Goal Planning for Optimal Enjoyment

Let’s say you’ve set some goals for yourself, and now you want to map out a basic plan for how you’ll achieve them. How do you do this?

Obviously there are many ways to plan your action steps, but as a generalization it seems intelligent to aim for a plan that you estimate will consume the least time and resources. All else being equal, if Plan A takes three months and Plan B takes six months, you’ll go with Plan A. This is just common sense, right? You essentially look for the shortest path from your current position to your goal.

It’s OK if your estimates aren’t accurate — the point is simply that most of us would consider a shorter path to be more intelligent than a longer path. This is particularly true in business. A direct path to an objective is considered more intelligent than a circuitous route. Time is money, and delays can be costly.

The myth of the shortest path

As intelligent as this logic may seem, I happen to disagree with it (go figure!). While I think such an approach to optimization is fine for machines, it’s suboptimal for human beings.


The problem appears during implementation of the plan. What do you actually experience during the action phase? Do you implement your plan like a machine, completing task after task in order? Or does something entirely different occur?

Personally I’ve never met a human being who worked like this, and I’ve never seen a business do it either. Plans often fall by the wayside during the implementation stage. Some would say it’s because people are bad at implementation, but is that really true? Or was the plan flawed from the beginning because it failed to accurately account for human nature?

I’ve produced some beautiful step-by-step plans on paper. But my implementation has usually been less than stellar. I’ll get off to an OK start for a little while, maybe a day or two. Then I stumble. Sometimes I get distracted. Other times I feel the actions are just too tedious, and I find subtle ways to procrastinate. And other times I feel lazy and unmotivated to work on them. Even though I really want the results, I usually reach a point where I just don’t want to complete the next action. Sometimes I find a way to push through my resistance. Other times I rework the plan or move onto something else that seems more interesting (often repeating the cycle once again).

Have you ever experienced this pattern yourself?

Planning vs. implementation

At first I figured I just needed to keep working on my self-discipline. That did help, but it only encouraged me to set bigger goals, so I still eventually ran into the same problems on a larger scale. After failing to get the results I wanted, I considered that the problem might be upstream. Maybe my implementation was poor because my plans were flawed to begin with.

That wasn’t an easy conclusion for me because planning is supposed to be one of my key psychological strengths. According to the Myers-Briggs test, I’m an ENTJ, aka the Field Marshall (a good tactical and strategic thinker). And the test from the book Now, Discover Your Strengths (which I highly recommend) showed that my #1 strength is strategic thinking. So the last thing I would have suspected was that my planning was flawed. But I wasn’t getting results by pushing myself to become better at implementing, so I figured I had nothing to lose by honing my planning skills.

I bought fancy project management software, studied various planning methods, and learned how to break everything down into intelligently prioritized actionable steps. But to my chagrin this investment didn’t pay off the way I wanted. My plans looked better than ever, but I was still no better at implementing them.

Of course some people are better doers while some people are better thinkers, and I definitely enjoy creating plans more than implementing them myself, but I’m not presently surrounded by a team of willing doers, and there are some projects that can’t be delegated easily, particularly in the realm of personal development. I’m certainly capable of taking massive action under the right conditions — I just needed a way to create those conditions more frequently.

Planning for optimal enjoyment

I put this problem aside for a while, and one day when I was journaling, a different approach came to me. Instead of trying to plan the most efficient path to my goal, what would happen if I tried to plan the most enjoyable path?

My initial reaction was, “Nah, that wouldn’t work. It would consume too much time and too many resources. The most enjoyable path would probably be terribly slow.” But as I gave it more thought, I had to admit my current approach was taking way longer than I’d planned anyway, so maybe an approach that appeared longer would actually take less time than the seemingly optimal one. Hmmm….

This “most enjoyable path” began to reveal some interesting possibilities. If I planned a very lengthy and resource-intensive route to my goal, a tediously slow path wouldn’t likely be the most enjoyable one. So I figured the most enjoyable path couldn’t be too suboptimal.

I wondered what such a plan would look like in comparison to its supposedly more efficient cousin. I thought about some of the changes I’d make to craft a thoroughly enjoyable plan:

  1. Select interesting projects. Favor projects I enjoy implementing vs. only looking to the end result.
  2. Add variety. Break up long stretches of repetitive work. Work in different locations. Take field trips.
  3. Improve balance. Blend solo time with social time. Balance physical work with mental work.
  4. Create a pleasing work environment. Relaxify my workspace so I enjoy spending time there.
  5. Involve others. Find a way to get friends involved. Form a mastermind group.
  6. Solve problems creatively. Favor creative off-the-wall methods when the obvious solution is too dull or tedious.
  7. Enjoy plenty of downtime. Keep motivation high by avoiding overwork. Take vacations. Enjoy rewards for achieving mini-milestones.
  8. Avoid the unpleasant. If a step can’t be done enjoyably, find a way to delegate, outsource, or eliminate it.
  9. Use intention-manifestation. Focus intentions to gain assistance from the Law of Attraction.
  10. Design for flexibility. Allow daily choice making where order of task completion isn’t critical.

As I began to understand what an enjoyable plan would look like in comparison with an efficient one, I realized it was a very different way of working. It’s congruent with the Emotional Guidance System concept from the book Ask and It Is Given because the idea is to remain in a state of joy throughout the entire project. So you still have a specific goal in mind, but along the way your focus is on enjoying the journey rather than reaching the destination quickly. Instead of planning the steps that will allow you to achieve your goal as efficiently as possible, you plan the route that you’ll enjoy the most.

Technically I began working with this paradigm in 2004 when I retired from the computer gaming industry and started this personal development site. That immediately enabled me to begin selecting projects I enjoyed more. Although I liked running my games business, I enjoy this personal development business a great deal more. After working so long with the efficiency-based model, it’s been a real challenge to let it go. I am getting there though because I find that the enjoyment-based model produces better results for me, both in terms of enjoyment and efficiency. At least for me, the most enjoyable path may well be the most optimal one.

Consider testing this planning model to see what results you get with it. You spend your entire life in the present moment, so it makes sense to ensure that in this very moment, you’re in a state of joy. Clearly you won’t accomplish that by planning to spend your life completing tasks that you find tedious, painful, boring, or pointless. The switch to an enjoyment-based paradigm can fill your daily reality with creativity, joy, and fulfillment. Ultimately all those present moments add up to your entire life. If you enjoy your present moments, you’ll enjoy your life as a whole.