How to Make a Five-year Plan


As a fresh-faced student at the University of Colorado’s MBA program, I stumbled into a class named “Visionary Leadership”. Little did I know, it was about to change my life. Here’s the kicker: our assignment was to draft a five-year plan. Initially, the idea seemed as far-fetched as a unicorn’s existence. But, plot twist – it turned out to be the most enlightening and practical class of my entire MBA saga. So, buckle up, dear reader, as I take you through the riveting journey of crafting your very own five-year plan, peppered with wisdom from my experience and a sprinkle of humor.

Five-year plan: A Crazy Idea or a Game Changer?

Now, before you roll your eyes and dismiss the idea of planning half a decade of your life, hear me out. Sure, five years can feel like an eternity, and who can predict life, right? But trust me, a five-year plan isn’t about predicting the future with a crystal ball. It’s about creating a vision and setting goals that give you direction and purpose. It’s about asking the big questions: What’s next after high school, university, or that job you’re not too fond of? Even if you deviate from the plan (and you will), it’s about the freedom to steer your ship in a new direction. So, let’s dive in and draft a blueprint of your future, shall we?

Next, we’ll talk about how to start this exciting journey with your core values. Stay tuned for a mix of soul-searching and practical tips!


The Compass for Your Five-Year Journey

Values - 5 Year Plan
Values – 5 Year Plan

Embarking on a five-year plan is like setting sail across the vast ocean of life. And what’s a sailor without a compass? That’s where your values come in – they guide you, keeping you on course through storms and sunny days alike. So, how do you figure out these cardinal directions in the map of your life? Here’s a fun exercise:

  1. Brainstorm Bonanza: List all the values that pop into your head – no filter!
  2. Circle of Life: Draw a circle and write these values around it, placing the most important ones at the center like a treasure and the others towards the outskirts.
  3. Narrowing the Navigators: Select the four or five values that are closest to the treasure spot in the center.

For instance, your values might be Family, Honesty, Adventure, Harmony, and Learning. But here’s a twist: challenge yourself. Are these values truly yours or just what you think should be yours? Be brutally honest or ask a trusty sidekick (a friend or family member) to confirm if these values truly represent you.

Sample list of values:

    • Family
    • Friends
    • Honesty
    • Adventure
    • Learning
    • Harmony
    • Religion
    • Humility
    • Peace
    • Wealth
    • Status
    • Fame
    • Recognition
    • Health
    • Personal appearance
    • Travel
    • Philanthropy
    • Leisure
    • Career

From the list above, we can narrow the list to the following five values. You will notice that the value learning has become growth to better fit a true value. Also, each value has an explanation to better express exactly what the value means.

  1. Growth.
    It is important to me to grow as a person.  Within this, I value learning.  That is, I believe that learning is a valuable component of growth and, therefore, plan to grow as I learn.
  2. Adventure.
    I believe that I am an adventurous person. That is, I seek out adventure.  I challenge myself with adventure by taking risks and by competing against others and myself.
  3. Friends.
    I value time spent with friends and family.
  4. Harmony.
    I value peace among people and tend to avoid conflict. As part of this, I value feedback from others in the form of acceptance.
  5. Honesty.
    I believe that I am an honest person, as confirmed by my friends and family.

With your top values identified and interrogated, it’s time to delve deeper into what they mean and how they’ll guide your odyssey. Stay tuned as we uncover the purpose that drives your quest and breathe life into your five-year plan!


The ‘Why’ Behind Your Five-Year Odyssey

Purpose - 5 Year Plan
Purpose – 5 Year Plan

Now, with your trusty values in hand, it’s time to delve into the heart of your 5-year plan – your purpose. This isn’t about setting a bunch of arbitrary goals; it’s about defining the core of what drives you, the big “Why” of your life’s narrative.

To discover your purpose, you don’t need to meditate on a mountain top (though that could be fun!). Start by asking yourself,

“What do I want to achieve in life?”

Let’s say, based on the earlier values, you want to

“promote understanding among people and natural environments.”

That’s a noble start! But why stop there? Flesh it out with a “so that” statement, like

“so that people come away with a better understanding of each other and the environment.”

But wait, there’s more! Consider the roles you play or want to play in your life. Maybe you’re an aspiring entrepreneur, a devoted family member, or an intrepid explorer. Each role might have a slightly different purpose, but they should all dance harmoniously with your values.

To accomplish writing your purpose, think about goals that you have in your life and what they have in common. If you can find a common theme both in your goals and in past experiences, this will help to define your purpose.

We can also define a more specific purpose; for example, we can describe the purpose for career. This way, we need to ask ourselves, “What is the purpose of my career? And why?” Here is a complete example of purpose:

The purpose of my life is to promote understanding among people and natural environments around the world so that people come away with a better understanding of each other – themselves, cultures, and others’ points of view – and the environment.  I believe that this purpose fits into all aspects of my life, including my career.

The purpose of my career is to create a successful business that promotes understanding among people and natural environments around the world while, at the same time, teaching them about the outdoors in an adventurous setting. This way, they come away with a better understanding of the environment and each other – themselves, cultures, and others’ points of view – and have fun in the process.

Next up, we’ll leap into crafting your vision. Imagine you’re a time traveler visiting your future self. What do you see? Hold tight, as we’re about to embark on the most imaginative part of your five-year plan!


Crafting Your Future Self

Vision - 5 Year Plan
Vision – 5 Year Plan

Welcome to the most imaginative pit stop on your five-year plan journey – creating your vision. This is where you get to dream big and paint a vivid picture of where you’ll be half a decade from now. So, grab your mental paintbrush and let’s get started!

  1. The Time Travel Experiment: Close your eyes and catapult yourself five years into the future. What do you see? Are you in a bustling city, a serene countryside, or perhaps somewhere entirely unexpected? What are you doing? Who are you with? Describe everything in vivid detail – from the aroma of your morning coffee to the texture of the chair you’re sitting on. What type of work do you have? Here you’ll put your dreams and aspirations on paper. What about your personal life? Friends? Family?
  2. Align with Purpose: Remember the purpose we chatted about earlier? Ensure your vision is a glamorous reflection of that. If your purpose involves adventure and understanding, perhaps you see yourself leading an eco-tourism venture or working with communities around the globe.
  3. The Day in the Life: Dive deep and describe a day in your life, five years from now. Start from the moment you wake up to when you hit the hay. What’s your routine? What challenges do you face, and what triumphs do you celebrate?
  4. Flexibility is Key: Remember, this vision isn’t set in stone. It’s a guiding star, not a GPS with a predetermined path. Your vision may (and probably will) evolve, and that’s part of the adventure!

Here is a sample vision, following the example above:

Monday, March 29, 2010
I awake early from my downtown Denver loft, having a big day (and week) ahead of me.  I quickly get dressed, putting on my most professional set of cargo pants and button-up safari shirt.  I cook myself a breakfast burrito – eggs, potatoes, and cheese topped off with salsa – before slipping on my hiking boots and stepping out the door.  Walking down the street toward the office, I look around me, enjoying the early morning sunshine, the skyscrapers around me, the snow-capped mountains to the West and the wide-open plains to the East.

My office is just north of the downtown area in the newly renovated neighborhood of Five Points.  I step inside to the ground floor of a two-story Victorian house that was converted into office space.  The house was a real estate investment that my twin brother Jeff made nearly five years earlier when, after sharing a house in Five Points, we went our separate directions – me into the Peace Corps and Jeff beginning a new job in downtown Denver.  He decided to sacrifice for the good of the business and convert the house into offices.  The business, Twin Travels, covers the ground floor only with the upper level occupied by another business.  With only four employees, including myself, there isn’t a need for a lot of open space.  We share two rooms among the four of us.

My business partner, Jeff, and the two other employees arrive soon after me.  We talk briefly, organize our things and hop in a car for DIA – destination: the Caribbean of Costa Rica. We are headed to Costa Rica to finalize the preparations for the second class offering for our business. The class is called “Indigenous Living Skills: Costa Rica”.

On the way to the airport, Jeff and I discuss the overwhelming success of our first class.  We find it hard to believe that we were able to put things together so quickly.

Because we had decided to go into business together, it made sense to use the name of the web site that I had developed over six years ago for the name of the business.  I remember that when I first developed the web site, a journal for Jeff and my travels around the world, my Mother said that the name sounded like a travel agency.  She wasn’t quite right, but she wasn’t too far off.  And here we are today, Twin Travels, helping people learn about the outdoor environment and basic survival skills in exotic destinations.

The idea was something that I began playing with in my mind while working at IBM.  I always imagined that there could be something I could do that I would truly enjoy – something outside of the I/T industry.  The thought continued to cross my mind over the next few years but it wasn’t until I returned to work at IBM after an eight-month leave of absence traveling through Europe that I decided I had had enough of IBM.  It was time for a change.  I enrolled in the 11-month MBA program at CU Denver and began taking my idea a little more seriously.  Thanks to my Visionary Leadership class, I was given the opportunity to really consider how my idea would work.  I had just eight weeks to put it down on paper.

With the plan in hand, I began to work toward my goal.  I joined the Peace Corps in Latin America only a month after graduating with my MBA.  While doing business development in the Peace Corps, I was able to learn some of the ins and outs of their business practices, a deep understanding of their culture, and, finally, the Spanish language.  I also gained some invaluable contacts along the way that were vital building blocks towards my success.

The Peace Corps was a truly amazing experience.  However, I felt that I needed some “street creds” if I really wanted to make my plan work. Upon returning from the Peace Corps, I took a couple of classes with a company called BOSS (Boulder Outdoor Survival School) where I learned from one of the most successful companies (in the outdoor survival skills business) exactly how to teach survival skills to customers.

I was lucky enough to land a job with BOSS, helping with their marketing (along with a little finance).  This position gave me some real insight on how they were able to turn a profit and run such a successful business.  I also made some invaluable contacts.  My two current employees also worked at BOSS. I recognized the two as some of the up-and-coming guides in the industry.  They weren’t just doing this stuff for a paycheck.  They truly enjoyed teaching people, loved working in the outdoors, and had a deep respect for the environment. It wasn’t too difficult to talk a couple of guys into joining a new venture doing the same type of work, only in exotic places.

After a couple of years of experience at BOSS, I decided it was time to make my move.  I dedicated the following year into doing all the research necessary to find out if (and how) my idea would work.  I researched the market, looked into doing business in a foreign country, and redeveloped the business plan I had written back in grad school.

I’m glad to be able to take a look around me now, then look back and say that all of that hard work paid off.

Getting back to reality, we’ve arrived in Costa Rica with a smooth landing in its capital city, San Jose.  During the trip, we discussed much of the plans for the preparation for our second class, much of this discussion involving the lessons that we learned from our first class.  We discussed that we needed to focus more on the needs and wants of our customers.

Some customers were pleased with the lack of amenities provided by the class, some suggesting that we take away more amenities; while others suggested that we provide more comfort during the course.  We considered this feedback and decided that we should stick with the values and mission set by our company and ourselves.

Our first class tried to impress our company values upon the customer. We wanted the group of twelve students, coming from various countries around the world (including North America, Europe and Australia), to learn from each other, as well as learn from the culture in which they were immersed thereby coming away with a better understanding of cultures around the world.  We focused on teaching them the simple lifestyle of the indigenous peoples living on the coast, from such simplicities as food gathering and preparation to more esoteric knowledge like ghost stories, rituals, and games.  We taught them how this basic, isolated lifestyle helps the environment by keeping out the consumer-hungry lifestyle that many are accustomed to in Western societies.

We were able to attract such a variety of clients by marketing to people around the world. With contacts in different places, we were able to get people from many different places on board.  With a greatly reduced price to attract initial customers, it wasn’t long before we had a waiting list for subsequent courses.

After piling into a local bus and crawling west along the “highway” to the Caribbean coast and onto some dirt roads along the coast, we finally arrive at our destination.  As always, it is absolutely beautiful.  It truly is a “Rich Coast” with endless sandy beaches, warm waves breaking on the shore, and, with the distance we put between ourselves and civilization as we know it, it seems like we’ve arrived at a different world. We greet the local villagers and begin to set up our camp at a respectable distance from them.  After setting up the huts, we decide that its best to get some rest so that we are all ready to plan our next class by setting things up and organizing with the villagers.

So, you’ve crafted a vision that’s both inspiring and aligned with your core values and purpose. What’s next? Spotting and navigating contradictions in your plan. Stick around as we learn to embrace and address these plot twists in your story!


Embracing and Addressing Plot Twists

Ahoy, planner! You’ve charted out a vision that’s as bright as the North Star. But what about the clouds that might obscure it? That’s where contradictions come into play. These are the plot twists in your story, the elements that don’t quite align with your values, vision, or both. Identifying and addressing these contradictions is crucial for keeping your plan realistic and adaptable.

  1. Expertise vs. Aspiration: Perhaps your vision involves scaling the corporate ladder or launching a groundbreaking startup, but your current skills don’t match up. Acknowledge these gaps as contradictions between where you are and where you want to be.
  2. Networking vs. Current Contacts: Your vision might require a robust network of industry insiders, but maybe your current Rolodex is a bit sparse. Recognizing this discrepancy is the first step to bridging the gap.
  3. Funding vs. Financial Reality: Maybe your dream requires capital that currently seems like a distant dream. Understanding this financial contradiction helps in planning realistic steps towards your goal.
  4. Passion vs. Profession: Are you chasing a career that truly lights your fire, or are you stuck in the “just another paycheck” mindset? This contradiction is vital to unravel for a fulfilling journey.
  5. Quality of Life vs. Workload: Dreaming of a balanced life while envisioning an 80-hour workweek? Time to address the contradiction between your ideal lifestyle and the demands of your ambition.
  6. Identity as a Businessperson: You may envision leading an enterprise, but does the nitty-gritty of business excite you, or does it feel alien? Aligning your self-perception with your entrepreneurial dreams is crucial.

Next, we’ll dive into setting objectives, strategies, and tactics – the nuts and bolts that hold your five-year plan together. Stay tuned as we turn those lofty visions and identified contradictions into actionable steps!

Objectives, Strategies and Tactics

Turning Dreams into Reality

You’ve envisioned a future, embraced contradictions, and now it’s time to lay the bricks on the path to your dream castle. This is where objectives, strategies, and tactics come into play – think of them as your five-year plan’s GPS, guiding you turn by turn towards your destination.

  1. Objectives: These are your big-picture goals, the main achievements you aim to unlock in the next five years. They should be ambitious yet achievable, like getting a specific job or launching your dream business. Keep them clear, time-bound, and directly tied to your vision.
  2. Strategies: If objectives are your destinations, strategies are your routes. They outline how you’ll achieve each objective. This might include gaining certain skills, building networks, or securing funding. Strategies require a good understanding of what’s needed to reach your objectives and should be flexible enough to adapt as you progress.
  3. Tactics: The most detailed level of your plan, tactics are the specific actions you’ll take to follow your strategies. This could be enrolling in a course, attending networking events, or saving a set amount of money each month. Tactics should be concrete, measurable, and deadline-driven.

Let’s take an example:

Objective: “Start my outdoor education/adventure business by April 2008.”

  • Strategy: Learn about the outdoor adventure business.
  • Tactics: Research offerings, read specific books, attend related conferences.

By defining these elements, you transform your vision from a nebulous dream into a series of actionable steps. And remember, while it’s good to be as specific as possible, the real world loves throwing curveballs. So, stay flexible and be ready to adapt your strategies and tactics as you go.

And with that, you’re equipped with the knowledge to create a five-year plan that’s both visionary and practical. Go forth, plot your course, and may the winds of fortune sail you swiftly towards your dreams!

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About the Author Jason Ryer

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