The year is 49 BCE. Julius Ceaser had been proconsul of Gaul for nearly a decade, building a powerful army and personal fame. His term was ending, and Roman law required generals to disband their troops before re-entering Italy. The Senate, under Pompey’s influence, ordered him to lay down his command.
If he obeyed the Senate’s command and returned to Rome as a private citizen, he risked prosecution by his enemies, notably Pompey and Cato, who accused him of war crimes and corruption. Without his army, he had no protection.
If he defied the Senate and marched his army into Italy, it would be considered an outright rebellion. He would be seen as a traitor and an instigator of a civil war, an offense punishable by death.
Either path threatened ruin. Caesar stalled, sending envoys and offering compromises, like running for consul in absentia. Each was rejected.
Time was running out: if he hesitated, Pompey’s legions would outmaneuver him, and his political enemies would indict him.
What should he do: risk personal destruction through obedience, or national destruction through defiance?
A few years later, in 1862, Abraham Lincoln was facing one of the toughest Civil War dilemmas: whether and when to issue the Emancipation Proclamation.
Issuing emancipation immediately would strike a bold moral blow against slavery, aligning the Union cause with the principle of human freedom and galvanizing abolitionist support. It could weaken the Confederacy by encouraging enslaved people to flee plantations, depriving the South of labor, and strengthening the Union war effort. Yet the risks were immense: the border states, still loyal to the Union but dependent on slavery, might secede and join the Confederacy. Northern public opinion, divided and fragile, could fracture, leaving Lincoln accused of transforming a war to save the Union into an abolitionist crusade many were not prepared to fight. Acting now promised moral clarity but risked political and military collapse.
Holding off would preserve the delicate coalition, keeping the Union intact. By avoiding a sudden shift in the war’s aims, Lincoln could maintain the loyalty of border states and Northern soldiers whose primary motivation was saving the Union, not ending slavery. It would also prevent Confederate sympathizers from painting emancipation as a desperate ploy. Yet delay carried its own costs: each passing day meant continued bondage for millions, accusations of cowardice from abolitionists, and the possibility that history would judge Lincoln as timid in the face of moral crisis. Waiting promised political stability, but it risked the loss of purpose, momentum, and the chance to redefine the Union’s struggle as one of freedom as well as unity.
Then, there is you, trying to decide if you should buy another big TV or a new car, where to go on vacation, whether or not you should buy your kids a house, and if it’s time for assisted living yet. You struggle with decisions about your job, friends, retirement, and what’s the best cereal, best diet, best way to lose weight without exercising.
Many people frequently find themselves in the peculiar position of acting like an ass, Buridan’s ass from the famous parable, sitting between a couple of great bales of hay, unable to choose which one to eat and passing out from starvation. It could look like spending two hours at Best Buy evaluating options and walking out empty-handed. Or reading hundreds of Amazon reviews for a $50 product and then abandoning the purchase.
Sometimes, like Hamlet, who stewed in indecision, wondering, “To be or not to be,” until life forced a duel upon him, we get stuck with whatever happens when we don’t choose ourselves. But just like him, meeting the poisoned sword of his opponent, we may not fare any better riding in the passenger seat in a car we should be driving.
Why is it so hard to make decisions
We think that having more choices is better. Therefore, we try to give ourselves more choices. No one wants to walk into the supermarket and see just one brand and type of cereal. Condoms come in hundreds of varieties, even though they all do one thing one time only. Health insurance options stress you out as soon as you need to pick a plan, even a free one. When your employer gives you free money, matching your 401K, you still have a long list of possible investment options to put that money into. And when you finally have a chance to unwind in front of your TV, you have several hundred channels and thousands of movies to choose from.
Not all choices we make are as easy as picking a movie to watch. Some determine the quality and trajectory of our lives and the lives of people we care about. Like when I had to decide if I should go to Stanford or Whittier College, or get married, or work for Morgan Stanley as an investment banker. Chances are, you wouldn’t be reading this if I had chosen differently… But here we are.
Choices overload, demonstrated by Sheena Iyengar & Mark Lepper, showed that when shoppers were offered 24 flavors of jam, fewer bought than when offered only 6. That’s because having more than six choices apparently overwhelms cognitive capacity, making it hard to compare and rank your options. We feel fatigued and frequently end up avoiding having to decide, even walking away empty-handed.
Similarly, we feel information overload when decisions require sifting through complex or conflicting information, such as medical choices, investments, or tech purchases; people often freeze.
In addition to choice overload and information overload, several other factors correlate with decision difficulty, according to researchers like Mary Steffel and Elenor F. Williams:
When the options are similar in attractiveness, we find it hard to tell which is “best.”
When there’s a high risk of regret, the more one worries “if I pick A, maybe B would’ve been better.”
When deciding means owning responsibility for a possibly bad outcome. The emotional weight of being “at fault” matters.
Choosing one option closes the door on others, triggering loss aversion. It’s an opportunity cost we have to accept, but it often comes with FOMO. Even if we think we are choosing well, we obsess over the “path we won’t take,” which keeps us stuck in indecision.
Some studies show that after making many decisions, self-control and willpower wane. That’s because of what scientists call Decision fatigue - the idea that the more decisions you make, the harder it becomes to make subsequent ones well. Every choice, big or small, draws from a limited pool of mental energy. With the energy depleted, people either avoid deciding or default to the easiest, often suboptimal choice or the status quo.
This is why you might spend hours researching a new laptop but then order the same takeout you always do — your “decision budget” is already spent.
Willpower and self-control are like muscles. They also tire with use. Making decisions, resisting temptation, or even managing emotions consumes this energy. A famous study showed that parole judges in Israel were more likely to grant parole early in the day or immediately after lunch, but approvals declined before breaks. The takeaway: mental resources eroded over time, leading judges to fall back on the safest, default decision — deny parole.
Meanwhile, for perfectionists, no option is ever “good enough.” They endlessly search, revise, and second-guess themselves. They refuse to commit because the “perfect” solution might still be out there.
Some decisions threaten how we see ourselves. Humans have a deep drive to see themselves as coherent and consistent. If different options validate different self-concepts, choosing one feels like betraying the other. For example, choosing family over career may feel like betraying ambitions. But choosing a career over family feels like betraying family values.
Also, people carry mental images of who they might become. When decisions pit one “possible self” against another, it creates a tug-of-war that feels unresolvable. (I wrote about that in Who Am I Now.) Just like we fear losing money, we fear losing parts of our identity.
Too little time also amplifies indecision because stress narrows focus. Under stress, the prefrontal cortex (responsible for weighing trade-offs) gets less effective, while the amygdala (fear center) takes over. This shrinks our ability to see nuance. Cortisol spikes impair working memory and flexible thinking, making complex comparisons harder. With little time, any mistake feels more dangerous, which can push people to freeze rather than choose.
How to “beat” Buridan’s ass
In January 49 BCE, Caesar moved his 13th Legion south to the Rubicon River, the legal boundary between his province (Cisalpine Gaul) and Italy proper. Roman law was crystal clear: a general who crossed the Rubicon with an army became an enemy of the state.
He crossed, choosing bold action over paralysis, supposedly uttering “The die is cast.” Historians argue that Caesar broke the deadlock by reframing the situation. While both paths were dangerous, obedience meant certain political and personal ruin; rebellion offered at least a chance of survival and glory. Caesar’s self-concept as a commander, statesman, and near-mythic figure pushed him toward action over humiliation. Armies, like decisions, lose energy if stalled. By moving quickly, he seized the initiative before Pompey could consolidate power.
His choice launched the Roman Civil War (49–45 BCE). Pompey and the Senate fled Rome almost immediately, showing Caesar’s gamble had paid off in the short term. Within a few years, Caesar emerged as dictator, reshaping Rome until his assassination in 44 BCE. So, what looked like an impossible stalemate became the decisive turning point of his life and Roman history.
We use “crossed the Rubicon” as an expression of “point of no return.” Once Caesar marched his legion over the Rubicon in 49 BCE, he broke Roman law and triggered civil war. There was no undoing it.
In July 1862, Lincoln had already drafted a preliminary Emancipation Proclamation, freeing enslaved people in Confederate-held territory. He even read it to his cabinet. He had a reputation for deliberating endlessly, letting cabinet members argue things out. He leaned on his “team of rivals” to pressure-test decisions until one option gained moral/emotional clarity for him.
Some members, like Salmon Chase, pushed for immediate action. Others feared it would look desperate after recent Union defeats. Seward, Secretary of State, told Lincoln bluntly: Don’t issue this now, after losses. It will look like the last shriek on the retreat. Better to wait for a military victory so emancipation would look like strength, not desperation.
So, Lincoln delayed issuing the Emancipation Proclamation until after Antietam, framing the choice around timing, not just the principle. On September 17, 1862, the Battle of Antietam was fought in Maryland. It wasn’t a decisive Union victory. More of a bloody stalemate. But it was enough for Lincoln to claim the momentum he needed.
Five days later, on September 22, Lincoln issued the Preliminary Emancipation Proclamation: the Confederacy had 100 days to return to the Union, or slavery would be abolished in rebel territories. On January 1, 1863, the final Emancipation Proclamation went into effect. It freed enslaved people only in Confederate-controlled areas (not in the border states), a political compromise that kept those states in the Union.
Lincoln shifted the decision from moral ideal vs. political survival to timing and optics. This let him resolve paralysis by finding the right moment. By leaning on Seward’s advice and waiting for a military “cover,” he also spread the burden of responsibility.
The delay worked:
The Union kept its fragile coalition together.
The war gained a higher moral purpose, making it harder for Britain and France to recognize the Confederacy.
Black men could now enlist in the Union army, strengthening the North’s manpower.
History shows us that even the most consequential leaders have wrestled and continue to struggle with the same paralysis we face in grocery aisles, careers, and relationships. Their choices remind us that indecision is rarely solved by finding a perfect answer but by reframing the problem, leaning on others when needed, and recognizing when the cost of waiting outweighs the risk of acting. Our daily decisions may not trigger civil wars or redefine nations, but the stakes are real in shaping the course of our lives.
Normal people can use these same strategies to make consequential decisions:
1) Be clear on your choices.
2) Identify if it is something you need to decide now or when.
3) Try to limit your options.
4) Decide what matters to you most.
5) Figure out your best and worst-case scenarios.
6) Figure out what you could delegate or if you need someone’s help.
7) Hear different opinions.
8) Pick something, even if you are not sure it’s the best thing, and commit to it.
👉 If you want to go deeper, I’ve created an expanded decision-making guide with prompts and templates to walk you through the process step by step.
Free subscribers can grab it HERE for $8. Or, upgrade to paid 😁!
Paid subscribers get it free. The link is at the end of the post below the paywall.
I have one more piece in this series on self-sabotage and procrastination. It’s coming out next week!
Following that, I would like to invite my paid subscribers to the Integration Lab session on Zoom, where we can talk about things that have made an impression on you in the last few weeks and how they might be relevant to your life. You can ask me anything. I’ll be Zooming from Bulgaria.
The Integration Lab is a free, one-hour session. I hope to have more Labs in the future, usually when I wrap up a theme I’ve been working on. I hope to see you there. I’ll post the details next week.
Thanks for reading. Feel free to share your tough choices and how you resolved them.
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