What's Holding You Back? Here's How to Turn Your Biggest Obstacle Into An Asset

You want to take a risk. But you're thinking about everything that stands in your way.

We all do this. I do it plenty, believe me. And this anxiety often takes the same form. You think: Other people have an advantage that I don't have.

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What do they have? Maybe they have more connections than you. Or resources. Or experience. They know things you don't. They've seen what you haven't. How can you compete against that?

Recently, I was discussing this with the billionaire serial entrepreneur Naveen Jain, and he said something that totally reframed how I think about these obstacles.

I'll share that with you — and help you turn your obstacle into an asset.

First, the billion-dollar reframe.

Naveen Jain was born into poverty in India, moved to America in his 20s, and became an entrepreneur. His first company, InfoSpace, was a global tech leader in the 90s. He's founded or led many more since, including a space company and now a groundbreaking medical testing company called Viome .

But here's another fact about Naveen: He speaks with a thick Indian accent.

That could hold him back. He's clearly thought a lot about it, operating in an ecosystem of American-born leaders. Can people understand him as clearly? Will they take him as seriously?

But here's what he told me about it, in an interview for Entrepreneur :

Your belief system is the biggest barrier to anything you do. Let's say my belief system is: "Look at all these great entrepreneurs — they're so fluent, they speak perfect English. But Naveen, you're an immigrant. You don't speak like them, you don't look like them. You will never be an entrepreneur."

Or, I could think to myself: "Wait a second. When someone fluent like Jason speaks to me, I can be multitasking and still make sense of what he's saying. When Naveen is talking, if I don't give him 100% of my attention, I have no idea what he's saying."

Guess what? That is my asset! When I speak, I get 100% of your attention. So being different to me is not disadvantageous. Being different is your asset. That's my belief system.

To me, here's the most powerful part of what he's thinking: He accepts the reality of his situation — yes, his accent can be a barrier — and then chooses to see an upside to it. He isn't hiding it. He isn't trying to compensate for it. He's just using it.

When you reframe your disadvantage, you aren't magically changing reality. But you are giving yourself permission to operate differently. Naveen can now speak with more purpose. He can confidently hold others' attention. He has created value where previously there was none.

Now let's expand beyond work

What is it like to be an outsider, at a critical moment in life, and surrounded by people who don't understand you?

That's what my wife Jen set out to learn. She spent a year following first-generation college students through their freshman year, and her new book about their journey, Rising Class , just came out. (It's perfect for the student or parent in your life! Grab a copy! )

The students she shadowed were constantly weighing themselves against their peers, who had more money and advantages. This led to a lot of self-doubt, which they had to manage.

Towards the end of the book, there's a lovely scene where Briani, one of the book's main characters, is helping a high school senior named Jamal apply to colleges. Jamal, like Briani, comes from a low-income family. And he wonders: How can he compete with other students, who have padded resumes and expensive tutors?

Here's from the book :

Briani remembered writing her own college essay. She'd written about the family tradition of eating Costco pizza on weekly Sunday shopping trips. With her parents' work schedules, it was the only time they were all together. The pizza came to symbolize their efforts — not just to provide for Briani and her brother Joseph but to give them the privilege of happiness. The pizza symbolized both their sacrifice and their love.

And yet Briani feared that admissions officers wouldn't understand. How could the people reading applications about all-state champions and award-winning teen scholars understand the significance of a slice of Costco pizza?

But her truth was her truth.

"You have to trust the process and trust yourself," she told Jamal. "This is your story. You don't have to prove yourself."

Ultimately, Jamal wrote an honest essay based on his life and was accepted into his first-choice college. "He wrote from his heart," Briani said in the book. "That's something other kids can't replicate."

And that right there? It's the same recognition that Naveen had — that an obstacle is an asset. Briani and Jamal shared stories that most students couldn't. Sure, others had extra-curriculars. They had heart .

How you can do this yourself

At the beginning, I described our mental blockage this way: Other people have an advantage that I don't have.

Now here's a starting point for fixing that. Ask yourself the opposite:

What do I have, that other people don't?

Whatever the answer, that's your starting point. The next question is: What is that good for?

In retrospect, I did a version of this early in my career. My first national magazine job was at Men's Health , and, among other things, I was tasked with editing a column called "15 Minute Workout."

Now, let's be honest. Look at me back then, in a gym with NFL legend Shannon Sharpe:

Do I look like I know anything about 15-minute workouts? No. I don't know anything about workouts . (Or style, apparently. What am I wearing???) And this made me very nervous.

The "15 Minute Workout" column was written by Adam Bornstein , who was the magazine's fitness editor at the time. He'd write descriptions of exercises that I could not follow, and I kept thinking: I don't understand this. I am useless.

But then I realized something important: If I couldn't understand it, then readers might not understand it either. And why were these descriptions hard to understand? It's because Adam is an expert! He knows his stuff — and he knows it so deeply that he was overlooking what novices don't know .

This gave me purpose. My job was to take Adam's expertise, and then make it accessible to a straight-up dummy like me. My fresh eyes had value. I saw what the expert didn't.

At first I worried that this would annoy Adam. But no. The opposite. Adam appreciated this perspective — because his goal was to be helpful to all readers, regardless of their experience level. He wanted someone like me to check his blind spots. And so began a fantastic working relationship — and, today, many years later, an enduring friendship where we continue to help each other.

Right now, you have something like this. You're sitting on an asset. A very valuable one. It starts by recognizing it. And then using it with confidence.