Random Thoughts from a Restless Mind

Dr. Darrell White's Personal Blog

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Second Chance? Sunday musings..5/31/2026

1) Ambush. A group of adult tigers.

We all needed to know that.

2) Podcast. Funny phenomenon, podcasts. Some are a great way to learn about a new hobby. For instance, Beth and I will listen to 3 new ones on birding I discovered in today’s Sunday paper as we drive to our southern outpost next month. Others expand on stuff or people you already know; my friend Uday has a very cool weekly podcast that lives in my day job’s space.

Then there are the ones that are just fun. Smartless, Strikeforce 5 and others that are basically like being a fly on the wall at a good hang. Come to think of it, isn’t that what Amy Poehler calls her podcast? Ones like “And the Rest is History” are a little bit of both. For whatever reason I find podcasts much easier to digest than books on tape.

Got any favorite Podcasts to share?

3) Old. Inimitable essayist Roger Rosenblatt has written a book, I believe, called “Rules for Aging”. Seems he also has a sequel, “More Rules for Aging”. I stumbled across an excerpt from the latter in the paper this morning (the Sunday papers appear to be fertile ground for musings) entitled “How to Stay Old”. As opposed to stopping being old, which bodes for a rather dismal future.

There are 11 rules, all of which I found interesting, some more compelling than others. I think I’ll muse on one or two each week until I make it through the list.

The first rule is “Run when you hear ‘We must do this again.'” Nail, meet head. This is precisely the equivalent of “let’s get together sometime”, or “we should play some time” after crossing paths with someone you may have once played golf with. Whoever says any of these doesn’t mean it. Admit it, if you simply agree, you don’t mean it, either. Believing otherwise chips away at whatever reservoir of happiness you are harboring. It ain’t gonna happen.

If you do truly want to convene, over a glass of wine, on the first tee, or wherever, pull our your phone and toss out a couple of dates. For sure not a one of those present will have enough information to pull the trigger, but the older I get the easier it is to just say ‘yes’ to a date and then work it out later.

Don’t run from “Let’s do this again Friday after next.” Meet sincerity with sincerity and plan like you mean it.

4) Founder Mode. This is how the CEO of Airbnb Brian Chesky describes his management model even though his company is almost 20 years old and now has some 8,200 employees. How he defines Founder Mode and how he implements it is very interesting. My first inclination was that this was a form of micromanagement. A fancy term that simply meant an inability to delegate authority and responsibility to capable people further down the org chart. Even for famous control freaks like Steve Jobs a company eventually becomes too big to micromanage.

Which is what makes Chesky’s expanded definition interesting, and actually makes it applicable to our tiny 25 person shop. His thesis is that the CEO needs to be at least conversational with the operating details of the company. “As a leader, you’re in the details,” in the weeds as one of my co-founders used to say. There are times when a business needs to evolve, occasionally times when something revolutionary is occurring, and the only way to effectively lead is to be “into the details” enough so that a lack of understanding is not a reason to make a wrong, or less right move.

There has always seemed to me a concrete difference between the job of the CEO (30,000 and 3,000 foot views and “big picture” decision making) and that of the COO or GM (300 and 30 foot view directing implementation). I don’t think the CEO of a company with $12BB in sales and 8,200 employees can actually know any more than a fraction of the details, Founder Mode or not. Frankly, I’m pretty sure Chesky doesn’t, either.

But what DOES make sense to me is that in the face of a major decision or inflection point for a company, the lead dog really does need to know the details if for no other reason than doing so saves everyone downstream from the need to bring him or her up to speed. In my world that presently means a deeper, more granular understanding of how we manage information.

In order to ask the right questions and then come to the right conclusion, after more than 20 years I, too, must return to Founder Mode.

5) Second Chance. “The Midnight Library” is a novel by Matt Haig in which the main character visits the eponymous library. Considering suicide, in the library she finds books that tell how her life would have been different had she chosen alternate paths along the way. In the just released sequel “The Midnight Train” the 81 year old hero is grief-stricken by the missed opportunities over his lifetime. He boards the train and is transported to pivotal moments in his past, allowing him to reflect on his options with the wisdom of his years.

Both are a romanticized take on my beloved multiverse; both, in the author’s take, are ruminations on a second chance.

Now, to be fair, I’ve not read either of the books, but from what I have gathered from the interview and from other reviews I’ve read, both offer a kind of second chance. The author survived an attempted suicide in his 20’s; he views the 25 or so years he has lived since then as a second chance. I’m going with the assumption that the heroine in “Library” chooses life, and for the sake of this bit of musing I’m going to assume that the hero in “Train” gets a mulligan, getting off the mystical train as a younger version of himself bestowed with the perspective of the 81 year old who boarded the train.

Of the three, the heroine in the library, the older man at the train station, and the author, the only one who truly received a second chance was the man on the train. Riddled with regret he chooses to re-boot at some very specific intersection, convinced that he will do his life “the right way.” Again I have not yet read the books and so I don’t know if the story does, indeed, have him disembarking in the past. But neither the author nor the heroine in the library really got a second chance.

For what I hope are wonderful reasons they continued on from that terrifying decision point to live with and for those in their present.

This is all fiction, of course. A thought experiment, if you will, one that I have proposed and parsed here before. “The Midnight Train” directly addresses the concept of regret. The hero travels through his life and feels a deep regret about decisions he made, and why he made them, and concludes that he is willing to trade all that occurred after each one for a second chance. He is willing to forego everything he did and everyone he met the first time around. Does the heroine in the library get to choose to start again on one of the alternate paths she sees in the books? Again, I didn’t read the book yet, but I’d bet like George in “It’s a Wonderful Life” that she learns how much she means to those around her, and how much better her life is than she realizes.

And like the author, how glad she is that she is still living her first chance.

Perhaps there really is a multiverse, and in the infinite iterations of the universe there are versions of our lives that are in some way better. Or we live an infinite number of lives through some kind of reincarnation, either in the traditional sense or by traveling between different slices of the multiverse a la “Dark Matter”. Perhaps there is an afterlife, a joyful place we go after our earthly journey is concluded. I surely don’t know. What I do know is that regret, wishing that you’d zigged that one time instead of zagging, means that you are willing to change everything and everyone from that precise moment on. Everything and everyone.

Is a second chance truly worth that?

I’ll see you next week…

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