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Friday Freedom Question: Risks taken, risks not taken

I was thinking this morning about risks — about the chances we take … or don’t take. Not so much risks like whether to shoot for that Xtreme skateboard move or play it safe. But the big, potentially life-changing risks.

Oh, sure, the skateboard move or the jump out of the plane or whatever can also be life-changing. It could squish your ribcage or your pelvis, not to mention your brain. Or it could tell you you have more courage than you knew, courage you could use for good in the rest of your life. But I’m thinking more of the risks where you realize at the time, “If I do this thing, my life will be on a different path.”

So today’s Friday Freedom Question asks What was the biggest risk that you didn’t take (but wish you had) and what was the biggest risk you did take that altered your life?

For me, the biggest risk I didn’t take (and now regret) was that I didn’t drop out of high school and leave home at the earliest opportunity. Sure, it could have ended up as a dead end or with the humiliation of crawling home to “I told you sos.” But looking back, I think it would have shown me I was actually a more courageous and visionary person. It might — who knows? — have led me to opportunities I’d have been confident enough to explore, once I knew I could survive beyond family and prison school.

It’s harder to pin down the biggest risk I did take because the things outside observers told me seemed risky to them never seemed risky to me: leaving a place I was secure and moving across the country to a place where I knew nobody and had no connections — because that place called to me; or quitting corporate communications to be a freedom writer. These seemed less like risky choices than inevitabilities to me (at least once I’d reached the decision-making moment). So it’s hard to say.

But what about you? What was the big risk you turned away from and now regret? What was the big risk you took and what were its results?


  1. MamaLiberty
    MamaLiberty June 10, 2016 11:04 am

    I can’t really think of any serious risks I’ve taken and now regret, though there are a few decisions I’ve made that I regret, of course. At the time, they didn’t seem to be any more risky than other options.

    I have taken a good number of actual risks… decisions that could have been a disaster, but which turned out well.

    The greatest of those was to retire early, sell my property in Calif. and move to Wyoming. I had no clear idea then how I would earn enough to live, and only a scattering of friends here. I left my entire family and a great many friends in Calif.

    The bottom line, after a lot of thought and anxiety, was that the cost of living there – added to the poisonous political situation – would make it impossible for me to live on my small pension after I got too old to work. Not being willing to live on charity, either family or government, I had to go somewhere. It’s not perfect here, naturally, but it’s closer to it than I ever expected. I don’t think I’ll ever regret it.

  2. Frank
    Frank June 10, 2016 11:31 am

    Whether er not it makes a difference, I myself don’t think in those terms of “greatest risks ‘er ‘risks not taken. So many risks arise midstream, nest pas? Iff’n one had the rushers ta back out it too often is no longer possible, ‘er is this passive risk taking, anybody’s guess?

    Whilst I is here under duress, I ain’t in pain. I’ve been driven to observe naked pagans at the dance an I’ve lived to write ’bout it.

  3. LarryA
    LarryA June 10, 2016 12:30 pm

    Biggest risk I did take is easy; asking my wife to marry me. Best decision I ever made, going on 48 years. I’m not sure saying yes was the best decision she ever made, though.

    Not many of the risks I turned down really stick out. I suppose one of them was choosing the wrong course of study for my master’s degree.

    Of course, since we can’t look into the alternate reality that would have resulted from a different decision, we can’t really know if it would have actually been better or worse. (A common theme in Sci Fi.)

    For instance:
    We escaped from California too, ML. We were living in Barstow when Dad retired from the Army, and had a lot of friends there and offer of a pretty good job. But the schools already sucked. (1960) My parents could see that that wasn’t going to end well.

    The great “success” after that was, of course, the tech boom in Silicon Valley. However, I wonder if California might have been better off without. The enormous economic boost certainly enabled their politicians to dig their fiscal hole much deeper, which might in the long term cause more disruption by postponing the inevitable.

  4. Pat
    Pat June 10, 2016 1:17 pm

    The biggest risk I didn’t take was follow-up after buying my forested 2-acre property in NE Washington State. Surrounded by other private property, with stream (and deer run) running through it, it was a perfect opportunity to get away from it all, and become proficient in survival skills. But I took time to think myself out of it, continued working as a nurse, and realized other things I wanted to accomplish. Don’t know what I would have become – but I’m sure I wouldn’t be online today.

    The biggest risk I did take was deciding to have and raise my son – alone. It was hard, but it was worth it… on many levels.

  5. RustyGunner
    RustyGunner June 10, 2016 2:45 pm

    I make a point of never regretting. I have the odd wistful thought about the road not taken, but see here: I am married to a better woman than I deserve, with children I love dearly and would not trade for the world. Everything I have done in life, every triumph and tragedy, every bonehead stunt, every shortsighted, stupid, silly and self-defeating Fumducker decision I have made in life has led me to the place I am in now. Any difference in my path and I’d have missed these wonderful years with these wonderful people, and that would be something to regret. I look forward, not back. The past serves as a source of cautionary tales and great party stories.

    As to risks taken, parting company with family and known environment to begin my life anew on the east coast was a big leap in the dark. I’m about to do it again, too. We’re moving west soon, as close to family in southern CA as possible without actually entering CA (Kamala Harris would wake up screaming the moment my moving truck crossed the state line). We know nobody out in the desert, I’m the only one who has ever experienced that environment. It’s going to be exciting for everyone, hopefully in a positive sense.

  6. Pat
    Pat June 10, 2016 3:34 pm

    Well, it’s been alluded to here, but I’m not sure that taking a risk or not taking one necessarily involves regretting the action. We may see enough pro and con to sidestep the risk part, or we may see another road to take that seems a better fit. Or other circumstances may crop up that become more important to our lives than the original idea which involved a risk. Our lives are not set (Thank God!), and we have choices – and sometimes those choices are led by our gut, and sometimes by our mind. If we understand our choices, we don’t necessarily have to regret them, even as we wonder what might have happened if we took that other road.

  7. LBS
    LBS June 10, 2016 5:37 pm

    I regret not having that third child, despite severe morning sickness and the necessity of a C-section. However, my greatest regret is not homeschooling my children from kindergarten through high school. That decision to leave the kids in public school has caused a lot of grief. (I did homeschool my youngest for three years, in high school. I never regretted that decision!) We can never know exactly what would have happened if we’d made other decisions, but I’m pretty sure the world would have been a happier place if I had homeschooled my *three* children.

  8. MamaLiberty
    MamaLiberty June 11, 2016 5:54 am

    LBS, I hear you! Homeschooling wasn’t even something we thought of at all 45 years ago when my sons were small. We did a lot of “homeschooling” stuff throughout their lives until they went out on their own, but the battle against the government “school” indoctrination was always with us. We did look at a few private schools in the area, but their indoctrination varied only a little, and the cost was beyond our means no matter how frugal we were.

    So, even though it wasn’t really a risk we chose to take, I’ll always regret that we didn’t homeschool… We didn’t know about it as an alternative to gov. school, and I suspect we would not have been allowed to do it then in any case.

    I do have to say that my sons turned out well anyway. Self governors, independent as hogs on ice, and good providers for their families. Why in the world they both choose to remain in California is simply beyond my understanding.

  9. Mark Call
    Mark Call June 11, 2016 6:48 am

    As a good, and at one time very agnostic, libertarian – they’re very much related:

    I took a risk reading for myself, and then believing, a Book that I’d been led to believe might have ‘some value’, but certainly was NOT the “Word of God.” That in turn required to believe YHVH, rather than men, and take the risk of listening to Him, in things I never once would have.

    The biggest regret, and risk not taken, was the years I wasted thinking I could do a better job on this life without that.

  10. capn
    capn June 11, 2016 4:15 pm

    Risk taken that I would undo? I would not have committed the actions that resulted in my having to survive in a federal institution for a year. Those actions still influence my life to this date. Dumb, rebellious kid stuff.

    Road/risk not taken? This one still hurts 38 years down the road. sigh
    I had established an intense (for me at least) relationship with a woman whose Father moved her (she was 18 at the time and I was 21) and his entire family to another state. A year later she called to talk and (alas unspoken) wanted me to come to her to save our relationship. I didn’t go for lots of silly reasons and have regretted that decision since. 38 years. I sincerely do hope she is having a good and happy life for she surely deserved it.
    (And no this is not afishing story.)

  11. capn
    capn June 11, 2016 4:17 pm

    that should read a fishing story
    Proofread capn proofread

  12. daylan
    daylan June 11, 2016 6:45 pm

    Biggest risk I didn’t take was leaving the cult as a teenager into which I was born (until much much later in life, which was also the biggest risk I did take – 50 years later).

  13. jolly
    jolly June 12, 2016 6:49 am

    I guess I’m a natural risk-taker. So far, most haven’t been long-term disasters, but nothing particularly lucrative, either. I’m doing another of my “projects” as my kids call them – but this time for fun, not necessarily for profit.

  14. Ron Johnson
    Ron Johnson June 12, 2016 10:15 am

    I have lots of little ‘shudder’ moments. Those are times when something triggers a memory of a close call, or an embarrassment, or a regret. The feeling generally doesn’t last long, but it leaves me with a sense of humility. It says I made mistakes….lots of them….that could have or did turn out badly. Like the lawnmower accident (I’ll spare you the details, but for twenty years I would visibly shake for a few seconds when that memory would get triggered).

    I’m not so sure I live with regrets. Maybe momentarily when I think about the one that got away. Or the career I didn’t pursue. But then I think about what I’ve got and I quit my pity party.

    My guiding imagery is from “The Road Not Taken,” which is often interpreted as an ode to risk taking and rewards. However, I think it’s about the permanency of decision making, the impossibly of turning back time and exploring another pathway and outcome. It says to me: be satisfied that you lived, committed, and arrived. Regrets are inappropriate.

  15. Eric Oppen
    Eric Oppen June 12, 2016 10:47 am

    In my own case, I’d say the biggest risk I regret not taking was staying on in Taiwan after my college Term in China. I came home to find that the situation at home had gone badly pear-shaped and by the time I was able to get things back on something resembling an even keel, I was trapped and have never been able to free myself. (Getting out would involve knowing somewhere to go, and having money—galavanting costs money, as I have pointed out to various well-meaning people who were trying to give me advice over the years.) In my own defense, I didn’t have any money to support myself in Taiwan while I looked for work teaching English, I was docile and used to following orders, and I had no idea how bad things had become in my absence.

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