The Comfort Of Possibility

When I walked into the office on a Monday morning and looked at my funnel of future deals, I felt really good. Like "get another cup of coffee and chat about the weekend with the receptionist" good. I had over 50 open deals. 50! Far more open deals than anyone else in the office and I walked with corresponding swagger. Now, fast forward three weeks. I'd only closed two of those deals.   All of that possibility had only materialized into results twice.

That comfort and glut of potential had robbed me of the urgency of converting possibilities into results.

Turned out I'd believed my own hype and that blankie of possibility was robbing me blind.

So I got rid of 30 deals in three days. I asked the honest question: "Is this actually a deal, or does it just look like it could be at some point down the road?" I called and turned the screws on the prospects I thought were open deals and directly asked for the business. I applied enough pressure to learn if they were just being nice or actually seriously considering my proposal.

You know all of the possibilities that the world has presented to you? All of the things that lie ahead of you and all the amazing things that you believe you'll do with your life? Rubbish. You probably won't do them. You probably won't put in the work to close the deal. You probably won't lean into the pain long enough to break through. You might, but, let's be honest, you probably won't.  You're used to getting participation trophies for trying and that is how we've been trained to look at results. "We gave it our best shot."

There is a very real chance that this amazing feeling of having all that potential, all those possibilities ahead of you is the reward that will be enough for you.  That feeling is intoxicating and is so much easier than actually realizing your potential.

But a feeling is all it is.  And for some, that will be enough.

But, for others, that feeling will be demon they wrestle for years, for decades to come.

The demon that says, "you don't have what it takes to actually do those things, do you?"

The demon that says, "think about how much you'd have to give up to even try, just to TRY, when you know you'll probably fail!"

The demon that says, "your possibilities are your reward, those results are for people with more talent than you."

But those demons don't know how to deal with the soul willing to risk comfort for the chance at capturing potential.   While they may grow louder as you take that first step, they're quieted by the second. And silenced by the third.

It is only in action that our possibilities are worth acknowledging. It is only in daring that our potential has any worth.  And it is a choice that we must learn to make every single day.

So here's to you and to the possibilities that lie before you.

But most of all, here's those brave enough to see those possibilities become your reality.

Get To The Other Side

It is an age old question with a lot of creative answers, but I'd like to prove that the chicken's actual reason for crossing the road was in fact a strategic move all about perspective that could be gained from the other side. This photo was taken on the corner of 27th and 5th Ave.

This photo was also taken on the corner of 27th and 5th Ave.

Both photos were taken at 8:15am looking north, the direction I was heading.

One of these photos shows the canyons of Midtown South emerging on the horizon with no memorable benchmark between me and the horizon.

One of these photos presents a clear and unmistakable point of reference by which to measure my progress against.  It also gave me a lot more motivation to keep fighting through all of the pedestrian traffic jams that were between me and my destination.

So, when thinking about the year behind and the year ahead, sometimes you just have to make like a chicken and cross the road because the perspective you need of the Empire ahead is on the other side.


When Bruce Wayne decides to get back out on the streets of Gotham as the Batman, he does so because others need him to. He does so because it seems like the right thing to do and that he is the right person to do it. All of those things are true. There isn't another super hero waiting in the wings on. But, (spoiler alert) when he comes up against the pure evil of Bane, he stands no chance the first time around. The reason was simply the "WHY" In one of the best TEDTalks out there, Simon Sinek talks about the difference between how good companies and great companies talk about what they do. Good companies explain what they do and then share how they do it. Great companies explain WHY they do what they do and the beliefs that back their motivation and then may also mention how and what they do to help round out the story. It is an 18 minutes well worth the time.

In thinking about Bane's WHY vs. Batman's WHY, it was crystal clear that Bane would win out in their first encounter (that and there was almost two hours left in the movie...)

His belief was forged in something bigger than himself and a quest that had nothing to do with personal gain. Bane's belief was the playing out of a vision that would last much longer after he was gone. The belief behind Batman's WHY was conjured at best.

When advising start-ups or taking a look at any new projects myself, the first thing that I am learning to ask is WHY. WHY does this project, opportunity, or company care more about the problem they're solving and the solution their providing than everyone else? WHY am I willing to turn down other initiatives and potentially also successful endeavors to see this one through? WHY does this campaign towards something that others are also considering get their first and with more gusto?

If I can't answer that question, I too will end up missing a vertebrae and exiled to a professional living hell until I find the strength to act first on belief and then out of confidence in that belief.


Believe it or not, it's halftime. The craziness that began 2012 has't stopped for 6 months and now you are on the down hill side of this calendar year. Everything that you said, "This will happen in 2012" that hasn't, only has 26 weeks left to be accomplished.  The way this year will be remembered hangs in the balance and you've been given a moment here at halftime to make sure that you don't let 2012 slip through your fingers. Let's think through your performance in the first half. You took some good shots, you push hard on some of the new ideas that you'd been tinkering with, and you even exploited those that stood in your way and made their defense look weak. But, you also took more time to get to the goal than you needed, your pace started great but was dragging by the time the end of the 2nd quarter rolled around, and you allowed others to walk all over you when it came time to block their blatant attempts at accelerating your defeat.

So right now, in this slow moment between halves when everyone else is sipping Gatorade and reliving their one highlight moment of the first half, this is the chance that you've been asking for to clean the slate from what was and take command of what's to come. It's right now that you can lock in on the strategies that worked in the first half and get rid of the ones that didn't and the ones that held you down. Right now is all that matters because right now is all you have.

This year won't be won out on the battlefield, this year will be won the place that all great victories are won: in the moments of preparation and commitment in the in between.

Hustle now or forever hold your peace.

SAM Test

This isn't 3rd grade where there is no such thing as a bad goal, there is. "Being Happy" is a horrible goal. The idea of happiness isn't, but as a goal it is. How do you define "being happy?" When you have achieved that state, do you have to stay there? Or, it is a "more often than not" kind of thing? And, if so, how will you know for sure that you have achieved it? Will you write down the number of minutes each day you were able to keep yourself in that state of happiness?

In my post yesterday, I talked a little bit about the high level story lines that I've started to pull out from the unfiltered ramblings that I jot down when planning for the year ahead. But, I realized after getting some feedback (from you the reader, thanks!), that I left out how I determine if something will in fact make it from the hair brained idea phase to the committed and inked phase of the year.

I've had the chance to be a part of a lot of "goal setting" meetings, both professionally and personally with mastermind style roundtables. It is always amazing what you can learn about a person by the goals they share and the approach that they take to prioritizing what they think are the have-tos for the next year. But, in those meetings and roundtables, I've also hear a ton of really bad goals, like the previously mentioned "being happy."

For me, in order for a goal to be counted as a legit commitment, it must pass the SAM test.

Significant: It has to be something that you don't know exactly how it is going to happen and it is going to take your very best to continue to pull the pieces into place so that it can occur.

Attainable: In the time frame of the goal being set, in this case 2012, it has to be something that can be achieved. If not, you will end up failing and knowing that you are going to fail is never a good place to start.

Measurable: If you can't precisely define when you have arrived and what steps and progress you are making along the way, how will you know your are getting closer? You must be able to tick of units of success as you go.

By having these checks and balances in place, I've been able to take big lofty ideas like "Being Happy" and boil them down to specific goals that aim towards the bigger idea AND pass the SAM test.

I had the chance to spend some time with Jeff Swartz, the former CEO of Timberland. In talking about goals he put it another way: "It has to be big enough to matter, but small enough to achieve."

Happy Resoluting.


I am in an incredibly awesome position as I think through what I want out of 2012. I haven't finalized my next career move now that Gowalla has been acquired by Facebook and therefore am thinking about and writing my plans for next year with a ton of unknowns attached. And it's awesome.

For years, I've broken my annual and monthly goals down into 6 categories as I think through what I expect of myself:

- Professional

- Financial

- Relational

- Spiritual

- Physical

- Educational

I start with very broad strokes in each of those categories, everything that pops into my head gets written down. I usually end up with 10-12 ideas for each category. Then, once I have all of those ideas in front of me, I take a big step backwards and look for trends, themes, or story lines that need to be pulled out and highlighted. What did I tell myself about myself in the free flow of goals and aspirations for the next 12 months? With some intentional thought and a large cup of black coffee, I was thrilled by what I found this year. The unknowns of what my business card will say I am and what I do in 2012 actually freed me up to think about things I hadn't before. I am still refining what I will commit to for 2012, but the big idea(s) are there.

We are all telling a story with every action we choose to take or not take. We are both the protagonist and the antagonist of an epic tale more commonly referred to as our life. Going into the new year feels fresh and full of possibility, but, 12 months from now, one thing is guaranteed to be true: 2012 will only ever be what we choose to make of it.

Happy New Year.

Continuous Learning

For the past couple of years, I've had what might be called an "obsession" with TED and the amazing talks the world's brightest minds share there. I watch a TEDTalk everyday that I'm in the office for lunch as a part of my hopefully life long continuous education. Since each talk is no longer than 20 minutes, the amount of intellectual and motivational gold that can be found on the TEDTalk YouTube Channel is incredible and perfect for the quick lunch and learn.

In an amazing interview with Warren Buffett and Jay-Z (that I detailed yesterday),  the discussion of "what advice would you give" led to some great thoughts from the two legends. Mr. Buffett said “The best moat that you can have is your own talent. The markets can’t take that away from you. Neither can competitors or inflation.” This is the kind of truth keeps my curiosity and hunger for knowledge and truth piqued.

As I've gone through over 100 TEDTalks in the past two years worth of lunches, I've taken a ton of notes and incorporated what I learned in a lot of the projects that I've worked on. I've also kept a list of my favorites. On Labor Day, a day that a lot of folks might have a little bit more free time to work with than other days, I thought it would be worthwhile to share them and encourage some on going learning.

Check out my Top 10 speeches and let me know which ones are your favorites in the comments. Also, if you have a favorite, let me know. Would love to keep learning.

Barry Schwartz

The paradox of choice:

Sir Ken Robinson

Do Schools Kill Creativity

Bring on the Learning Revolution

Hans Rosling

No more boring data

The magic washing machine

Elisabeth Gilbert

A new way to think about creativity

Derek Silvers

Keep your goals to yourself

How to start a movement

Malcolm Gladwell

What we can learn from spaghetti sauce:

Tony Robbins

Why we do what we do:

Richard St. John

Secrets of success in 8 words and 3 minutes:

Simon Sinek

How great leaders inspire action:

Daniel Pink

The surprising science of motivation: