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Live / Work

I’ve been a designer, caterer, and product manager. I never stopped coding.

July 20, 2016

In ’96 I was doing bad things to perfectly innocent websites. Navigation menus flying out to greet you on every page load. Full-page backgrounds of my face, made “artistic” with a gaussian blur. Blinking scrolling text! I taught myself every “How to write HTML” tutorial from Webmonkey and experimented ruthlessly on my little webpages hosted in Geocities’ Sunset Boulevard. AOL dial-up brought the world wide web to my sleepy suburban household and I was hooked.

I didn’t think of my hobby as “computer science.” That’s what old men with lab coats did at NASA, right? THIS WAS THE WEB, BABY, and I was hacking my way through it.

I haven’t had a title resembling “Web Developer” or “Engineer” in almost a decade, but I’ve still written code in every job I’ve ever had. It’s a practical skill I’ve held on to, and the single reason I can point to for being smarter and faster at solving problems. That’s why everyone should learn to code, even if it’s just for three months.

1. I got really fast at looking up answers
Coders now have an incomprehensible amount of reference material to solve any problem from how to add 1+1 in Javascript, to how to speed up their petrabyte database. We owe this to the oodles of fellow coders who give away their hard-earned knowledge on sites like StackOverflow.* All this shared knowledge, combined with lightning fast browsers, means we no longer have to start from zero. Let’s say you’re building an app that tells you when your trendiest hipster restaurant has open reservations. If you break down that problem into Google-able little pieces, you will find several posted solutions for:

  • How to scrape a webpage for information you want
  • How to evaluate whether “11:30pm” falls within an acceptable dinner time window
  • How to text “Book now sucker!” to your phone from your app

* Which, as a side note, is amazing; want to look at a culture to emulate? Look at the hacker culture.

The answer might come in Ruby when you’re coding in Python, or meant for scraping puppy adoption websites instead of State Bird Provisions….but that’s why it’s up to you to apply the answers. And since not every answer is good, you also get quite adept at sniffing out the duds.

Why is this applicable to pretty much any aspect of life? Because you don’t know things, all the time.

  • Where is that great date-night spot you just heard about? Look it up.
  • How long does it take for a bursted balloon to decompose? Look it up.
  • How do you change your tire? Go search YouTube.

After three months of coding, you will do every single one of these tasks faster than before you started. Why? Because with coding, you are solving bits of problems at roughly 12 per hour, especially when you’re starting out. You don’t yet have the answer accumulated from some past experience, so assume it takes you roughly an average of 3 searches to reach a satisfactory answer for each problem – that’s 288 searches in one 8-hour day! It’s sheer practice.

2. I see all the pitfalls
Occum’s Razor says that the simplest solution is most often the best one. But even if this first idea might be the best, it likely isn’t the most thorough solution. There’s bound to be an “edge case” scenario in which it won’t work well. Coding trained my brain to always think of these less-than-optimal cases. If I’m not careful I’m that Debbie-downer in your brainstorming session who poo-poos every idea. I don’t mean to, I’m just ridiculously aware of every detail.

Here’s a common example from coding: let’s say I’ve built a form that requires you to enter your birthday. I expect everyone to type in something like “5/14/1980” when suddenly my self-greeting-card site goes viral in the UK. I get an influx of “14-5-1980” or worse, “14 May”, which causes everyone to see ugly unstyled “500 error” pages. Why are they putting in weird dates and strings when they’re supposed to be putting in numbers?! Are they just messing with me??!!

This is when I learn to separate a date form into three fields, neatly labeled “Month / Day / Year.” Yeah. With every ounce of coding experience comes a myriad ways in which things can go wrong, which is nice to learn…. most of the time.

3. Steadfast Technician, not Mad Scientist
There are two kinds of problem solvers. Mad scientists who test seemingly random ideas and hope that one works; and technicians who methodically tease out a diagnosis then fix accordingly. Coding has taught me to be a technician. Not only do I have the patience to nudge here and poke there to better understand the problem, but I also firmly believe that if I follow these steps with patience and reason then I will find a solution. Though this isn’t always true in the real world, it’s true more often than not. No, laundry gnomes did not steal all your left socks. If you work backwards, you’ll remember that you placed your towering laundry basket on top of the washing machine to turn the doorknob, and hey! There’s the sock in the gap between the dryers.

Bonus Reason – It stays with you, like riding a bike.
Last fall I re-upped significantly in my coding cred. But before that I was writing code for a quarter of my time at best. I had a side project at my previous work that I contributed to, and dry-spells for several months with nothing at all. Coming back from that two years was surprisingly easy, like riding a bike.

Even if you stop after three months of trying coding, it’s not a waste of time because that way of thinking stays around. When I have the need to code again, the methodology kicks in so that I have an easier learning curve. It extends to learning other coding languages too. I was surprised that coding was easier after being away for two years.

Is coding fun?
The joys of coding are debatable. I, personally, enjoy the logic and predictability of programming. There’s a reason why they call different forms of coding “languages” – much like learning English or any foreign language, you acquire building blocks like nouns and verbs which you can assemble together to form sentences. And with those sentences, you form speech! I read a page of script just like I would read a book. Sure, when you master those sentences like writers do, you can get pretty creative with language – double entendres, metaphors, similes. But you’re able to manipulate these things because you know that when you string a noun and a verb together, it produces a coherent idea.

But not everyone’s a writer. And not everyone’s a programmer. It just might not be your thing.

Do it anyway.

Communication, Live / Work

How To Say You’re Busy, Part 2

October 1, 2015

This is the second post in a two-part series titled “How to say you’re busy.” Missed Part 1? Check out the “Different Types of Busy” here!

The biggest mistake that everyone makes is not saying it at all. There’s a couple goblins going on here:

  • Fearing repercussions (like getting fired, which is unlikely)
  • Pride (I got this! I can do it!)
  • Naivete (I got this! I can do it!)

Keeping mum about how overloaded you are is the biggest barrier you can put up to successfully surviving this shitstorm. But how you say it is important too – you don’t want to just blurt it out.

So the first step is to know how you’re feeling about the busy. You probably felt overwhelmed and anxious when you first realized how busy you are. Then maybe anger, either at yourself or at whoever loaded up that list of yours. Where you want to arrive at is something like defeat, but without all the crummy loser baggage that goes along with that word. I like to call it: catharsis. This is where you accept your situation, realize that blaming anyone is not going to solve the problem, and you’re ready to hunker down and tackle the work. This is when you ask for help.

Asking for help isn’t the same as delegating tasks. It’s as simple as saying: “Miss Boss-lady/Dear Spouse/Kids/Co-workers: I’m really busy.”

You went through those steps of catharsis, right? That means that this did not come out stressed, or angry. It should come out like an observation, like how “It’s raining outside” might sound. It’s a little bit of a bummer, but you’re sharing useful information that should be pretty relevant to the person listening.

So what kind of help can you ask for? Help can be as simple as understanding — asking for your partner to not get mad at you for being absent over the next several days, and to respect your need to get things done by staying out of your way.

Help might come in the form of lending you a hand in non-related parts of your life. Got a huge work deadline? That doesn’t magically make the dirty dishes at home go away. But asking for help can.

Help could be a second brain coming up with creative solutions to either lessen your to-do list, or to work smarter and more efficiently. Decide whether you will likely benefit from this type of brainstorming, and cut it off quickly but graciously if you’re sure that the busy is already as un-busy as it can be.

Finally, share your plan. You have one, right? Even if that plan is just to not sleep and work all week, share it so others can adjust around you and come up with their own ways to mindfully support you. And then work. Work your butt off. So you can get back to un-busy again.

Communication, Live / Work

How To Say You’re Busy, Part 1

September 17, 2015

I follow a blogger, pretty well known, who writes life productivity stuff. For weeks he had promised a Big Article. On this week, he still hadn’t written it. He wrote a different article instead but clearly felt bad about not writing the one he had promised. But instead of apologizing, he complained. He complained about how hard writing Big Articles was, how much Life gets in the way, and that it may or may not be coming who knows ahhh I pretty much give up why try.

Now I’m a big fan of this writer. But really?

“Busy” is universal. Everyone knows what it’s like to feel busy. Often it just means there’s a thing we really don’t want to do, so we fill up our time with everything but that activity. Those times I can’t help you with. But the real Busy is about acknowledging your limits, apologizing to anyone you’re about to break a promise to, and asking for help.

But first, the three different states of “busy”:

“Delusional Busy”

(i.e. procrastinating) This happens so often that it deserves to be included here. It’s seriously 80% of “I’m so busy” syndrome. You feel busy because you’re filling up your time with a lot of activity, but are each of those activities necessary? Do they contribute directly to the most important goal in your life at the moment (e.g. lose weight, more time with the family, change jobs)? I guarantee you that twenty minutes on Facebook, does not.

“Unpredictable Busy”

(Uncertain territory, didn’t have the tools/knowledge to properly predict upcoming obstacles) Unpredictable busy happens frequently when you’re embarking on something new. Based on the little information you have, you (formally or informally) create a plan. Then when you go and carry out that plan, so much new information comes at you that you can’t adjust your plan quickly enough. Hence the all-too-familiar feelings of being overwhelmed and underwater.

The best thing you can do under this type of “busy” is to remain calm as you can, and set your own expectations that you will be overwhelmed. Remember that everyone goes through this at the beginning.

“Actual Busy”

(Too much needs to get done in not enough time, and it’s all important) Actual Busy is the toughest, because you can’t reason it away. Sometimes, you’re truly no-working-around-it busy. This is the pull all-nighters, forget to eat, miss birthday parties, haven’t talked to anyone in days kind of busy. This shouldn’t happen more than, say, a few times a year (for your own healthy and sanity, but also for the quality of your work), but it does happen and that’s normal too.

Before you follow the next steps, point a critical eye towards your busy task list, and question whether every item belongs there. What if it’s pushed out just one week? Is there technically someone else who can do it, even if they can’t do it as well or as fast?

Ready to let it out? Click here to read Part 2 of “How to say you’re busy”!

Live / Work

Dream Jobs Are Nubby

June 10, 2015

I suspect there are two types of “dream jobs.” One is clearly identifiable, charted by a 4-year pre-professional degree, followed by a 4-year training, followed by a 2-year specialty. And voila, you’re an orthopedic surgeon! It might not be a university track but these dream jobs have names. When you say “fireman,” nobody looks at you funny.

Then there’s the nubby dream jobs. They don’t have sharp edges and clearly defined silhouettes. They slip and slide between vocations, and inhabit the hidden crevices of all of them. They start as an amoeba, but amass heft and stretch into fifty directions as you see more and do more. They expand. There are days when I can barely contain this dream job in my imagination.

This post is about the nubby dream jobs.

How does one prepare for this nubby dream job, if there’s no prescribed training program? How disappointing would it be if suddenly your dream job appeared and you weren’t yet qualified?

1) Your dream job molds to you.

The truth is, if something appeared in front of you — not an offer, but say, a newspaper ad — that seemed perfect but out of your league, then this is not your dream job. It is an aspiration. You may use it to guide the work that you do now, but it is not your dream job because it is not meant to be yours at this time.

2) Your dream job changes.

What brings you maximum professional joy in your twenties may no longer do the same in your thirties. This is a good thing, it means you’ve been giving it your all. Which, congratulations, it probably means that it was indeed your dream job! When you give a lot, repeatedly, that energy depletes and what you desire to give will start to change ever so slightly. You get good at giving that thing, and so you will crave more challenge.

3) Your dream job is many jobs rolled into one.

Unless your dream is to follow in certain footsteps – doctors, lawyers, writers, plaster mold makers (all great professions!) – then your dream won’t have existed before. Not with its exact shape and innards. Because how could anyone have predicted all the individual facets that make you, you? If your dream job is to find work that hits all your buttons, then you will have to cobble together your own job from all the experiences that have spoken to you, and present it to someone — an employer, a market, an institution — and hope it speaks to them too.

It is not a job unless it is sustaining you financially. But it is not a dream job unless it is sustaining you spiritually.

Someone recently asked me, “How have you done so much?” (I’m relatively young). I replied that I started early, but in reality I said “yes” to many jobs and experiences — some paying very little — because I saw in them some semblance of my nubby dream jobs. Web designer, startup founder, event coordinator, pop-up chef. They weren’t the dream jobs themselves, but they possessed some quality that would prepare me should that dream job come.

Communication, Live / Work

How I Use 750 Words to Write Daily-ish

March 3, 2015

If you’re trying to start a writing habit, you have to try It’s a site that gives you a blank canvas to write in, tracking which days you wrote. The implicit goal is to reach 750 words every day, but it also gives you points just for writing. A running tab shows your record for the month: bright green x’s for 750 days, half an “x” for less than 750, and sad empty boxes for days you didn’t write at all.

Seeing those empty boxes sucks. The achiever in me wants to check all the boxes.

750 Words is free to try out, then asks you to become a paying member after 31 days. When my one month anniversary arrived, I didn’t hesitate at all to enter my PayPal creds, whisking $5 a month to Buster and Kelliane who run the site.

I really like 750 Words.

How To Use 750 Words

Prior to 750 Words, I was a fairly longtime patron of Ommwriter, a fantastic desktop app for distraction-free writing. The one-time fee for each major upgrade bought me a gorgeous lush backdrop in which to write. Ommwriter doesn’t have any tracking or motivation features, which is why I was tempted to give 750 Words a try.

Full Screen Mode

The feature I missed most from Ommwriter was the full-screen obliteration of all distractions. 750 Words has a “Full screen writing” option but all it does is hide the top site header. What I really needed to escape from was the clock ticking at the top of my desktop. To get away for reals, I use the full screen mode of my browser (Apple-Shift-F for the Chrome users), gloriously transporting me to a blank field of snow once again.

Writing Music

The other feature I missed from Ommwriter was beautiful soothing writing music, which I had never listened to before while writing. This music is a cross between electronic downtempo, ambient, and spa music – the kind you’re played whilst getting a massage. It gives me the comfort of noise without stealing me from my thoughts. Ommwriter comes with seven built-in soundtracks, all surprisingly well chosen. To mimic this, I found this wonderfully curated “Writing Music” playlist which I listen to on shuffle in a separate tab. The tracks never get tiresome thanks to the “Radio” feature available on most music streaming sites, and I get the added benefit of broadening my music horizons.

You Win! Good Job!

750 Words congratulates me when I hit my 750 word mark, popping up in the top right corner of my screen. There’s exclamation points! This little green notification is enough to keep me writing, especially when I start flagging around 525 words.

When I’m able to push past my blockage, I almost always well surpass 750 words, logging around 1,000-1,500 words by the time I sit back. 750 is enough to get me on a roll, forcing me to dig deep-ish on my topic and therefore tap into a meaning that’s worth excavating. Once I find that second wind, the words fly by.

There’s no grammar nazi or lit police judging your 750 words; the point is just to put words – any words – down onto the canvas. Inevitably with enough repetition, those words begin to better and better resemble the shape you want them to be.

Metadata and Quantified Self Redux

As if the perfect writing environment and auto-save weren’t enough, 750 Words appeals to the geek in me. By entering all-cap labels followed by a colon, I can track various metrics around my writing health. My writing is really a representation of how well my noggin’s functioning, so I like to pay attention to how much I’m sleeping and my own perceived quality of the writing I’m doing (i.e. is it blogworthy). To this end, 750 Words provides a lightweight hack for measuring any metric I want, as long as I can come up with a pithy tag for it. The values are then plotted on a time-based bar graph in my “Metadata” section. Here’s an example of the custom metrics I track:

NAP: 0
SLEEP: 7.5 hours

My writing canvas is one of the few repositories I visit consistently every day, so it’s the most fitting place for me to enter metrics about myself. It’s worked so well that I’ve begun to use it for tracking non-writing related stats like job satisfaction.

I’m certain that if 750 Words wasn’t such a joy to use, my writing goal would have suffered quite a bit. Combined with my offline hack to make writing (and getting up early) as enjoyable as possible, I’ve habitually written enough now to believe that this just might stick.

I discovered thanks to this thoughtful Medium post on starting a daily writing habit by OneMonth’s Mattan Griffel. Thanks, Mattan!

Live / Work

Career Lost and Found, Part 3: “Why don’t you work for yourself?”

February 3, 2015

This is the third installment in a three-part post on leaving a career I loved, choosing to be unemployed for an arbitrary period of time, and indulging in a heck of a lot of tea and think-time. If you’ve landed here directly, go read Part 1: “Why don’t you take some time off?” first, and/or Part 2: “Why don’t you focus on just one thing?”

“Why don’t you work for yourself?”

This question came not from a friend but from his mother, who happened to be visiting San Francisco. I’ve known Jason for a while, so I also know that his parents have a large part to do with who he is – entreprenurial, driven, humble, happy, successful. You can see why anything this woman said might’ve stuck with me.

The idea of working for myself doesn’t actually scare me. I had taken that plunge when I left my first job to cofound a startup in 2008. Before (and after) that, I’ve worked as a freelance designer and programmer, managing my own business leads and invoicing clients.

So knowing that I could do it, why not do it? With the question nagging at my subconscious, I fell into working for myself almost unwittingly. While exploring my love for cooking, I said “yes” to several catering gigs. I had been doing underground dinners part-time for about a year at this point, so it was a somewhat natural extension. But fielding multiple requests for a personal chef-ing business, making hors d’ouvres for fancy parties in penthouse apartments? To me, this was an overnight success.

What ultimately did scare me was the thought of doing it alone. Technically I had freelanced alone, but that never felt like a long-term calling or even a full-time one. As for going all-in on a business, I wasn’t ready to shoulder all that responsibility myself. In Amanda Palmer’s book The Art of Asking, there’s a juicy part where she tells us:

“There’s really no honor in proving that you can carry the entire load on your own shoulders. And… it’s lonely.”

It’s true. I already had 30+ years of biting off more than I could chew (my dad loves to tell a story about six-year-old me, hoarding piles of jumbo shrimp on my plate to peel later, literally more than I could chew). There was many a time it paid off (I ate all the shrimp), and a few disastrous times it didn’t.

When I hit the crossroads of whether to continue working on my business, I knew it had to happen by either hiring a staff or joining someone else’s. Let me clarify: it is possible to have my own business, if I recruited help. The point was, no more going it alone.


Why don’t you work for yourself? If you’re not already doing it — and you want to — it’s because of fear. Even if you are doing it but have trouble leaving the bed in the morning — it’s fear. For me, it was fear of loneliness. The weight of so much future toil and unknown, with no ally or sounding board.

For you the fear might be inexperience, failure, uncertainty, lack of capital, lack of support network. A whole slew of ghosts and goblins.

This is the question I had the least clear-cut answer to. I finally settled on “Not right now, but maybe someday!” It was an answer I felt good about, because it immediately opened up the awesome potential of learning from others, but didn’t close the door to one day leading the charge.

After eight weeks of “yes;” and more tea, books, and walks than I have ever given myself in the past, I’m moving on to the next step. And I’m excited.

Missed Part 1 and Part 2? Check out the other thought-provoking questions!:

Live / Work

Career Lost and Found, Part 2: “Why don’t you focus on just one thing?”

January 27, 2015

This is the second installment in a three-part post on leaving a career I loved, choosing to be unemployed for an arbitrary period of time, and indulging in a heck of a lot of tea and think-time. If you’ve landed here directly, click here to read Part 1: “Why don’t you take some time off?”

“Why don’t you focus on just one of the things you want to do?”

Most people are lucky if they have one passion. I have two! You’re welcome to interpret this as either a blessing or a curse. This was the line I was telling at various birthdays and meetups:

“I love helping remote distributed teams communicate better. It’s what I’ve been doing for eight years as a project manager. But I also love food and cooking for people. I’m going to explore both!

And so I did.

Doing the “yes” work

For two months I said “yes” to every door that opened, not thinking very much about said door. At times it felt liberating, very caution-to-the-wind(!) Other times it felt like I was using my own arms to force myself off a ledge. I had doubts. Sometimes it was “Do I want to do this?”; more often it was  “Will this be sustainable?” But I pushed those thoughts down and dove into the unfamiliar waters, ranging from murky but manageable to thoroughly terrifying.

A plunge into FoodLand

In two months, I catered dinner parties for over 150 guests. I planned and executed menus for clients as well as my own ticketed underground dinners. Newly “funemployed” I found myself working 15-hour days, almost all on my feet. I was bone-tired, a kind of physical exhaustion I had never felt before. I don’t think you can experience this kind of exhaustion going to a gym, and my years sitting at a computer desk had done precisely nothing to prepare me for it.

I loved it. It was worth it.

The surprise on people’s eyebrows as they one by one bit into a mini molten lava cake! The strangers in cocktail dresses who sought me out in the kitchen, just to tell me how much they loved my Korean beef barbecue. Every morning I woke up sore from hours of standing and prepping, yet hauled myself to the kitchen and willingly stayed there.

After a particularly challenging gig, I calculated exactly how many hours it had been since I slept or sat down for more than a quick break. It was forty. Forty hours.

The schedule was enough to burn me out. Specifically, the way that I had been going about it burned me out. I had some invaluable help in the form of a now-and-then assistant, but my most strenuous shifts were often done alone and well into the night.

Offers continued to come in for holiday parties and private dinners. It helped that it was the holiday season. But my depleting energy meant I felt less and less guilty about saying “no” or not following up with inquiries as quickly as I could have.

That other thing

I met with two project managers on two separate occasions to talk about distributed teams and building software. The texture of those conversations was old-hat. Neither were sold on my ability to help them, and I didn’t follow up. I had the confidence and know-how, but I didn’t have the excitement. Did this mean that I actually didn’t care about remote teams? Had I been lying to myself (and to whole audiences!!) for the past four years??

I was battling with this conflict when I got into a Lyft. I learned that my driver, when he wasn’t driving, spent his days on his headset coaching people all around the country to achieve the life they wanted. He himself had left a successful career in IT to make his own hours, tangibly impacting individuals as far away as Florida. I loved hearing that he was doing “remote work.” It made me proud and excited again that these long distances could be bridged with technology – and more importantly, with initiative. These two strangers committed to dialing a number at a designated time each week, to tell their stories to each other. They found it valuable and fulfilling enough that one even paid the other to keep doing it. I became eager to talk up my own past experience, skills and passions that I had neglected for weeks. For the first time, I found myself yearning for hours spent managing and mentoring again.

What I learned after two months of “yes”

I was afraid, when I started this, that I wouldn’t come up with any answers. I determined pretty quickly that simultaneously feeding two passions would not get me very far (credit to one of my earliest mentors for poking fun at that plan from the outset). And so I feared, that after three months of paying San Francisco rent with a starter business income, I would merely be left with the same uncertainty: what should I do with my time?

I capped the experiment at eight weeks, wildly relieved to have found more answers than I thought possible. I had gathered a ton of information — about these careers, about me, about my potential audience — that I couldn’t wait to shuffle through and organize into A Bonafide Plan. I took roughly another two weeks to sort through my experiences, reflections, and the new questions they generated. In addition to a bit of clarity towards what I should and shouldn’t be doing, I noticed a few other themes from my “yes” trial:

  1. Only things you want will present themselves to you
  2. It’s not one or the other
  3. Good things take time
Only things you want will present themselves to you

It was easy to think “Food chose me.” But the numerous dinner party and personal chef requests came from two habits:

  1. I talked about my food gigs and dinners I had just done all the time. What wasn’t I talking about? Teleconferencing tools and developer meetings. Action begets interest, and interest begets momentum.
  2. I was palpably excited when I talked about my food. I felt proud of the dishes I created and described them lovingly. Often I had the pleasure of talking to fellow foodies who sincerely wanted to hear about each plating of my four-course menus. I was both shocked and humbled by this. I couldn’t fake it if I tried.

I didn’t have the pleasure of turning down lucrative consulting gigs or teaching positions, because I wasn’t asking for them — consciously or unconsciously.

It’s not one or the other

When my eight weeks drew to an end, I actually had not discovered what I should be doing with my time. I learned that I didn’t want to be cooking 40+ hours a week, nor that I wanted to continue working with software teams. Didn’t I have more “yes”-work to do?

I peered closely at what exactly got me excited to cook or put on events. I peeled back to before the eight weeks, when I couldn’t wait to collaborate with teammates across the world. What linked all of these moments was the connection I felt to other people. I was excited by food, and my ability to make it, because it gave me an immensely rewarding way to communicate with someone else. What if I could hone in on that aspect, and align my time doing something that came naturally enough to me that I could sustain it for 40, 50 hour weeks?

Good things take time

It took me over a decade to become a truly good project manager. I spent years fine-tuning my ability to motivate people, break down complex problems, commune with clients, organize teams, and think on my feet. There was still plenty more room left to grow. As a nascent speaker, I could easily have spent five more years sharpening my ideas about team collaboration, crafting my storytelling and teaching abilities, and developing a compelling stage presence.

Come to think of it, I can still do this. That’s the great thing about being in control of your own life. Nothing is off the table.

I was reminded that “good” takes time every time I burned a rice cake or made rookie mistakes at a catering gig. Whatever I was going to do, I would have to accept that it would be another decade before I got really good at it. If I was clever about it, I could repurpose everything I had learned so far to get a head start on the gettin’ good part. But it would still take time. And it would continue. Forever. There’s always more to improve, fine-tune, reinvent. It’s more fun that way.

On to Part 3: “Why don’t you work for yourself?”

Live / Work

Career Lost and Found, Part 1: “Why don’t you take some time off?”

January 26, 2015

This is the first installment in a three-part post on leaving a career I loved, choosing to be unemployed for an arbitrary period of time, and indulging in a heck of a lot of tea and think-time. If you’ve been here before, click here to read Part 2 and Part 3.

When I left my position three months ago, I didn’t expect I’d choose to be unemployed. I’ve always worked. Even when I ramped down my part in the startup I cofounded in my twenties, I taught two courses at an art institute and did freelance programming. For most of my adult life, my work defined who I was (arguably, moving away from this may have coincided with the quitting).

So how did I end up here, racking up free-drink stamps at Réveille Coffee and sleeping nine hours a night?

When you quit a job – especially one that most of your circle knows you loved – you get asked this a lot: “So…what’s next?” There must be something even better, more exciting, to have left a good stable thing (i.e. PAYCHECKS!). I struggled to produce the right answer, one that would unfurrow those brows.

There was no one actually judging me, or even that confused by my sudden jobless state. This was my tribe. They knew me, and were madly excited for me in a way that I hadn’t even yet allowed myself to be. Suspecting that I didn’t have much of an answer (I really didn’t), they started asking questions. Truth be told, I dismissed most of these questions off the bat. Surely I just update my resume and line up the interviews! Right?!

It’s funny how questions can burrow into the back of your skull, metastasizing there until you can’t help but notice that twitching nerve in the side of your temple. What follows are three questions that stuck, and just wouldn’t let go:

  1. “Why don’t you take some time off?”
  2. “Why don’t you focus on just one of the things you want to do?”
  3. “Why don’t you work for yourself?”

“Why don’t you take some time off?”

Folks don’t quit when they’re at the top of their game. I was burned out. I hadn’t decided to quit yet, but I knew I needed to recharge.

A quick history: two years prior I took a month to travel Southeast Asia, but during that time I wrote the first draft of a book… on my work. Six months prior I booked two weeks in Austin, but I spoke at a conference and coworked with friends. I took time off here and there, but it was always days not weeks. Even though I talked the talk of how important vacations were, I clearly was terrible at it myself.

So I planned a four-day trip to the southern coast of Oregon. This was neither triumphant nor headline-worthy. It was. Four. Days. And I spent 20% of it writing a resume!


I finally completed my resume. Then an odd thing happened. Reading it over, I hated it. I was incredibly proud of what I had accomplished, but I didn’t actually want to do any of it again.

….Well, crap.

I wrote back to my two contacts who were graciously waiting to submit my shiny resume to their respective awesome-we’re-so-great-to-work-for HR departments, and told them I had a change of heart. I needed time.

I didn’t know what I’d do, but I had a whole lot of “what ifs” and not enough “done thats.” Which leads me to the second question that kept nagging at me:

Part 2: “Why don’t you focus on just one of the things you want to do?”

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!