What is a Goal-Driven Life? – (Part I)

by Rob Leachman

From the “Leading a Goal-Driven Life” Series

Part I

This Series

Years ago, a colleague was describing his affinity for carefree, direction-free, and largely destination-free travel. As this highly educated and otherwise very organized individual explained, he and his wife enjoyed simply hopping in their vehicle and driving, stopping to take in whatever sights they found interesting.

I always listened to these stories of directionless travel with a mixture of amusement and fascination. Though I never shared this thought with my well-meaning friend, I feared that vacationing in such a fashion could, and likely would, severely limit one’s horizons.  In essence, if I took off with the notion of stopping anytime I saw something that interested me, I might never travel more than 50 miles from home. Those trips might be relaxing, would no doubt be interesting, and might even be memorable. But the world is so much larger and far more fascinating than what can be found close to home. And what’s more, it takes some thought and planning to reach these more distant, and rewarding, locations.

Kind of like navigating the challenges and opportunities of life.


I define leading a “goal-driven life” as simply directing one’s efforts toward reaching a set of well-thought-out goals the individual considers to be important. It’s as uncomplicated as that. Not unlike the destination-less traveler, without a set of goals, or destinations, to work toward, an individual not only doesn’t know how to get there; he doesn’t even know where he’s headed. All too often, in the latter stages of such a person’s life, he might look back with disappointment that he didn’t accomplish nearly as much as he had hoped. More tragically, in some instances, he didn’t even try.

Daily Planning

As a young man, I found that my ability to plan and organize my days and weeks in my head was not nearly as strong as I needed it to be. As I look back on my undergraduate years in college, I took my coursework very seriously. A history major, I not only had a great deal of assigned reading, but I also devoured chapter after chapter from supplemental materials directly related to the courses I was taking. Without more effective organization, I found I ended most days frustrated at having accomplished far less than I had hoped.

To address this issue, I began devoting a few minutes each morning to planning my day. (A bit nerdy, yes, but as I suggested I was studious almost to a fault.) If I was working on a research paper, for example, I might list the related tasks I wanted to accomplish that day. If I had 75 pages of text to read and analyze, I began to break that reading into sections or chapters of more manageable length which I would delineate in a notebook I utilized for daily planning. When I finished reading a section, I ran a line through that listing in the planning notebook (a process I found to be oddly gratifying). At the end of some days, I occasionally found that I hadn’t accomplished everything I had hoped and planned. But overall, through this very brief and extremely simple planning process, I found I was far more productive than I would have been otherwise.

Fast forward fifteen years and I was serving as the principal of a growing and very busy high school. In that role, I had to deal with more staff members, address more issues, and attempt to solve more problems than I could easily handle. I had a good sense of what needed to be accomplished from day to day and week to week, but the complexity of keeping track of those many processes made the job even more challenging than it needed to be. Add in a lack of personal organization and an individual in that position could quickly find him or herself underwater. I know there were days when I felt I was on the verge of drowning. With countless meetings to attend, multiple phone calls and other interactions each day that needed to be documented, not to mention the need to keep track of tasks that needed to be completed, I eventually realized I needed some sort of tool or structure to help keep me organized.

In this era when iPads and other hand-held computers had not progressed beyond the realm of the futurists, I started utilizing a “Franklin Planner,” a book-sized leather notebook very popular at the time that included yearly, monthly, and daily calendars as well as space to allow for listing appointments and documenting conversations and other interactions. When I was completing work-related duties, I seldom could be seen without that brown leather binder.

Franklin Planner

As you might imagine, as a high school principal, I spent most of each day putting out “fires” and working to solve the myriad of problems that inevitably crop up in any school. Some of these issues were serious and vitally important, but many (most?) were not nearly as crucial as they seemed. And I found that if I was not careful, I could devote nearly all of each day to these pressing but relatively unimportant issues. Logically, if you spend most of your time dealing with trivial matters, you have little time available to address the really important issues that greatly impact the quality and effectiveness of the organization you are leading. It became clear to me that I needed to first identify those essential tasks, and then to ensure I devoted sufficient time to address them.

I started the practice of beginning each school day by devoting just a few minutes to reflecting on what I wanted to accomplish before the day concluded. I soon found that a brief period of quiet, reflective thought, in my office before the staff and students began to require my time, allowed me to identify the most important tasks I hoped to complete that day. Some of these tasks were important enough to justify my time, not necessarily highly impactful, but still needed to be done. Other tasks, however, represented the critically important actions needed from a leader working to help the school reach higher levels of performance and effectiveness. These were not tasks that had to be completed that day, and because they lacked the pressing urgency of other matters, they might not have been accomplished had they not been planned and listed. When I completed a task, I marked it as complete, a still satisfying action.

Admittedly, there were times when after charting what I hoped would be a highly productive day, something would occur that would end up consuming most of my time, allowing none of the listed tasks to be completed. But unlike before I instituted this brief, simple planning process, most days I was able to devote significant chunks of time to important but less urgent work on which I might not have otherwise even been focused.

Covey’s “Time Management Matrix”

As I was struggling with these issues, I first became familiar with the writings of Stephen Covey, and his research on time management had a profound impact on me. The seminal work of the late Dr. Covey is The 7 Habits of Highly-Effective People, a book written in the late 1980s that remains relevant and still resonates decades later. “Habit 3” of the 7 Habits is titled, “Put First Things First,’ a simplistic-sounding phrase that, if effectively practiced, could have a huge impact on how much important work an individual can accomplish.

Covey provides a “Time Management Matrix” that categorizes activities based on their level of importance and urgency. Some activities are neither important nor urgent, and as such, they wouldn’t contribute to the advancement of either the individual or the organization. Other activities are urgent but not important, such as attending largely purposeless meetings, taking superfluous phone calls, spending time going through unimportant mail and email, writing reports that will have little effect, and countless other examples. These urgent but unimportant tasks seemingly have to be completed promptly, but in terms of the organization, have little impact. To Covey, time devoted to activities that are urgent but unimportant or neither urgent nor important was largely wasted time. In fact, he suggested that individuals who devoted much time to such activities “basically lead irresponsible lives.” Harsh, yes, but there is no doubt a considerable number of people who spend much of each working day dealing with these unimportant activities.

Conversely, anyone in a position of leadership will inevitably have to complete activities that are both urgent and important. There will be crises that arise that have to be addressed immediately, critical projects that must be completed by a predetermined deadline, and issues of vital importance that must be addressed in a quick and timely manner. A person spending the bulk of his or her time dealing with urgent and important issues is always putting out proverbial fires, moving from one crisis to the next, consistently under stress, and often suffering from burnout. The organization may not advance based on dealing with these activities, but it likely won’t prosper and may not survive if activities of this nature are ignored.

Stephen R. Covey

What surprised me as I studied Covey’s ‘Time Management Matrix,” and an assertion that took me some time to comprehend, was his suggestion that truly effective individuals spend the bulk of their time completing tasks that are important but not urgent. Activities such as developing an organizational vision, researching ways of effectively implementing that vision, working to develop the relationships that will help move the organization forward, and countless others are examples of critically important activities that don’t have to be completed today, or tomorrow, or next week, or next month. As a result, in many organizations they are never completed.

This concept particularly resonated with me. If they were honest and accurate, at the top of the list of job responsibilities for a high school principal might be the aforementioned “putting out fires,” and I could be dealing with minor and largely insignificant crises all day, every day. While some of that work obviously had to be completed, spending all of my time handling “urgent and important” emergencies (not to mention those that are “urgent and unimportant”) did nothing to propel our school forward, to implement the changes and improvements that were needed. This caused a shift in my thinking, making me realize that I needed to place a much higher priority on those strategic, “important but not urgent” tasks that to a large part helped differentiate stellar organizations from mediocre ones. And I used the daily planning process to help with that prioritization, making sure that critical activities were prominently included as I delineated tasks for the day.

Yearly Goals

It was around this time that I started implementing a yearly goal-setting process. I realized that if I was going to base some of my daily planning on the completion of critically important (but not urgent) work, I needed to more broadly identify what it was I wanted to accomplish institutionally and personally, delineating those areas of emphasis, or goals, every year.

To facilitate the identification of these yearly goals, I instituted a process I have now followed for more than three decades. Each year, shortly after New Year’s Day, I set aside some reflective time to just think about what I wanted and needed to accomplish during the upcoming year. I never went into this process “cold,” having previously evaluated progress toward the prior year’s goals and given thought to what was needed and desired for the coming year. And then because our children were very young during those initial years, I traveled to a location where it would be relatively quiet and where I wouldn’t be interrupted. Some of those years I went to my office in the school, which was still on holiday break. Other times I went to a diner where I had breakfast and then completed the goal-setting process in isolation. I recall at least one time when I drove to a secluded spot in a park where I sat in the car and identified my goals for the coming year. More important than the location, I simply needed some quiet time.

This was not a complicated process. I simply jotted down some thoughts on a legal pad, and from those initial notes, I developed a list of around 10 to 15 goals for the year. The goals I selected were typically a combination of personal goals, personal professional goals, and school or institutional goals. Again, these weren’t complex targets with performance criteria or anything like that, but rather statements of what I wanted to work toward accomplishing. For school goals, I focused on major issues and activities over which I had some control and might include the implementation of a new class schedule or the submission of a grant proposal I hoped to successfully implement. For personal professional goals, I might include the completion of a graduate degree program or increasing my involvement in a community or professional organization. For personal goals, I might include running a certain number of miles or increasing my involvement in church or not-for-profit activities, or in more recent years reading a certain number of books. As I got older and moved toward retirement, the school or institutional goals and personal professional goals were increasingly replaced by an increased number of personal goals, just as my life was becoming less professional and institutional and more personal.

These were admittedly broad areas or activities I wanted to address and hopefully accomplish during the coming year. But as I reviewed these goals from time to time through the year, I found they kept me much more focused on the areas and activities needed to move my school, my career, and my life forward. It was not uncommon to not accomplish some of the goals, or at least to not accomplish them completely. But I almost always at least made progress on each of the areas I had identified. As an example, the goal of implementing a new schedule might not have been completed, but we had completed a great deal of the planning needed for its implementation. Or I might not have run the 700 miles I had hoped for, but I logged 600 or whatever, making progress toward the goal.

As each year concluded, I took a few minutes of less reflective time to complete a final review of the yearly goals I had identified. For each goal, I added a notation in parentheses characterizing it as “completed,” “not completed,” or “partially completed.” It was not uncommon for goals in the latter two categories to be included again when I completed the goal-setting process a few days later. And particularly for school-related goals, I occasionally found that conditions through the year made some of those goals irrelevant or no longer appropriate. In other words, there were times in December that I found that changing circumstances had made what I had identified the past January to be no longer pertinent. This was a fluid process that at times required a bit of flexibility due to changing circumstances.

But I truly believe this goal-setting process had a significant impact on what I accomplished in any given year, helped me to become more focused and productive, and helped to enhance my career and the organizations I ultimately led.

Life Goals

In time, I came to realize that yearly goal-setting and daily task identification could be further enhanced by the identification of a set of life goals I hoped to reach over time. Due to the likelihood of changes in employment, I found long-term institutional goals to be particularly challenging, and as a result, I largely excluded them from this process (though I worked with staff and stakeholders to separately establish goals for the school or school district I was leading). This process of identifying life goals primarily focused on personal as well as personal professional areas, and simply delineated some of what I wanted to accomplish in life.

Most of the goals I established, periodically reviewed, and occasionally revised or added to, have been or are in the process of being accomplished. As an example, one goal suggested I would complete a doctoral degree; that occurred in 1999. Another suggested I would attain a position as a district-level administrator; I served as a school district assistant superintendent and then superintendent for 14 years. Still another goal involved the completion of a marathon, which was accomplished in 2000.

I still maintain and follow that list of long-term goals, and some goals have remained since its early origins. As an example, I have for decades wanted to train for and complete a triathlon. Given the inability to run without pain I have experienced in recent years (not to mention challenges related to long-distance swimming), this goal is destined to be removed from the list. Similarly, I set out some time ago to complete a run of at least three miles in every state. Given those issues with running, I have altered that goal to include running, hiking, or walking, but with this revision, I am still making progress toward its completion.

The point is, this is my list of long-term goals, it’s a fluid and dynamic list, and it is subject to constant review and revision. I’ll pull up the list and review it a few times each year, and make revisions as needed. When a goal is marked as complete, I’ll typically eliminate it from the list. If a goal becomes irrelevant (such as the triathlon goal), I’ll alter or eliminate it. But if something is simply challenging to complete, yet still represents a goal that remains important to me, I will be very hesitant to arbitrarily remove it from the list.

My list of long-term goals is private, a collection of aspirations that still serves as a powerful motivator even as I progress into my older years. While my career aspirations have largely been met, there are still some major milestones I hope to accomplish. Some of them I may not, but they provide a framework for continuing to move forward even in my later life.

Goal-Setting Throughout Life

As you can see, I began identifying daily goals, then branched out to establish yearly goals, then finally developed an evolving list of life goals. In many respects, those three elements were implemented in an order contrary to what would be ideal. Logically and ideally, life goals should lead to yearly goals which should help to inform the goals that are established for each day. But life doesn’t always evolve in the most logical order, and when I initiated the identification of daily tasks, that level of organization and motivation was what I needed at the time. Plus, moving from life to yearly to daily goals could be overwhelming for someone simply seeking greater focus and productivity. This system worked very well for me; anyone seeking to begin a goal-setting process must make adaptations to meet his or her needs.


As I write this, I’m 63 and have been retired for several years. It would not be uncommon for someone like me to spend his days drinking coffee, watching TV, and otherwise puttering around the house. I must admit I do each of those things most days, but I also strive each day to be productive. With my wife, I complete some sort of workout almost every day, either a bike ride or a powerwalk on a trail or a workout on a rowing machine or a yoga class. Most days I spend at least an hour or two writing or completing research. And having completed “adventure trips” such as a cross-country bicycle ride and a rim-to-rim hike across the Grand Canyon (each of which was on my list of life goals), we still have other such adventures we hope to complete. In other words, there is still work to be done, and to stop striving would seem counter to living a quality life at any age.

Microsoft To-Do Planner

So, I still maintain my list of life goals. At the beginning of each year, I complete the yearly goal-setting process and then evaluate those goals at the end of each year. And most mornings I take a few minutes to list the tasks I want to complete that day, a fairly quick and simple process on the Microsoft To-Do program I currently utilize. Among the common daily goals I establish are “complete a walk” or “complete a bike ride,” each of which ties back to the yearly goal of how many miles I hope to bike or walk in that year. I typically include a task related to whatever writing project I am working on, which most often also ties back to the yearly goals I have established regarding those projects (which may also relate to life goals I am still working toward). The point is, over 30 years after implementing this process, and in a state of retirement, that process is still providing guidance and motivation to my yearly and daily activities.

I revisit those daily goals throughout the day, checking off those that have been completed, and then do a quick final review in the later evening. I may not always complete all of the tasks that I have identified, but at the end of the day, I sincerely don’t like having uncompleted tasks still on the list, the motivation for me is that strong. At a time in my life when I could be kicking back and doing nothing, this simple goal-setting process keeps me going.


Some may view what I have described as a spontaneity-killing process that takes the joy out of their existence. These are folks who, like the destination-less traveler, want to experience life as it comes to them. I understand and respect their sentiments, and hope and trust they will find the life fulfillment they are seeking. What works for one person may not work for the next.

But as I look back on my life and career, I know that any success, satisfaction, productivity, and fulfillment I have attained has been enhanced, perhaps greatly, by the admittedly simplistic daily, yearly, and life-long goal-setting process I have followed.

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