On Hitting Reset and Taking Stock of Everything

24 Questions for Personal Evaluation (Part I)

(image via Unsplash)

As I’ve made public via the most official of all forums, the Facebook Post, I have declared May to be my “Personal Reset” month. This is primarily because (1) the weather’s getting nice and that tends to be oddly motivational, and (2) I’ve consistently found that an unexamined life drifts away from, rather than toward, the establishment of good habits for well-being and growth, in all categories (physical, mental, spiritual, emotional — and to plumb the subcategories, intellectual and creative as well).

The idea of taking deliberate time for structured, in-depth personal reflection is something I’m stealing from my dad, who has enacted it in his own life and encouraged it in ours. It’s a concept which informs the retreat that the guys in my family take annually leading up to New Year’s, and which has inspired me to come up with some tradition of my own — hence, this.

I’ve synthesized innumerable influences from the past few years — articles, books, courses, etc. — to generate this framework for intentional self-consideration. I’ve broken it into four sections of six deep-cutting questions: General, Time & Relationships, Money & Things, and Health & Sustenance. This first post will tackle the first twelve questions (which make up the first two categories).


To be clear, I’m making no claims of exhaustive scope, particular wisdom, or earned authority in writing this list. Rather, I consider it a work in progress and very much a robust draft of a conversation with myself, first and foremost. I’m sharing this, though, because it’s become my experience that sometimes, insignificant and imperfect as you might consider them, sharing your efforts can affect and inspire others. I hope that’s the effect of these words.

I realize, too, that sharing publicly brings with it the burden of clarity. (I alone have the benefit of knowing where I’m coming from sans explanations.) In an effort not to spark an unhelpful response, I’m going to share two phrases to guide how I’d want anyone to approach this list of questions.

One: “Don’t indulge self-absorption for the sake of inward pride. Pursue self-awareness for the sake of outward purpose.”

The point of this exercise — and I would hope, most similarly introspective exercises — isn’t to improve one’s sense of superiority, or to encourage a navel-gazing or narcissistic bent. It’s to understand how to better fulfill one’s role as a human with specific callings and abilities, in relation to one’s surrounding universe and its entities.

Two: “A little bit better is better than the status quo.”

I wish I could remember who’s responsible for the notion behind this quote, but since I’ve heard the concept, it’s been an incredible reminder. In a nutshell, any progress is better than what you had before. I wholeheartedly recommend keeping this in mind when you embark on any kind of self-improvement exercise.

In an effort to potentially serve anybody else with this list, I’ve tried to explain clearly and quickly the heart behind each question, with the result being a pretty lengthy read. As such, if this is going to be useful to you at all, I suspect it will be by identifying and dwelling on a handful of questions that resonate most with you from a quick survey of the list. This may be worlds more useful than trying to thoughtfully answer all of them at once. And this may certainly better help you improve that ‘little bit’ to mark a tangible victory.

Without further ado, this is what you came for:


01/ In what areas would I like to grow?

— Very self explanatory. These could be the things that come easily, the areas that have nagged at us for some time: (wake up earlier, eat healthier, etc.). These are also the things that may take a second to think about, less immediate categories but ones that resonate when you stop to really ask this question (floss daily, read books more frequently, etc.). Picking 4–5 is probably sufficient, but be as specific as possible: (wake up at 6:30am on weekdays, get or create a meal plan for weight loss, etc.)
 — The question purposely emphasizes growth over elimination, because I’ve found that phrasing growth in positive/replacement terms is preferable to negative/quitting terms. On its own, a simple “quit” resolution can leave a behavioral gap which, honestly, you’re unlikely to fill with a positive habit. 
 — So, rather than, say, “quit staying up playing GameBoy Advance games on emulators till 2am,” consider a habit or practice you’d prefer to develop in its stead, and craft your answer that way: “schedule time to play GameBoy Advance games on emulators prior to a set bedtime.”

02/ In what areas have I lately demonstrated growth/improvement?

— Self-reflection can veer into dangerously pessimistic territory, especially if there’s a laser focus on future improvement. It’s important to be aware of the advances you have made and to celebrate the victories, small or large, that you’ve achieved over time.
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If you are somehow completely empty of ideas for this one, ask someone who knows you fairly well, and take seriously what they have to say. (I could go on a long tangent here about the foolishness of “compliment aversion,” but I’ll restrain myself.)

03/ What are my “personal drivers”— questions of who I am, what I believe, and what I must do in light of these — and have I evaluated my answers recently?

— What is the motivation for everything you do? This is going way deep. Sure, it’s unrealistic (and likely unhelpful) to have these on your mind 24/7, but thankfully, that’s not the problem most of us have; if anything, it’s the opposite. Our faith, guiding philosophies, identity, and personal mission statement too often go unstated and unconsidered.
 — Simply having a category for defining our innermost purpose will have a transforming effect on the smallest of choices we make. Reevaluating if we are being who we intend to be, rather than taking this for granted, can provide the course correction we so frequently need. A solid response to this question could well take the form of personal manifesto (minus the political overtones, natch).

04/ What systems do I need to establish to promote success in forming good habits and achieving my goals?

— I firmly believe as a rule, with extraordinarily few exceptions, that the average person cannot take a good intention (say, getting fit), discover some expert’s single prescribed method for achieving it (say, get up at 5:30am for a run then do a strength/conditioning workout for forty-five minutes followed by a twenty-minute cool-down period, to be repeated daily save for one day of rest a month), apply said method as-is, and successfully attain the goal. 
 — Most of us know this is a silly thought; we’re all wired differently and will encounter a thousand obstacles to accomplishing this One Perfect Plan. And yet, too often, we consume lists of how-to’s with the voracity of harried rodents, shoehorning new advice into the same ineffective patterns that have us bemoaning our current existence.
 — Before you embark on the direct practicals of fresh resolve, consider the peripherals: are you creating an environment that will foster your pursuit of growth, or unconsciously sabotaging your own efforts by changing nothing? Things like the company we keep, the time we spend on specific activities, or a state of orderliness/managed chaos can have dramatic effects on our motivation.

05/ How am I doing at seeking external wisdom, and synthesizing it to improve my personal practices?

— Are you selecting and consuming books, articles, podcasts, classes, gatherings, conferences, and other opportunities to glean from the insight of other humans? Are you considering how to adapt that material to accommodate your own learned strengths, weaknesses, and passions?
 — I’m not advocating an ultra-customized, abandon-what-I-disagree-with, consumption-bubble mentality here, but rather a mindset that soberly sifts through the declarations of thoughtful people, then determines how those will affect you, and your behavior, both as (1) a fellow human with shared tendencies and (2) a unique individual with particular drives.

06/ How would I like to be remembered, and how well have I achieved that so far?

— Without getting excessively morbid, I think it’s still extremely helpful to think about your legacy — particularly in light of how little time we are guaranteed (i.e., none). We can avoid considering how we want to be remembered because of how self-absorbed it may seem, but in reality, it’s such an outwardly-oriented category: how we’re remembered depends on how effectively we’ve engaged with people who are doing the remembering.
 — Are you considering the effect you have had, are having, and could have on the lives of those around you, and beyond? Are you on track to make the impact you want to make? If not, what needs to change?


07/ Have I prioritized my relationships accurately?

— Obviously, this doesn’t mean that we rank people based on how much value they bring us. There is, however, something to be said for having a personal awareness of the general nature of our relationships with those in our lives, and deciding who gets dibs on our energy, time, and devotion.
 — There are friends who are barrels of effortless fun to spend a day with; there are others for whom an evening spent together will be marked more by serious conversation and some measure of caregiving (in either direction). One category is not inherently worth more than the other, but we must be able to discern how and when to expend ourselves in the company of each group, if we want to improve the positive impact we can have in each of our relationships.

08/ How am I doing at giving sufficient time away, and keeping sufficient time for myself?

— This goes hand in hand with the previous question: are you making an effort to reach beyond yourself for the purposes of care (both ways) and real enjoyment? At the same time, are you setting aside time to actually rest, relax, re-evaluate (by reading an article about 24 questions to ask yourself, for example), and maximize the benefits of solitude? Your natural bent toward extro- or introversion may alter the necessary percentages, but be wary of using personality as an excuse to avoid the challenge of potential re-apportionment.

09/ Do I have any system for prioritizing activities that align with my personal goals and mission statement?

— This question is getting at your need to either (1) adopt a basic practice of time management, or (2) interrogate the methods you already practice. The nuts and bolts are flexible here: whether it’s proactive planning, retroactive evaluation, or in-the-moment activity-logging, anything that gets you thinking about why you do what you do can be helpful in aligning your behaviors with your mission and goals.

10/ Do I have any system for effectively splitting my time between activities that are recharging vs. demanding my energy?

— This is forever an elusive balance, but again, it begs conscious thought. Activities that lay claim to our energy are not inherently negative: learning a new skill or providing meaningful (though strenuous) service, for instance, can be ultimately beneficial. On the flip side, something that may be considered ‘restful’ can be a problem if taken in poorly-managed doses. Procrastinating a serious deadline by pursuing a relaxing hobby is one such ineffective use of time (and, in effect, loses its ‘recharging’ power due to your constant fear of the looming deadline).

11/ If I knew I was about to lose someone close to me, what would I want to do with/for them?

— I’ve often thought about the fact that you will never be adequately prepared for the deaths of those you love — certainly not when it’s a sudden, shocking passing, but even when it’s a visible certainty (e.g., those final deathbed days). There will always be a measure of longing for things undone and unsaid, so this question is not meant for obsessing over the impossible by eliminating all regrets entirely. 
 — Rather, it’s an encouragement to consider how to enrich the moments we still have, to the extent that we can. We can be active in conveying love too commonly left unexpressed, or seek to mend broken bridges that would otherwise haunt us. We can schedule more calls, write more letters, share more meals, embark on more adventures…the list of possibilities is endless. These choices will never be enough to make a loss more bearable, but they will certainly provide a lasting comfort, wholeness, and richness both now and in the long term.

12/ Do I have external accountability for areas where I am seeking growth?

— It’s no secret that many times, the catalyst for change is someone else. If we’ve exhausted our stores of motivation in a given area, it’s shocking how the smallest input from someone we trust can replenish our resolve in no time. Do you have people in your life providing that kind of value? Are you seeking them out?


The list goes on! Check it out here.