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Part 2 · Episode 17 B1-B2

I Should Have Listened

📐 should have (regret/criticism)

Napoleon Bonaparte · 1815: Napoleon after Waterloo 📖 6 min read

Episode 17: I Should Have Listened

should have: regret — Napoleon after Waterloo, 1815 (B1-B2)

Grammar Box

Meaning: “Should have + past participle” expresses regret about past actions or criticism of what wasn’t done—when something was the right thing to do but didn’t happen.

Form: should have + past participle; shouldn’t have + past participle

Example 1: “I should have studied harder for the exam.” (regret about insufficient effort)

Example 2: “He shouldn’t have said that.” (criticism of wrong action that happened)

Common mistake: Wrong: “I should have went earlier.” Better: “I should have gone earlier.” (past participle, not simple past)

The Challenge

Luna looked at her rejected job application and sighed. “I didn’t prepare well enough,” she said sadly. Professor Wisdom appeared beside her. “Is there a way to express that you recognize the mistake now, looking back?” Luna thought about how to capture both the past action and her current regret about it. The watch glowed with a melancholy light, taking them to a moment when one of history’s most powerful men faced the crushing weight of wrong decisions.

The Journey

Napoleon Bonaparte sat in exile on the remote island of Saint Helena in 1815, thousands of miles from the glory he had once commanded. The former Emperor of France, who had ruled much of Europe, now occupied a damp house on a windswept island in the South Atlantic. His defeat at Waterloo in June 1815 had ended his final bid for power, and in the lonely years that followed, he had nothing but time to reflect on the decisions that led to his downfall.

“I should have listened to my marshals,” Napoleon admitted to Count de Las Cases, who recorded the emperor’s memoirs during exile. “They warned me that the troops weren’t ready for another campaign so soon after my return from Elba. I shouldn’t have been so confident.” His voice carried the bitter knowledge that comes too late—the understanding of what should have been done differently.

The list of regrets grew as Napoleon reviewed his strategic decisions at Waterloo. “I should have pursued the Prussians more aggressively after Ligny,” he reflected, referring to the battle two days before Waterloo. “If I had, they couldn’t have rejoined Wellington’s forces at the crucial moment. I shouldn’t have waited so long to begin the attack on the morning of Waterloo—the delay gave Blücher time to arrive with reinforcements.”

Each “should have” represented a moment where better judgment existed but wasn’t followed. Unlike “could have,” which speaks to missed possibilities, “should have” carries moral weight—these weren’t just opportunities but right courses of action that wisdom or duty demanded. “I should have consolidated my power in France instead of invading Russia in 1812,” Napoleon said, touching the source of his ultimate decline. “That campaign shouldn’t have happened. It destroyed my Grand Army.”

The smell of sea salt filled his modest quarters, so different from the palaces he once inhabited. Rain drummed against the windows as he paced, reviewing battles and decisions with the clarity that hindsight provides. “I shouldn’t have divorced Josephine,” he said quietly, referring to his first wife. “I should have valued her counsel more. I shouldn’t have trusted certain advisors who flattered rather than challenged me.”

His doctor noticed how Napoleon’s health declined alongside these reflections. The emperor who had conquered nations couldn’t conquer his own regrets. “Everyone around me can say ‘I told you so’ now,” Napoleon said bitterly. “They should have insisted more strongly. I shouldn’t have ignored them.”

The Deep Dive

“Should have + past participle” expresses that something was the right action but didn’t happen (regret), or the wrong action but did happen (criticism). “I should have called her” means calling was the right thing to do but you didn’t do it. “I shouldn’t have eaten so much” means eating that much was wrong but you did it anyway. Both forms express current judgment about past actions, combining what happened then with what you know now.

The emotional content distinguishes “should have” from other past modals. “Could have” speaks to possibility (“I could have been a doctor”—it was possible), while “should have” speaks to rightness or wisdom (“I should have studied medicine”—it was the right choice). “Must have” expresses deduction (“He must have known”—logical certainty), while “should have” expresses obligation or wisdom not followed (“He should have told me”—moral or practical duty).

Use “should have” for personal regrets, constructive criticism, and analyzing past mistakes. It’s softer than “had to” (actual obligation) but stronger than “could have” (mere possibility). The construction works for advice about the past: “You should have seen a doctor sooner” criticizes delay. It also works for missed opportunities where hindsight reveals the better path: “They should have invested in that company—it’s worth millions now.” Don’t confuse “should have” with “should of”—this is a common spelling error since they sound similar in speech.

More Examples

History: “Churchill later said Britain should have confronted Hitler earlier, before Germany became too powerful.” (historical regret)

Science: “The Challenger crew shouldn’t have launched in those cold conditions—engineers had warned about the O-rings.” (tragic criticism)

Everyday: “I should have brought an umbrella. Now I’m completely soaked.” (simple regret)

Formal: “The company should have conducted more thorough due diligence before the merger.” (professional criticism)

Informal: “We shouldn’t have stayed up so late! I’m exhausted.” (mild self-criticism)

Contrast: “I didn’t study” (simple fact) vs “I should have studied” (regret about not studying) vs “I could have studied” (possibility existed)

Practice & Reflection

Exercises:

  1. Fill in the blank: I __ (should have/must have) called you yesterday—I apologize for forgetting.

  2. Correct the mistake: “She should have went to the doctor when she first felt sick.”

  3. Choose and explain: Which expresses regret about the past?
    a) “I could have finished earlier.”
    b) “I should have finished earlier.”

  4. Rewrite: Express regret: “I didn’t save money when I had the chance, and now I regret it.”

  5. Compare: Explain the difference: “I could have told him” vs “I should have told him.”

  6. Your reflection: Think of a decision you regret. Write about it using should have or shouldn’t have.

Answer Key:
1. should have called (expresses regret/apology for not doing it)
2. She should have gone to the doctor (past participle “gone,” not “went”)
3. (b) — “should have” expresses it was the right thing to do (regret); “could have” just notes possibility
4. I should have saved money when I had the chance (expresses current regret about past inaction)
5. First notes possibility; second adds moral/practical judgment that it was the right thing to do
6. Check: Does should/shouldn’t have + past participle express regret or criticism about past?

The Lesson

Luna looked at her application again with new understanding. “I should have prepared better,” she told Professor Wisdom. “I shouldn’t have rushed through the answers. Now I know what to do differently next time.” The Professor nodded gently. “Exactly. Napoleon’s tragedy was recognizing too late what he should have done. But your ‘should have’ isn’t just regret—it’s learning. You’re using past mistakes to inform future wisdom. That’s the productive use of should have: not dwelling on unchangeable past, but extracting lessons for better choices ahead.”