Ambition underdogs and empathy3Ambition underdogs and empathy


If you have a desire to leave a legacy solving important and complex problems in society you’ll probably find the April reading list pick interesting.

The Recharted Territory reading for April was Part I of “Team of Rivals: The Political Genius of Abraham Lincoln” by Doris Kearns Goodwin. We’ll finish up Part II in May so there’s still time to catch up.

Part I of the book covers the events leading up to Lincoln’s presidential inauguration. The author describes Lincoln’s life and choices in comparison to his Republican rivals for the nomination: William Henry Seward, Salmon Chase, and Edward Bates. The book follows the rivals from childhood through their early careers, hitting on events of the time, their relationships, public actions, and private reflections. I thought it was especially interesting to read about their internal struggles and external choices in the decades leading up to the Civil War.

Since Part I of “Team of Rivals” covers the lives of leaders before they gained their biggest platform to influence a complex problem, it seemed perfect for Recharted Territory readers. While the rivals were living and working over 150 years ago, many of the themes are still relatable today.

The author weaves together the stories of Lincoln and his rivals, referencing letters, publications of the time, and observations of other historians. One of the overarching themes that I noticed was the idea of balance.

Balancing ambition and happiness. Empathy and melancholy. Extremism and centrism. Being an underdog and leader.

There’s a sense of tension, that it’s a constant tightrope walk for the politicians, both politically and internally. I’ve seen similar feelings expressed by intrapreneurs, entrepreneurs, and creatives so it would be interesting to look at how the rivals approached this tension and used it to achieve their goals. Sometimes it helps to know that even great historical leaders dealt with the same emotions that we’re going through.


Managing ambition and disappointment

All of the rivals were influenced by their ambition. Lincoln’s dream was to be recognized and respected by his fellow citizens. As settlers were expanding westward, young people were constantly looking for ways to improve their status or carve out a legacy for themselves. Sound familiar? Lincoln himself wondered what was left for his generation to accomplish after everything the founding fathers did.

One of Lincoln’s rivals, Edward Bates, describes his thoughts about ambition as he ponders whether he’ll run for president,

“Ambition is a passion, at once strong and insidious, and is very apt to cheat a man out of his happiness and true respectability of character.”

– Bates

When reality didn’t match their ambition’s expectations, the rivals wrestled with disappointment. Before winning the Presidential election Lincoln lost two elections for Senate and had only a single term in Congress. They all dealt with losing elections and watching other people rise while their own political career wavered. They also all defined success by external indicators to some degree and were heavily influenced emotionally by defeat and career disappointment.

During periods of extreme disappointment or loss, they spent time reevaluating their lives. Seward falls into a melancholy state, worried that his ambition hurt his relationship with his wife. Lincoln becomes depressed when his personal life and professional life seem to be moving backward.

Sometimes ambition was both the cause of unhappiness and the way out of it. In Goodwin’s words,

“the strength of Lincoln’s desire to engrave his name in history carried him forward.”

– Goodwin on how Lincoln overcame depression

He decided that he needed to keep going to realize the legacy that his ambition was pushing him to achieve. He shared with friends that he tried to avoid dwelling on his anxiety by staying busy, focusing on his work and building relationships.

Lincoln’s career had highs and lows, but his story shows that disappointment doesn’t need to be permanent if your follow-up actions are positive. When the doors of his career are temporarily closed because of his criticism of the president after the Mexican War, Lincoln returns to life as a lawyer in Illinois while his rivals continue their political careers. Traveling around the state and networking with locals ended up helping him greatly in the 1860 election.

Lincoln also turned to self-improvement when faced with disappointment. When he gets replaced by a new lawyer for a high-profile case, Lincoln observes the lawyer (Edwin Stanton) in action and decides that he should study more to improve his skills. Later on, Lincoln offers Stanton Secretary of War and Stanton eventually begins to admire and respect Lincoln. While disappointment cut deep at the time, Lincoln and his rivals kept moving and eventually their careers turned around as well.

Application to daily life

In the rivals’ case, managing ambition became a delicate balance of fueling their drive while not sacrificing their health, relationships, or character. At their lowest points, they all turned to self-reflection to check back in with their ambition and how it was impacting them.

If you also find yourself with a love/hate relationship with your ambition, try answering these questions:

  • What is your personal definition of success?
  • Why do you want to achieve that definition of success?
  • Are you making progress towards success?
  • Have you had any failures or setbacks in your journey? How did they make you feel?
  • Does your definition of success need to change? Reflect monthly. (Note: This exercise may help you if you’re feeling behind, unhappy, or in a funk and you’re not sure how to get out of it. I find this exercise to be the most helpful when I realize that I’m letting my happiness be dictated by other people’s definitions of success rather than my own.)
  • What small actions can you take to work towards your definition of success? Disappointment in one moment doesn’t mean that you’re destined for that disappointment forever, as Lincoln proved. What actions can you take to move closer, improve your skills, or set yourself up for future opportunities?


Being an underdog

For all of the underdogs out there, Lincoln is a great role model. According to Goodwin, people were prone to underestimating him, given his background and looks. However, once they got to know him or heard his eloquent speeches and humorous stories, many quickly changed their mind.

Lincoln used his underdog status to his advantage in the 1860 election cycle by delaying his announcement for the candidacy, which caused his Republican rivals to lower their guard and campaign less. Under the radar, he was working, visiting locals, and building relationships that would become invaluable during the election. He published his popular debates with Stephen Douglas in a book that was distributed and read in Republican circles. The debates got newspaper coverage and he was invited to speak at other events. He became known as a thought leader.

His goal was to become everyone’s second choice, which because of the division of the Republican party, meant that he ended up winning the majority of the delegates. He also never criticized other candidates and repaired relationships to avoid enemies. Other candidates paid less attention to slighted parties and it ended up hurting them when the delegates sat down to vote. Strategically playing the underdog, not making enemies, and staying consistent instead of switching platforms to gain votes, ended up playing a large role in Lincoln’s election.

Application to daily life

With today’s media, we are bombarded with information about people who seem to be “ahead” of us. Do you feel like an underdog? That might actually be a great position to be in. Take inspiration from Lincoln and use your underdog status to your advantage.

  • Write down the advantages that you have and how you could use your underdog position to advance your cause or goals. Lincoln’s advantage was the element of surprise. Since none of his competitors saw him as a threat, he could work towards being everyone’s second choice without alarming his rivals. By the time he went public with his candidacy he had already obtained support and avoided creating enemies.
  • Write down the disadvantages that you have, and what you would do to improve. For example, Lincoln was less well-known so he focused on sharing his message and creating quality speeches. He used the media tools at the time to share his speeches and debates with a wider audience so that they were aware of his viewpoint. He also focused on creating the best content possible and would spend weeks writing the perfect speeches that would resonate with his audiences.


Meeting people where they are

Lincoln was successful in politics because of his ability to empathize and to use those insights when crafting his message. He would imagine what his enemies were feeling and how they would react. Lincoln recognized that criticizing someone for what he believed in and how he behaved would just cause him to,

“retreat within himself, close all avenues to his head and his heart.”

– Lincoln, on people’s reaction to being criticized for their beliefs and behaviors

According to him, appealing to someone’s heart was the best way to attract him to your cause. Lincoln employed this technique in his speeches about the Nebraska Act. He used logic to point out the inconsistencies in southern behavior in order to draw out their underlying thoughts and feelings, instead of directly attacking their beliefs.

He also used empathy to tailor the imagery in his speeches. When speaking to the masses he would use metaphors that referenced home life and would resonate with anyone listening. This was in sharp contrast to his rival Seward’s references to classic literature. Lincoln spoke,

“As if the people were listening to their own thinking out loud.”

– James Russell Lowell on Lincoln’s ability to speak to crowds

Application to daily life

If your message just isn’t sticking (or tensions are high), try these tips:

  • If you’re clashing with someone but you need to work together to accomplish a common goal, try following Lincoln’s lead and think about what her concerns and needs are. Try reframing your argument to show how it benefits or fits with what she already believes. Or ask questions or point out facts or inconsistent logic to help her realize what her underlying needs and beliefs are.
  • The longer we stay in a field, the harder it is to realize how much jargon we’re using. Try keeping a thesaurus of commonly used terms in your industry and plain English equivalents. Also, try keeping a notebook of metaphors or stories that you can pull out to illustrate a point. You might want a different set of metaphors for different types of people.


Related reading

Throughout our changemaker careers, but especially early on, we’re dealing with managing our ambition and reality vs. expectations. We are probably an underdog and underestimated. And we’re looking for ways to connect with people who have vastly different worldviews when we have no direct authority to influence their actions. “Team of Rivals” provided a glimpse into how Lincoln and his rivals addressed these same concerns in the 19th century. Check out these resources if you’re interested in more information related to these themes:


What other insights did you draw from Part I of this book? How will you apply them?


Share your thoughts