

Growing up, I would often find myself asking my dad for advice.
“Should I ask?”
“Should I try?”
“What if they say no?”
And one thing I always heard him say was, “La peor diligencia es la que no se hace.” This is the Spanish equivalent of “You miss 100% of the shots you don’t take,” “You have to play to win,” or “Nothing ventured, nothing gained.”
Over time, I started to default to this phrase when making decisions. I reframed my mind from thinking
“What if they say no?” to "What if they say yes?"
“What if I fail?” to "What if I don't even try?"
The thrill of shooting my shot and succeeding became greater than the fear of failure, the fear of rejection, and the fear of vulnerability.
What I learned from both of my parents was to be more bold in asking for what I wanted. They taught me that “the squeaky wheel gets the grease,” and reinforced ideas like “ask and you shall receive.”
One skill I struggled to learn was that of negotiation. “Ask for more,” they would say. “You’re worth it. You deserve it.” But negotiation felt intimidating, uncomfortable, and awkward. And as with anything, confidence came from practice.
Low and behold, when I finally worked up the courage to negotiate my salary, I was met with success. Success in negotiation doesn’t always mean getting everything you ask for. It means getting yourself into a better position than you were had you accepted the initial terms. That delta space, that difference, is what motivates me to negotiate today.
One major lesson I had to learn was to operate despite discomfort. Discomfort could not be an excuse for inaction. I learned that I could put up with a few minutes of discomfort if it meant I could increase my income by several thousand dollars. After all, how often do I get to make that kind of money in a matter of minutes? Additionally, negotiating your salary provides a yearly return, depending on how long you stay at that position. No way I’m passing up those opportunities.
I learned that there’s no shame in negotiating. In fact, it’s expected. So, why should I miss out? The potential reward, gain, and opportunity is so much greater than the fear of discomfort.
I was recently buying a new car, and I was at the dealership with my dad. At this point, my dad has negotiated a dozen or so cars over the years, so he is very comfortable with the process. This was my first time, though.
After some time negotiating, I could sense we were reaching a stopping point. You’ll start hearing cues, like “that’s the best we can do,” “that’s the lowest we can go,” and “that’s really the best offer we have.”
I wanted to make sure the car had heated seats, since that was one thing I wanted from the beginning. And the representative told us no. So, my dad asked if they could throw them in so we could close the deal, but they said they couldn’t because they were already giving us the very best they could. My dad asked how much they were, and they told us $500. We had just negotiated another $250 off the price, so I asked if they could take off that last discount and give us the heated seats instead.
My dad gave me a look of approval and turned to the representative. The representative paused for a minute and told me he could make that work. “Because YOU asked,” he told me.
As I mentioned, this was my first time in the negotiation process for a car. It was a new and interesting experience. And, I of course felt more comfortable knowing I had an experienced ally with me. When it came to the heated seats, it was more of an experiment for me. It was lower stakes because it wasn’t something that would make or break the deal. If I could get them for free, awesome. If I had to pay for them, it wasn’t a big deal in the grand scheme of things.
So, really, for me, the win was more in the learning and in trying something new for the first time. It’s important to detach the outcome from the effort. Though it may seem counterintuitive, to build confidence with negotiation, asking the question is more important than getting what you asked for (which will not always happen). The worst thing that could happen by asking my question is that they would say “no.” That frees me up from staying in a place of fear of rejection, and just allow myself to ask the question and see what happens.
When I see people who are really nervous, all that tells me is that they lack confidence. Not necessarily in themselves, but a lack of confidence in the skill of negotiation, in the skill of asking, and in the skill of vulnerability. Key word being skill, meaning it’s something you can improve and develop with practice.
One indirect way to begin building the muscle of asking is to shoot your shot on things that require little to no discomfort and cost you nothing. For example, entering sweepstakes. I’m not someone who listens to the radio too often, and yet I’ve won concert tickets from three different radio stations. Because you miss 100% of the shots you don’t take. Just get in the game – and consider how little you have to lose.
Ultimately, if you’re not willing to face some discomfort and do things differently, you’re not going to grow. You’re going to remain in your comfort zone rather than a state of growth and improvement.
What you don’t want to do is recirculate limiting beliefs, like “that’s just not who I am,” or “I’m not comfortable with that,” or “I could never do that,” because that will lead you to reinforce those beliefs about yourself and will just be another thing you have to unlearn.
In short, by simply having the courage to ask a question, you increase the likelihood of getting what it is you want – whether it’s a raise at work, a discount on a car, or a better deal on a home.
You won’t know if you don’t ask.