Questions: The Regrets Edition (Part II)

Great answers to Part I of the regrets column. Here are my other 5 top regrets.

6) I regret being afraid of dying. In some ways, I feel my whole life’s purpose is to finally accept (at least on a Zen-like level) the inevitability of my death. Instead, the concept so terrifies me that it has clearly kept me from being as adventurous and/or productive as I could have been. A little caution can be a good thing, perhaps, but to live without fear of death sounds so freeing. (To be completely accurate, it’s more the pain of dying than the actual being dead part that scares me).

7) I regret being shy around girls. Ok, so it’s all good as I ended up finding this great awesome girl, but oh man, I cannot begin to tell you how many times I have caught the eye of a beautiful girl and wish I had gone up to her and introduced myself, make small chat, throw her a compliment, ask her on a date, etc. but instead only watched her walk away and out of my life forever. If I had chosen not to do any of those things because I thought it would be too forward and ungentlemanly or even creepy, that would be one thing. But me … I was mostly just scared, especially of rejection, and that’s just silly. Only the rejected can give rejection its power (Oh yeah, that’s like Tony Robbins good!)

8) I regret not being more serious about my writing. Even as a young kid, I fancied myself a writer. I remember creating a whole series of short stories, including a choose your own adventure (damn I loved those), about a porcupine named Kong. I had people who liked and encouraged my work, including a teacher I had in elementary school who took a bunch of my stories and compiled them in a pretty cool bound package and helped get one my tales published in a young children’s magazine (still one of my all-time great thrills).

I continued writing short stories and small pieces throughout college, but as time passed, I grew more discouraged. I would read stories by the masters, by authors I totally loved, and bemoan the fact I could never be as good as them. I experimented with longer forms of writing, including novels, but could never finish my projects. My imagination was lacking. My vocabulary was inadequate. My characters were cliched.

But if my writing was inadequate before, it’s only gotten worse. Writing is a skill that must be honed like any other and I unfortunately have written very little over the past five years – aside from these blog posts, of course. I think I convinced myself that writing was not as enjoyable as it used to be, but I wonder if maybe there’s something more going on here.

Because sometimes I think of how envious I am of the people who seem like they know what they’ve wanted to do since the day they were born, who have passion about something and pursue it with joy AND single-minded determination, a lethal combination for success. And then I think back to how I would spend hours as a young kid holed up in my room, composing stories, getting lost in the process, reveling in my own creations, and wonder if for me writing should have been that thing, and – note the emerging theme – I just was too afraid to pursue it. That my imagination was lacking, indeed.

9) I regret not doing more for my fellow man. This one is simple. I give to charity a decent amount, but not nearly enough. But more importantly, I should be more generous with my time. On this site, I’ve often complained about the lack of compassion certain members of society seem to have for their fellow humans, and yet I cannot honestly say I’ve done much to make a difference in this world. I talk a much better game than I do, and worry I just may be more selfish than I’d like to believe. Even when I try to do something charitable, I often do it begrudgingly and with the minimum effort, like the time several years back when I along with my brother mentored an inner-city student and helped sponsor his private Catholic school education. I did so little to really help that kid succeed, and embarrassingly, have since lost touch with him and his family.

10) I regret not going to California to watch the Northwestern Wildcats play in the Rose Bowl. OK, this is a small one, but when I was a senior in college, the Northwestern football team came out of nowhere – after decades of being the doormat of the Big Ten – to shock the world with a miraculous year for the ages. In one season, they beat Notre Dame, Michigan (in the Big House) and Penn State to win the Big Ten and earn their first appearance in the Rose Bowl in fifty years.

I saw every home game that year, and even a couple of away games, and that season easily stands as one of the top three sports fan experiences in my life. Many of my college friends went out to Pasadena during the Winter Break to cheer the team on, but I was a rather broke student and decided it would cost too much money. So I went home to St. Louis and watched the game on TV with some friends and family.

What a joke. You don’t get opportunities like that often, and when you do, money should hardly ever be the deciding factor. I know the advice to save and prepare for retirement or a rainy day has its merits – and especially sounds sage in tough economic times like the current ones – but money is merely a means to an end, nothing more. Be prudent, but have fun and take advantage of once-in-a-lifetime opportunities when they arise. Trust me, you won’t regret it.

1 Response to “Questions: The Regrets Edition (Part II)”


  1. 1 nadinefeldman July 28, 2009 at 7:10 pm

    I didn’t see part I, but the cool thing about this list is that most of them can be changed. I relate to the fear of dying issue. I’m much more productive and engaged in life at 50 than I was at 30 because the clock is ticking. I could just be halfway through, but we never know.


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