Our mission as a company is empowering potential.

This is rooted in our core belief that all people—no matter their job, goals, financial situation or background—deserve to feel empowered and in control of pursuing goals that are personally meaningful. As individuals, our goals and the contours of our lives are unique. This is why we are committed to providing resources supporting personalized approaches to planning.

This planning guide isn't a sales funnel. We aren't gatekeeping it behind a demand for your contact information. It is completely free and without obligation.

What we aim to provide here is a comprehensive walk through for creating a personalized planning system. Our focus is understanding your unique requirements so you can identify the blend of tools and processes that meet your needs.

The process of building a truly personal planning system takes effort. However, the payoff is significant.

We are excited to be a part of your journey and seeing where it takes you.

Your teammates in progress,

BETTER MADE PLANS

We all just want to feel in control.

That even when we are overwhelmed with tasks, we have the means to put order to the chaos and get a sense of direction.

The problem is, there is no toolbox taught for how to feel empowered and strategic in the face of constant urgency. As we move through life we patch together solutions and succeed mostly through white-knuckle grit while desperately looking for a better way. In that desperation, we encounter a wave of gadgets, planners, and life hacks flooding our social media feeds marketing themselves as the ultimate all-in-one solution for the productivity challenges of everyone and anyone.

With hope and optimism, we buy the planner or the app and sign up for yet-another mastermind class believing this time it will be different.

But then friction emerges.

The complex, multi-step process, demands too much time in our schedule each day... There is too little structure so the “why” behind the different planning activities isn't clear… The tools track too many things or too few… It doesn’t integrate well with the systems we use at work or locks us into yet another app subscription...

Most commonly, these products promise to be a solution for our whole life, but are only geared to manage productivity within narrow parameters.

We get frustrated. We use the tool less and less. We eventually stop using it all together and go back to white-knuckling it.

And because it was sold as the next, greatest, guaranteed-to-succeed tool its failure makes us feel like a failure personally.

The reality is, there is no such thing as a universal planning system.

While some of us are lucky enough to find an off-the-shelf, all-in-one, planning tool that fits our life perfectly, that outcome is rare. And if it does happen, unfortunately, it is often after a long and painful process of trial-and-error driven by glossy, over-sold, marketing promises that leave us discouraged when they fall short.

The main issue is that most planners and planning advice—by selling themselves as universal solutions—operate with the expectation that you bend, shape, and squeeze your life to fit their system, when the system you use to plan your life should be structured around your life.

Better planning starts with you as an individual —your unique goals, preferences, productivity style, environment—and flows to finding planning processes and tools that work in harmony with your requirements. Rather than the promises of a magical cure-all for productivity challenges, it is about cultivating awareness about how you work best so you have the knowledge and skill be selective and strategic as you build and refine your planning practice now and into the future.

In addition to building self-awareness and understanding our needs, building an effective personal planning system also requires a concrete understanding of what good planning looks like. Planning as an isolated process is straightforward, but planning across life and across long-term, near-term, and immediate time frames is complex and challenging if you don't have a strategy. Building a system with tools and processes that support our unique needs and that addresses planning requirements for all parts of life is the key to feeling empowered and self-directed no matter where life takes us.

The goal of this guide is to broaden your perspective on what whole-of-life systematic planning looks like and help you build a personal planning system that works for you. This process is broken out into three parts:

PART 1 - CREATING THE FRAMEWORK: Defining the elements of effective planning and building self awareness about your unique planning needs.

PART 2 - BUILDING THE SYSTEM: Using your framework, identifying the tools and processes that will serve as the initial system workflow.

PART 3 - IMPLEMENTATION AND REFINEMENT: Cultivating a solution-focused mindset and leveraging techniques to review and improve the performance of the system over time.

Building a personal planning system is a process that requires an investment in time on the front end to explore how you work best—however, the long-term payoff in consistency, focus, and performance is life-changing.

PLANNING is about building a vision for the future and charting the path to get there. Building a planning system starts with understanding what that process looks like relative to our personal planning needs.

Whether it is a business goal, a fitness milestone, a contingency plan to address a potential risk, or coordinating a fun weekend with friends... Planning is about identifying a strategy to achieve a particular outcome or reach a particular destination.

At the core, all planning involves the same phases:

• GOAL SETTING: Where are you starting and where do you want to go?

• IDENTIFYING ACTION STEPS: What is the path from here to the goal?

• EXECUTION / MONITORING: Taking action and evaluating whether those actions result in the expected progress towards the goal.

Where planning—especially effective planning—differs from just "taking action" and "doing stuff" is INTENTION and FOCUS. Merely doing a lot of things without a prioritization or direction is motion—not progress—and oftentimes sees us going in circles right where we started.

PLANNING is about establishing a direction, destination, and a course so that our activity moves us purposefully towards things that matter.

The basics of planning when viewed in isolation are often deceptively simple. For example, the process of planning a weekend trip has well-defined constraints (dates, length of trip, budget) and expected outcomes.

The challenges of planning emerge when we need to coordinate activity towards multiple goals across different areas of life (work, home, etc) while also managing the requirements of daily functioning.

The key element that allows us to accomplish big, meaningful, goals in life is creating a vision for ourselves across areas of life (work, social, financial, health, etc) that transcends daily fire-fighting. These big things we want are not achieved with one singular act. Rather, big goals are accomplished over time with the discipline of scheduling and prioritizing goal-based tasks in an iterative process in the midst of all that daily life requires.

The transition from planning for specific goals in isolation to building coordination amongst them in a whole-of-life strategy is the essence of transitioning from BASIC to SYSTEMATIC planning.

The integration of long-term vision, intermediary way points, and daily activity involves planning across the LEVELS OF PLANNING while ensuring that we are building a well-composed life overall involves intentional planning across all SEGMENTS OF LIFE. Together they form the core functions an effective PLANNING SYSTEM needs to address.

In 1967 Charles Hummel published a booklet called the Tyranny of the Urgent. In it, he gave a name to the pressure to reactively focus on immediate high-urgency activity like answering phone calls or doing short-deadline busywork tasks. He noted how this focus on high-urgency immediate tasks keeps us from being proactive on strategic tasks that are less urgent but ultimately higher yield long-term.

Before the advent of e-mail and constantly connected lives, Hummel saw the danger in focusing on productivity only in terms of doing "a lot of things" rather than focusing on the "right things" for our long-term growth and success.

Having goals, priorities, and plans focused across different timeframes and scopes (long-term, near-term, and daily) makes it easier to identify amongst competing priorities what should be done next. This requires deliberate focus on integrating different levels of planning.

DEFINITION OF PLANNING LEVELS

Organizational planning in business is oftentimes framed around four levels (STRATEGIC / TACTICAL / OPERATIONAL / CONTINGENCY) to create a structured hierarchy that translates big-picture goals down to how we prioritize and focus activity day-to-day. Since we encounter similar challenges in integrating activity over different time scales as individuals, these four planning levels are a useful in this context as well. The scope and definition of the levels are as follows:

STRATEGIC

Strategic goals and plans have a long-time (multi-year) horizon and related to foundational values and priorities.

TACTICAL

Tactical goals and plans exist near-term (months / year) often directly in support of strategic plans as foundational work or intermediary waypoints.

OPERATIONAL

Operational planning is organizing daily activity and coordinating amongst regular life tasks (errands, meetings, "life admin") and the tasks that need to be completed to support our higher-level goals. NOTE: The OPERATIONAL level is where urgent-immediate daily tasks collide with activities that support our higher-level plans and as a result is where the greatest focus on balancing priorities is needed.

CONTINGENCY

Outside of the flow of STRATEGIC/TACTICAL/OPERATIONAL planning, there is the idea of contingency planning that focuses on anticipation and preparation for the unknown. Contingency planning is less about scheduled actions and more about having planned responses should specific situations arise.

EXAMPLE

Moving from the theory of planning levels to a practical example we can see the benefits of the structure as a framework for how we coordinate activity over time:

Sam prioritizes physical fitness as a part of overall health. They have set a long-term goal of achieving and maintaining a specific level of physical fitness as a measure of their desired level of health (STRATEGIC PLANNING).

As a part of achieving their strategic health goal, Sam took up running and set an tactical goal of completing a marathon next year as a benchmark of their cardiovascular fitness (TACTICAL PLANNING).

As a part of training for the marathon, Sam is following a training schedule that has a recovery run planned for Monday. This will need to be scheduled amongst an end-of-year presentation at work and attending their daughter's basketball game (OPERATIONAL PLANNING).

Recognizing they have previous sports injuries, when starting marathon training Sam reached out to a Physical Therapist to discuss ways to train safely and to have a provider established who is aware of their history should another injury occur (CONTINGENCY PLANNING).

What this example shows clearly is how deliberate and thoughtful consideration of the different levels of planning empowers daily action and creates a clear roadmap between that daily activity and higher-level goals.

It is important to note throughout that planning is an ongoing process. Life inevitably will get in the way of our plans at points (an injury occurs, the race gets cancelled, something happens that diverts from a training). The usefulness of being explicit about how goals connect across levels of planning is being able to step back and view the impact of disruptions within a framework to adjust course.

The LEVELS OF PLANNING help us understand how different goals and activity interconnect across time and scope which allows us to balance perceived urgency against value for long-term priorities.

A well-rounded life requires a vision and planning that cover the whole of our life, not just our work.

Knowing how to set goals across the levels of planning is meaningless if we don't know what goals to set. A key consideration in a whole-of-life planning system is ensuring that we pay attention to all different areas of life. To do this, we need to have a framework for breaking life down into segments so we can be deliberate about giving each area focus.

Consider your life and activity as a pie that needs to be divided into slices (segments) so that the whole is accounted for.

Different lives have different blends of priorities, so how we divide life into segments will be different for each person (for example, one person may lump all professional activity into one segment while having multiple granular segments to address family priorities while someone else may do the opposite).

Defining segments for planning purposes is not an abstract intellectual exercise. Being thoughtful about tangibly defining how we categorize our activity clarifies priorities relative to particular, real-world, situations. As it relates to the mechanics of the system, defining segments also helps later with aligning tools and processes to manage like-things together.

As you begin considering your specific needs, key considerations in identifying segments for your personal planning system include:

COMPREHENSIVENESS

Your segments together should represent the entirety of life with no overlap. A comprehensive set of segments that are also non-duplicative ensures there are no blind spots or categories of activity unaccounted for.

CLARITY IN SCOPE

An expansion on comprehensiveness is being clear what is included within the different segments. While activity in one segment may influence other areas (for example, your health can impact your ability to participate in a specific hobby), segmenting is about identifying where different issues and their associated planning will be manged within our planning system to keep processing clean and consistent.

REFLECTS YOUR PRIORITIES

The segments you choose are not set in stone and do not have to be equal in size. They also can evolve as your life or as your planning system evolves. But throughout, the segments you choose and how you define them need to reflect your personal priorities to place emphasis on what matters most to you.

BALANCED COMPLEXITY

As you build your framework, you want to define segments so they are specific enough to reflect priorities and allow for deliberate focus while not defining so many that engaging them becomes cumbersome. There is no schoolhouse answer for how many is too many or too few. Rather, this is something to proactively evolve over time based on your experience.

EXAMPLE

Exploring how segmenting appears in a practical example shows how comprehensiveness, clarity in scope, prioritization, and complexity can create a useful framework that can serve as a checklist for planning.

Sam is an established mid-career professional, married with two middle school-aged children, who prioritizes family. Sam is active in their community and sits on the board of a non-profit. In their free time, they are also active in a running club and train for a few signature races each year. At work, Sam is actively preparing for promotion and would like to be competitive in the next 3-5 years to move into leadership.

SEGMENTS AND SCOPE:

• PROFESSIONAL: Leadership Experience / Projects / Training / Networking / Normal Duties

• HOME: Family Relationships / Parenting / Financial Goals / Household Admin

• SOCIAL: Friendships/ Community Involvement

• SELF: Physical Health and Fitness / Personal Development / Emotional and Mental Wellness

The scoped topics beneath the overall segments do not represent all potential topics that fit within, but are specifically called out as the things that Sam is prioritizing most right now. Together, however, the overall segments create a framework and provide a "home base" thematically to engage and plan for any issue that may come up.

Defining segments builds on our understanding of the levels of planning and gives us an architecture to be systematic and thorough no matter the area of life or scale of the specific goal.

An effective planning system is about making our planning needs and the plans themselves consistently visible so we can take action.

The purpose of understanding the phases of planning, levels of planning, and defining how we want to segment life is about defining our planning needs explicitly and making them visible. One of the most common reasons for plans getting disrupted is the failure to take consistent action after goals or plans are allowed to be "out of sight, out of mind."

The singular task of a planning system is to facilitate this visibility and empower decision making. To this end, the definition of a PLANNING SYSTEM is:

TOOLS AND PROCESSES that manage the PHASES OF PLANNING across the LEVELS OF PLANNING for all SEGMENTS OF LIFE.

In the previous sections, we created a framework of the segments of life that are important to us and built our understanding of what planning looks like across the hierarchy of time frames / scopes. The final step before tool and process selection is to identify our individual constraints and requirements that will guide our selection of planning tools and processes.

Our priorities, personal goals, personal circumstances, preferences, and logistical constraints are uniquely ours and all of those different parameters will influence how well or poorly different planning tools and processes perform.

Understanding those personal parameters and selecting tools that account for them will help reduce friction in planning, and in turn, will increase the probability that your planning practice succeeds. Individual requirements have two types—HARD and SOFT—that impact our tool and process selection in significant ways.

HARD REQUIREMENTS DEFINED

HARD requirements are conditions or constraints for how you do things in life that are externally determined and inflexible. For example, your company requiring projects be managed using a specific software, having a job where your calendar of appointments is externally managed, or having limited internet or technology access. Each one of these requirements shape what planning tools and processes you can use and will categorically exclude some from consideration.

SOFT REQUIREMENTS DEFINED

SOFT requirements reflect preferences, broader environmental factors, or personal productivity style in a way a way that is not determinative for what tools or processes you can use but are important considerations to reduce friction. Examples of soft requirements include the structure of your day (activities you choose at the beginning / end of your day), how much time you generally have for planning, preferences for paper over screen-based planning, or preferred level of detail and complexity. Identifying your soft requirements is the result of personal reflection. Exploring the situations where you have felt most effective or where planning went particularly well or poorly will help you identify your soft requirements. As you build a system and refine it with time, your understanding of how you work best will continue to evolve and can help you evolve your planning system.

NOTE ON TIME:

Planning takes time and executing a plan takes effort. Part of building a planning system that works for you is being honest about the time and bandwidth you have to dedicate to planning on a regular basis. The goal is to optimize the return on your investment by finding tools and processes that most efficiently achieve the outcomes you desire. However, not being mindful of your constraints related to time and adopting tools that are overly complex and time intensive relative to what you can commit is a recipe for friction and frustration.

In identifying your soft requirements, pay particular attention to the time you are willing and able to dedicate to the process of planning when considering tool options.

ASSEMBLING YOUR FRAMEWORK

How levels of planning, segments of life, and your hard and soft requirements come together can be thought of like a matrix with segments along one side and the hard and soft constraints along the other.

As you fill in the matrix consider how requirements differ across areas of life. As a part of this review, it is important to also think about whether there are any requirements related to the levels of planning or phases of planning that need to be captured that are unique for specific areas of life.

Being deliberate and thoughtful in this process is key to identifying tools and processes that work for you. The more honest the evaluation of not just externally imposed constraints but also our own preferences, the more likely we will pick tools and processes for our system that will perform as we want.

Ultimately, as your life changes and as you evolve your productivity practice, the requirements in this matrix will also evolve. The primary value of this structure is to keep the interplay between the different facets of effective planning (levels, phases, segments) visible so we can make how we evolve our planning system thoughtful and deliberate.

A hacksaw, an axe, and a table saw all cut wood —but they aren't interchangeable. A lumberjack has very different needs than a cabinetmaker even though both are woodworkers. Similarly, the right planning tools and the processes you put in place are not just about function broadly but how that function is performed and the specific result it achieves relative to your planning needs.

The goal of building out an understanding of the parameters of good planning (phases, levels, segments) and our own personal hard and soft requirements was to begin the process of understanding the form and performance expectations we have for our planning tools and processes.

PLANNING MECHANICS

Planning is a concrete activity and so understanding the concrete functions that need to be performed defines the performance expectations we have for tools and processes. When we consider planning on the action level, there are three key functions (we will define them as the "three C's") that need to be completed on an ongoing basis:

• CURATING: Establishing goals, scheduling activity, and performing macro-level planning on a regular basis (daily / weekly / monthly) for the different levels of planning across areas of life.
• CAPTURING: During the course of executing on our plans, documenting new planning needs, key information related to existing goals, or any other information necessary to support planning.
• CATALOGING: Establishing and maintaining a repository for planning information (needs, goals, tasks, appointments, schedules, etc) along with any reference material related to your planning.

The three different functions are intertwined and occur on an ongoing basis (as you capture information you need to catalog it, which then supports onward curation). For each of these functions, it is your task to determine the the HOW, WHEN, and WITH WHAT each will be done within our matrix of planning needs.

TOOL SELECTION

There is a wide range of options for planning tools and it is important to be mindful how different attributes overlay with your unique planning needs. Things to consider, include:

• FORMAT: Planning Cards / Sticky Notes / Notebooks / Binders / Phone or Tablet Applications / Desktop or Laptop Applications / Web-Based Applications
• COST: One-Time / Subscription
• PHYSICAL SIZE: Electronic / Card-Based / Notebook (Various Sizes) / Binder (Various Sizes)
• COMPLEXITY / PLANNING ELEMENTS INCLUDED: All-In-One / Modular / Single-Focus (i.e. To-Do List, Calendar)
• MAINTENANCE REQUIREMENTS: Automatic Updates (Technology) / Manual Updates
• TIME REQUIREMENT: Time Required to Complete Process or Use Tool (Daily / Weekly / Monthly)

This is the point where many of the soft and hard requirements identified earlier come into play. As you begin your search for the tools that fit your system, overlaying your requirements on the different planning tool attributes can give you specific criteria to structure your search around. This allows you to stay focused on tangible features that are likely to perform rather than just marketing hype.

It is important to not get stuck trying to find one single planner that will meet all your needs. Having established your requirements, you are armed with the knowledge to make choices about how different tools can fit together in a modular way to meet your needs precisely or even what you need to include in a tool you construct yourself. You are operating from a position of choice and power. (BETTER MADE PLANS started precisely from this frustration with existing planning tool options and the decision to design our own).

COORDINATION AND WORKFLOW

Once you have identified tools it is important to understand how they will work together. Taking the time to walk through common scenarios by visualizing how goals, tasks, and time management flow through the system allows you to anticipate and prepare for potential challenges before you "go live." It also allows you to identify potential areas of friction which might lead to changes in your anticipated work flow. Examples of scenarios to think through or questions to ask are as follows:

• A last-minute task comes up at work: How do I capture it? Where do I catalog it? How do I workflow it and track it for completion?
• How do I plan my day and ensure I am accounting for regular daily tasks as well as strategic and tactical goals?
• When do I schedule my check-ins to review my strategic and tactical goals and set new ones across segments of life?
• During the day, how do I capture new ad hoc life tasks (errands, appointments, etc) and how do I track them to make sure they are completed?
• When I have different goal / task /time management tools for different areas of life due to hard constraints (i.e. work systems v. personal systems) how do I coordinate and deconflict schedules and priorities?

QUALITY CONTROL

When evaluating these scenarios, the questions you want to ask yourself about how the system performs need to focus on the following criteria:

• COMPREHENSIVE: Does the planning system address all planning needs both in terms of the different areas of life but also the levels and phases of planning?

• CAPABLE: Does the system achieve its intended outcomes consistently across situations?

• COMPATIBLE: Does the system overall align with my hard and soft requirements?

If you identify gaps or areas where there is significant friction, it doesn't mean the whole system needs to be rebuilt but it may be worth considering whether any modifications would be helpful. At minimum, it is important to anticipate those challenges and flag them for areas for review and modification when the system goes live.

Throughout the guide, we have used Sam to model system design steps. At the conclusion of the build process, here is how all the steps come together:

Sam identified PROFESSIONAL / HOME / SOCIAL / SELF as their main planning segments and identified key personal hard and soft planning requirements for each.

At work, Sam's company has a hard requirement to use enterprise collaboration and scheduling software to set meetings and manage projects. Even though one of Sam's soft requirements is a preference for paper-based planning, they recognize that for their professional planning they will need to use the company software to manage their schedule and work with team members on project deliverables and deadlines. For their own reference to manage their daily cadence, Sam maintains a minimalist weekly and daily paper planner drawing from the availability the identify in their scheduling software to timeblock deep work and limit screen time during the day.

Each day Sam starts out with 10 minutes to plan their day and walk through waypoints and deliverables. Sam keeps a notebook with them during the day to capture notes in meetings and while working and does a self-closeout before going home where they consolidate updates they received during the day into their work task list and project notes.

Outside of work, Sam tracks appointments and other commitments (including their children's activities) in a shared calendar with their spouse to create mutual awareness. On Sunday, Sam takes a half an hour to look at the schedule for the week and review their personal goals across segments of life. They integrate key appointments and tasks into their paper daily and weekly planners. Sam focuses on operational-level activities for their goals occurring during the week (scheduled runs, children's activities, nonprofit meetings) so they can be prioritized and scheduled amongst regular daily tasks as a given day approaches.

On Friday, while the work week is fresh, Sam updates the goal sheets they use to track way points for key personal tactical and strategic goals and identifies any planning tasks that will need to be done Sunday evening as they prepare for the week.

Recognizing they struggle feeling focused during the weekend, Sam prioritizes taking time Saturday morning over coffee to outline the major errands, tasks, and plans they have along with a rough time block for the weekend so they can stay on track with both their social and productivity goals.

Every month Sam schedules an hour to do big-picture thinking and reflection about their goals and priorities.

The scheduling of regular planning sessions, establishing a clear understanding of how key information will be captured, cataloged, and curated, and the regular check-ins with tactical and strategic goals provide visibility not only day-to-day tasks but also how progress is occurring towards bigger-picture goals. The system overall minimizes redundancy while incorporating elements that address personal preference to reduce friction, ultimately resulting in a greater likelihood of compliance and long-term success.

There is no such thing as completion.

Our lives are not static. Our goals change, our circumstances change, our needs evolve. We grow as people. The systems that help us navigate our world need to be able to be dynamic as well.

Successfully navigating change is about having a mindset that is accepting of change and having a framework for assimilating it.

MINDSET

Whether it is the first steps of implementing a planning system or confronting setbacks, the mindset we adopt impacts how quickly and how effectively we will be able to adapt. By far, the most valuable perspective to take is one that proactively reframes away from negativity towards a solution-orientation.

There are numerous outstanding books on mindset such as The Relentless Solution Focus by Dr. Jason Selk and Ellen Reed or It Takes What it Takes by Trevor Mowad that provide exercises and frameworks for dealing with change and adversity.

These mindsets are essential not only for dealing with challenges broadly but with the frustration that comes with changing habits during the initial establishment of a new planning practice specifically. When doing something new, there is always a period of decreased performance where things feel awkward and there isn't the built up muscle memory for things to feel natural. At this point the promised results of the change are not visible yet which further diminishes motivation.

Pushing through that period is critical to seeing the benefits. Having tools and perspectives to call upon in those moments allow us to maintain focus and remain open minded and curious rather than succumbing to frustration before habits can take root. Should the system genuinely have issues, this perspective is still relevant as it allows us to stay focused on identifying root causes and resolve what isn't working rather than scrapping the effort all together.

FRAMEWORK FOR REFINEMENT

Having a solution-focused mindset approaching implementation of a planning system creates an environment where we are open to refinements and able and confront challenges we encounter. Solution-focused perspectives are a natural pairing with frameworks that allows us to be intentional about identifying issues, constructing solutions, and taking action in an iterative way.

U.S. Air Force Colonel James Boyd coined the "OODA Loop" as a way to describe effective decision making and action in dynamic situations. The cycle focuses on taking in accurate information about a situation (OBSERVE), analyzing its implications / meaning (ORIENT), making decisions about the next course of action based on our analysis of the information (DECIDING), and then executing our plan of action (ACT). The "loop" nature indicates the process should be iterative where each new action brings in new information, new analysis, new decisions, and yet further new actions.

For building a planning practice and refining a planning system, the OODA loop provides a structure for identifying and addressing challenges.

The key for both a refinement-focused mindset and refinement framework is commiting to their implementation. Making the regular review of your planning system with a thoughtful consideration of necessary changes is the difference between getting better cyclically and constant change driven by a desire for novelty. Having an intellectual curiosity and focus on evaluating our experience of planning is the groundwork of not just building, but also maintaining a planning system that works for you.

Similar to the construction of the planning system itself where levels of planning and segments of life are codified and the system is structured to ensure ongoing visibility across the entire scope, refining the system requires we stay present with our experience using it and make the refinement process visible.