The Burden: On my new life as an engineer

My first 500 error page

We, like any community, are subject to the occasional cliche. In the tech world, one that's always been prevalent is that of the recluse, socially inept, programmer. The frazzled stare, the bloodshot eyes, the occasional stammer before their mind runs off into another world - a world of haunting bugs and the eternal quest for elegance and speed and the victory of achieving both.

I have to tell you, I didn't really understand where this stereotype came from until recently. Now, as a full-time engineer at Picturelife, I feel like I live it.

No two ways about it: In my transformation from "founding business and product guy" to fulltime founding engineer there are specific ways in which my life has changed and I've become a different person. I may have even become a worse friend. Here's how:

Late for everything

As a business guy, I was pretty good at being on time to meetings -- with new colleagues or long-time friends. If something was 20 minutes away, I'd stop working on whatever I was doing 25 minutes before I needed to be there knowing I could just pick up whatever I was doing when I returned.

Now, as a developer, I'm late for everything, and sometimes I bail on meetings/events altogether, with almost no warning to the other party. When this happens, it's usually because of one of these reasons:

  1. Shit's crashing/scaling/launching/slow and I need to fix/scale/tweak/deploy it. As an engineer, your finger is much more on the pulse of the NOW of your company. If something's going down, I have a bigger obligation to fix the code/server/whatever than to be at our meeting on time.
  2. I'm knee deep in a problem. Sometimes when you're working on a big problem, you can spend hours or days just loading enough relevant information into your brain so that you can actually work on the problem. It's as if your brain is a computer and in order to start processing data you load everything into RAM first. Sometimes you've worked so hard to get information into your head that you're scared to just leave it and head off to a meeting only to come back and have to spend hours or days getting back to the same place you were before. And so you bail.

Endless Priority 1 Work

As a business guy, and even at the height of my involvement in the NY Tech Meetup (i.e. running it fully) and managing a team of 12 engineers in Israel, I could regularly get to Inbox Zero.

I had more on my plate back then, but if you emailed me, you got a reply. If you were a good friend of mine, you even got a reply in minutes or hours.

Today, my inbox is a mess and I regularly permanently blow off emails from people I think of as really good friends.

What's happened?

As an founder + engineer I feel like I have endless work now, without breaks. Before, as a product guy, I could load my engineering team up with tasks and todos, but once I reached their limit for throughput (and mine for a backlog) I could back off and focus on other things. My work was cyclical. I had time to focus on things that weren't my main occupation.

Today, that dynamic is gone. If I can dream it, I can do it, and often I'm exactly the person who needs to do it. That means there is never a time when my time isn't best spend writing more code, debugging for a user, or optimizing our stack. Our dreams for Picturelife are about 15% fulfilled, and so there's always something to code or do.

Because one thing occupies highest priority and doing email is never at the top, I end up blowing people off more than I'd like. It's turned me into a worse friend, but, it's the closeness to the product you can only achieve if you actually write code and do the work. It's what I dreamt up when I decided to learn to code, and so I've accepted that this is the way it "must be" while I'm holding this position at this stage of my company's life.

Higher stakes hand-raising

I've always been one to raise my hand -- to volunteer to get something done. It's the path that led me to lead the NY Tech Meetup, and its something I've done since I was very young.

Now, I'm often the only engineer in a group (or in my family), and so when I raise my hand now it's to build out software, not just organize a BarCamp or edit a newsletter.

While I've had a transference of skills from soft to hard, my hand-raising has gotten me into higher stakes commitments. It's one thing to volunteer to organize a meeting, but a whole other thing to volunteer to build a web platform for a group.

With more powerful super powers, I have to be more careful about showing them off.

Working with Friends

Last night I tweeted, asking for ideas on what to blog about, and my friend Jonathan suggested "Working with Charles Forman."

Now, I took that as "Working with Charles Forman, the man, the myth, the legend." But there's a more important and common issue here, and so I'm taking it as "Working with Charles Forman, your friend, long before your business partner."

You see, I come across founders all the time who no longer speak to their fellow co-founders. In some ways its understandable because startups are so high stress that someone's bound to get upset at another person and have a falling out. It's also understandable because we're taught as an industry to value the success of our startup above nearly all else. So for some folks it's sad that a co-founder gets alienated, but hey, it was for the good of the startup, right? We have a fiduciary responsibility above all else, right?

Really, this stuff is just super sad, because if you've lived with eyes wide open long enough you know how few real friends you have out there, and how many companies you get to start in a lifetime. Sure, this industry is packed with nice folks you enjoy talking industry trends and drinking beers with, but how many people do you know in the industry that you'd invite to your wedding, or that you'd share real fears and anxieties with?

Real friends are few and far between. So, what happens when you start a business with one of them?

When you start and run businesses with friends, your priorities should be about preserving the friendship throughout the process. As it turns out, I think great friends make great products and built great businesses, and most especially they build really awesome company cultures together. I think because Charles and I were good friends before we started Picturelife, and especially because Charles and Jacob were such good friends long, long before we started Picturelife, we've been able to build a culture of friendship and mutual respect throughout the company -- not just among the founders.

Nowhere does this dynamic come into play more than in being separated by a timezone. Picturelife is a Chicago company, and 7 of the 9 of us, including Charles and Jacob, live and work in our (amazing) Chicago office. Meanwhile, I live in NYC and Joe, our first employee, lives in Philadelphia. We're on Google Hangout and IRC all day long, but we don't see each other much face to face.

Being far a way from one another could be a bad, bad thing. Nuances in communication is very difficult from far away. Brainstorming is difficult from far away. I'm a big believer in human-to-human interaction, but there's a reason we've worked so well together while being apart: we've relied on our friendship. When we call each other up about a new feature idea or business opportunity, we know where the other person is coming from and what they are thinking because we've taken the time to know the other person and their personality. Doing this with everyone you work with is super important, and will help you work together no matter the distance. See the other person as just a colleague, chances are you'll have issues making great stuff together.

Am I saying everything is always peachy-keen among Charles, Jacob and me? Hell no! We piss each other off all the time. But, we all care about being good to one another in the business, and knowing what's going on in each others' lives outside the business, and so when tough stuff arises we know how to deal with it and push through it in a way that doesn't negatively affect our relationships or our business.

So, that's what it's like working with Charles. It's like working with a friend, whose opinion you value and whose life you care about. It's been an amazing experience doing this with him, and Jacob, and Chris (the other fellow now on our team, who I knew from before founding the company), and I wouldn't change it for the world.

I'm Excited for You

In the past several weeks, I've met up with a number of good friends who are moving on from their current startups; moving on not because the companies were all out failures, but because sometimes you've got to cut your losses and, well, move on.

If you're facing the same thing -- maybe induced by a "Series A Crunch," founder fallout, boredom, or whatever -- you're dealing with the fact that your dream won't be what you hoped. This one was not "the one." The gig is up. They naysayers were right. It's time to take your ball and go home.

It's an experience I know all too well.

And that's why I'm excited for you.

When I look back at my times between startups or vocations, these were times of great discovery and personal development.

After my first job out of college, I started attending digital media industry mixers, getting to know the lay of the land, ultimately landing my a paid consulting gig at National Public Media, giving me a foothold in nacent NY tech scene of the mid 2000s.

After BricaBox, I got to invest all my time in the NY Tech community as an EIR for David S Rose -- and reconnect with community organizing in Barack Obama's 2008 campaign. Both these experiences led me to earn the Executive Director position at NY Tech Meetup four years ago.

After AnyClip, I got to spend quality time, pow-wowing with friends, gaining their advice; and, ultimately, that led me to the decision and process of learning to code -- forever changing my life.

Beyond the personal development, moving on means you'll find yourself doing something new soon -- no doubt something better. When I tackled AnyClip, I left behind the mistakes I made in BricaBox, and in Picturelife I'm operating with the experiences of two personal failures behind me.

So, whether it be in the context of not getting funded, or in the context of just moving on, congratulations  I'm excited for you. Whatever's coming next is going to be totally and completely rad.