I’ve been wanting to sit down and write a regular blog about interesting questions to ask myself, and some people do it daily. But a daily blog is a bit of a grind when the real intent is learning, so I’m going to ask myself seven questions a week. Let’s see what I can learn about myself.

001. In what area of your life are you most successful? What lessons can you learn from that?

An interesting question right off the bat. It goes to the heart of who I am — not in what I am most successful at but in defining what success looks like. It isn’t a hard one for me, ever since I was 33/34 and emerging from my tadpole years of self-reflection, I’ve always known what success looks like to me. Being true to my self and, where possible, achieving my potential. It’s inward-focused, as most of my thoughts are at first glance. The lessons that derive from that are obvious — I need to continually reassess my behaviour, my motivations, my actions, to know if I am being “me”.

002. What words of advice would your 80-year-old self give to you now?

I think my advice would be a further reminder that inward-looking leaves you alone. The most important roles I play — son, husband, father — are all by their nature outward-looking. They require me to be present, not to simply analyse.

003. What has been the main cause(s) for feelings of unhappiness throughout your life?

I think that depends on which part of my life I reflect on. When I was growing up, starting my life, building a new life in Ottawa, I struggled with what I wanted others to do or be, or how I wanted them to treat me, not based on who they were but on who I wanted them to be. Family, friends, lovers. If I had to articulate it, as I am forcing myself to do now, I think the closest I can come is to say that I didn’t accept myself to be myself, so I didn’t know how to accept them to be themselves. I struggled with disappointment, not for people not living up to some high standard or anything, just more people not behaving the way I wanted/hoped they would.

004. What has been the main cause(s) for feelings of happiness throughout your life?

There’s no revelation or insight there, it is the same cause for most people. Making connections to others. Family, friends, my wife, my son. Yet running a slightly distant second is connecting simply with myself.

005. Make a chronological list of the moments that made who you are today when it comes to love and relationships.

Wow, now THAT’s a question.

• Being rejected harshly in eighth grade and being alone through high school –> It helped me start to understand my nature;
• Realizing that I wasn’t strong enough to end things with a woman –> I realized at the time that I was afraid of being alone;
• Reverting to lesser versions of myself in stressful situations –> I wanted to fit in more than I wanted to be myself
• Three “pre-dates” one summer in Victoria where their intentions were not clear to me until later … one wanted a friend and never thought of another explanation; one wanted more but I was only ready for friendship; and one wanted more but really just needed a male friend –> I realized that I am not very good at reading people if I’m potentially interested in them;
• The start and end of a long-term relationship –> I was initially only interested in friendship, and it probably should have stayed there, as we weren’t very compatible long-term, but life intervenes with no regrets. But the break-up made me realize that I wasn’t as weak as I thought I was, and we remained friends. I also came to realize that I view love different than many people. I don’t do break-ups. Each person who has entered my heart still resides there. Not everything ended well, some things done to me are not laudatory. Yet they have no bearing on the feelings I had, I don’t recast the entire relationship in a different light, I don’t second-guess my intentions or what we had or didn’t have. I realized, for me, perception was reality. If reality wasn’t my perception, it doesn’t really change much. The feelings were real, and they reside in my heart still. I don’t bear any of them ill will in any way, with the warmth of an old friend, not romance. It of course runs way deeper than this simple bullet, but it helped me with some of my rules. Trusting others to be who they are, not who I want them to be, for example.
• Saying goodbye to my father and helping my mother afterwards –> I realized that with change comes new boundaries that have to be drawn, and I changed my role in the family from peace-maker to merely member.
• A four-year period of self-reflection, where I deconstructed both my own psyche and my friendships with a large number of women over the years. I was friends with them, yet I wasn’t interested in them romantically. I would look at various ones and try to figure out — what was it about them that interested me in being friends with them? Which parts of them did I like that I would want to see in someone else, if I was to date? What traits or characteristics did I find “attractive”? –> Again, I realized that not everyone looks at relationships the way I do. Or more accurately, I don’t look at them the way most people do. People assumed if I talked about what I liked about person X, it meant I wanted to be with them. I didn’t…I was considering people LIKE them, not them directly. Hard to explain, and at the time, I didn’t do a very good job of it when people asked what was on my mind.
• On three occasions with different women, none of whom I was interested in, I interpreted their behaviour pretty accurately and at one point, people were joking that I was psychic. –> I realized that if I paid attention to people’s word choices, verbal inflections, and body language, I could often pull disparate bits of information from a variety of sources and come to a realization that didn’t seem linear. But only if I wasn’t personally involved or interested — if I was, that ability was completely blocked.
• A year of implementing the prototype me –> I realized that what “works” for modern day relationships i.e., drama rituals, casual approaches, etc., didn’t work for me. I don’t do drama, and I don’t do casual. I also realized that if I was going to be true to me, I had to say what I felt when I felt it, not waiting for the right time or for someone else to catch up.
• My first non-date and date with my now-wife –> I realized that all the analysis in the world cannot predict life intervening.
• A boat ride date with my now wife –> I was enjoying a simple boat ride, the sun was setting and reflecting off her hair, and I suddenly realized that the new me, rational and self-aware, was in love with her.
• An afternoon in the Bahamas playing board games –> My now-wife but then-gf and I were forced to stay indoors on one of our vacation days as it was raining out and not much to do, and we had a blast anyway just hanging out together.
• My wedding day –> Of course, for obvious reasons.
• Every day of her pregnancy and the first two weeks Jacob was in NICU –> A roller-coaster ride of epic proportions.
• Saying goodbye to my mother and acting as executor of the will –> Again, my role in the family changed again, and I realized that as important as family is, I have another family — my wife and son — and they are more important than the rest. I can’t be who that family wants me to be or pushes me to be while being who I want to be with my new family. There were parts I had to let go.

006. What has life been trying to tell you over the past few years?

It would be facile to say simply that I’m getting old. More pointedly, it is that I have fewer years left than I have already spent, and if I want them to be something unique, I can’t simply drift along. Not majorly, not a mid-life crisis or anything, I am far too self-aware or arrogant to feel like any impending crisis of faith in myself is looming. It is more, I think, simply that I am looking ahead to retirement in five years, and while I enjoy my work generally, I don’t want to do it forever. I will hopefully retire when I am eligible, not stick around because I have nothing better to do. I have lots of ideas for my retirement, even though I strongly suspect that I haven’t yet found my passion to explore in retirement. Writing will continue, I hope, maybe just in the form of this website.

007. What is the role of most news media in shaping our beliefs for this world? Is it a message of love or one of fear they share? Reflect on that answer.

Lots of people find this question highly profound. From the Medium is the Message to the role of Fox News, deep troubling “issues of society” are at play. Or so I hear. To me, it is more like a triangle between society, religion and government. Society is always in constant flux, the cutting-edge of change, and I think news media is constantly trying to understand it, and share the info as soon as it can. Is it “shocking” more than “warm fuzzies”? Change often is. There are constant battles on the margins. Religion, by contrast, tends to offer a core stability, something that is NOT changing with the times. Deep roots to hold fast during storms that rage around a church, but not in the church. And thirdly, government, which tries to manage the worst aspects of change, to reduce the negative effects of chaos, to keep the screams down to a roar, where it can. News media doesn’t exist in isolation as a randomly charged ion…it interacts with the rest of society, bounces off it and government, identifies areas where all the forces in that environment are colliding. The latest news, so to speak, is the latest collision. Assigning a message of love or fear to its role is too anthropomorphic for my tastes.

An interesting list of questions. Which one would challenge you the most to answer?