I knew I only had a few seconds to decide: either ask a question that might make me look out of place — or worse — or just stay quiet and walk away from a rare opportunity. My heart was racing. I didn’t want to derail the Q&A or take time away from other students, but something told me I had to speak up.
So, I asked, kind of casually, “Do you think Howard Marks could sign my book?” The speaker paused for a moment, clearly a little surprised. I don’t think anyone in the room was expecting that, and honestly, neither was he.
For those who don’t know, Howard Marks is the co-founder of Oaktree Capital Management and a highly respected investor known for his insightful memos on market cycles and risk. He helped pioneer investing in high-yield (junk) bonds and distressed debt, and today Oaktree manages over $170 billion in assets.
I didn’t look around much, but I caught someone near me quietly say, “That’s crazy,” and a few people seemed confused, unsure if I was being serious. For a second, I started to feel a little embarrassed, like maybe I’d just asked something out of place.
But then the speaker nodded and said, “Yeah absolutely, that wouldn’t be a problem at all. Howard loves signing books.”
That response changed everything. I was instantly excited—not just because I was going to get a signed copy of Mastering the Market Cycle by its revered author, but because the small risk I took actually worked. It reminded me that sometimes, the payoff is waiting on the other side of a simple question.
That moment reinforced something to me: we naturally overestimate the downside of asking and underestimate the upside of putting ourselves “out there”.
There’s this idea that asking a question, but especially one that feels personal or outside the usual script, might come off as awkward or unprofessional. I get it. I used to be someone who avoided asking anything unless I was sure it sounded smart or on topic. I was nervous about sounding dumb or being judged. But over time, I realized that most of those fears are exaggerated. If you can push through that hesitation, even briefly, you put yourself in a spot most people avoid.
Everyone’s heard the phrase, “The worst they can say is no.” But very few people actually believe it. In reality, the worst thing that usually happens is a few seconds of discomfort. Someone might say no. The moment might feel awkward. But people move on, and they forget about it almost immediately. On the other hand, if they say yes, it can lead to a conversation, an opportunity, or a memory that sticks with you.
Whether it’s a signed book, a meaningful connection, or just a moment that builds confidence, asking makes things happen. And if you're willing to be the one who speaks up, you start to separate yourself from the crowd.
If there’s one thing I hope other students take from this, it’s this: just ask!
Ask the question. Ask for advice. Ask for the thing you’re excited about, even if it feels a little uncomfortable.
And if you’re someone who still gets nervous—like I used to—try this: give yourself a countdown. In your head, say "three, two, one," and then just ask. Don’t give yourself too much time to overthink it. The longer you sit on a question, the easier it is to convince yourself not to ask. But once you get a few reps in, it becomes second nature. I don’t even think twice about it anymore.
It might still make your heart race at first. You might feel the adrenaline kick in. But if you can push past that for a few seconds, you’ll find that most of the time, asking pays off.
So next time you're sitting in a classroom, a company visit, or a conversation with someone you look up to, and you find yourself hesitating—try flipping the question. Don’t ask yourself, "What if this is embarrassing?" Ask yourself, "What if they say yes?"
You might be surprised by what you receive.
