learn what works and learn what doesn’t.

The Steps by Steps and Day by Days

“It’s all about the journey.”

This goal setting and planning stuff can be hard.  It can be hard for years at a time.  But I’m finding that it helps put things in perspective.  It helps you to tune out the noise and look inward. To conquer your major and minor struggles step by step, not always on your own.  Not always with a victory dance.  Sometimes achieving in silence, but with deep satisfaction.

When you are successful in the little things… the big things come.  Goals are supposed to be humbling and stretching.  They give you the ability to make your days as full as possible and feel as if you are sucking the life out of life.  They make you feel like you are really living- grappling, getting everything you can, giving everything you can, failing, falling, succeeding, understanding, forgiving, enjoying, being present.  These days, I think this is a challenge- a challenge worth the fight.

Other Obsessive Planners

Of course I am not the only obsessive planner in the world, nor is that the only way to live.  It is, however, the best way for me to live with my history and personality.  Here are some other obsessive planners I think are really cool.  Many are also morning people… :)

Happy spring,


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