Is Your Life What You Expected It To Be?

I am a dreamer. I always have been. My mother says that my preschool teacher was certain that I would grow up to be some kind of writer because I was always coming up with stories. I may not work as a full time writer but I still lay claim to the title.

If I had a decent singing voice I might call myself a bard or jester. I wouldn’t want to be a jester for a king. I do a good job of making people laugh, but I hate being told what to do. The first time the king pissed me off I’d stop juggling long enough to fling something heavy at his melon.

I have several evening rituals. On my way to bed I stop to check on my children. In the dark I tell them again how much I love them and then I take a moment to watch them sleep. I don’t think that I sleep that way anymore. You know, that carefree deep sleep of a child.

As I stand there I cannot help but wonder what they are going to be like when they are grown up. What will they look like, what kind of work will they do etc. Mostly I pray that they are happy people of character and integrity.

And then sometimes I think about my own life. It is not that I am unhappy or unfulfilled. On both a superficial and deep level I am pretty close, but there are some gaps. I stop to think about some of the choices I have made. I look at the road not taken and wonder what else could be out there.

What if I had made aliyah. What if I had decided to go to law school or to have become a doctor. There are other thoughts there as well.

Sometimes I wonder about my choices. Sometimes I look at the challenges that I have undertaken and wonder if I have been fair to my kids. Starting new businesses involves a certain amount of risk. Is it fair to involve them? I could have taken a more stable path and perhaps made life better.

OTOH, if the risk pays off the rewards are great. Those could translate into some incredible benefits.


In a little more than two weeks I’ll be 38. Is this who I am. Am I going to be this guy for the rest of my life. He is not a bad guy, but is this it. It is not a midlife crisis. My family is full of people who live into their late 90’s and beyond.

Part of the reason I want to live to be a thousand years old is because there is so much that I want to do. So many skills to learn and master and so little time.

So much to see and so little time. Am I crazy for wanting more.

(Editor’s note: Pictures added on 4/22/16 but the text was left alone.)

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  1. Jack's Shack April 30, 2007 at 5:52 am

    Thanks RF.

  2. rabbi neil fleischmann April 29, 2007 at 9:40 am

    Great post. I think that yearning, striving, seeking, dreaming are of the essence. I’d almost hesitate to use the verb dream in this context because it may be perceived in a somewhat derogatory light.

    Rav Hutner once wrote a student who had written him about his struggles that struggling/seeking more is a good thing.

    Keep on thinking Jack. Keep on thinking and feeling and doing…and writing!

  3. Jack's Shack April 29, 2007 at 4:33 am


    My responsibilities are always foremost in my mind.


    I agree. Without dreams life would be dull.


    I have got good genes. 🙂


    It is important to try and live without regret. Sometimes it so very hard to do so.


    I agree.


    You are right. Once the kids come deep sleep is harder to come by.


    933 SQF- oy vey. That sounds so hard to me.

  4. RaggedyMom April 29, 2007 at 2:12 am

    I think that for the most part, things have turned out overall the way I envisioned.

    I’m generally a planner, not as much a dreamer. I think I do better when things are within my control, like decisions about school and career – than with the unexpecteds.

    RaggedyDad and I check the kids about a half dozen times each every night. I’m waiting for the paranoia to stop, but it doesn’t seem to 🙂 And I’m always listening while sleeping. Though will 933 sq. ft., I guess they’re never that far away!

  5. The Misanthrope April 28, 2007 at 1:53 pm

    I don’t think that I sleep that way anymore. You know, that carefree deep sleep of a child.

    I think that once you have kids you never sleep deeply as you are always listening. I once woke up out of a sleep to hear daughter throwing up in bed when she was still a toddler.

  6. Miss Worldwide April 27, 2007 at 10:22 pm

    I once ended a long relationship because the guy I was with didn’t want to dream. What’s a life without dreams? It’s nothing, it’s just being in a waiting room. Dreaming is great, and combining it with doing is even better.

  7. Z April 27, 2007 at 10:14 pm

    No, but I do think you have to live your life without looking back or second guessing yourself. It’s very important to me not to sit here and wish I had more or did this or that. Regret is not a word I understand the definition of as it applies to the landscape of my life. I can’t live like that.

  8. The Babka Nosher April 27, 2007 at 5:34 pm

    If you’re really going to make it to 1000, you better invest in some good face cream.

  9. Shoshana April 27, 2007 at 2:17 pm

    I’m totally a dreamer also. I think it would be sad to look at one’s life and say, “Yep, I’m done, there’s nothing more to hope for.” I think it’s the dreaming that keeps us living, really living.

  10. Rhea April 27, 2007 at 12:32 pm

    I have these same thoughts. I would be the last person to say you should stop yearning for things. As long as it does not endanger the people who depend on you, why not?

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