Learn to Regret Well
When we think of “free will”, it’s often looked at optimistically and without pause.
Yet, something that is frequently overlooked is the responsibility that inherently comes with this liberty; a responsibility that can shatter someone who’s unprepared to bear the necessary pain which comes with making decisions of any magnitude.
This is especially difficult when the decisions are of equal weight in our minds.
It’s for that reason I thought it’d be best to spend some time today talking about how to approach those nearly impossible “either/or” situations.
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Reach for Something Else
For this week, I thought it’d be most appropriate to include a resource I find most helpful in reviewing notes and quotes: Readwise.
Readwise is an app that compiles all your highlights from various sources like Kindle, iBooks, and web articles into one place, making it easier to review and remember what you've read. Its main benefit is that they send daily emails with a selection of your past highlights, or random quotes from books you might like, helping reinforce retention through spaced repetition.
Additionally, it offers features like tagging, searching, and the ability to create custom notes, which can enhance learning, personal development, or research by keeping valuable insights accessible and organized (if that’s your style).
If you’d like to try Readwise, you can start with a 30-day Free Trial, but after that, it does cost a small fee. If you click this link or the picture, you’ll get an additional free month trial (and I’ll also get a free month).
Why You Must Learn to Regret
Making difficult choices is fundamental to a voluntary life; the voluntary life being a prerequisite to a good life.
When we face two options of seemingly equal value, each demanding its pound of flesh, the weight of decision can feel paralyzing. Yet the cost of paralysis—of not choosing at all—often exceeds the price of either choice, so as we’ve talked about before, it’s necessary to choose.
This proverbial fork in the road can manifest itself in a variety of ways with varying levels of significance; unfortunately, any way that it manifests will often incur discomfort, sadness, heartache, and even despair.
Why we encounter these feelings is not because we’re failing to do any of the groundwork of setting our aim, are unbalanced, or have faulty motivation… no, the reason is two fold; 1) we’re in a new situation with a whole lot more awareness than before and 2) the value of each option might well and truly be equal to us.
To not stop there, as life often neglects to give us that courtesy, maybe the issue goes as far as to end poorly in some way for you; perhaps no matter what you choose, you’ll end up violating some natural law or instinct and lose something you value—you have to give something up.
This is an important point to hone in on: to achieve a good life and to live with integrity, you must be willing to sacrifice.
But why is that a necessity to a good life?
Simply put: if you don’t, the sacrifice will be chosen for you.
Now, when you’re in a situation like this, maybe it seems like it would just be better for fate, karma, or God Almighty himself to intervene and just choose the outcome for you—but that’s not how it works.
Don’t mistake me for saying that things don’t sort themselves out with time, they certainly do; however, it’s better to not allow things that need to be addressed to go unaddressed for too long—you might just end up worse off than had you simply chosen to act in one of the directions despite being unsure of the best option and their potentially disastrous consequences.
Of course, it’s possible to act too hastily, but ours is an age of over-deliberation and inaction, so that is the lens I’ll try to look through today.
So, how do you make a decision when you are going to wind up getting hurt regardless?
Accept the hurt.
Go back to basics.
Ask questions—usually this takes place in the form of uncomfortable conversations or gathering ideas to help you weigh out the options properly.
Pick Your Regret.
1. Accept the hurt
"All great things must first wear terrifying and monstrous masks in order to inscribe themselves on the hearts of humanity".
Friedrich Nietzsche
First, it is best to acknowledge that every significant choice involves some level of pain, loss, and sacrifice. It’s best to get out in front of that truth to save us from the delusion that “just maybe” you could avoid it.
Nope. There’s no getting out of it.
We should know that this is also true in proportion to the decision’s magnitude.
Just how important is this decision?
Choosing between a high-paying job that requires relocation versus staying close to family but with less financial reward is one example that bears some considerable weight and complexity.
Different value structures emerge and we have to consider how we view our family connections as opposed to our career outlook, and which might bring us more meaning over time.
A key word lies in the fold here, one that springs the pain of anxiety upon us when we take to deliberating over our possible course of action: might.
For our own well-being, it’s necessary for us to see most outcomes as certain, “if I act this way, then this will happen.” Very rational, very trusting, but also very naïve if we fail to put down this assumption from time to time.
And on the inverse, if we never act and only deliberate, you’re equally if not worse off than acting upon the former assumption.
Nearly no outcome is absolutely certain, despite what we might like to believe.
“Might” is an uncomfortable admission of the limited scope of our insight and knowledge, which also helps to exclude that blinding arrogance which is so common when making important decisions.
Discomfort is an integral part of growth and change, to pretend that we’re so skillful and exceptional as to avoid the hurt that comes with making important decisions is a petty delusion.
And who’s to say the pain wouldn’t be a good thing for you?
When both options demand sacrifice, understanding and accepting this can prepare you mentally and emotionally for the decision-making process to come.
2. Go Back To Basics
What we do will echo through eternity, in big and small ways; determining how our actions will impact not only us but the lives of others, born and unborn, is another vital consideration on this road to building an understanding necessary to make our decision.
This involves a deep dive into how each choice aligns with your values, long-term goals, and personal fulfillment. In short, we evaluate the significance (meaning over time) of the outcomes of both decisions.
Short-Term AND Long-Term: Evaluate how each option serves you immediately and years down the line. Perhaps one job offers instant financial gain but little room for personal development, while the other nurtures your passion but at a slower pace financially.
Legacy and Life Stages: Consider how this decision fits into the broader tapestry of your life. Will this choice contribute to the legacy you want to leave behind? Does it match the current stage of your life where certain aspects might be more or less important?
Now, what do we do when the matter is less trivial and more existential?
Forget jobs for a moment, how do you measure your choices when your soul is on the line; what matters to you then?
Is it utility? or do the scales tip for other reasons?
Think of a time, if ever there was one, where you had to choose between two things that, no matter what, violated something sacred and natural to you.
Perhaps one option allowed you to approach life in the way you wanted and you felt that you could be truly genuine to both who you are, who you think you could be, and those around you; while the other is a situation you have already dedicated yourself to and to choose the former would be violating your word and, should you believe, your promises to God.
How do you weigh things then?
3. Ask Questions
Good decisions are rarely made in isolation. Engaging with others or using tools like reading and writing can provide much needed clarity.
Why?
Because they allow us to see beyond our narrow and biased perspective.
This gives us new ideas, or potential solutions, that inevitably assist us in making the best decision despite how poor the situation might be.
The first place we might look for answers is the place we might be least willing to go: to the source of the conflict.
Whether this is a spouse, professor, employer, or ourselves, we should seek to confront the source in order to begin clarifying the value of our decision.
When seeking counsel from others outside the immediate situation, try to speak to friends, mentors, or professionals who have faced similar dilemmas. Their insights might highlight aspects you hadn't considered and propel you to a more firm decision.
This might seem like very basic advice, but it’s often in neglecting the basics that we begin to go wrong.
In the absence of, or in addition to seeking a word of advice from someone worthwhile, use writing as a tool to explore your thoughts. Jot down pros and cons, but more importantly, how each choice makes you feel and the potential consequences of those feelings.
It’s through writing that we just might be able to organize ourselves enough to see things clearer than ever before—it’s probably still pretty murky, but it’s better than the total blackout that existed before.
Reading is also a powerful investment that can help us make our decisions more clear.
Books often provide wisdom that resonates with your situation, you just have to be willing to look. Don’t procrastinate by reading books, but do consult ancient pages when time allows, there’s likely something tucked away that will help you gain understanding.
It’s also important to remember that you shouldn’t be consulting these things to make the decision for you, but only to see where you might be mislead and lacking in knowledge to make a grounded decision.
4. Pick Your Regret
The last piece to this brief formula for choosing between two seemingly suitable (or deadly necessary) options is a completion of the first point of “accepting the hurt”, but steers us back toward action and keeps us from deliberating too long.
Pick your regret.
Perhaps the best illustration of this is within Søren Kierkegaard's work, "Either/Or," where he ponders the necessity of regret in our pursuit for a good life:
"Marry, and you will regret it; don’t marry, you will also regret it; marry or don’t marry, you will regret it either way. Laugh at the world’s foolishness, you will regret it; weep over it, you will regret that too; laugh at the world’s foolishness or weep over it, you will regret both. ... Hang yourself, you will regret it; do not hang yourself, and you will regret that too; hang yourself or don’t hang yourself, you’ll regret it either way; whether you hang yourself or do not hang yourself, you will regret both. This, gentlemen, is the essence of all philosophy."
Kierkegaard's quote illuminates the inevitable nature of regret in human decision-making, suggesting that rather than avoiding regret, we should choose which kind we are willing to live with.
Regret Analysis: Think about which regret would be more bearable. Would you rather regret not taking a risk or regret the consequences of a risk that backfired?
By accepting the inherent pain of choice, evaluating the meaning and impact over time, engaging in thoughtful questioning, and consciously choosing which regret to live with, you arm yourself with the tools needed to navigate these treacherous crossroads.
Remember, the cost of indecision might just be the heaviest sacrifice of all.
Whether it's choosing a career path, a life partner, or the countless other significant life changes, there is sure to be pain, so don’t allow it to hold you back from making the essential steps forward to the life of your choosing.
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Thanks for reading!
See you next week!!
xDevan