From a young age, we’re usually told not to ask a lot of questions—don’t interrupt the teacher; hold your comments until the end of the meeting; figure things out on your own. It was only upon deep reflection after turning 30 that I understood the magical power of simply asking. I realized I’ve achieved many of my dreams in life—moving to New York City, having a meaningful career, and finding love—because I haven’t been afraid to be vulnerable and ask for what I wanted.
The good news: Anyone can learn how to do this more frequently and more effectively. If you aren’t afraid to take action, anything is possible. I believe that your life’s path can truly come down to a few defining moments and a handful of important questions. Here are seven questions that I asked that changed the course and quality of my life.
1. “Would you like my phone number?”
I said this to my now-husband. In my 20s, I was living in Sydney, Australia. One night my friend and I were debating whether to go to a concert. We almost didn’t go out, but at the last minute we decided to stop by. I spotted a tall, handsome fellow in the crowd and was pleased when we were pushed together and started chatting. He made me laugh, and he seemed very genuine and warm. Before my friend and I left, I asked him, “Why don’t you take my number?” He did—and he called the next day. We’re celebrating five years of marriage this year.
2. “Can we discuss my salary?”
For my first full-time job, I was a recruitment consultant and saw a lot of salary negotiations. Working in HR, I also understood how replacing a high performer was extremely time-consuming and expensive, so I knew my value as a hard-working, high-output employee. Since then, I’ve negotiated my salary in each new job and each time I had increased responsibility or a good amount of success. As a result, I’ve never complained about my paycheck, and I’ve earned the same as (if not more than) some of my male counterparts. Remember: If you don’t ask, the answer is always no.
3. “May I buy you a coffee?”
When I was 25, I arrived in New York with no connections, no network, and in desperate need of a job. I asked peripheral connections (largely people I met through the LinkedIn introductions I requested) to meet for coffee. Twenty-five lattes and a couple months later, I had two awesome job offers within the online advertising industry and accepted the highest-paying position. This kickstarted my professional network, which has grown exponentially over time. Never underestimate the power of a face-to-face meeting. (And don’t forget: It’s a two-way street. Always connect other people when you can.)
4. “Could I please ask you a favor?”
Many of us are happy to help others, but we’ll never ask for help in return. Don’t deny others the pleasure of giving back to you! Personally, I ask for help with dog-sitting, setting up parties I host, and making connections to new people. As I am a pretty giving friend, people are normally happy to help me out—and it makes my life a whole lot easier. It takes courage to ask and allow other people to help, but one of my favorite observations is the natural cycle of reciprocity that naturally occurs when we allow ourselves to receive.
5. “Can I write for you?”
I wanted to write for the online publications that I love to read, so I took the chance to reach out to the editors and pitch my ideas. As a result, I’m thrilled to have had my work published in various media outlets and have the opportunity to interview well-known figures such as Arianna Huffington, Sara Blakely, and Kris Jenner. My theory is based on this formula that I learned on my sales career: qualified activity X volume = conversion. All that means is if you ask decision-makers often enough and approach them with thoughtful, considered ideas, the results you want will eventually come.
6. “May I have a discount?”
This question has saved me thousands of dollars on items from designer shoes to flights to furniture. It feels like a game to me and I love it (even though it sometimes embarrasses my husband!). Before making the purchase, I simply ask: “Can we work out a deal here?” Often I’ll also offer to pay in cash, buy in bulk, or write a sincere Yelp review if I am happy with the product. Try this at least once or twice—you might even get hooked.
7. “What do I really, really want?”
This is perhaps the most important question of all, and I come back to it frequently. When was the last time you paused and asked yourself what you really want? Maybe you haven’t in a while, or maybe you never have. On an unhurried day, take an interrupted, quiet hour. Close your eyes, breathe deeply for a few minutes until you feel calm, and direct your attention inward. Ask yourself: “What do I want most in this world?”
Remember, you don’t have to go with the flow. You don’t have to satisfy others’ expectations. I had a few course corrects in life (an early divorce, some necessary partying pauses, an unfulfilling yet hard-to-leave-because-it-paid-well corporate career). At those times, I came back to myself when I needed to and allowed my intuition to guide me. Our intuition is rarely wrong. Ask yourself what you want, and the job/relationship/city/fill-in-the-blank will materialize. Then you just have to give yourself permission to pursue it.