My burnout and me

I’ve been waiting for weeks to write about this.

I want to talk about my burnout.

I’ve been waiting because this absence of motivation is a weird, gauzy thing that defies packaging. I’ve been waiting because on some level, this felt like weakness. A thing not to be shared. A source of shame.

But we need some sharing because this happens to people.

You have to understand, I love creation. I was blessed to grow up in an environment where my imagination was celebrated and cultivated.

After we moved to Albuquerque, when I turned five, I got my hands on a great big wardrobe box. I started drawing the buttons and dials for a spaceship. That was what I wanted to exist.

By age eight, I discovered an entire genre of fiction that concerned itself largely with spaceships but also, to a surprising extent, their buttons and dials.


Star Trek: The Next Generation. Holy cats did I love that universe. You’re on a spaceship. In space. The blind see. Humanoid robots are substantive members of the community. And computers.

Computers are everywhere.

Everybody had a computer. They walked around with them in their pockets. Worked behind them, slept beside them.

They talked to their computers.

And the computers were these beautiful things of bright colors and black glass. You touched them and their software would reconfigure whatever controls you needed for the task at hand.

It was the future.

Every time you sat me down in front of a computer, my mind would inevitably wander to the unmistakable LCARS computer interfaces I saw on TV. I’d use my computer time to draw crude approximations of a world that would otherwise be so out of reach.

Burned into my memory is first contact with a Newton Message pad. This was alien technology – beyond anything I’d ever imagined. It was a real computer yet it it was self-contained. It fit in your hand.


I’d go and visit a Newton every chance I could. Any time my family ended up at the electronics store, I would go in search of this artifact and try to work out all you could do with it.

It took years of sustained lobbying, but by the time I was 10, we had a computer in the home. I’d spend hours downloading software just to see how it worked. I couldn’t believe how deep my computer went.

My portable computer fantasies were realized on my 16th birthday in the form of a Handspring Visor.



It was my constant companion. Loaded with eBooks and apps, lovingly synced each morning with the latest from the web via AvantGo, I looked after that device like a cherished pet. In time I added a fold-up keyboard. My english teacher at the time, Mr. Romero, indulged me by allowing these devices in place of the traditional pencil and paper.

I had, at last, a slice of the future.

I’d nurture a succession of Visor models and add-ons through the end of high school, sinking over a hundred hours of my Best Buy toils covering the cost.

I had no idea that any of this could be useful, one day, for a career.

When Apple opened the iPhone to third party developers, it woke up decades of dreams inside me. I risked everything I had to seize my chance for part of the wild, crazy boom of creativity and commerce that followed.

Since then I’ve gotten to work with incredibly talented people to build stuff I’m really proud of. Somehow, incredibly, it seems I have the career that that I spent my all my formative years preparing for.

But when I turn the key in my mind these days, the engine doesn’t always fire up the way it used to.  I can’t string together interdependent systems as easily or readily. I can’t find the motivation to build the models in my mind.

So much of what I dreamed of as a kid is right within my grasp but it’s like my brain is out of gas. When I think of the people who helped make this possible for me, it’s even more frustrating.

I know how I got here. I didn’t take great care of myself. Shipping a big project a few years ago, against a tight deadline, 10+ hours a day, six or seven days a week, for a couple months, during the loneliest period of my adult life, left me pretty fried.

I didn’t take the sustained break I needed to get my mojo back. I limped along, never quite back at full strength. Somehow I shipped a whole new project in that state, but afterwards I was cooked.

I couldn’t make code come out anymore.

It felt like a failing of discipline. I castigated myself. After much searching, though, I remembered that the only reason I had my career was a self-imposed program of nightly study and work. What I needed was a break.

So I decided it was time to make a change.

I make money by freelancing now. The variety of faces and places keeps things fresh. I can specialize in the parts of my brain that are still in working order. I can give the tired parts a rest until they’re ready to get back in the game.

I can take breaks when I need to.

The part of me that wants to make buttons and dials, it seems, just cannot be killed. I still love dreaming up new  interfaces. I love seeing my screen of black glass fill up with the colorful, moving shapes of my childhood dreams. It’s a good thing people find that useful.

I love the energy I get from teaching – and I’m fortunate to know a subject that a lot of people want to learn about.

But I do miss that incredible feeling of flow I only find while writing code. I miss feeling it pour out of me, working two or three hours at a stretch. The extra jolt of satisfaction when it all works on the first compile. The feeling of something being born before my eyes.

Take care of the people around you. Make sure they get the support and time they need to be their best. Do the same for yourself.

The mind is not an inexhaustible resource. It needs rest, play and new situations to be at its best. It’s not wrong to relax sometimes.

Let’s talk about the fact that in this crazy world of deadlines and competition, sometimes we get tired inside. Let’s be real that we’re not computing machines.

We’re fallible, squishy meat, just trying to make it.

Sneak into tech through the back door: a hopelessly limited how-to

In 2008, while drowning in debt and yet another sticky Orlando summer, I decided I would change my career.

I would get a job making software for my iPhone.

The path forward wasn’t especially clear. My route was imperfect and entirely improvisational. I didn’t even realize I’d end up in San Francisco. Within five years, though, I would build and launch eight separate apps. The last three were under the aegis of venture-funded startups.

If you told me back then how many people would download and use my work, I’d have shit myself.

Sometimes people ask me how I managed to make this happen. Shared below is what worked for me. This is not comprehensive or universal advice. Nor is it the only way to get a job in this industry. It may not even be relevant any longer, given how much time has passed since I began. Timing may have been critical to some of what I tried. Standard warnings of survivorship bias apply.

Still, there’s a lot of possibility in careers like these. If there’s any part of my adventure that might help light your way, I’m happy to share.

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The first time I spoke at a conference

Once upon a time, I got my first full-time job building an iOS app.

I was excited, but mostly terrified. Impostor syndrome lurked all about. I’d been designing, writing and shipping apps for a couple years, but doing it for a paycheck imposed all new pressures.

Still, I brought the beast into the homestretch in about three months. It worked. It was pretty stable. And it was mine. In addition to writing the code, it had been my job to adapt the web version of the interface to work within mobile constraints. I was proud.

And relieved.

As this crystalized, the company realized that we were booked for a conference to present a new product that just wasn’t ready. I was asked if I was comfortable promoting the new app so the slot didn’t go to waste.

Oh, hell yeah.

We only want to talk to founders

I prepared for about a week. With the help of our CEO, I polished my pitch. Pacing, timing of the on-screen demo, word choice, overall structure, nothing was left to chance. I wanted to knock this out of the park.

A day before the event, I was to appear before the conference organizers to give them a preview.

I got there and watched a few other presenters walk through their talks. The organizers had lots of feedback – focus less on this, talk more about that, speed up this other thing.

Then it was my turn. As I began to introduce myself, I was interrupted by the Head Honcho.

Wait a minute. We only want to talk to founders. We don’t want just some engineer up there.

I frowned. This was not what I expected at all. I’d been told to show up and give the pitch.

So I mumbled something, then walked toward the exit so I could make a phone call to the person who’d set everything up.

Which, to the organizers, seemed to look like a company dumping their conference. Honcho cried after me, using my employer’s name rather than mine:

Wait, wait! We want to talk to you.

Giving the pitch

This was weird, but I wasn’t about to waste all the prep time.

I got up and gave the pitch. I introduced myself as the “founder of mobile” at my organization. Honcho grinned at this – I’d won him over.

I got to the end of the talk. There wasn’t much feedback. Did I want to take a jab at one of our competitors?

I didn’t want to, but I said I’d think it over. And that was that.

On the day of the conference, I sat backstage before my slot and listened. Each pitch had some judging at the end of it. The judges were pretty candid and I started to get nervous. Now, I’d had an incredible high school english teacher who knocked any fear of public speaking right out of me. Still, it’s one thing to speak in front of an audience. It’s another to be vivisected.

My time came and I walked onto the stage.

I’d never been in front of this many people. I’d never had to speak with this many intense, dazzling lights blasting in my face.

But dozens of practice runs let me take a deep breath and plow into the pitch. The demo proceeded flawlessly. Timing was right, every cue was hit. The practice had paid off. I tried not to speak too quickly. Tried not to let my pulse get the better of me.

Somehow, I got to the end. The audience applauded.

But, oh, god. What were the judges going to say? They’d been merciless previously.

That was fuckin’ awesome.

At the end, I took home an award for the product I pitched.

Conference diversity is hard

I get that.

But it becomes easier when you look at diversity as more than “people just like the regular people, but female/brown/black.” This conference only wanted to talk to “founders.” As a result, it almost excluded someone with a great pitch.

That’s nuts – there are lots of ways to meaningfully contribute to startup land that don’t involve starting the company. If all you needed were founders, no one would gripe about how hard recruiting is.

Diversity isn’t about meeting some proportion of brown folks or women. It’s about recognizing and celebrating that lots of different sorts of people, skills, levels of accomplishment and roles have something interesting to offer.

I went back to work a hero – and it felt amazing. What a waste it would have been, for everyone involved, if I hadn’t had that opportunity. Now think of how many wasted heroes are just sitting around here, out of view of unimaginative organizers.


How I apologize: a quick guide

So ya done fucked up.

That’s okay. Everyone does it from time to time.

What’s far less common, though, is a solid apology.

What apologies do

An apology has two core missions:

  1. You need to demonstrate that you understand the problem you caused
  2. You need to assure the people who matter to you that this understanding will help you prevent future missteps.

Apologies aren’t for making things all better right now. The timeline on that is up to the people who have been affected by your mistake.

Apologies demonstrate accountability

Rather than perfectly smoothing over your conflict, what you want from an apology is a clear understanding in your audience that you have held yourself accountable for what you’ve done wrong.

Apologies that move me take this basic form, so it’s what I try to stick to when I fuck up:

I did something wrong. This is what it was.
The impact of my mistake, as I understand it, is this.
I am uncomfortable with that outcome.

Optionally, depending on audience and context: this is why I’m uncomfortable.

Going forward, I want to do everything I can to prevent this kind of problem from happening again.

If the path forward is clear: These are the steps I’ll take.

If it isn’t: I don’t know exactly how to fix this but I hope you’ll work with me to figure it out.

Great apologies do not include:

  • Equivocation: “I’m sorry you may have felt…”
  • Deflection: “I’m sorry this happened, but there were all these other people who…”
  • Vagueness: “If I did anything wrong, I’m sorry about that…”

Why apologize?

Because you aren’t an island. The rest of humanity is filled with ideas, opportunities and bonds that you will find valuable. Taking the opportunity to own your mistakes ensures that the people around you understand you’re worth trusting.

Everyone screws up. Not everyone makes it right. Seize on the opportunity to differentiate.

Why it’s hard to be a nerd who’s wrong

Mike Krahulik, co-creator of Penny Arcade, is an incredibly successful web comic artist.

He’s also kind of a dick. In a recent letter to the comic’s fans, he owned this:

I’m 36 years old now though and I realize what I am is a bully. I may have been the one who got beat up but I sent plenty of kids home in tears. I also realize that I carried those ridiculous insecurities into adulthood. I still see people who attack me as the enemy and I strike back with the same ferocity as that seventh grader I used to be. I’m ashamed of that and embarrassed.

After a career of public defensiveness, Mike disembowels himself while the internet looks on. It’s an act of courage.

It stirred in me an uncomfortable period of self-reflection. I was running code that, while not as beefy as Mike’s, certainly had features in common. I’ve wrestled these demons to varying degrees, but I’d always suffered quietly in their company.

It was a shock to realize they’re lurking all over the place.

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Explained: why people are angry at Paul Graham

So Paul Graham said some stuff and Valleywag covered it second-hand. Some people are pissed, some people are pissed that other people are pissed.

Was Graham misquoted? Is he a cartoon villain, twirling his mustache as he gleefully sends a train filled with female founders into a ravine?

He doesn’t seem to have been misquoted too dramatically, but he’s tied no one to railroad tracks either. His perceptions, made public, do explain a lot about why it’s such a challenge for certain folks to get funding for their technology venture.

Now we have full text thanks to Jessica Lessin, editor at The Information, where Graham’s words originally appeared. You can read the whole thing, but I’m going to point to parts that are most vexing.

The Pipeline

If someone was going to be really good at programming they would have found it own their own. Then if you go look at the bios of successful founders this is invariably the case, they were all hacking on computers at age 13. What that means is the problem is 10 years upstream of us. If we really wanted to fix this problem, what we would have to do is not encourage women to start startups now.

It’s already too late. What we should be doing is somehow changing the middle school computer science curriculum or something like that. God knows what you would do to get 13 year old girls interested in computers.

The argument here is that investors are powerless to change the status quo. The number of people who are interested in computers and the internet, and who happen to be women, is so small of course you won’t see many female founders.

There’s a few problems with this. Y Combinator launched in 2005 with the batch that brought us Reddit. In 2005, 20% of CS Bachelor’s degrees were awarded to women, along with 28% of CS Master’s degrees.

What was the percentage of women who co-founded a YC company in 2005?

0%. Paul Graham emailed to correct:

There was actually a female founder in the summer 2005 batch.  (That picture you found isn’t a complete one.)

Moreover, the notion that you have to have been programming since age 13 is also problematic. It excludes all but the most fortunate of people, leaving only those who:

  • Had long-term access to a computer growing up
  • Had access to a person who could, even if indirectly, mentor them on its use

Me, I only started programming at 19. By 20, I was selling enough software on the internet to pay rent on my apartment. What makes 19 less valid than 13? Or 29 for that matter? Finding it on your own is great, I very much agree. Why the age obsession?

You can look at this two ways: Graham is over-stating the powerlessness due to the pipeline problem, or Graham is exaggerating the pipeline problem by making it so long that you have to have Tiger Woods-level childhood obsession to be a valid contributor to technology.

There’s legitimate beef to be had with either interpretation.


You can tell what the pool of potential startup founders looks like. There’s a bunch of ways you can do it. You can go on Google and search for audience photos of PyCon, for example, which is this big Python conference.

That’s a self selected group of people. Anybody who wants to apply can go to that thing. They’re not discriminating for or against anyone. If you want to see what a cross section of programmers looks like, just go look at that or any other conference, doesn’t have to be PyCon specifically.

PyCon has worked very hard to create an inclusive environment. It sponsored attendance for those economically disadvantaged. It created and enforced a code of conduct for all attendees. It gave space to Ada Initiative, which provided a feminist hacker lounge in cooperation with PyLadies. PyCon went out of its way to ensure that women who wanted to participate would feel welcome.

In exchange, it saw a record number of female speakers and attendees in 2013.

Far from exonerating inaction, PyCon stands as an example of how and why to do it better.

Y Combinator is the premiere startup accelerator. With its pedigree, you’re telling me a bit of outreach wouldn’t turn up a few extra female founders?

Open Source

Or you could look at commits in open source projects. Once again self selected, these people don’t even meet in person. It’s all by email, no one can be intimidated by or feel like an outcast for something like that.

It turns out you can: earlier this month a project by the “Feminist Software Foundation,” spearheaded by 4chan enthusiasts, emerged on GitHub. It mocked the cause of feminism at large, along with its interest in technology. The project spoofed commits by other GitHub contributors who have been outspoken on issues around social justice. These folks also got some fun Twitter interactions.

You don’t have to take my word for it. Ashe Dryden covers this well:

I know many women that either don’t contribute to OSS because they’ve been dismissed for being women – being too pretty, not pretty enough, being forced to prove their competence more than their male counterparts because they’re women. I’ve talked to women who use gender-ambiguous GitHub names and don’t post a picture of themselves as their avatar because of how quickly this happens. In addition, the sexual harassment, slurs, and other derogatory language that are used directly or indirectly at these groups of people causes many to not want to participate at all.

Additionally, there are very public instances of assuming someone is male.

Most damning: “approximately 1.5% of F/LOSS contributors are female as compared to 28% in proprietary software.” So OSS is definitely not where you want to look for female startup founders.


No, the problem is these women are not by the time get to 23…Like Mark Zuckerberg starts programming, starts messing about with computers when he’s like 10 or whatever. By the time he’s starting Facebook he’s a hacker, and so he looks at the world through hacker eyes. That’s what causes him to start Facebook.

We can’t make these women look at the world through hacker eyes and start Facebook because they haven’t been hacking for the past 10 years.

Paul: Enough about Zuckerberg. You always seem to get yourself in trouble when you speak of your obsession with this young man.

YC has been around for nearly as long as Facebook has. If they were onto something on the scale of Facebook, we’d probably smell it by now. YC has certainly had some successes, but its top stuff is funded or acquired at levels, so far, easily matched by the budget of a big summer movie.

So maybe YC doesn’t yet know what it takes to make a Facebook-level product. That’s okay! I think it’s a perfectly reasonable idea to try and figure that out.

But Zuckerberg is already Zuckerberg. There’s no one else who can take his place. Cloning him is really going to limit the scope of problems you’re able to tackle. He’s a brilliant technologist and a tenacious leader, but Zuckerberg is a billionaire because once upon a time he wanted a great way to check out chicks at his Ivy League university.

The world’s problems – not to mention the pots of lucre waiting to be liberated for solving them – are far more complex and varied. What if there was more than one way to arrive at the “hacker eyes” perspective Graham is looking for?

What if “hacker eyes” aren’t the only perspective that can propel a startup to success?

Leave Paul alone?

Nah. He’s in the business of making money.

I betcha anything he makes a lot more money when he broadens the scope of his ideal founder recruitment beyond horny, privileged Harvard boys. Then we all win. Be civil, but keep on him and his investor colleagues.

But why the anger?

I’ve pointed out why someone might disagree, but not why they’d be angry.

Here’s the issue: it’s not Graham’s responsibility to fix the inequities in tech. If he has no new ideas about how to fix the problem, though, the most productive action he can take as a prominent person is to pass the mic to someone who does. It’s easy to say “It’s a problem. I don’t know how to solve it. But I respect these folks who are trying and you should talk to them.”

Instead, his overall tone is one of resignation. The position seems expert and defeatist.

Not everyone is willing to give up the fight.

While Graham shoves his hands in his pockets, real people are trying to make their mark on the world. They’re finding their progress in technology undermined by the frustrating fact that their paths look very different from Zuckerberg’s. Graham’s success has elevated him to a position of influence. In this case that influence is, even if inadvertently, impeding progress.

These public remarks justify a reality that feels pretty unfair to a lot people. Worse yet, they confirm fears that investors are pretty out of touch with the challenges faced by technologists who aren’t young men.

That’ll piss you off.

Hey Bro – you’re being insensitive

Hey Bro. We gotta talk.

You were being kinda insensitive just there. But it’s all good – we can totally get through this. It’s gonna be fine.

Before we get to the part where it’s fine, though, I want to address the objections I see queuing behind your eyes. Let’s roll.

But I didn’t mean it like that!

That’s cool. I understand that. I believe you because I don’t think you would intentionally make someone that uncomfortable.

The point is, though, you did make someone uncomfortable. Without knowing why. Nothing more is meant by “insensitivity.” You are simply absent the configuration of social senses that would have otherwise averted this confrontation.

This is not a value judgment. This is just the human condition. Everyone’s set up just a little differently.

But I’m not a *BLANK*-ist!

I should hope not! That’s not a very nice thing to be.

It could very well be, though, that a position you espouse or a remark you’ve made has some implications that feel quite *BLANK*-ist to someone around you.

If this is surprising, good! You’ve discovered a whole new slice of the human condition you know absolutely nothing about.

Maybe it would be useful to learn more about what motivates this surprising perspective.

But what about my feelings?

Bro – feel what you feel. It’s pretty upsetting to find yourself in a position where your actions have consequences that you had not considered.

You should be okay with that. Shit’s complicated.

But part of taking action is taking responsibility for consequences. Your speech has, upon exiting your mouth, interacted with other human systems and generated output uniquely meaningful to those systems. If these humans are part of your community, you will be affected by the results of your words.

Your counterparts are equally responsible for their words, but you were talking, and we’re going to focus on that first.

But they’re just being too sensitive!

Bro. You know what?

That’s the truest thing you’ll say all year.

I bet if we asked them, there’d be days where they would pay any amount of money for this shit just not to hurt anymore.

But a lot of the time, the reason it hurts?

It’s not fucking fair. And it’s not fucking stopping.

Now, I know you’ve been there. Everyone has been pinned against the wall by something that feels completely unjust. That’s a special kind of rage. It burns pure and white, then leaves you cold and emptied out.

What if that kept happening?

Acknowledging pain in a public way is no fun for anyone. It’s not done lightly and it takes some courage. These feelings aren’t there to inconvenience you.

But it was just a joke!

Bad news on that front… That might make it worse.

See, again, you’ve bumped up against something that hurts. And you didn’t even know it was there.

Now, there’s humor to be found in pain, I would be the first to agree. But if you don’t even have that pain on your map, you’re much likelier to further it than find the laugh.

But I don’t care if what I said was hurtful to someone!

Wow. Really? I don’t think you really mean that.

I have a hunch that even if you did, you’d hardly want to be quoted on it during an interview or on a date.

If it’s true that you’re comfortable dismissing the consequences of your words, I suppose that’s your right. But it will be the right of others to dismiss you from conversations or spaces built to respect the sensitivities at play.

But I’m… ashamed that I hurt someone.

That’s a hard feeling, Bro. I know.

You know why it’s so hard? I bet someone hurt you once, too. I mean that one time. Remember? The really bad one.

Remember how deep it stung? Remember how lonely you felt? Remember the ache as you escaped somewhere quiet and did everything you could not to cry?

You don’t want to be on the hook for that kind of hurt. You don’t want other people to think you’d ever cause that.

But you don’t have to feel shame because it doesn’t have to end like this. You have the chance to be very brave and very impressive before your community. But there’s one thing you have to understand.

This doesn’t end by persuading a jury.

This isn’t a thing where you cite evidence, call character witnesses or give testimony. You cannot persuade someone out of their hurt.

There’s a way out of this. A vigorous retconning of your conversation isn’t it.

So what do?

Bro, this part is really straightforward.

I don’t understand the full story of what made this hurtful to you. Either way, it was and I’m sorry.

Say it your way, but say no more than this for the moment. Bam. Done. Mouth zipped until your companion responds. You may be shocked by the gratitude expressed at your acknowledgement. You may be shocked instead by additional frustration.

Either way, you have stopped boring a hole in the soft tissue of someone else’s pain.

If your counterpart responds with civility, you may find a great opportunity to learn about their story. Explore that dialogue to your mutual comfort. That said, your graceful apology doesn’t entitle you to a full deposition on the factors that triggered this confrontation. Enjoy a moment of perspective if it’s offered. If not, you’re done.

You have a new data point – or several – about how your world differs from others’. You have clarified your good intent without negating the very real pain at the center of the problem.

That’s it?

Harder than it looks, Bro.

Worth it.

Bernie Sanders publishes some sanity porn

Holy fuck. Highlights:

I realize that our $17-trillion national debt and $700-billion deficit are serious problems that must be addressed. But I also realize that real unemployment remains close to 14%, that tens of millions of Americans with jobs are paid horrendously low wages, that more Americans are now living in poverty than ever before, that wealth and income inequality in the U.S. is greater than in any other major country and that the gap between the very rich and everyone else is growing wider.


…under President George W. Bush, wars were launched in Afghanistan and Iraq without paying for them. The cost of those wars, estimated at up to $6 trillion, was tacked onto our national credit card. Then Congress passed and Bush signed an expensive prescription drug program. It also was not paid for. Then Bush and Congress handed out big tax breaks to the wealthy and large corporations.

That’s fucked up.

Interestingly, today’s “deficit hawks” in Congress — Rep.Paul D. Ryan (R-Wis.), Sen. Jeff Sessions (R-Ala.) and other conservative Republicans — voted for those measures that drove up deficits. Now that they’re worried about deficits again, they want to dismantle virtually every social program designed to protect working families, the elderly, children, the sick and the poor.

Imagine that!

In other words, it’s OK to spend trillions on a war we should never have waged in Iraq and to provide huge tax breaks for billionaires and multinational corporations. But in the midst of very difficult economic times, we just can’t afford to protect the most vulnerable people in our country. That’s their view. I disagree.

The fresh blast of sanity is like a back rub for my brain.

For a start, we cannot impose more austerity on people who are already suffering. When 95% of all new income between 2009 and 2012 went to the top 1%, and while tens of millions of working Americans saw a decline in their income, we cannot cut programs that working families depend on.

The whole thing is worth reading.

Mobile interaction designer + developer. Unreasonable person. San Francisco is my religion.