Reorientation is key

Reorientation is key

Sometimes it can feel like it takes all the running in the world just to stay in place. Heraclitus says that the only constant thing is change, but “keeping up” is expensive.

It’s easy to consider this with respect to business or other organized endeavors. You might have a competitor who is working to upset your current flow. You might be trying to serve an audience which is itself changing.

On a personal axis, this can be a feeling of being adrift with respect to your goals (expressed or otherwise). It could be the root of feelings purposelessness or anxiety. Tangibly, it might even be the constant need to learn in order to keep on top of your profession.

The key to handling all of this change is the process of reorientation.

Uncertainty and learning are agents of change

I think the biggest source of change is learning. As we make choices and motion to achieve an end, we learn. Often we begin in a state of uncertainty and must learn even to proceed. And then, as we learn our world changes.

For instance, you might have a goal to go on a nice vacation with your family. You can imagine it concretely: a fun trip in a relaxing place, a chance for everyone to focus on themselves and each other as opposed to the stresses of the “real world”. But every time this vision becomes concrete it will begin to change.

  • Your partner wants an exciting vacation,
  • timing doesn’t work out at your job and you end up needing to wait until colder months,
  • you run across ideas for a vacation in the other hemisphere,
  • then learn your passport is out of date,
  • and finally do the research to learn that it’s easy to renew your passport in time.

Now you’ve looking at an exciting vacation in Brazil. Your world has changed.

The foundation of fear of uncertainty is fear of handling change.

We fear change because we’re bad at it

In the short story above each step might be coupled to painful emotions. As your vision shifts under new information you want to hold on to what came before. On the other hand, if you’re really honest with yourself a vacation in Brazil is maybe more exciting than that cruise you originally envisioned.

Change is scary and we’d like to hold on to what we had before, but it’s not necessarily bad. In fact, even if you liked the idea of a Florida vacation, as reality sets in that option becomes impossible. Or worse, compelling entirely because you once believed in it but ultimately very dissatisfying.

The wrong thing to conclude is that it’s bad to make plans. You might have never learned about reality without that original plan.

Instead, you can see all of these as side effects of a lack of practice. Change is exciting and full of opportunity as long as you’re practiced at managing change.


OODA, short for Observe-Orient-Decide-Act, is a tool invented by John Boyd for describing how people make change. It’s sometimes described as a loop, but I think it’s better to see it as four companions.

At any point we might observe new information, make a decision out of opportunity or force, engage with action in business or play, and finally incorporate all of those into a reorientation of our worldview.

Boyd was a military strategist. His actual point with discussing OODA was to make strategies for how to disrupt and destroy his enemies. His tool of choice was change and OODA was his rubric for being better at change than his enemies.

You get better at action by training and habit. You get better at decision through clear leadership and accountability. You get better at observation through recon, technology or you make your opponent’s observation worse through spying and OPSEC.

But the real killer is reorientation. All the rest is for naught if the world has changed but individuals or groups haven’t reoriented—your observations will be misinterpreted, your decisions wrong, your habits out of date.

How do you get better, faster at getting your orientation right?

What does it feel like to reorient?

Orientation is a funny word which seems to make sense abstractly but is very difficult to understand in practice. What does it even mean to reorient?

Emotionally, reorientation takes direct aim at our anxieties. Reorientation is a process of admitting that we’re deeply wrong. It’s not enough to admit that we’ve made a poor decision on the basis of a bad conclusion. To reorient, we have to admit that our whole system of deduction was broken somewhere.

Reorientation is not only emotionally taxing, but mentally taxing, too. It’s an exercise in perception to notice that you’re misaligned with the world. It’s an exercise in consistency and logic to discover why. It’s an exercise in creativity to fix the problem. It’s an exercise in communication and persistence to propagate that fix to all of the other places that need to account for it.

In my experience, reorientation-done-poorly feels pretty awful and is something that you’re very likely to do in half-measures. Those half-measures lead to a bigger lift the next time you need to reorient. Your growing orientation debt turns into cognitive dissonance and even self-delusion before you know it. The expense of changing your point of view becomes overwhelming and self-reinforcing.

Reorientation is a muscle

To recap: change is inevitable, change requires and even hinges upon reorientation, and reorientation is painful and difficult enough to through your whole psychology into a fit.

I believe these things to be generally just true. The economics of this matter make it so that we all live under some amount of reorientation debt. We just can’t afford to go off to a self-care retreat every 45 minutes.

But then that’s exactly the point. If it’s all economics, then the cheaper you make the process reorientation then the less reorientation debt you will carry.

Reorientation is a muscle. If you have a weak back then you will avoid motions which extend and depend upon strength in your back. Doing this for long enough will degrade your back even more. It’s a spiral of death and the only way to break it is… exercise!

Make reorientation cheap

What are practices which make reorientation cheaper? Here are a few ideas:


  • Regular meditation
  • Articulation of your goals, both short and long
  • Doing things for tangible reasons and writing them down
  • Using a GTD-like system to facilitate capture, organization, and systematic review of your commitments
  • Practicing being spontaneous


  • Writing and publicizing clear plans with justification
  • People at all levels being comfortable admitting mistakes and poor performance
  • Regularly revisiting plans—getting practiced at updating them
  • Creating multiple pathways to success and being clear about the weight of commitments
  • Communicating changes clearly throughout teams and emphasizing the emotional need to reorient

I’ve personally found that practicing these achieves better outcomes than not practicing them. I believe the core reason why is the work makes reorientation cheaper.

There are also clear themes to these practices. They center around explicitness, regular review, and exposure to change and the need for reorientation. They are also all well-regarded general advice for your personal and work life.

A license to care

The point of all of this is that reorientation (and OODA at large) is a tool for diagnosing anxiety and stagnation in any arena of your life. Reorientation is expensive and painful and the lynchpin for being successfully spontaneous and proactive. Those things don’t come for free.

The primary way that these thoughts are important to me is that they give me a license to care about this kind of work. It’s extremely easy to kick the can down the road on practices like meditation or clearly stated team goals. They both seem expensive with only nebulous benefit.

Acceptance that reorientation is a muscle and you must exercise it changes that game. Exercise begins as painful, but then it, and so many other things, get easier the more you do it.

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