7 Jedi Mind Tricks to Overcome Fear of Regret

There eventually comes a time in everyone’s life when something you love is taken away. So, you fall to the floor crying and think, “I am falling to the floor crying,” and there’s an element of ridiculousness to it because a part of you knew it would happen and, even worse, while you’re on the floor crying, you look at the place where the wall meets the floor and you realise that you didn’t paint it very well… such is life.

James had one simple philosophy which was at the forefront of everything he did. He decided very early on in life that failure and not getting what you want are all part of the process. He decided then and there that the mistakes he had made would be dead to him. The torment of longing for what might have been was nothing but a huge distraction. He thought “I don’t do regrets. Regrets are pointless. It’s too late for regrets. I’ve done it, now. I thought it was a good idea at the time. No point in wishing I could change it.” He would never be able to take back things he never did so James would live a life of NO REGRETS.

“I’ve got a bad case of the 3:00 am guilts – you know, when you lie in bed awake and replay all those things you didn’t do right? Because, as we all know, nothing solves insomnia like a nice warm glass of regret, depression and self-loathing.”

― D.D. Barant

Life is Too Short to be Unhappy

Regret is an appalling waste of energy – you can’t build on it – it’s only good for wallowing in. The fear of regret is even worse than the regret itself because it cripples leaders, both at work and at home. Money and relationships are the two areas that consume most of our emotional and mental resources, and regret affects our behaviour in both.

When it comes to money, a famous bias linked to regret is the ‘disposition effect’ which describes how investors continue to hold on tight to losing assets. Whether it’s the stock market, a business investment, or even Bitcoin, we are extremely reluctant to sell an asset at a loss. In fact, most people hang on to depreciating assets while they continue dropping in value, hoping they will pick up again – regardless of whether that is likely.

The driving force behind this behaviour is fear – fear of regret. Fear of regret makes us stick with the status quo even when our reasoning and intuition say we shouldn’t. We are unwilling to cut our losses because, if we do, we have to admit to ourselves (and others) that we made a mistake investing in the first place. By holding on to the losing asset, we can delay the inevitable and avoid regret… for the time being.

“Four things do not come back: the spoken word, the sped arrow,

the past life, and the neglected opportunity.”

― Ted Chiang

Sunk-Cost Bias

Sunk-Cost Bias heavily influences leadership decisions in these situations because we often start new projects with high expectations of them doing well. While putting enormous effort into a project, we may gradually notice that it’s going nowhere. At this time, we may even still be able to opt out easily. However, we can find ourselves hanging on longer and longer, exerting more and more time, energy and effort, in spite of our gut feeling and common sense that it will bring nothing in return. Here, we experience regret if we terminate a project before it materialises, so we fall into the trap of irrationally hanging on to it in order to avoid regret. All of this is, of course, temporary.

Sunk-Cost Bias is often at play in romantic relationships where people hang on to partners even when they know the relationship is going nowhere. A lousy relationship that lacks love or passion can survive due to the inconvenience of terminating it… but at what cost?

Ending such a relationship ultimately forces us to admit a failure and experience regret. To avoid regret we may tell ourselves that as we have come this far with the relationship, we should give it another chance, even when we know there hardly is any hope. The same fear also keeps us away from new relationships. Fearing regret makes the status quo remarkably safe and attractive, even if it doesn’t make us happy in the long term.

“You have been given a second chance to start your life over. You can’t throw this opportunity away. If you do you will be a colossal fool. If you get the chance to do something and don’t do it then you’ll simply live with regret. That’s a worse situation than trying something daring and maybe not succeeding. At least you tried. Isn’t that what you want to show your kids?”

― Lorena Bathey

Why Are We So Easily Manipulated?

Ultimately, regret is an emotion that facilitates learning. Without regret we would find it much harder to learn from our mistakes. Regret must be painful enough to avoid repeating the same mistake over and over again.

The thing about the brain though, is that the level of pain we experience in different scenarios is counterintuitive. For instance, missing the train by one-minute triggers more regret than missing it by ten-minutes (regardless of how long we expect to wait for the next train). Similarly, a decision to depart from the status quo that later proves to be wrong, triggers more regret than making an unwise decision to remain unchanged. This means that actively making a decision to change something creates a false impression that the decision does not qualify for mitigating circumstances, making the punishment we inflict on ourselves through regret more severe.

Recent brain imaging studies have helped identify the neural circuits that are involved when we feel regret. They show that substantial activity is taking place in the hippocampus, which we know is responsible for memory. They also show that experiencing regret and being scared of feeling regret involve very similar neural circuits. The brain doesn’t know the difference between a real or imagined fear – indicating that fearing regret is actually practically the same as experiencing regret. Clearly, this can help explain why the fear of regret can be so painful and powerful.

Not all of us are affected identically by regret. People who suffer from high degrees of neuroticism are more likely to feel regret than others. This means that the tendency to feel regret is linked to the experience of anger, fear and loneliness. It is also intimately related to “loss aversion” – the tendency to focus on losses rather than gains. This means that people who are more prone to feel regret are less likely to take risks.

“Sensitive people either love deeply or they regret deeply. There really is no middle ground because they live in passionate extremes.”

― Shannon L. Alder

Challenging the Status Quo

So how can we tackle our fear of regret to get where we want in life? A starting point is actually realising how profoundly regret affects us. If we are aware that our brain plays tricks on us it may be easier to move forward. If you find yourself repeatedly failing to achieve your life goals, ask yourself if a fear of regret is to blame.

Remind yourself that while making changes always involves some level of risk, it is just as risky to do nothing. In addition, unlike anxiety – which reflects on the future – regret is reflecting on the past. So, while it helps us to learn from our mistakes, it won’t allow us to correct those we have already made.

As safe as it may feel, allowing the status quo to take over can mean that we miss out on the important things in life. Staying in your comfort zone with the status quo can often make us more miserable in the long term. Is it really worth it to just avoid the uncomfortable, but temporary, feeling of regret?

“She needs a new journal. The one she has is problematic. To get to the present, she needs to page through the past, and when she does, she remembers things, and her new journal entries become, for the most part, reactions to the days she regrets, wants to correct, rewrite.”

― Dave Eggers

You Can't Regret the Life You Didn't Lead

Fear of regret is a prison that can either have you stay with a status quo that’s not serving you or propel you to make the leap into an unknown future. Fear kills more dreams than failure ever could. Are you really letting the possibility of regret run your show? You are much more muchier than that!

What Do You Crave?

To be seen.







Constant fear of a bad choice and regret won’t give you any of those things.

“Regret for the things we did can be tempered by time; it is regret for the things we did not do that is inconsolable.”

― Sydney J. Harris

Feeling Stuck?

That feeling of “I’ll never forgive myself if I choose Option A and Option B was the better choice.” Most of the time the story ends with people staying put, sticking things out, justifying to themselves that what they need is more time. What they really need is a cold hard slap of reality so they let go of that fear of regret.

It’s not only fear of an unknown future the keeps you put but fear that you’ll regret missing out on something that happens where you’re currently planted. What if you quit a day too soon? A week? A month? Ohhhh the pressure!

“Regret is scarier than change.”

— Mel Robbins

Decision Fatigue

The need to make the ‘right’ decision is supported by these fears. Fatigue occurs when the weight of choice is too heavy to continue carrying it. This mental construct makes the fear of regret even more powerful. Let’s say you received a job opportunity in another state. Would you drown in fears like:

What if I hate it?

What if it’s awful?

What if I can’t make new friends?

What if the house is awful?

Easy. You’d make another choice and come home. Very little in this world is permanent. Staying stuck in your fear is soul-destroying. Any kind of movement forward – even if only small will begin to set you free.

“Don’t let yesterday take up too much of today.”
― John Wooden

Change Your Perspective

Your attitude towards change has a lot to do with your perspective. You can choose to focus on what if “things go wrong” or you can choose to focus on what if “things go right.” Until your perspective shifts, you won’t make the leap. Don’t be afraid of your fears. Your concern about making mistakes is there to remind you that we’re in a challenging situation. So don’t interpret it as evidence that you’re an indecisive leader, or not bold, or that you’re weak.

“The only calibration that counts is how much heart people invest, how much they ignore their fears of being hurt or caught out or humiliated. And the only thing people regret is that they didn’t live boldly enough, that they didn’t invest enough heart, didn’t love enough. Nothing else really counts at all.”

― Ted Hughes

7 Jedi Mind Tricks to Overcome Fear of Regret

We have control over one thing that we often neglect: being present. While you’re looking back at past regrets, or too far ahead into the future, you might just miss out on fully investing in the present moment. And the present where your power is – all of it! You can change both your past and future at the same time with what you do in the present. Choose to show up with your heart and mind. Or you can hand the power to what has or hasn’t happened… All choice is with you.

Focus on Process

We can’t control the outcomes, but we can be in control of the systems and processes that get us there.

Expand Your Thinking.

When we’re afraid of making a mistake, our thinking can narrow around that particular scenario. It might seem strange that you can reduce your fear of making a mistake by thinking about other negative outcomes, but this strategy can actually launch you into problem-solving mode and lessen the mental grip a particular fear has on you.

Stay in Your Lane

Fear tends to make you constantly look at what everyone else is doing. Perhaps you’re always on social media, or checking data too frequently. The problem with this obsessive behaviour is that it can result in information overload. Your mind can become so overwhelmed that you start to feel cloudy or shut down. Awareness is key. Recognise when you start doing this and limit over-monitoring or over checking. Panicked and frenzied, fear-based behaviour will cost you.

Recognise your Patterns

Identify when you’ve been hijacked by your thoughts and feelings. It takes practice. Notice when your thinking becomes rigid and repetitive; when you ruminate and repeat the same messages over and over again. A red flag is when the story your mind is telling seems old, like a rerun of some past experience. Are you starring in the same play but on a different stage? Leaders stumble when they are paying too much attention to their internal chatter and allowing it to sap important cognitive resources that could be put to better use.

Call it Out

When you’re hijacked, the attention you give your thoughts and feelings crowds your mind; there’s no room to examine them. One strategy that may help you consider your situation more objectively is the simple act of labelling. Just as you call a spade a spade, call a thought a thought and an emotion an emotion.

‘I’m not doing enough at work or at home’ becomes I’m having the thought that I’m not doing enough at work or at home. Similarly, ‘My colleague is wrong—he makes me so angry’ becomes ‘I’m having the thought that my colleague is wrong, and I’m feeling anger’. This subtle mind-trick allows you to see your thoughts and feelings for what they are: transient sources of data that may or may not prove helpful.

Smart leaders are able to take this helicopter view of private experiences, and mounting scientific evidence shows that simple, straightforward mindfulness practice like this improves behaviour and well-being and also promotes beneficial biological changes in the brain at the cellular level. Slow down and label your thoughts and feelings.

Gift Yourself Acceptance

The opposite of control is acceptance. By not acting on every thought, or resigning yourself to negativity, you have the space to respond to your ideas and emotions with an open attitude. This means they are less likely to hijack you when you can pay attention to them and allow yourself to experience them.

Take 10 deep breaths and notice what is happening in your body and around you in the moment. You may even realise just how upset you really are. The important thing is to show yourself (and others) some compassion and examine the reality of the situation.

Values-based Action

When you unhook yourself from your difficult thoughts and emotions, you expand your choices. You can decide to act in a way that aligns with your values. We encourage leaders to focus on the concept of workability: Is your response going to serve you and your organisation in the long term as well as the short term? Will it help you steer others in a direction that furthers your collective purpose? Are you taking a step toward being the leader you most want to be and living the life you most want to live? The mind’s thought stream flows endlessly, and emotions change like the weather, but values can be called on at any time, in any situation.

Effective leaders are mindful of their inner experiences but not caught in them. They know how to free up their internal resources and commit to actions that align with their values. Over time, leaders who become increasingly adept at it are the ones most likely to thrive.

“There are two basic motivating forces: fear and love. When we are afraid, we pull back from life. When we are in love, we open to all that life has to offer with passion, excitement, and acceptance. We need to learn to love ourselves first, in all our glory and our imperfections. If we cannot love ourselves, we cannot fully open to our ability to love others or our potential to create. Evolution and all hopes for a better world rest in the fearlessness and open-hearted vision of people who embrace life.”
― John Lennon

10 Most Common Regrets People Have on Their Deathbed

Don’t be afraid of your fears. They’re not there to scare you. They’re there to let you know that something is worth it.

  1. Not travelling when you had the chance
  2. Staying in a bad relationship
  3. Caring too much about what other people think
  4. Being afraid to say ‘I love you’
  5. Working too much
  6. Not playing with your kids enough
  7. Not spending enough time with your parents
  8. Never taking a big risk
  9. Not quitting a terrible job
  10. Not realising how beautiful you truly are

“There is no more disastrous mania, no more dangerous whim,

than the speculation over roads not taken.”

― Juan Gabriel Vásquez,

Developing Your Character

Your character cannot be developed on easy street. Only through experience of trial and suffering can the soul be strengthened, ambition inspired, and success achieved. You chose to do whatever it was a certain way for a reason, and you did the best you could at the time. You also don’t know if doing things differently might have turned out worse. You have no idea what the results could have been. Just because it didn’t work out right this time doesn’t mean it won’t work the next time. A few tweaks and you might even have a winner on your hands. Never have regrets for what you’ve done. It’s a complete waste of energy. Forgive yourself if you need to and move on. Regrets just weigh you down and cause you to fear trying new things.

Regrets are not even meant to drag you down. They’re valuable experiences. It may be years later that you realise something was a blessing in disguise. It may not have been pleasant at the time but you’ll probably realise how much you gained from it further down the track. Life is constantly changing in new and wonderful ways. Don’t ever let past regrets stop you from fully experiencing everything this incredible life has to offer. And, if you catch yourself suddenly saying, “Oh crap – I just did something and now I totally regret it”, ask yourself “Why?” See what you can learn from it and how you can turn it around to be a positive experience.

“It is better to sleep on things beforehand than to lie awake about them afterwards.”

–Baltasar Gracián


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