Big Wins and Moon Shots


My dad sent me this video a few months ago. In this video, Billy Joel, while doing a Q&A session at Vanderbilt University, is asked by a student if they could play “New York State of Mind” together on stage. Watch the video if you want to see what happens; it’s a great example of a seemingly impossible ask paying off with an epic win (also known as a “moon shot“).

In our lives, we have a tendency to shy away from these “moon shots.” For good reason too; they require significant effort, are usually uncomfortable, and are very unlikely to result in any success. But for that 1 in 1,000 that does result in a success, brace yourself for something incredible.

One of the challenges in life is making time for these high risk, high reward activities – the moon shots. Companies like Google are already embracing this idea. Self driving cars? Top secret Google X projects? These are designed to find the next world-changing idea, rather than steadily incrementing on currently-existing offerings.

Thankfully, for individuals, this task doesn’t require immense product development and hundreds of the world’s brightest minds. It simply requires a willingness to go after the unlikely. Examples:

  • Emailing an executive at your company, and ask if he/she would be willing to grab coffee
  • Starting a business on the side of your 9-5 job.
  • Moving somewhere new
  • Investing in a new skill that could substantially benefit your personal and/or professional life

Some moon shots I’ve been working on lately (or have happened recently):

  • Pressing the reset button on my career in late 2012 and moving to San Francisco
  • Learning to code for 6 hours every Saturday, for a potential pivot towards a more technical career (in progress)
  • Launching a Meetup group to build a sense of community around electronic music in SF

While some of my other moon shots have failed pretty miserably, the three above are a few recent ones that have significantly impacted my life for the better.

Stop Being So Realistic

Being “realistic” is the killer of moon shots. This article by Malcolm Gladwell in New York Magazine – describing the unintended costs of constructing a railway line connecting Boston to the Hudson River – sums up my thoughts on the idea of being “realistic” all of the time:

Everyone was wrong. Digging through the Hoosac turned out to be a nightmare. The project cost more than ten times the budgeted estimate. If the people involved had known the true nature of the challenges they faced, they would never have funded the Troy-Greenfield railroad. But, had they not, the factories of northwestern Massachusetts wouldn’t have been able to ship their goods so easily to the expanding West, the cost of freight would have remained stubbornly high, and the state of Massachusetts would have been immeasurably poorer. So is ignorance an impediment to progress or a precondition for it?

Sometimes you need a healthy dose of ignorance in order to attempt those moon shots that may cause short term suffering, but pay off immensely in the long run.

Next Steps

Moon shots aren’t easy, so take baby steps when getting started. Build the habit of pursuing moon shots over time. Here’s what I’d recommend:

Step 1: Spend a few weeks gradually taking note of moon shots you’re neglecting. You don’t need to take action yet. Just build your awareness. Did you skip a worthwhile networking event because you were feeling tired? Take note. Has there been a business idea sitting in your desk drawer for 6 months? Take note.

Step 2: After a few weeks of taking note of possible moon shots, pick the most compelling one and begin taking action on it. Use tools like Trello and automate as much as possible so that you’ll be able to pursue this moon shot with greater ease.

Step 3: Repeat step 2 for the rest of your life. 😉


Photo Credit: Jim Davis

Free Online Tools to Increase Productivity

Having finally settled into a routine that keeps me constantly prepared for this semester’s never ending torrent of schedule conflicts, I can finally begin blogging consistently again. These past few weeks have made me realize that without the tools I use to keep myself productive and on top of my commitments, I would never have the free time to commit to blogging, go to the gym regularly, or maintain my social life. This post will detail all of the tools I use to keep myself productive. They are all internet-based and free. So without further ado:

1)  Gmail

Without Gmail, my life would be a lot more complicated. Gmail has a lot of easy-to-use filtering, labeling, and searching features that makes storing and finding e-mails a breeze. While some people never archive and leave all e-mails in the inbox, I use my inbox as a holder for unfinished tasks and projects. When I complete the task or project, I simply archive the e-mail and search for it later if I need to bring it up again. By contrast, my school offers a web mail account that allows for 50mb of storage. At that rate, I would have to delete e-mails frequently. By archiving them with Gmail’s 7gb of space, I never have to delete e-mails. And thank goodness I don’t. I can recall at least 10 times this past month where I’ve had to dig out old e-mails from last year.

I also use a combination of filters and labels to take e-mails sent from my school’s advising office, my fraternity, and from Residential Life (my current employer) and siphon them out of my inbox and into folders where I can look at them at my convenience. If they contain and task or project that I can’t address immediately, I move the e-mail back into my inbox and look at it later.

Here is a screen shot of my filters and labels.

Gmail Filters

2) Google Calendar

I promise this post won’t become a continual declaration of my love for Google. I just happen to use Google Calendar because that is what I am accustomed to. Your calendar of choice will suffice just fine. A reliable calendar system must be portable and easy to use. Google Calendar syncs with my iPod Touch effortlessly whenever I have access to WiFi (thankfully, my whole campus has WiFi). Therefore, I have my calendar everywhere as long as I have my iPod Touch on hand or a computer with internet access. It is also makes scheduling recurring commitments a breeze. However, I have many productive friends who swear by a physical calendar/planner. If that’s your style, by all means use that instead.

3) Remember the Milk

Before Remember the Milk (RTM), I was using notepad documents on my desktop as a way to maintain my Next Actions list, Project list, Waiting For list, and my Someday/Maybe list.

Side note: For those of you who are wondering what those lists are, I highly recommend checking out Getting Things Done: The Art of Stress-Free Productivity. Even if you don’t agree with everything in the book, there are many great points and a lot of tips that can help just about anyone increase their productivity while worrying less about whether or not their system has captured all of their commitments and tasks.

Remember the Milk is simply an online-based to-do list that has a great layout and is easy to use. A big plus is being able to sort your tasks by priority and due date. I also like being able to log in on any computer and be able to check my to-do list.  The only downsides to RTM are: 1) You cannot order your lists (you’re stuck with alphabetical order) and 2) The iPhone/iPod Touch app requires you to purchase a premium account and the website is not compatible with Safari on these devices. If you hate paying for anything and are devoted to your iPhone, Google Tasks gets the job done and can be accessed for free on the iPhone (although it’s not as pretty as RTM).

And again, if you’re a paper and pen person when it comes to lists, then by all means keep doing that.

4) Joe’s Goals

I happened to stumble upon this website (not actually using StumbleUpon) during a brainstorming session in which I discovered a problem with my productivity system. My short, intermediate, and long-term goals were ending up on the same to-do list as my day-to-day tasks. For example, my goals of eating a big salad every day and doing the daily brain training exercises at were ending up next to “File away Career Development Center activity sheets” and “Stop by academic advising office to change management concentration.” Although these goals were technically actions I wanted to take for that day, they had differing priorities, larger time commitments, and were ending up on the to-do list day after day in a never ending fashion. This constantly bloated up my to-do list and drained me of my sense of accomplishment. That’s where Joe’s Goals comes in.

Joe's Goals

As the screenshot above shows, Joe’s Goals allows you to easily track your goals on a daily basis. You assign a score (+1 or +2 or even -1 for negative habits you want to avoid) and at the end of the day you can see your score and which goals you accomplished that day. Joe’s Goals also comes with reporting features to view charts of your progress over longer periods of time. With Joe’s Goals, I no longer have bloat and clutter in my to-do list, yet I can easily track whether or not I am achieving my goals. If you would prefer to keep your goals off the internet, a well-made Excel sheet can accurately mimic the features of Joe’s Goals.

And there you have it! The free online tools I use to increase my productivity.