Live / Work

How to Start a Blog: A Guide for Procrastinators

January 23, 2015

I’ve always liked words. When I was twelve, I used them to pen ten-pagers about angsty vampires (clearly before my time). At fifteen, I used them to build an escape hatch to New York City, where I got into a pre-college writing seminar for the summer. It beat my sleepy suburban town. Words could, apparently, get me places.

Fast forward almost two decades; words have come and gone. In that time I sunsetted two “blogs” (they had fewer links than a brochure site). One about coding; and one about my “first thought of the day,” which held on briefly by downsizing into my “first song of the day.”

If I liked words so much, why couldn’t I keep writing them?

Pleasure Association

If I like words, I love food. Particularly: perfectly cooked, molten-center, hard-boiled eggs. This is one of the few foods that I can happily eat every single day. Three other things I love: earl grey tea with bergamot in my favorite Kahlua mug. Watching the sun rise over my beautiful city of San Francisco. Salami.

It wasn’t until I cobbled these all together that the writing habit stuck. I started to wake fifteen minutes earlier, then twenty, then thirty-five, so that I could squeeze in this new morning ritual before my workday. I rolled out of bed, flipped on the tea kettle, set a 12-minute timer for the eggs, and sat down at my desk facing the sun.


I wish I could say I was so inspired to write that I jumped out of bed every morning. But I’d be lying. What did pull me out? Those fresh eggs, barely cool enough to peel. Along with the purely visceral pleasure of eating and sunrises, I started getting hits of pleasure when I wrote something I liked. After 1.5 months, I became addicted to all of it — the feeling of getting good at a craft, a healthy breakfast, the calm quiet of early mornings, and my sacred cup of earl grey.

Writing for Myself

I didn’t share my writing with anyone. The whole point was to start a blog, so admittedly I used a different voice than, say, a diary entry. But still, it was a lot easier to get going in “no edit” mode, knowing I didn’t have a deadline or existing audience. I wrote whatever I felt like, what was on my mind at that moment or the last few days.

I made a promise to myself that I wouldn’t publish any of these posts until I was sure I could keep the habit up: either a continuous streak of four months, or a series of eight polished posts that I was excited to publish.

Finish what you start

I gave myself one constraint: finish what you start. A good blog post – one that I felt was “finished” would take several days. Usually about two sessions to get the idea out in its raw form, then 1-3 more sessions to edit, and often, rewrite. I would literally tap a couple Enter-bars before the paragraph in question and begin writing it anew, with the original just barely in view beneath my cursor. Sometimes I would be surprised that I rather enjoyed the phrasing in my first draft, and only have to tweak a tense here or word there.

“Done” is a relative term, and I became okay with that. If I wasn’t feeling a particular blog post after four days of writing and editing, I would allow myself to relax my standards for “done” and move on. Unfortunately this has the side effect of posts being completed but not posted. Oh well!

Fail: What derailed (almost) four months of writing

I was feeling quite chuffed, having had a solid morning writing streak of over three months. My four-month goal was so close I even let myself ogle a few WordPress themes. I had emptied enough egg cartons to pack a coop, and Tazo earl grey never tasted better. Tumblr was – privately – awash with my words.

Then I went on a week-long business trip, followed by another three-day conference. Followed by a holiday weekend. …Excuses! I know.

The reality is that my routine – my pleasure association – couldn’t keep up. My trips took me to the East Coast, where my jet-lagged days started three hours earlier. I had only been waking up early for three months; there were still days when waking up at 7am was really, really hard, let alone 4am.

Given the choice of sleep, I simply chose to give up my new writing habit.

This calculated decision spared me from too many guilty feelings, but it didn’t give me any more control over regaining the writing habit. I came back home still a bit sleep-deprived, and also a bit friend-deprived. I continued to choose sleep and even socializing, over writing. Before I knew it, the two-week hiatus turned into a four-month hiatus. I was off the wagon.

Publish this post

What kept my habit from completely dying out was the knowledge that I had found a hack that works – undoubtedly, irrefutably works for getting me into writing. It was my unique combination, that if I just did it again, I would be well on my way to:

  1. Writing my thoughts down in a consistent manner
  2. Editing them in a way that would make them “good enough” to share with others.

I was no longer stuck on “How do I do this?” I had my routine.

So I started again. I cleared a few other life distractions, but really it just came down to doing it one day. Without much fanfare, I found myself up at 7am and decided that I hadn’t had eggs in front of my window in a while. I set the timer for a 12-minute boil. I woke up my laptop. I opened Ommwriter.

Live / Work

How to Care About Everything

January 20, 2015

Finance doesn’t excite me one bit. Hell, even Economist subscribers don’t spend their time pouring over index funds. Or healthcare reform clauses, government spending, call logs, or utility bills. Yet these are all subjects I became intimately familiar with for my work. And guess what. I learned to love all of them.

The biggest part of loving your job is caring about what you do. Being present. It’s on you to stay interested enough to avoid zoning out on conference calls, or cross off every task but the project itself (a.k.a. that time I cleaned the bathroom to avoid writing user stories).

There are tricks to being present. Focusing directly in front of you. Minimizing interruptions. But the best trick of all? To actually care about the details streaming into your ears.

Here’s how.

Connect the dots

What are you hearing now that can be turned into a “hey did you know?” later at dinner, or a “did you think of this” in your next meeting? You’re exposed to many different people with lots of different interests. Do you work with multiple clients? What are your friends and coworkers doing?

I once worked with a bank that offered tiered customer support – the top spending clients got to talk to the senior-ist of support teams. They still employed a lot of analysts, which kept the experience for everyone else from being awful. But still, the bank knew how to prioritize. At the same time I worked with a startup. Unlike the big bank, the startup’s finances were more strapped. Could the idea behind tiered customer support help these entrepreneurs focus on building logic that benefited their bigger accounts? What about putting the senior engineers on the enterprise features, since these customers would likely be less forgiving of bugs?

Of course, you can’t be giving away the secret sauce – there’s NDA’s for that. But every conversation you have exposes you to new concepts that can help other people in unexpected ways if you can train your brain to make the connections.

The human interest angle

Great reporters know how to find the thread in a story that tugs at your heartstrings, makes you angry, or incites your curiousity to read more. When I started working with hedge funds, I didn’t know that a distinct event like the earthquake in Chile could have a global impact on trading and economy. Chile was the world’s largest producer of copper, and also renowned for its salmon industry. Prices for salmon dinners at home rose as the money went back to Chile’s recovery efforts from the wreckage.

This is why the Whole Foods salmon was more expensive that week!! .. maybe.

Working with defense spending, I found myself staring down sheets and sheets of rounded decimals. Calculations had to be triple checked because an .001 off was a billion dollar mistake! What made it interesting was what the dollars represented. Nuts and bolts. Intelligence systems. Sensors. Propellers. There are thousands of parts that go into a jet plane! And jets are cool.

Still bored? Think of yourself

Forget work for a minute. How does this thing apply to me? I have ideas! And bank accounts, and health insurance, and utility bills! Is there something here that could benefit me?

One of my best friends in college was a medical student. As he went through his years of self-inflicted all-nighters, I listened intently to everything from chief surgeon politics, to worries about bedside manner, to how residents flirt with nurses. I never stepped foot in that world outside of these dinner conversation at Outback over blooming onions. But all of those stories prepped me for my own career: knowing when to be humble and suck it up, minding how I come across regardless of how qualified I am, and… well, the stories about the residents were just fun.

This post was originally written in 2014 and published in January 2015. Here’s why!


Email Mirroring: to Emoticon or Not To Emoticon?

January 11, 2015

Lean in. Lower voice. Get louder. Cross your legs. Over the course of a conversation, we mirror the other person’s behavior without even thinking about it. These cues signal that we’re on the same page, that we’re communing. It helps us bond, kind of like a contagious yawn.

But how does one commune in this way when most of our work conversations happen over email and chat? Especially when working remotely with colleagues, we need to develop a new layer of communication signals to replace our usual arm crossing and emphatic nodding.

We already do this. You have an email “voice,” and so does everybody else. You notice it especially when someone’s email is abrupt, or extra effusive.

What you’re saying and how you’re saying it

We infuse “body language” into our emails in three ways: format, length, and tone. Do you always include a greeting and sign-off? Do you use whole sentences, or phrases? Are your emails short, or verbose? Do you say “thanks,” or “thanks!”?

We unwittingly tack on extra meaning when we read emails. Think back to the last time you received a one-liner. Unless it was either “You rock!” or okaying sandwiches for lunch, it sounded rude to you, right? No hello?! No “thanks”? What else do you “hear” when you read emails from your colleagues, your boss, your clients? Is there a “please” in there? Is it condescending, frustrated, or polite? (Hint: it’s rarely just polite!) Can you count the number of exclamation points and smiley faces?

Look, we’re bonding!

Now that you’re aware of how you’re coming across in emails, you can wield that into better communication with your colleagues and clients. Let’s start simple: don’t overdo it on the exclamation points if your newest client only gives you terse all-business replies. But oh wait, was that a smiley face in your favorite customer’s response? Lob one back. Maybe even a wink that says “you know how it is!” if you’re feeling cheeky.

You can mirror your recipient by keeping your emails short and to the point if they always seem to be in a rush. If the emails you receive are warm and familiar, feel free to loosen the formality of your language.

Here’s a scale:

  • Frigid: “No. Will email.”
  • Formal: “”Dear Sir, Please find attached the document you requested.”
  • Respectfully human: “Here’s the document, as promised. Let us know if you have any questions.”
  • Warmer human: “Here’s the document, as promised. Let us know if you have any questions!”
  • Familiar human: “Here’s the document I mentioned. Hope you had a great time in the Bahamas!”
  • Too familiar: “Here’s that document, talk soon!!!! xo” (don’t do this)

Adjusting the tone, length, and structure of your emails is just one way to mirror colleagues when most of our conversation is funneled through a computer screen. And just like in the physical world, you’ll naturally find that you speak one way to one person and another to the next.

This post was originally written in 2014 and published in January 2015. Here’s why!


I Don’t Want to Sound Like a Robot

January 5, 2015

I sometimes worry that I’m turning into a robot. Management is a funny thing. You get into management because you care about people and processes and doing things right. But a peculiar threshold emerges as you’re given more people and responsibility to manage. At some point, to be as effective as you can possibly be, you start considering these people and processes as one big organism. Like a 3D puzzle where you have to blur your eyes to see the full picture.

When you blur your eyes, you become a robot.

Why robots are bad

Robots don’t see all the nuances. They skip over complex emotions, like curiosity and frustration. Humans are complicated creatures who have such emotions. A robot can’t inspire a novice developer to learn a new technology, or listen sympathetically to someone who’s venting. When a company is run by robots, souls shrivel up until they become robots themselves.

I met an entrepreneur recently. He’s developing a new tool for developers. His mockup for the home screen ran rampant with unruly code snippets in a million small boxes. Even if I weren’t an ex-designer, I would’ve felt… uncomfortable. He said he didn’t care about fun. He was solving a problem here, a very important one! What mattered was quick access and efficiency!

Wait, did I hear “I don’t care about fun”?

Without fun or curiosity, we stop inbuing fun into our output. And fun is attached to a whole slew of things, like delight, engagement, stickyness, and impact. When we become robots who stop caring about fun, we no longer build products that move people. You want to move people, don’t you?

The Worst Part About Being a Remote Robot

Like many things, being a robot gets exponentially worse when we’re in a distributed team. This is because you are more likely to be seen as just a robot. The number of interactions we have are fewer, and funneled through 30-minute video chats. How you speak will give away that you’re a robot, and there won’t be watercooler jokes or a hokey souvenir on your desk to dispel that.

Signs You’re Becoming a Robot

It starts innocuously enough. You’re looking at bottom line, financials, and you realize that you’re going to have to “cut costs” or “drive more revenue.” In times like these, it’s helpful to see everything in front of you as “assets.” But people aren’t utilities, are they? They aren’t fixed outputs. You invest in them, not knowing whether they’ll depreciate or grow. And that’s the fun part of working with people instead of machinery.

It’s around this time that someone will say to you, “Maybe you’re just not cut out for management.”

Don’t listen to them.

This post was originally written in 2014 and published in January 2015. Here’s why!

Communication, Management

Why The Future of Work is for Everyone

January 2, 2015

You don’t find much fully distributed working in the wild yet. Maybe in small pockets of startups, and some consultancies. But in 2014 “remote” still meets with mostly head-scratching. And no, large corporations with satellite offices don’t count. I’m talking work-in-pj’s-if-I-want-anytime-I-want distributed working.

What if every employer, large and small, worked this way?

Imagine the largest company you know – maybe the one where your great aunt Susie’s daughter’s cousin works at. Or maybe it’s you that works there. Imagine if you stopped going to that office tomorrow. You choose your favorite things from your desk (camera lens mug, and framed picture of Fluffy), and leave behind the awkward rolling chair and cheap coffee. And so does everyone else. When new members join the team, they ask you what your home office is like. You train the webcam on your mug and Fluffy says hello from your lap.

Now imagine that it’s you running that company. It’s a scary thought, not having all your employees in one place. A little like sending your kids off to college. What will they do there? Will it even vaguely resemble work?

What’s in it for bosses

There’s the obvious reasons for going remote. If you give people choice and freedom, they are happier individuals. Happy employees are productive employees. Agreed? Agreed. But how is remote distributed teams going to directly impact the “bottom line?”

Not limiting yourself to geography suddenly opens you up to a myriad of talent that previously didn’t consider you because you were not ideally located for them. If we think everyone who has skill and ingenuity wants to live in New York, San Francisco, or London…. well, we’d be wrong. There’s many other perks of setting up distributed, but we’ll stick to exploring this one for now.

Are Consultants Out of a Job?!

If companies were able to hire anyone from anywhere for exact fit, does this mean vendors become obsolete? As managers, we always want to grow our teams but it often becomes overhead in the greater desire to experiment and innovate and throw ideas against the wall. If we need to produce two additional long-term salaries in order to give new product line Z a try, we may not be so bold to take that risk. There will always be room for the fast-moving supplemental team who can insert themselves quickly, get shit done, and leave the company a better place.

On the frontline, there will always be developers and designers who thrive on solving wildly different problems from month to month. On the other side of the fence are folks who prefer to dig deep and grow with one problem, seeing it through its entire evolution.

Why I’m For It

If everyone — and I mean, not just the people in your own company, but everyone — worked the same way, imagine how much we could accomplish by simply skipping over the mundane task of “getting set up.” Part of the reason why programming frameworks like Rails was so successful is because it was “opinionated.” Wanted to add an image? You knew exactly where to put your file, because the framework told you where to put it. And guess what? Every developer picking up your project knew exactly where to find it.

Imagine a world where no one had to ask:

  • “How much vacation time do I have left?” (you take what you need)
  • “Can I work from home?” (yes, you can work wherever you want)
  • “How do we communicate our status to each other?” (daily standups)
  • “Do we influence what gets done around here?” (plannings and office hours)
  • “Is it okay if I try this?” (yes)

There’s any number of aspects of “work” that could be shared in this way, from vacation norms to communication styles to utility of physical spaces. And if everyone embodies at least the intention of those norms, we could all show up to work on the same page, with the same expectations and comforts, enabled to hit the ground running.

This post was originally written in 2014 and published in January 2015. Here’s why!