It was just another rainy Saturday afternoon in October of 2000 when I showed up at the Landmark Education office in San Francisco to visit a friend—but it turned out to be a day that would change my life forever. This was the day I met Michelle.
Landmark Education is an organization that delivers personal development seminars around the world. I’d been taking various courses and volunteering for them for the previous two years. When I walked into the office that day, Michelle happened to be volunteering. Although I came in to visit a friend of mine who worked there, I was much more interested in talking to Michelle once I met her. She was great—full of energy, passion, and enthusiasm, and she was adorable.
We chatted for a bit and I found out she was involved in Landmark’s seven-month-long leadership training program, which I’d participated in the previous year. It sounded like she was enjoying the program but also finding it challenging (which had been my experience as well). It’s pretty intense—both in terms of the time commitment and the personal growth involved. We sometimes referred to it as “transformational boot camp.” Michelle and I shared a few stories about the program and a few laughs. I really wanted to ask her for her phone number or, more specifically, to ask her out. However, I was feeling a bit shy and insecure—I woke up feeling funky that morning and I didn’t actually have a job at the time. I’d been laid off a few months earlier from the start-up where I was working (as were many of us 20-something, dot-commers) and had not yet found another job or gotten my speaking/coaching business started. Because of these things, I wasn’t feeling abundantly confident about myself in that moment.
I spent the afternoon catching up with my friend and talking with Michelle whenever possible. I couldn’t quite tell if she was flirting with me or just being friendly, and I didn’t know what her relationship status was or if she had any interest in hanging out with me. The best (well, safest) idea I could come up with was to offer her some help with her homework from the leadership program.
As I was about to leave, I wrote down my contact information on a piece of paper (I didn’t even have a business card at the time). I walked over to Michelle, handed her the paper, and said, “Here’s my info. Feel free to get in touch with me if you need help with your homework.” I was trying to make it seem like no big deal (although it was a big deal to me) and also trying to come across as confident (even though I didn’t feel that way). She took the piece of paper, and simply said, “Thanks.” Then, she reached into her purse and got out her business card holder. She said, “Here’s my card,” smiled, and handed it to me. I was fired up!
I left and figured I’d wait for a few days to call her, so I wouldn’t seem too needy or pushy. The following Monday morning, I got up and went for a run. When I came back to my apartment, there was a message on my phone. It said, “Hey, Mike, this is Michelle. It was nice to meet you on Saturday. I wanted to see if you really meant what you said about helping me with my homework. I could use some help. Call me back and let me know.”
I was excited that she’d called, and after hearing her message, I thought, I really like this woman—she’s confident, straightforward, and funny. However, I also felt a little nervous because, while I was happy to help her with her homework, that wasn’t really why I gave her my contact info. The truth was I wanted to ask her out, but I felt scared. What should I do? I thought. I contemplated it for about 20 or 30 minutes, and then said to myself, “You know what? I’m just going to tell the truth.”
I picked up the phone to dial Michelle’s number, with my heart racing and my hands shaking. When she answered, my heart raced even faster. I said in a pretend confident tone, “Michelle, hey there, it’s Mike. Thanks for your message. Glad we met on Saturday. Listen, I’d be happy to help you with your homework, but to be honest, I was really just trying to find a way for us to exchange info so I could ask you out on a date.”
There was a long pause on the other end of the phone. I held my breath. Then Michelle said with a laugh, “Oh good, I’d rather go out on a date anyway!” We went on our very first date the next week. And now, more than 13 years later, I’m glad I had the courage to simply tell the truth and ask for what I wanted—I’m also very happy that she wanted to go out with me! In hindsight, it would have been a lot easier if I had just asked her out when we met. It would have saved me a lot of unnecessary worry.
Unfortunately, we often tend to get in our own way, psych ourselves out, and allow our egos to run the show when it comes to asking for what we want. Whether it’s in business or our personal relationships, we waste a lot of time trying to figure out the right way, the right time, and the right words to use in order to get what we want—instead of just authentically asking for it. Sadly, there are times when we simply don’t ask due to our fear of rejection, disappointment, or embarrassment. While this is very common and we want to have compassion for ourselves in this process, all too often we give away our power to our fears.
My first job after my baseball career ended was in sales. I worked for an Internet company that represented hundreds of websites and sold advertising space on their behalf. The first week of my job, I had a meeting in my manager Steven’s office. He had Scott, one of the executives from the New York office (where our company was headquartered), on the phone. Steven introduced me to Scott and asked Scott if he had any words of wisdom for me as a young guy just starting out in sales.
Scott asked, “Hey, Mike, how do you feel about hearing no?”
I wasn’t sure how to answer the question, and could tell it was some kind of test. I said, somewhat timidly, “Ah, well, I don’t really like it very much.”
Scott said, “Well, it would be good to get over that! When someone says no to you, Mike, you should thank them.” He continued, “First of all, because the more often you hear no the less scared of hearing it you’ll become. And, second of all, every no gets you closer to a yes.”
I appreciated Scott’s wisdom, which not only helped me in my sales job, but is something I still think about today when I find myself scared to ask for what I want in business, my relationships, and life.
The more freedom and confidence we have to ask for what we want, without being pushy, demanding, or overly attached to the outcome, the more likely we are to get what we want. Can it be scary? Yes. Will we get disappointed sometimes? Of course. Might we feel rejected or embarrassed from time to time? Yep. However, it’s important to remember with both empathy and courage that, as one of my favorite sayings reminds us, “The answer’s always no if you don’t ask.”