As resourceful, driven, and smart as I am, I’m equally stubborn (blame it on astrology; I’m a Taurus!). And though my doggedness has paid dividends in some areas, it’s burned me in others—most specifically when it comes to seeking and asking for help.

Over the years, I got so good at making excuses for people without their permission. Oh, she’s too busy to help me, I’d assume. He won’t think enough of my project to accept my meeting request, I’d reckon. These were mechanisms I fell back on to talk me out of the ask. But they weren’t missing out, I was. It was my potential that was untapped, my dreams unrealized, my desires unmet.

So once I got fed up with feeling stuck, I realized that while the worst someone can say is no, all it often takes is just one yes to get the ball rolling. That’s where I found my freedom.

If you can relate, here’s the good news: No matter the area in your life—career, relationships, style, wellness, finance—the key to unlocking the door to your more powerful self rests in your capacity to ask for what you need.

Click through for five crippling reasons you’re afraid to ask for help, plus the strategies to help you master the art of the ask.


Think about the last time someone who cared about you asked, “How are you?” or “Is there anything I can do for you?” Chances are before you could even think about it, you replied, “I’m fine.” But the difference between fine and exceptional can often be found in your willingness to request and accept support.

Sure, we’ve been conditioned to believe that there’s strength how much we can accomplish on our own, but as I mentioned last week: Independence is an illusion. There’s no shame in sourcing help from people who care about you. And here’s why: When you’re at or as close to 100 percent as possible, your tribe knows you can give it in return.


From Shonda Rhimes and Beyoncé to Hillary Clinton and Anna Wintour, the most successful women not only are comfortable requesting help, but they’re clear that they’re deserving of it. Each of these four women share something in common: They’re all up to monumental feats in their industry.

And while you may not have the platform they share, you’re likely up to some difference-making deeds yourself. But when you reject your worthiness, you’re cheating the universe. Why wouldn’t you maximize your gift’s potential by petitioning people to invest in it? Plus, when women who admire you see you’re unafraid to ask for what you want, it inspires them to do the same.


When I was an assistant at Lucky, I wanted to learn how the editors put together their sections each month. I knew eventually I was interested in not only editing my own section one day, but also running this site more efficiently. Additionally, I noticed that our editors were never not busy, so to be taken seriously, I needed to be clear on my ask.

I reached out to Jayna Maleri—then Lucky’s fashion features editor, now editorial director at Madewell—and asked: How do you put your section together each month? Not only did she respond with some invaluable advice, she invited me to her office to see her inspiration boards and answer my questions. And after I became a full-time editor, I was able to apply what I absorbed from Jayna to my stories—and ultimately The Stylish Standout.

Once you realize you’re worthy of support and release the fear of judgment, you can focus on what you actually need help with in the first place. And here’s a secret: People love to help those who are clear on what they want.


While you should have the confidence to ask for what you want, it comes with a stipulation: gratefulness. Whether it’s money, mentorship, a connection, or a glowing recommendation, the reality is you’re still asking for something. So don’t take your network’s kindness for granted because the most benevolent people often have the longest memories. And word of churlish behavior tends to travel fast.

Another thing: Even if you don’t get what you’ve asked for, express appreciation to them for even considering the request to begin with. The world is small and industry circles are even smaller—you never know when you’ll come full circle and have an opportunity to make another ask in the future.


There’s something someone needs that only you have. And the premise of The Stylish Standout is for you to share what makes you stand out with the world. That’s where the concept of lifting as you climb comes in. The next time a friend, colleague, or loved one thinks enough of you to honor your ask, look to do the same for a coworker, mentee or, better yet, a stranger. There’s enough of everything for everyone to have their share—the fact that people have been able to comfortably pour into you on your journey is proof—so don’t be caught up in your own world that you miss the chance to be someone else’s yes.

You get enough trash. Make room for some treasures

I send emails worth opening every time. Because Stylish Standouts deserve better than stale newsletters.

My notes include tips and tricks to take your brand and business up a notch. Plus, they’re a peaceful escape from your frantic social media feed (and that looming deadline).