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  • Writer's pictureJake

It started in a little coffee shop on N. LaSalle

Can you account for a piece of your life that was ignited by one tiny moment? Perhaps you shared an uber with your future husband or wife? Maybe you went out to a bar that wasn’t your scene, but you had a drink with your next employer or business partner. The most valuable opportunities are all too often born from the moments that we never spend any time thinking about. It is so exciting to see life take a dramatic turn in a matter of seconds. It could happen anywhere, even in a little coffee shop on North LaSalle.

I was the most handsome haberdasher to beat the streets of Chicago, peddling suits to busy, arrogant, charming and rich businessmen... At least that’s what I told myself. “Floating,” was the most efficient way to gain a new client in my business of selling men's clothing, "like suits, shirts, casual wear, things like that..." Floating is sales talk for stopping busy guys who dressed well, on the street, to give them a quick pitch and earn their precious business card. If it was a good day, they would answer the phone and buy some clothes when I called later. Yeah, I did that, everyday.

Needless to say, I hated the idea of doing that. My first week involved an argument outside the tailor shop with my leader over floating. "It's all in your head. What is he going to do, punch you for asking him?" he would say. It was just so terrifying, but eventually I did it. I would get told no, yelled at, ignored and sometimes I would meet a really nice guy who was interested and handed over his card. I still hated it. What I didn't realize, as an arrogant 22 year old, was that floating didn't have to be about selling clothes. I was introducing myself to people. Eventually, fate would intervene.

One day, after about an hour of running around in circles and getting ignored by dressy douche bags, I walked back into our office building at 30 N. LaSalle, feeling defeated. I walked into the starbucks to treat myself to the only thing I had to look forward to, coffee. I saw a well dressed guy ordering before me that basically looked like a sketch of the ideal client. I was so mad. "This is god testing me about persistence or something. I know it," I thought, as I grabbed my drink. I wasn't going to give in. I was done floating for the day. I walked out the door. As I did, I just knew that I was punishing myself and something told me to try one more time. I turned around, walked up to the man and complimented him on his suit. I asked where he shopped. He was confused and couldn't remember but I explained how I outfitted sharp dressed men like him, in custom suits, in the convenience of their own home or office. We sat down to chat, only to find that he was planning to run for the United States Congress. He needed suits because he only had the one he was wearing and he said that he would buy all of his suits from me. Let’s talk about a day going from 0 to 100 in like 5 seconds.

Nevertheless, suits were sold, jobs were quit, presidential elections were unprecedented and bills piled up. Planning on grad school as a solution to indecisiveness and joblessness, I sat at my parent’s house reading over the GMAT book. That is what I was doing when an old client called me about helping him start his political campaign in Chicago to run for the US congress.

From that phone call, I found myself driving back to the city, eager to take on responsibilities for a political campaign that in the end, taught me little about politics but a lot about myself. Websites, marketing, social outreach, donors, emails and events all became my focus. I taught myself how to create an online platform and leverage it toward a fundraising goal. I now find myself writing to you here, using the skills I learned. Yes, this is how it happened. It took a political campaign, a future congressman, a suit company and a chance meeting in a starbucks to set me on the path toward what I want to do.

I am no expert at life, but to me it means that there is almost nothing you can do to predict or prepare you for what life has in store. Although a lot of shitty things were happening to me, a lot of amazing things were at work behind the scenes that were disguised as everyday commotions. The only thing I could do to prepare myself for the future was to stay positive and keep moving forward, no matter how shitty it looked ahead. There were so many insignificant little moments that added up to this exact moment. I’ll take the good and the bad of every ordinary day because it takes both to make a good story, worth reading. You never know when your life will take a dramatic turn amidst the chaos. I can’t imagine what my life would look like if I had never turned around that day and talked to the guy in the suit at the little coffee shop on North LaSalle.

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