How to avoid regrets in life in 5 powerful steps
How to avoid regret often comes up in my conversations with clients.
Occasionally, it comes up explicitly with questions like, “How do we make sure I’m not going to regret this later?” But often, fear of regret lurks beneath the surface in our coaching sessions, especially when the stakes are high.
There are many situations where we fear making a decision we’ll regret later. And this podcast dives into my 5-step process for how to avoid these regrets.
Listen below or in your favorite podcast app, or read the blog to learn more!
Avoiding regrets in life during transitions
When we’re making big decisions that involve making a change, it’s normal to worry about future regrets:
“What if I make the wrong decision?”
“What if I can’t come back from this later?”
“What if something bad happens because I made this decision?”
“Will I forget why I wanted to make this change?”
And there are four key scenarios where this comes up most often, mostly around big endings and complicated transitions, like:
Moving away. Feeling worried that you’ll regret moving to a new home or to a new geographical place.
Starting a business. When you begin to take action toward going independent, freelancing, or starting your own business, it feels like a risk, and you worry you’ll regret that risk later on.
Leaving a relationship. It’s scary to let go of the familiar and a known person, even if you’re feeling unhappy or suspect you may be better suited to a different partner.
Leaving a job. Many of us develop feelings of loyalty and commitment to our jobs, so deciding whether to leave can trigger strong fears of potential regret.
Now that we understand when this fear of regret is typically triggered, let’s dig into how to prevent these regrets later.
Step 1: Know your “why” to avoid regrets
The first step to avoiding future regret is to identify your “why”–the big reason you are making this decision.
Typically when we make these big decisions, we make our “why” into something negative, by looking backward and seeing what we don’t want versus focusing on what we do. But it’s far more helpful to do the opposite.
For example, if you’re thinking about ending a romantic relationship, when you ask yourself why, you may first think:
“I’m leaving because…”
“...my partner doesn't treat me right.”
“...my partner bothers me in these specific ways.”
“...my partner won't change.”
“...my partner doesn't listen.”
But all of these reasons are about the other person and are focused on the negative aspects, which, to be clear, are all valid reasons to leave.
However, if you break up with this person and things don’t immediately feel better, lacking a more future-focused “why” can leave you with more regret.
But not feeling great right after a big transition is normal, because it can be painful and hard at first. And it’s easier to sit with this discomfort if you have a clear, positive “why,” like:
“I’m leaving this relationship because…”
“... I am seeking freedom and pleasure in this season of my life.”
“...I need to improve my wellness.”
“...I want to become happier and more joyful.”
Notice that these statements are about you and your desires, not about someone or something else. And they provide you with a compass for making future decisions.
So if your ex-partner reaches out to you, instead of immediately re-engaging, you can ask yourself more questions, such as:
“Am I on a path to improving my happiness?”
“Is reconnecting with my ex-partner part of this process?”
This allows you to connect with what you do want, versus what you don’t want, and dig deeper when things get uncomfortable.
By knowing what you want, you can more easily make an aligned decision.
It comes down to clarifying what you’re seeking in the future. Sometimes, it can be helpful to ask yourself: How do I want to feel on the other side of this?
Step 2: Identify “how” to avoid regrets
When considering the next step in making a decision, it is important to identify your "how”–the values and principles that will guide your actions and behavior throughout the process.
These values serve as a compass, allowing you to reflect on your conduct and communication during difficult times and ensuring that you can look back with pride on your handling of the situation.
For example, if honesty is a value you hold dear, you can challenge yourself to be as truthful as possible with yourself and others as you navigate through change.
If respect is a core principle, you can commit to treating both yourself and others involved with a high level of respect, even in situations that may be frustrating or challenging.
Another value that you may choose to uphold is creativity. By embracing creativity, you free yourself from the expectations and obligations of others, allowing for experimentation and surprising outcomes as you transition to a new chapter.
By determining both your purpose and your values, you have a solid foundation to guide your decision-making and actions.
However, it's essential to remember that judging the success of a decision solely based on its outcome can lead to regret. Uncomfortable periods and unexpected outcomes are common after significant decisions, and it's impossible to predict exactly what the future holds.
Instead, when doubts arise, take a step back and reflect on your purpose.
Consider whether you are still on the path towards your desired intentions. If discomfort arises, explore alternative actions that can help you realign with your purpose, rather than questioning the decision itself.
Ultimately, evaluating how you handled the decision-making process and whether you acted with integrity can provide valuable insights into your growth and progress, regardless of the specific outcome.
Step 3: Take ownership to avoid life regrets
Taking ownership of your choices is a crucial step in the decision-making process.
Once you have clarified your purpose and values, you are already on the path to taking ownership. It is important to ensure that the decisions you make are truly your own, regardless of whether they are big or small.
When you make significant decisions with high stakes, it is especially important to take ownership.
This means being accountable for your choices and not blaming others if discomfort or regret arises later on. It is easy to fall into the trap of pointing fingers at someone else who influenced your decision, such as a friend, mentor, or role model.
While it is natural to seek guidance and be influenced by others, it is crucial to be certain that the ultimate decision is yours.
By doing so, you can avoid the potential regret of relying too heavily on external influences.
Instead of saying, "I wish I hadn't listened to that person," or "I shouldn't have been swayed by that mentor," you want to be able to confidently say that you made the decision based on your own convictions.
Remember to check in with yourself and evaluate whether you genuinely want to be influenced by certain individuals or teachings.
Taking ownership means fully embracing your choices and being ready to accept the consequences, both positive and negative, that come with them. By doing so, you empower yourself to navigate challenges and uncertainties with confidence and integrity.
Step 4: Capture this moment in time
The fourth step in the decision-making process is capturing your “why,” your “how,” and your ownership over the decision.
This involves writing them down, typing them up, or even sending an email to yourself. By capturing these details, you create a tangible record that you can refer back to in the future.
One useful approach is to send an email to yourself and utilize features like snoozing or scheduling the email to arrive in your inbox at a later date. This serves as a reminder to revisit your decision and reflect on your motivations.
Another option is to incorporate your decision into a calendar event. For longer-term commitments, you can create recurring calendar reminders that include your notes about why you made the decision and the principles you stood by.
By having these reminders, you provide yourself with an opportunity for reflection and accountability.
It lets you stay connected to your original intentions and update them as needed. These reminders also serve as a way to acknowledge and appreciate your past self who made the decision with the best information available at the time.
While challenges, discomfort, and surprises may arise along the way, these reminders can help you remember why you made the decision in the first place and provide a sense of structure and framework.
They serve as a compass to guide you forward with purpose, keeping you aligned with your values and principles.
Step 5: Create an exit plan
The final part of the decision-making process involves creating an exit plan.
This is particularly relevant in the context of startups, as most startups have some form of exit strategy. It's important to consider how a venture might end even at the beginning stages, especially for projects that are open-ended or ongoing.
Thinking about potential endings can be grounding and calming, even for endeavors you hope will last a long time.
By imagining various scenarios and planning for graceful exits, you can address fears and uncertainties regarding the potential end of something you are excited about.
For example, if you are starting a startup and securing funding, consider what would happen if the company were to run out of money. Think about potential acquisition opportunities or how you would respectfully end your relationship with employees.
Similarly, if you are starting your own independent practice, envision what steps you would need to take to close that chapter in a way that aligns with your principles.
The concept of an exit plan extends beyond business ventures. Even relationships and personal commitments often come to an end.
Recognizing that most things don't last forever, it is helpful to reflect on why you are beginning, how you want to proceed, and take ownership of your decisions.
Stay accountable to your intentions, updating them as needed, and be clear from the start about what a gracious and responsible ending could look like.
Consider the example of moving to a new location. When relocating from San Francisco to Santa Fe, for instance, I carefully thought through my “why”, how I wanted to go about this transition, and my exit plan.
I considered the possibility that Santa Fe may not have met my expectations or that new aspirations to move elsewhere could arise in the future. I planned to leave and go somewhere else if necessary, while ensuring I had enough savings for potential future moves.
Having an exit plan provides structure, clarity, and a sense of calm throughout the decision-making process. Though big decisions can be nerve-wracking, this approach helps bring grounding and guidance to navigate uncertainties and make informed choices.
A final note on avoiding regrets in life
I hope the above steps will help you be more proactive while you’re considering a big decision.
Even if you're dealing with discomfort, I want to make it possible for you to look back on the decision in a positive light, or at least with clarity about why you did it, how you went about it, and the fact that you took ownership of it as your very own choice.
While regret may be a natural part of our human lives, by getting clear on what we most want and regularly checking in with ourselves to ensure we’re on track, we can reduce our regrets while still taking risks and pursuing growth.
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