Imagine Getting Fired 5 Times by Steve Jobs—and Having the Resilience to Keep Coming Back 😵💫
How to Keep Your Sanity (and Succeed) with a Tough Boss Breathing Down Your Neck
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Imagine Getting Fired 5 Times by Steve Jobs—and Having the Resilience to Keep Coming Back 😵💫
We’ve all had that boss.
Relentless. Ruthless. Impossible to please. Sound familiar?
I’ve been there—once had a boss demand a full marketing overhaul at 10:30 pm on a Friday. There I was, racing back from the pub while everyone else was out having fun. Classic.
Startup life isn’t for the faint of heart.
If you’re dealing with a high-pressure boss—or a founder under the weight of investor expectations—this is for you.
Here's what I’ll cover:
➡️ Getting fired by Steve Jobs 5 times
➡️ Why Andy came back after five firings
➡️ How to work with a tough leader without losing your mind
➡️ How to handle your own "Steve Jobs"
➡️ My Final Thoughts
➡️ The Rabbit Hole
Getting Fired by Steve Jobs (5 Times)
Andy Cunningham’s Story
Andy Cunningham didn’t just have a tough boss—she had Steve Jobs.
He fired her five times and still rehired her.
Andy worked with him during Apple’s iconic Macintosh launch. (I wrote about her brand positioning playbook in a previous post if you want more.)
Steve Jobs was a perfectionist, demanding the best from his products, his team, and anyone who worked with him.
Andy Cunningham learned that the hard way.
The first time he fired her, he was blunt: “Your work is terrible.”
Oh, and he refused to pay her the $35,000 he owed, claiming it wasn’t worth it.
Most people would’ve walked out and never looked back.
But not Andy.
This wouldn’t be the last time Jobs fired her either.
Why Andy Came Back After Five Firings
Most would’ve quit after the first ego-crushing dismissal.
But not Andy.
She knew her value and Jobs' Achilles heel: his public image.
Jobs wasn’t just making tech, he was creating a movement. Apple was a culture, not just a company. And Andy was crucial in shaping that narrative.
When she walked back into his office after yet another firing, she didn’t beg or apologise. She knew exactly what he needed and played that card. “I’ve got what you need,” she said, calm as ever. And Jobs knew it too. He needed her media connections, her press savvy, and her ability to control the narrative.
So, without hesitation, he wrote her a check for $35,000 and rehired her on the spot.
How to Work with a Tough Leader Without Losing Your Mind
Working for a tough boss can feel like running a marathon in flip-flops. Exhausting, frustrating, full of blisters. But it’s doable—if you’re smart about it.
But it’s not impossible—if you’re smart about it.
Here’s Andy’s guide to surviving—and thriving—under tough leadership.
1. Know Your Value—and Make It Impossible to Ignore
Andy didn’t come back after five firings because she liked the abuse.
She knew her worth and made sure Jobs knew it too.
Pro Tip: Know what makes you indispensable and remind your CEO. If you’re the one who drives growth or manages investor relationships, make sure they know it before the next crisis.
2. Frame Your Value Around What Your Boss Needs
Andy didn’t demand her paycheck.
She reminded Jobs he needed her press connections and made herself indispensable by focusing on what mattered to him—his public image.
Pro Tip: Align your work with your CEO’s biggest pain points. If they care about revenue milestones, show how your strategy hits them. If they’re fixated on brand perception, position yourself as the one controlling that narrative.
3. Criticism Isn’t Personal—It’s Fuel
Steve Jobs wasn’t exactly known for gentle feedback.
But Andy turned that harsh criticism into fuel. The more brutal the critique, the sharper she became.
Pro Tip: When your boss gives harsh feedback, don’t crumble. Use it. It’s not personal. Adjust, tweak, and come back stronger.
4. Detach from the Drama
This one’s tough but crucial.
Steve’s criticism was brutal, but Andy didn’t take it personally. She knew it wasn’t about her—it was about the work. By staying detached, she kept her focus on what mattered.
Pro Tip: Don’t take the yelling or negativity personally. Think of it as a video game—every critique is a new level to conquer. The drama is just noise. Stay focused on the mission.
5. Be Resilient—It’s a Leadership Superpower
Jobs fired Andy five times, but she always came back stronger. In startups, resilience isn’t just nice to have—it’s the key to survival.
Pro Tip: Resilience is what separates leaders from the rest. Every setback is a chance to level up. Whether it’s a failed product, a rough quarter, or a personal hurdle, resilience keeps you in the game.
How to Handle Your Own "Steve Jobs"
Your boss probably isn’t Steve Jobs, but tough bosses are everywhere. Whether it’s your CEO, investors, or a high-stakes founder, here’s how to handle them:
Own Your Value
Understand Their Needs
Use Pressure as Fuel
Detach from the Drama
Be Resilient
My Final Thoughts
Andy didn’t just survive Steve Jobs—she killed it. How?
She knew her value, understood his needs, and made herself indispensable.
The same rules apply to you.
Figure out what your boss needs, show them why you’re the answer, and make yourself irreplaceable.
If Andy could handle getting fired by Steve Jobs five times, trust me—you can handle anything your boss throws at you. 💪
The Rabbit Hole - For Those Who Want to Go Deeper
Check out these hand-picked resources:
Havard Business Review: Do You Hate Your Boss?: Half of employees quit because of bad bosses. If your boss makes you miserable, it’s on you to improve the relationship—or leave. Bad bosses aren’t your fault, but staying with them is.
McKinsey: Why so many bad bosses still rise to the top: Overconfident, narcissistic leaders are climbing the ranks. The problem? We mistake confidence for competence, overlooking genuinely capable leaders. It’s time to prioritise emotional intelligence.
Book Recommendation:
Surrounded By Psychopaths: Or, How To Stop Being Exploited By Others
Such a useful and well written article
This post reminds me of the metaphor “pressure makes diamonds”