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5 Year Plan Example Essays Compare

How to Create Your Five-Year Master Plan

Two weeks ago, I wrote this article here: The Most Valuable Strategy to Apply to Anything You Do. I received a lot of positive feedback from hundreds of you, many who privately messaged me to ask for specifics on what the plan looks like. Some of you also asked that I provide my plan. Initially, I was hesitant (hence the several weeks of waiting).

Then, I decided: What am I afraid of sharing with the rest of the world? My plan is not the secret Coca-Cola formula. Since I’m such a big believer in speaking our dreams over our life, so that they become our reality, I knew that I had to follow my own advice.

I was overwhelmed with the positive response and demand so I decided to share all of it with you. I’ll list the step-by-step details of what I recommend first, then, at the bottom of the email, I’ll list all of my specific information for each step, as well as my plan.

Understand, my plan is rooted in the core values I strive to live each day. I’m so passionate about this subject, I’m writing a book on Values. I hope you will build your life on a values structure that is true to who you are.

These values, along with this plan, have given me the clarity and direction I need to achieve anything I set my mind to in life. I have every confidence and faith the same is possible for you.

You can choose to make this plan as inclusive or focused as you want. I chose to include all the things that affect my life: Family, Health, Financial, Personal Development, Faith Life, Job, Writing, Coaching, Fun, Responsibilities, etc. I like doing an all-inclusive approach, because our personal lives affect our professional lives, as well as our personal ambitions. Here you go!

1. Start Writing

Spend Day One or Week One writing. Don’t get caught up in thinking — especially not over-thinking!. The best way to begin is to do a basic “SWOT” (Strengths, Weaknesses, Opportunities and Threats) analysis. I’ve listed my strengths at the bottom of this article, but I did all four (just chose not to list all of them for the purpose of time).

Don’t hesitate, don’t question yourself. JUST. START. WRITING! As Sean Connery’s character, William Forrester, says in the movie Finding Forrester:

“The first key to writing… is to write. Not to think.”

If you don’t know your strengths or weaknesses, turn to 3–4 of the closest people in your life who will offer you honest, objective information. You have to get objective, real information, otherwise, you’re wasting your time. Write all these things down. Know what you’re good at and what you’re not good at. I am a huge proponent of concentrating big-timeyour strengths.

You also need to know what opportunities you have in front of you, so you can always be on the look out, and things that threaten your time, productivity and more.

2. List out the things that motivate you

What drives you? What inspires you and lights a fire inside of you? List those things. This is a very simple exercise. The things that you love likely dominate your subconscious thoughts and maybe even your conscious thoughts. Start writing these things down. Then, determine how much you know about these things, and which of these things you have legitimate skills, knowledge and experience in. Speaking of which…

3. List your knowledge, skills and experience

What do you know? What have you actually done? There’s a very big difference between what you’ve done, versus where you are currently and what you want to do. The prime example of this is, I want to be a successful author. I will soon publish my first book. So, I’m extremely close to that dream becoming a reality.

My dream is also to be an entrepreneur who writes for a living and coaches business clients. But the core of my professional experience has been as a business consultant and program manager. The moral of the story: I’m in transition. Maybe you are too.

You may want to be the curator at the Metropolitan Museum of Art someday, but perhaps your professional experience or education is in marketing. No problem, but it’s time to start working on that dream. It’s possible you’ve been grinding on the side for several years, volunteering at an art museum while becoming an expert in all genres of art.

And you now want to make your move. Pay attention first to the experience you have. Trust me, there’s a method to my madness…

4. Transferable Skills

If you’re looking to make a career transition or to pursue something you really want, then you’re going to need to list out your transferable skills. Look at your knowledge, skills and experience. If you can do this yourself, wonderful, if not, then ask one of the 3–4 trusted advisors the following: What skills do I have that can transfer over to what I really want to do?

What skills can be transferred over to anything I want? This is of enormous importance to know.

The Plan

Ah, the plan! I chose to break mine out by High-Level and Ground-Level view. Since this is a five-year plan, it’s obviously going to have some big picture plans, in addition to plans very focused on achieving by the week or month. As I wrote last week:

Short-term thinking and strategy is always imperative. But if it is not accompanied by a big-picture view that can recognize change, we’re in trouble.

What I recommend you do once you have populated your plan is to manage it in a productivity management tool with tasks. You’ll see below that I have nine things listed per my High-level and Ground-level plan. But my tasks number in the thousands on an annual basis. Each week, I’m taking measured steps to achieve the goals I have listed in my plan.

The way to track your progress and create tasks is to use tools like Microsoft Outlook, Trello, OneNote, Evernote or whatever you desire. Everything has moved electronic, so only having this written by hand is a big mistake! I’d encourage you to take the therapeutic time to write it out by hand. But make sure you have this in an electronic document to track your tasks.

I personally use Microsoft Outlook Tasks. This is a great way to go. It works or me but it may not work for you. So find what does work. I got the idea for using this from the Getting Things Done methodology created by David Allen. You may be familiar with this. They have a free trial on their site and you can find additional information on YouTube and Google.

You have to hold yourself accountable. Technology is a great way to do this, with built-in reminders and daily, weekly, monthly and annual tasks to make sure you’re doing what you said you would. If you don’t do this, then a plan is worth nothing. A plan can be a living, breathing document if you actively follow it.

And last, but not least, know this most important principle:

Plans change.

Your plan will change too. Your tasks will change. Chances are, your overarching objective should remain the same. Maybe, that too will change. But I’d urge you to be much slower to change that. Don’t just create something in a few days. Give it deep, meditative thought. Get to the core of who you really are. Then, go forth in confidence and live your dream.

My Five-Year Plan (Who I want to be and What I want in my life in 5 Years):


  1. A devoted follower of God who is living his life with incredible confidence, energy and as little sin as humanly possible
  2. A loving wife, children and an amazing family life
  3. Be very healthy and live with vitality, vim and vigor!
  4. Learn something new every day; always finding creative time and inspirational time
  5. Coach basketball at the high school level- hopefully as a head coach but if not helping out; Coach my son’s youth team
  6. Be a bestselling author, writer and media personality- be in control of my own personal worldly destiny, not at the whim of others
  7. A nationally known voice on the message of values, empowerment, faith, love and personal development
  8. Reach a very large audience with my message
  9. Live in a place where I truly love living each day — New York, Charleston or somewhere close to my family where I am happy and embrace my community


  1. Attend church regularly, serving actively in my church, community and truly living God’s word and what I write/preach
  2. With God’s grace, we have hopefully received two more beautiful, healthy children
  3. Eat well each day; work out and take care of my body; genuinely excited for each new day that comes
  4. Continuously improve my writing; public speaking; Living an open-minded life and planning time into my day for inspirational activity and creative time to do what I love
  5. Coaching and teaching my son the game of basketball and what makes someone great; Coaching for a high school team
  6. I have published several books, actively marketed, advertised them and found the right people to help make them successful. Active speaker and someone who has pursued media opportunities on radio, digital and TV to grow into a leading voice
  7. Using my platform as a writer, speaker and TV/Radio/Podcast presence, I am a recognized subject matter expert and esteemed, respected voice on the topics
  8. I have taken proactive steps to build my personal/professional network and meet people of influence that have actively helped to amplify my voice and lead me to larger audiences and opportunities. I have created these opportunities myself using all of the mediums at my disposal to bring high-quality, rich content to the world and getting the message out effectively and efficiently
  9. I have relocated and arrived at a location that I love. I am living the dream and I’m satisfied with the community and place where I am. My family is happy and we have embraced our surroundings and IDEALLY have family and a great community to support us


  1. Business and Creative Writing
  2. Editing
  3. Emotional Intelligence
  4. Teaching
  5. Personal Development
  6. Career Development
  7. Catholic/Christian Faith
  8. New Testament knowledge
  9. Athletic
  10. Asking Questions
  11. Networking
  12. Asking for Help from Others
  13. Listening, Conversations
  14. Self-Awareness
  15. Planning
  16. Blogging
  17. Time Management
  18. Scoping and seeing Big Picture
  19. General Sports Knowledge
  20. Basketball
  21. Gap Analysis
  22. Interviewing People
  23. Music knowledge
  24. Current events and news
  25. Funny
  26. Career Advisory and Development
  27. Speaking
  28. SEO
  29. WordPress
  30. Content Management and Content Marketing
  31. Coaching
  32. Leadership
  33. Social Media
  34. Generating ideas for content
  35. Program Management
  36. Business Analysis for topics that interest me

Knowledge and Experience:

  1. Liberal Arts degree in Political Science
  2. Master’s degree in Public Administration
  3. Financial Market Research
  4. Inside Sales Calls
  5. Marketing
  6. Management Consulting: Business Process Improvement, Content creation, Change Management, Project Management, Program Management, Business Analysis, Performance Improvement,
  7. PMO Leadership, Strategic Recommendations, Governance/Structure, Initiating a Program, Portfolio Management
  8. Presenting Analysis and Strategic findings
  9. Academic Research
  10. Facilities Management
  11. Basketball Coaching
  12. Resume Writing
  13. Personal Development Writing
  14. Sports Writing
  15. Catholic/Christian Writing
  16. Learning and Development
  17. Blogging, Content Creation, Internal Communications

What Drives Me:

  1. My Family- Wife, Son and Birth Family
  2. Coaching Basketball and becoming a part of a basketball/school community
  3. Coaching my son and my future children; working with them to help them develop their mental and physical strengths as athletes
  4. Reaching Self-Actualization- living out my dreams and becoming the man I planned and dreamed I would be
  5. Eliminating the negatives and things that hold me back
  6. Living my life on my terms not beholden or on others’ time
  7. Helping Others and Sharing my Knowledge and Gifts to make the lives of others better and richer
  8. Faith
  9. Working with people who have positive mindset
  10. Empowerment messages, Self-Improvement, Improving our lot in life, Growth
  11. Communicating with others
  12. Publishing a Book and then more books; The mindset of perseverance to “Keep Going” with my writing
  13. Receiving recognition for doing the work I am meant to do
  14. Seeing God’s love and work in the world
  15. Making children and young people happy
  16. Staying fit and active
  17. Growing my personal brand of Faith, Empowerment, Personal Development, Emotional Intelligence and stimulating thought
  18. Creating valuable content that people love
  19. Traveling around the country and world
  20. Road Trips

Transferrable Skills:

  1. Business and Creative Writing
  2. SEO, Content Marketing, Content Creation
  3. Thought Leadership and Ideation
  4. Creating a Charter or Contract of agreement for what to deliver to an organization
  5. Developing PowerPoint presentations, graphics in Canva, writing blog posts
  6. Internal Communications, Website Content, Editing, Promotion and Advertising through Writing
  7. Resume Creation
  8. Business Coaching
  9. Sports Coaching
  10. Editing
  11. Public Speaking/Presentation Skills
  12. Managing a Program — Governance, Leadership, Structure, Initiating/Stand-up, Planning stages
  13. Executive-Level status updates
  14. Demonstrating Value by Business Analysis and succinct analysis
  15. Program Evaluation
  16. Managing Employees
  17. Connecting with People to understand what they really want and need
  18. Developing pitches for speaking/writing opportunities

Live Boldly!

If you enjoyed reading this piece, please be so kind as to share and recommend to others. Also, please consider following me here on Medium! My upcoming book on Values is due out this Spring. Contact me via my website here and subscribe for awesome updates if you feel inclined! Like my Facebook writer’s page here!

I’m so grateful for all of your support as I continue to dream and live out my journey. I fully support yours. Keep Going!

Franklin Roosevelt and Josef Stalin were both key players in politics during the inter-war period. Though in drastically different countries; one a democracy in the western world, and one a communist totalitarian state in the east, their plans of action to pick their countries up after different defeats do have some similarities. Granted their actions also have drastic differences, parallels can also be drawn between the New Deal and the Five Year plan.

Franklin Roosevelt was first elected in 1933. He set in place The New Deal, which revolutionized social works and programs for the average people of America. With the Alphabet agencies he was able to provide jobs, guarantee workers rights and minimum wage. He also controversially subsidized farmers into producing less food, to raise food prices on the market. Also, Roosevelt believed in financial reform, and brought people's confidence back concerning banking and currency. Roosevelt welcomed critics and used statistics as an offensive.

He did so much for the people that he was re-elected three consecutive times and died in office.

Meanwhile, in communist Russia Stalin had taken the reigns of the Bolshevik party, having exiled Trotsky completely from Russia. Stalin set in place the first five-year plan, with GOSPLAN, the national planning agency in control of everything. He abolished the NEP and banned small industry, while rapidly trying to collectivize farms, believing they would be far more efficient as larger industrially run machines. He encouraged many peasants to move to the cities and become involved in the industrial revolution taking part. Stakhanovism became a prominent ideology, and in the footsteps of great achiever Stakhanov, many men tried very hard to beat quotas to receive raises, better housing and special treatment. Another facet of the five-year plan was the purges. Stalin purged the government, the army and the...