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CS#329: why A-plus students can have F-grade careers (+ more)

About Rohan

Hey, I’m Rohan!

I write thoughts about life and career strategy a few times a month.

I run Coached, the behavioral science lab, and Resume Worded, the best software for job seekers.

A good place to start is our free 3‑minute, science-backed personality test.

We spend years learning how to succeed in school. And surprisingly, many of those patterns stick with us decades into our careers. In today's Mentor's Corner, I'm breaking down 6 key lessons about what really drives success at work - and which common misconceptions might be holding you back.

Quick ask: I spend a big chunk of my week writing these emails, but keep them free. In return, I just want you to spread the word. Two ways:

  • Know someone who’s on a job search? Tell them to check out Resume Worded. They can get a free resume review here. It’ll turn their resume into one that actually works.

  • Forward this email to a friend or family member if you think they’d get value from it.

Estimated read time: 5 minutes 10 seconds

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Insights put together by me. One practical lesson a week that will make a measurable impact on your career, delivered right to you — for $0.

Why school success ≠ career success (and 6 key career lessons)

We have some massive misconceptions about what drives career success.

Most of them? They come from what we learned in school.

And here's the thing:

These "lessons" aren't just unhelpful - they're actively holding us back.

(Want proof? When psychologist Lewis Terman tracked 1,400 "genius" students' careers, most ended up pretty average. Meanwhile, two students he rejected for "low IQs" went on to win Nobel prizes.)

Because the fact of the matter is…

School success doesn’t equal career success.

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So today, I want to share 6 career-killing lessons we learned in school that we should unlearn if we want to have stellar careers.

Number one:

❌ “Mistakes, bad!”

You put a bunch of wrong answers in a maths test, and it gets handed back to you with an, “F”. 

What school tells us:

“Mistakes are bad.”

The reality:

Mistakes are the only way you learn (and reach success)! Often, mistakes aren’t only not to be avoided, but must be actively sought to make progress.

Part of why we get so crushed when we mess up at work? It's because "failure = bad" has been drilled into us since we were kids.

Here's what you need to internalize instead: Every failure is a data point. Every setback is growth. The faster you fail, the faster you learn.

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…if you get value from this, tell people about Coached so they can get free career coaching too! I put a ton of time into my essays and it’s super fulfilling to see them reach as many people as possible.

Btw, if you want to share this essay with a friend, or colleague, here’s a link to it:
coached.com/essays/school-vs-careers-and-real-life/- thanks!

     

And on a related note…

😵 Struggle is actually GOOD

Here's something wild: Often, it's the "perfect" students who struggle most in their professional careers.

Why?

Because they've often never failed. Never faced rejection. Never had to pick themselves up after a real setback.

They've mastered getting A's. But they've never learned how to bounce back from F's. And that’s probably the #1 career skill.

Even NVIDIA's CEO tells Stanford students he wishes them "pain and suffering" - because that's what builds the resilience you need in the real world.

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The takeaway? Struggling = building the resilience that school never taught you.

🤓 Mr. Know-it-all ain’t Mr. Win-it-all

When Henry Ford was called "ignorant" in a newspaper, he sued. In court, lawyers tried proving it by firing trivia questions at him.

Ford's response? "If I need to know something, I press a button and get an expert to tell me. Why clutter my mind with things that don't matter to my business?"

See, school taught us expertise means knowing all the answers.

But in your career? Expertise is knowing which questions to ask, and who to ask them to.

Because career success isn’t a general knowledge quiz. Far more important are vision, original thinking and the ability to ask great questions.

The key takeaway for you: Get better at asking the right questions. This is also probably the #1 skill to get better at with AI too - AI (like a ChatGPT) is only as good as the prompts or questions you give it.

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↔ The opposite of a good idea might be a good idea

In school, there’s usually one right answer to a question. But in life, there is no single "right" answer.

In fact, sometimes complete opposites can work brilliantly:

Some leaders succeed by being hands-on with their team. Others win by stepping back completely.

Some products thrive on premium pricing. Others dominate by being the cheapest option.

A fun example:

Take Avis, the car rental company. Every company claims to be #1 in their ads. But Avis? They took the opposite approach: "We're #2. We try harder."

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It’s one of the best performing marketing campaigns of that era.

The key takeaway: As you progress in your career, remember this - “the opposite of a good idea can also be a good idea” (shout out to legendary marketing exec Rory Sutherland for that quote). There's rarely one "right" way (and don’t listen to people who say their way is the only way).

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⏳ Don’t play the ‘short game’

In school, everything's short-term. You study for an exam, take it, get your grade in a week. Do a 6-month coursework, get your results at year-end.

But in life?

The most valuable work often takes years to bear fruit - with little feedback along the way.

Like when:

  • A mentor you've known for years puts your name forward for a leadership role

  • An old client brings you in to lead a high-profile project

  • Your reputation lands you a coveted speaking slot at an industry conference

  • Someone you helped five years ago becomes CEO and remembers your kindness

School trains you to expect quick results. But the biggest career wins? They come from playing the long game.

The key takeaway: Stop expecting quick wins like school trained you for. The best career moves are often invisible for years before they pay off.

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Btw:

LinkedIn's important for playing the long game too. You stay connected with thousands of people over the years who’ll remember you. I can't tell you how many old colleagues or contacts have reached out saying they saw something I posted. It helps you in staying visible and making sure you're top of mind.

Just make sure your profile's optimized so you maintain a good impression — and YOU control what people remember you for. Use this tool to start with. (It’s Resume Worded’s tool — and is by far the best thing out there for optimizing LinkedIn profiles). And it takes 30 seconds.

 

📋 "Follow the rules!"

In school, you win by following instructions. Remember that kid in class who always colored inside the lines? Who never deviated from the textbook answer? They probably got straight A's.

But in your career? The biggest breakthroughs often come from questioning "how things are done."

Maybe it's finding a better way to run team meetings. Or discovering a more efficient approach to project planning. Or developing a new way to handle client relationships.

The point isn't to break rules for the sake of it. It's about recognizing when the old way isn't the best way.

The key takeaway: Sometimes the best solution comes from ignoring "how things are done" and asking "how could things be done?"

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If you enjoyed this essay, all I’d like in return is one small favor.

(I don’t ask you for a lot….rather, these emails are expensive to send out, yet I keep them free and don’t paywall the best parts). Just do any of these - it really helps!

1. Know someone on a job search? Tell them about Resume Worded.

It’ll make their job search a lot shorter. They can get a free resume review at resumeworded.com/free-resume-review

2. Got a smart friend who LOVES getting better? Tell them about Coached.

I love seeing them reach people who want more out of their careers. If you want to share this essay with a friend, or colleague, here’s a link to it: coached.com/essays/school-vs-careers-and-real-life/ - I promise to keep the quality of my emails high so they love you for it.

3. Leave a quick review for Coached.

You get ideas that change your career for the better. In return, a short 30-second review would make me feel good about spending the time to write this. I think it’s a fair trade. Do it here.

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Related note: this AI tool makes writing cover letters super easy - try it. Makes the job search less sufferable.

Try it just once for a job you actually want — see how good it is for yourself.

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One actionable piece of advice to help you hack your job search.

Your resume sounds like ChatGPT wrote it (and that's messing up your chances)

More people are using AI to write their resumes. But there’s a problem: most AI tools are making resumes WORSE.

Let me show you what happens when you use ChatGPT, or other generic resume tools:

     

Your original version:
→ Managed social media accounts
→ Designed email templates for the team

❌ If you ask ChatGPT to rewrite that, it’ll give you:
→ Leveraged strategic social media initiatives to enhance brand visibility and engagement through data-driven content optimization
→ Spearheaded innovative email solutions to drive cross-functional collaboration and optimize communication efficiency

     

That might look ‘smart’ on the surface. But in hiring manager land, this is what we call buzzword soup. Hiring managers spot this AI-generated garbage instantly - and they skip right past it. It’s a big tell.

Why does ChatGPT write like this? It learns from resume advice on the internet, and most of that advice is terrible.

The truth is, AI can work for resumes. But you need to make sure you’re using tools built specifically for this, trained on what hiring managers want to see. For example, if you used our Resume Rewriter tools, you’d get lines like this:

     

✅ Grew company Instagram from 800 to 3,200 followers in 4 months by posting 3x weekly and engaging with industry accounts
✅ Designed email toolkit with 8 templates and style guide enabling 3 teams to build mobile-responsive emails; saved roughly 5 hours per week

     

Hiring managers LOVE stuff like this. You can literally drop these into your resume and know you’ll get a higher response rate every time you apply.

If you’re working on your resume, I’d recommend uploading your resume here. It’ll rewrite everything on your resume in a few seconds, and make sure they don’t sound like AI.

Stop applying to jobs with a bad resume!

Optimize it once for free.

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Until next time,

Rohan
Founder at Coached & Resume Worded

Illustration of Rohan Mahtani
Written by Rohan Mahtani

I also send these out by email.

This is Coached Weekly, my career notes where I share the tiny % of ideas that actually work in real careers. It takes 5 minutes to read, but could speed up your career by years. I write this myself (no AI). —Rohan Mahtani (LinkedIn)

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