Lessons Learnt Asking Strangers for Money

Foreword - This is a weekly blog about breaking through the limitations of being young and inspiring those who strive to live life on their own terms.

Many times a year we would be tasked to hold a can outside the door of a local mall or grocery store and solicit strangers for donations. “Follow my lead” my sergeant would say, “Hi sir, would you like to support the army cadet program?” she would ask. Some would attempt to rummage their pockets for spare change, but more often or not the potential donor would instead quickly scurry away. Not the most encouraging example for a 12-year-old on his first shift.

Losing at the Starting Line

Illusion of being in the race

The first ask, was always the hardest. You would take a deep breath, but the words always seem to get stuck in your throat. “The next one for sure” you would think to yourself, but again, nothing. What’s interesting however, as more and more people walked right by, was how my brain would automatically try to justify this inaction.

• How am I supposed to ask if they are looking away?
• He’s walking way too fast and definitely won’t have time to stop
• She doesn’t look like “the type” who would donate (whatever that meant)

Notice how these questions and reasons all came before I even attempted the ask. The game hasn't even started and I've already set myself up to fail. But the crazier thing however was that it didn't feel that way. Aside from a completely empty can, I felt fine. I've rejected myself with a reason that I made up, one that not only would make myself feel better but one where I was never in the wrong.

It's always them and not me, a primal "flight" mechanism that fires off in the face of danger and uncertainty. A mindset all too familiar that still recurs even to this day when I venture outside of my comfort zone.

The Magic Question

Asking without actually asking

After what seemed like a life time of awkwardly smiling at strangers while holding my can out, I came to the realization that it wasn't going to look great going back to my officers with an empty can. Genius.

But what am I going to do? Asking was most definitely out of the question. So I took the easier route out. Pretend like I was trying by asking something else, something natural.

"How are you doing today ma'am?" I manage to blurt out to a lovely old lady walking into the store. She smiled at me as I opened the door for her, "it's chilly today" she responded, I smiled and nodded as she walked right past me. But what happened next was one of the greatest lesson I've ever learnt. The old lady came out of the store and handed me a $20 bill, "Good luck!" she said beaming.

I stood there dumbfounded. Without realizing it, I initiated a relationship with the old lady and provided an act of service without the expectation of receiving anything in return. I made an "ask" without actually attempting the "ask", and although I couldn't quite process what exactly happened that day I knew I struck gold. Not only did I rake in change every time I solicited donations, I had people give me $20s, $50s, and even $100s at times. My seniors and my officers were thoroughly impressed, "it's the smile" they would always say, but I knew it wasn't just that.

Golden Rules Before Making "the Ask"

No one can guarantee the outcome

Although I started to learn how to craft the perfect "ask" at 12, it wasn't until recently, as I expanded my networks and gained a diverse body of experience from sales to fundraising, have I been able to put my method into words. Of course, as your asks increases from a nomination $20 donation, to a $25,000 sponsorship or high-ticket sale, the level of difficulty increases and these rules apply.

The Golden Rules below are to help you achieve one goal, unfortunately not to guarantee what you ask for, as no one can, but to minimize the possibility of rejection.

Rule #1 - Who You Are Doesn't Matter

Personal branding isn't about "you"

Your ability and character is not validated by yourself but rather validated by others. Remember it's not who you are but it's who you know and what you represent. People recognize brand names, trending topics and demonstrable results that link directly to their provided contribution. In the case of high-ticket sponsorship or investment, who vouches and recommends you go much further than simply experience. Learn to associate with those who are successful and leverage off their credibility.

Rule #2 - Never Assume the Outcome

Expectations limit what you receive

Ignore the questions and assumptions in your head. In my case, I made the worst type of assumption, I assumed failure. The only way to find out what the outcome is, is to take action. Period. Do not allow yourself to think of any other way because there is non. There is no "get rich quick" scheme, you just have to do it and live with the consequences of your actions. I guarantee if you remove the idea of expectations in your life, you will receive more than you can ever imagine.

Rule #3 - Relationships Come First

Start early, start now

In life you never know when you may need to make an ask. Most people jump right into it, pitching for donations, sales or investment when the opportunity comes up. Ask yourself, why your cause? Why your product? Why you? We live in a time where the market is saturated with options and a majority of the time you are the discerning factor. Asking "how are you today?" Might work fine for a $20 donation, but when you're making a "real" ask, no one is obligated to help, especially not a stranger. Build relationships well before the ask and you'll find life much easier in times of need.

Rule #4 - Give Before Asking

Open the door first

The first question you should ask yourself before making an ask is "what value have I provided?" Asking always work best when you are either confident in your associated credibility or if previous rapport has been built. Often as a younger person, credibility is not easily achieved and little time has been spent allowing relationships to steep and build up. As Gary Vee would put it "jab, jab,jab, right hook", don't just walk into the ring and throw punches.

Rule #5 - It's Just a Numbers Game

Just Keep Going

No one says it was easy, and don't expect anyone to owe you anything. There are many factors to one saying yes or no to your asks. Sometimes interests and timings don't align or sometimes they're just dicks. Control what you can control. The only way to maximize positive outcomes is to create the opportunities that allow it to happen. Whether it's holding a can and asking hundreds of strangers for a few bucks, or emailing 100 sponsors for $25,000, the "next conversation" might be the key to it all.

#SeekToInspire