Day 174 – Sometimes You Have to Ask

One of the hardest lessons I’ve learned in life is that sometimes, to get what you want, you have to ask. Rarely does someone just show up and randomly offer you a boon. More often, you need to ask for it—and only then will the other person consider whether they’re willing to grant it. This is a powerful lesson, and one I believe should be taught to children early in their development.

Unfortunately, I was raised—and consequently, I raised my children—with the mindset of “fake it until you make it.” Meaning: never let anyone see your weakness, never let on that you don’t know something. Instead, figure it out on your own and be extra prepared for everything you do. Now, this isn’t all bad. Kids raised with this mentality tend to be self-starters, highly motivated, and usually carry a strong sense of confidence—or at least a deep belief that they can figure anything out.

But this belief that you can figure everything out shouldn’t replace the idea that you should be humble enough to ask for help. I’ve missed countless opportunities for learning, growth, and improving my circumstances—simply because I didn’t ask. I didn’t want anyone to know I needed help. I wanted to be perceived as the best at everything. Little did I know, I was playing the part of the fool—and everyone around me knew it, while I remained blind to my own comedy.

Taking this idea a little further: my first two kids would fill out their “letters to Santa” sheepishly. They’d timidly ask for what they really wanted, and then add a few small things. Occasionally, they’d include a request for someone else—maybe trying to show empathy, or maybe strategically thinking, “If I act like I care for others, Santa might give me more.” Honestly, I can’t blame them. I do the same thing in my prayers. One of many character flaws I still need to work on.

But then came our third child.

She had no such hesitation. She took her Christmas list seriously—like a business proposal. She researched, did a cost-benefit analysis, and elevated her requests. She didn’t just ask for makeup—she asked for a refrigerator to keep the makeup in. She wanted inventory, so she could launch a business. She included stationery and other potential marketing materials. She was asking for seed money, basically.

I remember asking her about her list, which by then had grown to six or seven pages. “Do you really think you’re going to get all that?” Her response: “Can’t hurt to ask.”

That response sums up the difference between those who make great gains and those who struggle. I would never have thought to ask for the world—much less prioritize my list to help the potential “buyer” (Santa does have a purchasing team, right?). I would have thought long and hard about my request, but I wouldn’t want to reveal too much of myself. So, I’d ask for something simple—like a bike to get to school or a few new clothes.

Not my daughter. She asked for the world and waited to see what shook loose.

Now let’s take this idea even higher. What if there is a God—and what if that God will grant some boons only if you ask for them?

Just so you don’t have to: I already asked for a Rolls-Royce La Rose Noire Droptail in the Black Baccara Rose color. I still have a Ford Expedition in the driveway, so I guess that one didn’t qualify. But what if there are certain gifts that would align with God’s design, fulfill your deepest desires, and they’re just sitting there—waiting for you to ask?

That’s a thought worth pondering.

This is a mentality, I think. A way of approaching your path in the world that’s quite foreign to me. Instead of walking through life with imposter syndrome, maybe we ought to move forward with humility and curiosity. That way, we stay open—available for advice, mentorship, gifts, and even manna from heaven… or whatever divine boon you’re pursuing.

Because maybe—just maybe—it can’t hurt to ask.

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