Letter 6: Difficult Experiences Are the Real Highlights of Your Resume
Nothing great was every achieved without doing anything difficult...
If I asked you to list the highlights of your career, you’d probably think of titles, awards, or successful projects. But here’s the uncomfortable truth: those aren’t the real highlights. They’re the polished version we put on LinkedIn. The real highlights — the ones that shaped you, tested you, and actually made you valuable — are the difficult experiences.
Today, I want to flip how we think about our careers. Because the story of our growth is not written in our victories. It’s written in our scars.
Shift 1: Projects That Fail Teach You More Than Those That Succeed
Success is a terrible teacher. When things go smoothly, we don’t stop to ask why. But failure forces us to notice every detail.
Think about the time you worked hard on a project, only to see it collapse. At first, it feels like waste. But here’s the twist: that failed project probably taught you more about problem-solving, about communication, about resilience than any of the successful ones.
Takeaway: As cliche as it may sound, ‘Your successes build your confidence. Your failures build your competence.’
Shift 2 – Leaders Respect Resilience Stories More Than Perfect Stories
When you’re in an interview or speaking to a leader, they’re not scanning for a perfect resume. They’re scanning for proof that you can survive reality.
Anyone can deliver when the path is smooth. But the people who stand out are those who stayed steady when the lights went out, when resources vanished, when the plan collapsed.
Takeaway: Resilience is a more valuable skill than perfection.
Shift 3 – Painful Moments Build the Muscle of Adaptability
Think about the hardest day of your career so far. Maybe you were humiliated in front of your team. Maybe you were overwhelmed and missed a deadline. Maybe you were given a task you had no idea how to handle.
In the moment, it feels like a breakdown. But in hindsight, you’ll notice something: each of those moments built a hidden muscle — adaptability. You learned how to adjust, how to improvise, how to survive the storm. And adaptability is the single most valuable skill in a world where change is the only constant.
Takeaway: Every painful experience is a training ground for the career you don’t yet see coming.
So the next time you look at your resume, remember: the lines on paper don’t tell the full story. The real highlights are invisible. They live in the challenges you survived, the failures you learned from, the setbacks that forced you to grow.
Your career is not just a list of positions held. It’s a record of battles fought. And often, it’s the scars — not the medals — that prove your worth.
In the next episode, we’ll go deeper into the one advantage most people accidentally lose early in their careers: the ability to be themselves. And why the more you try to fit in, the less you stand out.
If today’s episode gave you a new way to see your own journey, write it down. Because scars fade from memory — but lessons don’t, if you capture them.
And when those difficult experiences arrive, the one thing you’ll be tempted to lose is yourself. In the next episode, we’ll talk about why your biggest advantage — being yourself — is the one you must never let slip.