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Friday, May 30, 2014

What I’ve learned in my first year as a college dropout

One year ago, I took a leave of absence from Pomona College, moved to the Bay Area, and started working full time on Clef.
At the time, Clef was just a product — no one was really using it. One year later, we power logins on over 4,500 sites, protect more than $1 billion dollars in assets, and help thousands of people all over the world stop worrying about their security and start spending time on the things they care about. We haven’t killed passwords yet, but we’re getting closer.
But, those are just the highlights of what’s otherwise been the most challenging year of my life. Along the way, I’ve messed up, and learned, more in a single year than I had in the previous nineteen (and a half). In this essay, I attempt to condense nine of those lessons— from least to most important—in the hope that they’ll be useful to someone else.

It’s easy to furnish a house for free

For the first summer out of school, my co-founders and I subleased a fully furnished apartment in San Francisco. Three months in, when we moved from SF to Oakland in 12 hours, furnishings were not at the top of our mind. We started the fall with a completely empty house, I slept in a sleeping bag for weeks.
After a few looks at, the Salvation Army, and various sections of Craiglist, we quickly realized that it would cost us thousands of dollars to buy the basic supplies for a three bedroom house. With little to no available, this was out of the question.
Beds, chairs, tables, couches, desks, dressers, napkins, cups, mugs, spoons, forks, knives, plates, bowls, pots, pans…it gets expensive.
After digging a little deeper, I realized that I didn’t have to buy all of those things — I could get them for free. One weekend of determined searching later and I’d furnished our whole house from the Craigslist free section.

$40,000 is enough for me to live very well

When I left school to go full time on Clef, I was privileged enough to enter the Real World with no debt or financial responsibility (and healthcare through my parents) — I needed to support myself and that was it. Still, I was concerned whether I would be able to do that using only my savings and a small salary from Clef.
A year later, with my routines well refined, I spend around $1,700 per month on all of my living costs. I cook most of my meals, don’t buy new things (technology, clothes), rarely go out in a way that costs money, and don’t save anything. While certainly a non-trivial amount of money, for living in the Bay Area, I’m relatively pleased with only needing $20,000 post-taxes to sustain myself.
As I’ve considered other things that I would like, I’ve realized that with $30,000 a year post-taxes (or an additional $800 per month), I could live a much improved version of my life. $800 extra per month is a lot.
As we grow the company, and I continue to have no financial responsibilities beyond myself, a $40,000 a year salary (coming out to ~$30,000 post-taxes) is what I’ll work towards — and I’ll keep working to make that amount of money seem lavish.

Writing online is really powerful.

The summer of 2012 was the first time I ever took writing online seriously. During my time as a hackNY fellow, I wrote a blog post every day — in 3 months, I wrote some 70+ posts chronicling my first ever exploits in the tech industry. Even though many of those thoughts were misguided (and poorly written), they gave me a taste of how powerful writing online could be — during the summer, more than fifty thousand people read something I wrote at one point or another.
In the last year, as I’ve started writing again on my blog and on Medium, I’ve been reminded of that power.
The amazing thing about writing and publishing online is the potential reach from a single piece of content. It takes time, thought, and energy to refine thoughts into writing, but when that content is well received, that effort can be multiplied and returned hundreds of times over by readers.
It feels unreal — that one can put a single thing into the universe and hundreds of thousands of people can react and respond to it.

Dropping out is not like finishing school

Living and working with two individuals who did finish college at Pomona, I’ve had the unique ability to compare my life as a dropout to their lives as graduates. When I left school, I imagined that it would feel exactly the same — that leaving early would be just like finishing on time. As my first year post-college comes to a close, I’m realizing that while externally things look similar, internally I feel very different.
I describe this feeling to my friends at school by telling them that I’ve discovered the key to never growing old: taking a leave of absence from college.
With the potential for two more years in my back pocket, it feels to me as though I’m on an indefinite break. This break starts with Clef, and could take me through countless other stages of life, but at any point I can decide to end it and get back on the track of “My Future” by finishing college.
I’m scared of buying furniture because I know it’ll never survive college. I won’t get a pet for the same reason. Relationships I make tend to feel temporary because I know I won’t live in one place for long. The idea of finding a long-term partner, settling into a home, or having kids is a fairytale for a future me.
I feel like I’m not living the Rest Of My Life just yet, a liberating and isolating, empowering and limiting outlook.

I can tell in 5 minutes if I will like someone

Growing up, and all through college, social structures were built into my everyday life. Between classes, dorms, sports, and clubs, I was constantly surrounded by peers that shared my interests and values.
In the Real World, I haven’t had the same experience — I need to work hard to meet new people, and when I do, I often spend time with people that I don’t exactly care for.
As I’ve done more of this sort of socializing, I’ve realized that in 5 minutes I can get a strong feeling for whether the person I’m talking to is someone I want to spend more time with. It’s a combination of a few things: where our initial conversation naturally flows, their body language, the way we interact, and just a feel.
While efficient, I’m not sure how I feel about this revelation. At first glance, it seems great, but as I’ve thought more about it, I’m worried that in this initial judgement I’m likely biased towards certain types of people.
This bias has the potential to create a filter bubble where I surround myself with a homogenous group of people because I likely have a large number of initial false negatives.
Finding a balance here is something I’m working on now.

Discussing what I do is never easy

At home, at school, at social events, at dinner, at anywhere, the first question I’m always asked is “so, what do you do?” After a year of answering, I still haven’t found a response that pleases the asker and makes me feel good.
The first strategy I went with was the canned response (one explainer, three progress bullet points).
So, what do you do?
I work at a company called Clef in Oakland that’s building a replacement for passwords. With Clef, you just hold you phone up to your computer and you’re logged in — it’s easier and more secure.
How’s it going?
Awesome! We just crossed 4,500 sites using Clef, the New York Times called the technology “magical,” and we’re shipping [awesome new feature] in a week.
For quick conversations with strangers, this is tolerable (though boring), but when interacting with people that I care about (friends and family), it often feels disingenuous. With this quick response, I paint a rosy picture of success — leaving out all of the painful stuff that’s actually going on in the background.
The next strategy I’ve tried is the coy response.
So, what do you do?
I work in Oakland, what about you?
Oh that’s cool, so what do you do?
I’m an engineer.
Awesome! What kind of engineering do you do?
…on and on and on…
Occasionally, being coy allows me to quickly move on to other topics of conversation, but often it just leads to my conversation partner slowly pulling the original, canned response out of me. In the end, I’m often perceived as disinterested or unexcited about the company I run and left worn out by the questions.
With both canned and coy responses, I’m left feeling bad.
My relationship with this question embodies a constant struggle I have as the founder of a small startup: how do I handle the fact that every conversation I have about Clef has the potential to have a serious impact on its future.
Imagine we’re having a conversation about Clef.
In the span of 2 minutes, I tell you every good thing that has happened to us in the last 6 months. I drop easily memorable snippets: “we just crossed 4,500 sites” and “we were featured in the NYTimes.” I give off an air of extreme confidence and excitement. I bring you into my fantasy where Clef is a wild success and make you feel the highs that I really do feel. When you walk away from that conversation, you have a positive perception of the company I run. The next time your friend says, “have you heard of Clef,” you’ll remember, and share, my sound bytes and excitement.
Now, imagine our conversation goes a different way.
Because I had a hard day at work, rather than telling you about the recent successes we’ve had, I tell you about the horrible mistake I made or the deal we lost. I tell you how every day I feel like shit and I look for comfort from a friend who I trust. When we walk away from that conversation, yes I may feel comforted, but your perception of Clef becomes one of struggle. Yes, you support me, and no, you won’t go tell everyone about all the bad things, but the next time your friend asks “have you heard of Clef,” you’ll quietly say “oh yeah, my friend works there” and leave it at that.
Given how many seemingly arbitrary decisions I’ve seen made based entirely on perception and “feel,” it feels idiotic to do anything but constantly promote an image of positivity. But, from experiencing this positivity trap, I know that it’s emotionally taxing to keep the facade up when the reality of my day-to-day is nowhere near as pretty a picture.
What do you do?

Age is all context

When I moved to the Bay Area, the first people I really spent a considerable amount of time with were my older brother’s friends. Introduced to them as a little brother, I constantly felt younger, and slightly out of place. I love them (and I think they love me too), but for me, our friendship was always partially defined by my younger age.
As I branched out to new friends, I’ve realized that my age, and the way I feel age-wise relative to the people I’m spending time with, is entirely defined by our shared past context.
If a new friend knows me from high school, college, or through someone else, I often feel isolated by the fact that I’m younger than them. If we’re meeting for the first time through a shared interest or experience, age rarely comes up and I feel like part of the crowd.
A year after settling in, my closest friends, all from fresh contexts, are the same age, or older, than my first friends, but I rarely feel the difference.

Companionship is better than commiseration

Sad as it is, during the hardest times in the last year, I’ve often looked for someone to commiserate with. Someone to listen to me whine about the hard thing I’m going through. Someone to validate that the horribleness I’m feeling is normaland assure me that in one day or one week or one month things will be better.
As I’ve become more attuned to what makes me happy, I’ve realized that while commiseration can be effective, companionship serves me much better.
I first picked up on this after I’d taken a few breaks from work: the mountains, the beach, back to college.
In every place but Pomona, I found myself completely consumed by work; fretting about the things I needed to be doing (and the things that weren’t getting done). In contrast, on my trips to college, I was able to let go of everything (and return back to work with a clearer mind).
After observing this trend a few times, I started trying to pick apart why this was: the weather in Southern California? the academic atmosphere? Gradually, I realized that I was able to relax because I was surrounded by loving friends who were keeping me constantly engaged in other, less worrisome, things—the best kind of companions.
The worst part about being in a rut is that all I can think about is that rut. Every second of every day, I’m worrying about what I can be doing to get out of the rut. It consumes me. Thus far, finding companionship is the only thing I’ve found that can break me out of this. Having someone (or someones) who will do things with me, and take my mind off the badness, both temporarily eases the pain and allows me to return to work with a clearer mind.

In hard times, structure and relationships save my day

We’ve angered customers, lost deals, had funding fall through, made serious development errors, and messed up countless other times. So, despite all the companionship (and commiseration) I’ve found in the last year, there have been a handful of times where I’ve been close to quitting Clef, leaving Oakland, and returning home to curl up in a ball for a month.
During these times, I’ve found that two constants keep me in place until the inevitable rise out of the valley: structure and relationships.
I’ve added a second part-time job to my daily routine to keep me grounded and in place, structured my days so I’m forced out of bed every morning, added a weekly high note every Wednesday with Clef cooks (a community dinner we run in Oakland) and scheduled nightly emotional check-ins with my co-founders. These constant structures keep me going even when my world feels like it’s falling apart.
The two most important people in my life right now are Brennen and Mark, my co-founders, roommates, and best friends. In the dark times where I’ve considered giving up, my relationships with them have kept me going. The thought of harming them by backing out of the thing we’ve poured our recent lives into is too painful to consider. We support each other through our individual hard times because we each know that the other’s better day is coming soon.
Looking back on the last 5 years, one of the strongest constants has been the feeling that I am continually learning new things; that I am on an upward climb towards some sort of enlightenment. Unfortunately, while this feeling is exciting, it also guarantees that I’m inevitably wrong (or know nothing) about a slew of things at any given moment. In other words, I’m likely wrong about a thing or two in this essay. If you made it this far, you likely know a thing or two about a thing or two, so I ask that you enlighten me and help me return with a better understanding next year.
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