Many people in life and business haven't figured out the art of asking. Far too many of us look at important people as unreachable. A funny thing can happen when you ask someone of a high level status to do something for you; they just might actually do it. Asking someone to do something is extremely hard, but on the flip side, the reward can be extraordinary.
I recently realized a recurring pattern in my life where I have asked a lot of people for a lot of help with projects and planning. Great projects are hard to pull off alone. It's humbling when I look back on it and I hope that it helps anyone reading this to get the courage to ask for things when they need them. The only important and crucial caveat would be to make certain that what you are asking for is worth it. You may only get one shot at it for your entire life with this particular person. Make sure it is for a good cause, an amazing project, or something that will bring someone else extreme value. It is also important to understand the motivation on why the person you are asking would want to participate, before you ask.
I have done a lot of thinking about how and when I first caught the bug of asking for things. For me it all started with athlete's autographs.
*Disclaimer: I am doing some major name-dropping and humble bragging here.
Waiting by the mailbox in the 1980s
In the 1980s, I loved baseball and all sports really. It is something that I kind of gave up in my adult life because I just don't have the time for it. Instead I focus any free moment on studying my craft, being a practitioner in what I preach, writing, reading and consuming. But back then, as a boy born on Long Island you could not rip me away from the New York Yankees and baseball in general.
I thought of it recently because one of my first big asks was writing to former MLB player and Today Show Sports Anchor Joe Garagiola. Sadly Mr. Garagiola passed away this week at the age of 90. When I wrote to him in care of the Today Show, I never really thought he would take the time to send me a signed autograph, even though that was exactly what I was asking him to do.
This has been a key aspect every single time that I have asked for something. I never really expect them to do it.
The autograph came in after days of running to check my parent's mail. Getting that first one encouraged me to see what else I could do. I next wrote to legendary Yankees' broadcaster Phil Rizzuto and he sent me a bunch of signed things.
Mind you, this was all pre Internet, so it involved getting my mom to take me to the library and hunting down books that contained contact info of the Major League stadiums and venues.
I got braver and braver, receiving signed items from my heroes Don Mattingly, Cal Ripken Jr., Wayne Gretzky and countless others. I even was able to write to my dad's hero HOF Duke Snider of the Brooklyn Dodgers and get him a signed item.
Revisited for career building advice
As I entered the workforce after college my asking became more career and advice focused. In the mid 2000s I reached out to some of my business heroes over email. Marketing guru Seth Godin, tech publishing legend Tim O'Leary (he coined the phrase Web 2.0), Jimmy Wales the creator of Wikipedia, and countless others. Many times I would just guess their email addresses and they would work. They all responded and I interviewed them for various projects. I still email Seth Godin on a regular basis and he still always responds. Amazing!
For better or worse, it works
In 2008, when I was planning how I would propose marriage to my wife, I used this skill set again. My wife is a huge art fan so I contacted an amazing glass artist named Josh Simpson, who I wrote about earlier in my career and met at a trade show.
The key here was that I already had context with Simpson. I had participated in his Infinity project, where people hide his tiny glass planets all over the world. I told him that I wanted to contact a museum and have one of his planets with the ring. He made this amazing glass planet with a spot for the ring on top and carved our names into it.
Next, I convinced the Museum of Art and Design in New York City to let me hide the planet and the ring in one of their exhibits. I told the hotel and restaurant of my great plans and got a free penthouse stay upgrade and private room for dinner with our family. I was nervous as hell but was able to create one of the most amazing days of my soon to be wife's life, all by asking people to join me in my special little project.
Business advice and blogs
In 2012, I found myself out of work and starting my own social media consulting company. I had been consuming business expert Gary Vaynerchuk's books, articles and videos for well over a year. I reached out to him over email for some business advice and he gave me some amazing advice about how hard it would be to scale. Today, we interact on social media often, he follows me on Twitter, we are connected on LinkedIn and just sent me an autographed copy of his book.
In 2013 I attended a talk by the queen of new media Arianna Huffington with some friends. During the talk she gave out her email address and said we are always looking for new voices. Someone in the crowd was skeptical that she actually checked that email, but I scribbled it down on my phone as fast as possible. I pitched Arianna my first blog titled This Is Wound Care, Coolest Specialty in Healthcare. Soon after, her team set me up with my own blog and I have been able to cover a range of topics including the opportunity to interview celebrity chef Jamie Oliver. It also gave me the courage to start blogging on MedCity News, LinkedIn, Social Media Today, Healthworks Collective and guest write on other sites in healthcare.
Leading up to the Seinfeld birthday project
When my father was nearing the end of his two plus year battle with non-smoking lung cancer, I tapped into the art of asking again. In the two to three weeks leading up to what would have been his 67th birthday, my wife and I orchestrated a plan to get the cast of Seinfeld to reunite with video messages in the form of a virtual birthday party for him. It was his favorite TV show and seemed fitting. The response was amazing, shocking, humbling, and extremely emotional for our family. The story of the Seinfeld Birthday Project went internationally viral, received more than 1 million YouTube views, and was featured in hundreds of newspapers, blogs, TV shows and radio programs. 
I will never be able to thank enough the amazing actors like Julia Louis-Dreyfus, Michael Richards, Jerry Stiller, John O'Hurley, Patrick Warburton, Wayne Knight, Al Roker, and countless other actors. I will also never be able to personally thank all of the agents, PR people, friends and regular people who helped spread the project and let it grow via the Internet.
A friend and mentor recently told me that I know what motivates people unlike anyone he has ever met. While this might be part of the equation, I think some people are really afraid to ask. If your intentions are pure and honest, you will be surprised at the results. By the way, these same tactics can work in business if you are passionate about the product or service you are offering to your consumer. You also have to prepare yourself for a lot of no responses along the way. Sometimes you won't get any response at all. If you build up a thick skin this won't bother you. My focus and dedication to wound care education will require some more asks on some awesome projects that we are working on. Stay tuned and as always, thanks for reading my content.