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MC#034: Leadership in Turbulent Times

Also: Resilience: Actual vs Perceived + Annual Review

Jason Shen
Jason Shen
5 min read
MC#034: Leadership in Turbulent Times

Hey friends,

Happy New Year! This is the 34th edition of Making Connections, where we take a random (illustrated) walk down tech, fitness, product thinking, org design, nerd culture, persuasion, and behavior change.

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🖼 Visual: Resilience: Actual vs Perceived

You ever notice how the people who brag the most about being tough or a badass never end up being so? How bizarre.


🧠 Thought: Lessons from Abe, Teddy, and Franklin

In the last few days, we’ve seen the culmination of a disastrous presidential term play out. The violent riots that trashed the Capitol and led to five deaths so far were shocking and despicable. My only hope is that it serves as a wake up call for everyone who’s felt they had to play along with Trump’s BS for the last four years.

But rather than unpack that event in detail, given there are many others who can do that better than I, let me turn to history. In the book Leadership: In Turbulent Times, historian Doris Kearns Goodwin, who penned the famous book on Lincoln that inspired Obama, explores how four President’s, Abraham Lincoln, Theodore Roosevelt, Lyndon Johnson and Franklin Roosevelt each led the country through a difficult and trying period. I share quotes from this book as a way to remind ourselves of what great leadership can look like.

“It is not in the still calm of life, or the repose of a pacific station, that great characters are formed,” Abigail Adams wrote to her son John Quincy Adams in the midst of the American Revolution, suggesting that “the habits of a vigorous mind are formed in contending with difficulties. Great necessities call out great virtues.”

A throwback to the “talent needs trauma” thought from MC#003. We’re living through a difficult time but it affords us the chance to build greater strength and resilience for tomorrow.

“With public sentiment, nothing can fail,” Abraham Lincoln said, “without it nothing can succeed.” Such a leader is inseparably linked to the people. Such leadership is a mirror in which the people see their collective reflection.”

Trump, for all his faults, had a very strong grip over his base. It’s how he got them to riot in the first place. If he had the same sway over the whole country, he would have won reelection. No matter how good an idea / product / person is, if it can’t succeed without gaining meaningful popularity.

“In the end, the unending strain with his father enhanced, rather than diminished, young Lincoln’s ambition. Year after year, as he persevered in defiance of his father’s wishes, managing his negative emotions and exercising his will to slowly master one subject after another, he developed an increasing belief in his own strengths and powers.”

Lincoln’s father did not want him getting an education - instead directed him to work on the family farm or in town to earn money. He was incredibly harsh and would beat Lincoln when he disobeyed his father - some speculate this gave Lincoln a greater appreciation for the struggles of slaves - and it also seemed to develop within a inner strength for his future trials.

“What had become of the singular ascending ambition that had driven young [Theodore] Roosevelt from his earliest days? What explains his willingness, against the counsel of his most trusted friends, to accept seemingly low-level jobs that traced neither a clear-cut nor a reliably ascending career path? The answer lies in probing what Roosevelt gleaned from his crucible experience. His expectation of and belief in a smooth, upward trajectory, either in life or in politics, was gone forever. He questioned if leadership success could be obtained by attaching oneself to a series of titled positions. If a person focused too much on a future that could not be controlled, he would become, Roosevelt acknowledged, too “careful, calculating, cautious in word and act.” Thereafter, he would jettison long-term career calculations and focus simply on whatever job opportunity came his way, assuming it might be his last. “Do what you can, with what you have, where you are,” he liked to say. In a very real way, Roosevelt had come to see political life as a succession of crucibles—good or bad—able to crush or elevate. He would view each position as a test of character, effort, endurance, and will. He would keep nothing in reserve for some will-o-the-wisp future. Rather, he would regard each job as a pivotal test, a manifestation of his leadership skills.”

What if we stopped planning out our lives and treated every project, every relationship, every job as if it was the most important thing. That it was all that mattered? Because given where the country is going, Teddy’s approach makes a lot of sense.

“To compound the innovative nature of the new administration, Eleanor Roosevelt held her own first press conference at the same time that day. She made a rule that only female reporters could attend, which meant that all over the country conservative publishers had to hire their first female reporters. Indeed, because of Eleanor Roosevelt’s weekly press conferences, an entire generation of female journalists got their start.”

While we might not have had many recently, there are good “unprecedented” moments too.

“[Franklin] Roosevelt had adapted all his life to changing circumstances. The routine of his placid childhood had been disrupted forever by his father’s heart attack and eventual death. Told he would never walk again, he had experimented with one method after another to improve his mobility. So now, as Roosevelt campaigned for the presidency, he built on his own long encounter with adversity: “The country needs and, unless I mistake its temper, the country demands bold, persistent experimentation. It is common sense to take a method and try it: If it fails, admit it frankly and try another. But above all, try something.”

Let’s use this moment to build our own collective resilience.

Get the whole book: Leadership: In Turbulent Times


👉 Check out: Annual Review

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The new year is a great time to use the Fresh Start principle, which tells us that human beings like to make changes based on meaningful dates - first day of the week, first week of the month, birthdays, anniversaries, and the beginning of the year.

I developed a process called the Annual Review, which has 3 steps: Reflect Back, Take Stock, and Look Ahead. It takes about 3 hours and helps you get in the right mindset for the year to come and extract lessons and celebrate accomplishments from the past 12 months. It’s been helped more than 61k people since I first published in 2017.

You can read or listen to it here: How to Run Your Own Annual Review


It’s been great writing Making Connections for you every week and I’m excited to continue this in 2021. If you like what we’re doing here, please forward it along to 1-2 friends you think would appreciate it?

-Jason


👨🏻‍💻 About Jason

Jason Shen is a veteran technologist on a mission to rewire our most important algorithms: the ones in our heads. As a serial founder, his companies were backed Y Combinator, Techstars, and Betaworks. As an operator, he’s built products and led teams at Facebook, Etsy, and the Smithsonian. He has bylines in Vox, Quartz, Fast Company, and his TED talk on the future of hiring has been viewed over 4 million times and been translated in 31 languages. A former NCAA gymnastics champion, Jason lives in Brooklyn with his wife, two kettlebells, and many large stacks of books.

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Jason Shen

Human(e) technologist on a mission to help build resilient teams and organizations. Former NCAA gymnast and three-time startup founder.