Newsletter

The Golden Albatross

Don’t look up golden albatross on Urban Dictionary. WTF? I told you not to do that. Let’s focus on the more traditional meaning. According to Wikipedia, “the word albatross is sometimes used metaphorically to mean a psychological burden that feels like a curse. It is an allusion to Samuel Taylor Coleridge’s poem The Rime of

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Ryan’s Tim’s Vermeer by Ryan Wooley

It has become a running joke in the house that “Dad” is obsessed with educational shows. I won’t deny it; I like documentaries. Almost every Sunday morning, my family discovers me watching some form of non-fiction as I make vegan, gluten-free pancakes for them.  I recently watched a documentary that was so moving to me,

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Resignation Nation

You might think that the Great Resignation of 2021 doesn’t apply to you. And in a way, it probably doesn’t. Folks who have been traditionally shat upon now realize that it just isn’t worth it. After what’s happened over the past year and a half, who really is going to tolerate working the fast food

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Caricatures by Ryan Wooley

I have a good relationship with my boss. We’ve worked together now for 13+ years. I respect the work he has done to make our school better and to improve education in general. I think he appreciates the work I have done to contribute along the way. As one of the most senior members of

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You’re anti, you’re anti-social…media.

Bonus points if you caught the Anthrax reference. The band, not the disease. I hope you never catch Anthrax. Look, it’s pretty easy to find evidence online demonizing social media. It’s the same criticism that was lobbed at books (Socrates was kind of a dick about books), movies, radio, television, and video games. I’m not

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Responsibility Magnets by Ryan Wooley

10:52 PM. Friday July 9, 2021. Today is a “day off”—my second in months. I get to sleep in until 7:45 AM. I get up and ready myself for my son’s double-header baseball games, which start at 10 AM. We are supposed to arrive at 9, but we are 15 minutes late due to me

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The Declaration of [Financial] Independence

Happy 4th of July! Because my newsletter rotation landed on Independence Day, I wanted to take the opportunity to do something a bit different. My “curated” newsletter format will return on July 18. Today, I wanted to share with you “The Declaration of [Financial] Independence,” something I wrote for another project that didn’t quite play

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No One Cares by Ryan Wooley

My good friend Tim has published dozens of books. As a wanna-be writer, I watched with great anticipation as he built his author business from the ground up—first as a side hustle when we were colleagues. This vantage point has given me a vested interest in seeing where the story goes. Even if I didn’t

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Okay, Boomer…GenX is listening.

Dr. Rick Steiner didn’t write the book for us. But trust me, we need to be paying attention to how Boomers are living in retirement. Retirement: Different by Design: Six Building Blocks Fundamentally Changing How Life After Work is Viewed, Planned For, and Lived takes an in-depth look at the bridge between what we’re doing

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Time’s Winged Chariot by Ryan Wooley

I have always felt like time is my enemy, a feeling that no doubt has a few different origins. First and foremost, I have a LOT of interests. There is so much in this world I would love to spend time doing. Even if I didn’t have work or other obligations, there is no way

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It’s Time to Rethink Retirement

Although not exactly what you’d call an “in-depth” article on the front page of Yahoo! Finance on May 17, 2021, the short post is important. Let me save you the click. Jo Ann Jenkins, the CEO of AARP, said that “For the first time in recorded history, the number of people aged 65 and older

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Five Essential Principles for Designing Successful Collaborations by Ryan Wooley

I revere my favorite musicians, and have followed some of them into that stage of life and career when they get grouped into “all-stars” lineups at award shows where the rock gods crowd onto the stage and wink and nod while trying not to bump into one another as they play rhythm guitar chords. Let’s

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Retiring? Your Next Chapter Is About Much More Than Money

Is retiring even the right word? At Teaching Transformations, we’re not really sure. The idea of binging Netflix or sitting on a beach for 30 years doesn’t sound all that appealing. I was usually good for about two weeks of summer vacation before I started reorganizing my sock drawer. In this new book by Ted

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Feel Like a Number by Ryan Wooley

I feel like just another, spoke in a great big wheelLike a tiny blade of grass in a great big field… – Bob Seger, 1978 I am not famous yet, unless it was in a past life. And, as possible as that feels, it has no bearing this time around. When I was an English

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It’s Time to Start Living an Effortless Life

Our grandparents grew up during the Great Depression. Our parents brought forth that perception of scarcity. And rightly so, because it was what they were taught. But now we’ve grown up, and the world has changed. We no longer need to believe that life is difficult. From a historian’s perspective, we’ve never had it so

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Donning Gen X by Ryan Wooley

I have always been on high alert for self-fulfilling prophecies. My position is that as soon as someone accepts any kind of label, they immediately start living up to it. You mark me as the “crazy neighbor,” and I start feeding that image. Some morning, you come out to go to work and find your

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How Will You Remember the Pandemic?

“The stories you hold on to will be colored by your own experience—but also by the experiences of those around you.” In a recent article by Melissa Fay Green for The Atlantic, she explains the pandemic hasn’t been a single traumatic event like the tragic Challenger explosion or the events of 9/11. We’re in a

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Skill Stacks: Why National Treasure May Hold the Key to Everything by Ryan Wooley

This is for you, Steve Hopkins (friend and former colleague, not signer of the Declaration) Do you remember this 2004 Disney movie? I want you to picture the “glasses scene” inside Independence Hall. Benjamin Franklin Gates (played by Nick Cage) discovers a pair of special glasses that he and his compadres use to decipher secret

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The Ideal Age to Start a Business

Surprise, surprise. A startup by a founder in their 50s is twice as likely to be successful as one founded by an entrepreneur in their 30s or 40s. This brief article on Inc.com by Jeff Haden talks about why most people are wrong when they think the most successful entrepreneurs were twentysomethings (Bill Gates, Mark

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Pivotal Moments by Ryan Wooley

Life’s pivotal moments are often exaggerated when we tell our stories. “She turned around, and I just knew that she was the one.” “I decided then and there that I was done with that fuckin’ place.” “I saw that performance and I knew what I wanted to do for the rest of my life.” I’m

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Seize the Day – Introducing Transformations

“I don’t deserve to feel like this. I have a career, a loving spouse, a wonderful family—and yet, I feel down, unfulfilled, sometimes hopeless. Maybe I just have first world problems.” It’s not you. As it turns out, there’s a scientific explanation for the oblique sense of dissatisfaction that you experience in your forties or

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