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How to make big decisions the right way (with no regrets)

Get past the myth of right and wrong choices by asking yourself the right questions.

Life presents us with plenty of choices, which means we are continuously making decisions. These can be as ordinary as “where should I go for lunch?” or as head-scratching as “how should I choose a specialty for my residency?” Questions in that latter category often lead to self-judgment and uncertainty, and leave you searching for reassurance that you’re making the right decision. My clients often want to know: how do I know if I’m making the right choice?

There are a few things a person needs to make adult decisions: access to relevant information, self-knowledge, and time—among other things. The process itself will require deep introspection, and you still might doubt yourself at the end. “Am I making the right decision?” appears to be an innocent question because the answer should be so simple—you’re either “right” or “wrong”, very Manichean. But it gets complicated when you consider what “right” even means. 

In reality, the only way you can truly make a “right” decision would be to make a particular choice, observe the results, then travel back in time, make other choices, and compare them to the original. So, it’s virtually impossible to distinctively classify a decision into a “right” or “wrong” category.  

I propose that you look at this forked road with a different lens. What if you instead asked yourself: “what does the best decision for me look like?”

Many wise people have offered advice on making decisions. A common recommendation is to come up with a list of pros and cons. If you’ve tried this in the past, you may have noticed that you have far more pros for a decision you are leaning towards. As humans, we have biases and blind spots, and these give us a blurry picture of the future. 

Time gives us clarity; we’ve experienced things between the past and present that help us see a situation from another perspective. Unfortunately, many decisions are time sensitive. How can you maintain a state of lucidity while you’re taking a step forward?   

Here, I borrow from ideas of professional and personal life-coaching practices. When I work with a client, the flow in the conversation is dictated by the information they offer to the powerful questions and reflections I bring forth. Eventually the fog evaporates, awareness is achieved, and knots are loosened. The client finds sufficient clarity to propose solutions to the topic they have brought to me. This flow comes from two actions that precede a decision. They are:

  1. Ask directly for information. 

Collect information that you think you’ll need to better understand the context. Ask directly and expect an equally forthcoming answer. This will save time and will offer the other person the possibility to provide a clear response to an equally precise question. For example:

“Does this hospital offer a competitive residency program?”

This is a closed-ended question, which imposes the responder to answer yes or no. It’s unclear what the intention of the question is and this depends on a responder’s interpretation of what “competitive” means.

“What is your experience with the residency program at this hospital?” 

This is a focussed, direct question about someone’s experience. It’s also an open-ended question, which gives the responder creative space to expand on (and go beyond) the answer. 

Open-ended questions are useful to collect whole and substantial information because they give the respondents space to say what is really on their mind, do not impose constraints on their thoughts and do not inadvertently introduce biases to their answers.  When one listens and observes carefully, the response may offer at least two levels of information – the content and the delivery of the reply. Using the above questions as an example, while the residents responding might be telling you how much they enjoy this rotation at that institution, their body language may be suggesting a slightly different story (i.e. no smile, arms crossed, eye-roll). Collect as much information related to your decision by asking direct questions from people of various positions, providing you with perceptions to complement the blind spots. 

  1. Be authentic and honest about yourself.

The decision that works best is usually the one that works for you. But how can you figure out what you really want? Powerful questioning is an efficient way to dig deeply into the heart of the matter, untangling the thoughts and feelings that can cloud the decision-making process. While broad in scope, these questions are meant to get you to a specific answer by helping you better perceive your blind spots and challenging your assumptions. 

When presented with a decision, reframe the question so that it becomes specific to your desired outcome. For instance, rather than asking “am I making the right decision?” which is general and based on a value judgment (right versus wrong), try asking yourself something like: “what decision will bring me abundant opportunities to interact with patients?” A more specific question will help you focus on the elements of the decision that will bring you a step closer to discovering what you are truly seeking. Here are some examples: 

Case Study 1

Let’s see how these questions apply to a real situation. 

In a recent conversation with, Dr. Fan, we discussed her struggle to find a compatible residency program. She spent two years in pathology before switching over to family practice. Initially, her devotion to research and fascination with surgery made it a natural leap to choose neurosurgery as her first residency choice. But she didn’t match, so she accepted her second choice and spent two years in pathology. Dr. Fan was initially attracted to the intellectual challenge and extensiveness of the research in the pathology program. But the scales started to tip when most of her time was dedicated to looking for a diagnosis under a microscope rather than interacting with patients. She worked independently in a cubicle, felt isolated, and wasn’t able to serve an underprivileged community, like she had always hoped she would. 

In hindsight, Dr. Fan calmly stated that the pathology residency was not the best option. For her, the right choice lied at the intersection of her personality and interests. Dr. Fan considers this an enlightening experience. Her advice is to include multiple aspects of yourself in the decision-making process.

Let’s travel back in time to the moment Dr. Fan was making her rotation selections. What questions could she have asked to more fully explore her options to ensure they aligned with her personal and professional attributes?

Case Study 2 

Powerful questions play an important role in professional and personal life coaching. The type of question, sequence of questions, and timing of questions all serve to tease out information you may not have thought of and bring out new insights and awareness. Let’s take a look at what a coaching conversation looks like, and how these questions might support you in making a decision. 

This is an example of a conversation between a Coach and a Medical Resident that uses powerful questions to help them make a decision about their rotation choices. 

What is on your mind today? 

I’m thinking about residency. I want to make the right choices, specifically about which residency program to go into. I hesitate between three specialties: internal medicine, anaesthesiology, and cardiac surgery.

What does the “right choice” mean to you?

I am looking for a specialty where I can happily practice in for the next 30-40 years. It also needs to be intellectually challenging and rewarding. That’s why it’s important for me to experience enough rotations to know where I see myself in the far future. 

What does “rewarding” mean to you? 

It means making a difference in peoples’ lives. These fields can all have a real impact, but at different levels. In some cases, it’s life and death situations. In others, the cases aren’t so dramatic, but they nevertheless contribute immensely to a patient’s quality of life. I would also like to be able to accompany patients through their whole medical journey. 

What makes this topic so deeply important to you now?

I am at a crossroad as a medical student. In three months, I will enter clerkship where there are core and optional rotations. I’d like to pinpoint the rotations that would provide me with the greatest chances to enter the specialty of my dreams, at the university of my choice, and also to have exposure to specialties I may love but have never thought about. 

Nine months from now, how would you know that you have achieved your goal? 

I would be six months into my clerkship and have worked in a few rotations. I will have gained insights from those rotations, even if the specialties are not related to the three I’m currently considering. I believe there will be something to learn about myself in terms of what interests me the most (or not at all). This information will be additional data I can use to refine my upcoming rotation choices, or even change rotations (if possible). For example, if I learn that the operating room isn’t an environment where I feel comfortable, I won’t choose specialties like anaesthesiology or cardiac surgery. So, nine months from now, I will have learned about myself and some of my likes/dislikes to make confident decisions of rotations.

We make multiple decisions everyday, some of which have negligible impact (what kind of cereal should I have for breakfast?), and some that might veer the entire course of our lives. But don’t be afraid. Plunge into your pool of options and celebrate the fact that you have all these choices available to you. They could all be the “right” decision—it just depends on what you do with them. 


Niem Huynh, PhD, PPCC

Enquirer. Risk taker (calculated). Professional and Personal Life Coach.  Niem has explored diverse professional opportunities, from being a university professor to career advisor to graduate recruiter. Along this evolving journey that has taken her to work for various amounts of time in the U.S.A., Japan, Singapore, Vietnam, and now back to Canada, she has enhanced her professional toolbox with new abilities and skills. In addition to a diverse employment portfolio, she thrives on giving workshops related to professional and personal growth. Niem is a fierce competitor in public speaking competitions and a gentle storyteller to her toddler son. 

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