Life Overview: some deeper dives to examine your life
My 30-second blurb if you’re new here
You’re reading Narasimhan’s Persimmons, a Substack on life design, personal development, and the pursuit of world-class performance (in the midst of the daily chaos we all experience). I’m Madhu Narasimhan. Join me in exploring foundational frameworks and strategies for living a healthy, joyful, meaningful—and ultimately, good—life. In this Substack, we’ll cover all things life (beyond work), from meditation to building community in a new city to finding the best teahouses in the world.
I also write Let Us Reach, a newsletter-blog for thinkers and doers, movers and shakers. There, I share my work and professional/intellectual interests, including entrepreneurship & technology, law, politics & public policy, global affairs, and grassroots service. I’d love to have you as a reader there as well.
Life Overview: some deeper dives to examine your life
Last time, we looked at the daily fundamentals for conducting a Life Overview:
Calendar
Template (i.e., ideal) schedule, an actual schedule for the day (derived from the template), and to-do list(s)
Journal
Trackers for various life categories
Raw notes, second brain, and file storage
Those are the daily tools.
Now, we turn to some deeper dives you can do on a monthly, quarterly, or annual basis to examine the state of your life—where you’ve been, where you’re at, and where you want to go.
Start by looking back.
The act of looking back and reviewing your life—ideally as soon as a designated time period (e.g., a month or a quarter) is over, such that you can accurately capture your sentiments and lessons in real-time—is critical for figuring out how to shape your life moving forward. (If you review the month of April only in November, your sentiments may not be as accurate or complete as they could have been).
As I mentioned in my last essay, I use my Journal doc to review each week, month, [sometimes the quarter], and the year. I scroll through my Journal, look at each day, and compile the highlights of Monday-Sunday into a summary of the week, then the highlights from a few weeks into a summary of the month, then the highlights from January-December into a summary of the year. Here is a partially filled-out annual journal Google Doc template, so you can visualize this nested approach.
At the end of the year, I also look back at my category-based Airtable trackers (e.g., exercise logs, books I read, places I traveled to) and my digital photo album to get a comprehensive view of what the year was like. I might also answer some prompts (e.g., “What was your biggest win this year? Biggest challenge and what you learned from it? What’s one thing you’ll carry into next year, and what’s one thing you’re going to drop?).
These reviews are all stored in the Journal. At any point, I can pull up the Journal doc for a given year, read the annual review, and get a quick sense of what my life was like during that time period. (And if I’m interested in anything more granular than that, I can always read through the logs of specific days too).
AN EXERCISE:
Do you have a Journal doc or another review mechanism set up? Additionally, what other materials—e.g., category-specific trackers, photos, other files, or physical possessions—can give you a sense of how your year went?
Next, write out a “Life doc.”
Ok, you’ve reviewed the past. Now, as you figure out how to best live in the present and look forward into the future as well, you’ll want to set up a Life doc.
AN EXERCISE:
Open up a document (I recommend doing this as a digital doc rather than a sheet of paper so that you can continue to easily edit the doc over time). Type out 3 headings:
Introductory Reminders
Mission/Purpose
Life Categories
At the moment, my Introductory Reminder is: “This life is a miraculous and beautiful thing. Cherish the limited time. Utilize it; live well.” Yours can be anything you’d like it to be—a simple reminder and preface for your Life doc, or something much more elaborate.
We then come to Mission/Purpose. This is your personal answer to the question, “What is your why?” In other words, what gives you meaning in life? Different folks will have differing opinions on whether life is endowed with inherent meaning (e.g., by a higher power, the universe, or even the norms of human society), but regardless of your position on that, most folks can probably agree that we each have some degree of choice in how we actually go about living—in what we make of our lives.
What do you seek out of your time on this earth? Reflect quietly on this. List these missions/purposes out in broad terms, in brief bullet points. And know that this isn’t set in stone; don’t be afraid to put some thoughts down for now and then continue revising over time. As you explore various pursuits, cultures and societies, and parts of yourself, your “why” will evolve and crystallize (and then perhaps evolve again) over time.
As a starting point, you might consider some of these:
Health (and the basic needs of life) — it all starts here; without this, you can’t really function
Happiness/well-being — underpinning all of our pursuits, isn’t this what we’re all really seeking? (Of course, one could argue that they are more interested in the welfare of others or in the Divine or in grieving lost loved ones, but even those pursuits are perhaps ways of finding personal fulfillment, ultimately. So maybe I’m sort of equating “happiness/well-being” here with a sense of fulfillment and flourishing).
…
Loved ones
Kindness, compassion, and connection more broadly — including with people/beings beyond those we love the most
Serving people/beings, your community, and the world
…
Living according to a code of ethics; being good — however you’ve chosen to define that, perhaps borrowing from the law, religion/spirituality, philosophy, or some other body of wisdom
Philosophical thinking — considering life’s big questions, like why we’re here, how to live well, or what we owe each other
If you’re a religious/spiritual person, then devotion to God or a path of spiritual enlightenment
…
Your work-related purposes — in the most idealistic terms, what are you hoping to contribute through your work? e.g., If you are a software engineer, are you seeking to create technology-based products that bring delight to people and make their lives easier? If you are a lawyer: are you hoping to help structure the rules of society such that “the arc of the moral universe…bends toward justice,” in the words of MLK?
Financial security and comfort — whether or not wealth creation is a driving sense of purpose for you, the reality is that human society is set up in such a way that financial security is required in order to obtain resources & services and live well. How important is the financial mission to you?
Time freedom — on the flip side, the pursuit of money often eats up 8+ hours of our day, 5+ days of our week, 48+ weeks of our year, and 40+ prime years of our lives. But time is actually the ultimate, nonrenewable resource of life. Hence, maximizing control of your time might be a critical mission to consider.
…
Curiosity, adventure, exploration of the world, life experiences, fun/enjoyment/pleasure/play
The pursuit of excellence across all categories of your life — through deliberate life design, personal development, visionary and strategic thinking, daily learning, and deliberate practice. If you’re reading this Substack, you’re likely interested in these things.
You’ll notice that there is some amount of overlap between the sense of Mission/Purpose I’ve outlined above and the Life Categories I noted in a previous essay on this Substack. That’s intentional. Ideally, you want your Life Categories (the areas and activities of your life that are significant to you) to flow naturally from your Mission/Purpose—and vice versa.
Hence, for your third heading on the Life doc, list out your Life Categories, ideally in tiers or priority order. (“Relationships” and “health & fitness” are probably going to be higher on the list than “shopping” or “digital life,” for example).
And that’s the Life doc. You now have a place where you can turn to and examine what it is you’re really trying to do with this life.
Next, write out your visions (AKA dreams) and specific goals.
Once you have your overarching Life doc, you can delve into your dreams and goals.
AN EXERCISE:
Just as you did with the Life doc, set up a “governing doc” for each of your life categories. (Yes, I’m obsessed with creating docs, but you can also do this using Notion boards, slide decks, or some other format that appeals to you, as long as it’s easily editable over time). In Google Drive, I have a root folder, plus a governing doc within that folder, for each of my life categories, from Travel to Finances to Relationships.
Once you’ve created folders and governing docs (and it’s fine if they’re empty up to this point) for each of your life categories, you can answer the following questions on each governing doc:
Why is this life category important to me? (e.g., “I care about health & fitness because my body is like a house that I’ll be living in for hopefully the next 70 years; I need to take good care of it. That will enable me to pursue the rest of my life with as much vitality as possible.”)
What are my core identities with respect to this life category? e.g., For health & fitness, those identities might be: “I am a healthy person. I am a physically fit person. I am a disciplined athlete.” When you ingrain an identity into your mindset, you become much more likely to follow habits in line with that identity. For example, if you believe yourself to be “a disciplined athlete”—even if you haven’t been historically—you will be more likely to show up to the gym or practice tennis when you reflect on that specific identity. If you believe yourself to be a “healthy person” and you remind yourself of that identity while you’re eating, you will be less likely to gorge on highly processed snacks.
What is my long-term, life-time vision in this category? Here’s a chance to dream big dreams! For example, for a category like reading, that might be: “I want to be super well-read and lean on literary wisdom, for myself and others, throughout my life.”
Based on that vision, what is my long-term, life-time goal? A goal provides more specific definition to your vision. Staying with the reading example from above: a goal in alignment with the aforementioned vision might be: “Read 2,500 of the greatest books ever written, across a mix of subjects/genres, authors, and time-and-place of writing. Take notes on those books, review notes & quotes regularly, and share on a blog.”
Then: what is my medium-term goal? This should flow naturally from your long-term/life-time vision and goal. I’d advise defining the “medium-term” as somewhere between 2 years and 10 years (e.g., what do I want out of my 30s?). Personally, I like to choose 5-year segments (e.g., age 30 to 34, age 35 to 39) because it’s a meaningful enough chunk of time to give you lots of space to grow into the person you want to be, but it’s also not so distant in the future that the medium-term goals start sounding exactly the same as your long-term/life-time goals. For the reading example from above, the medium-term goal, derived from the long-term goal, might be: “Read 250 books over the next 5 years. Work up to posting once a week on my book blog.”
Then: what is my short-term goal? I like defining this as one calendar year (e.g., 2024) or one age-based year (e.g., 32). (Those two options are essentially the same for me since I was born in January). :) If helpful, you can also write out any checkpoint goals (e.g., quarterly, monthly) along the way this year.
So, for reading, the short-term goal might be: “Read 50 books from varied sections of the Make Lists, Not War literature list in 2024, at a pace of approximately one book a week. Launch my blog in Q3 of this year, and then practice posting at least once a month for the rest of the year.”
Sometimes, separate from the short-term goals, I also like to add a couple of words, intentions, or key themes to inspire me throughout the year. For 2024, my words are: “joy” and “creative flourishing.”
Take a moment to really interrogate your long-term, medium-term, and short-term visions and goals. Is this really the dream/goal? Why? Are you being true to yourself? Are you being bold enough? (For further guidance, you can ask yourself questions like: What would I do if I knew I could not fail? What would be worth doing even if I knew I was going to ultimately fail? What would I do with my time if I received $10 million tomorrow? What would I be doing with my life if I knew I would die in 10 years? 5 years? In just 1 year?). While doing this interrogation exercise, remember to check for the following: your short-term goals should ideally flow from your medium-term goals, which should ideally flow from your long-term goals, which should ideally flow from the broader Mission/Purpose outlined in your Life doc. (But that isn’t to say that you can’t have different seasons and objectives in your life; you might have one approach to your 20s and another one entirely for your 70s. Just know that you’re thinking of partitioning by “season”).
What are my “anti-goals” (i.e., the costs that would make it such that my goals are no longer worth achieving)? I got this concept from Sahil Bloom, the personal development-focused content creator. You want to avoid a Pyrrhic victory, Sahil cautions. Example: let’s say your work-related goal is to be a CEO. Over a 10-year period, you rose up the ranks to become the CEO of your company. But in those 10 years, you spent very little time with your spouse and young children, you became extremely stressed and frequently grouchy, and everyone in the family—including you—is now feeling disconnected and unhappy because your path to becoming CEO required such a tremendous sacrifice. You also didn’t make time for exercise, and neglected to take care of your body along the way. Was it worth it? Or did this one goal of being CEO end up costing you in several other life categories? This type of scenario is why it’s worth taking a moment to define your anti-goals and limits upfront. So an anti-goal statement might look like: “If the path to being a CEO at this company is costing me my family and health, I will seriously reassess and consider a different career vision/goal after 12 months of being on this path.”
When you’re done running through these questions for each separate life category, you can also copy-and-paste to a Long-Term/Life-Time doc, a Medium-Term doc, and a Short-Term doc. (In lieu of a Short-Term doc, you can also just use the “Annual Preview” section of my Journal doc template; that’s where I put my annual goals at the beginning of each calendar year). This way, you can visualize your visions/goals not only in the governing doc of each separate life category, but also all together in timeline-oriented docs.
Next, think about your strategy to reach those visions and goals.
What is the grand strategy or plan you’re currently following, whether consciously or not? Everyone’s following some plan, even if they’re not conscious of what that plan is.
This is a concept I got from Ali Abdaal in one of his newsletter installments this year. The story he shared was about a content creator who had reached out to him. She told him that her goal was to grow her TikTok follower base and make meaningful income from her videos on the platform. She had been at it for a while, but wasn’t making any substantial progress with user growth. Ali asked her some questions and soon found out that she posts on TikTok inconsistently—just whenever she feels like it, and on whatever topics she feels like. Ali challenged her to think about what an ideal plan for her goal might look like: it would probably mean posting videos on a highly consistent schedule, analyzing who her audience is and what topics they’re most interested in, and tailoring her video production to match the audience’s interest. Ali told her: if your goal is to just post on TikTok as a hobby, then the plan you’re following at the moment is perfectly fine. But if your goal is to create an income-generating business (rather than a hobby) out of TikTok, then the plan you’re currently on (i.e., posting inconsistently, on miscellaneous topics)—even though it’s probably not a plan you ever consciously decided on—is not very effective.
The content creator now had the option to shift to a more consciously decided and effective strategy.
AN EXERCISE:
For each of your goals, what is the most effective and efficient plan/strategy? Are you already on that plan? Or have you consciously or subconsciously been following a different plan? Do you want to adjust course?
I will say this though: it’s okay to be on a circuitous plan, as long as you’ve had a chance to consciously decide on that plan. For example: You might be interested in being a climate nonprofit leader someday. But perhaps you have a family of five to provide for, and you need to achieve some level of financial security and save for your children’s college education first. Hence, you might be working as a software engineer right now. That may not be the most direct path to being the head of a climate nonprofit, but it achieves other high-priority goals and could build you the personal finances—and some skills—that could be useful for you to make a pivot to climate activism in a few years. (Nevertheless, I’d still suggest doing some climate work on the side in the meantime, so that you’re properly preparing for the eventual pivot!).
Next, prepare the right systems.
Visions, goals, and strategies mean nothing if you don’t have systems to help you take massive action. Let’s figure that out next.
AN EXERCISE:
Ask yourself the following:
What are the daily/weekly actions or habits I need to implement in order to make progress toward my goals? e.g., To get stronger and build muscle, you might want to lift weights at the gym 3x per week. To work toward leading a climate nonprofit someday, you might want to start volunteering on their advisory board once a week.
Can I break my plan into specific projects and tasks? To publish a book, you might need to develop a proposal, draft a few chapters, find a literary agent, sign a deal with a publishing house, deliver the first draft of your manuscript, and go through the editing process. Each of those projects might have sub-tasks associated with them as well. Detailing all of this and breaking the goal into bite-sized, well-sequenced chunks can save you from overwhelm and inertia.
How should I allocate my time on a daily/weekly basis? Figure out how much time to allocate to each activity, and then put it all together. Map out your ideal daily schedule and weekly schedule in order to make time for the different actions/habits, projects, and tasks that will lead you toward your goals. Make sure it all adds up to no more than 24 hours each day—with sleep factored in too! (I find this time allocation thing to be such a difficult task; there’s always too much that I want to get to! But it’s a critical thing to get right).
Then, plan each day’s actual schedule, with careful reference to your template daily schedule. Also, double check that you have all of your daily fundamental tools in place. For more on all this, check out my last essay.
Are there other systems that could be useful to me? This could include experimenting with new tech platforms or tools (I want to try Notion!), or perhaps delegating some of your projects to other people who want to help.
Execute, with consistency.
Every day, get started with each time slot that you’ve pre-allocated. Stay focused, and perform the activity with a joyful heart. You’re acting on your most important goals, after all! So relish the action and have fun.
A couple of tips here:
Let’s say you’re thinking about doing the thing versus skipping the thing (e.g., flossing your teeth because your long-term goal is to have really healthy teeth). Rather than thinking, “oh, it’s just one day—I’ll just skip flossing tonight,” think about the good outcome that would result if you did the thing every single day of your life versus the bad outcome that would result if you skipped the thing every single day of your life. In one case, you’d accomplish your goal of having really healthy, clean teeth. In the other case, you’d have highly gunky teeth, your gums might bleed when you floss only on occasion, and you might inadvertently invite other health problems as well. Visualizing the two outcomes, do you now prefer action or inaction?
But, if you miss a day, don’t beat yourself up; life can certainly get in the way of our best intentions. Just start again at the soonest possible juncture—ideally the next day, so that you’re not missing two days in a row. “Start again, start again” is a philosophy I’ve heard from a Buddhist practitioner I’m close with; the phrase reminds us to not dwell on our mistakes and to instead prepare ourselves for a fresh beginning.
Go through some miscellaneous reflections.
Post-execution, when you’re sitting down for your Life Overview deep-dives, you may want to consider some specific, additional questions for reflection.
AN EXERCISE:
Reflect on the following:
Am I actually making clear progress toward my goals? Am I getting “green checkmarks”?
Do these goals/visions still matter to me? What really matters to me right now (given the broader circumstances and context of my life)?
e.g., If you have a family member in the ICU, perhaps reading 4 books this month isn’t top-of-mind.
Am I achieving good balance across my different life categories? Alternatively, have I deliberately chosen to be “lopsided” in one category for this particular season of my life?
A deep check-in: What’s my overall level of happiness/well-being, joy, and positive energy? Is my current environment (including the place, the people around me, my work and activities, my lifestyle, etc.) well-tailored to the kind of life that I really want? Who or what’s giving me energy and propelling me forward? Who or what is draining my energy, stressing me out, or holding me back?
What are my strengths and differentiating factors? What are my weaknesses and areas for improvement?
It might be useful to keep a separate doc on these questions, so you can track your strengths and weaknesses over time. Anytime you get feedback from someone—positive or constructive—in a professional or personal setting, you can add to the doc and evaluate next steps.
Hone your strengths. You can certainly spend some time working on weaknesses (in the areas that are most important for your flourishing) and getting them to a more solid level, but it’s likely a better investment of your time to focus on your strengths and become world-class at those.
Any other reflection questions that are meaningful to you
I listened to a Tim Ferriss podcast episode recently, and he mentioned that he routinely collects thought-and-action-provoking questions. I loved that.
Do all of this once a month, or once a quarter—or at the very least, once a year.
The day and the week are time units of your life that should be focused on action and execution. But after each month or quarter—and certainly at year-end—you can sit down and do this set of deeper dives to examine your life. I’ll lay out the steps again, but I’ll word it in such a way that assumes that you’ve already done your first-round setup by now:
Start by looking back. Use your Journal and other materials, and consider how the month, quarter, or year went.
Update your Life doc. That’s your Mission/Purpose and your Life Categories. You may also want to add all the steps, exercises, and tools from this essay and the previous one (on daily fundamentals) into your Life doc, so that you can refer back to them easily.
Review your visions and the specific goals associated with those visions. Do this for each life category, for the long-term (life-time), medium-term (2-10 years), and short-term (1 year and checkpoints along the way). While you’re at it, assess whether you’re in danger of violating your anti-goals.
Consider the strategy/plan that you’re following for each life category, whether consciously or unconsciously.
Ask yourself if you have all the right systems in place.
Make sure you’re executing consistently—and finding joy as you do that.
Finally, go through your miscellaneous reflections.
Of course, you can tailor this methodology to your own preferences until you find what works best for you.
This is all always a work-in-progress for me. There are some things I do really well (like updating my Life doc, dreaming up visions, and coming up with the strategy to get there). But there are other areas where I’m currently struggling (e.g., coming up with specific, measurable goals; creating a singular Notion board system that tracks all those goals in one place, with timelines/deadlines; sticking rigorously to my daily time blocks; executing on things day after day after day; and not juggling too many activities and spreading myself thin). You, too, likely have your own version of these struggles. But you now hopefully have a foundational framework to examine your life, and you’ll just keep iterating and improving on that with time.
Keep learning—and think about how to implement those learnings into your governing docs.
As with each of our life categories, I think it’s important to keep learning about life overview and personal development stuff. I hope this Substack will serve as a useful companion on your journey of learning, providing you with several foundational frameworks.
We’re so frequently bombarded with life and self-improvement advice on social media and in the news these days, but it’s hard to know where exactly in the broader scheme of our life these tips fit in or how to implement them properly. The tips, then, can be either overwhelming or just plain useless (after all, most of the time, we read them and then forget about them soon enough). My hope is that, by establishing the foundational frameworks first, you’ll know what incoming information and tips you actually find novel and useful and how to slot them in.
When you do find kernels of wisdom that you want to retain and implement, you can add them into the appropriate place on your governing doc. Hear a bit of advice about packing your suitcase lightly? Put it in a new “Packing” section on your governing doc for travel. Read an article about achieving better sleep? Add the protocols that you don’t yet follow into the “Sleep” section on your governing doc for health & fitness.
On that note of learning: I owe a debt of gratitude to both Sahil Bloom and Ali Abdaal for several of the concepts in this essay. Their various pieces of content on life design have helped me clarify, over many months, my own process for conducting a Life Overview session.
If there’s one video you watch this week, make it this one from Ali Abdaal. It’s called “I Read 107 Productivity Books. Here’s What Actually Works.” The word “productivity” in the title is actually a bit of a misnomer. The video is about more than mere productivity; it’s about how to think about your life, and it covers a fair amount of what we’ve discussed here today.
Thanks for staying with me on this long read, and I’ll see you next time. In the meantime, feel free to reach out if I can help in any way.
