It has always seemed best to have plans. Plans of all scales. If we do dream big, we naturally start with the big ones. The pie-in-the-sky plans so bold they may span decades. These are the life dreams. They should be in the realm of reason, but a far reach. These plans may involve multiple stages, require significant change, and necessitate obstinate endurance to realize. 

Dreaming big is a powerful process. You have to know what you want, imagine the possibilities, see yourself ascending to great heights, stoke your ambitions, and summon deep passion. It is difficult to arrive at a distant destination without a map. There are so many turns one has to take. A plan for big dreams, though no guarantee, gives you the best chance for success. It helps you know which direction to go at the innumerable decision points along your journey. Most of all bold plans inspire us and encourage us to believe in ourselves and our potential.

Modest plans have also always been essential for me. I am a hope for the best, plan for the worse kind of person, so modest plans make me feel safe with the knowledge that an acceptable destination is relatively easily within reach. This safety actually helps me to dream bigger, be bolder, and reach further than I would if I were perpetually afraid and unclear about achieving a comfortable sustainable existence in the meantime. I actually center my day-to-day life in this modesty. The result has been that I am often living happily and comfortably below my means. This provides a cushion that is sometimes necessary to burn through and a margin that can be reached in order to traverse those steps in bolder bigger plans that require risk and reach. Modest easily reachable plans may actually constitute a continuation of your present existence. Or not. They may be an option among many that are more likely, easier, slower, closer to home, or more naturally suited to your present. 

The most important role of modest plans is to account for the reality of risk. Try as we might, wish as we may, we don’t always control everything. Often enough, conditions and circumstances outside of one’s control may entirely block your path to your big dreams. Your big dreams may be really wild ones. If that has never happened to you or you believe effort overcomes all obstacles, fantastic. Again, I’m a plan for the worst and hope for the best sort. In my experience and worldview, shit happens. Sometimes you can thwart the unwelcome, and push it off your path. Sometimes, though, it is an immovable obstacle. There may be a way around it. Adaptation is a key component of good planning. 

Timelines are necessary organizational tools and powerful motivators. In practice, they might tighten but tend to slide. How many of you have been given an assignment only to realize that the timeline required is just not going to happen? Working nonstop might help, but then quality would probably suffer as a consequence. Sometimes it’s just not possible and you know you are doomed. It rots to be punished for unrealistic timelines, but it happens, especially when you could see from the start that it was going to be a train wreck. Most often, you cannot know or predict what will happen along the way. It does depend on what you are doing. Some activities and some disciplines are better suited to clear paths toward completion. Others, almost by definition, aren’t. Think about mailing a big order vs designing the product you will mailing. MORE

Timelines and time constraints can be used for all kinds of good and effective reasons. If I am dreading a task, I might set a time limit. This inspires me to finish it quickly knowing that when that time period is over, I can move on to something more enjoyable. When making your own plans and defining timelines, You don’t have to make misery with impossible timelines. So, in your planning, leave room for unexpected events and adaptation to conditions as they arise.

Let’s get back to plans. Once you have fleshed out your bold plan and your modest plan, it’s a good time to take a moment and see if they are unhelpfully out of alignment.  Is your modest plan taking you in an entirely different direction or an actual fundamental hindrance to your big bold plan? Ideally, the modest plan is possible to achieve while you are progressing with the bold plan. You can do both at once or achieve the modest plan then work on and off towards the bolder plan as you are able.  The modest plan might even be an early step on the road to the big plan. Like booking a train to a far snowy mountaintop, but getting off in the foothills. Reaching the foothills is cheaper, easier, more comfortable, and there are more people going to the same destination. Reaching the mountaintop separates you from the crowd, and requires planning, time, and resources to get there safely and even more to establish yourself enough to stay.

With bold and modest plans laid out, is there an intermediate path that now seems intuitive? If you achieve your modest plan more easily than anticipated, it’s nice to have an intermediate path to strive for, particularly if your bold plan scares you a little (or a lot). 

Plans shouldn’t be static. I like to keep my original plans even as I modify and adapt them as I go. It helps me to see how things have evolved. There is learning in this. What actually came to pass? What did I predict? What did I not see coming? How does this help me shape better plans for the future?

I’ve intentionally not been specific about whether these plans are personal or professional. That’s up to you. Where do you need a plan? What matters most? What would benefit from intention in your life? You may have multiple goals in different aspects of your life. Plans are guides with mapped-out paths to a possible destination. They serve us by ensuring that we take the necessary steps at the right times in order for arrival to even be possible. Without a plan, it’s far less likely to arrive where you intended to go, especially with big dreams. Plans also help in a sort of subliminal way. Whenever we come to a crossroads, choice, or decision point, having the plan in mind can nudge us in a helpful direction in ways we may or may not be aware of.

If you’ve rummaged around looking at planning there’s a daunting abundance of overlapping methods and terms. I’ve found that there is no common understanding of the terms, so it’s best to define them for yourself in a way that suits your purposes. Ultimately, it doesn’t matter what terms you use as long as they work for you and help you fully think through your planning. I offer a set of terms and definitions to get you started, tighten your usage, or inform your adaptation. Because these terms are often synonymous, the definitions offered here distinguish them from one another and establish the relationships between them. These definitions also establish a hierarchy with respect to the overall plan. They are what I’ve found to be the most useful to define distinct and important aspects of good planning.

Okay, so you’ve got your bold, modest, and intermediate plans. These are your goals. The next step is to think of the strategy that you will take to reach them because there is often more than one way to achieve your goal. With the strategy in mind, define the objectives necessary to achieve your goal. It helps to think of the tactics you will use in meeting your objectives. Again, there are often multiple ways to achieve a given objective. At this stage, it helps to begin to fit your objectives into a timeline. 

The next step in defining the tasks necessary to achieve that objective will enable you to refine your timeline. Tasks may be defined as you enact your plan as they might be dependent on the objectives, tasks, and timing that came before them. Tasks can then be scheduled into your calendar or whatever you use to track your activities day to day or week to week. Again, the time periods you use should suit you. Finally, do take time to define the measures of successfully completing a task, achieving an objective, and reaching a goal. 

The measures are really important for your planning. They determine how you know you’ve succeeded at any level of a plan. For tasks, they may be evident. The completion of the task itself may be the measure. For objectives, it may not be so clear as these by the provided definitions are broader in scope than your tasks. It is helpful to be sure when you define the measures that you use to test whether your goals, objectives, and tasks are specific enough. Vagueness in planning is unhelpful. You need to know what actions need to be taken to take your next step on the path toward success.

Demarcating and celebrating when important milestones on your path have been met is a great motivator. The journey is as important as the destination. Taking time to mark your progress can help you see how far you’ve come and appreciate all the efforts you have taken. 

From here, adaptation is key. Depending on your goal, revisit your plan and timeline at appropriate intervals or when events prompt consideration and integration into your plan. Re-evaluate the objectives, tools, strategies, and even the goal itself as you proceed. We grow and change as we get older. Life happens and changes our paths and desires. New realms previously unimagined may open up. New goals and/or strategies may need to be considered as intended paths are blocked or altered. You may find you need to add new goals and plan for them as time goes on. You may even achieve your wildest dreams and dream even bigger.