The Pursuit of Awesomeness

Today I completed the most significant project of my life. It’s worth taking a second to honor that.

In May 2008, a month after I joined JetBlue, I was asked to support a colleague in the creation of a huge project. JetBlue’s legendary Principles of Leadership series is one of the reasons I joined the company, and amazingly enough, we were to create the third. Further, the other two classes were directed at teaching front-line leaders what leadership looks like at JetBlue: this one was directed at the top level of leadership–Directors, Vice-Presidents, and Senior Vice-Presidents. The scope of this project could not be exaggerated, and I was very wet behind the ears in my field. I had a moment of fear, but of course, I was excited beyond belief.

I think that I was enlisted mostly in an apprentice capacity, to get me exposed to big projects, but I quickly became a full creative partner, out of necessity as much as out of my passion for the project. My colleague Greg and I worked long nights for weeks on end, trying to create something that made sense and was valuable. Since this was such a high profile project and so important to get right, we were constantly rethinking and rethinking the project from scratch to incorporate new feedback from each new concerned party. It was exhausting.

This was a solid nine months of serious creative work, and along the way, I learned the meaning of the term “burnt out.” I don’t think I really understood it before. To be burnt out is not to be tired; it’s to have overcome being tired over and over again by force of will and your love for what you’re doing. It’s doing that enough times and pulling so much from yourself that you wake up one day with no love left.

The dry run was a debacle of unprofessionalism meeting high expectations. Greg and I got up in front of our team to deliver a class that we had been revising the day before, a class we had barely practiced and which was full of mistakes. About a week afterward, one of my leaders pulled met with me to deliver some bad news: I’d been largely pulled from teaching duties for the class, a vote of no confidence that I understood and even somewhat agreed with, even if I admitted that I was deeply disappointed by it. When we ran the pilot class for the first time, we were met with a group that came excited and did seem to get something from parts of the experience, but ultimately left bored and vocally disappointed. Greg and I made yet another overhaul, which we thought solved the problems. We prepared properly this time, and then held our breath. The first class’s participants were our team’s Director, the other Directors in our Department, our VP; observing were my Manager and all of the other Managers on my day-to-day team. Namely, every single person we could consider a leader, other than the CEO, was in one room; and we were supposed to tell them something they didn’t know about being a leader. This is a lot of pressure to put on a twenty-nine year old.

And we were a huge hit, delivering a class that was considered engaging, entertaining, and highly valuable. Post-class surveys showed a consensus that we’d given them two-days well-worth their extremely precious time. Over the next few months, we delivered the same class to the senior leaders of almost every Department, people I admire and would have been nervous to talk to months before.

Today we completed the last official class of the project as we brought the Corporate Affairs department through, comprised of the people in charge of Legal, Government Affairs, and Corporate Communication for JetBlue. It was considered another significant success. The project isn’t completely put to bed, as we may run a significantly-changed variation of it at some point in the future, but essentially, to quote the Muppets, we have done what we set out to do.

So that brings me to now, sitting cold outside my apartment, trying to type out a few thoughts before going inside to see my Ginny for the night. I ask myself what I’m thinking. There’s a common (I think Buddhist) phrase that I see in books and magazines now, that the goal is not the destination but the journey. It’s that you shouldn’t live your life dependent on whether you achieve success; instead, focus on the joys and challenges along the way. There’s certainly something to that; you get to live in your success for only, what, a few days? And then life moves on, and you’re back to spending months in pursuit of another possible goal. If the journey were miserable, it just wouldn’t be worth it.

But at the same time, if the destination gave you nothing, wouldn’t the journey be meaningless?  What does it mean to succeed in this kind of serious way? What do you get from it?

Let me start with my emotions right now. If I had to sum them up, they would be a profound kind of pride and calm. My mind naturally went to the details of the last year and a half, pausing over every challenge to note just how hard this was and what kind of accomplishment it is. The funny thing when you’re in the midst of the journey is that you can forget the challenges as soon as you’re past them. It’s just kind of amazing how many times I was beating my head against the wall and then how natural and simple the final product is.

I think also of the effect of my efforts. The goal was to get every department in JetBlue thinking consciously about the health of the company and of their particular departments and then doing what they could to improve it. I think we did that. I think we made the company healthier. And I think that we have potential for further impact by bringing up the lessons of the class in future events. We have a base to build from. It’s hard to disagree that the company has become better in the last year. Do we have a hand in that? It’s hard to say, but I think so.

Next, I built a reputation for myself and a comfort with some pretty important people that intimidated the hell out of me before. That’s huge, and it will provide a platform to work with these people in the future.

Finally, and I think most importantly, I think grew tremendously. My favorite compliment from the last few years was that there was tremendous difference between how I was in the front of the class for the Dry Run versus for the last class. I went from vague and uncertain to a credible expert with command over my classroom and comfort with my participants. Nothing is more valuable than the fact that I can now trust myself to take on much more interesting goals than I could before.

So tonight I sleep. Tomorrow I put some of this new confidence to use, as I work on another class, “Supervising a Shift.” It’s one that I’ve been working hard on for months. I think it has potential but isn’t yet good. But I’ve made the latest Principles of Leadership class now. That’s something I know I’m capable of. So why can’t I do it again?

[Part one: A New Focus Pt. 1: My Top Two Mental Strengths…]

And that brings me back to a key weakness of mine–details. Nine out of ten times when I fail at something, it’s because of a failure with details. I have trouble noticing them, retaining them, remembering to check on them.

The other day, I went out of my way to make sure I’d taken care of all of my work commitments before I went on vacation. I felt pretty good about myself, that I was being responsible when it was truly inconvenient. One of the things that I had to do was significantly modify a file and send it to participants of a class I’d taught. I made the modifications, wrote an email to the participants…and then sent it with the original, unmodified file. Such an easy thing to correct, but it just wasn’t my natural inclination. You can excuse that once as a simple mistake, but it was an embarassing one, and it happens much too frequently.

I contrast this with my girlfriend, Ginny, who is excellent with details. She remembers the exact time when a flight we are taking is going to take off or land, the names and occupations and histories of people we meet. More deeply, she cares about getting these things right, in a way that’s similar to my concern with the structure of a class I’m creating. I care when I mess up because of my weaknesses, but it’s a chore to me to focus on getting them right. I look at her and people like her as something of an alien phenomenon. They are doing something different from me–I have some inklings as to what it might be–but I don’t know what that is clearly. And I definitely have a long way to go toward mastering it myself.

[Ginny says that I am blowing this out of proportion, though she would agree that it's not my strong suit. Fine, I've been concerned with it for a while now, and it's still not a strength. That's frustrating, and I want to fix it.]

[Now she feels weird that a stray comment she made is ending up in the blog. That'll teach her not to think!]

So that will be my focus for a while: how do you train yourself to be strong at details? There are a lot of related topics; including habit-building, memory, aligning your emotions with your goals. I’m looking forward to it and to moving forward with a clearer sense of purpose.

I’ve been playing with the format of the blog for the last few months. My goal is for it to be a productive forum for my education while still being convenient enough to fit into my crazy schedule. To do that, I’ve played with writing essays as entries and with posting related news. The blog now is pretty convenient for me; I post relevant news on a regular basis and I write commentary when I have time.

But I’m not comfortable with the directionlessness. I don’t feel the blog (and hence my education) is going anywhere. So here comes another iteration. I’m going to try to keep the majority of my entries related to one central topic at a time. Likely, these topics will be things I am having trouble with, especially in terms of core mental habits.

I have a problem in mind, but in order to explain the problem, I’m actually going to start with some key strengths. I am describing them not for the sake of congratulating myself (I do that enough in private) but to try to clarify what I mean by a “mental habit” and to paint the full picture, since I think my strengths and weaknesses might be related.

I tend to be good at things that are related to maybe two core mental habits. First, I pay close attention to my emotions and always try to understand them and use them for course-correction. To borrow an idea from my favorite filmmaker Joss Whedon, the key to success is love. If you know what you love, then your emotions can guide you in your pursuit. They will tell you when something’s wrong and you need to pay more attention, and also when you can just trust things as they are now.

When I am designing a class for JetBlue, I’m useless at it until I understand how the class could possibly help someone be better at their work. That’s a subject that I care about passionately. Once that connection happens, I am very naturally always on the hunt for ways to make the class better. When someone makes a good suggestion, I leap at it. When the design isn’t gelling, I am deeply frustrated in a way that can be bizarre to others. I plug away until I fix the problem. This can even be crippling for me at times when I don’t see how to solve a problem, but there’s a strong incentive then to figure out why I don’t see how to solve the problem.

The second thing I do is to seek to understand the deeper or broader meaning behind particulars, and I am concerned with my level of certainty in forming those conclusions. If a coworker is having trouble with their manager, I want to understand why that trouble exists, and I question the answers that I come to or that others provide. It’s the only way to do what I’m trying to do with this blog and have it relate to reality at all.

These things are just an absolute part of me. They do not happen automatically and I can’t guarantee that I always do them successfully, but the idea and the emotion to do them do come to me automatically. So why couldn’t I make something else an absolute part of me, something that I’m maybe not so good at?