Time and time again, I’ve learned a really important lesson: with time, those moments that you think are your deepest scars, can turn into the most beautiful tattoos.

Put differently, I used to think that I should be thankful for good things in spite of the chaos along the way, but recently I’ve changed my mind about this. I think the trip is just as rewarding as where it is you’re trying to go.

Anybody who entered the workforce between 2008 and 2010 would agree that it was not a very steady time for the economy, financial markets, or really, anything at all. We were just coming out of one of the most severe economic recessions since 1929, and in August 2010, I was sitting in a waiting room for my exit interview for a job that I had just started seven weeks ago. As I waited, the talking head on the TV said something I still today this remember: if you’re in a job, you better keep it because it’s unclear how long before this is over.

But before I explain that part, let me try and remember how I got there.

In early 2010 during my fourth year of undergrad, I started taking some interviews with the usual companies that recruit right out of school. I got an interview with a big accounting firm, and I remember the on-campus recruiting person telling me about how this job would use cutting edge tools and I’d be tracking down sources of terrorist financing “all sorts of James Bond shit” (his words). I couldn’t figure out what to do, so I signed on the line that was dotted and took off to travel the world before starting my new job in DC.

I sort of knew this wasn’t the right choice, but I didn’t know what the right choice was so I picked the best option I had and that was working for this big accounting firm.

The first 6.5 weeks of this were on-boarding and training. As a huge multinational corporation, there was a lot of on-boarding material. We had things like a SQL boot camp (I had done a lot of SQL in past projects), anti-sexual harassment training (I knew nothing about this; up till this point I’d probably spoken with <5 females, ever), and a miscellany of other trainings.

On week 6 day 4, we were assigned our projects. I was elated and ready to track down some terrorist financing and do other cool spy work. Turns out, nobody really did cool stuff like that. Not at all. What we actually did was far less exciting:

In 2010, lots of community banks were failing left and right. And there was some issue where in order to get depository insurance, failed banks would submit hand-written loss ledgers and the government would pay for them. Imagine lists and lists and lists of shitty subprime mortgages that had defaulted all across the country. Appraised value: 2.2M. New Value: 400k. Loss: X. Again. and again. and again.

Some of them were hand-written. Our job was to take the hand-written ones, and enter them in a spreadsheet so that other teams could audit them for mortgage fraud.

This wasn’t as exciting as I had thought.

Nevertheless, the economy was tanking and I was a fearful new college grad. So I put on some music and got to work.

I did this for all of four hours until I had an idea. I knew some Python, so why not write a script to OCR these forms and automatically get them into a spreadsheet? I could save myself, my team, the company, and even the government, so much time!

I tried installing python on my work computer, but I didn’t have privileges to install the binaries. I tried a couple of other tricks, none of them worked. So that night I skipped the company booz-cruise boat tour, went straight home, and wrote a python app to do this. It was pretty easy, under 200 lines of code. I finished around 10p and went to sleep, proud of myself for having built something epic.

I brought it to work the next day and started churning through these loss ledgers. I worked through a week’s worth of loss ledgers in a few hours, and spent then spent rest of the day watching MIT OCW videos. Went home feeling like a national hero. After all, I just turned a two-month project into a two-day project, and I thought I had done great work. You’d be crazy to think otherwise, right?

Well, the next Monday morning, a calendar invite popped up in my outlook. The partner in charge of the project wanted to chat with me. I was thinking maybe he wanted to commend me for a job well done. After all, I saved the team, the company, the government, and really the taxpayer so much money. Go me!

I opened his office door, but lo and behold, he wasn’t as excited as I thought he would be. Skip past the few minutes of small-talk, and he brought up my script. I shared the details and told him about how much faster I was and how I could save everybody time and money and how I thought this would be great.

There were a few seconds of heavy silence.

Then he gave me a look of disappointment.

He then took a deep breath and said:

Omar, one day you’ll understand. At $COMPANY, we bill hourly. What you built is a nice science project, but please get back to doing your job.

I had walked in expecting a promotion or something, but instead, I was getting admonished.

That’s when I remembered a couple of things:

1. First, to always know what problem you’re solving. In this case, I thought we were solving loss ledgers, but we were actually maximizing billable hours.
2. Second, I thought this company would be long innovation, but we were actually short innovation and long bureaucracy.

This is another thought I keep coming back to. Is an organization long innovation, or long bureaucracy? Maybe it’s possible to be both, but at the time, I was convinced enough that my current employer was not long innovation.

I wasn’t completely sure how to proceed. I went back to my desk and did some loss ledgers normally for the rest of the day, but once you build something that automates yourself out of a job, it’s really hard to go back. It’s kind of like taking the red pill. And it sounds great and everybody says they want to take the red pill, but taking the red pill also means you’re momentarily unemployable because you know what is possible but don’t quite have the skills to deliver, so you’re in this middle ground where you know what things could be but you can’t actuate the change.

I probably had a whole bunch of options in front of me:

• I could keep working on this project
• I could switch to a different project on the same team.
• I could probably even switch to a different team. After all, this company had invested weeks of training on me and I’d shown some promise and ability to code.
• Or, I could even find a new job in DC.

Ultimately I ended up going for none of the above and went for the hail-mary.

ノ•ᴥ•ʔノ ︵ ┻━┻

On my way home home from work, I texted Matt Humphrey, someone I met at Startup School in 2007. Matt had recently started a company called HomeRun (sort of a GroupOn competitor), and I figured I might be able to do something to help there.

I forgot exactly what I said, but I think it was a 2 minute conversation and it ended with “sure, come on out. Maybe some time after Labor Day.”

Boom. That was all I needed. Time to bet on myself. I was going to California. I didn’t really know about the windy road ahead, but none of that mattered, I’d do anything as long as it didn’t involve compiling loss ledgers.

I got home and wrote an email to my boss, giving two-weeks notice. I wrote that I had “accepted a competing offer” but in actuality, I didn’t really know anything about my new job in California. I didn’t have an offer letter, no idea or expectations around salary or title or anything; Matt was willing to take a chance on me and I was going all in.

I sent it and went to sleep dreaming of all the things that might be.

The next morning I showed up to work, and the partner (who just yesterday told me to stop working on my science project) was a little upset. I’m guessing he got the email. But I scheduled my exit interview and that was that. And that’s how I ended up in the HR lobby, listening to the CNN newscaster reminding me: if you have a job right now, you better keep it.

I have middle eastern parents and they were also a little upset, as I think any parent should be. But that didn’t stop me. I booked my one-way ticket from DCA - SFO, threw my things in a suitcase, and counted down the days my flight.

I had all sorts of fears of going broke or making some life-altering mistake, and it took me a while to grow past those.

I leaned heavily on a couple of folks when I moved to California. I crashed at Sam’s place in Mountain View for a few nights, but decided that I wanted to find a place of my own and I’d only be able to do that if I were in SF. Another UVa friend, John, had opened up a small office in North Beach and he let me sleep on the couch there. So up to SF I moved.

It was a modest start. For starters, I was living in an office and there was no shower. So I did the logical thing and signed up for a 24-hour fitness membership and “went to the gym” every morning - aka lifted weights for 5 minutes and took a shower. I spent the weekends looking for rooms in the city.

I showed up to work at HomeRun the day after Labor Day and started an internship over there doing data analysis. I think Matt’s actual response was “woah, you actually showed up” but I don’t entirely remember. But yeah, I’d done it. I had quit my job in DC, moved to San Francisco, and was going to make something of myself. I spent the weekends looking for a place to live. Even in 2010, it was a little hard finding an apartment in the city. Ultimately, I settled on a sublet in Russian Hill. There was a man living there who did two things: ride the exercise bike in his room and day-trade technology stocks. He had diverse interests.. he’d get mail from the California Eugenics institute and he’d talk about breeding race-horses. But honestly, I didn’t care because 1) rent was $1,100/month ($1,000/mo since I paid cash), 2) I was sleeping on a bed instead of a couch, and 3) I could cancel my 24-hour fitness membership because the bathroom had a shower in it.

I bet on myself and it felt like things were starting to take shape.

I was really into data analytics and visualization at the time, and had written an open source library called django-protovis. Looking back at it now, it wasn’t a great library since it mixed all sorts of presentation concerns with backend logic, but here’s the thing I’ve realized about writing code: if you’re not embarrassed by code you wrote in the past, while you have a momentary accomplishment, it also means you’ve plateaued and haven’t gotten any better.

I gave a talk about django-protovis at a SF python meetup, and that turned into a company asking for help with data visualization. I started spinning up some consulting projects with companies in the city. One thing led to another, and I ended up signing the biggest consulting client ever. It was an oil company that needed help doing PDF data extraction. I accepted it and it was awesome.

This was a sweet role. I still remember my sweaty palms as I put in my bid. And they accepted it. Trust that I splurged and got guac in my chipotle that day. It turns out I was competing with several other consulting firms and I won because I was the lowest bid by a factor of at least 10.

Incentives rule all, and if you’re bullish on yourself, you should choose to be responsible over outputs rather than inputs.

Feeling avocado-rich and independent, it felt like things were starting to come together.

San Francisco was magic. A great way to really understand a city’s culture is to go on a lot of first dates. If I tried to explain what I was doing in DC, first dates would hear it as “unemployed and without a full time job.” But in San Francisco, I was running a consulting business.

And wait, it gets better. The python app that I wrote for this consulting project was structurally similar to the one I had written for my job back in DC. I couldn’t but help laugh at my change of fate. In DC, automating my job meant that I got in trouble for saving people time; where as in San Francisco, I owned the one-man consulting business that did it and was making three times as much money, working 2 hours a day.

Things started picking up and I got a place in the Mission. It was on Lexington Street, between Mission and Valencia off of 18th. This was way back when, when The Summit was at 780 Valencia Street. Things were looking up, but that didn’t stop me from getting two roommates.. after all, it was a 1000sqft 2BR/1BA apartment and I was afraid of losing everything. So I kept living on a shoestring and lived like that for the next 5 years.

For a few months, it felt like I had it all figured out. I bet on myself and it was working. After all, just a year before, I was in DC wondering what my future would be. Now, here I was running a great consulting project for an oil company, spending all my free time learning to code, and spent the rest of my time hanging out in various coffee shops in the mission and making new friends.

I remember going on a first date with someone I met OkCupid and it felt like things had gone full circle. We were out at some bar on Valencia St (not Delerium, not Dalva, they all sound the same) and she asked me what I did for work (as all SF dates start), I told her, and she made some comment about it sound “james bond”-like.

That took me back because the last time I’d heard that reference was back in DC during my consulting interview where I was sold the false dreams of working on something interesting, only to be duped to do glorified OCR work for the government. But times had changed, and this time around, I had control over my life and time and could do whatever I want. So I spent most of my time learning to code and building things.

I was far from home and still didn’t have all the answers. But I also had no metro commute or senior partners to placate. I went all in on myself and took a chance. And while it was uncomfortable sleeping on an office couch and embarrassing to make eye contact with the receptionist at the 24 Hour fitness every morning I went in to “work out” and shower, I wouldn’t trade those experiences in for anything since the story of how you got there is the only thing you get to keep. And it felt like things were starting to work.

I’ll add more to this series soon. But spoiler alert: there’s no part where I ever feel like I suddenly “figured it out.” I don’t know if I’ll ever be able to fully shake the impostor syndrome and the feelings of self-doubt. But another spoiler is if you can figure out how to channel them productively, maybe those are the seeds of the thing that becomes a superpower.