# Medium Headlines + Subtitles

**ARTICLE TOPIC:**
Lessons learned from failing at 3 startups before building one that made $2M

**ARTICLE TYPE:**
Personal Experience/Lessons Learned

**TARGET AUDIENCE:**
Entrepreneurs, startup founders, people considering starting a business

**KEY ANGLE:**
Failure as a teacher, specific lessons, eventual success

---

## HEADLINE SET 1: PERSONAL STORY + NUMBERS

### Headline:
```
I Failed at 3 Startups Before Building One That Made $2 Million — Here Are the 7 Lessons That Changed Everything
```
**Character Count:** 113

### Subtitle:
```
The expensive education nobody talks about — and why I'm grateful for every failure
```
**Character Count:** 86

### Why This Works:
- **Specific numbers** (3 startups, $2M, 7 lessons) create credibility
- **Contrast** (failed → made $2M) creates curiosity
- **Here Are** promises concrete takeaways
- **Subtitle adds emotion** (grateful for failure = unexpected angle)

### Best For:
Readers who value specific, actionable insights from real experience

---

## HEADLINE SET 2: COUNTERINTUITIVE HOOK

### Headline:
```
My 3 Failed Startups Taught Me More Than My $2 Million Success Ever Could
```
**Character Count:** 75

### Subtitle:
```
The counterintuitive lessons I wish someone had told me before I lost everything (twice)
```
**Character Count:** 91

### Why This Works:
- **Counterintuitive claim** stops the scroll (failures > success?)
- **Shorter headline** = punchier, more shareable
- **Subtitle adds stakes** (lost everything, twice)
- **Parenthetical** adds specificity and intrigue

### Best For:
Readers drawn to unconventional wisdom and contrarian takes

---

## HEADLINE SET 3: DIRECT FORMAT

### Headline:
```
How I Went From 3 Failed Startups to a $2 Million Exit (And What Finally Made the Difference)
```
**Character Count:** 96

### Subtitle:
```
A brutally honest look at what I got wrong — and the mindset shift that changed my trajectory
```
**Character Count:** 95

### Why This Works:
- **How I** = proven high-performing format on Medium
- **Journey structure** (from X to Y) promises transformation
- **Parenthetical teaser** (what finally made the difference)
- **Subtitle promises honesty** (brutally honest) = trust

### Best For:
Readers looking for practical, replicable approaches

---

## HEADLINE SET 4: LISTICLE ANGLE

### Headline:
```
7 Hard Lessons From 3 Failed Startups That Led to My First $2 Million Business
```
**Character Count:** 81

### Subtitle:
```
The painful mistakes I made (so you don't have to) and the frameworks that finally worked
```
**Character Count:** 93

### Why This Works:
- **Number first** (7) signals scannable, structured content
- **Hard Lessons** = earned wisdom, not theory
- **Subtitle offers reader benefit** (so you don't have to)
- **Frameworks** promises actionable takeaways

### Best For:
Readers who prefer structured, skimmable content

---

## HEADLINE SET 5: CURIOSITY GAP

### Headline:
```
What 3 Failed Startups Taught Me About Success That Business School Never Will
```
**Character Count:** 81

### Subtitle:
```
After losing $400K and 6 years, I finally understood what actually matters in entrepreneurship
```
**Character Count:** 96

### Why This Works:
- **Curiosity gap** (what did failures teach about success?)
- **Business school contrast** = relatable frustration
- **Subtitle adds specific stakes** ($400K, 6 years)
- **Actually matters** promises insight through the noise

### Best For:
Readers skeptical of conventional advice, seeking real-world wisdom

---

## HEADLINE SET 6: EMOTIONAL HOOK

### Headline:
```
I Lost Everything 3 Times Before Building a Business Worth $2 Million — Here's What Nobody Tells You About Failure
```
**Character Count:** 118

### Subtitle:
```
The unglamorous truth about startup failure and the moment I almost gave up for good
```
**Character Count:** 87

### Why This Works:
- **Emotional stakes** (lost everything, 3 times)
- **Nobody tells you** = insider knowledge promise
- **Subtitle adds vulnerability** (almost gave up)
- **Longer headline works** because it's compelling throughout

### Best For:
Readers seeking emotional connection and authentic stories

---

## HEADLINE SET 7: SIMPLE + PUNCHY

### Headline:
```
3 Failures, $2 Million in Lessons, and the Truth About Startup Success
```
**Character Count:** 70

### Subtitle:
```
What 8 years of entrepreneurial failure finally taught me about building something that works
```
**Character Count:** 95

### Why This Works:
- **Short, rhythmic headline** (3 elements, easy to read)
- **Comma structure** = easy scanning
- **Truth about** = promise of real talk
- **Subtitle expands** with timeframe (8 years)

### Best For:
Mobile readers, shares on social media

---

## HEADLINE SET 8: QUESTION FORMAT

### Headline:
```
What Do 3 Failed Startups and a $2 Million Exit Have in Common? More Than You Think.
```
**Character Count:** 85

### Subtitle:
```
The surprising thread connecting my worst failures to my biggest success
```
**Character Count:** 73

### Why This Works:
- **Question creates curiosity** (I need to know the answer)
- **More than you think** challenges assumptions
- **Subtitle teases** (surprising thread) without revealing
- **Shorter subtitle** lets headline do the work

### Best For:
Readers who enjoy puzzle-solving, discovering connections

---

## KICKER OPTIONS

Small text that appears above headline (optional but powerful):

```
1. A Startup Founder's Confession
2. Lessons in Entrepreneurship
3. The Unglamorous Truth
4. What I Wish I'd Known
5. A Personal Essay
```

**When to Use Kickers:**
- Adds context for ambiguous headlines
- Creates series feel (Part 1, Part 2)
- Signals article type (Essay, Analysis, Guide)
- Use sparingly—not every article needs one

---

## HEADLINE FORMULA LIBRARY

### Formula 1: Personal Story + Outcome
```
I [Did X] for [Time Period] — Here's What [Happened/I Learned]
```
**Examples:**
- I Wrote Every Day for 365 Days — Here's What It Did to My Career
- I Quit Social Media for 6 Months — Here's What Happened to My Mental Health
- I Cold-Emailed 100 CEOs — Here's What Actually Got Responses

---

### Formula 2: Number + Hard Truth
```
[Number] [Adjective] Lessons About [Topic] That [Consequence/Outcome]
```
**Examples:**
- 7 Hard Lessons About Entrepreneurship That Cost Me $200K
- 5 Uncomfortable Truths About Writing That Nobody Wants to Hear
- 12 Painful Lessons About Leadership That Made Me a Better Manager

---

### Formula 3: Achievement Story
```
How I [Achieved Impressive Result] (And [Additional Hook])
```
**Examples:**
- How I Grew to 50,000 Followers in 6 Months (And What I'd Do Differently)
- How I Built a $1M Business Working 4 Hours a Day (Without Sacrificing Family Time)
- How I Learned to Code in 3 Months (With No Technical Background)

---

### Formula 4: Counterintuitive Take
```
Why [Common Belief] Is [Wrong/Incomplete] — And What to Do Instead
```
**Examples:**
- Why Follow Your Passion Is Terrible Career Advice — And What Actually Works
- Why Working Harder Won't Make You Successful — And What Will
- Why Most Productivity Advice Is Backwards — And What Top Performers Do Instead

---

### Formula 5: What X Taught Me About Y
```
What [Unexpected Experience] Taught Me About [Related Topic]
```
**Examples:**
- What Training for a Marathon Taught Me About Building a Business
- What My Biggest Failure Taught Me About Success
- What Living Abroad Taught Me About American Work Culture

---

### Formula 6: The X Guide/Framework
```
The [Adjective] Guide to [Topic] That [Benefit/Differentiator]
```
**Examples:**
- The No-BS Guide to Getting Your First 1,000 Email Subscribers
- The Unconventional Framework That Helped Me Write 3 Books in One Year
- The Simple System for Productivity That Actually Sticks

---

### Formula 7: Confession/Vulnerability
```
I [Vulnerable Admission] — [What I Learned/What Happened]
```
**Examples:**
- I Was Fired From My Dream Job — It Was the Best Thing That Ever Happened
- I Spent 5 Years Building the Wrong Business — Here's How I Course-Corrected
- I Used to Think I Was a Great Leader — Then I Got Honest Feedback

---

### Formula 8: The Unexpected Discovery
```
I [Did Research/Experiment] and Discovered [Surprising Finding]
```
**Examples:**
- I Analyzed 500 Viral Medium Articles and Discovered 3 Patterns They All Share
- I Interviewed 50 Millionaires and Found They All Do This One Thing
- I Tracked My Habits for 90 Days and Discovered Why I Was Always Tired

---

## SUBTITLE STRATEGIES

### Purpose of Subtitle:
1. **Add a second hook** (different angle than headline)
2. **Provide context** (when headline is cryptic)
3. **Add emotion** (vulnerability, stakes)
4. **Promise value** (what reader will get)
5. **Create contrast** (unexpected twist)

### Subtitle Formulas:

**Formula A: Stakes + Promise**
```
The [stakes/cost] of [topic] — and [what you'll learn]
```
*Example: The $400K mistake that changed everything — and the framework that finally worked*

**Formula B: Honesty Hook**
```
A [honest/brutally honest/candid] look at [topic]
```
*Example: A brutally honest look at what it really takes to build a business*

**Formula C: Reader Benefit**
```
[What you'll learn] so you [can avoid/achieve X]
```
*Example: What I wish I'd known so you don't make the same mistakes*

**Formula D: Emotional Add**
```
The [emotion] [story/truth] behind [topic]
```
*Example: The painful truth behind every overnight success*

**Formula E: Unexpected Angle**
```
Why [unexpected thing] is [surprising claim]
```
*Example: Why my biggest failure was actually my best investment*

---

## HEADLINE LENGTH GUIDE

| Length | Characters | Performance | When to Use |
|--------|------------|-------------|-------------|
| Short | 40-60 | High CTR, shareable | Strong single hook |
| Medium | 60-90 | Optimal balance | Most articles |
| Long | 90-120 | Can work with strong content | Complex stories |
| Very Long | 120+ | Risky, often cut off | Avoid unless compelling |

**Sweet Spot:** 60-90 characters

**Mobile Note:** Headlines over 100 characters may be truncated on mobile

---

## POWER WORDS THAT WORK ON MEDIUM

### Credibility Words:
```
Data, Research, Study, Analysis, Experiment, Tracked, Tested, Discovered, Interviewed, Analyzed
```

### Emotion Words:
```
Failed, Lost, Painful, Brutally, Honest, Uncomfortable, Hard, Struggle, Fear, Risk
```

### Curiosity Words:
```
Secret, Hidden, Nobody, Surprising, Unexpected, Counterintuitive, Actually, Really, Truth
```

### Value Words:
```
Lesson, Framework, System, Guide, Blueprint, Formula, Strategy, Method, Approach
```

---

## COMMON HEADLINE MISTAKES

| Mistake | Example | Fix |
|---------|---------|-----|
| Too vague | Thoughts on Success | What 10 Years of Failure Taught Me About Success |
| No hook | My Startup Journey | I Failed 3 Times Before My Startup Made $2M |
| Clickbait with no payoff | You Won't Believe What Happened | What Happened When I Quit My Job at 25 |
| No specifics | How to Be More Productive | How I 10x'd My Output in 30 Days |
| Too long | 150+ characters | Cut to under 100, move excess to subtitle |
| Repeating subtitle | Headline and subtitle say same thing | Make subtitle add new angle |
| Missing subtitle entirely | Blank subtitle | Always add compelling subtitle |