Merengue music and heavy subwoofer thumps announce a passing car outside my window. It turns the corner, and the music fades, leaving screaming car alarms in its wake. As the 2am Inwood chorus wails, I sit at my computer and grin.

Damn. I love this neighborhood.

Inwood is full of its peculiarities. In many ways it reminds me of a fading, but still brilliant, photograph. The churning population of Spanish-only Dominican immigrants, Irish, and general New Yorker-types convey the private and exciting vivacity of Inwood. And yet, rapid development and upwardly mobile housing prices promise to push out much of this area’s immigrant population.

In the photograph metaphor, I am a sun ray. As a 20-year-old white student of Columbia University-albeit on temporary academic leave-my presence adds to the area’s richness. I am incorporated into the hodgepodge swirl of churning ethnicities, cultures, occupations and life stories. In what is an overwhelmingly Hispanic neighborhood, I live with a recently immigrated Russian, Dimitri, who has been in the US for only 8 years. At 3am on Monday nights, I sip beers with Inwood-lifers in Irish bars. As a white kid from Washington State attending an Ivy League university while running an Internet start-up, I feel at home precisely because I am an anomaly. I am a puzzle piece — unique in shape, but homogenous in that I am different from those around me. I fit. My presence is another reminder of how fundamentally “New York” our deviations are.

Yet, the same sun rays that elucidate a photograph also yellow and fade it. Though my presence adds to the eclectic mix of this neighborhood, it is also indicative of a new tide of gentrification. East of Broadway is becoming safe — almost too safe. Across the street from my apartment, new trendy restaurants are opening among the sweaty pizza houses and “$3.99 comida con bebido” joints.

A large, but incredibly shy man named Marty tells me in the Linny Bar (an Irish hang out), “Things are happening here, there’s a lot of building that’s going to be done in the next couple of years. Unfortunately, I’m not allowed to talk about it.” Marty should know. As the president of the Inwood community board (overseeing more people than any of Manhattan’s other 11 CBs), he hears about and approves most of the development that takes place in the neighborhood.

Clad in a button-up shirt and tie, Marty looks out-of-place at Linny as he sips his Coors light from a glass. A jolly-and drunk-man lumbers from across the bar and slaps him on the back spilling some of the drink: “I’d campaign for you to get another term if I wasn’t so worried my record would hurt you more than it’d help!”

Marty’s good friend, Mike, looks at me and tells me, “You should have been here two months ago. This place was a real dive before she told the owner to get candles and the couch [he gestures at the bartender].”

I tell Mike what I pay for my apartment. “Six-hundred dollars a month?” he roars “Two years ago that would have been an absurd amount for anywhere in this neighborhood!”

Change is nothing new to Inwood-or to anywhere in New York-but I can’t help but feel that this transition is different. Inwood is not being bequeathed to a new wave of immigrants. Rather, it is being handed to a different economic class of young professionals looking to live in Manhattan without paying weighty bills. Inwood’s increasing safety and easy access to downtown (the A express whisks passengers to 42nd St. in under half-an-hour) makes the area appealing.

I look out my window and am filled with a nostalgic sentiment that I don’t yet deserve to have. Will economic development necessarily come at expense of the neighborhood’s personality or will the coming changes add to Inwood’s vibrancy?

Another car rolls past the apartment. This time the car alarms stay silent. In their stead I hear the softer hum of Billy Joel’s Piano Man. I watch as the taillights dip around the corner and fade with the music.

Written Sept 30, 2006

Hey. You. What do you want to do with your life?

How are you going to get there?

Where are you going to spend your free time when you’re not working?

How do you answer big open-ended questions like those for yourself?

Life altering decisions are super stressful. Our puny little brains are bad at comparing lots of disparate options, especially if the options we choose will have a major impact on our lives. Thus, a common approach to answering big life questions looks something like this:

1. Come up with an option (“I could be a doctor”)
2. Imagine a world in which you’ve achieved that option (“I’d be helping people. I’d be making money!”)
3. Get super excited about that option for a while
4. Get dissuaded (“wow, becoming a doctor means being in school until I’m 35”) or distracted (“actually, being a lawyer would also be interesting and might be faster!”)
5. Repeat with a different option (sometimes within the same day, or hour)
6. Get exhausted and feel defeated
7. If the decision is time sensitive, make a hasty final decision as time, money, and options diminish

Luckily there’s a better approach. I call it the life figurer-outer. Check it out here.

High level, the life figurer-outer lets you quickly and easily come up with an expected value (think: utilitarian score) for anything in your life. It provides a rational, low stress way to compare options, focus on the most promising paths for achieving your goals, eliminate the worst, and otherwise make better decisions.

I think you’ll get it pretty quickly, so I’ll spare you the details. But, here’s how you use it:

1. List out every option, or bucket of options, you’re considering. Don’t worry if options are dramatically different (become a famous podcaster vs. sell woodwork on Etsy). It’s important to get everything out of your head and into the list.
2. Define goals you think are important. You’ll likely get some value out of the simple act of thinking through what you value and how much. In the linked spreadsheet, I use short and long term career satisfaction, short and long term financial compensation, and life fit (e.g. you have a relationship in SF but the job is in NYC). But, those categories might be different for you. For instance, cost and sense of purpose might matter most to a retired person deciding how to spend his or her time. You’ll also need to head over to the assumptions tab and change the “weighting” for your various goals. If you’re just starting your career, for instance, you might value long term fulfillment 10X more than short term compensation.
3. Rate each option 0–5 in terms of how it fulfills each goal. Do this quickly and don’t get too stressed out about whether something ranks 3 or 4. It doesn’t matter and you can tweak scores later. Also, it’s your list, so you can break from 0–5 in the case of a true outlier.
4. Define payoff probability for each option. You might want to be a movie-star or start a public company but know that the realistic odds of that happening are low. Stick with standard increments so you don’t get hung up (I use 100%, 90%, 75%, 50%, 25%, 10%, 5%, 1%, 0.1%, etc.).
5. Sort and prioritize. You’re done with the hard part! Sort your options by their expected value score and see what rises to the top. Do the results match intuition? If not, maybe you need to tweak some of the values or rethink what you’re prioritizing.
6. Action. The most important step is, of course, making decisions and acting on them. Pick the option(s) you will pursue. Just as importantly, stop thinking about the ones you will not. You now know why you are doing what you are doing and why you’ve de-prioritized everything else. That understanding should enable you to move forward confidently, and with the focus and execution you’ll need to achieve your goals.

A Real World Example

The life figurer-outer has often helped me to strategize around my own career. A while ago, I decided to wind down a startup and was faced with figuring out what to do next. My options were varied. Several friends wanted to explore business ideas together; these offered the potential for high payoff but mostly involved high risk. I had a blossoming interest in VC. I had an offer to run product for a company that was willing to pay me a very high salary, but had potential cultural issues. Another company offered the opportunity to work with a killer team in a space I loved, but at lower compensation and with a smaller title. I also had additional final round interviews lined up. And then there were wildcard options: travel and freelance or start a cashflow business.

The decision felt overwhelming since I could imagine myself being happy doing many things. So I decided to assess my options with the trusty ol’ life figurer-outer.

I started by listing out all the options that were consuming mindshare.

Next, I plugged in scores. This was a quick exercise. I spent maybe 2 seconds per score. To determine a satisfaction score, I’d imagine each option and think about how it made me feel. I best guessed compensation scores. And then I set life fit score based on whether the job would require me to move.

Next, I decided how important each value was to me. What I realized is that I cared about the long term far more than I cared about the short term. Additionally, life fit wasn’t a big deal for me. I was single and willing to move for the right opportunity.

I now had all the information I needed to see my ranking. I sorted my list by highest to lowest expected value.

The results immediately made a few things clear. Most of the things I was thinking about were distractions and needed to be dropped. It was not the right time to start a business, freelance, or explore my fledgling interest in VC; the expected value of each was low. I also made the decision to cancel some outstanding interviews because my existing offers were superior.

I could now focus on my real decision: take the highly-compensated and local VP Product position or the lower compensated but more satisfying position that required me to move.

The first option sounded hard to pass up. But, based on what I said I valued, the life figurer-outer suggested I go with the latter. That job was Postmates.

The whole thing took 5 minutes start to finish.

I’ve never looked back.

In “Tinder and the Dawn of the Dating Apocalypse”, a Vanity Fair article that’s been circling the internet, Nancy Jo Sales portrays an emerging dystopian world in which Tinder and a slew of new dating apps have facilitated the collapse of traditional dating. The basic premise: Tinder & similar apps (Hinge, Happn, Bumble, etc.) provide a plentiful supply of women and men available almost on demand (think: Uber for sex). An abundant supply of casual sex partners creates the perception that there’s always something better and has eliminated traditional incentives to settle down. The article looks forward to a world permanently transformed by Tinder, which has acted like a “wayward meteor on the now dinosaur-like rituals of courtship.” It asks the question: where do we go from here?

While a compelling and well-written period piece, the article — or at least the initial response to its publication — risks falling into the error of projecting a current short term trend to infinity, while ignoring counterbalancing factors. Is dating different today as a result of dating apps? Undoubtedly. But does that mean romance or the need for companionship that extends beyond a one night stand are dead? No.

Good matchmaking is notoriously complicated and, even historically, often outsourced. Human matchmakers have taken a variety of forms across cultures, including family or formal matchmaker roles. Increasingly, and since even before the internet’s invention in 1983, the need has been addressed by computers (fun fact: computer dating is referenced prominently in the 1971 hit Harold and Maude).

The challenges of adult dating helped push sites like OKCupid, Match.com, and eHarmony into the common lexicon. Such sites were highly focused on compatibility, which was achieved through cumbersome experiences involving encyclopedia-esque profiles and long quizzes that could take hours to complete. The overwhelming hurdles to online dating reinforced stigmas around online dating as desperate, despite its functional near-necessity for many looking to date. Over time, however, success stories and an increasing population finding utility out of such services helped make internet dating socially acceptable.

The rise of the smart-phone initially offered few large scale success stories amongst online dating’s major players. Complex & time-intensive profile creation (and browsing) simply does not translate well to the medium, a lesson that’s been learned by many an industry. What thrives: bite-sized experiences & simplicity, which Tinder achieved through 1-click profile creation (Facebook) and by stripping out essentially all profile content besides pictures. Easy setup and some strong early marketing to highly desirable segments of the population made dating, something people previously did despite the friction & stigma, accessible and socially acceptable. The result was that many, many more people started online dating. Tinder became a beacon, and an explosion of fast-follow hot-or-not & swipe apps followed closely behind while traditional players pivoted their experiences to incorporate swiping.

The problem with Tinder-style simplicity, however, is it leaves users with one major criteria upon which to evaluate their compatibility with others: are they sexually attractive? The result: the most prominent dating apps are really good for finding partners who mutually find each others’ pictures sexually attractive, but poor at evaluating basically anything else except as explicitly filtered as part of the premise of the app (e.g. Hinge’s friends of friends, The League’s elite backgrounds).

In other words: the Vanity Fair article observes a trend (explosion of dating apps that people are sometimes more likely to use for sex than for actual dating). That trend is the result of structural realities that are specific to the first wave of mobile dating apps to become popular (Tinder and lookalikes). Those apps became popular because of structural requirements of the medium (simplicity & social acceptability) and are largely fast followers (down to the exact swipe gesture) of a first mover which also happened to be highly superficial. The result is almost every dating app out there is simple (necessary) and based primarily on looks (not necessary).

People still want companionship. It is a core human need, not a circumstance of history. The existing tools are just designed for something else.

At Teased, we aim to combine the simplicity that’s enabled apps like Tinder to thrive, with an experience that helps evaluate whether you’ll actually enjoy someone’s company.

Ultimately we believe we are where online dating is headed.

Tinder and Tinder-style apps will continue to have a place for the foreseeable future and their prominence corresponds with genuine changes to the way people choose to date as well as attitudes around sexuality generally. Yet, apocalypse implies an endpoint of sorts, and that is not what is going on. Rather, a solution to one set of problems has overshadowed another. The pendulum has swung far in one direction. It will swing back.