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I know that Yom Kippur isn't exactly known as one of the "fun" Jewish holidays, but every year I can't help but laugh at what's easily my number one Yom Kippur memory.


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That is what makes memories … memorable. And, finding something to laugh at on Yom Kippur, the Day of Atonement, which is probably the most important and solemn Jewish holiday, would be memorable.


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I can't believe you're not even curious what it is!?


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You know I love to "connect the dots", and all you had to say was Yom Kippur, fun, and memory. Obviously, it was when Rabbi Scott asked us to speak before his congregation on Yom Kippur.


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Well, I still find it surreal that we were asked to speak about money on one of the High Holy Days. And that we titled our presentation, "Oy Vey, You Want To Talk About Money?"


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The day is about reflection, making fundamental changes – or at least adjustments – and trying to become a better person. And, just because it is a spiritual journey, there is no reason you cannot make learning fun.


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True. I remember the time Rabbi Scott put a piece of aluminum foil in the children's Yom Kippur service program to help them understand that Yom Kippur's a day for reflection. But even you must admit that making a congregation laugh about money on a religious holiday is a bit much.


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But, memorable. A few years later, I met someone that attended that service, and he said he's never forgotten it.


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For the content or all the food analogies?! I can remember we started by saying how we just wanted to give everyone some food-for-thought and then saying, "Oops, since Yom Kippur's a day of fasting, maybe bringing up the subject of food wasn't such a good idea."


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Of course, it did not stop us from doing it, again and again.


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How else could we explain our unexpected journey into personal finance without mentioning it started at our first speaking engagement … which was at a Jewish Federation breakfast?


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Or, how our detour into criminal justice started with me meeting with the chaplain at a men's prison? But I knew it was meant to be when she told me they had the only kosher kitchen in the Texas prison system.


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And each time we looked at each other and then the audience, and we all laughed! With each mention of food, it just got funnier and funnier. But there was no way to avoid it.


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I know. How could you tell the story about realizing all the money you were mindlessly spending at Jamba Juice without mentioning your almost-daily smoothies? Or, how you went grocery shopping at Whole Foods because it was convenient but not cost-effective. Anyway, until that day, I never realized how so many of our stories have to do with food.


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I think the highlight was toward the end when I was explaining how I felt overwhelmed trying to tackle personal finance. That at times, things seemed insurmountable, and then you told me … it's like eating an elephant, you can do it, just one bite at a time. And everyone started laughing again.


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On any other day, I doubt that analogy would make you think of food. But, on Yom Kippur, and especially since we were presenting after at least 15 hours of fasting, everything makes you hungry


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I guess it's like being so tired that you get slap happy. But I never thought a day of atonement and reflection could end up becoming a day of laughter.


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On Yom Kippur, we wish people an "easy fast" or a "meaningful fast" … and if a bit of laughter, even if not intended, helps, what is wrong with that?


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Good point. For that matter, you don't need to be Jewish to take a day, or even just an hour, to stop, to think, and to improve.


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No fasting required.


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The last few days have been beautiful fall weather, and I can't help but wonder – do you ever miss having your Ferrari convertible?


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Although some days are perfect convertible weather, given I barely drove it the last few years I owned it, averaging less than 50 miles a year, I can honestly say, "No." In fact, I cannot even remember the last time I drove it.


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I can't help you with that, but I'll never forget the last day we taught at KIPP Houston High School, and you drove it there. You should've seen the student's faces as you were lowering the top on it.
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Thanks for sending me Natasha's Austin-inspired business plan. But while I know that's her future, I can't help but think about the first time I took her to Austin.


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All I remember is that it was love at first sight.


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It was on our way home from taking Sawyer to camp, and I told her we were making a slight "detour". She was so excited when I pulled up to the hotel as she's always loved hotels. But that night, as we walked onto Congress Avenue Bridge and saw the thousands and thousands of bats fly out into the sunset, she was mesmerized and "in love".
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I'm still smiling at you letting Sawyer drive your Mercedes G-wagen. Although I know that her dream car's a Ford F-150, I think yours is her "fantasy car".


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I knew the "long way" to drive back to your house, but after asking her if she knew the best way, it seemed easier to have her drive.


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Well, you might have thought of it as efficient, but she thought it was exciting. And she told me that she was honored you trusted her to drive.


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Did she mention that once we got back to your neighborhood, we saw a huge turtle on the road? Moving very slowly, of course, so I was not concerned it would become an unexpected road obstacle.
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