My wife and I wrote our own wedding vows. One of the biggest laugh lines in hers was, “I will support you in your many hobbies.”

It was well known among my family and friends that I was a serial dabbler. I experimented widely with interests in games like poker and chess, endurance races, writing projects, cooking, and all sorts of other things. The rate of new hobbies has slowed in recent years as I have settled in on activities that truly interest me and have abandoned those that haven’t.

In the interest of reflecting on my own experiences, here is a list of my nine favorite abandoned projects. (NOTE: Many of these projects still interest me, so I reserve the right to bring them back to life.) Continue reading “Looking Back on 9 Projects I’ve Abandoned (including this blog)” →

I’ve been playing chess on and off since middle school. The ancient Indian game of kings and queens has taught me a lot of lessons, but the most useful off the board has been the ability to predict how people will behave.

When I was first getting serious about chess, I found that one of the most useful exercises I could do to improve my game was replaying old grandmasters’ games. The key was that before every move I would think to myself, “What would I do in this situation? Why?” Then, I would see what the grandmaster would do and if it didn’t match up, I’d try and figure out why they made those moves.

The act of comparing my expected result with the actual result helped me refine my sense of how these players thought. When playing against people in real life, I would extend this exercise to notice how their body language was associated with their moves on the board. Were they sitting forward or back? One could be a sign of aggression and the other of hesitation. These simple observations helped me make crude models of where that person was and how they are likely to react to the way that I play. Continue reading “Learning Chess Taught me how to Predict People’s Behavior” →

About a year ago I was on a crowded New York City subway on my way back from work listening to The Art of Charm, when I heard something that broke me.

The guest said, “How can you be honest with other people when you aren’t even honest with yourself.” I started thinking about they ways in which I wasn’t being fully honest with myself and my thoughts landed on my calendar. My calendar was a reflection of the intended on doing, but was doing less of every day. I wasn’t exercising before work like it said I did. I wasn’t going to events after work like the app detailed. This misalignment was indicative of larger misalignments in my life, ways in which I was claiming to live one way and was actually living another.  Continue reading “How I Learned to Stop Bullshitting Myself” →

For the last handful of years, my wife and our close friends have gotten together to ring in the new year. We reflect on the year that has passed and share our thoughts for the upcoming year. For some people they take the form of a resolution. For the last few years, I’ve given up on the ideas of resolutions and started thinking in terms of yearly themes instead.

When I set resolutions, I would be like most people and lose focus on it as the year progressed. Then I got really good at achieving my resolutions, but I would have all this extra time and would lose focus on maintaining what I’ve gained.

Having themes has allowed me to think more broadly about how I’m viewing my life and keep me motivated when I achieve goals. Here have been my themes for the last few years (including this year and next): Continue reading “Six months ago I set out to be more intuitive. Here’s how it’s going. “ →

When I am anxious, sad, or emotional, those feelings concentrate in my stomach and emirate outward toward my chest. It feels like there is a giant corkscrew inside of me and it’s slowly turning, wrapping up my intestines like spaghetti around a fork. 

When I’m feeling really good, those feelings start in my fingertips and toes and grows like roots across my limbs. I can feel the ligaments and sinews in my arms and legs stretch with delight in being their full selves. 

When I don’t know how I feel, I drop into my body. It always knows. 

People don’t buy lemonade from kids because they are selling awesome lemonade. They buy it to support the cute kids as they learn a few things about how businesses work. 

For the majority of my life I’ve used a lemonade stand-style approach. Whenever I’ve asked people to support and idea, those people have mainly been family and friends. These are people who love me and want the best for me. The problem is that they will support me irrespective of the quality of my idea. As a result, I don’t have a great sense of which ideas are strong enough to stand on their own. 

In the free market, however, your growth depends on the quality of your idea (in general, anyway). 

As a result, I’ve decided to share this blog with people who might value following my journey for its own merit and not because they know me. For the foreseeable future, I won’t be sharing any of this on Facebook.  

Instead, I’ll share my posts with aligned subreddits on Reddit, on Twitter and on LinkedIn. 

As of last night, the United Kingdom has decided to leave the European Union. This decision will have a cascade of effects: the decline of the pound, Prime Minister David Cameron’s resignation, the potential for Scotland, Wales, and Northern Ireland to leave the United Kingdom, and the end of the European Union itself.

To this New Yorker, grumblings of secession have usually come from either Texas or Quebec. Both of these have been mostly punchlines, with any actual movement toward making them reality never really taking hold.

This UK move is surreal. Major cairn alert. Continue reading “What the Brexit Means to Millennials in New York City” →

In the book Choose Yourself, James Altucher makes the argument that the technology available today makes it so we do not have to wait until someone chooses us for us to do what we want. If you want a radio show, start a podcast. If you want to make a documentary, film it on your smartphone and put it on YouTube.

He also makes a more global appeal for you to not wait for other people to deem you ready. You can decide that yourself.

I’ve done a lot of things to put off choosing myself. I’ve applied for programs and other things so that other people can choose me. I’ve looked to others to validate the worthiness of me going in a different direction. None of it leading to much success.

I want to do something different. I want to fight for myself.

This summer, I’m going to take every Friday off from work and will work on to developing a product or service that solves a problem in the world. I’m going to bring in my friends and colleagues who have shown interest or capacity in the areas I’m working on. By the end of the summer, I intend on having a prototype that I have tested in the wild.

I’ll be using a design thinking structure to plan those eight weeks. It will be fun and hard and scary and I’m so excited.

I recognize that one of the reasons why Donald Trump has been so popular in the last year is that he goes against the widely accepted range of what society deems politically correct. Intellectually, I understand the appeal. When I think about transgender folks, for example, I get knotted up in a jumble of pronouns, gendered language, and misconceptions. As a result, I tend to be more trepidatious when speaking about transgender people and that hinders me from able to speak as I would about anyone else.

I’m much more comfortable talking about race. I’m an Afro-Caribbean Dominican-American who identifies as both black and Latino. I’ve had countless conversations with white folks who are confused about one or another part of that sentence. It’s part of life and I get it. Continue reading “Why I Hate the Word “Minority” to Refer to People of Color” →

Sometimes in life you’re just walking along and happen to come across a cairn. Other times, it takes a little work to uncover a cairn that is in front of you.

One of my favorite ways of uncovering cairns from other people is by asking them sharp questions. If you ask a low-quality question like, “How’s it going?” you’re going to get a low-quality answer. I’m always on the hunt for a good question.

A question that has always yielded me good fruit is “What’s the biggest question you are wrestling with right now?” Sometimes I have to expand the definition of this question if I think the person thinks I’m asking exclusively about work or any other specific domain. The point is to get people to open up about what is top of mind for them. Continue reading “What’s the Biggest Question you are Wrestling with?” →