Developing courage to lead

I recently realized that I have a problem with leadership, and it is an emotional one.

I have spent significant time studying leaders, reading about their lives, trying to understand what makes them leaders. Intellectually, I felt like I understood it. But emotionally I realized that I don’t believe in myself as a leader. Just talking about myself as a leader makes my heart race, my palms get a tingling sensation, and get nervous. 

That is what I’ve been working through over the past month. Even though I can recognize leadership in others, I struggle to call myself a leader. This is the case even when in the midst of leading a team. I see myself as someone who can gets things done. I can define a problem, find a path to move forward, and fix it. That’s what I’ve always done and that’s how I am comfortable contributing to teams.

As I look to the future, however, I know that my contribution to teams and society as a whole will be capped if I don’t develop my leadership. So I’ve been wondering, how exactly do I become a leader? Is there a checklist I can go through and come out at the other end as a leader? Do I wait until my manager tells me that I should lead a team (hint: it turns out, that’s not how leadership works)? 

In essence, in order to lead all I really need is: 

  1. A point of view, or vision, of how something should be
  2. Conviction & commitment to pursue that vision
  3. Courage to share it with others and compel them to follow

The only person preventing me from leading is me. Item number one on the list is not a problem, I have plenty of thoughts of how things should be. I can definitely argue a point. The second item may be an issue at times, there are few things I feel enough conviction about pursuing, so I can easily drop things. However, I don’t think that’s a big problem. The third element, however, is where I struggle the most. I am afraid to let others down, afraid of not looking smart, so I stop myself from trying to compel others to follow. Instead, I wait for others to lead the way. 

Addressing this issue is truly an emotional challenge. The prescription seems to be courage, practice, and resilience. 

I need to build up the courage to define a vision and share it while it is still not a done deal. I have to be willing to hear criticism and use that to grow. I need to distance my sense of personal worth from my work so that when others provide feedback on my work I don’t take it personally.

If I don’t do this, I will chicken out of sharing my thoughts until it is too late. I will continue to spend so much time thinking through the problem that the opportunity to lead will pass me by. I will become another one of those that hears their awesome idea from someone else and say: “Argh, I could have said that! That was my idea!” Too little too late. 

To be sure, most of this I already knew intellectually, even before this past month reflecting on it. So, what truly matters is what’s next. What am I going to do about it? 

  • I will carve out time to write down my vision & point on view on things I believe to be important. 
  • I will share this with others before I feel ready to do so. I will not keep a task to “polish X vision doc and share it once final” for weeks at a time. I will form a point of view and share before I have all the answers. By doing that, I will learn. 
  • I will not shy away when I get negative feedback on what I share. Instead, I will use that to learn, iterate, and keep refining my thinking. I will repeat that cycle as many times as necessary. 

By doing this, I hope to build up my courage. I know it will suck at first. As I write this, I feel a tingling sensation in my palms signaling nervousness. I really am afraid to let others down, and I will need to have the courage to risk letting others down in the short term for the long-term rewards of becoming the leader I know I can be. 

A note on self-awareness and the enneagram test

If you’ve heard of the enneagram test, I’m described eerily well as a self-preservation type three. Emotionally, if I’m not continuously achieving or succeeding, I feel like everything will come down crumbling around me. Continuous achievement is to the self-preservation three a requirement to prove that they deserve what they have. Any sort of failure, such as disappointing others, is felt very deeply as a threat to everything accomplished so far. 

I mention this because learning about my enneagram type was an unexpectedly emotional journey. More than once, I teared up as I read the hard truth about the fears that drive me. With that awareness, I can see how the fear of letting others down has been sabotaging my own learning and development as it relates to leadership. If you’re too afraid to look stupid, leading will become far more challenging. 

Business metrics vs. user value (why I quit Facebook)

I love data. A great dashboard with useful KPIs is beautiful and useful. If you haven’t yet, take the time to define and track success metrics for your product. It forces clarity and reflection of your goals.

Use data to prove or disprove your hypotheses. Use data to calibrate your efforts and see whether you’re on the right path. Use data to define bold goals for your product. But first, have a clear vision of what matters. Don’t lose sight of that vision.

A big pitfall is when we use easily measurable things, such as time on site or content engagement, to determine product success. It is tempting to do that since (1) it correlates with business value and (2) you can argue that it correlates with user satisfaction and value. While this can sometimes be true and work well, it can backfire as your product evolves.

I will use my experience with Facebook as a way to dive deeper into this.

Quitting Facebook while at a high

I quit Facebook right after my engagement with the platform was at a peak. I quit it because my engagement with it was at its peak.

I quit Facebook a bit over a year ago. I also quit Instagram, Twitter, and other social media. Why? They were optimizing their system to bring me back to their app and use it for longer periods of time and much more often.

I joined those social networks to connect with people. To play a role in my friend’s lives. I had invested 10+ years on Facebook, connecting with friends and sharing photos. But, I found myself spending more time browsing. Scrolling through the news feed. Clicking on articles. Watching videos that would autoplay on my news feed.

I would then see a friend’s update about a life milestone that I wasn’t present for.

I wondered, had I spent less time on Facebook and more time on the phone with that friend, would I have been present for that life milestone? Or maybe, just maybe, I meant to become friends with that person but they are really an acquaintance.

Why was I distracted by their lives?

I would come out of the app and wonder, is this helping me connect with friends or family? Am I happier?

The answer, 9 out of 10 times, was no. That’s a dismal rate of success.

The metrics trap

While Facebook had a mission to connect people, over time they started to optimize for behaviors that were driving their business success.

Well-intentioned Product Managers probably liked my engagement metrics. More time on the app, more engagement with news feed items, etc. These metrics would say that I must be happy with the product. However, while making me spend more time on site would always be better for their advertising revenue, after a certain threshold it is clear that spending more time on the site would be neutral to negative for my well-being. Also, the ‘what’ I did on the product matters.

I was spending more time on the site with an implicit goal of creating deeper connection with friends, family, neighbors, people I cared about. Instead, I was wasting the 30 minutes I could have spent on the phone or on video chat with one of those friends scrolling through a news feed increasingly cluttered with articles and videos.

I justified this as a way to understand other people better based on what they were sharing (articles, videos, etc.) I thought that those social networks would help me better understand the world around me. I had over 1800 connections on Facebook. I thought this would help me hear the diverse set of thoughts, feelings and opinions they had.

But, this was not true. I was hearing from the subset of friends whose opinions I was more likely to like. I was hearing less from those that I would more likely disagree with.

Those that would challenge my thinking were invisible to me. I was being shown perspectives that reassured me that I lived in a world that didn’t exist.

When that realization daunted on me with the 2016 election cycle, it was clear that my time on those platforms was being wasted. Success, as measured by feeling connected with others, was further away. Instead, the platform offered distraction. A fake sense of connection to a reality that didn’t exist.

Where did things go wrong?

Success as measured by metrics such as time on site and interaction events on the site, distracted the product from its mission. Those things that drive the businesses’ success through more advertising revenue were making it harder for me as a user to actually fulfill my desire to connect. Yet, I’m certain that many designers, engineers and product managers were running tests on the platform to increase those business metrics without questioning the long-term impact it would have on my satisfaction with the product.

Another way to view it, they didn’t question whether more and more engagement and time on site could be turning into too much of a good thing

In fact, I remember a video Facebook created recapping my past 1 year. It said that I had liked thousands of things over the past year. I did the math, I had liked on Facebook, on average, a few dozen things per day. That’s an outstanding number. Yet I felt emptier the more time I wasted on the platform.

Was I wrong to quit Facebook?

I requested my Facebook account to be deleted on April 8, 2017. I first did a ‘trial’ by deactivating the account. At first, I found myself mindlessly opening the Facebook app or navigating to on my computer. It was ingrained in my brain. After a few days that habit started to die down and my mind started to open up.

When I felt the need to connect, I would now send a friend a text and an invite to coffee or dinner. I called people a few times. Calling, on the phone, can still be a thing. It is amazing how much you can connect with someone by hearing their voice.

My friends didn’t forget about me. My social life didn’t get boring. In fact, now catching up with a friend is more special. We take the time to talk to each other about our lives without assuming the other person saw updates we generically posted for hundreds of people to see.

I hear less from many people. I probably haven’t heard from over 95% of my 1,800 Facebook friends. But, I’m happy to report that neither my life nor theirs is any worse off. I reclaimed the energy I spent “liking” those people’s posts or wondering when I would next catch up with them. I use that reclaimed energy to further my true connecting with people.

User vs. Business Goals

Whatever you do, remain focused on the user. Question your metrics and reassess what and how you measure them.

I may have emphasized in this post one product, but there are many other products guilty of this issue. Of optimizing for things that don’t add value to the user’s life or connect to the mission. Of forgetting to question whether the metric is still sufficient to determine whether users are happy. Watch users and see if behavior has changed to the point in which you need new measurements.

When thinking about your product, always remember to evaluate how it is that you’re adding value to your users. Be extremely careful when adding a new feature that will help you drive business objectives, but dilutes the value users get from their time spent on your product. Find ways to measure and focus on your users’ well-being.

Whatever you do, question your metrics and measurements. Don’t let them distract you from the reality of your user’s experience and the impact the product is having on them.

Be informed by data. Not driven by it.

Looking for a Mentor

My obsession with self-improvement leads me to reading a great books that inspire me to do something fantastic, motivate me to change my habits to better ones, or develop myself in completely different ways.  The only problem I have found is a lack of conversation about it.  I find it uniquely stimulating to share my thoughts and ideas about something I have learned, so that I can solidify my understanding of them and/or gain a new perspective.  However, it seems to me that self-improvement is not towards the top of the list of topics people talk about.  Same as with investments or finances, and many times relationships, I have encountered that many people tend to shy away from talking about important matters and instead focus on small talk about the weather, a new piece of technology, or the next vacation they will take.  Although I believe these are all fair topics of conversation, I have been yearning for the kind of conversation I rarely experience, from which I leave feeling empowered and with a thrilling sensation that I have found out about something that will help me improve my life and the life of those around me.

This lead me to continue pondering about the options I have.  Thankfully, we are blessed with living in the information age, in which most of the information you want to know about is just a few clicks away.  You can purchase great books in less than a minute, and have it delivered to your eReader or any other electronic device almost immediately.  You can also access fantastic online resources and learn just about any topic.  The two things that I lack from this approach, however, are direction and the opportunity for conversation.  A lack of these two makes the process of improving my life less efficient, hence why I decided to find mentors to help me.  Here is what I want to get out of my mentor or mentors.

Mentoring is a brain to pick, an ear to listen, and a push in the right direction.
– John Crosby


I could try to learn everything there is to know about calculus on my own (with all its derivatives and integrals), or I could choose to go to school instead and have a professor guide me through a curriculum of what he or she thinks is more appropriate for me to learn.  If I choose the right place to study for my purposes, the assumption is that the latter would yield me much better results in a much shorter period of time.  The guidance and mentorship of a professor would help solidify the right knowledge and help me apply it in the context of what matters to me.  This is the kind of direction I am seeking in a mentor.  Someone who can see where I am coming from, where I want to get to, and help me set a direction to close the gap.  This is what I refer to when asking for direction from a mentor.


I learn the best, and I assume most people do as well, when I have a chance to bounce my thoughts around with someone knowledgable responding to them and challenging them.  When I started learning Japanese in college I quickly realized that memorizing words before the quizzes was VERY challenging for me.  I would sit and read the list over and over, write the words over and over, and try to memorize them.  Inevitably, there would always be at least one word during the quiz that I would forget.  After a couple of weeks, however, I studied for one quiz with one of my classmates, and we quizzed each other out loud.  We also attempted to use the new words in the sentence structures we had learned, and that’s when it hit me, this wasn’t so difficult after all!  I realized that the easiest way for me to learn new vocabulary was to actually put it in context of conversation and actually attempt to use/understand it.  Having someone there to listen to me say my newly formed thoughts/sentences and respond to them solidified for me the knowledge I had just acquired.  It also gave me the opportunity to learn alternative ways of thinking about the new concepts I was learning from my classmate.  Now, if this approach was so effective to learn while in school, why am I not using it to learn about important life topics such as finances, spirituality and life in general?  It doesn’t sound like something wise.

Mentors come in all different shapes and forms, or so they say, and some of the most important advice I have received has been given to me over a casual meal or while chatting on the phone.  I have been lucky to find a few great mentors at different times in my life and am now looking forward to find one more (or a few) to fill in the gaps that I am currently experiencing.  Most of the mentors I have had, however, have been there for me without me having to go and find them.  I simply met them at my workplace, at school, or through a friend.  I never had to go out of my way to find a mentor, the relationships just grew organically.  So I am left to wonder, how do you go and find a mentor when you need it?  There’s only so much Oprah I can watch/read, and doing so only gives me the advice I seek, not the advice I may need and don’t know I need.

What do you think about the importance of mentors?  Where do you find mentors?  How have you found your mentors?

Lessons from 2010 and a few quotes to keep in mind

Last year, I wrote a rather lengthy post which I just re-read, and although I appreciate it very much because it brought alive some old memories with its prose, I will refrain from duplicating the effort by doing the same this year.  Instead, I want to take a few minutes to reflect upon some of the lessons 2010 offered me that I would like to remember throughout the year:

  1. Treasure friendships.  It is friends that give us the strength to continue moving forward when things get difficult.
  2. If it matters to you, give it your best.  No one will ever care for what you ‘could have’ done or achieved, but rather for what you actually did.  Make sure you have no regrets.
  3. When it is time, simply let go.  Sometimes we focus on not failing or try to hold on to someone/something and don’t realize that it’s hurting us more than it’s worth.
  4. Learn from others, but don’t blindly believe everything they say.  There are many wise people out there who can give you well-intended advice, but it’s not necessarily the best advice.  They can only see the world through their own eyes.  Learn from their perspective, but don’t get lost in someone else’s world.
  5. Follow your own advice. We often have great advice for our friends but are unable to follow our own advice when we need it the most.  Be honest with yourself.
  6. Keep a healthy body and mind.  Your body is the instrument you have to make a difference in this world, make sure it is in good shape to allow you to achieve your dreams. Meditate, eat well and exercise.
  7. Be optimistic and keep happiness simple.  It’s the only sustainable way to work and achieve your goals while continue to be happy and healthy.
  8. Be grateful for what you have. It will allow you to focus on the right things in life.
  9. Keep your goals in mind. Luck really is when opportunity meets preparation.  Make sure you are ready, or working towards being ready, for when the opportunity arises.
  10. Take a real interest in others. You will become a better person, and make the world a better place, if you genuinely care for others.

There have been many other lessons and great things I have come across this year, and I would like to finish off by sharing some quotes that I would want to read again in the near future.

“Don’t take yourself too seriously, no one else does”
– Regina Brett

“Whether you think you can or whether you think you can’t – you’re right.”
– Henry Ford

(Good fortune and happiness will come to the home of those who smile.)
– Japanese Proverb

“How people treat you is their karma, how you react is yours.”
– Wayne Dyer

“It is the simple things done over long periods of time that will give permanent and constant results.”
– T. Harv Eker

“Find what you’re going to be famous for. That’s not to say you should ignore your weaknesses. But make sure your strengths are aligned with what you want to be famous for – what your legacy will be.”

And, just to keep it real: “When you are complaining, you become a living, breathing “crap magnet.””
– T. Harv Eker

I hope this is a good summary of things I want to keep in mind in 2011.  I have many goals, but mostly I want to make sure I am on my path to do greater things each day.  The specific ways in which I will achieve this remain unknown, but I will let life surprise me with opportunities.  I will work on getting myself ready for when the opportunity arises.

The personal branding burden

Growing up, I thought it was weird how people labeled themselves. People felt entitled to give themselves titles.  Some would call themselves professionals. Others mature, goth or emo (bear with me, these were my teenager years). 

I never felt that boldness and confidence to belong to a category. I would write, but I was never a writer. I could practice martial arts, but I wasn’t really an athlete or a martial artist. 

Over time, I tried to join the ranks of the labeled, branded people. I started adopting labels like independent, mature, engineer, consultant. 

While some of this felt harmless, this labeling has come at a cost. You see, that labeling is only valid, I think, if others agree. Since inherently I’m just a human being living life, not a full time mature person, or an engineer 100% of the time, the more labels I try to live up to the more constrained I feel. 

I recently felt threatened when someone close to me suggested that I’m not mature.  My instinctual response was to prove my maturity. In the process, I realized that I have much maturing to do. Most importantly, I need the maturity to be comfortable enough with myself that other people’s opinions become irrelevant to my happiness. 

Instead of living a life trying to show that I’m mature or professional, I prefer to stick to the mindset of a child with no pre-defined notions of who I must be. What about returning to those blissful days in which playing with mud was all the rage because in my spur of the moment as a 5-year-old I decided that was fun? 

The more I define who I am based on labels, the less freedom I have to simply be.

Why do I write about this now? I feel discomfort deep inside me that tells me to reassess the notions I have about myself, the expectations that I’m trying to live up to based on labels adopted over time. Specifically, I need to abandon the dependency on other people believing certain things about me in order to be happy. 

Important Lessons I learned at MIT

Although my MIT education was full of a very diverse set of experiences, I wouldn’t say that everything I did was amazing or fantastic, or that I couldn’t have been successful without having learned certain things.  However, there are a few particular things I learned at MIT, inside and outside of the classroom, that have served me well and will hopefully continue to do so after graduation.  At least, I think that they will.  Here are a few of them:

1) There’s usually a lot more to a problem that can be initially appreciated. This is a lesson I learned inside and out of the classroom.  The thought that I understood all there was to a problem was one of the easiest way for me to fail.  Always keeping my mind open to other possibilities was one of the most important things I learned in college.

2) One of the biggest mistakes we make is to not make the most out of the resources we have. This was something difficult for me to learn.  I used to believe that there was some sort of value in being able to say “I did all this by myself,” but really, no one cares.  At the end of the day what matters is what has been achieved.  If you learned how to use Maxwell equations by yourself and someone else did it in half the time by going to office hours, there’s really nothing for you to be proud of, you should have made better use of the teaching assistants yourself.  Don’t get me wrong, I still think there is great value in doing things yourself, but only if that will allow you to acquire skills that you wouldn’t obtain otherwise.

3) Overcommitting is the easiest way to do a mediocre job at many things, and not feel good about your work, VERY often. After a good semester in college, I had this overcommitting syndrome, or however you may want to call it, and I tended to want to take on the world all by myself. I would want to do sports for 10+ hours a week, and work for another 10+ hours, while simultaneously undertaking a courseload that was expected to consume 60+ hours of my week.  I would then end up doing a mediocre job at everything, and up until today I feel bad about some of the decisions I made.  The only thing that I’m glad about is that I learned from those experiences.  I learned to do as much as I can do and feel proud of, but no more than that. If I can take on 5 things and be proud of none of them, I would rather do 1 to 3 and feel proud of everything I do.

4) There’s MUCH more to life than our surroundings. This is probably one of the most important lessons I learned.  Most of us tend to live in a bubble, in which we only think in terms of what is immediately around us.  It only takes a shift in our mindset to realize that those tormenting problems we have, the ones that consume our life and energy, are silly tiny details we have chosen to focus on and don’t compare to the blessings we have received in this life.  A simple trip somewhere else, or conversations with people outside the environment we are surrounded by, are usually enough to make me realize this truth. 99% of the time we take ourselves too seriously, and think that our problems are bigger than they truly are.  We need to relax, chill.

5) Balance can be tricky, and I’m not just talking about work-life balance. Many problems I encountered with regards to bringing balance to my life were not related to work.  I actually had more issues making time for myself, rather than committing all of my time for extracurriculars, academics, and friends.  I realized that having some time to unwind, clear up my thoughts, and simply reflect about life, was one of the most important things I learned to do during the past 4 years.

6) Most, if not all, of our limitations are self-imposed. Over and over I found myself making excuses as to why I didn’t achieve something, or performed at a certain level, just to find out later on that my excuses were vague, empty and meaningless.  There was someone out there facing worst circumstances and still pulling off the results I didn’t.  This taught me to re-evaluate myself, my actions, and thoughts.  Once I started removing obstacles from my head, just like magic they disappeared from my life.

Although there are many other things I have learned, this is the first installment of things that came to my mind as the most salient lessons I have learned.  I hope you enjoyed them.  If you happen to have any reaction, comment, idea, thought, etc.  please leave a comment.

Thank you, Omar


As a kid, I had a computer with a password I won’t forget, “success”.  I remember typing it every time I was going to do work, or just browse the internet.  Now, almost 10 years after I first typed this password, here I am contemplating the meaning of the word.

This year has been one of much reflection for me, and it will continue to be so.  I started the academic year back in September, and as a graduating senior it has been quite an interesting year.  The job hunting process has been quite humbling, I submitted my resumé to 14 positions in 8 different companies and got back 2 interview offers.  Those two interview offers resulted in a total of eight interviews, 2 rounds of 2 interviews with one company and 3 rounds with a total of 4 interviewers in the other. After all these interviews, it was up to them to decide if they would extend a job offer.

This past week I got my first response, it was a voicemail since I couldn’t pick up my phone during class, and there it went “…we just made our final decisions and unfortunately have decided to not continue along with you in this process.”

So there was a rejection, so close to the goal.  At first I was just numb, didn’t quite have a reaction.  Then it started to sink in and I realized just how difficult it was to accept defeat, yet at the same time I could only think of the thousands of people who have lost their jobs after having been working for many years, those who already have families that depend on them…

At the personal level, I am happy.  Looking back to the process I’ve gone through, it was quite an achievement to make it to the final round with both of the companies who offered me an interview, so I take some comfort in that.  Although it is still discouraging to hear that I was not considered best fit for the job, I eventually swallowed my pride.  There are many very qualified applicants out there, and I am sure that the people who got the job offer were very well fit for the position.

I am now waiting to hear back from my other final round interview, and getting ready to apply to other job opportunities.  I think this process of applying to jobs is a very interesting one, you keep promoting yourself over and over to people, and then just hope that you can convince the right people to allow you to start a career with them, and invest some money on you.

At the end of the day, however, how do you define success is a very personal matter, and so is failure.  So far in the game, I don’t feel like I have failed, but I am still debating if I can call my achievements so far ‘success’.  I am still stuck in the way of thinking that getting that job offer is the measure of my success during this process, but that doesn’t quite fit with my views since it always requires just a tad of luck to also get the job.

At night, when the world goes to sleep and I lie awake on my bed taking a look at my thoughts as they flow through my mind I realize… I succeed every day one way or the other. The little challenges that each day bring make me a stronger person, a more educated one and someone even more ready to face the difficulties that life presents us.  At the same time, I become someone who can appreciate the blessings I receive, and that is something that matters more to me than anything else.  So… am I succeeding?  I certainly think so, every single day.