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“In a little while you too will close your eyes, and soon there will be others mourning the man who buries you.” - Marcus Aurelius, Meditations
Sometimes in life, it’s informative to start at the end and build backwards. This process of inversion has long been championed by Stoics as a grounding practice. Remembering the ephemeral nature of life and your meager place within it is useful for gaining perspective and clarifying what is most important to you. Remembering life’s fleeting nature helps to inspire action today (carpe diem, anyone?):
"There is a Japanese term: Mono no aware [物の哀れ]. It means basically, the sad beauty of seeing time pass - the aching awareness of impermanence. These are the days that we will return to one day in the future only in memories." - The Midnight
Drawing a bit of inspiration from this practice, I went through a mental exercise a couple weeks ago where I looked at my life and my goals in the context of my own nonexistence. It’s an inevitability that we will all one day face (hopefully later rather than sooner for all receiving this), and looking over your priorities from that perspective is a useful exercise for refining just how flippantly you should squander your precious time.
There are a few versions of this practice, ranging from the most to least existential, and I thought you may enjoy considering a few of them:
Wynn’s Prioritization with the End in Mind
Admittedly, this little exercise came about in the midst of a moment of existential dread. Upended employment, losing your way, and grinding through the job hunt are great for spurring the self-examination of what exactly it is you want to do and who precisely you want to be. These quandaries have been rattling around my mind the last few months, but it was a late night burst of productivity wherein I haphazardly explored these questions in a more tangible way.
I titled the sheet “If I Were Going to Die Tomorrow…” (dour, I know), and populated it with the following questions:
What would I regret?
What would I miss?
Would I be happy with my work?
Who would I miss?
What wouldn’t I regret?
I then took a half hour ruminating on these inquiries about life, and answering each with a few bullet points. This isn’t scientific, but it’s forceful.
A few personal examples of my thoughts and answers:
What would I regret?
A simple starter and meme-like answer, but I’d certainly regret having seen so little of the world. Even thinking more broadly, there are specific things/places/wonders I’d like to see before I’m reduced to dust, and I’m starting to realize just how much of a concerted effort it will take to ensure I’m not left wanting forty years from now.
What would I miss?
This question drew insights around how I spend my time. There are so many things that I don’t really love, yet squander my free time doing/attending/etc.
There are many things I won’t be able to do forever (both in the context of death and aging - athletic activities, travel, spontaneity), yet I continue to push off as if time were renewable.
Who would I miss?
This very much spurs the same as above. If a friendship or a relationship isn’t a hell yes, it should really be a hell no.
The greatest joys in life come from compound interest, and relationships are much the same. Digging deeper in fewer exceptional relationships will be vastly more rewarding than shotgunning a couple dozen surface level interactions.
Especially considering the rate at which life responsibilities rob you of chances to spend deep, quality time with the people you like, love, and respect.
Would I be happy with my work?
This idea plagued me before business school and continues to haunt me now. If I died tomorrow, I would deeply regret having spent the bulk of my professional life making a few rich guys richer (see: my pre-MBA jobs).
Additionally, I would regret never having built something of my own.
These are vague, but that’s fine. It’s an exploration of self, and our inner workings are rarely clean cut.
And finally, I drew a little timeline with dots and drop downs at the bottom of the paper looking something like this:
A rather superfluous timeline, sure to be vastly incorrect. But a useful exercise for zooming out and considering things that could happen in my life, should I be lucky to make it that far. Those arrows dropped down to various ideas of milestones (‘work for self’, ‘family’, ‘kids’, ‘kids leave for college’, ‘visit x countries’, ‘do y life event’, etc.) to get me noodling on just how short/long I could potentially have. When in doubt, zoom out.
Tim Ferriss’s Fear Setting
I came across Tim’s Fear Setting idea a number of years ago, and it’s very similar to the exercise I dreamed up above:
If you are nervous about making the jump or simply putting it off out of fear of the unknown, here is your antidote. Write down your answers, and keep in mind that thinking a lot will not prove as fruitful or as prolific as simply brain vomiting on the page. Write and do not edit—aim for volume. Spend a few minutes on each answer.
Define your nightmare, the absolute worst that could happen if you did what you are considering. What doubt, fears, and “what-ifs” pop up as you consider the big changes you can—or need—to make? Envision them in painstaking detail. Would it be the end of your life? What would be the permanent impact, if any, on a scale of 1–10? Are these things really permanent? How likely do you think it is that they would actually happen?
What steps could you take to repair the damage or get things back on the upswing, even if temporarily? Chances are, it’s easier than you imagine. How could you get things back under control?
What are the outcomes or benefits, both temporary and permanent, of more probable scenarios? Now that you’ve defined the nightmare, what are the more probable or definite positive outcomes, whether internal (confidence, self-esteem, etc.) or external? What would the impact of these more likely outcomes be on a scale of 1–10? How likely is it that you could produce at least a moderately good outcome? Have less intelligent people done this before and pulled it off?
If you were fired from your job today, what would you do to get things under financial control? Imagine this scenario and run through questions 1–3 above. If you quit your job to test other options, how could you later get back on the same career track if you absolutely had to?
What are you putting off out of fear? Usually, what we most fear doing is what we most need to do. That phone call, that conversation, whatever the action might be—it is fear of unknown outcomes that prevents us from doing what we need to do. Define the worst case, accept it, and do it. I’ll repeat something you might consider tattooing on your forehead: What we fear doing most is usually what we most need to do. As I have heard said, a person’s success in life can usually be measured by the number of uncomfortable conversations he or she is willing to have. Resolve to do one thing every day that you fear. I got into this habit by attempting to contact celebrities and famous business people for advice.
What is it costing you—financially, emotionally, and physically—to postpone action? Don’t only evaluate the potential downside of action. It is equally important to measure the atrocious cost of inaction. If you don’t pursue those things that excite you, where will you be in one year, five years, and ten years? How will you feel having allowed circumstance to impose itself upon you and having allowed ten more years of your finite life to pass doing what you know will not fulfill you? If you telescope out 10 years and know with 100% certainty that it is a path of disappointment and regret, and if we define risk as “the likelihood of an irreversible negative outcome,” inaction is the greatest risk of all.
What are you waiting for? If you cannot answer this without resorting to the previously rejected concept of good timing, the answer is simple: You’re afraid, just like the rest of the world. Measure the cost of inaction, realize the unlikelihood and repairability of most missteps, and develop the most important habit of those who excel and enjoy doing so: action.
Although his checklist comes from a place of hesitance about a specific idea/dream you’ve been putting off, much of its ideas can be encapsulated by a phrase of Tim’s that really informed much of my pre-MBA career thoughts: “What’s the worst that could happen?”
Thousands of years of evolution have honed the human mind to be incredibly risk averse, and rightfully so. Survival is largely about mitigating risk. The upside of getting a single salmon vs. the downside of being mauled by a bear is a pretty lopsided risk distribution when you’re a neanderthal. But this deeply ingrained, risk averse mindset ends up actually being detrimental in our modern era where the stakes tend to be so much lower. Furthermore, the extension of this tendency is that we generally struggle to envision the possible upside of taking risks and trying new opportunities. It’s usually much easier to calculate and fear a downside which is tangible based on our experience vs. an unclear possibility of upside or improvement to our life that’s otherwise unknowable.
It was through this lens that I contemplated my MBA career pathing. When considering my goals of pursuing either Venture Capital or a Startup for my career (risky endeavors, both), I took a square look at the possible outcomes. My downside being a return to the status quo, and not even that, but a return to a previous life in fínánce at a (likely) higher salary given my MBA status. Pretty guarded downside. And although that would have been safer and more easily pursued, it would have resulted in a compromise on my happiness and, more importantly, my precious time.
I understand the privilege of my situation in considering these possibilities. A straight, white, male with a finance degree contemplating returning to his white collar job. Woe is me. But nonetheless, I contend that internalizing this mindset is valuable for almost anyone. Many of the greatest joys and opportunities in my life have come from taking unorthodox risks, and I believe that many of my readers would echo that sentiment.
And a pairing in that vein:
"Life shrinks and expands in proportion to one's courage." - Anaïs Nin
“Most people will choose unhappiness over uncertainty.” - Tim Ferriss
Sahil Bloom’s Anti-Goal Framework
Anti-Goals are a more tactical (actionable) approach to problem inversion. They are the practice of looking at your goals, then envisioning the inverse behaviors that will hinder you from accomplishing them. They also help to set guardrails by forcing you to consider the knock-on consequences that achieving your goals may require- what would make this aspiration a pyrrhic victory?
There are two great writeups about leveraging these: one from Sahil Bloom and the other from Andrew Wilkinson. I think the latter provides a particularly compelling example for my audience (primarily knowledge workers) when thinking about your own life:
So, instead of thinking through what we wanted our perfect day to look like, we thought about the worst day imaginable and how to avoid it. We inverted and came up with what we call Anti-Goals.
Our worst possible day looked like this:
Full of long meetings
A packed calendar
Dealing with people we don’t like or trust
Owing people things / not being in control / obligations
Having to be at the office
Travel
Tired
Working backwards from there, we made this set of Anti-Goals:
Never schedule an in-person meeting when it can otherwise be accomplished via email or phone (or not at all)
No more than 2 hours of scheduled time per day
No business or obligations with people we don’t like—even just a slight bad vibe and it’s a hard no
Never give up voting control of our businesses, no favors from people who could need something from us (ensure the rule of reciprocity doesn’t kick in)
Work from a cafe across from a beautiful park where we can come and go as we please with nobody to bother us
Video conference or pay for people to come visit us
Never schedule morning meetings, sleep in when needed
Problem solved.
Of course, we still have the odd unavoidable crappy day, but these simple Anti-Goals have made our lives immeasurably better by setting an Anti-Goal instead of a goal. Try it sometime, it’s insanely simple and strangely powerful.
“It is remarkable how much long-term advantage we have gotten by trying to be consistently not stupid, instead of trying to be very intelligent.”
–Charlie Munger
Work hard, think deeply.
- W
Bonus inversion: The Moral Bucket List.
“I’ve been thinking about the difference between the résumé virtues and the eulogy virtues. The résumé virtues are the ones you list on your résumé, the skills that you bring to the job market and that contribute to external success. The eulogy virtues are deeper. They’re the virtues that get talked about at your funeral, the ones that exist at the core of your being — whether you are kind, brave, honest or faithful; what kind of relationships you formed.
Most of us would say that the eulogy virtues are more important than the résumé virtues, but I confess that for long stretches of my life I’ve spent more time thinking about the latter than the former. Our education system is certainly oriented around the résumé virtues more than the eulogy ones. Public conversation is, too — the self-help tips in magazines, the nonfiction bestsellers. Most of us have clearer strategies for how to achieve career success than we do for how to develop a profound character." - David Brooks