It was an unusually cool evening for a Vermont summer and as I walked downtown with two of my friends it was a complaint continually raised in our discussion. We arrived at one of our favorite spots, a little whisky bar on a quiet side street that was always unlikely to be populated by the town’s hordes of debaucherous college students. In the midst of a month long ‘no booze’ challenge, my only intention in going to the bar was to have a relaxing conversation with friends.
There’s something to be said about guaranteeing disappointment by forecasting your evening – the opposite is also true. My lack of expectations for how the night would progress served only to amplify my astonishment when I encountered what would seem to be the woman of my dreams. From the moment I walked in the door I felt an almost gravitational pull towards the corner of the bar where she sat. Her drinking partner for the evening had a sophisticated demeanor and the same flowing brown hair. There was a fair chance they were related and my money was betting on them being sisters.
I walked over, broadcasting confidence while secretly steps from a nervous breakdown, wanting only to see her face. I was rounding around the bar, positioning myself to get a better look under the guise of attracting the bartender’s attention when she turned her head. Our eyes connected and she flashed a smile that immediately highlighted prominent and overwhelmingly adorable dimples on either of her cheeks. Her eyes were soft, her smile was bright, and her personality glowed. Awestruck, it was at that moment that I knew I was about to do one of the most horrifying things of my life – I was going to attempt to talk to her.
I am a man of many words and … they all escaped me. I stood there awkwardly as I failed in my attempts to flag down the bartender and my confident facade rapidly deteriorated. I can’t remember what benign comment my friend made to start the conversation with her drinking companion, but without it I would surely have spent hours fumbling half-formed sentences in my head. Taking advantage of the conversation my heroic friend had intentionally started on my behalf, we started chatting as a group. It wasn’t long until we discovered that it was her mother, visiting from out of town, that she was drinking with. Still astonished by her mother’s youth, two thoughts immediately formed in my mind. The first thought was a realization that she was going to look gorgeous until the day she died (I’m sure I’m not alone in thinking that good genes are sexy). The second though was horrifying, as it dawned on me how difficult it would be to get those ten precious digits with her mom sitting an arm’s reach away.
The more the conversation progressed the more I found that we had in common. She was just starting a PhD program in Clinical Psychology and had a passion for everything cognitive sciences – principles I greatly enjoy injecting into my marketing. The sapiosexual in me was swooning and something told me the feeling was mutual. Business minded as always, it was only natural for me to look for an opportunity to ‘give’ something to her. I knew that, no matter how trivial, it would develop a deeper relationship and lead to more opportunities to get to know her. That ended up manifesting in the form of a recommendation to watch a rather fascinating documentary. I did well enough selling the idea that she would enjoy it that she was intent to watch it. At this point, it was only natural that I would need her contact information so as to share the link.
I took a breath, offered her my phone, and (faking as much confidence as possible) said, “add your phone number and I’ll text it to you when I get home.” I watched, bewildered, as she smiled with those adorable dimples and tapped in her contact details. It must have been the intoxication imbued by the attention of a beautiful woman because someone else was surely moving my lips when I suggested us watching it together … she smiled.
As I’ve known for much of my life, it was never heights, spiders, or even death that frightened me – it was talking to women. The more attractive, intelligent, and emotionally put together she was – the more horrifying it was to start, and maintain, a conversation. It was with this knowledge that a few years ago I began to derive a great sense of empowerment by mocking that fear.
Seeking to continually diminish the power of my fear, I developed an ever increasing appetite for rejection. This unsurprisingly, and quite expectedly, cultivated a rather colorful collection of stories that did nothing but illustrate the fact that rejection, no matter how gloriously horrifying, couldn’t kill me. And so it became that the more beautiful the woman, the more inopportune the setting, and the more likely rejection was imminent – the more inclined I was to approach her. “If I can do that” I would tell myself after each challenge, “then I can do anything – after all, I had yet to discover a headline reporting ‘death by harsh rejection’.” The more I did this, the more I charged failure.
I have yet to discover a headline reporting “death by harsh rejection”
— My Social Sherpa (@My_SocialSherpa) September 12, 2014
Realizing that glorious failure, with an almost guaranteed outcome, is far easier to seek out. It was the situations where success was an actual possibility where I experienced my greatest struggles. The difference, I discovered, was the element of certainty – the more guaranteed the outcome (good or bad) the less fear I had moving towards it as I was able to brace myself for accordingly. This, from my experience, had always seemed to be the reason that people stayed in jobs, relationships, and friendships they hated – it was what they knew and (even though they were miserable) it was far easier than venturing out into the uncertainty of something new.
It wasn’t until years later that I discovered the keys to taking my own advice. I had been interviewing entrepreneurs for a new podcast and, in order to overcome the fear of being on camera, scheduled a recording a day for thirty days. Just over twenty episodes (and twenty days) into the formation of the podcast I had the opportunity to interview someone whom I had been looking up to for years. He was a multi-millionaire and very well established personality in the industry whom I had only engaged directly in the process of asking him for an interview.
In the seconds following the recording I reflexively acted as my mentor had instructed me and spoke a very simple line, “Thank you so much for taking the time to share your story and insights on the podcast. I, and the entire audience (which was comprised primarily of my mother), truly appreciate it. Is there anything I can do to help you with digital marketing or social media?” He thought for a moment while I nervously gripped the arm of my chair off camera doubting that someone so established could ever use the help of a newbie like me. After what seemed like an eternity he responded, “Well, take a look at my website and if there’s anything I should be doing differently let me know!” I maintained composure and eked out a friendly smile as I let him know that I would most certainly take a look.
The moment the call ended I jumped out of my seat and screamed in celebration. I knew that he had just cracked open a door into his life and all I had to do to kick it the rest of the way open was to do what I had wanted to do all along – to help. Immediately following my celebratory dance party I got to work digging through his (and his competition’s) websites, social media accounts, and anything else I could turn up on Google. I explored everything and started compiling screenshots, resources, and links to articles for anything at all that might help him. My only two criteria were that it needed to be specific and it needed to be explained briefly (valuing people’s time will always win their favor).
I attached a screenshot of his backlinks using a free tool and connected him with a recent article suggesting a change. I detailed the reasons that shortened links can, in some cases, improve click-through on social media and shared an article illustrating that. I even explained the connection between site speed and conversion rates as I recommended he switch web hosting companies to improve sales. After three hours of digging, researching, and writing I had compiled a two page report. Attaching the report in an email I again thanked him for his time and stated that I hoped this breakdown was of use to him as it was the least I could do to repay him for taking the time for the interview.
I remember needing to have someone else click the ‘send’ button as I was so nervous my hands were shaking. I realized that this was the equivalent of handing someone a briefcase of money and doubting that they would be anything less than ecstatic – I was nonetheless horrified. About a day, and most of my fingernails, later I received a reply. He was overwhelmed with how much I had helped him and, after a few emails asking questions regarding the report, he responded with a single sentence, “Dude, this is amazing. What can I do to help you?”
After changing my pants, I sat in disbelief that after less than a month of launching a new business I had a well-known, multi-millionaire entrepreneur asking quite sincerely how he could help me grow. I spent the next several hours writing a one paragraph email in response. I explained that as an affiliate of his products, if he added a line of code to his website it would enable us to do Facebook Retargeting for his products to people who had visited his website. I made a joke about how this helped us to help him as we were deadlocked in a contest of who would be able to give more value to the other.
There’s something you should know at this point in the story and it’s something that I’ve never publicly shared before, the day I had sent this email – I had NEVER before run a Facebook Retargeting campaign. I had read about them, but I didn’t have enough traffic on my site to actually run one. While I knew, in theory, how to do this – I had absolutely zero experience in providing the service I had just offered. It was blind confidence, but I was intent being able to fulfill the promises I had made to him.
It took every shred of my energy to maintain that facade as we went back and forth over the next week before he finally called me to say, “I trust you. Let’s make this happen.” Using his data and my own money to fund the budget I created my first ever retargeting campaign. It probably took me three hours to make a handful of ads and crossed my fingers that something of significance would come from it. It was a week of constant refreshing as I watched the the ads’ performance like a bear protecting its new born cub. Just seven days after launching the campaign I ran the numbers and, with the $87 I had spend on advertising, had generated over $1,127 in commissions. Knowing that math wasn’t my strong suit I probably spent an entire afternoon refiguring the numbers before I realized that it was my blind confidence and determination to “figure it out” that resulted in a 1,341% return on investment … from my first ever experience with Facebook Retargeting.
To this day, I’m unable to tell that story without shaking my own head in disbelief. It still seems like a dream that this was how I landed my first client. Someone who, even when my company was less than a month old, trusted me to manage their marketing based solely on my conviction and paid over $100,000 in the first twelve months of the relationship.
Uncertainty will never be anything less than terrifying. It is only with confidence and conviction that you will overcome the very thing that deters the majority of living organisms from pursuing something greater. Learn to conquer this and you will be surprised by the simplicity in solving the rest of success’ equation.
Uncertainty will never be anything less than terrifying. Only with confidence and conviction can we overcome what others fear. — My Social Sherpa (@My_SocialSherpa) September 12, 2014