You Won’t Be Sorry

By Troy Headrick

During this past week, I went back and reread the autobiographical blurb I have posted on Pointless Overthinking’s “Our Team” page.  It had been a long time since I’d looked at what I’d penned about myself.  I wanted to see if it still felt true.

I’d forgotten that I’d written about myself using third-person pronouns.  I suppose it made sense, though, to have referred to myself as “he” and “him.”  That’s very much the way I am.  I’m the sort who stands to the side, very inconspicuously, looking, making mental notes, playing the part of objective observer, and then trying to come to some conclusion about what I’m looking at.  I take this role even when thinking and writing about myself.

I was especially intrigued by the last sentence of my little autobiography:  “His ultimate goal is to live the uncommon life.”

Yes, that’s very true of me.  I suppose it’s always been true.  For as long as I can remember, I have been the sort who wants to be challenged and to swim against the current.

I can share an early example of this.  When I was about eleven or twelve years old, I decided, one day, likely entirely out of the blue, that I wanted to learn to juggle.  I had several tennis balls on hand, but this was long before the internet and Google and YouTube.  No one in my family knew how to juggle, so there was no one to ask for advice.  It was clear from the very beginning that I’d have to teach myself.

I had no idea how to start, so I began to experiment.  I tossed one ball into the air and caught it with the same hand that had thrown it.  I watched it rise and fall.  I watched my fingers close around it.  I noticed everything about the act and motion.  I did this over and over and over, two hundred or more times, and sort of fell into a trance.

Soon, I was able to add a ball and noticed how a second necessarily changed the way I had to interact with the first.  It took real concentration and determination and a certain amount of blind faith that the path I was on would end up taking me where I wanted to go.

To make a long story short, I eventually taught myself how to juggle three and then four balls at once, and then I started using plates and bowling pins and all sort of objects.

Being able to juggle has no real value except that I know I figured out how to do it by myself and that not everyone has this ability.  I like being able to do things that others can’t.  And I like trying things that others won’t. 

During the “Arab Spring,” I lived in Cairo, Egypt.  My family and friends tried to get me to leave the country as it began to fall apart during the uprising against long-time strongman Hosni Mubarak.  Rather than heading to the airport, as most foreigners seemed all too eager to do, I got out on the streets and joined the action.  In the process, I put myself in a few dangerous spots.  I never felt more alive than I did then.  In fact, the very best things I’ve ever done were often the things a more cautious version of me would have shied away from.

But what’s the point of living if all you’re going to do is play it safe?  I’m not asking that question in a purely rhetorical way.  You may not have to put yourself in the middle of a revolution, but you should, at the very least, put yourself in a hard spot every now and then.  This can be as simple as giving yourself a challenge from time to time.  For example, go a week without driving or have a conversation with the next homeless person you happen to see. 

The possibilities are endless.

Of course, attempting to do something out of the ordinary might take you out of your comfort zone, but that’s the point.  Embrace the discomfort.  Try something hard.  Push yourself a little farther than you’ve ever been.  I promise you, in the long run, you won’t be sorry.

Troy Headrick’s personal blog can be found here.

If you’d like to see some of Troy’s art, have a look.

31 thoughts on “You Won’t Be Sorry

  1. Great advice! I’m pushing myself to push the publish button on a new book. What’s the worst thing that can happen? What’s the best? What a great question for me to ask myself! Love your blogs.

    1. I love how you analyze the situation by asking key questions that help you see things objectively. One thing is for certain. It’s impossible to publish a book without approaching a publisher. So, if you want to realize the best possible outcome, you know what you have to do. I’m glad you like my blogs! You made my day. Come back and tell us what happened with your manuscript. Thanks for the comment.

  2. Hahahaha interesting experience and great advice too.
    For me I often only allow myself in such ‘hard’ situations when am really interested in something. It’s as if nothing would deter me.

    Now here iam in India… Far across the Ocean from home and Loving every minute of it, because when I started to dream of traveling beyond my world, I kept trying and looking for ways for that to happen and finally, here we are…😁
    I got a scholarship to further my studies in this diverse cultural hub of a people🤗

    1. Congratulations for having the courage to set out on a grand adventure. Like you, I knew I had to escape my home country if for no other reason than avoid being hopelessly ethnocentric. Living abroad was undoubtedly the best thing I ever did. The world is the best kind of university. How do you like India so far? I’ve been wanting to go there for a long time.

      1. India is beautiful.
        Am now a week in and so far so good. They are hardworking people. Couldn’t help noticing that😁 and they are lovely people too. Welcoming. And they have lotsa dishes! Am enjoying navigating my way around that, more also the chilli in the food🤣
        There’s just so much to experience…

  3. Thank you for sharing this Troy. Wow, how you learned to juggle took some determination/discipline. I totally agree with coming out of your comfort zone. When I started running and after completing my first 10k I set myself a huge challenge and said to myself “I’m going to run a marathon”  I ran that marathon a year later and another one 2 years after that (lots of hard work/sheer determination was involved – coming way out of my comfort zone). I felt such a sense of achievemement and was always buzzing after. Sometimes you just have to “do it” and believe in yourself. Enjoyed this post!

    1. Two marathons! I’m totally impressed. I was on the track and field team when I was in high school. I ran the sprint events and did long jumping too. I never had the stamina for distance stuff. Yes, totally agree. You often just have to take the leap. Otherwise, that little nagging voice of self-doubt can begin to assert itself. I’m always wonder about the so-called “wall” that marathoners hit. Did you experience that? If so, how did you push past it? Thanks for sharing your cool story.

      1. Sprinting and long jumping is tough too Troy. I never hit the “wall” as such, as I kept hydrated and made sure I kept taking those energy gels every hour to avoid the “wall” (it’s all in the preparation), but you do hit stages of self doubt during it (it’s mostly a mental battle). The support from the crowd is phenomenal and certainly keeps you going on the day! Thanks for the lovely comments 😊

      2. Yes, the kind of competitive running I did in high school was very explosive and emotional. But those races started and ended so quickly that there was no time to think. A spirt is just a race where you have to try to find a higher gear to get into, especially if the guys you’re running against are very good. A marathon gives the runner a lot of time to think about quitting. So that little voice we all have inside our heads must be speaking all the time as the miles pile up. You must be pretty tough mentally. I have always been athletic and interested in athletics so it is a pleasure to talk about running–a subject that doesn’t come up every day for me. thanks.

  4. Brilliant, Troy! This reminds me of an interview I once heard with a memory researcher. He said that the brain doesn’t record every event of something familiar we do – like if we drive the same way to work every day, it doesn’t record every turn but just adds a tick to the “drove to work box.” But when we go a new way, it records each part of the journey so we literally create more memories by doing as you suggest.

    Love this post. Thank you for the inspiration!

    1. Thank you, wynneleon. I really appreciate you referencing the study on how we take less note of routine things and routine approaches to doing things. I’ve noticed this a lot in myself. I don’t really recall things that I do regularly and always the same way. (Of course, this could be due to the fact that I’m getting older as well.) So unique experiences build up the library of our memories! That’s so cool and very instructive. Thanks so much for posting such a cool comment.

  5. Safe “If only I had . . .” regrets forfeit to joys of risky “I’m glad I . . .” decisions.

    “To step towards your destiny, you might have to step away from your security.” – Craig Groeschel

    1. Thanks for those great quotes, Fred D. There’s lots of truth there. Here’s another challenge. I come from a family of people who mostly play it safe. So, when I wanted to run off to some far-flung spot to live (often a place they considered “dangerous”), they always thought I was nuts. I often had to defend the life choices I was making. But that always happens to iconoclasts and such.

  6. I enjoyed reading this, but I’m going to be something of a voice of dissent. I will agree that taking the risk is sometimes worth it, perhaps even worth it many times, but I think that as a blanket, general statement “Take the risk! You won’t be sorry” is not very good advice. Some risks are not worth it. My uncle taking the risk to rekindle with his long-lost-love, and blowing up his 30+ year marriage and relationship with his children in the process, only to break up with said long-lost-love less than 2 years later? Arguably not worth it. Spending your life savings to start your dream business with no business plan or partners to help manage and mitigate the risk? Probably not worth it.
    To me, it makes more sense to reframe. I think it is good advice to step out of one’s comfort zone. I think it is good advice to risk feeling discomfort or feeling uncomfortable, as that can lead to growth. Taking risks can be good advice, but I think it’s even better advice to tell people to evaluate, mitigate, and manage risk before taking risks.

    1. Voices of dissent are certainly welcome! I think most people consciously or unconsciously do a kind of cost-benefit analysis as they begin to consider whether or not to engage in risky behavior. For example, playing Russian roulette has almost no benefit and is all cost. I can’t speak about your uncle’s situation because there’s a lot about it I don’t know. There is always the potential that taking a chance can end up causing great regret. (Playing it safe to also lead to regrets.) On the other hand, people can almost always find a way of talking themselves out of doing something that might make them feel uncomfortable. I think your “evaluate, mitigate, and manage” is very much akin to the cost-benefit analysis I mentioned earlier. Thanks for the comment.

  7. I agree with everything that you said. It’s so easy to fall into this monotony. It seems so comforting and familiar that sometimes we forget how to live. It always scares me to see people being at the same jobs for their whole lives, not needing to try new things, not even trying to break their routine. I don’t think I am as brave as you are, as I don’t think I’d ever join an uprising, but I do enjoy putting myself in somewhat challenging situations. If it doesn’t work out, well at least I tried.

    1. Hi. Thanks for the comment. I happened to notice that you have “esl” in your username. You wouldn’t happen to be an ESL teacher, would you? Like you, I’m amazed (and saddened) by those who’ve never gone beyond their little bubbles. I’ve got members of my family who will proudly proclaim that they don’t want to go anywhere and know anything more than what they already know because they’ve seen enough and know enough. For me, I can never see or know enough!

      1. You got me! I’m an ESL teacher in Spain 😊

        You know, once I was told by some “little bubble” people that my life must be sad because I can never seem to be satisfied by being in one place for a long time. Ever since then I try not to judge anyone’s choices. I still don’t fully process that, but as they say different strokes for different folks! I’m like you though, it’s never enough! 😊

  8. Getting out of our comfort zone is the hardest thing to do. I jumped out of mine big time in 2016 and self-published my first book. I will admit it is not perfect, there were a few mistakes in grammar. I purchased Grammarly Pro and kept on writing. 14 books later I am still writing and getting better, but alas, I am not perfect. I don’t care, I love to tell stories on paper, can’t tell them in person well at all.

    1. That sounds wonderful. My advice for you (to borrow a somewhat antiquated phrase) is to “keep on truckin.” Thanks for reading, commenting, and sharing your story.

  9. I love what you write here! Coincidentally, I re-published a post about giving ourselves permission to do what we want to do.

    Sometimes the biggest risk is overcoming our fears! If we approach what we want to do with a well-thought-out plan, and not just jump impulsively at a whim, I believe that many times we’ll succeed!

    Will we succeed each and every time? No, we won’t. However, we’ll have a guaranteed 0% success rate if we NEVER try!

    Let me share the post here with all your readers, because it’s more of a shot-in-the-arm, encouraging kind of post! “Do you need permission to start your dream activity?”

    I hope everyone has a wonderful day!

  10. I’ve known many people who have insisted on taking the safe path in life. I can’t decide if they look happy or sad as they trudge through their days. I can usually spot a person who has veered off that smooth avenue onto a more treacherous route. They’re usually joyous and, sometimes, dismayed by their experiences. They appear to be actually living instead of just existing.

    1. I’ll tell you an interesting story. My father ran into an old friend of mine, a person I used to attend high school with but haven’t seen in decades. This person is very prominent in my little hometown. He makes a lot of money and lives in a mansion, but he hasn’t been anywhere. Anyway, this individual asked my dad how I was doing and he told him about all the adventures I’d had living overseas. Of course, I haven’t made a fraction of the money my old buddy has made, but he told my dad he was so envious of me. I guess he had a boatload of money and notoriety but had played it safe and was feeling as if life had passed him by. Just goes to show you, doesn’t it? Thanks for the comment.

  11. Reblogged this on Surprised By Joy and commented:
    I read this blog on Pointless Overthinking by Troy Headrick a couple weeks ago about putting ourselves in a hard spot from time to time. And I was inspired and curious about how to implement something out of the ordinary in my life. But also stymied because my kids at their tender ages of 2 and 6, really rely on structure and routine to mark their days. Sure, I do new experiences with them all the time like amusement park rides, hiking, and biking with the neighborhood posse to school but within their structure of school, bedtimes and routine.

    As I was pondering how to implement this idea in my life, my daughter had to stay home for two days from school until we got a negative COVID test result. And then there was a teacher in-service day and between the two events, my week of routine got completely upended.

    As I was writing about it that I realized I had, although not intentionally, followed Troy’s advice. Wow, I love reading, writing and the full-circle self-reflection it brings! Because once I saw the connection, I was open to the things I learned about life when you end up in a hard spot – like remembering that I can surf the waves, that I’m wicked fast at triaging what work HAS to be done and that my kids are pretty good at rolling with disruption. Here’s Troy’s post:

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