Asking Yourself the Hard Questions

Kyle Harris
6 min readAug 10, 2021

Mindfulness, self-reflection, and introspection are beautiful things when done correctly. They can also be mundane hoops to jump through when they are task oriented or forced. The problem is true mindfulness, self-reflection, and introspection is really hard. On the surface it’s difficult for us to slow down enough and take the time to truly embrace a meditative state that allows for actual mindfulness. The fact of the matter is our society and lifestyles have become so fast and reactive that we don’t know how to slow down and actually process information. We are constantly bombarded with information and we have trained ourselves to become incapable of actually processing the things thrown at us. Furthermore, we are in a perpetual state of fight or flight, living through our sympathetic nervous system. The physiological and psychological changes and ramifications of this are so impactful we’d need volumes to discuss.

However, it’s beneath the surface where the true difficulty of mindfulness, self-reflection, and introspection lies. The true depths of getting intimate with yourself is terrifying. One of the most amazing and tragic skills we have as human beings is the ability to create facades that protect us, not only against the outside world and others, but against our true feelings and emotions. We are architects of epic proportions when it comes to creating masks that hide our insecurities, vulnerabilities, and true self’s. These masks provide us with what we feel are strengths. They provide false connectivity, acutely, and within the framework of what we feel life’s current situations require. Yet, what they truly do is create greater and deeper insecurities that actually build walls around our ability to be vulnerable and instead create greater disconnection, with ourselves and others. There’s a reason our society has been struggling with an increased rate of mental health disorders for decades. We’re running away from ourselves because we’re terrified of vulnerability and disconnection.

Here’s the thing, in order to feel connected, build connection, and develop meaningful relationships, we need to increase vulnerability. But, vulnerability starts within. If we cannot get vulnerable with ourselves, we will never be able to truly become comfortable being vulnerable with others. Personal vulnerability is a ghastly proposition that requires deconstruction through mindfulness, self-reflection, and introspection. It requires you to ask dangerously, difficult questions that you may not like the answers to. Most people cannot get past surface level answers to these questions, thus they won’t be able to truly develop the internal vulnerability they need to establish a foundation of personal growth that allows for the vulnerability needed to truly create connection that leads to long term meaningful relationships.

Question 1: What is your identity (Who are you)?
This is not asking what you do or what your trade is. The answers to this must surpass superficial labels like: spouse, parent, teacher, coach, farmer, builder, etc… These answers should be the cornerstones to who we are as people. They are the foundation of how relate to the world, how we relate to people, how we build relationships, and how we handle and grow from adversity. If the most important labels of your life were removed, would your identity change? If our identity is truly and wholly intrinsic, it should not change. If you were stripped of your occupational identity, your actual identity should not change. If you strip away other labels like spouse, parent, son/daughter; who you are should remain intact. If your entire identity is defined by superficial labels, you have built your identity with no concrete foundation, it is a house of straw sitting on loose sand.

Question 2: What is important to you; what values do you prioritize?
These can change, and maybe they should change. Maybe when values and priorities change and importance shifts that shows growth. Personally, I think we too often times marry our identities with what we feel is important in the present. When we do this, and values or priorities change because of uncontrollable circumstances or natural life progression, our identities can become fleeting and that can lead to existential crisis. This is why identifying who we are, with intense mindfulness, self-reflection, and introspection is so important. Spending time thinking, journaling, and documenting your priorities can create perspective. Perspective can lead to being more intentional. Intentionality can improve performance and satisfaction. Without reflecting on what is truly important to us, it’s difficult to create priorities, which can lead us to spinning our wheels and missing out on some of life’s greatest offerings, including meaningful connections. Knowing your priorities also allows us to come to terms with which aspects of our lives and personalities we may be initially more comfortable or apt to allow for vulnerability. If we choose and commit to a priority we will far more likely to take open ourselves to the vulnerability needed to maximize those priorities and the relationships they involve.

3. What are your goals?
Reflection and introspection can be highly beneficial in this process. Goals can encompass our careers, occupations, and hobbies. It’s far more important, though, to be mindful of creating relationship goals and goals that center around how you want to design your life. Questions like:
— What do we want our life to look like?
— What types of relationships do we value?
— How do we go about obtaining the life design we want?
— What aspects of my identity do I need to change to build the relationships I want?
— What types of people do I want to build relationships with?
— How can vulnerability aid in meeting my life design & relationship goals?
These types of questions are not easily answered and they make weeks, months, or years to figure out. It can be an arduous process, but I assure you, you are worth it.

4. What do you want your legacy to be? How do you want people to remember you?
As morbid as it sounds, we are not on this earth forever. Father Time is undefeated as they say, and we will all expire. When your time comes, what did you produce? Existential questions like this can be difficult to wrestle with, but mindfully meditating on such questions can help us make sense of all the aforementioned questions. Superficial, material legacies won’t fill your cup, and they certainly won’t fill the cups of others. In order to leave a long lasting legacy that can benefit generations we must develop the comfort to be vulnerable. Vulnerability builds intense connections with others. Those connections and relationships allow us to grow and reap the rewards of others around us. They also allow us to build perspective in what is truly important, which in turn can help us create an impactful legacy that others can use to improve their livelihood and well-being. Tackling the difficult questions allows us to challenge ourselves and others for continual personal growth and personal growth allows us to get more comfortable with vulnerability. This cycle can be highly rewarding and beneficial in fostering the ability to connect with others. Connection is what provides meaning in life.

There are certainly more questions we can wrestle with and reflect on, however these four questions and some of the sub-question examples are probably overwhelming by themselves. Incorporating periods of mindfulness, reflection, and introspection can be difficult, especially in our fast paced world. Doing so will be uncomfortable. It may even be scary. You will struggle with blocking out distractions, and if you’re like me you will at first feel like you are wasting time that could be better spent “producing” or “accomplishing” something tangible. I promise you that if you set time aside each and everyday, even if it’s just for 5-minutes, you will get better at mindfulness and introspection.

Set time aside each day to reflect. Start small. Take a gratitude inventory every night before bed. Think about the things you look forward to during the day when you are in the shower. Reflect on the positive things that happened to you throughout the day on your drive home. Once you develop some habits, begin asking yourself some of the questions discussed in this blog. Start a small journal in a notebook, computer, or on your phone. As you develop skills needed to truly be mindful, stretch your introspective moments by increasing the time and intensity of your self-talk and self-reflection. Begin to tackle the difficult questions one at a time. Do not judge yourself by your answers and be open to changing them as your instincts begin to more naturally surface. Choose some priorities and list some ways in which you can model vulnerability. Choose your most important and fruitful relationships and challenge yourself to be more vulnerable. As you morph into a more vulnerable and mindful human, reflect on how much deeper and more satisfying your relationships become.

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Kyle Harris

Phys. Ed. Teacher, Hitting/Pitching Instructor & Group Training Coordinator @ Bob Harris Baseball School, MS AES & LA, NASM-PES