In Pursuit of Understanding Sadness

15 min readFeb 18, 2022

I try to be an honest and forthright person (emphasis on “try”), but there’s always this one situation where I am tempted to lie and that when someone asks me the often innocent, but rarely terse question: “How are you?”

“I’m fine! How are you?”

Now, don’t get me wrong, often I am in a pretty good space (or, at least I like to think that I am), but there are also days that I am down about something that may have happened or that I am experiencing. And, when people try to check-in with me on those days, my first instinct is to keep whatever sadness I am going through to myself.

Why would you not tell people that you are feeling sad?

Well, because it’s kinda what we’re supposed to do, right? Throwing your shoulders back and persevering through whatever the emotions or feelings are, is kind of a cultural thing here in the US, is it not? Well, at least it was for this 80s baby.

There’s been a lot of study of this over the last few decades and even more given the pandemic that we all have experienced in some way, shape, or form. Our silence about feeling sad blocks us from making meaningful connections with the people around us (ie- family, close friends, therapists, even total strangers). Today, I wanted to explore the idea of sadness and what it means to be sad and how to become better at it. I wanted to write this in a very nuanced way in order to drive out some of my own questions and that this sort of Q&A with myself can also be a sort of a simplistic way of understanding something that I think is quite terrifying to admit and also balanced enough that someone reading this might also walk away with something noteworthy for their own journey or encounters. Here goes!

So, in my late 20s to early 30s, I had become enamored with this idea of “success” and achieving enough things that would not only keep me from returning to poverty, but also allow me to make friends, get married, have children, own a home, etcetera… etcetera… In my mind, I had done everything that society would define as living a life deserving of success. I had served honorably in our US military, I graduated from several outstanding institutions of academia, I had just got an engaged, I volunteered on several commissions and boards in my community, and I had just got my 1st job paying me a six-figure salary. My thought was that with these things under my belt, I should only be getting happier and living more abundantly. However, I wasn’t really getting there, nor did it seem as though I was ‘living abundantly’. I had moved to a new city and chose to live downtown (which is a little more stressful when you consider all of the people and things that go on within a city environment), I had this new job that was entirely new in all facets and shown to be incredibly stressful for me, I was planning a wedding and honeymoon with my fiancé at the time, who also was experiencing some stress from the move and the new lifestyle, and I was living at a fairly fast pace, where weekends came and went pretty quickly and often involved a lot of partying and drinking. It didn’t take long for those things to create this question of “is this it?” in my mind and lead me to experience what I think initially was a bit of sadness (and much later what I am now considering to be depression). I would sometimes feel guilty and ask myself, “how can you feel sad when you have so much to be thankful for”? I was being introduced to so many wonderful people, exploring new and exciting places that I had never seen before, and even learning so many new and exciting ideas about business, culture, and the world we live in — how could someone possibly feel guilty or sad about that!?

And, yet, I did.

I had also experienced the sudden loss of family and friends to circumstances out of our human control. I also had met immigrant families who were escaping the horrors of their homeland and praying to reconnect with their families across seas or borders. I had met people who had lost jobs because their skill set had been made redundant by the advancement of technology and would have to retrain or find another place for their skill set. I met people who had suffered bad breakups or had been left at the alter. I even met one couple who had lost a child during labor and were grieving because of the likelihood that they might not ever be able to have children. And, yet, in the face of all that — not once did I think that it was ok to ‘be sad’. I kept believing that I was supposed to find some magical object that emotes happiness and everything would be cured. I thought that maybe there was something that I was not doing that was alluding me in this quest. And, “quest” is a pretty appropriate word for what I was feeling as it often felt like this holy grail that I was determined to discover. It never crossed my mind that maybe sadness was what I was supposed to feel and that maybe happiness wasn’t what I was supposed to feel right now and maybe sadness was the thing that my intuition was trying to tell me I should be experiencing right now. This seemed culturally unacceptable to me and counterintuitive to my own beliefs.

So, recently, I started questioning that very assumption and asking the question “well, why”? Why is it unacceptable to be sad? Why should I shutdown one entire human emotion that we all have? I believe a part of the reasoning is that there is a real reluctance in society to consider this question or to assume that this question is one that is only unique and personal to me. I think there is this real reluctance to be curious about sadness and I wonder if this premise still serves us well as a society. I wonder if the impact that this mindset has on us, and how we could be living a little better in being able to embrace our sadness in a healthier way.

What’s your first thoughts of being sad?

Growing up, I would say that I had a complex visual of what being an adult was all about. My parents separated and later divorced around the age of 5 or 6 and that forced my mother and I to move around a lot. The men that were introduced into my life were complex and had many traumatic experiences that they were not prepared to deal with. They had some poor behavioral mindsets and conceptions about manhood and what it meant to be in union with themselves, others, and society. I was raised primarily by an esteemed pride of black women who themselves were nuanced in stigmas of being black women in a culture that didn’t see them as overcomers or worthy of acceptance, but as welfare recipients or irresponsible. I wasn’t raised in violent or harsh conditions as displayed on television at the time, but there was an unwritten understanding of the neighborhoods I lived in and how to move about within them that you learned early as a child. I also spent about twenty percent of my childhood in Europe during the time of The Wall of Germany and witnessed its physical dismantling around the age of 11 or 12. In my house we talked about the challenges of our situation, but there was always this idea of perseverance and determination in the pursuit of something greater that was in store for me. Validation for this concept was through our [family] collective gains — academics, sports, doing my chores, following instruction well, being a people pleaser in uncertain environments. For me, these were things that I thought at a very early age that if I could just do these things correctly, then I could make my home and my life that much better. As I became an adult, I realized how much of my childhood I missed out on because of the necessity to be more responsible for our household. And, to be honest, this made me quite sad as I got older. And, I think over time, it has compounded into a state of being that has made me forward looking instead of present with the current time and space I am in. I inebriated myself with the pursuit of things that I thought would address those things, but really didn’t serve me well and often I wasn’t emotionally prepared for. In hindsight, I believe those things just distracted me from where I was at in my journey and became more of an unnecessary turn than a steppingstone. I think my immaturity and lack of compassion for myself didn’t allow me to grieve and be present with my sadness in the loss of that time in a healthy and thoughtful way.

So, what is sadness you are addressing?

I would say that sadness is a temporary feeling that we feel on occasions when we’ve been hurt or something has gone awry in our lives. It’s a message from our bodies and minds that tell us that we need to stop, reset, observe what’s happened, and process how to move forward constructively and presently. It differs slightly in manner from anger, but not handling it correctly can lead one to isolate or become withdrawn from society and that can lead to depression and other chronic forms of dementia. I think sadness can be an awakening of sorts, which is different than depression and I want to make sure I’m being clear when I say this — but, I think we will all experience sadness at some point, but if we don’t know how to handle it, I personally have found that it can be incredibly isolating. I think the idea that we ‘shouldn’t talk in a sad or defeated way’ is a really limiting way of addressing the feeling and studies show that it can make the feelings more intense rather than resolving them. A way of reframing this ‘temporary’ feeling is to sit with it and be present with it. Studies show that sadness has the affect of making us more detail-oriented, focused, grateful, generous, and actually its quite creative. Think about it — when we are happy, we don’t seek to change anything and we kind of go on auto-pilot for the most part, but when we are sad, it’s almost like a problem-solving mechanism and we begin thinking about our ‘next-steps’ or why those things occurred in the first place.

Does sadness only occur when devastating things happen?

I don’t think so. So, for example, I remember when I got accepted into business school back in 2011. I was so excited, because I was coming off the 2010 election cycle that saw two candidates I was actively supporting and volunteering for lose their race and — I, too — had also lost an election of my own just months before. Having enough of losing and working in what I believed to be at the time in a very unappreciative industry, I believed that going to business school was going to put me on the upward path to financial mobility, entrepreneurial aspirations, and personal stability. Not only that, I thought leaving would give me a change of scenery and an opportunity to start over. However, when I got to business school, that wasn’t the case as I often felt out of sorts. I had many friends but I still didn’t feel like I belonged at the program and that always saddened me. Then, I thought, “well, when I get this job offer, then I’ll be happy.’ However, even then I was not fulfilled and was left with the feeling “Is this it?”

When I got to these goals and realize that it was sort of anti-climactic, I felt a feeling of ashamed and ungratefulness that I don’t think I realize was associated with doing something that many would have thought to be a ‘good’ thing. There’s this term called “arrival fallacy” where its similar to finishing a race or completing a really difficult puzzle and this malaise or “meh” kind of becomes the feeling. Its underwhelming and can also be kind of disappointing. The term was originally described to focus on big goals and milestones, but the definition could easily apply to getting a promotion, finding a new home, or having a child — the more typical things that many of us will experience in a lifetime that can happen and then once they’ve been obtained, can make us feel quite flat. I think I can apply this to when I got my 1st corporate job out of business school where I was excited about the opportunity initially, but once I got there and life settled in — it really wasn’t something I was incredibly excited about any longer. I felt this sense of urgency to do something about it, so I began studying everything I could about the new city, the company, and even some of the leaders within the company. However, at the end of the day, I felt like I did the wrong thing and was kind of ashamed that I wasn’t having the happiness and success that I thought the job would bring me. This story can apply to many things (ie- relationships, parenting, etc), but I think the thing that is important if you find yourself in this space is to talk about it with someone and believe that you aren’t alone in those feelings because many people have had these moments and realizations.

Experiencing sadness is often uncomfortable. Not just for the person going through it, but also for people around you. I can’t help but think about the character Miranda Carroll in the HBO series “Station Eleven” having a moment of complete sadness in Episode 3 at the thought of hearing her ex-husbands death and the impending doom of the world with the ongoing virus devastating the globe. I think this is particular to people in the US, where there is this emphasis on success and mission completion over personal well-being. Often, well-being is seen as something that is of the individual, when that is so far from the reality of the situation. I believe we are introduced and then educated out of our feelings as children, because as a society we don’t value sadness nor do we see the ‘good’ grieving. We’re taught to shutout our fears and our pains for fear or what others might believe it represents or for peace of others who, too, might be experiencing certain emotions in silence. I think that what happens is we don’t learn to deal with certain emotions well and then as adults that lacking shows up in a very human way. Think about the time we are in now where we are talking about things associated with being a part of humanity — the color of your skin, your beliefs, your choices. We haven’t talked about them in ways that are conducive or productive because we can’t deal with our emotions and feelings when told something contrary to our own values or culture. I think we also see this in the way our children are being raised. Due to the many different elements that go on in the communities we live in, we don’t allow our children to do the things which children do which is explore and be curious about the world around them. This, too, can have a detrimental effect on the way our next generation grows and builds resilience and understanding around the enormity of life.

Are we afraid to be sad?

I think the better question to ask is what’s the extrinsic value of being sad? There’s no business case for it. It’s not appealing. And, there’s no desire to sit with it and examine it. There’s no intrinsic value from you being sad, and yet, the choice to do just that is the hardest thing one can do. I’m not talking long term things like depression, I’m talking about just sadness, where you feel alone or not quite yourself. That can be scary feelings as often that means we have to be alone, and we aren’t equipped for that here in the US as we tend to do many things together and in part with our community. Perhaps, that’s where technology is having an impact on our society and causing this increase in depression over the course of the past 5–10 years.

Are you a failure if you are sad?

I felt this way when I lost my first job. Now, to be fair, I come from a community, where men not having a job or gainful employment is seen as a weakness and character flaw, so for me to lose that job was devastating and went against everything I had been socialized to believe. And, you must remember that we are educated not to do anything that will ‘ostracize us from the group’. Thus, to go through something like this (which is common in life), was something I was not prepared to deal with and thus I was disappointed that I lost my job and felt shameful that I didn’t have an answer to it. On top of that, I had shame about feeling shameful about losing my job. That could be the Midwest culture in me where we apologize for just about everything, but that feeling of apologizing for being a mess after a job loss was also a peculiar thing and something that I recognized as an inability to deal with what I was feeling at that time. No one should apologize for simply feeling. Not expressing, but ‘feeling’.

Can we be sad better?

My son was feeling very sad one day. My son has the amazing gift of autism and for him and others on the spectrum, that can be quite isolating at times due many different things. I’m not sure what caused it or what he was experiencing, but he was able to communicate to me that he was sad on that day. Naturally, as a parent your first thought is to try and fix it, but I didn’t know what to fix or even what was going on. So, I just asked him what he needed, and he said he just needed ‘a hug’. So, I sat there with him and just hugged him as securely as I could until he kind of gently pushed me away. He laid on the floor with his blanket and sucked his thumb and I just laid there with him. I didn’t say anything or try to communicate anything profound to him. I didn’t make any jokes (as I am known to do; although I did take a picture of us lying there) or hand him any toy to take his mind off what he was going through. I just stayed right there with him on the floor. Eventually, he got up and went to his train set and started playing and offered me to play along with him. I never forgot that moment because it was like everything had changed for him and he began confiding in me with more of his emotions. It was a game changer in our relationship, and I was so moved that he was able to recognize what he was feeling at such an early age. When I was taking care of my son, I really didn’t have anyone to talk to, because most people wanted to fix it, provide judgement on what I was feeling through their perspective, or simply tell me “You’ll be alright”. I also probably put off some people with my demeanor as often I just really didn’t have much to say that was positive or saw something greater. I think what I needed was just someone who would just listen without interruption and without judgement. Who would just “lay” in that feeling with me — making the connection.

Many of the things we do to fight sadness (or our feelings) do more harm than good. If we are taught that sadness is bad, then we might try to disassociate from those feelings whenever they arise through some means of stimulus. Eventually, by disassociation, we become less connected with the people and things around us and that tends to lead to depression. When I was in college, I anesthetized myself through staying busy and overworking through volunteering and exercise. When I got a little older it was alcohol and sex. And, when I lost my job, it was through video games and late-night eating. I think what happens is that the sadness doesn’t go away but comes back even more aggressive. Oddly, enough, I never thought about getting rest when my son was an infant. I would take that time to do laundry, cook meals, or clean up. I would never take that time to just rest because I didn’t want to think about the sadness. I think the answer lies in our vulnerability. As an early parent, I didn’t want to let people know that I needed help. Or, maybe it was that I felt folks would see me as incapable of also being a parent as well as “jobless”. Thing is when we are vulnerable about what we are experiencing and about what we need, we allow ourselves room to grow beyond what our current feelings might be. When we hide them and tell the world that “I’m fine” when we are not, the person you are telling that to might not know that it’s a lie, but you most certainly do. And, the worse thing you can do is lie to yourself. Generally, if we are emotionally reactive to something or someone, it is because we are being reminded of something painful, raw, or unresolved in our own lives that has nothing to do with that person and everything to do with ourselves. In these areas, we are going to struggle to admit the truth. And, how can we be honest with others when we first aren’t honest with ourselves? And, if we can’t be honest with ourselves, how can we have meaningful connections with one another? Being honest requires deliberate effort daily, as well as tolerating some painful realizations that if reframed can also be an opportunity to grow. But, that’s tough. Thing is we don’t have to drop all of those nasty realizations in one day. I think giving ourselves grace and empathy allows for us to get there in God’s time. But, it starts with being in tune with what we are feeling. And, often, what we tend to be feeling has truth.




Growing up, I always thought of ways to change my lifestyle. That, and how I could listen to hip-hop without my mom finding out.