41 Comments
Apr 20Liked by James Bailey

I love how this turned out James. Such a satisfying blend of storytelling and hard data, this is a piece I’ll return to again and again as I navigate my financial journey.

And so good to see you publishing and putting your ideas out there. The world is a better place because of it (:

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Tommy, thank you again for contributing and pushing me in areas to make it better. I’m going to take in your piece on impermanence next, and I look forward to connecting on Monday.

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Such a treat to have a James Bailey piece in my inbox.

My husband is a long-term investor, holding companies for years. I imagine you two might have a similar approach to this whole investing thing. Thanks for breaking it down for us in such a visual way.

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Aw, Charlie, I appreciate the note - and I'm committed to trying to occupy your inbox more frequently than once a quarter. I'm glad you enjoyed and appreciated the story, and that your inbox is a destination for me. :)

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Once a quarter, once a week, once a year... I'll look forward to it regardless!

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Gripping as I felt Morgan Housel being put on notice watching you weave narrative with the nominal finding the emotional threads and presenting them perfectly my friend. Well done.

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I feel like if I reply to your compliment, I will jinx the good fortune of being mentioned in the same sentence as Morgan Housel. I appreciate it, Steven. A well done from you means the world.

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I've never thought of the investing journey to be similar to a momentous mountain climb. Great insight and storytelling here, James! I'm fairly young and still new to the whole investing thing, but I'm glad I read your piece at my current age. It's one to remember for a long time.

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Linart, people who are your age and put their savings into diversified funds, and don't touch it for four decades become fabulously wealthy AND they have more meaningful lives because they're not worrying about money along the way :) I apprecaite your reply.

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It's truly a gift to be able to know this at my age. Always admire the wisdom you share in your pieces, James.

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Hey James, I really enjoyed this essay. It left me both entertained and a little bit more informed :) One thought I picked out is that it is like a partnership, as in, not only wanting to be there for the gains.

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Henri, you're so wise....there's so much truth to what you say. Investors need to love their portfolio on the way down, on the way up, as well as the rest of the time.

It's so great seeing your name in my inbox :) I trust you are doing well.

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Apr 21Liked by James Bailey

My palms were sweating as I read the first half of this post. Such fantastic writing, James. I was not expecting the turn this post took halfway through: you absolutely nailed the simple + surprising essence of a Shiny Dime. Having just finished The Psychology of Money, this post is very timely for me. The metaphor of climbing mountains for navigating the ups and downs of the stock market is apt. Having faith and avoiding panic when things are bad. Not getting greedy when things are going well.

Having 95% of my wealth in the market, I will return to this post to calm my nerves and stay the course when the next dip comes along.

Thanks for writing these beautiful, thoughtful, and insightful posts, James. Your writing is an act of service to your clients, your kids, and everyone who is lucky enough to read your writing.

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Hi (again) Jack, this is the last message for this morning. I appreciate your reply and am so glad that the first half of the essay had you on edge. I would have liked to make it shorter, but in the end, I decided to keep it a bit long and cite some of the data (that some readers might have skimmed through). And if you think I nailed the Shiny Dime, well, then I'll quit wondering if I could have improved it in some way.

OK, have a GREAT rest of your weekend.

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Apr 21·edited Apr 21Liked by James Bailey

This is a very engaging read. I loved the paralell between climbing and investing.

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Dhanesh - thank you for taking the time to respond. I just read your essay and loved it. Bravo!

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James, this is a superb piece.

I was taken into the current of your storytelling flow from the first sentence to the last.

Thank you for the reminder to be patient and play the long game. Thank you for the story.

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Anthony thank you for taking the time to share how the essay landed on you. I worked on that beginning for quite some time to try and have it be short and draw readers in so I’m glad you noticed and felt that way. When I was doing some research a while back on Tenzing, and I came across the information on his name, I couldn’t believe it and I knew immediately I had my ending. 😁.

It’s funny you and me and writing. You publish these excellent, thought-provoking, and insightful pieces each week, and I publish my hopefully inspiring and thought-provoking long form pieces once a quarter. Both a different and effective way of approaching our subjects.

I’m grateful for you.

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I will absolutely be sharing this essay with family, James. I was a coder at Morgan Stanley in 1989, and we kept re-running a script querying the "latest index price", charting the market's free fall. You offer so many truths here. But fear that this time the market will bottom out stays humanly consistent.

I love the visual of the rope and Hilary being supported by Norgay. What beautiful imagery. Filled with facts and detail that I will return to enjoy again. Thank you.

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Karena - throughout the 80's in high school and college I worked at brokerage firms and experienced the bewildered brokers standing around in shock on the Black Monday crash. I'm pleased you liked the piece. One thing that I'm discovering is that it's harder for me to write and publish pieces that require research and have lots of data. I think I'm going to stick closer to my insides - my heart and my observations - and try and publish more frequently. :)

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Breathtaking writing. 😉

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JT, thank you - that means a lot to me and I sure appreciate it. :)

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Apr 20Liked by James Bailey

Beautifully written piece James

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Thank you, John. And thanks for taking the time to tell me. This one, like the last one, took a while to weave the story together. I only wish I could have made it shorter. :)

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Apr 20Liked by James Bailey

Excellent, James! I still remember one of our first conversations about staying the course, and try my best to follow your advice. Thank you!

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Loys, GREAT to hear from you. If you've done a pretty good job of staying the course, I honor you. It's hard and no investing experience is every perfect! I hope you are doing well.

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Hi James, always fun to read your substacks! I am well, and I hope the same for you and your family?

We did stay the course, which allowed us to build our aging-in-place home, husband’s retirement, and me take a job that emphasizes fulfillment over money for this final stage of my career. Your advice worked and I appreciate you sharing it!😊

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Apr 20Liked by James Bailey

A wonderfully eloquent way of saying “stay the course!” —not that I’ve personally ever needed to hear that message (wink).

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Joe, I love you pal. You can bring some chocolates and biscuits to our next meeting :)

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May 4Liked by James Bailey

Wow! I love how you blend storytelling with financial wisdom…and present it as a relationship. Amazing, truly 👏

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Thank you Maria - I appreciate it. Getting this piece across the finish line was a battle because weaving the elements together was way harder than I imagined. I wished I could have made it shorter, but in the end that would have taken even longer!

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It works! We can revise our work forever, but at a certain point we must be done in order to move forward.

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James, what a fantastic piece. I learned so much about both Hillary and Norgay's climb—I hadn't even heard of Norgay. I love how you made these parallels to the market, with so many lessons I need to hear. This really resonated with me: "We delude ourselves by believing we’ll rope back in when the coast looks clear." I know that one all too well!

Really glad to see you publishing, as this is both great storytelling and crucial wisdom—my favorite kind of reading. Thanks for the great read. I'll look forward to more!

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Rob, Thanks for reading and responding with what resonated with you. And I appreciate the compliment on storytelling and wisdom. That's my aim - only this time the essay was longer than I would have liked but I needed to publish and move on rather than figure out how to make it shorter.

I've got your Trying to Relate piece queued (UK word :)) up for this weekend.

Back at you soon.

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Apr 20Liked by James Bailey

Your use of story and metaphor to educate about your area of expertise is beautifully navigated James. Your essay also makes it clear how much misunderstanding I have about investing, the fears that operate in the background of my thinking, and the risks I am posing to myself by my way of climbing. I think I need a conversation with you.

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Rick, Thank you. We need a conversation anyway - just because they are so contributing and nourishing to me. Regarding the fears that operate in the background, you're human and that means that we live with those fears and try to honor them, but not act on them. I will reach out and schedule a conversation. I look forward to it.

And thanks for making it through the entire piece. I'm committed to shortening things up as I move forward!

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Apr 20Liked by James Bailey

The piece wasn't too long.

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OK, I will let you be right. It is the length that it is, which makes it just as it should be. My pieces tend to be ~1,500 words and Sara Fay once told me that Substack pieces should be around 1,200. I probably have a story in my head about that now. I'll let go of it now thanks to you. :)

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