Been a while since I shared something here – I thought this was extraordinarily entertaining and insightful. Too many of us are staring at our screens instead of seeing one another face to face these days.

It used to be that when people would complain about Mondays and having to go in to work, I’d chime in and add my $.02 of agreement, thinking it was just something you did. Everyone complains about Mondays, right?

But I didn’t feel it.

For years, I never really got what people were complaining about on Mondays. I mean sure, it’d be nice to not have to work on Monday, but that’s reality right? If you have to work, you’re going to have some version of a Monday and you’re going to have to start your workweek. Why complain?

Then, I experienced it for myself. I was at WebEx, had been there for ~2 years and I started to really dislike Monday mornings. I’d wake up, hit snooze 3 times, be late for my carpool and just really want to come up with a reason to skip work or, heaven forbid, to even call in sick.

“This isn’t like me”, I thought at the time. I’d never been one to call in sick or make up excuses. But it kept showing up, Monday after Monday.

So I thought about what was going on, at a deeper level, for a while. And I came to some conclusions:

1. Most people hate Mondays because they truly dislike their jobs and don’t do anything to change the situation
2. I like making things so much that I’d never really disliked my jobs, no matter how bad they were (for the record, working 100+ hours a week was nothing compared to the babysitting gig I had one summer)
3. I’d finally experienced what it was to dislike my job for the first time
4. I didn’t want to ever find myself in the “most people” camp

So I created my “Rule of Mondays”. Which goes like this:

 “If you find yourself waking up on the first day of your workweek, whatever day that may be, and you don’t want to go into work, listen to it. If it’s back for too many weeks in a row, change it.”*

For the past 8 years I’ve held that rule in my head and observed it fastidiously. It’s served me incredibly well. I knew when it was time to leave Yahoo! – that voice was there.

Damn it feels good to be an entrepreneur

Fortunately, I haven’t felt that way since 2008. Being on my own, working on things I want to work on with people I want to work with has been super fulfilling in a ton of ways, but the most important way is that every Monday comes with excitement.

I love the feeling of waking up on Monday, having an entire week of people’s time ahead of me to work with. I love the feeling of taking my first “official” day of the workweek and kicking the crap out of it.

I love knowing that every Monday is an opportunity to set the tone for myself and to accomplish more in one day than I think that I can. I strive to make Monday my longest and most productive day because it carries on into the rest.

Wasting opportunity is a terrible sin

Finally, I love Mondays because of this:

I’m fortunate enough to live in a country like the US and that I have the means to decide what I do and how I spend my time. I want to know that I’m making the most of that opportunity and every Monday is another chance to prove it to myself.

#GOMONDAYGO

*Some of you might recognize this as sounding very similar to Steve Jobs’ Stanford commencement speech. It’s one of the reasons that reading that resonated with me so very deeply – I’d just gone through this exercise in my own way

When I was a senior in high school, I was asked to speak to a group of high-achieving junior high school students who were participants in the CTY program of Johns Hopkins University. As per my usual with respect to public speaking, I did a lot of thinking and not a lot of writing. In fact, I still hadn’t settled upon my speaking topic when I showed up at the auditorium. I remember sitting at the table with the 3 other students who were slated to speak and feeling irresponsible, since I was still bullet pointing my speech out.

However, as I watched each of them nervously fret over their neatly-typed, single-spaced speeches and mouth the words to themselves with their last few prep minutes, I discovered that I knew what I really wanted to talk about: seeking risk and failure in your life.

I’ve often looked back on that speech because I was proud that I took the opportunity to use that moment to speak about what I actually believed. The idea that we don’t take enough risks is something I think about a lot and Morgan Spurlock artfully talked about it at TED this past March much more eloquently than I did back when I was 18. Check it out:

I’m always reading a lot, soaking in new information and trying to refine how I think about building, based upon what others are sharing about their experiences. Here’s some my recent favorite stuff:

• The most difficult CEO skill: Managing your own psychology: yup, Ben Horowitz is great at saying it exactly the right way. “I didn’t quit,” the answer of great CEOs who made it through.
• From GigaOm: Steve Blank on How Startups Can Take Advantage of The Bubble. I love how he starts out the video by saying that he thinks that entrepreneurs, at their heart, are artists. Resonates with me, for sure. 
• Mark Suster and Bill Gross talk about product development, strategy and many other things. Great stuff here for people who want to solve lots of problems and make progress on a regular basis.

Also, some music to enjoy:

• Tracks from Death Cab for Cutie’s forthcoming (and appropriately titled) album, “Codes and Keys”
• Codes And Keys (Gibbard Solo, Live in SF) by TwentyFourBit.com
• When The Sun Goes Down On Your Street (Gibbard Solo, Live in SF) by TwentyFourBit.com

Here we are, January 23rd, and I’m already receiving emails for invites to “Broken Resolutions” parties and hearing from friends that they’ve already cheated on their diet/workout/productivity plan.

*sigh*

I don’t do New Year’s Resolutions for myself (they don’t work for me), but for those of you who do and especially, for those of you who never keep them, it’s time to think about your goals & what they really mean to you.

First, if it’s something that you “resolve” to do – you should be serious about it right? I’m assuming that your Resolutions are actually serious, that you have resolved, mentally, that you want to follow them.

Secondly, if you’re resolved about something, you should have a plan of attack in order to execute. It’s very rare that any of us can just “resolve” to do something and then immediately do it.

Let’s say that you’ve resolved to change your eating habits in order to eat more vegetables. Actually acting on that includes changing your shopping lists, your cooking plans and recipes, your lunch ordering behavior and much more. This is true all of the time – really committing to making a change requires a plan of action and some realistic thinking.

To that end, I’d like to share two things for you to think about as we near the close of the first month of the year. The first is by way of Barry Ritholz’s blog, and speaks to the top mistakes people make in approaching behavioral change:

The second piece is something that might seem a bit tangential, at first, but that I believe should serve as a motivator in the pursuit of personal change.

This post on self-esteem and self-confidence makes this point:

“Self-confidence is the belief of believing in yourself; to believe that one is able to accomplish what one sets out to do, to overcome obstacles and challenges.”

So, if you made New Year’s Resolutions this year and have already discarded some or all of them, I suggest that you look at that choice and see it through the lens of achieving self-confidence. The mental impact of that abandonment is likely very poor. For many of you, this pattern of behavior weighs on you and continues to lead to the feeling that you can’t accomplish what you set out to do.

All is not lost, however. Through the simple act of revisiting your resolutions and actually creating a reasonable plan for change, you can reverse the cycle and set yourself on a path to creating greater self-confidence.

Go try it out .

If I asked you what motivates you, would you answer:

• Purpose
• Mastery
• Self-direction

???

This video would say that you should:

It’s 2 am on November 26th. Also, it marks the end of Thanksgiving.

I can’t sleep. I want to get shit done. I want to work. I want to bother all of the people I’m working on projects with. I want to wake them up and work through things we have on our to do list.

I feel hungry. Unfulfilled. Focused on the next step.

Every morning, I wake up half panicked, half excited. Every night, I have to force myself to go to bed. I can’t remember the last time I went to bed before 1 am and I don’t really care. 

This is what I’ve been working towards.

I remember reading an article years ago about Jay-Z. He was talking about what motivates him and he said that he had this insane competitive drive and that he fed it. He said that he’d be out at the clubs and Biggie’s song, “Juicy” would come on and he’d have to leave. He’d have to head to his studio and go work on his tracks, adding more, fixing them, writing more.

When I left Yahoo! over 2 years ago, this is where I hoped I’d get to. Work has become synonymous with what I think about and do naturally. Every extra step makes me move faster, want to push harder, go further. Every new person added to the portfolio of partners gives me more energy, more inspiration, more opportunity.

Opportunity. It’s everywhere

I’m fortunate to meet new people working on interesting problems every week. Some execute, others don’t. But they all have a chance. They’re all taking a chance. We are all builders and problem solvers, looking at a world full of problems and in need of solutions. When you view the world through the prism of optimism and sustainable self-motivation, you see how many things can be achieved.

What are you hungry for?

Every person has passions.

Every person daydreams.

What is it you’re daydreaming about?

There’s so much opportunity out there to take that passion and turn it into something you can work on all the time. So many ways to make a living by living. If you don’t feel hungry, but you want to, go fix it.

Leadership, philanthropy and confidence

Some interesting reading on being a leader, activism and social networks and the business of philanthropy, courtesy of the Gates Foundation. All of these things are worth printing out and sitting down to read and contemplate with your beverage of choice (mine was a nice cup or two of French Pressed coffee):

• Thoughts on being a leader and a thinker from a speech at West Point. He discusses the idea that true leadership means being able to think for yourself. Furthermore, he shares insights into learning how to think, concentrate and develop ideas. This piece delves deeply into what it means to turn off other ideas and noise and to tune into your own thoughts, ideas and your conception of yourself. It’s really elegant. I also really enjoyed a reference to Pomona in his talk:
  • It’s no accident that the word regiment is the root of the word regimentation. Surely you who have come here must be the ultimate conformists. Must be people who have bought in to the way things are and have no interest in changing it. Are not the kind of young people who think about the world, who ponder the big issues, who question authority. If you were, you would have gone to Amherst or Pomona. You’re at West Point to be told what to do and how to think.
• As if you didn’t already know how nerdy I am, here’s a confession: I look forward to reading some annual reports. I’m currently working on the Gates Foundation’s Annual Report. Beginning with a discussion of the efforts towards eradicating polio reminds me that there’s a lot of basic work that needs to be done globally in order to increase human standards of living.
• A website called “The Loop of Confidence” has a pretty solid post called Stop Thinking About What Other People Are Thinking – some simple and true tactics to employ if you find yourself more worried about everyone else’s thoughts. Love the pictures to illustrate the points

How are we using digital communications for our purposes?

I do a lot of thinking and reading (and rarely enough writing..) about how technology and communications are evolving together. As human communications increasingly become digitally enabled, the tools we have at our disposal often dictate our interactions and shape our social norms. Recently, Malcolm Gladwell wrote about social activism, Twitter, Facebook and his view. I found it interesting, but incomplete, so I’ve also provided some counterpoints to his piece that help me to round out my thinking about this topic a bit more:

• Gladwell kicked off the discussion by writing about about why Tweets and Facebook posts might increase low risk participation but they don’t increase meaningful (read: high risk) activism. To Gladwell, more involved actions are required for revolution and true activism.
• Henry Jenkins takes apart Gladwell’s piece in an interesting way, arguing that Gladwell is focusing on tools, as opposed to movements. He also points us to:
• Kevin Driscoll’s blog post, which is fascinating because he dissects Gladwell’s lack of understanding about the nuances of the technology utilized by Twitter and also corrects the historical records of the civil rights movement which Gladwell seeks to simplify. I found that he persuasively shifted the conversation to a focus on outcomes. Ultimately, distinctions between new and old participation make less sense than an understanding of how to utilize the networks and tools (in his phrasing, taking advantage of the current cultural and technological circumstances ) of today to push new social changes. Sounds much more reasonable to me.

Ultimately, I think that the technology of today facilitates human communications. Increasingly, the products shape our communications and expectations, which is a place where I think a lot of us get into trouble (I.E. expecting instantaneous responses, misinterpreting text-based messages, relying upon the device as an intermediary that softens and makes tough conversations easier..) but that’s not something we can stop. Rather, the new tools should be appreciated and understood and used as just that, tools, for our communications purposes. If we can organize more people to take massive action, great. If we can just use them to increase awareness, fine. It’s up to us to figure out what works for our purposes, not to complain about what’s changing and different.

As an unabashed math nerd, I’ve loved being 32, because it was a very elegant number: 2⁵. *sigh* that all ends today, as I turn 33 . Oh well, I suppose I’ll have to wait a while for the next mathematically pretty number: 6²

Over the past month or so, my friends Greg, Jenni and Zain have taken to tweeting and retweeting things that I say and adding the hashtag #whoisrobiganguly, which I think is pretty hilarious AND flattering. It feeds into my natural introspective side, thinking deeply about who I am and what I believe. So, on my 33rd birthday, I’m going to indulge in a bit of self-reflection by sharing some things that I think and some things that I’ve written. A blog post full of #whoisrobiganguly goodness, if you will .

1. Stay positive. It’s easier to complain and be snarky but being positive and figuring out how to have and make smiles is a lifelong skill.
2. Don’t just dream, do. I haven’t figured out this entrepreneurial gig by any means, but I take more action in my life now than ever before. I love that.
3. Listen, listen, listen. Listen until your ears bleed and your patience has been exhausted. Then listen some more.
4. A sunny day is not to be wasted
5. Get used to people changing. Embrace it. Assess what it means for yourself.
6. Reading is an investment in yourself
7. In this age of digital overload, you can stand out with the people who matter. See them in person. Call them. Write them letters and meaningful emails. Give them your time.
8. Go Fail Yourself
9. Communication is never perfect. Your words are never interpreted exactly as you intend them. Especially when written.
10. The shorter the message, the more possibility there is for misinterpretation.
11. Find your passions and feed them
12. Look people in the eye
13. All honesty stems from honesty with yourself
14. Make being motivated your job, it will sustain you no matter what: http://www.wethechange.com/top-31-motivation-hacks/
15. Ask questions. Real questions. Make people think.
16. Your happiness is up to you. How you perceive your life and how you remember it are choices you should be making on a regular basis.
17. Learn how to break and build habits. These are your weapons for change.
18. Figure out which of your friends are willing to be brutally honest with you and give them free reign. Encourage their honesty, appreciate it and listen to it.
19. Prove yourself wrong. I never knew what I could do until I questioned my own mental limits.
20. Practice the things you want to be good at. You won’t be good right away.
21. Complaining only helps if you intend to do something about it
22. Yes We Can was/is more than just a campaign slogan. It’s simple truth.
23. Eat less
24. Drink more water
25. It’s a marathon, not a sprint
26. Expect the world of yourself. Don’t apply that to anyone else
27. Loyalty is not mindless
28. Invest in your values and priorities – be thoughtful about who and what gets your time, energy and money.
29. Productivity stands out
30. Focus is one of our greatest abilities. Focus your time and energy on the things that are important to you.
31. Don’t give expecting to receive. Give because you truly want to.
32. When you think you can’t go any further, take an extra step. It’s always there in you.
33. See more live performances. Recordings help give exposure to excellent art, but seeing a band, a painting, a sculpture in person is always more impactful and inspiring. Case in point: at last night’s Arcade Fire show the entire crowd got into the song with the band. I tried to capture a bit of it on video, but experiencing it live is wholly different.

Who Am I?

It’s a question I think about on a regular basis. Before going to Pomona, I didn’t think about it very much. More importantly, before going to Pomona, I hadn’t really taken ownership of the answer to that question.

Maybe it was being a PPE major. Maybe it was sitting through Professor Hurley’s sweltering classes when it was 90 degrees out. Maybe it was all the drunken pontificating that Sagehens tend to engage in around one another. Maybe it was just me growing up.

Perhaps all of that contributed to me seeing the world and my future differently. Or maybe none of it did. 

What I know is this: when I graduated from Pomona, I was a significantly different person than I was 4 years prior. More self-aware and focused on figuring out what I really valued and how I wanted to spend my time.

My actions say a lot about me

In thinking about who I am, I think about how I’m spending the key resources I have at my disposal. I believe that how I allocate these resources says a lot about me and what I prioritize. For example, I tend to focus on 3 key elements of my life:

• My time
• My emotions and care
• My money

I like to focus on ensuring that these 3 things are underlining my values.

How much are my values worth to

me?

We all have to decide what we put behind the things that we value. I’ve realized, over time, that I routinely experience a perception gap between what I say that I value and what I actually value, as measured by how I’m allocating my resources. For me, identifying that gap is a big benefit to thinking hard about what my actions say about me. While I’d love to say that I find my actions and values in perfect alignment, constantly, the reality is that it’s a far more difficult process. I don’t have, nor will I ever achieve, perfect balance.  I’ve come to accept that this is a process and that the important underlying component is progress. Progress towards more accurate alignment of my values and my actions is increasingly how I measure myself.

I value education, particularly the kind provided by Pomona

To me, the surest way to help out our communities is to make them as self-sufficient as possible. Education’s one of the best and most sustainable methods of creating human self-sufficiency. One of the greatest things that any person can do to improve their lot in life is to actively educate themselves on a regular basis.

A Pomona education is a tiny piece of the education system, but it’s a piece that I really believe in. I believe that the resources, the faculty, the philosophy, the size and the myriad other things that make Pomona Pomona are excellent at preparing college students for a lifetime of self-education and decision-making. As I look around at other schools, I see that Pomona’s an increasingly rare institution: expanding financial aid, increasing investments in facilities and faculty and continuing to make long-term decisions in an increasingly short-term oriented world.

I loved my 4 years in Claremont, met some of my best friends and it’s important to me that Pomona is around for a long, long time, offering future students the same or better than what I received while I was a student. For me, giving to Pomona through the donation of some money and some of my time is the least I can do to support something that means so much to me.

10 years in – now I invest in Pomona

This year, I made what is, for me, a significant donation. Significance is a very personal measure and I wanted to be very thoughtful about what I decided to do for my 10th reunion. It was something that made me sit down, think really hard about where I put my money and time and realize that if I was serious about what Pomona and education means to me, I had to be serious about investing in it.

In attempting to more properly align my actions and values I’ve come to view donating to Pomona as a form of investment, rather than a bill. My annual donations to Pomona are investments in myself and my values.

If you feel the same way about Pomona, I urge you to think about your donation to Pomona the same way. Whether you’re giving $5, $47 or something else, if you valued what you had at Pomona and you want to see that available for future generations of students, INVEST in Pomona, don’t just give to it.

www.pomona.edu/give