Life & Career Lessons – 2012

Music: Angels and Airwaves – Diary

I’m always a little late on the 2012 lists, stick with me, this’ll be worth it.

Executive Summary of 2012:

I started 2012 by taking a bit of a risk careerwise, where before I had been the enterprise huge-company guy, I ventured into mid-sized startupish culture, pushing myself out of my personal comfort zone in terms of commute and direction. I was getting into mobile (IOS) development in my spare time, but still wanted to fill in some experience gaps I’d missed in previous opportunities. I had a good 10 month run at a great ‘startup’ in downtown Austin, was laid off, felt my world was upside down for a little while there, and came out of the tailspin – righted myself and found myself with a really great career path/opportunity for 2013.

2012 wasn’t all career & code, but it was certainly too much of it, and it shows. We’ll get to the finer points on that angle as we get through the list.

So, here’s what I learned:

I learned to take risks.

When I quit my job at PayPal a few years ago, I had interviewed around a bit, but didn’t find anything quite perfect. Meanwhile, I was steadily growing more and more disenchanted with code and slow moving big companies. At some point I decided to just quit, taking the risk to take a little time off to take a break, and fall back in love with code in the process.

The day I quit, I was scared to tell my wife what I’d done, and I was shocked when she gave me one of the best hugs of my life and simply told me “What took you so long?”. – Only days later she would not stop telling me that there was an immediate change in my mood, my sense of peace, and my happiness.

The thing that happened when I quit PayPal was, I took my destiny into my own hands. I decided firmly that PayPal wasn’t it for me, and that the next great thing was out there somewhere.

I spent that next year consulting on a cloud infrastructure product at Dell, making some really great friends in the process, and learning all about datacenter innards that I’d never had a chance to learn about back at PayPal.

When the Dell gig was up a year later, I interviewed around again, and found myself pushing my personal envelope of comfort and safety even further – trying a startup-like mid-size company with an open-atmosphere office layout and 90% all-star employees. I wasn’t a cultural fit for the new place, but I was surprised to find myself very comfortable in my own skin – despite philisophical clashes with the culture at large.

The point is, the downside to risk is the unknown, but the upside, if you can handle it, is also the unknown. Each time I switched jobs I learned a little more about what’s always the same in software, and what can be, and should be different. Each time I jumped from one ship to the next, I accepted a little bit more risk and discomfort, and learned a lot about myself, because the opportunity ahead of me always offered 1,000 new variables.

While I was at that ‘startup’ with the all-stars, I learned quite a few valuable lessons, such as:

I learned that sales guys really matter.

As a hot-shot self-involved software engineer/coder, I’ve always had trouble understanding what it is that the sales guys actually *do* at a company. It always seemed the sales guys were the guys selling more than we could deliver, and generally mucking things up – this may still be a fair assessment for a giant cant-do-wrong company such as a PayPal or Dell where the money is pouring in the doors no matter what happens. … It would not be unfair to say I had contempt and disdain for the marketing guys.

Then I worked at a startup.

When you personally meet the 3 or 4 guys who have those sales calls week to week to keep the 3 or 4 big clients sending the checks in, the contempt fades. When you hear the war stories of those 3 guys working in a shitty little closet of an office, and see a team of 20+ engineers around you in a posh downtown office making great salaries 3 years later – the disdain goes too.

Seeing and hearing those sales guys in action was, I think, *critical* to my understanding of how the world works. And let me tell you, Mr. Hotshot Engineer or Designer, the part you do, doesn’t mean shit. The world of money goes around based on relationships and a little bit of luck. The guy in your office who’s non-replacable is the guy who looks and acts like a walking parody out of a ralph lauren ad – so long as he can sell.

When you see VP so and so from client X lose their shit for some random reason and threaten your company’s bottom line on a whim, then see your sales guy have that same VP offering more money next month after a 5 minute phone conversation, that’s when the light bulb clicks on, and you realize that really, the code matters a little, but not very much.

I learned that assholes matter.

The thing about jerks is, they run their mouths. The thing about the right kind of asshole is, they’ve got charisma, and backbone. There are certainly standard run-of-the-mill wannabe jerks who don’t have the right, and I’d argue we could all stand being nicer to one another day to day in general, but man, assholes make the world actually move.

Working in the big company, you’ll see an executive here or there who wasn’t the original big idea guy or gal, and wasnt the nepotism stick-it-out-long-enough ladder climber – frankly, this odd executive is the asshole. And, like it or not, you and I need these people.

When you work in the smaller company, and see the next engineering VP hired cold off the street, along with half a dozen other hires – you’ll know which one he is. He’s going to run his mouth. He’s going to be friendly to everyone, but trash talk everyone too. He’s cunning, he’s smart as a whip, and if he’s rude, he’ll get you if you cross him. Most everyone will agree that this new guy is going to ruin the company, except.. he doesn’t, he does the exact opposite. It’s the nice polite guys who are too scared to risk their necks who ruin the company.

The thing about the asshole is, he gets shit done, he has drive. He has a fault of running his mouth, and along with that comes a life full of lessons of how to get himself out of the jams his mouth gets him in over and over – that means, this guy has a spine, this guy can make tough decisions, and this guy will deliver when it counts.

I’m not advocating ladder climbers, I’m not advocating jerks being jerks for the sake of jerktitude, I’m just saying, they have a place, and when you find the right asshole, they’re going to deliver and kick ass while doing it. The delicious irony will be, 5 years from now when your midsize is larger than midsize, the asshole who everyone hates will be the only executive of the lot who arguably deserves his merit badge title. Think on that.

I learned the value of having lunch with others.

One of the perks at my job last year was paid lunches. This is a really great thing for developers, because developers are idiots in many ways. First, they’re anti-social, and secondly, they’re cheap. So, if they can pretend to be a robot and work 8 hours straight with a hotpocket “meal” in the middle, they will, like idiots.

The downside to this is that it takes your developers a year to make the friendships your marketing team will make with each other in a week. The solution to this problem is to get your developers to go have lunch together.

After having lunch with my new peers for only a few weeks, it became immediately obvious to me how stupid I’d been in my career until that point. Previously I’d always opted for a 15 minute or 30 minute lunch, microwaving something, and getting back to it. In only a few weeks with the new group, I knew more about several of those guys than I did people I’d worked beside for 3+ years at PayPal.

Lunch matters, take it, and have lunch with friends and colleagues, often. Happy hours, too.

I learned that open environments can work for coders, within reason.

Open environment offices are an in-thing. Facebook did it, so everyone else must now do this too.

I disagree with the open environment if it’s done the wrong way. Doing it the wrong way includes: forbidding telecommuting; having more than ten people in any one open space; having sales guys in the same open office as the coders; not providing quiet spaces (couches, little closet hotel cubes) for people to go to to talk or work; and test-piloting your open-space idea on an executive sales team, then mandating it for the world (PayPal..).

Doing it the right way means doing the opposite of everything above, and providing nice noise cancelling headphones for your employees.

Coders need quiet, and time to think, and noise-cancelling headphones are not enough. The place I worked this past year had a great open-environment layout and telecommuting policy, but even still there were more than a few days where I had unending headaches caused by the choice of music or office chatter.

I learned that telecommuting is really awesome, within reason.

Let’s see, this past year I accomplished many things while telecommuting, I watched the entire 5 seasons of the wire (amazing, perception altering show, btw), many movies, did a lot of laundry, took my dog on many walks, and was more productive than I’ve ever been at any job in the meantime.

Telecommuting isn’t for everyone, you’ve got to be driven, on-task, and have a list to constantly feed on when you finish the task before. But, for coders, who need the quiet, the peace, and the space to play This Will Destroy You at deafening volumes from time to time, telecommuting is great.

The thing to remember about telecommuting is that it’s lost face time with your colleagues and boss, and you’ve got to make time while in the office to make up for that lost time.

When 2012 started, I thought telecommuting was something you do on a day without real work, in a startup-like mid-size, those days don’t exist – and that’s a good thing, because by the end of 2012 I can safely say telecommuting days are the days you take to really go heads down (even with This Will Destroy You or The Wire blaring in the background) and get shit done. Asking for a telecommuting day no longer carries a guilty connotation with me, and as a person who consistently delivers, I actually *need* the freedom to just go do the right thing from time to time.

I learned to track myself better.

I’ve always been a list maker, and from time to time I burn myself out with the lists. There’s a balance between the lists and actually letting life just happen, and I suck at that balance.

It turns out, I had a fatal flaw in the way I managed lists. That is, I deleted items after I finished them.

Don’t delete items after you finish them, grey them out, in place, and make a new list each week.

When you grey the items out, you start to get a feel for how much you actually accomplish.

Going into 2012 I was constantly feeling stressed out that I was never on top of my list, and that the list was constantly growing.

After a year of greying items out I feel worlds different, I now have great pride in how much I accomplish, and yet I also finally understand about how many items I can truly knock out per week. I also, for better or for worse, realize what a shitty friend and flake of a person I can be sometimes, because the lists show me these things where before the giant list that never ends with deleted items did not.

I learned that tracking myself does not matter.

One thing I’ve always done with my lists of tasks at work is track what I did each day, because I thought I could cover my ass with the paper trail. It turns out, that matters somewhat, but .. well, not really ..

I learned to be fired (and, when to quit).

I wasn’t fired, I was layed off, budgets got tight, last in first out, etc, but really – I was fired. I was on the top of the boss’ list to axe for a while, and I knew it. I wasn’t a great cultural fit, and had fundamental philosophical differences with prioritization and feel-good-about-ourselves-rewriting-endlessly-for-the-hell-of-it wankery.

When I started working at the place, it was an uncomfortable risk in several ways, and at first I gave myself 6 months to decide if I liked it – at some point that changed to a year mark, and a little after that it turned into a “2 or 3 years, I guess..” kind of thing from my side. I was into it, having fun, but cultural friction was perpetually upsetting. Nothing quite like being 1 of 5 “platform” engineers never invited to the endless feel-good-about-ourselves wankery standards meetings that never went anywhere, perhaps the fact that it was wankery in my mind had something to do with it 🙂

To the point about covering your ass with your paper trail, the thing there is, that doesn’t matter. If someone has a target on your back for whatever reason, the paper trail won’t help you. What will help you is spending more time getting to know people and working things out by communicating more, if anything.

Communication helps, but also, life is short, if you’re unhappy with your lot in life, even a little bit, consider changing your lot. For me, I had to be laid off to have the wakeup call that I was settling in several ways to work at the place. I had convinced myself that the settling was part of the discomfort/risk experiment, and honestly I’d probably still be working there today had I not had the not-so-gentle push out that I needed.

Saying I “Learned to be fired” sounds funny, but truly, learning to not compromise 100%, have a little backbone, and be myself mostly was worthwhile. Had I not been myself, I would have hated myself for capitulating to philosophical differences I couldn’t get behind, and I probably still would have been first on the list to go. There’s a stigma to the thought of being fired, especially if you’re someone who’s fired for really bad reasons – such as not actually doing your job. In my case, I did my job to the best of my ability, and kicked ass while doing it, all without compromising my character or beliefs in the process. Being let go for philosophical differences is a lot like being that hard-won asshole VP – being let go b/c you give a damn, and stood up for something, but fell on the wrong side of the dice. (In this case, I just gave a different Damn than the rest of the team.. :))

I’m not advocating getting fired, but truly, politely contributing to the cause without making a scene of your philosophical differences too often, is worth it, even if you’re fired over it. I suppose a secondary lesson to learning that assholes are needed is that you can’t be everyone’s friend. You win some, and you lose some. That’s really all there is to it.

No slight to the people I worked with or for, to each his own, truly – I wasn’t a cultural fit at the place, end of story, and that’s one of the beautiful things about software – there’s a dozen or more overarching cultural styles you’ll encounter depending on the shop – if you don’t fit at one place, you’ll fit at another.

I learned to communicate with my spouse, regularly.

The layoff could have been a lot worse, had I not been able to communicate openly and work through the topsy-turvy tailspin with my wife by my side.

Earlier in the year my wife and I had gone to some couples therapy together. As a non-religious person who values reason and actually doing something to change yourself for the better, I highly recommend therapy when the time is right.

We skipped marriage counseling, luckily having enough wits about ourselves to already talk about and understand each other’s thoughts on money, babies, family, etc before actually tying the knot. I’m glad we skipped marriage counseling b/c honestly we wouldn’t have enjoyed it or been ready for it – we were on a high that didnt really dip from the day we met until late 2011 – the counseling would have caused needless turmoil, or been wasted on deaf ears.

So we had communication breakdown, and went to speak with a counselor, a great one.

It’s funny how even the greatest relationships still have amazing amounts of built-in fear and reservation. There were so many downright silly and stupid things that my wife and I were so scared to talk about with each other, nitpicks on character or even habits and whatnot that didnt matter in the big scheme of things. The thing is, the nitpicks build into a mountain at somepoint and will kill you if you can’t talk about them. Having a third party intermediary person there to listen to us and encourage us to talk about the scary things really helped.

At first, there were many tears and deep breaths while we vocalized things that were bothering us, and sometimes voices were raised, but the counselor kept draining reason into our ears and showing us how to handle these communications on our own. A few weeks later, even the most intimate fears or new worries were voiced easily without any fear at all – we didn’t even need the counselor anymore. That’s how you can tell you’ve got a great counselor, when there’s an end game and you can see yourself clearly in a better place of understanding than before.

Another tidbit the counselor gave us was a really great, if corny sounding tool: relationship talks.

A relationship talk is a weekly meeting (no shit, like a business meeting) that lasts 20 minutes. Spouse A has ten minutes to talk, uninterrupted, if time is left at the end of their ten minutes, Q&A can happen. Then Spouse B takes a turn. That’s it, the end. Next week, you switch who goes first. After the meeting, you do something fun together, which in our case usually wound up being a walk around the neighborhood b/c we’d find there was so much stuff to talk about that the relationship talk would open up. You do the relationship talk *every* week, no exceptions. Sometimes the talk’s a tear jerker, most times it’s boring, but doing it every week is essential.

The relationship talk keeps the communication lines open. When they’re wide open and you’re humming along happily, the talks may be a bit bland, but even then they’ll suprise you with news you had no idea of, and when the comm lines are shut down or atrophying, the relationship talk will save you. I promise.

We also started doing ‘Wonderful Wednesdays’, which, more or less, is date night. No computers, no tv, something wholesome and fulfilling and rejuvinating, together, no exceptions. In practice, it’s sometimes a ‘Wonderful Tuesday’ because something really can’t budge, but making time in your life, together, to chill the fuck out is important.

I learned to read myself, and trust my gut.

I am what, and who I am. I’m driven, impatient at times, overly dramatic, and extremely emotional when everything’s just right.

Otherwise, like most of this last year, I’m dead inside.

Early on at the startup, my boss informed me that he didn’t like the way I communicate, I’m too wordy, imprecise, yatta yatta. – It was a fair assessment in part, but I took it all the wrong way and used it as a vice rather than a tool to grow with. Long story short, it fucked me up.

My natural style is to be transparent, open, and accomodating, so hearing that I was expected to be more precise and careful with my words sounded a lot like I’d have to be someone different while I worked at the place if I was going to cut it. In the end, I probably WOULD have had to be a different person to jive well there longterm, but the point my boss was making wasnt that I should shut down and be a different person, he was saying I should strive to be slightly less sloppy.

I told myself I was becoming a respectable little adult by shutting down and towing the line, and when I was finally laid off a good while later – it all came pouring out. My writing became prolific again, as did my creative whims. I was staying up through the night one or two nights per month, I was even honest-to-god crying fairly often at even the littlest beautiful or horrible things – I was me, again.

Perhaps I’m both of these people, the emotional creative dreamer, and the tight-ass conservative who’s dead inside, but I prefer the dreamer.

Time and time again I’ve noticed these moments where everything synchronizes into this chaotic yet perfectly ordered moment where some huge chapter in life immediately makes sense – as if my subconscious has been working on it all the while, for months. The backside of those events is always the same – I’m writing, I’m loving my life, I’m creating all sorts of crazy little mementos, I’m taking it easy more often, and I’m, yes, occasionally crying at the immense overcoming beauty and tragedy of it all.

2012 gave me metrics, if I’m not blogging for the fuck of it at 5am on a work night once or twice a month, something’s off. If I’m not occasionally trading sleep for another one-night shot at something great, something’s wrong – and it’s time to really assess what my gut is telling me.

I learned to be brave, and patient.

Life is funny. Often the most important stories and lessons of your life are ticking right along, slowly, very slowly, in the background – completely hidden by silly shit you tell yourself matters more. Here’s what I mean, when I was pulling photos from the past 3 years out of my archives for the Freddie Book, I had to scroll past thousands, literally thousands of photos of my dog. I’m a dog guy, not a cat guy, and though I think my dog’s pretty fucking amazing, the story to tell for recent years is not hers, it’s the cat’s.

Here’s a picture of the awesome dog anyway:

Anyway, after being laid off, I took time off, again like after PayPal, because I could, and because I knew I needed to. TumbleOn seemed to be taking off, so I distracted myself with dreams about that for a while, and I visited my good friend in Seattle for a bit, and so on. After the predictable this-is-going-nowhere burnout phase that followed shortly, I was finally at ease for a moment or two. This was one of those moments where the chaos distilled into clarity.

One morning I woke up, and decided to write the story of Freddie. There are perhaps 3 days in the past year like the day I wrote that story, but Freddie’s story was the best of the three, easily.

Freddie came through me like they say the Bible did the prophets, it just flowed, as if from somewhere else. I didnt plan it 3 days previous, I didnt even know what the damn point of the thing was as I was writing it, and yet, as the story flowed out it turned into this really incredible, amazing thing – an allegory for my own personal story of 2012 – of learning to take larger and larger risks, be brave, and welcome change – all while giving credit to the one person who deserves all the credit for any betterment in my life ever, my wife.

I won’t bother you with the details of Freddie’s story here, you can go read the book yourself (online, for free).

I learned that success is not what capitalism says it is.

Working at the ‘startup’ this past year was really a great experience to be walking through while simultaneously seeing our personal side project, TumbleOn, grow.

Until you’ve worked at a startup, or a ‘startup’ that’s really a decently-funded mid-size pretending to be a ‘startup’, you don’t really ‘get’ what success is. Success, arguably, in American or capitalistic terms, is striking it rich. But, frankly, striking it rich is a stroke of luck, whether you win the lottery or win the right-time-right-place lottery like Bill gates.

This past year redefined my personal measure of success. Success is not a certain amount of money, or a title, success is being one of those initial three guys in a closet-sized office, seeing 20 well-salaried employees loving life 3 years later. Success is making something great that brings joy to other people’s lives.

Would I like TumbleOn to make me and my friends independently wealthy? Sure, but to me, TumbleOn is already the largest personal success of my short little career, and the sweet and sad fact is, it may be the largest success of my long term career as well. In my own little corner of the world, I’ve been a part of a small team who made something really amazing that thousands of people use regularly, viewing more than 300 million photos in 2012, and more than a billion in 2013.. laughing, gasping, giggling, and being inspired along the way.

To me, as I said earlier this year, success is not the money, success is making something bigger than myself, that makes the world just a little bit better than it would be without me.

I learned to take detours.

A stronger relationship between my wife and I resulted in a bolder wife, who’s more uppity lately, in all the right ways. This year she really put the time in to repeat the message to me that I should live life a bit more rather than plan so much.

For example, I immediately thought to take a long-planned-anyway trip to Seattle after being laid off, but kept the thought secret and was ashamed – it seemed extravagant given the circumstances. A few days after the layoff, my wife independently suggested and insisted that I go to Seattle. I hemmed and hawwed about it, listing the cons of the idea (money), and she wouldn’t have it. She knew what was good for me, and sitting at home in the familiar, moping, driving myself crazy wasn’t it.

Months later, I was visiting some friends, absent mindedly returning from lunch with a good buddy, when I got lost.

I wasn’t lost lost, but I was way off the beaten path. My coder brain immediately detoured me to the most efficient route home – still a different route than that intended, but efficient – when all of the sudden half way home I slammed on my brakes and nearly caused a wreck – swerving into the drive way of this great botanical gardens in Fort Worth. I’d completely forgotten the place was there, and decided that for once I would take my wife’s advice, and take the detour, throwing efficiency out the window.

On my way into the Japanese Gardens, the ticket clerk asked how my day was going, I told him “it was going alright, but it’s about to get a whole lot better”. The clerk laughed. I took a few steps inside and something primal overtook me. I felt as if I were outside myself, floating through this long-familiar place, truly soaking in the beauty and moment at hand – it was a feeling I really don’t have often.

As I walked past the zen garden I was congratulating myself on taking a detour, excited to tell my wife, sure that she’d be so proud of me for actually experiencing something rather than running the numbers beforehand.

I walked and savored the moment, being outside myself as in a dream, and conscious of it all the while. As I continued on, I saw something amazing, or I thought it was.

There was this crane, sunning himself, wings spread wide to wholly accept the sun. He too, was savoring the moment, and he just stood there, zen-like in this serene scene for a full 10 minutes, motionless. For a while I was convinced he was some poetic statue painted convincingly real, and then he blinked.

Seeing that crane, on my floating detour, was one of those weird things I don’t think I’ll ever forget for the rest of my life. Now, two months later, I can barely recall many of the particulars of that visit to Fort Worth at all, but that moment in the sun, watching that crane fully accepting the simultaneous chaos, beauty, and fragility of life – that scene and moment will stick with me for life.

Thank you, wife, for telling me to take detours.

I learned that time is precious.

The flipside to living a happy and full life is that there isn’t enough time in life.

There’s something they call “FU Money”, or, “Fuck You Money”. Loosely, this is the amount of money it would take for you to quit working and start living your life the way you want, and deserve, to live it.

Something flipped in Steve Jobs’ brain one day, and he realized the best way he could live his life was to live every day as if it were his last.

This year, I learned to set my “Fuck You Money” value to $0. I’m no zen master like Jobs, but for the first time since college I can honestly say that I’m working at a place where even if I were independently wealthy, I’d still be showing up for work the very next day.

That is what I, and you, and everyone, deserves.

You deserve to work with kick ass people who both inspire you and celebrate with you. You deserve to take time on wednesdays to be with your family and turn the computers and calendars off. You deserve to take time in the middle of the night to forego sleep in favor of some crazy undending blog rant (like this) or new project idea. You deserve to take vacation, and you deserve a wake-up call from time to time.

There’s this great White Stripes documentary of their last tour. There’s a segment in there where Jack White is talking about living on the edge, manufacturing wake-up calls. He says that when he goes on stage, he measures the comfortable distance to set the mic stand so he can easily grab his next guitar pick. Then, he moves the mic stand a few feet further, so he has to really jump and make himself get that pick in time. Sometimes he misses, sometimes he knocks the damn stand over, but every time he gaurantees he’s living – because he’s pushing his own personal envelope of comfort in even the silliest esoteric ways – and, he says, it works.