They forget step one every. Single. Time

I was talking to a good friend and when I asked him how his job was going, he responded with, "well, I've gotten to 'I don't hate it.'" We had a good laugh and moved onto other topics, but since then I've thought a lot about his response. I spend so much time at work that it's nice to have a job I more than tolerate.

The one caveat to this is every job I've ever had--even the ones I've loved--tend to have parts that aren't much fun. But how I know I loved those jobs was because I was willing to do the bad parts because the good parts more than made up for them.

So, basically, all jobs have things you'll hate about them, but that doesn't mean you can't love them. And you'll know you love them when you are willing to do the bad parts so you can get back to doing the good parts.

If you're in a job you hate, you can always take UFC President Dana White's advice:

If you hate your job and you're miserable getting up and going to work every day, what are you waiting for? Do it right now. Don't wait for tomorrow. Half the battle is knowing exactly what you want to do.

Or, if you can't quite bring yourself to quit (there's bills to pay, dang it!), you can at least take The Onion's advice:

I can’t stress this enough: Do what you between work commitments, and family commitments, and commitments that tend to pop up and take immediate precedence over doing the thing you love. Because the bottom line is that life is short, and you owe it to yourself to spend the majority of it giving yourself wholly and completely to something you absolutely hate, and 20 minutes here and there doing what you feel you were put on this earth to do.

Say it in your best Batman voice, 'I'm Batman!'

Carpe diem, peeps!

When I was a kid, my mom used to joke that I never did anything more than once, If Jay wasn't good at something right off, he didn't want to do it anymore, she would say. I, of course, didn't appreciate her good natured ribbings and wasn't shy about letting her know it. She, of course, would point to things like my one season of T-Ball1, among others, to counter my whining.

It wasn't until much later that I finally stumbled on why I took such offense to her categorization of me as a quitter. It wasn't because I wasn't a quitter, I genuinely quit a lot of things, so my mom had a point. No, the difference was I thought of quitting those things as eliminating distractions so I could focus on spending my time doing things I enjoyed.

For every one season of T-Ball there were multiple seasons of soccer. Behind every discarded toy there were hours spent building crazy lego creations. It was true I didn't have much tolerance for things I didn't enjoy, but when I found something I wanted to spend my time doing, I could dedicate hours to it a day.

I bring this up because it lead me to notice a pattern that largely dictates my happiness with certain parts of my life and my desire to stay engaged with those parts. Basically, every interaction I have with someone--or something--goes into a bank account, and positive experiences increase the balance of that account, while the negative experiences subtract from it.

The trick is, as long as that account stays positive, I don't mind spending my time there, but as soon as the lows start compounding faster than the highs can offset those losses, I tend to get anxious to quit and move on.

It's similar to the hedonic treadmill Barry Schwartz talks about in The Paradox of Choice:

In the same way that we each have our own internal thermometer for registering sensation, we each have a “pleasure thermometer,” that runs from negative (unpleasant), through neutral, to pleasant. When we experience something good, our pleasure “temperature” goes up, and when we experience something bad, it goes down.

People fight, I've had fights with my parents, siblings, wife, and child. Yet, I still talk to my parents and my siblings, my wife is still married to me, and my daughter is, right now as I type this, chilling next to me2.

This is why I can get into an all out yelling, screaming, fight with a member of my family on one day and be perfectly normal the next, because even though we just experienced a low point together, the highs are always so much higher that the account isn't even close to going into the negative.

This also explains how a smart, opinionated startup team is able to move past intense arguments about the product and still function as a team, be happy, and get stuff done. I've experienced working environments where the highs no longer tipped the balance into the positive and one of the biggest regrets of my professional career is I let the balance get more and more negative instead of moving on right away3.

  1. To be clear here, I really hated T-Ball, I only lasted one season not only because I wasn't good, but because I had no desire to become good, and that was the problem. 

  2. What's interesting about my daughter is that in the first moment I spent with her, when she wrapped her little hand around my finger, her bank account balance went so high I'm not sure she could ever dip to a negative balance, no matter what she does in the future, hopefully she won't test that though. 

  3. I've also watched good friends' companies descend into madness and ultimate failure because the lows kept going lower and lower each and every day. 

Right where I need to be in this moment

15 Minutes, that's how much time I wanted to spend just focused on my daughter, Kenzie, each and every day. I didn't choose this number because I thought it was a particularly large amount of time, it isn't. In fact, it felt like a laughably small amount of time and, as it turns out, was even below the average

While the time focused on their offspring still comes in at a fairly low average of 35 minutes a day for working fathers, it is far higher than the five minutes registered in 1974.

No, I chose this number because I thought I could do it, every single day, and that any higher number might be setting myself up for failure. Basically, I was following B.J. Fogg's behavior change advice of choosing a tiny, concrete goal, and sticking with it.

B.J. Fogg, head of Stanford's persuasion lab and his own Tiny Habits, challenged the room to just floss one tooth a day, and if we committed to doing that, then B.J. could come back a year from now, and we would all be flossing all our teeth, the key was we couldn't do less than flossing one tooth, and we had to commit to that.1

I hoped I would be around my daughter for more time than that each day, but these 15 minutes would be different, they would be special, they would be 15 minutes just between the two of us.

Throughout the nearly four years of Kenzie's life, these 15 minutes have come in many different forms. When she was a teeny tiny baby, I spent a lot of nights programming late into the night2, and so after my wife would feed Kenzie, I would take her and rock her to sleep.

When she got bigger I would help her pick out her pajamas, get dressed for bed, and read her a bedtime story.

Now, we watch Phineas and Ferb together each night. She no longer needs my help getting dressed, and when we read our bedtime story, we sound out a word together and as I read the book I point at the word any time I see it so she can read it to me. She's growing up, and as she's gotten bigger, our 15 minutes have changed accordingly.

I remember one of my professors talking about why he quit his job as a senior executive at a big technology company and became a professor. My professor had gone to visit his mentor in the hospital right before he died and while they were talking my professor had mentioned that he had been traveling quite a bit and had recently missed his daughter's flute recital.

Before my professor left, his mentor pulled him close and said, "less traveling, more flute recitals" and my professor took that to heart, quitting his job not long after.

We went to Kenzie's first dance recital last week, and I definitely can't wait to go to more of them. I'm also looking forward to spending 15 other minutes a day with our second child, who will be joining us in the not too distant future.

  1. This is adapted from my own notes from a talk B.J. gave. 

  2. or early into the morning 

Neil Armstrong and Buzz Aldrin pray while in quarantine

Mad Men's penultimate season ended a few weeks back and the prominence of the moon landing in the season's final episode inspired me to go back through my Evernote quote notebook and excitedly share some of my favorite quotes on the moon landing and exploration with my wife, and I figured why not share them with all of you also :)

The first is from Apollo 17 astronaut Eugene Cernan on Going to the moon:

"The truth needs no defense. Nobody can ever take those footsteps I made on the surface of the Moon away from me."

President Obama mentions going to the moon in this great speech to Wakefield High School in Arlington, Virginia in 2009:

The story of America isn’t about people who quit when things got tough. It’s about people who kept going, who tried harder, who loved their country too much to do anything less than their best.

It’s the story of students who sat where you sit 250 years ago, and went on to wage a revolution and found this nation. Students who sat where you sit 75 years ago who overcame a Depression and won a world war; who fought for civil rights and put a man on the moon. Students who sat where you sit 20 years ago who founded Google, Twitter and Facebook and changed the way we communicate with each other.

So today, I want to ask you, what’s your contribution going to be? What problems are you going to solve? What discoveries will you make? What will a president who comes here in twenty or fifty or one hundred years say about what all of you did for this country?

Are there any West Wing fans out there? I've always loved this quote about exploration from Sam Seaborn in season 2's Galileo:

MALLORY: we went to the moon. Do we really have to go to Mars?

SAM: Yes.


SAM: Because it's next. For we came out of the cave, and we looked over the hill, and we saw fire. And we crossed the ocean, and we pioneered the West, and we took to the sky. The history of man is hung on the timeline of exploration, and this is what's next.

The last one I have for you is from Stuart Robbins and is one of my favorite quotes of all time:

"If people don't think we were able to go to the moon, then they don't believe in the ingenuity of human achievement [...] Going to the moon and returning astronauts safely back to Earth is arguably one of the most profound achievements in human history, and so when people simply believe it was a hoax, they lose out on that shared experience and doubt what humans can do."

Be inspired! And knowing we sent someone to the moon and brought them safely back, how can you not be?

Update February 2018


So SpaceX and Elon Musk launched a Tesla into space, and this tweet made me laugh...

Hoepfully this fortune is accurate

I spent most of my weekend dealing with server issues caused by having too many people chatting with their doctor simultaneously. While I had no desire to spend my Saturday dealing with our growing pains, it makes me happy to see how far First Opinion has come over the last year.

June first marks one year, to the day, that James and I officially joined First Opinion, so I thought I would take a moment to reflect on what a great year it's been. We talk a lot at First Opinion about building the last company any of us will ever work for and so I hope to be writing these each and every year from here on out.

I spent most of 2012 obsessed with disrupting health insurance. I had never worried about health insurance before, being male and single, and I had insurance from Plancast for the entire life of my daughter and most of my marriage, so I hadn't ever had to switch insurance, until we sold Plancast and I finally experienced the reality of a life without company sponsored insurance and the nightmare of getting adequate private insurance. It. Is. A. Pain. So I started researching, quite, a bit, about the healthcare industry, looking for an opportunity in the space.

I eventually decided attacking this industry was outside my current ability. Then I received an email from McKay saying he was leaving to start another company in the healthcare space. I remember leaving that first meeting with McKay, after he gave me his pitch, thinking holy crap, he's figured out a way to give everyone access to a doctor

McKay and I talked nearly monthly after that while he tested and refined his original idea, bouncing ideas off me as he was shaping the core principles that guide First Opinion to this day. Towards the end of April, he called me late one evening and asked me to join him as co-founder.

McKay and I had been friends for a few years, and I had always told my wife that I would jump at the chance to work with him if the opportunity ever presented itself. So as soon as he made the offer, I knew I was going to take it, and James was the first phone call I made after I had gotten permission from my wife, and officially accepted McKay's offer. I had worked with James previously at Undrip and I was constantly blown away by the speed at which he moved, and the quality of his final product. I couldn't imagine building an app this with anyone else, so I'm incredibly relieved he said yes.

So now you know a bit about how I joined First Opinion, let's take a look at what we've been doing this last year. We officially began development on the First Opinion iPhone app on June 7, 2013. We released our first public beta to the app store in just three months later in September, it was a low key release whose primary purpose was to begin moving our beta testers that had been using MessageMe for the last six months to talk with their doctor.

James submitting to the appstore on Sept 22, 2013, a little after 1am

We released our first real public version to the app store right before Thanksgiving, which in retrospect might not have been the best idea since most of us left on vacation immediately after. McKay wanted to be very hands on with the matching in the first release. He had recruited each of our doctors personally and knew them intimately. So when a new user signed up, McKay would get a notification, he would look over their details and decide which doctor would be right for them.

And since I was going to be visiting my wife's family, I wanted to make sure those matching notifications were rock solid, because if McKay wasn't getting notified, the user wasn't getting matched with a doctor. So I rigged the server to send an email, a text message, and a push notification for each new user that signed up.

Over the next couple of days, First Opinion steadily climbed the app store rankings, moving into the top five apps in the medical category, and McKay's phone blew up with notifications, three at a time, to the point where he couldn't get any sleep because his phone was buzzing every few minutes.

McKay, his wife, and Rachel rotated shifts over the next 36 hours matching people to their new doctor while I worked to get an automatic matching algorithm in place so everyone could finally get some sleep. On the flip side, each of our doctors was getting inundated with tons of new users every hour, all with a question or two to ask.

It was a crazy Thanksgiving vacation, but it felt good to have people using, and loving, First Opinion. We blew through our six month goals in about six days, and we parlayed that initial success into a new investment from True Ventures, who joined our other investors to help us continue to grow our vision.

We've spent these last six months moving offices1 and getting better at everything. We've worked tirelessly to make sure the servers are stable, we've released three other internal applications to help our doctors and our quality assurance team manage their growing user loads. We've released our first payment products and we've gotten tons of feedback from our users, sharing incredible stories about how their First Opinion doctors have helped them. We've also learned a ton about what works and what doesn't with virtual doctor consultations.

We've also brought in some adult supervision, in the form of our COO, Vik, who joined Rachel in growing and training our doctor network. With Vik's help we've taken our average response time to a question from hours to minutes.

I'm incredibly proud of the engineering work James, Jarid, and I have done over the last year, I'm not sure there is another team out there that could do as much in one year as we've done. They've blown away my expectations again and again this year and I'm genuinely proud of what they've accomplished individually and what we've accomplished together. I honestly don't think there is a better core engineering team out there at this moment.

I'm also incredibly thankful to be working with McKay, Jarid, James, Rachel, Vik, Ashley, Sarah, and all our incredibly knowledgable and compassionate doctors every day2. I'm also incredibly thankful for our users, each and every one of you3, I love you all, and I hope year two is as fun and exciting as this first year has been.

  1. We have switched offices three times over the last year, and that's not counting the two times McKay and Jarid moved before James and I joined. 

  2. I expect this list to be much larger next year :) 

  3. I also expect this number to be significantly larger next year also :P 

Two roads diverged in a yellow wood

It was just another day at the office when Mark approached me about implementing a new feature for a project we were working on, before he could finish fully describing it, I interrupted him with, "Absolutely not, that would never work and here's why..."

I then proceeded to rattle off a long list of all the reasons why it would never work. Mark patiently listened to my mini-rant and then, with a heavy sigh, responded with something I've never forgotten, "Jay, you never say yes to anything and I'm getting to the point where I don't even want to approach you with new ideas anymore."

Some programmers might wear a response like that as a badge of honor, they might even relish in it, as this commenter on Hacker News shows:

A designer I worked with had lots of interesting stuff taped to his door

My favorite was probably the following:

“Can you just...”


But I had no desire to be perceived as a Negative Nancy like that, and so Mark's response that day completely transformed my attitude about how I approach new feature requests. Now, my default response to most new feature discussions is that of course the engineering team can implement it, it's just a matter of priority.

Some developers will consider this a dangerous answer, but I think if expectations are agreed to ahead of time, most problems can be avoided. The entire team, or company, needs to understand the tradeoffs of the new feature, its ongoing maintenance, and how it affects the overall product.

I snapped this photo at Seeking Alpha's office in October 2017

These tradeoffs are wonderfully summed up in two points of rfc1925:

(2a) No matter how hard you try, you can't make a baby in much less than 9 months. Trying to speed this up might make it slower, but it won't make it happen any quicker.

(7a) Good, Fast, Cheap: Pick any two (you can't have all three).

If everyone understands that anything can be done, as longs as acceptable compromises and sacrifices are made, the conversation can then change from, can we do something? To, should we do something?

I think should we do something is the more important question. If we accept we have the ability to build anything we can imagine, we need to decide if that's how we want to spend our time, because:

Among the most dangerously unconsidered costs is what I've been calling complexity cost. Complexity cost is the debt you accrue by complicating features or technology in order to solve problems. An application that does twenty things is more difficult to refactor than an application that does one thing, so changes to its code will take longer. Sometimes complexity is a necessary cost, but only organizations that fully internalize the concept can hope to prevent runaway spending in this area.

While the author is specifically talking about codebase complexity, I think this also applies to the overall product as a whole, marketing a product that does twenty things is much harder than marketing a product that only does one thing really well, especially if those twenty things span across multiple target markets.

I like to think about product complexity like a magazine subscription. I have packrat-like tendencies that require constant vigilance on my part to keep in check. A few years back I talked my wife into letting me get a magazine subscription, she reluctantly agreed after I told her I would throw the magazine away after I read it.

However, each month I would find one or two things in the magazine that I wanted to remember, so I would mark the pages and put the magazine in the corner so I could reference it later. My three year subscription ended last year, but to this day, there are 36 issues of that magazine sitting in a box in my office.

I can't bring myself to throw them away because I've marked something to remember in each and every one of them, but I also think about how annoying that box of magazines is, and how much space it takes up. That box has even survived a dwelling relocation or two. That's product complexity.

There's a reason why we have platitudes like, KISS, keep it simple stupid! and Good is the enemy of great because we really do need to keep reminding ourselves of what's really important and where we should be spending our time. Complexity in your codebase, and in your product, grows exponentially and can quickly spiral out of control--and paralyze your company--before you even knew there was a problem.

Epic Failing

This last week I missed solutions to two different types of problems, and how I reacted to each type was so radically different that I thought I would take a moment to reflect.

The first type involved new feature discussions in the office. Usually, when the team starts discussing a new feature, one of the first questions asked is how much needs to change in order to support that new feature. My preliminary thoughts on a certain feature was that it was going to involve a lot of infrastructure changes, which caused us to rethink adding the feature at all because of the complexity involved. However, on further discussion, James, proposed a solution involving changing just a few things here and there.

After reflecting on James's proposed solution, he was completely right. I had completely overthought the problem and we really could fully support the new feature with just a few minor tweaks to our existing codebase.

My initial response to this first type of miss was all out pride. This is why I work with smart people, because they see things I don't, and their input makes me a better programmer, working with them makes me a better CTO, and their hard work makes First Opinion a better company.

The second type of problem I missed involved failures in our backend systems. We had two significant downtime issues this week. The first happened early in the week, one of our long running cron jobs had been failing for at least a day due to an input change.

The second happened early Saturday morning (or late Friday night if you prefer) and in my sleepy state I failed to fix the problem on my first stab, and so it stayed unresolved until I was awoken a second time a few hours later.

Both of these issues were caused by monitoring failures in our systems, and my initial response to both of them was disappointment in myself for how bad I had screwed up because neither issue should have ever existed for more than a few minutes, at most.

Programmers screw up, code is brittle and it breaks, a lot. But, because epic level screw-ups are so common in programming, you have to be careful in how you handle discussing the error after the fact, I don't know anyone who enjoys their failures being pointed out again, and again, and again. Likewise, I've never known a programmer who didn't feel just awful after an epic screw up.

Epic Failing

My focus instead turns to solving the issue that caused the epic failure, and to do that, I like to use the 5 Whys to figure out what went wrong, and to make sure the problem is never repeated again in the future. I also drop every other project on my plate until the solution is fully implemented. My team and I are going to fail spectacularly1 again, it's just the nature of software development, but the goal is to never fail in the same way twice.

Supplementary Material

I liked these two quotes from David Sokol, quote one:

We are very tolerant of mistakes resulting from a judgmental error at the planning stage, when despite our team's best efforts, the market zigged and we zagged. It happens. We recognize the error, adjust from it and learn from it. We are not tolerant, however, of mistakes made from a lack of planning or diligence or from plain laziness. Tolerating such situations ultimately makes the organization very good at them.

And two:

Making a decision that delivers a less than desired outcome is part of business life. Failing to take the time to understand your mistakes and learn from them is totally unacceptable.

And this is a great pep talk from the Duke Women's Basketball Coach about how mistakes are part of the game:

During the game some things are going to go wrong it's what happens. If you really like watch the game of basketball, every possession something goes wrong for somebody.

That's how someone scores or that's how someone doesn't score because something goes wrong with every possession.

So there's 150 possessions in a game, 150 times someone's making a mistake. It's part of it so just don't don't let that throw you off. You make a mistake, it happens, but just get back into the play as quickly as you can and then try to make the next right play.

That's really the most important thing about being being a basketball player is when you make a mistake try to make the next right play as many times as you can.

  1. but just to be clear here, both these issues were caused by me, no team needed. Despite some big wins this week, overall, it was a tough week for my programming self-esteem. 

James Talmage, writing in The Great Apostasy:

There is no institution so pure and excellent which the corruption and folly of man will not in time alter for the worse, and load with additions foreign to its nature and original design

This applies to code also and, well, just about everything else also.

I have a very roundabout way of getting to my point in a conversation1, and while my folksy style of communicating would be right at home in an episode of The West Wing, it seems to be a real problem for me in the real world. I don't know why I just can't seem to take Xenophon's advice:

Brevity is the soul of command. Too much talking suggests desperation on the part of the leader. Speak shortly, decisively and to the point [...] Then move on.

I also would choose to be considered witty over tedious any day of the week:

Therefore, since brevity is the soul of wit
And tediousness the limbs and outward flourishes,
I will be brief


I first realized this was a problem in my chosen career path when I attended my first meeting with Plancast's investors. During the course of the meeting, one of our investors asked me a question about how I was planning on hiring more engineers. I began answering the question with a wonderful story about engineers with the intention of segueing into my answer about how we would like to allow prospective engineers do a paid side project for us before offering full employment.

In the middle of my story, the investor cut me off and asked me to get to the point. Since then I've mentally noted numerous occasions where people I'm talking with have finished my sentences or cut me off and just moved on. These mental notes have caused a certain amount of paranoia to follow me into any conversation.

This paranoia to be succinct has also infected other areas of my communication, like emails, where my brevity has led to, on numerous occasions, omitting crucial details the recipient actually needed to clearly understand what the heck I was talking about. Alas, I'm just not good enough to paint gorgeous word pictures as succinctly as Hemingway2:

For sale. Baby shoes. Never worn.

And since I'm often so short on time, I feel like my communication tends more toward that of Blaise Pascal's than not:

I have made this longer than usual because I have not had time to make it shorter.

I guess my point is you should be succinct, but not too succinct that you leave out crucial details or waste too much time dialing up the brevity, something I struggle with daily3. I will say though, I think Twitter has really helped me deliberately practice being more succinct, but I've still got a long way to go. And if I ever do get it right, I can finally leave them wanting more.


  1. One of the reasons I decided on a one blog post a week goal for 2014 was to work on this problem, writing allows me to edit and revise my thoughts to get to the point in a way that conversation does not, and I'm hoping improved putting thoughts to words on a page will eventually bubble up to improved thoughts to mouth. 

  2. Or Not 

  3. this sentence is the tl;dr version of this blog post, yet I still added 400+ more words :) 

So Google+ may or may not be dead. Either way, Vic Gundotra moving on can't be anything other than a huge blow to the social networking also ran. Now we'll just have to wait patiently to find out if his departure was a fatal blow or not. I really liked this Danny Crichton's piece on the early days of Google+:

"In many key ways, Google+ was ahead of its time. Its internal product focus was on choice and privacy, which Google felt was the competitive advantage needed to beat the incumbents. It was reaching out to a demographic of users who had been turned off by the news about personal information leaking on Facebook, yet who were still interested in engaging socially online.”

His whole piece was a great look at the internal politics of launching Google+, but while Google+ was a lot of things, it was never ahead of its time. Sure, it had some novel video and grouping features, but they felt more like Google's take on similar solutions from other companies, rather than any real envelope pushing innovation in the social networking space. In fact, its launch in 2011, really made me think of this famous quote from Wayne Gretzky:

I skate to where the puck is going to be, not where it has been.

Google+ was, without a doubt, what Mark Suster calls a "puck at your feet" response to Facebook's meteoric rise to prominence. A Facebook clone that wasn't nearly as good or useful as Facebook itself. In many ways, it reminded me of a less successful version of Microsoft's late nineties attack on Netscape Navigator1 with the launch of Internet Explorer. Microsoft correctly identified the future was the internet, and they definitely identified that you got to the internet through a browser, but they incorrectly focused on the puck at their feet (the browser) and missed the direction the puck was moving (the cloud).

What if Microsoft didn't bother with a web browser, but instead moved to own the internet outside of the browser? Imagine if Microsoft focused all its energy on the kind of collaboration the internet makes possible, if multiple Windows computers could easily sync their folders and files together (a la Dropbox) and if multiple people could easily edit shared Microsoft office documents simultaneously (a la Google Docs), all outside of a web browser. It would've been a much different decade for Microsoft if they had started it with easy syncing and collaboration throughout their entire Windows and office products, that would've been skating to where the puck is going to be.

Google reacted in the same way Microsoft did, just less successfully, they both thought they saw the future, but what they really saw was the present. Kudos to Google for recognizing it faster.

The predicted unbundling of Google+'s best features, like Hangouts and photos, follows Facebook's continued unbundling strategy. Both companies are now skating in the same direction to a mobile future of small focused apps that are loosely connected on the backend. It should be fun to watch the rest of this game play out.

  1. And Opera, don't forget about Opera