Welcome to the Sugary Scoop, my free weekly newsletter where I help you see and experience the magic of NYC that I love so much through curated events, experiences, artists, and community stories.

What’s new this week?

SUGARY LIST x COMMUNITY WEEK NYC (At Least Until Mid-May)

So from now until the end of Community Week NYC, the Sweet List will be shifting its focus from my typical curation to the nearly 150+ events that are happening in concert with the citywide initiative.

Yes, of course we already have a calendar for Community Week NYC which can be accessed HERE.

But, the Sugary List has a far greater reach currently and the intent has always been to help people rediscover their city through their natural interests so that is exactly what we are gonna do with the nearly hundred plus communities that have committed to joining our movement of social connection.

Whatever events I have already added, will remain as well as a few more curated additions for the month of April and into early May. 

After that, our events will be exclusively focused on Community Week NYC until May 17th.

We look forward to sharing all the wonderful and amazing happenings during Community Week NYC and hope that you and your friends will take full advantage of all the amazing programming that will be occurring in and around this amazing celebration of connection and community.

Let’s get into the scoop!

Sugary 🍬

Romanticizing the Art of Tripping

“Fail fast”…”Move fast and break things”…”perfect is the enemy of good”… and so on and so forth.

You’ve heard these phrases over and over again I’m sure.

Sourced from the annals of a tech dystopia headed by dubious figures of questionable thinking, this line of wisdom is often elevated as the holy grail and spoon fed to us through Harvard papers, Forbes articles, digital clickbait content and countless how-to books.

On the surface, there’s wisdom to be gained here:

Trade certainty for momentum, rapidly iterate, and learn as you go.

Seems like it makes sense because you don’t wanna get caught up in the minutia of things and accidentally sacrifice time and timing in service to a mythological idea of perfection.

Being a perfectionist myself, it’s been very challenging to get unstuck, and so the tendency for me was to adopt this way of thinking as sage insight and the answer to ALL of my prayers for self improvement…beyond any reproach.

The thing is though, I rarely hear anyone talk about the experience of it…

What’s it like to live through this experience beyond the click worthy sound bites?

What’s it actually like to go through this act of “failing fast” over and over again.

Honestly? It’s kinda brutal.

…and it comes at a real cost.

Let me be clear, I don't mean you shouldn’t “factor in” this line of thinking. But if we’re being intellectually honest, we need to ALSO factor in what kind of toll this takes on you and how you can better manage this process so you don’t get burnt out and become a charred remnant of your former self along the way.

Speaking from my own experience, I’ve endured so many challenges on a lot of things that on the surface seem like complete successes but the reality is they are at best ongoing “works in progress”:

Case 1: The Empathy Project

We didn’t have everything figured out when we launched the empathy T-shirt project. At the time, I was challenged to resist the urge of having everything figured out before moving forward and to catch the timing of everything that was happening in the nation and beyond.  So we rushed through this process and launched the campaign…

… I struggled to sell shirts quite frankly.  

Consistent sales wasn’t the issue to be clear. We sold shirts every week.

…but we had ordered too many shirts at one time as a way to save on cost and the irony is the cost of hosting such a volume at a fulfillment house adds up over time.

Pretty soon we were struggling to keep pace with the upkeep costs despite having regular sales.

Eventually, we found our light at the end of the tunnel and stymied the bleeding while accounting for most of the costs…but this didn’t come easy and took years after the launch to rectify this miscalculation.

Case 2: Fine Folk

Well I’ve written about this one already.  I launched this series to great fanfare and quickly ran out of funds to maintain consistency and as a result the series went dormant for 5 years.

It wasn’t until this year that I found the funding to make this a more sustainable endeavor…but that extended hiatus was torture.

I did move on, I did keep going but that “keep going” part involved years of disappointing prospects, a diminished sense of external enthusiasm and a creeping sense of self-doubt despite knowing I had something special in my hands.

Can you imagine for a second how painful that was for me?

Case 3: The Sweet and Salty Podcast

We started out the gate strong.  Recorded a whole bunch of content and cut it up as teaser clips. I had wanted to bank a bunch of episodes before we released things…but for a variety of factors that is not what happened and shortly after recording the initial podcast, we got caught up in all things Sugary as well as Community Week NYC.

All of a sudden any hiccup that didn’t allow us to film immediately whether it was venue, or lighting, or some other consideration however minor became the easy excuse to put off recording the next episode because we just had so much on our plate.

I think both DK and I’s eyes were bigger than our appetite, and so lesson learned but man has it been a frustrating one to take in while everything else has been going on.

So as you can see, behind many of my successes are a whole bevy of challenges that need constant “working-through”.

Failing as it turns out even when it is fast no matter how many iterations is emotionally, financially and socially expensive.

And when it comes to anything pertaining to building within culture, that goes double because failure in this realm isn’t just “data” it’s a matter of taste and point of view, more like anthropology versus merely analytics and ultimately its reputational capital.

Solely just romanticizing failure as a mechanism for momentum is a dishonest approach. 

Instead, consider the following thoughts:

Structured execution and reflection is paramount.

Unprocessed versions of your iterations don’t always need to be front and center.  Consider having a front stage and a back stage.  A front stage for your successful iterations and a backstage for all of your experiments.

Once you have this setup, be prepared to metabolize each failure.  That takes time and discipline to ensure that you’re learning the lessons after each failure and not just reinforcing bad habits because you’re too busy being “onto the next…”

Remember, you can take a lot of shots in life, but you don’t have infinite.

Failure can be a mindfuck.

There’s a psychological toll failure can take on you.  Most people that advance the fail fast theory make a critical mistake; that most people can detach emotionally from what they are doing.  While EQ deficient characters such as some of our top tech CEOs can do that, normal humans cannot. That pretty much never happens for most of us, especially because it’s so personal.

The experience can threaten your identity and can be emotionally draining.  Make sure you take the time for some level of self care and surround yourself with people that will help provide you with constructive feedback but done in an empathetic way…you will be at your most vulnerable point and to rebuild from that in a positive way requires good advice with good intent…that’s felt.

One size does NOT fit all.

Know the game for what it is not for what it pretends to be. Failure has real consequences in real life. Usually the ones espousing the wisdom of failing fast, can actually afford the aggregate consequences.

You have to know where you stand in this ecosystem and take whatever advice comes in with a grain of salt.  

If you’ve been blessed with a lot of cushion, that’s one reality.  But if it’s the other way around, you might have to tailor the wisdom to fit your circumstance. 

Ultimately be thoughtful with your constraints. Nothing about this life is cookie-cutter. Do take risks, but make sure the risks you take are actually survivable…

…and when you do survive them you’re ready to take those lessons seriously so the failure advances you forward and not just another war story to share on repeat. 

So, as you take that next step forward, do so confidently.  If along the way you happen to trip, recognize it for what it is, recalibrate and move on with reasonable caution…

…fast isn’t always the way…but forward always is.

Sugary 🍬

MICHAEL

1987.

I’d just settled into my new life in upstate New York when I first heard of Michael Jackson’s Bad Tour.  

Like countless others I was already a loyal subject to the King of Pop by that point. 

The only problem was, I didn’t have the means to attend a show nor the concept of what a “once in a lifetime opportunity” truly meant to override that aforementioned challenge.

That fateful decision cost me the opportunity to witness perhaps the greatest entertainer of many generations combined.

And so you know, I was BEYOND excited to catch Michael on the big screen in IMAX form which opened in theaters on Friday, April 24th.

I’ll save you the suspense.

The film is an incredible spectacle, framed around some of Michael’s greatest hits and covers his childhood basically up to his rise as an independent artist free from the shackles of his father’s rule and the Jackson family enterprise (fittingly, the launch of his Bad tour…fml).

For about two hours, you embark on a sleek cliff notes version of this period of Michael’s life and it’s very entertaining.  It’s almost like a tribute show and Michael’s actual nephew Jaafar Jackson does a shockingly vivid and accurate portrayal of his late uncle that is both stunning and convincing to the point I think most fans of Michael will truly appreciate the effort of bringing their revered icon back to the epic stage in cinematic form.

And if you love the music, at times the film feels like a gigantic music video so there’s no shortage in that department.  You’re getting the greatest hits in visual form.

What you won’t get here however, is dramatic depth.  You’re really not gonna get deep insights into character, motivations or in-depth breakdowns of the less comfortable aspects of Michael’s life.  Many examples include Michael’s talent within the context of Motown and the black music industry, Michael’s struggles with his own self image of blackness in the context of his skin condition and multiple surgeries, Michael’s affiliation with Diana Ross, sister Janet, Studio 54, the post Motown 25 drama, the Wiz and consequently how Quincy Jones came into Michael’s life also gone or glazed over. And of course, the more troubled second half of his life is omitted entirely (although there are rumors that if this film does well, they have a green light on standby for a part two that allegedly would focus on the second half of Jackson’s life and career).

However, at the end of the day, this is a movie, not a documentary and a dramatization with an express purpose to entertain and entertain it does

But what I suspect is that most folks will not be there for that.  What they will be there for is what I was there for, to get a glimpse of the grandeur and majesty of what that level of greatness was in absentia of the man himself.  

To feel for him, to celebrate with him, and most importantly to sing along with him and participate in the life affirming message he fought so hard to inspire within all of us.

So although this isn’t the most profound breakdown of Michael Jackson’s life and music by a long shot, it certainly is a more than competent celebration of the spirit of it.

And in these times… I think that’s probably the thing we need the most…

…from the only artist that could take us to those kinds of heights.

Sugary 🍬

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Thank you for taking the time to read to the end!

I hope you found something inspiring and meaningful in my content and until next time, explore the possibilities of NYC.

-Sugary

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PS. Don’t be shy and hit reply and tell me how you’re doing!