How to Make Decisions You Won’t Regret 

Bright and early one morning, I planned to walk to a coffee shop to do some writing. The forecast foretold rain, but that hadn’t stopped me in the past. I plopped my umbrella in my backpack and set out for my destination. 

One block from my apartment, just as I began to cross the bridge that overpassed the highway, I looked at the sky to my left, which contained dark, angry clouds that appeared pregnant with rain. 

Walking in a drizzle is one thing. Walking in an all-out storm is quite another. I turned back, reaching the indoors just as large drops of water intermittently splashed on the pavement. 

As I made coffee in my apartment, I pulled back the curtains of my floor-to-ceiling windows. I love watching the rain, and I had a feeling I was about to see a delightfully terrifying storm. 

Sure enough, ten minutes later, torrential rain poured from the sky, accompanied by lightning and rumbles of thunder. While I might have made it to the coffee shop before the storm arrived, I would have been trapped there by the same rain. Pleased with my decision, I sipped coffee and watched the rain from the safety of my home. 

Recently, I’ve been doing a lot of looking back and assessing the trajectory of my life. I’m sure it has something to do with the approach of my fortieth birthday (something I’m really looking forward to). As I take stock of all the places I’ve been, jobs I’ve worked, people I’ve met, and decisions I’ve made, I’m delighted to report that I have very few regrets. 

In the context of the storm I narrowly avoided, I believe one of the reasons I have few regrets is because I generally make good decisions. Another way to phrase it is, I make decisions I am happy with—decisions I rarely regret. Even when I consider choices that I would have changed if I had known better, I know I made the best decision I could with the information I had at the time. Therefore, I have no regrets. 

Logic, Self-Compassion

My secret to a life of few regrets rests in my tried-and-true process. It’s important to note that I actually make decisions, something I know a lot of people struggle with. Often the struggle to make decisions stems from a fear of making the wrong choice. Here, I will suggest that most choices in life are neither wrong nor right. Neither good nor bad. Most choices in life are just that: choices. The weight of responsibility to make the best choice can lead to decision paralysis. I think it helps to work towards a mindset that the best choice for me is the one I make. 

How do we make this choice? With a combination of logic, intuition, and self-compassion, rooted in our personal values. 

Most decisions can really be made from a source of logic. Like with the storm I avoided by turning back when I saw the angry clouds. Logically, an umbrella was no match for the approaching storm. The decision to turn back wasn’t difficult. However, had I turned back and the storm decided to dissipate or change course, I still would have made a choice I was happy with, because I made the best choice I could with the information I had. 

Conversely, if I had kept going to the coffee shop, I would have born the consequences of that choice, because I decided working in a coffee shop was worth the risk of getting caught in the storm. 

As it was, my gut—my intuition—told me the choice to keep going wasn’t worth the risk. I followed logic. I also followed my instincts. No matter what choice I made, either to risk the storm or retreat to the safety of my dry apartment, my self-compassion would wait on the other side, ready to reinforce the truth that I made the best choice I could with the information and resources I had. 

To hone the skill of decision making, I suggest starting with logic, also known as common sense. If you know you aren’t great at common sense, you might need to practice by seeking guidance from people who are grounded in reality. Let your self-compassion serve you as you seek support for growth in this area. 

Intuition is a little more tricky to pin down. Cultivating awareness of our gut instincts takes some practice. While it can be a little more mystical, it doesn’t have to be arbitrary. I find intuition is often rooted in my personal values: what is most important to me. Becoming clear on our values will help us attune to that still, small voice of our intuition. Intuition is the little instinct that keeps us aligned with our values, with our deepest desires. 

From experience, intuition rarely circumvents logic, but there are times when it does. Tapping into intuition can be helpful when you encounter two options that both seem logical. 

Intuition, Values

Several years ago, I received a new job opportunity. I was working at a toxic workplace and logic seemed to tell me to take the job, which entailed moving to a new city. I even had a few friends tell me to take the job and get out. 

But something in my gut just didn’t feel right, even though many of the logic signs seemed to be pointing in that direction. I believe my intuition was telling me I wasn’t yet ready to leave the city I was living in and that the job opportunity wasn’t a great fit for the next season of my life. 

I really wrestled with this choice. In the end, I trusted my gut. Over the next year, I ended up leaving the toxic workplace for a job closer to home. While there were a dozen reasons why waiting and taking a different job turned out to be a choice I was happy with, one big one was the onset of the pandemic. The job I ended up taking made the transition to working from home seamless, while the job I turned down would not have been as conducive. 

I had no idea the pandemic would happen when I made the choice I made. But some mystical connection communicated between the universe and my instincts. In that situation, I made a choice that felt right to me and I ended up being happy with the choice. At the same time, I know if I’d taken the first job opportunity, I would have finagled that decision to work in my favor. I might have wondered “what if?” (as I still sometimes do about not taking that job) but I think I would have been happy with that decision as well. 

Neither decision was right or wrong. Good or bad. It was a decision. On the other side of that very torrential period of life, my self-compassion supports me, reinforcing that I did the best I could with the knowledge and resources I had. 

That’s the best choice we can make for ourselves, just doing the next thing that makes sense. We take stock of our resources, assess what seems reasonable. Then we sit with our intuition. Maybe we take a moment (or a few moments) to ask, “What do I really want? What’s most important to me?” With our options, logic, and values before us, we make a choice, knowing our self-compassion will be waiting on the other side for any of those persnickety “what if?” moments. 


You might enjoy this episode on intuition from Michelle Rios.

Katherine Spearing MA, CTRC is the founder of Tears of Eden, a nonprofit supporting survivors of spiritual abuse and is a Certified Trauma Recovery Practitioner working primarily with clients who have survived cults, high-control environments, spiritual abuse, and sexual abuse. She also provides specialized trauma informed career coaching, as folks with trauma often need extra support for interviewing and networking. 

Katherine is the author of a historical romantic comedy, Hartfords, a novel that challenges gender roles in a patriarchal society that will appeal to fans of Jane Austen. Her next book on Spiritual Abuse addresses the survivor’s recovery journey, coming in 2025.

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