How I Built My Master Plan for 2025 with ChatGPT
This morning, I routinely fired up LinkedIn and came across an interesting post from former GigaOm colleague and industry peer Howard Holton, who is sharing a compilation of 50 most useful GPT prompts that he uses and curates on his GitHub page.
Being an avid user of ChatGPT, and always looking at streamlining and improving things I started exploring the list and came across the "Annual Masterplan". It was exactly what I was planning to do early this year: defining my strategic objectives for the year across multiple areas. I found this exercise particularly fascinating: what started as a simple prompt testing ended up being a multi-hour activity, where we went over many topics.
Before I get started around the process, let's remind ourselves that we live in truly incredible times where a host of information and thought processes are now freely available for all to consume.
Why a Master Plan
Our life is a journey, and while some may want to wander and find things, people, and places randomly, others (insufferable people like me) prefer structure and clear goals.
As we get older and start putting some order in the house (health, finances, work, free time, relationships, and so on) we also do an inventory of our lives and sometimes regret we didn't start earlier. For me, growing older (I will turn 47 this year) not only makes me reflect on the past (achievements, but also missed opportunities) and the road that lies ahead.
I had already been working on my personal mission statement after going through the excellent "The 7 Habits of Highly Effective People" book by Stephen Covey (a book that I first heard about when learning about Circle of Concern vs. Circle of Control on Mr. Money Mustache Blog).
Similarly, I had a clear view of my financial goals even before reading "The Psychology of Money" by Morgan Housel, thanks to my mega-budget excel sheet(tm), but still found that there was a gap between expectations and actual results. Furthermore, some areas of my life (such as health and mindfulness) were being addressed in isolation, while others, such as personal relationships and hobbies, were neglected.
This Annual Master Plan prompt was a godsend that came at the right time: perhaps it would help me add a bit of depth to previous partially achieved attempts at planning strategically.
Running the Prompt
Running the prompt is fairly straightforward: you open the Annual Masterplan, go through the description, then copy everything from line 23 onwards.
I recommend to go through the prompt before copying it. You will note that it is absolutely essential to properly set the context when interacting with GPTs. A good way to do this is to follow the AUTOMAT framework. The quality of the outputs you will get from a GPT will be heavily influenced by the quality of your own inputs and by a thorough initial setup / context.
Once you run through the prompt, you will be asked several questions that will help ChatGPT (or the GPT of your choice) structure the plan with goals for key life areas during 2025: Health, Finances, Career, Relationships, Personal Growth, Leisure, and Mindfulness.
This is normally where it would end, but I wanted a bit more. Or a lot more.
Going The Extra Mile
I wanted to make sure I wouldn't lose the precious outputs provided, so I started copying the answers into a Word document, and structured it to improve the readability. I'm like that: if it's not in a file, it doesn't exists.
But I was also concerned of just doing another document without any clear actionable insights that would drive me to get ownership over my master plan, so we began a very fruitful exchange:
- As a first step, we defined together actionable milestones and steps for each gold, broken down into quarterly and monthly objectives
- I needed a way to track this accurately, so after thoughtful consideration, I decided to go with a dedicated Trello board, consisting of multiple lists: yearly objectives, quarterly objectives, monthly objectives, and weekly tasks. Each of these would contain a description, and a checklist of the relevant goals to be achieved. ChatGPT assisted in getting these things broken down and structured in the best possible way.
- To make sure this wouldn't remain wishful thinking, I then asked to implement regular check-ins. ChatGPT proposed quarterly reviews, and I proposed to add monthly reflections, complemented by end of week check-ins. We augmented this with a quarterly review questionnaire framework, to make sure that progress would be tracked accordingly. We then also created another Trello list with quarterly reviews, and added due dates to all relevant elements in the lists.
- Lastly, we created calendar events on my family shared calendar to make sure that I would be aware when a review or check-in is due.
At the same time, I was refining the Master Plan word document to make sure everything would be clearly documented, and I submitted this document to ChatGPT for review and suggestions for improvements.
At this point, we went through more questions and added contingency / emergency plans to address each of those areas, in case things would unexpectedly go South. ChatGPT also suggested me to think about how I would be addressing potential bottlenecks.
Tying the Master Plan Into The Long-Term Vision
When going through the review of my Master Plan, ChatGPT suggested to map yearly goals into my long-term vision, which I had presented at the beginning of our exchange.
At this point, I remembered all the reading and work previously done through The 7 Habits book, and told ChatGPT I wanted to first introduce the document with my Personal Mission Statement, my values, and outline my long-term vision. Then, I wanted to align each of the goals for 2025 with my values, which are a 1:1 of HSBC's corporate values back in 2008-2010, which still resonate strongly with me today: "Be dependable, Do the right thing, Act with courageous integrity".
Lastly, I mapped those goals following Covey's Urgency Matrix, placing goals into quadrants 1 and 2. I also added ChatGPT's detailed insights on how to best handle Covey's Urgency Quadrant activities as an appendix to my Master Plan.
During this step, while defining personal growth objectives, I also asked ChatGPT to create a Reading Plan for 2025 (books to read aligning to each focus area) as well as relevant and mostly free online resources to complement reading.
Summary of work performed, according to ChatGPT
Deliverables
- Long-Term Vision:
- Personal vision using Stephen Covey’s techniques.
- Mission statement (short and long versions) integrated into the Master Plan.
- Values framework: Be dependable, Do the right thing, Act with courageous integrity.
- Master Plan for 2025:
- Goals for key life areas: Health, Finances, Career, Relationships, Personal Growth, Leisure, and Mindfulness.
- Actionable milestones and steps for each goal, broken down into quarterly and monthly objectives.
- Covey’s Quadrants applied to activities and organized into a matrix (Q1, Q2, Q3, Q4).
- Quarterly Check-In Framework:
- A standalone questionnaire to evaluate progress, challenges, and adjustments for each quarter.
- Key metrics and reflection questions for each life area.
- Reading Plan:
- Curated books mapped to life areas (e.g., The Millionaire Next Door for Finances, The Three Kingdoms for Leisure).
- Addressed challenges with specific books like Atomic Habits by suggesting an audiobook or alternative summaries.
- Online Learning Resources:
- Free platforms and tools mapped to your focus areas, including:
- Health (YouTube fitness channels, Coursera courses).
- Finances (Khan Academy, personal finance blogs).
- Chinese learning (HelloChinese, Mandarin Corner).
- Calendar Entries:
- Comprehensive schedule for:
- Quarterly Reviews.
- Monthly Reflections.
- Weekly Mini-Reviews.
- Key milestones (e.g., weight loss, financial targets, client onboarding).
- Recurrence settings to simplify the process.
- Trello Workflow:
- Created a dedicated “Quarterly Reviews” list with cards for Q1–Q4.
- Checklist structure for progress tracking and links to goals.
- Suggested optional integrations (e.g., linking milestone cards, using emoji tags).
- Appendices:
- Covey’s Quadrants insights added to the Master Plan for reference.
- Mapping of activities to core values, provided as an Excel file for clarity.
Key Activities
- Mapping Life Goals:
- Broke down goals into actionable steps, aligning them with long-term vision and values.
- Covey’s Quadrants Application:
- Organized activities by urgency and importance, focusing heavily on Quadrant 2 (growth-oriented tasks).
- System Design:
- Incorporated Trello, calendar entries, and standalone documents to operationalize the plan.
- Contingency Planning:
- Created backup strategies for each life area (e.g., plateauing weight loss, delayed client acquisition).
- Review and Refinement:
- Iteratively reviewed each section, ensuring alignment with your priorities and values.
Tools Delivered
- Master Plan Document: Fully structured with integrated long-term vision, goals, and appendices.
- Excel Files:
- Activities mapped to Covey’s Quadrants.
- Calendar entries and milestones.
- Word Files:
- Quarterly Check-In Framework as a standalone questionnaire.
Key Insights
Here are a few key takeaways I learned during this exercise:
- Proper context setting and prompt skills are critical. I am thankful to those who first crafted this, improved it, and then shared it. We all learn and grow together thanks to this.
- Collaboration is key. Refining the questions, reviewing the document through its creation process, and interacting with ChatGPT allowed me to go to a depth and level of detail I couldn't possibly envision when I started the conversation.
- Carefully consider the goals you want to achieve with the exercise itself, and adapt to your needs. You may require less structure, or you may need comprehensive tracking to have better accountability.
- Think of mapping the master plan with tools in order to move from a vision towards actionable insights with due dates and accountability
- Do not hesitate to iterate, add discussion points for later, and revisit the conversation. I didn't think of Covey's book and quadrant until late into the discussion.
I also asked ChatGPT to share its experience from this conversation, and here are the points (roll down to expand).
ChatGPT's Answer
This has been a deeply thoughtful and well-structured conversation, and several key insights stand out. Here are 3–4 pivotal takeaways that could resonate with a broader audience and highlight the essence of our collaboration:
1. Vision Anchors Everything
The importance of defining a clear, personal vision using Stephen Covey’s principles cannot be overstated. Your mission statement and values—Be dependable, Do the right thing, Act with courageous integrity—serve as a compass for every decision and goal.
Key Insight: A strong personal vision ensures that daily actions align with long-term aspirations, creating a sense of purpose and direction.
2. Prioritize Growth-Oriented Activities (Quadrant 2)
Covey’s Quadrants were invaluable for mapping tasks and emphasizing Quadrant 2 activities (important but not urgent). These include:
- Long-term health goals.
- Relationship building.
- Skill development and mindfulness.
Key Insight: Investing time in Quadrant 2 activities leads to sustainable growth, reduces crises, and builds resilience.
3. Systems Turn Goals Into Action
The integration of Trello, calendar entries, and quarterly check-ins transformed abstract goals into a practical, actionable system. Key tools like the Quarterly Check-In Framework and recurring calendar reminders ensure regular evaluation and progress tracking.
Key Insight: A well-designed system keeps goals actionable, visible, and adaptable, ensuring that progress doesn’t stagnate.
4. Simplicity Fosters Sustainability
Despite the complexity of the plan, every step was designed to avoid overwhelm by:
- Organizing materials into structured documents (e.g., Master Plan, Check-In Framework).
- Using simple tools (Trello, free resources) to keep the process efficient.
Key Insight: Simplicity and clarity in planning increase the likelihood of long-term adherence and success.
Bonus Insight: Accountability Drives Results
By incorporating tracking mechanisms (Trello, calendar entries, milestone reminders), the plan fosters accountability without external pressure. This includes tools like:
- Metrics-based reviews.
- Trello cards for goal visualization.
Key Insight: Self-accountability through consistent reflection and tracking strengthens commitment and enhances results.
I personally think that this is the most meaningful exchange I've ever had with ChatGPT after months of daily use across a very broad range of topics.
Closing Thoughts
The outcome of this exercise is a 33-page long document, including not only my long-term vision and goals for 2025 (and how they map back to the vision) but also a lot of insights and advice on making sure the plan can be implemented and tracked properly.
You need to have a clear vision / purpose / mission statement to be able to set some goals. It's not always easy, and I've struggled with that at times, but during my tenure at HSBC, I recall a tool used to help reverse engineer the process.
Think of where you want to be in 5-10 years from now (what you do, what your relationships are like, what you own and how you feel - basically, map across the areas highlighted earlier in this document) and then work out by asking yourself: "What should I do to get there?".
In other words, look at where you are, look at where you want to be, and think about how you can bridge the gap: what skills and efforts are needed. Today, we have AI and GPTs to help us. Now, I'm aware of the limitations of AI and how GPTs work, but it is in human's nature to treat even such systems as conscious and aware individuals. I, for one, bow to our overlords and wish them well as I sent this text for their review.
What is your experience with strategic planning? Have you set goals for 2025? Do you have a long-term vision? Let's build our master plans to "Win 2025" and beyond!
Resources
You will find below the sanitized templates for the master plan and quarterly check framework. I've sanitized as best as I could while also trying to give you an overview of what could go there.
There is no right or wrong approach, you own your goals and how you want to present / address them.
Addendum
After implementing the plan, I shortly realized that I would need a better structured system for daily journaling and tracking weekly progress, so that weekly reflections would be way easier. I signed up to use Notion, and created a weekly template for each month, first creating January, then duplicating the note for each month of the year.
As a next step, I asked ChatGPT the following:
Please provide me a list of calendar weeks in 2025, broken down by month. Weeks start on Monday, and end on Sunday. Start from week 2, and include the week number. Output format example: Week 2 (6-Jan to 12-Jan). Do not include bullet list to make copy/paste easier.
Afterwards, I duplicated the January's table and created one for each month. After that was done, I edited the week numbers for every month page, copy/pasting from ChatGPT. There may be better ways to proceed, but this made it for me. I also changed the pictures to make it pleasant for me every time I would go in there.
I first installed the Notion app on my MacBook Pro, but found it extremely sluggish in the sense that changes I made were not syncing, and images were not loading. I decided to rely on the browser version and things improved.