When looking at your list of goals, categorize them once in terms complexity or duration, and once more in terms of satisfaction. These can be arbitraty numbers for now, say 1, 2, 3, etc...
Next, order the first list with by complexity/ duration from least complex to most. Then, order the second by satisfaction level from highest to least.
Here is an example:
|1||Volunteer at Food Bank (easiest)||9||Write a Novel (highest)|
|2||Clean Basement||8||Earn Master's Degree|
|3||Paint Front Porch||7||Exercise/ Lose Weight|
|4||Live in the Moment||6||Travel to China|
|5||Travel to China||5||Save more Money|
|6||Exercise/ Lose Weight||4||Volunteer at Food Bank|
|7||Save more Money||3||Live in the Moment|
|8||Earn Master's Degree||2||Paint Front Porch|
|9||Write a Novel (hardest)||1||Clean Basement (lowest)|
As you see in this example, there is somewhat of an inverse relationship between the two. I would expect to see something like this from most people. If your number one goal is the same on both lists, then you are lucky; by all means, this is what you probably should get started on right now!
However, if your lists are ranked similarly to those above, then there are three general strategies on which route to take:
1. "Low Hanging Fruit", or in other words, tackle the easiest items first. The advantages with this method are that they will promote the habit of being productive, provide immediate results, and instill a sense of accomplishment. This strategy will de-clutter the your list and build momentum, putting you in a great position to take on bigger challenges later.
The drawback? Time-sensitive goals that score high in satisfaction would be at risk. For instance, someone who is turning 60 may not have the luxury to wait to get off the couch and begin training for that first triathlon.
2. Focus on the one item that would bring you the most satisfaction. Dive into writing that novel or get started on that degree. To quote Confucius, "Choose a job you love, and you will never have to work a day in your life." Success in these areas may reward you the freedom or opportunities that will fulfill your lesser goals.
The drawback? Results and accomplishments aren't as pronounced, nor as frequent. We're putting in for the long-haul and we need to be mindful that the journey does not turn into a death-march. Going down this path may take a lot more planning and discipline in order to realize success.
3. Use the two lists to find a nice comprise. In the example above, "Travel to China" appears to provide a moderate level of satisfaction, and seems relatively straight forward to achieve, all things being considered.
The drawback? Not being the easiest nor the most satisfying goal on our list, we run the risk of giving up on this one all too easily.
As you see, it really is up to you.
Bear in mind, one look online and you can find a myraid of prioritization models that can help you statistically score your choice, but I wouldn't overthink this. When you see your list, generally the top ideas jump right off the page.
How would you choose, David?