6 Ways to Avoid Regret and Quickly Transcend Grief

Hello, dear readers. Regret and grief are experiences that dampen the joys of life. Recently I have connected some major dots and gained insight into this area. We will explore how you can avoid regret and quickly transcend grief.

This will be a fairly long post, but feel free to skip around, I’ve provided an overview of this post’s organization below. It will be worth it, the diligent reader is certain to obtain at least one new and personally impactful insight.


I have developed a strong desire to avoid regret as it has caused gut wrenching pain many times in my past during times of loss (e.g. relationships, work opportunities, housing opportunities, etc.)

The regretful moments earlier in my life brought feelings that were very new to me. I was also far less aware (mid-late teens) and less mature. I remember my first major regret being around a romantic relationship. Teenagers put a lot of emphasis and care to their relationships, so this was a hard hit.

I remember the gut wrenching pain from all of the worry, it kept me up all night. My thoughts spiraled on what-ifs and my desire to retreat back into the past to redo it was strong. If only I could ask someone for a redo.

These feelings were compounded even more intensely since I was an individual with a strong desire for control. I felt like if I just wished hard enough, or thought of the right plan, I’d be able to correct everything.

My lack of maturity at the time left me without the proper tools or awareness to deal with this regret. I have ever since organized my life to minimize regret, from public speaking to taking on physical and mental challenges.

Recently, I had another regret related to a housing opportunity. My maturity at this stage was enough to manage it well. This got me to think about the progress that I’ve made.

This time, I’ve utilized my experience with reflection and all the other important insights that I share on my blog. This has led to profound realizations.

I want to share my insights with you.

Here is the structure of this post:

  • Before Regret: How Best Avoid
    • Clarity
      • The Associated Feeling and Cue (Warning Sign) – Crystallized
      • How to Improve Your Ability for Clarity – Practice
      • How to Immediately Boost Clarity On Demand – Journal
        •  Pre-mortem
        • Wholehearted Action
  • After Regret: How to Learn and Recover
    • Awareness
      • Explore the Sensations – Recognize Stages
      • Discover the Meaning – Journal
      • Get into the Right Mindset – “This, Too, Shall Pass”

Before Regret – How to Avoid

Big Idea: Deeply visualize yourself carrying out the action. Do your best to prepare.

Basically: Become crystal clear on what it is that you want in life.

You have a big decision to make. How do you make a decision that you won’t regret?

The answer comes down to Clarity.

The common theme I’ve found between all my moments of regret has been the inability to vividly visualize and articulate what I want.

What my desires were, the hierarchy and their relative importance, and the factors that play a role (e.g. time-frame), all were not known. In short, I lacked clarity.

There are several parts to this:

  • The Associated Feeling and Cue (Warning Sign) – Crystallized
  • How to Improve Your Ability for Clarity – Practice
  • How to Immediately Boost Clarity On Demand – Journal

The Associated Feeling and Cue

I’ve found clarity to have an associated feeling to it. This is very useful to gauge whether or not you should spend more time planning.

It feels like a crystallization of thought, a sudden “ah-ha!”, a moment where things click into place and the stars align. It is a moment of beautiful harmony.

Your confidence peaks momentarily, and you feel a sudden rush of “it all makes sense”. You feel as if you can go in and out of the thought and explore it at various levels of detail. There is a strong feeling of control associated with peak clarity.

Clarity is not easy to obtain, it requires effort and critical thinking. You’ll be in a state of ambiguity for a long time as you gather a bunch of pieces to the puzzle that you’re not even sure are needed. This is the acquiring stage and its uncertainty is what causes most to not go any further.

Later, the puzzle will start to take form and where to place the next piece will seem more clear. As you place more pieces the solving process speeds up more and more. This is much like the Solitaire card game, or any puzzle, really. The start is slow and tedious, but after you develop an understanding of the pieces you have and a few ways to orient them, things speed up quickly.

This is a beautiful analogy for how I see clarity.

The roadblocks come early in the process, this is what causes most people to fall short. Solving puzzles requires patience and persistence. Problem solving of any kind is a puzzle in itself, that is why “intelligent” people tend to be stubborn and persistent.

That is no coincidence, and if you wish to be more intelligent, emulate the characteristics of intelligent people. A great to practice this is through solving challenging puzzles. This relates to the importance of Identity and how you can use archetype’s characteristics as a blueprint for the traits that you should develop. I talk about this more in my Effective Living series.

See my post: The Ultimate Guide to Clarity for an in-depth exploration on how to gain more clarity.

You can apply this insight by recognizing your inability to clearly visualize and articulate what is important to you.

A lack of clarity feels like the desire you have is not crystallized, it isn’t a thought that you can easily return to without much mental effort. The thought is just a cloud with no vividness. This is a warning sign of future regret from a bad decision. DO NOT OVERLOOK.

I wager that individuals who learn rapidly are able to do so because of their ability to quickly crystallize a thought.

Once an idea is fully crystallized, it is as if you can see it and experience it already. This is a feeling that I associate with the “I got it!” insight, where things click into place.

As a side-note, this is a great indicator that you’re ready to move on to the next topic in whatever subject you’re learning. You will need to revisit it again later, right before you forget (i.e. spaced repetition), to crystallize it long term. But, for the moment, you’ve successfully chunked an important piece of information and made connections between ideas. Speed learning is about how you spend your time effectively.

Whenever someone says “you can achieve anything that you put your mind to”, think of clarity. Because that is exactly what setting your mind to something means, it’s that feeling of things clicking in place.

How to Improve Your Ability for Clarity

Clarity is a skill. It takes a lot of exploration, tweaking, and trial and error.

Approaching life with an explorative mindset is a great way to glean the most out of all the experiences that you have in life. This includes gaining clarity.

As you go through the process of having an experience and reflecting on it, you’ll develop an understanding of your desires and tendencies. This will help in being able to visualize how you will respond or feel during a situation that has not yet occurred.

Exploration is a big concept that I talk about to a great extend in the Effective Living series, but for now, it simply means not avoiding the physical sensations you experience and not labeling them as good or bad. It is a mindset of viewing the experiences in your life as an awareness of and not identification with. It emphasizes independence, the less external support crutches, the better.

You improve your ability to make decisions with clarity by making more decisions with clarity. And you gain these opportunities by engaging in novel activities, especially those that are challenging and have risk to them.

Take on bold challenges that involve risk, such as public speaking or interviewing for a job you really want. It is relative. Anything works, as long as a feeling of uncertainty and slight fear bubbles up inside you. That means regret will be more profound and thus the lessons learned from how you can improve on clarity will be more profound.

There’s an important point here, and that is Clarity requires discipline. It is a discipline in knowing what is in your control and what is not and a discipline in being able to slow down early on to take deliberate steps forward. It requires patience.

How to Immediately Boost Clarity On Demand

If a hefty decision awaits you, the best way to gain clarity, immediately, is to journal. This means to simply get out pen and paper and start writing.

Explore your worries and emphasize visualization. Focus on what is in your control.

A simple practice that I’ve found helpful is a pre-mortem.


Clarity is vital to ensuring you make good decisions, but it isn’t always practical for 100% clarity. A balance is needed. A lot of things in life is naturally ambiguous, you’ll have to weight probabilities and ponder various outcomes

This is where the power of having a pre-mortem comes in.

You may be familiar with a post-mortem, the examination of a body after death. A pre-mortem is similar, but it involves the time before death.

“Death” in this context is the death of a decision, the point in time after a decision has already been made and the consequences have surfaced.

So, a pre-mortem is planning for the consequences of a decision before the decision is made.

There are three important steps to this:

  • Consider Pros/Cons
  • Recognize What’s in Your Control
  • Visualize Worst Case Scenario

First step is to develop a list of pros and cons for your decision. What might go wrong? What are the obstacles? Consider consequences that will result as a result of the initial consequence, the second and third order consequences. This is a practice in visualization and clarity, it is best paired with journaling, writing on physical paper.

You then consider what is in your control and what is not. This can be tricky, be sure you can truly visualize yourself influencing the factor, or else it isn’t much in your control. Become clear on how you can influence the factors and what obstacles there might be.

Finally, visualize the worst case scenario, come to terms with it. Go deep in the visualization. You may uncover other pros/cons or gain more clarity on what your true desires are. This is an important step. The worst case scenario will probably not happen, in which case, everything else is just bonus, since you’ve accepted the worst case as a possibility.

A pre-mortem is a great practice in eliminating most worries. This works great to help clear your mind of anxious thoughts so that you can think more rationally (less emotionally) when making your decision.

Wholehearted Action

The most gnawing kind of regret is that when you know you could have done better.

A recent missed job opportunity was hard, but I didn’t know how to prepare coming in and learned a ton during the process, so it wasn’t that big of a sting, despite the fact that it would have completely changed my way of living (e.g. moving, desirable location, etc.)

Going wholeheartedly in the preparation allowed me to come to terms with reality quicker.

When you complete a pre-mortem and it’s time to take action, do so wholeheartedly.

Leave nothing behind, give it your all. By now you should be able to come to terms with it not working out (thanks to the pre-mortem) and coming to terms with it working out was never a problem, so you’re in a good spot.

You’re okay with it working out and you’re okay with it not. Now, drive all your attention to the present moment and take wholehearted action.

Even if things don’t work out, you at least did all that you could. This will make the sting much less and progress you faster through the stages of grief.

After Regret – How to Learn and Recover

Big Idea: Failure is a motivating opportunity. Don’t suppress it or hide from it.

Basically: Face the discomfort head-on, pass through the stages, and find the meaning.

You’ve made a regretful decision. How do you make the most out of this opportunity?

To start, recognize that it’s just that, an opportunity. Trust that that is the case, because at first it will not feel like it is.

Don’t just trust, but prove to yourself that no matter what, you will be alright.

This trust comes easier the more opportunities you have in dealing with regret or adversity. After experiencing hardship enough, you soon realize that “this, too, shall pass”, that all feelings are relative and temporary.

The big idea here comes down to Awareness.

Here are a few insights that involve Awareness:

  • Explore the Sensations – Recognize Stages
  • Discover the Meaning – Journal
  • Get into the Right Mindset – “This, Too, Shall Pass”

Explore the Sensations

By the Principle of Relativity, everything seems bigger up close. When you’re right up in the moment with the flood of emotions and sensations, your survival-focused mind will give that a LOT of importance. You have to take a step back to see the bigger picture, this includes the meaning and the opportunities.

Therefore, it’s important to keep perspective during times of adversity.

This requires emotional maturity. But that doesn’t mean not feeling the emotions, it simply means recognizing that they are temporary and to not suppress or avoid them.

I find that giving myself permission to feel the worry or overwhelm helps me to process it quicker. The result is an overall lighter feeling. I soon realize that the bus will come back around. It’s important to be prepared for the next iteration, feeling sorry for yourself and being stuck in the past, without processing the emotion, will cause you to miss the bus again again. This negative spiral will compound the feeling of regret.

Feel the sensations that are there, process them, and then move on with the weight lifted off.

There is a wonderful book by Brene Brown called “Rising Strong” that covers how to recover from being face down in the trenches better than any book I’ve come across (I’ve read over a hundred).

The moment after adversity is analogous to finding yourself face down in an arena. Rising back up is the process of recovering from that adversity.

To turn a moment of adversity into a defining moment that pivots your life to new levels of success requires delving deep into that discomfort. Too many people rely on others as crutches to help them out of challenge. But you’ll be far better off if you face the challenge alone.

The best mentor or parent isn’t the one that always holds your hand and helps you. Those actions usually come from a selfish nature, a desire to feel special and important.

True mentorship comes from setting challenges for the child or mentee and hoping they fail. Your job is to mimic reality as much as possible, the real world knocks you down a LOT, and there won’t always be people there to help.

That to me is what makes parenting or being a mentor hard. You have to hope your child fails, so they can learn how to deal with it.

They will fail at some point in life, it is the job of the parent or mentor to make sure they are well prepared for it. The first time someone fails hard at something and finds themself face down SHOULD NOT be when they’re an adult. That is how people become highly dysfunctional.

It is the job of a parent or mentor to make sure that this DOES NOT happen.

The best mentors provide the following characteristics:

  • High Expectations
  • Assurance
  • Direction
  • Support

This is an idea crystallized when I came across Dan and Chip Heath’s book The Power of Moments:

They summarize mentorship in a single sentence: “I have high expectations, but I know you can do it, so here is a challenge, and if you fail, I’ll be here to help you recover.

The more independent you remain while facing adversity, the better.

Avoid “talking about it” with others, instead, journal about it. You will discover your true nature, desires, and tendencies far more profoundly as a result. Meaning will begin to take shape in your life and you’ll find yourself far more fulfilled and at peace.

Talking about it with someone will likely result in the other “giving advice”. This requires words to communicate, so at best there will be miscommunication or the individual misses important points or clarification from being put on the spot.

“Advice” often comes from a desire to feel special and selfish nature of imposing their world-view onto you. Listening and asking thought-provoking questions is a better strategy of a friend. Because to truly pass through the stages of grief or regret (see below), you have to experience the sensation that are there and not suppress them.

Journaling accomplishes this by allowing you to explore your thoughts without the high possibility of using a crutch to validate why you should remain stuck in a stage of the grief process. It, at best, will delay you progress and insights through the natural process (again, see “Approach the sensation with a sense of curiositybelow).


As writing the thought of the book Rising Strong came to mind at how my current situation relates strongly to what I’ve learned from that book.

This is yet another instance of the importance of putting to practice what you read.

I’ve read that book about 6 months ago and regularly ponder the insights from it. I’ve read it after missing out on a job opportunity since the context was perfect to prime my mind to acquire useful information from it (my typical strategy when picking what books to read).

But here again, missing out on a housing opportunity with the same feeling of regret, I’m discovering once more how the book can be applied.

Reading “self-development” books are a waste of time if you don’t have the context to understand them from. Applying meaning is a big idea, it is what makes adversity worth wild. And meaning can only be applied from reflection. Priming your mind with a WHY ensures you get the most out of the books you read.

This is where most people go wrong and why “self-development” books can get a bad wrap. They just pick up a book because it is a top seller or recommended to them, not because their current life circumstance would prime them to get the most out of it.

For example, I’ve been exposed to the idea of “good or bad, hard to tell” for at least a year now. I’ve found many ways to apply it, but it truly took form only during a conversation with my Mom about my view of the Coronavirus. This “taking form” is to say, I had the “ah-ha” moment where things clicked, the moment of clarity.

The notion of “good or bad, hard to tell”, is shown in a fable about a farmer and his boy. The farmer has a horse run away, the neighbors express how unfortunate that is, and the farmer just says “good or bad, hard to tell”. Then the horse comes back a while later with more horses, the neighbors express how fortunate he is, but the farmer just says “good or bad, hard to tell”.

The story goes on to have the boy break his led while taming one of the wild horses, and then the military, drafting for war, skipping over the farmer’s boy due to his broken leg.

The point is that it is ignorant, immature, and naive to label something as good or bad. To do so forgoes all the forces at play in the universe.

To conclude is to claim there is no future and that events and actions aren’t influenced by past. Since labeling would ignore possibility for any future (positive) event to occur as direct consequence to or at least influenced by this current moment. It is naive and short sighted, a byproduct of being taken over by your biology and emotions.

If you want to dive deeper into my thoughts on how the Coronavirus is an opportunity, and how you can make the most of it, check out my post: 4 Ways That the Coronavirus is the Best Opportunity.

As another example of the importance of context in learning and insights consider my recent marathons.

I ran my first and second marathon within a 6 month period last year, coming from never running (albeit, I remained fit through weight training since I was 15). I pushed myself to do physically incredible training runs (e.g. long duration of intense sprints, in the heat, repeated 3 times a week, plus regular 16+ mile, non-stop, training runs 2 times a week) in preparation for my second marathon.

This push, however, was accompanied by reading David Goggins‘ book Can’t Hurt Me.

This was a book that accompanied taking my already well developed discipline to a whole new level. The insights I gain from that time in my life influenced a lot of what I wrote about in The Ultimate Guide to Challenge.

As another example, I’m currently reading “Switch” by Chip and Dan Heath because I’m currently looking to influence a large change at the company that I work for. I’m able to put these insights immediately into practice.

NOTE: I have a full time job, so if I have the time to work, read these books, write blog posts, and look for a house, all the while maintaining a regular exercise routine and proper nutrition (including cooking), so do you! The question is how badly do you want it?

Life is about sacrifice, you don’t get to choose to not have one, you just to get to choose what that sacrifice is.

The point of this tangent is that learning information is a waste of time if you don’t have the context to really cement what you learn. The context comes from real life application.

This is why spirituality insights can’t be truly appreciate nor understood until the individual has “suffered enough”. They need to be at the right point in their life for the information to have Meaning.

This is also why you can list all the facts and evidence to someone as to why they should change and have a compelling argument, but they remain the same.

Life is a mental game powered by neurochemistry. This is why effective change must start with the feeling.


Alright, back to exploring the sensations and how to rise strong from adversity.

You’ll develop your ability to rise strong with an explorative mindset. As you encounter regret or adversity, dive deep into the feelings, lean into them. Really study them. Don’t dwell on any interpretation (i.e. “I’ll never be okay”), the less thought you have, the better.

Approach the sensation with a sense of curiosity.

Make this a meditative practice. Just experience. Avoid labeling as good or bad, approach the sensations with feeling of “that’s an interesting sensation”. This is a topic that I touch a lot on in The Ultimate Guide to Challenge as well as the Physical Realm of the Life Simplified series.

Regret (and grief of any kind) comes in stages.

  • Shock and Denial
    • Disbelief: “This didn’t just happen”, “It’s just a dream”
  • Pain and Guilt
    • The pain of reality hitting you in the face. Remorse or guilt may follow.
  •  Anger
    • Frustration towards reality may lead you to lashing out.
  • Bargaining
    • Trying to fix a screw up, such as wanting to go back in time for a redo
    • A victim mindset may cause a prolong lingering here, such as “why me”, “I didn’t deserve this”
  • Depression, Reflection, and Loneliness
    • Initial emotions subside, any adrenaline is completely gone, and you realize the true severity of your loss.
    • Feeling defeated and isolated, as if in a confined space that you can’t get out, thoughts of “this is horrible” or “how can this get any worse?”
  • Coping and Reconstruction
    • The sensations become more natural, second-nature, even. A new norm has been arrived at.
    • You can begin looking at your new situation with a more rational mind, allowing for you to navigate out of the mess.
  •  Acceptance and Hope
    • What you can’t change begins to numb itself in importance, you’re able to accept the new reality.
    • Your confidence grows that you’ll find a way forward, that “everything will work out”. You may still be sad, but the wrenching pain is gone.

This is true whether lost a limb, your eyesight, a loved one, a housing opportunity, an interview, or you simply broke your favorite glass jar.

Each situation leads to the same journey through these stages, each journey will be different and will have different emphasis on different stages. Such as loss of a loved one because of an accident may result in a lot of anger.

Each stage will manifest itself differently for each person and for each situation. For example, convincing yourself that a housing opportunity will resurface by coming back on the market is a form of denial.

Now, here’s the punch line.

  • You CAN NOT skip any stage.
  • You can only improve your ability to pass successfully through each stage.

This is KEY. Just as meditation is not about having no thought, but, instead, about not letting the thoughts take control of you, letting them go when they come up. No attachment, or regret.

Hence the importance of meditation as a practice in building awareness, and thus as a practice in being able to cope with regret.

But meditation is more than just awareness, there are many kinds of meditative practices. One of my favorites is what I call “Whitespace”, where you simply reduce as much stimulus input as possible. This includes noise blocking ear plugs.

The only objective is to exist and let go. No control over breathing or anything else, just let your body be as it is, let the unconscious automated processes function on their own. Being an introvert and a sensitive individual, this is the best way for me to recharge when exhausted.

My meditative habit over the past 5 years is what I directly attribute my improved ability at passing through each of these stages quickly for my lost housing opportunity (within 2 days).

Regret is an emotion, a feeling, and like all feelings they come in waves. The abstracted idea of this is that there are stages. Motivation, happiness, pain, etc, they all come and go. It isn’t about not experiencing each stage, but about how well you can navigate through the stages.

Grief, regret, and all feelings will lose their grip after a while, but you must first let go and trust. Feelings are waves, so by definition, they will pass, despite not feeling like they will. But you have to let it run its course. When you resist its existence, then you only fuel the fire from which they burn. It’s like a cut that needs to heal, if you keep poking at it and penetrating the skin further, it will never heal, you must move awareness/attention away from the injury for it to occur. Similar to falling asleep, more consciousness is not better.

Just like anything with stages, there is the potential to get stuck. Just like how childhood is a time where there are a lot of emotional developmental periods. People tend to still be stuck in some stage, such as attachment, ultimately influencing their behaviors into adulthood (e.g. romantic partner selection, impatience, etc.)

Awareness is the key to how you avoid getting stuck at any stage, because most of the time, people don’t even recognize they are stuck. The stages are very abstract, ambiguous, and subtle.

I attribute the idea of Enlightenment to successfully progressing through all the stages of life, like completing a video game.

So, the big idea here is that you can’t avoid the stages, doing so takes the form of resistance, the ego creeps in, and you begin building a habit that will lead you to remaining stuck for a long time, if not forever.

The abstracted idea is that it’s not about having the struggle or not, it’s about how you handle it once the struggle arises.

Shorten the time you remain in each stage by recognizing where you are and taking the time and effort (e.g. journaling, meditation) to progress through the stages. It isn’t easy, it requires that you face the discomfort head-on, it takes courage.

Courage isn’t a lack of fear, it is a mastery over fear, again, not about not having fear, but about how you respond when the fear arises. This is a BIG IDEA.

Discover the Meaning

Suffering ceases to be suffering once meaning is applied.

Meaning is closely related to purpose. A part of discovering clarity of something is realizing how those puzzle pieces fit together.

Meaning is the bigger picture, it is what puzzle, all put together, is of. The puzzle is just a bunch of independent pieces, but once they are placed correctly and lined up, an image emerges.

Meaning is discovered by reflecting, this is where most people go wrong. They think experience is like a checklist, a bucket-list that you do and then check off. But to truly develop as an individual requires that you reflect back to the experience and consider how it relates to the bigger picture.

Once again, journaling and meditation are powerful tools to help with this.

Get out a pen and paper and begin writing about the sensations that you’re experiencing. The worries that you have.

I did this EXACT THING.

I sat down to write today, the time I set aside to write, and I didn’t feel like it at all. I was struggling to crystallize the thoughts related to the topic I had planned (i.e. Self-Sabotage, as alluded to in my last post on improving balance in your life).

I aim to do most things wholeheartedly, giving it my best or not at all, and I wasn’t feeling it at all. But I had faced similar struggles in the past, I knew how well journaling works for me, so I got out a pencil and paper and start writing.

The below is the EXACT words that I wrote before the thoughts in my mind crystallized and an idea for what to write about took shape.

Avoid regret and transcend grief
My real-life example of journaling  to avoid regret and transcend grief

This is in alignment with my post on The 3 Real Ways to Avoid Stubborn Writer’s Block. I had to just get started, just write something down.

I could have avoided the feelings, suppressed them and gone on writing about my planned post. Doing so may of even led to a decent post. But I wouldn’t of gave it the quality that I think it deserves.

I aim for my posts to be thorough and complete, exploring related ideas and sparking interest into big ideas. I would have left a lot on the table.

Instead, I delved head-first into what I was feeling and wrote this post.

The best mentors and individuals to learn from are not those that went through college or just obtained the knowledge. It is, instead, those who have experienced it first hand.

If you want to be rich, don’t look at those who don’t have your background and got rich by inheritance or some series of fortunate events. Those are outliers that will lead you astray. Instead, look at those who came from a similar boat, those who started with little to nothing and had to gain their wealth.

And those who you should listen to the most are those who experienced what you’re going through the most recent, so that is is freshest in their mind.

That is why I wrote this post, so that I can help those who are going through similar situations while also connecting all the dots from my own experiences (e.g. book knowledge and past similar experiences).

To go very, very deep into Meaning and the practical applications of interpretation, checkout my posts: The Ultimate Guide to Connection and The Ultimate Guide to Meaning.

Get Into the Right Mindset

There is a mindset that accompanies struggling well and handling adversity effectively.

In a sentence it is: “This, too, shall pass“.

It is the upmost belief in your ability to figure things out. That is exactly what confidence is all about, “no matter what, I’ll be alright”.

This, like all things that provide long-term results, isn’t a quick fix, it requires work and persistence. You need to acquire the experiences to train this muscle. At first it will feel unnatural, but as time goes on it will become second nature.

Realizing the impermanence of all things is a big insight, but words can’t teach it. It must be experienced. Being face down in that arena with emotions flying around shortly after the knock-down, it will be hard to see it as impermanent.

Your brain will fixate on the negative hard, that is why positive thinking and reframing is so important. The brain lets go of positive thoughts far easier. Looping on a negative thought leads to years of anxiety and depression. These illnesses are habits of thought originating from being out of control of what flies through your mind.

An explorative mindset is vital because it promotes actions based on novelty. More novelty will inevitably lead to more adversity. Exploring the unknown means that anything can happen.

Through these novel experiences, remaining aware of the sensation that you face, you’ll be able to recognize patterns easier.

This will make it easier and easier to deeply understand that “this, too, shall pass”. When you find yourself face down in that arena the next time, the feeling of “it’s just another one of those“, will come up.

From this feeling, follow that train of thought and it’ll lead you back to the practiced thought patterns of the deep realization that “this, too, shall pass”. Accompanying these thought patterns is a feeling, which is why it has to be experienced to be truly taught.

You can’t “point” to it with words, like an elegant dance move or riding a bicycle, it has to be felt because that is what it takes when you’re in the moment. Emotions will be abundant, logic is out the door, and feeling is all that there is.

The emphasis here is simply that you don’t learn this overnight, you experience it through the level of pattern recognition. Complete clarity isn’t something that just comes up on demand it requires careful navigation through the emotions that may murk up the waters when you’re face down in that arena.

It requires Awareness.

Journaling, meditation, and walking have been go to practices to help me get into the right mental state.

How can you turn the worst thing that has ever happened to you, into the best thing?


Big Idea: Effective preparation requires clarity and recovery requires awareness.

Basically: Do what you can to prepare. Act wholeheartedly. Then pass through the stages.

Regret is handled with clarity in awareness.

You can avoid regret by becoming as clear as possible on what you want and considering the obstacles that stand in your way. Clarity comes with a particular feeling that can serve as a cue for whether or not you’re on track for later regret.

A pre-mortem is a practice of journaling and deep thought (i.e. meditation) that helps you gain this clarity.

You can recover from regret by being aware of what to expect and what lessons there are to be learned. The emotions that arise after grief or regret can toss you around, it requires maturity and practice to maintain level-headedness. Journaling is a great way to come to terms with the reality and help progress you through the many stages of regret.

A mindset of “this, too, shall pass” helps you navigate through the stages and end up on the other side stronger than before.

Everything seems bigger up close, you have to take a step back to gain clarity and awareness of the bigger picture.

Returning readers may notice themes of my writing showing themselves during this post.
That is no coincidence.

The big ideas that I’ve shared in the past (e.g. Clarity, Awareness, Challenge, Intensity of Stimulus, Meaning) are what I’ve found to be the common factor amongst all my success and failures as well as success and failures that I’ve seen in others. And I’ve done a LOT of exploring in this area (I LOVE learning about practical Psychology).

For the quickest overview to bring you up to speed, check out my summary post on the Effective Living series.

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Don’t put off contemplating what the insights from this article mean, find a quiet location and think deeply about what it might mean for you. Just 10 deliberate minutes can make a large difference, set a timer, do it regularly and you will notice the changes within a few weeks. You improve your ability to think and therefore make effective decisions by spending more time deliberately thinking about the relevant subject. Consider applying journaling and meditation to see more profound changes, these are just more deliberate and concentrated forms of quiet and focused thinking. Slow down, find stillness.

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17 thoughts on “6 Ways to Avoid Regret and Quickly Transcend Grief

  1. This was brilliant and a much more insightful post than the rest of what is in my reader! I’ve realised of late that there is no such thing as moving on from grief or trauma but instead moving through it. It’s important to remember the hard times in our lives did happen- to dismiss them simply as events of the past doesn’t acknowledge the growth and inner work that has happened since. To heal you’ve got to be able to sit with the uncomfortable feelings and notice their presence, but not let them become you.

    1. Thank you, it makes my day to see my writing has value! 😊

      You bring up 2 great points:
      One: trauma has to be processed. This makes me think about abuse and anger in people, pain that does not get transformed, gets transmitted. Basically, those who got hurt often hurt others, kicking the can down the road, until someone in the line takes responsibility. Such acts of obliviousness can have compounding and detrimental effects.

      I love the idea of moving through trauma and not burying it or ignoring it. Trauma is experienced from a unique perspective, yours, which no one can replicate. Plus it provides opportunities to derive a deeper meaning for your life.
      Well said, that got me thinking 😄

      Second: sitting with the feeling.
      I’ve heard meditation referred to as a practice of “stay”. When an itch arises, “stay”, no reaction just awareness. When anger arises, “stay”.
      I think this is the fundamental principle behind how meditation improves ones ability to gain space between stimulus and response (e.g. cut off in traffic) to make still-minded decisions.

      To me, that is true power 🤔

      Wow, I love your thought provoking comments, they add a lot of value to the post.

      Your appreciation for the finer points suggests a lot of emotional and mental progress you’ve made in your own journey. It warms my heart that the blogging community brings so many great thinkers together.

      Have a wonderful week! 😀

      1. Absolutely! I couldn’t have said it better myself.

        Another point I considered recently was how so many of my major decisions were made from a place of unheal. There were situations that called for answers and couldn’t be put off. Last January I met my partner and we’ve been together ever since. There was a place I used to frequent even though I knew I needed to stop. I met him on what was my last visit and ironically, his first.

        He’s wonderful. The both of us have more than our fair share of struggles but it’s always made me wonder how we came together. He actually has a terminal illness. That was the big catch. It’s taught me a lot about patience, fortitude, empathy and so much more. He is calm in the face of mostly everything. He’s just got that innate trust that all will be okay and reminds me so often.

        The choices we make in our lives can bring ease or difficulty, good or bad- but like you mentioned in your post, nothing is this black and white. My life is coloured in a whole lot of grey tones. I know that for every crack, light will eventually find its way through. For every struggle, there is vast and priceless insight gained.

      2. Your outlook on life is phenomenal.

        I’ve got to say, that story of meeting your partner gave me goosebumps!

        A very symbolic start to the relationship and it sounds like the uniqueness of you both is serving to better eachother.

        Wonderful 😊

    1. That word has gained deep meaning to me recently, hopefully it can serve you as well.

      Thank you for stopping by (:

  2. You are a very wise person. You are indeed right nothing is in black and white. Every day teaches us that. Thank YOU for a wonderful post. Well worth reading.

    1. I appreciate you stopping by my site!

      Your kind word made my day (:
      I’m glad that I stumbled across your blog, you do wonderful work yourself.

  3. Excellent work here, Brandon. I think we face regret most often when we worry so much about worst-case scenarios happening. It feels like a best-case ending is a bit of relief. If I am faced with a setback, I try to say “good – now what?” That goes along with much of what I’ve learned here. Excellent read as usual, my friend.

    1. And excellent engagement on your end, Eli, as usual.
      I appreciate the work that you do on your own blog, you contribute well to the community.

      I love the fine-point you’ve added, a disconnect from the present moment is the source of a lot of regret.
      If not careful you can be swept off your feet and carried away in a storm of thoughts.

      Best wishes to you.

    1. Thank you! (:
      Your work is wonderful as well. Philosophy seems to be an interest to both of us.

      I appreciate your visit!

  4. No. No. My absolute pleasure to read everything you say here, the things you say on every level especially about experience because that’s life in a way. The getting there, the bringing that to it. .

Your comments make my day! I appreciate your feedback.

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