Day 10 Thru 13 – Quality Over Quantity

Instead of updating this blog every single day, I thought it would make more sense to update it once a week, or whenever a significant challenge presents itself.  I thought this would be the best way to approach Social Skydiving because things are becoming very routine lately.  What does that mean for you readers?  I won’t be updating every night, but this blog will go beyond 30 days!  

With that out of the way lets talk a little about my adventures the past couple days.  At the very least I’ve been able to initiate conversations with folks at work, held a conversation with an older man about photography (I was out shooting when he came up to me and started talking), and say “hello” to strangers on the move.  I’m completing the goal, yes, but there isn’t anything new/exciting to learn from these exchanges.   Which means I’ve definitely grown and now it’s time to push myself even further.

I’ve been brainstorming ideas that will present a social challenge for me to overcome in time:

I want to ask a stranger for a photograph

Visit the Museum of Fine Arts and strike up a conversation

Take the train into work and talk to someone during the commute

What up to a girl at the bar and say, “You’re really beautiful, I want to talk to you.”

Visit the New England Aquarium and strike up a conversation

            As you can see accomplishing all of these goals will take some time and these situations are the ones I would rather talk about rather than chitchat with co-workers or saying “hi” passing strangers in the street or grocery store.  Some of those goals are going to be difficult and may entail progressing longer than 30 days.

I’ll be away this weekend dog sitting for my Uncle, which is a great opportunity to be adventurous.  Hopefully I’ll have good news and reflections to post!

Day 9 – “I currently struggle with…”

The words used in this introduction were spoken by a former colleague of mine who coincidentally was the one who suggested I join the Toastmasters organization.  It would come up when we were working out, typically with corncob pull-ups.  Instead of saying, “I can’t” he would always say “I currently struggle with…” and insert whatever it was he wanted to work on.  

            The only plan for today involved taking some pictures at a local park and hoping there will be someone there to interact with.  As luck would have it there was a girl sitting by herself on a bench pounding her finger tips on a Dell laptop.  I slowly made my way up to her snapping photos along the way, my plan was to simply say “hello” and see where it went from there.  If things went well maybe I could snap a candid photo of her once getting to know each other. 

That isn’t how the events unfolded.  As I made my way toward her another fellow sat down at an adjacent bench, his proximity was just close enough to see me fail (if that outcome were to occur).  In the end I chickened out because I was afraid of this stranger witnessing me potentially failing.  I didn’t open my mouth, and continued to explore the park capturing exposures.  Eventually another opportunity, similar to my earlier encounter presented itself, two girls sitting on different benches reading.  I sat down across from them and kept myself busy by reviewing my photos and responding to an e-mail.  Once again a rationalized why this opportunity wasn’t ideal and didn’t end up saying anything to either of the girls, not even “hello.”  It made so much sense at the time, but now my reasoning is completely silly.

“What if I say something to girl A and I hurt girls B feelings by ignoring her?  What if they both look up at me dumbfounder?”

I stood up and walked away feeling dreadful.  However, all was not lost and I did talk to a stranger on my way home.  It was in the late afternoon and while walking west the sun was scorching my eyes.  As I was waiting for the crosswalk signal to change I peered to my left and noticed a woman guarding herself from the sun. 

“Hell of a day to forget your sunglasses huh?”

She stared blankly at me.  A few seconds later she replied.

“Hell of a day to think you’ve forgotten your sunglasses only to remember there’s a pair in your bag.”

“Ha! Anything I can do to help.”

My goal was met, but the sting of failure from the park still lingered. 

            Now that I’ve had some time to think about it there are some valuable data points and lessons from this experience.  Some people are easy to engage, and others still present a challenge for me.  The more I go out there, talk to, and experiment, the faster I will find my line and eventually push past it.

As for lessons I learned I am my own worst enemy, and it’s not easy to admit.  Secondly, taking no action significantly rattles my core.  I hope I’m able to use what happened in the park to my advantage in the future.  Next time I feel paralyzed and unable to act I know what the alternative is, and it’s dreadful.  It reminds me of something Lance Armstrong once said, “Pain is temporary, failure lasts forever.”  His words have never held so much weight with me than they do right now.  Finally, not every day will be a homerun and the best way to approach the difficult kinds of days is to try and learn something.  If this was easy then I wouldn’t have to dedicate time and effort to it. 

I currently struggle with talking to strangers, and every step is progress.

Day 7 - Rained Out. Day 8 - Poker Face

Day 7 – Rained out.

Darn!  I was so excited to hit the town with my buddy Ahbi instead fate decides it better to drop a torrential downpour on Boston.  Ahbi got a head start on me due to setting up my iPhone, and after a couple of texts back and fourth to meet up he proclaimed the rain killed the scene.  Most places were dead.

I was really looking forward to going out.  Things are beginning to become a little stale, I’m not feeling a challenge.  Earlier in the week I talked about socially acceptable areas and how it felt like work was on of them, in these area’s it feel like I cannot fail.  I have to eliminate this mindset. 

Day 8 – Poker Face

Today was cake.  My friends Tina and Steve were hosting a poker night at their house.  All but one guest was a stranger to me.  In the beginning I was able to talk to two guys named Dan and Alex.  We hit it off pretty well by sharing our experiences with the new iPhone 4S.  Other folks poured in and the grand total ended up being around 17.  Throughout the night I exchanged some words with everyone, it was a great group and I loved the game.  Looking forward to round two.

Day 9 is one the way, but it's looking to be a fairly long entry so I wanted to do it justice before posting.

Day 4, 5, & 6 - Quality Engagements & Awkwardness

Day 4

Today was my first day at work as a social skydiver.  Unfortunately my boss loaded tons of work on me, so I wasn't able to go to the gym, or explore the building for strangers like I had intended.  Instead I made the most of my situation and worked on quality.  Which meant engage some of the people I see everyday in the halls but only greet them with a friendly hello. 

I have to admit approaches around the office are soooooooo much easier because, I believe, it's “socially acceptable” to make conversion with someone you work with.  No one is going to tell me to “Fuck off” or anything of the like.  Now you may be asking yourself why I didn't postpone my endeavor until after work? The reason is I needed to practice for a speech I had to deliver the next day.  You see I'm a member of Toastmasters International, which is an organization designed for people who want to practice their public speaking.  Anywho even though I didn't engage a stranger I'm still pushing myself socially and taking initiative engaging people.

Day 5

My speech went off without a hitch! In case you're wondering it was about developing healthy sleep habits.  As for social skydiving throughout the day I missed a couple of good opportunities to talk to strangers around the building.  For example, one of my fellow Toastmasters was talking about her weekend canoe ride along the Charles River.  This is something I’m dying to do but haven’t yet pursued, so using my newfound underlying curiosity strategy to combat fear I decided I would ask her about it.  I didn’t work  this time, I found myself waiting for the right moment which never came.  I’ll have to work on this!  There is no such thing as the right moment.

In the end I found someone, on my way out of the office, talk about cutting it close.  There was a girl following me out of the building into the parking lot.  I thought to myself, "hmmmm, I've never seen her before.". Which is exactly what I said to her,

"Really? I've been here for three years."

"Oh, they keep us pretty compartmentalized in finance."

"Same with database."

The conversation ended there.  It was pretty awkward, and I thought about continuing until I realized it was important to let the awkward silence remain.  I wanted to know what it felt like, to relish in it.  Sitting down in the driver seat of my vehicle I couldn’t have been giddier.  Pushing though my internal walls and attempting to initiate a conversation with this girl was overwhelmingly satisfying compared to the feeling of chickening out earlier in the day at Toastmasters.  In the end nothing happened, the conversation didn’t go anywhere.  It was awkward, but it’s not difficult to deal with.

Day 6

            Not too much to report today, I got a haircut after work and engaged my hairdresser.  Tomorrow my friend from work, Ahbi (pronounced Abby) and I have plans to tip back a couple of drinks.  This will be a perfect test of my progress so far.

Day 3 – Curiosity and Authenticity.

I’ve learned something these past three days.  I need to hang around my three-year-old nephew more.  Don’t get me wrong I see him once a month and talk to him on a weekly basis, but there’s a lot I can learn from him.  Being three years old, he’s the most curious little guy I know. 

I’ll start from the beginning.  Due to yesterdays lack luster performance I have to admit my spirits weren’t exactly soaring.  Also, because the cost of a washer and dryer in my building is highway robbery I’ve been venturing to a different laundry mat each week or so to clean my clothes.  It was a great opportunity to rebound.  After breakfast I emptied the hamper, grabbed Game of Thrones and sped off determined to succeed.

There I am, plunked down reading the next chapter of my book beside a girl whose also got her nose buried in what I assumed was Twilight, but didn’t get a look at the cover so who knows (yeah yeah, I shouldn’t assume).  BAM! lack of inertia kicks in (read day 1 if you’re confused) and I’ve hit a wall.  Again I don’t know what the heck to say.  Then doubt sets in because if I don’t accomplish this right now there’s a chance I’ll suffer the same fate as yesterday. 

She gets up and leaves before I open my mouth…I failed.

However, there’s another sitting three seats to my right.  All is not lost.  She has her face buried in a phone, and like clockwork I hit a wall.  What the heck do I say? I want to push myself beyond “Hi” and I keep coming up empty.  Eventually lightning strikes, I’m going to ask her what cell phone provider she has.  I have a new iPhone 4S coming this Friday and with my new purchase comes a new provider, Sprint.  I figure that will get the ball rolling which will lead into natural conversation. 

She rises, and leaves….you’ve got to be kidding me!

That’s disappointing but at least I thought of something to say to a stranger with a smart phone, which should take a micro second.  In the meantime I have to put my clothes into the dryer, and this task proves to not be as easy as it sounds.  You see, this establishment uses a credit card with a computer chip embedded within the plastic to keep track of your balance for washers and dryers.  After loading my wet clothes into an open dryer and selecting the preferred temperature setting I inserted my card to start the dryer.  “05 min” clocked in on the display with no visible controls to add time.  Perplex, I asked the girl next to me how to add more time.  She ran me through the basics and I decided not to waste the opportunity and told her about my experimentation involving laundry mats all around the area…this being my second one.  Afterward I thanked her for helping me and satisfyingly sat down to continue Game of Thrones.  Day three was complete.

After some reflection I came to the conclusion that I’ve been having trouble coming up with something to say because deep down I don’t really want to, for me forcing conversation is like any other crummy chore.  Going forward curiosity and, perhaps more important, authenticity should be integrated into speaking to strangers.  Actually, it should be the foundation. 

Day 2 - Does "Hi" Count?

Today was tough, but no without its opportunities.  My plan was to head to a local park in the afternoon to practice a speech about sleep hygiene and start to read “A Game of Thrones.”  Since it was still gorgeous outside I figured the park would be filled with people to talk to.  Unfortunately, I let this mind set destroy any opportunity which presented themselves earlier in the day, like the yard sale I visited down the street or a girl reading (and walking) her Kindle.  In both of these scenarios I thought of something to say, but instead kept my mouth shut for one reason or another.  No worries, I’ll still complete my goal at the park, right?

Wrong!

The park was baron of single people and groups of two or three.  All that remained was groups consisting of 5-7 people that turned out to be way more intimidating than I thought.  I got to thinking about ways to solve my dilemma; I need to change up my venue until I build up my confidence to approach strangers in this setting.  I’ve got some laundry to do tomorrow so with some luck it won’t be a problem to do a little social skydiving at the laundry mat.

So unfortunately I didn’t make genuine conversation with a stranger (at least I did it twice yesterday), but I did say “hi” to several folks as we encountered each other on the sidewalk.

I wish I could turn my brain off sometimes…it would be so much easier.

Day 1 - Do I Smell Bacon?

What an exciting day I had!  The morning was normal and filled with light errands and housework but in the back of my mind I knew there was a challenge to fulfill.  It was unseasonably warm in the city, and will continue to be that way for a couple of days, so taking advantage of the warm weather while accomplishing my goal seemed like a no brainer.   The plan was to snap some photographs in the city and figure out some way to engage a stranger.  I hopped on the green line train and made my way to downtown Boston, Haymarket station to be specific.  As I turned the corner onto Boston’s trendy Boylston Street I was struck by what seemed to be an infinite number of protesters.  Apparently the “Occupy Wall Street” movement has made it’s way up north, which doesn’t make much sense but who am I to walk away from a phenomenal opportunity to capture some exposures. 

Despite their vast numbers, the police ended up corralling most of the protestors onto the sidewalk and down Newbury Street, conveniently out of my way, leaving only tourists to deal with.  Plowing through the crowds I eventually found myself at the Apple store and gazed upon the memorial dedicated to the late visionary CEO, Steve Jobs.  Most of you reading this probably don’t know that I’ve been a huge Apple fan for many years so I wanted to see this spectacle with my own eyes and capture people paying tribute and their respects.

This gathering also presented an opportunity to achieve my goal for the day.  After capturing some photos I decided to stick around for some people watching.  Eventually I found myself standing next to a women maybe 10 years older than me who was also taking pictures of the various flowers, apples, candles, and sticky notes filled well wishes.  She was my target.  I waited for her to remove the 3 inch screen from her line of sight and would go in.  Waiting is the worst because, as is currently the norm, I cannot think of a thing to say to her.  My mind is totally blank.  Normally procrastination and rationalization will flood my thoughts by creating excuses, but I couldn’t let that happen this time.  I have to make genuine conversation with her, and it has to be more than a friendly “Hello.” Knowing I had a blog post to write I didn’t want to abandon this chance so I opened with a simple observation.

“It’s pretty amazing, one man’s impact.”  I said turning my head as to signal her attention.

“He changed so many people’s life, and his influence was enormous.” She replied.

“Yeah, and not just once or twice, but many times over.”

After a little more back and fourth I wished her a good day and continued down Boylston.  1 down 29 to go!  In hindsight it seemed easy, but I still found myself stricken by a lack of inertia.  That phrasing feels like the best way to articulate my state before attempting to engage her.  To say I’m afraid wouldn’t be right even though deep down fear is stopping me.  It’s hard to put it into words at the moment so maybe with more experience I’ll figure it out. 

My social skydiving didn’t end there though (Bonus points on my first day).  If you’re familiar with the geography of Boston you’ll know my next destination was the Public Garden and Boston Common.  Since it was so nice out the grassy hills were bustling with activity.  Groups of people tossing around a football, playing Frisbee, couples laying down embracing each other, and individuals relaxing with a good book and coffee plugged into an iDevice were everywhere I looked.  I had put away my camera for the moment and was heading toward Barnes & Noble to purchase the first Game of Thrones book until I passed a man walking his dog along a path.

“No…it couldn’t be, could it?”  I thought.

An A list celebrity just walked by me talking on the phone, at least I thought he did.  I immediately turned 180 degrees and followed the presumed celebrity, now keep in mind I’m toting around a Nikon D3100 DSLR camera and wearing a bright red plaid shirt.  I think he’ll spot me staking him and assume I’m paparazzi instead of a curious lad.  Instead of continuing down the path he stops to rest on a bench still speaking into his white iPhone 4.  I plunked down under a nearby tree hoping to snap a shot, but my damn kit lens zoom isn’t enough.  So I decide to sit down at a different bench, one that he’ll have to pass.  Roughly twenty minutes later the presumed celebrity and his dog pass me and I’m sure…it’s him.  He manages to create quite a bit of distance between me until a girl spots him waiting at the cross walk.  She talks to him for a little while and from a distance I see her reveal her phone for a picture.  They part ways…time to skydive J

I walk right up to her.

“Hey!  Wasn’t that Kevin Bacon?

“Yes!” she promptly answers still on a high from her experience.

“I KNEW IT!  But given my camera equipment I was way too intimidated to ask him for a picture.”

“I know was you mean, I was soooooooo nervous and intimidated but he couldn’t have been nicer.”

I give her the run down of my stalkerish behavior and my surprise that no one noticed it was him outside of the two of us.  Some small chit chat went on until we both parted ways, all the while I was thinking how cool it would’ve been for my first day of social skydiving to be with Kevin Bacon.  This girl was terrified but took a risk regardless and Kevin Bacon couldn’t have been nicer…I guess I have work to do.

I’ll probably do more reflection later in a weekend recap, but there are stark contrasts between my two encounters, which should be pointed out.  The lack of inertia wasn’t present the second time around, and this girl was beautiful.  Under different circumstances I would never talk to her, but I was genuinely curious to know if that was really Kevin Bacon.  The curiosity took over and didn’t allow me to over think the situation.  This is good.  This is progress.

Day 0 - Introduction

Welcome!

If you found this blog you are probably familiar with the idea of Social Skydiving developed by Brad Bollenbach Here. 

My name is Mike, and after stumbling upon Brad’s 30Sleeps blog back in January 2011, I was hooked.  That’s as far as it went unfortunately, reading and fantasizing about how amazing it would be to have the ability to walk up to any stranger and make conversation with them.  Deep down I was still too scared, but enough is enough.

It’s finally time I dedicated some serious energy to social skydiving and I thought creating a blog to chronicle my adventures instead of keeping a personal journal would be beneficially for two distinct reasons.  The first is raising the level of accountability for accomplishing this goal.  I live in Boston, MA and that means there are plenty of opportunities to engage strangers on a daily basis.  However as opposed to using this as an opportunity I use it as procrastination and wait for the perfect situation, which never presents itself.  Knowing there is an audience out there will help with creating a significant cost of failure.  The second reason is to reach others like myself who read about personal development and social skydiving but haven’t yet begun their journey, like Justin did for me

http://socialskydivingwithjustin.posterous.com

It all begins tomorrow so stay tuned, and wish me luck!

-Mike