The answer, contrary to what one might naively assume, is profoundly simple: stare your employee squarely in the face and say quite plainly and with complete sincerity, “Go fuck yourself.” So long as you do not make the mistake of apologizing, you will be rid of the parasitic worm leaching funds from your company’s precious coffers in record time. True, the conversation (should we elect to elevate this pitiful exchange of syllables to such exalted status) might last a few moments longer — but the fatal blow will have been dealt.

Your employee might apologize for what he or she has perceived to be the trigger for your words, but a swift and confident, “Pull your head out of your own ass insert context specific vagaries here” will dispense this drivel. Your employee may even try to appeal to emotion or to their own misconceived understanding of social norms, but simply remind them that it is their responsibility to cope with your management style, this managerial style is immutable, while subject to constant revision, and that failures to accept and embrace this style will be viewed as open hostility to yourself and to the company. When in doubt, consult the rules for arguing.

I am confident this exchange will not be further prolonged. Your employee may even walk out the metaphysical door without another feeble syllable in their defense.

Now, when is the right moment to deploy this intercontinental payload of confusion, this aggressive-aggressive/passive-aggressive bundle of joy?

Honestly, I haven’t the faintest idea however, it happened to me a little more than a year ago. I have been reflecting up the whole of its story since that time. I wanted to take a long pause to fully process the events in my own mind, but I have simultaneously felt a constant, nagging, nigh oppressive desire to write which I can no longer resist. The time, right or otherwise, has thrust itself into the forefront of my consciousness and refuses to be ignored.

The rest of this tale may have little material value to the rest of the world; though it should prove amusing to some. I learned something. Your mileage may vary.

A few days ago, I celebrated another year at Doctor Evidence (DrE), a company in which I strongly believe. This, by itself, would be an otherwise heartwarming milestone for myself but a triviality hardly worth noting for any readers who have wandered past. The cause for pause at this moment in time is less my own gratitude for passing yet another notch on the yardstick of time than it is for my enormous gratitude to be here at all — and there is ample cause to be grateful.

To appreciate the context, we’ll need some. Rewind the clock more than three years.

The evening sauntered towards its inevitable end. I closed my laptop and called out to my wife. She did not respond. After some searching, I found her soaked to the bone, lying face down on the bare concrete in the carport in the brutal cold of early 2013. I still do not know whether she deliberately or merely accidentally attempted suicide that night, but I knew we needed help. Over that year, I struggled to keep my family together as I tried to solve my wife’s substance abuse. My hubris knew few limits. I honestly believed that I could fix this.

Home life affected everything. By the fall, I was depressed, exhausted, suffering at work. I believe I had my first and only negative review that year after almost 7 years of near constant promotions, praise and loyal, excellent work. When Despair becomes your bedfellow, the darkness knows no boundaries.

Light, I often find, is insurmountable — though the speed at which it arrives in practice is often at odds with theory. Quite unexpected and out of the blue, I received an email from Edan Shalev, (I am very pleased to call him now) my boss. He offered me a job. And not just any job. A chance to work from home; a significant raise; the opportunity to design an entire platform from the ground up. Complete creative control. The chance to save or at least improve human lives. How could I say no?

I felt enormously conflicted. My boss at the time, David Hessler, for whom I have the utmost respect and admiration, once said of me, “You know what I love about you, Christopher? There are only two things in your world: things you’re excited about and things you haven’t discovered yet.” To date, it’s still the best compliment I have ever received. More than the respect and appreciation that David expressed to me then and on many other occasions, he and the whole company had invested greatly in my success.

I do not have a college degree. I dropped out of school and joined the Army. I learned Russian and managed to convince a publisher to let me write a book. I taught myself SQL and Visual Basic (for Applications) on a decrepit military laptop in the middle of constant mortar fire in Baghdad. And David hired me.

Not as a programmer, but as a systems engineer of sorts — providing personalized support to our most important customer. After a year of this, I was bored. I remember walking into David’s office one day to say, “I want into Development.” He said OK and our most senior developer, Steve Salter, began mentoring me. In all the years since, Steve is still the most brilliant engineer I’ve had the pleasure of calling peer and friend — and for all our many arguments and my hotheadedness and my emotional reactions, Steve never gave up on me. Because of this, and perhaps solely because of this, I went from a lowly customer support worker to a senior web developer in about three years.

So, again, I felt conflicted. This was a company that had been exceedingly loyal to me; that had taken great risks on my future; that had trusted me. David’s company was acquired by another in the same week as my decision needed to be made; and, in the spirit of transitions, the decision to leave felt right in the end.

On October 1, 2013 I logged into Doctor Evidence’s systems for the first time from my home office. The future, though distant and elusive to the touch, nevertheless felt as though it exuded a general warmth and soft glow. Working from home, I could directly attend to my family. We had a chance to fix everything. We could fix everything. We would.

My ex-wife walked out the door on Sunday, December 1st, 2013. The last words she said to me were, “I never want to see you, this house or those children ever again.”

My two, most precious assets, my beautiful children have been in my sole custody ever since. The first six weeks were some of the most arduous of my life — and I say this as a person that has survived blanket parties, direct fire, indirect fire, crashes and skirmishes and wars. The first week was the worst. Finding childcare for the kids, when every daycare in Ithaca has waiting lists on the order of months and years, would have been unimaginable without the help of friends and family and friends of family and family’s friend’s families.

Ithaca has often reminded me of my time in Germany. The summers are glorious beyond all human imagining. Surely, the Greeks had Ithaca, NY in their minds’ eyes when they envisioned Olympus. Then six months of winter arrive like an invasion force, snatch the sun from the sky and erect in its place a gloom, impenetrable and complete, leaving it to bear until the forces of Spring can usurp them. Darkness, literal. Real, biting Cold. Unrelenting misery.

But. Light abides. Spring returns. By the first, early glimpses of pure sunlight in 2014, the children and I were doing (if not well) far better than we had ever been before. The work at DrE was exciting and fulfilling.

All attempts at reconciliation with my ex-wife had failed. Uncertain what to do, but certain that I wanted to provide the best for my children, I soon filed for divorce. The legal process is least forgiving to the anxious, and such was the Anxiety that replaced Despair! Still, I was awarded sole custody of the children in relatively short order. The question of alimony/spousal maintenance would drag on until the end of the year.

Until very recently in New York, the question of alimony has been straightforward. The husband pays the wife 30% of his net income for a period determined by the length of the marriage and the wife’s ability to find employment. A plaintiff may argue that exigent circumstances merit a deviation from the default (e.g. the plaintiff has sole custody of the children of the marriage), but the judge has sole and final discretion on the matter.

On December 21, 2014, Despair found me once again at her mercy. The judge granted a narrow exception for the cost of my daughter’s preschool, but otherwise followed the formula. Beginning January 1, I needed to pay my ex-wife 50% of my gross income every month. The very first thought through my head screamed, “Thank the gods you already paid for Christmas!” All of the following thoughts began crunching the numbers. I could find no conceivable path to keeping the house — I would inevitably default on the mortgage. I couldn’t afford the winter heat bill.

Only one option proved viable: default on the mortgage and move in with my parents (basement, to be precise). By the third week of 2015, I found myself a true millennial — occupying some 100–150 square meters in my parent’s basement. I think my kids were stronger than I was through this period.

As an engineering manager for a hugely successful bioinformatics company, there was a huge amount of self-imposed shame in losing my house and moving into my parents’ basement. As a father, I felt an overwhelming sense of impotence in not being able to provide for my children.

Concurrently, DrE was pursuing several high-profile bids for new business, and I felt a certain amount of stress and anxiety around the sheer volume of work demanded internally and from our customers (actual and prospective). At the time, I was extraordinarily anxious (and on all fronts). As a company, I felt that we were promising far more than we could deliver and that what we could deliver would not match the level of quality that I require of my work. I perceived there to be a implicit demand that our engineers work to the bone to accomplish this; consequently, I found myself working 10 and 12 and 14 hour days, working through weekends. I felt weary. Stretched. Thin. Beyond the totality of human fatigue, I had doubts: “Will this company even survive beyond this effort?”


These feelings are incontrovertible, as all feelings are. Feelings are real, of course — but they needn’t be overly burdened with facts. I doubt very much that anything can be done to argue with them or mutate them in any way; however, we can (I hope) process them better in the future. Thanks to retrospection, I can add one hugely valuable lesson to that list of hard lessons that only experience can supply: “Don’t make drastic life decisions when you are living in your parent’s basement.” Variations include:

  • Don’t make drastic life decisions in the middle of a divorce
  • Don’t make drastic life decisions while the bank is foreclosing on your house
  • Don’t make drastic life decisions in the middle of winter in Ithaca, NY


In early 2015, opportunity knocked again — and again, quite unsolicited. A good friend of mine, David Furber, had recommended me to a local company (XCo) as a potential candidate for their next Chief Technology Officer (CTO).

Now the foreshadowing of my clickbait title has finally come full circle. How will our humble narrator find himself quitting in under ten seconds? What new catastrophes await? Who will fool whom? And so forth.

The bait-and-switch, I will confess to immediately. Eight long months crawled past before I found my ten second moment, but nearly every moment of those months I found more bizarre than the last.

I interviewed with Xco’s owners, a husband and wife duo, for the CTO position; and shortly thereafter, they offered me the job. To be even more precise, I was offered a salary. All XCo’s funding came through a series of government grants, and XCo had no formal employees — except the duo, who were defined on the LLC proper. This duo had various other LLCs to account for other revenue streams (public speaking engagements, university teaching, publications), and it was never clear over which any or all of these I was intended to function (in spirit) as CTO. In the end, I was offered a salary to be paid out from a line item in a government grant’s budget, managed by a one of an out of state university’s many extension offices. Loud guarantees shouted that this was all very standard procedure in government/education space, nothing to worry about. The duo assured me that my own budget would permit hiring up to two additional developers in the first year, with an expansion of the team to be expected in the following year.

As someone who has worked hard to achieve everything I have, I find it challenging now to grapple with the cognitive disconnects I allowed then. On a fingernail or two of the one hand, this duo had each been divorced and were living in a joined family. They seemed to understand my current struggles, and they were offering their personal and professional support to help me through my own. They empathized with my predicament. On the other fist and a half, the whole proposal seemed perforated with warning signs. I couldn’t explain why I made this decision.

In retrospect, when someone offers to make you an officer of a company, a few things to have in writing: amendments to the articles of incorporation, access to the company records, documentation of your equity stake, an actual contract between the same company and yourself, a budget, and so forth.

Lacking hindsight, I trusted the duo at their word. I submitted my resignation to DrE and began at XCo on May 1, 2015. The most immediate problem was payroll. Though I didn’t know it at the time, I would not receive a paycheck for four months. Excuses were in no short supply: government grant policies had changed over the last year, new university extension policies on the distribution of grant funds had changed, my line item status on the grant was continually wrong from week to week to week, authorization was needed for my salary, and so forth. The duo insisted that it was my responsibility to negotiate the safe transport of my own salary from the university to my bank account, but they were willing to loan me (at 0% interest) money each month to stay afloat.

I suddenly found myself in the absurdly codependent situation of being wholly: physically and financially, dependent upon these people for my survival.

In the beginning, I borrowed little to nothing. I exhausted my savings first; then I cashed out most of my 401k from DrE. I found a realtor who sold the house before the bank foreclosed, and I landed a little from my half of the equity in the home. Le sigh. Inevitably, I had to start borrowing from them month to month to stay afloat. I would only borrow the bare minimum to pay rent, alimony and expenses, but the debt grew like cancer.

At the time, it did not feel as awkward as it does now in the recounting. Perhaps, in no small part having the anxiety of the foreclosure of the house behind me, the battleground for optimism had once again become to seem ripe for the taking. By August, my alimony payments had dropped considerably. I moved my family into an apartment. We were out of the basement. I did not take the time then to ponder that under nearly any other set of conditions: the house would have sold, that alimony would have become more bearable, that we might not live in my parents’ basement forever.

The absence of any form of compensation was certainly the first demonstration of the emergency broadcast system, running on all devices, all the time. Others amassed in different shapes and flavors.

I had met with the whole team at the end of April, immediately before embarking on this journey. We were nearly 20 in number and spent two full days discussing budgets, timelines, roadmaps and priorities. This meeting was to be one of the tentpoles for my optimism in this new venture: many were joined, a shared vision was present, the group seemed organized, we had a mission.

Little more than a few weeks later, the duo revealed that other aspects of grant regulations had changed. We would be restricted in our yearly budgeting to spending the total sum of the grant divided by the duration of the grant. So, if our grant were $5 and the grant duration were 5 years, our yearly budget could not exceed $1. This completely dismembered the budget discussions and roadmap planning that had occurred a few weeks prior. We had calculated that we could use nearly 60% of the total grant in the first year to accelerate development and partition the remainder for the remaining years. This revelation eliminated my own budget in its entirety.

Shortly after starting, I was left with no budget and no auxiliary means to finance development outside of employing myself for longer hours. Certain nominal expenses, such as Slack and Github, were paid from the duo’s other accounts, but the core infrastructure that would be needed to run our software would be financed from my yet non-existent payroll.

Still, we were deep in research and development. Lightweight servers with low usage (the duo and I were the primary users) are not expensive — the principle of the issue was offensive, but the cost was not burdensome. Optimism, optimism.

The zero balance on my budget became more concerning as I began to wrestle against the practical nature of our 24-hour clock. One developer alone, no matter how gifted, had no chance of delivering against our roadmap on our timeline. The duo was generally insistent that no compromises to feature development or delivery times could be accommodated. At a few points, I found prospective college students who might make promising interns, but the duo insisted that any new hires of any type work without compensation in exchange for letters of recommendation — a practice neither myself or any of my applicants could abide.

Absent any additional hours I could add to the day’s clock by leveraging new hires, the duo helpfully offered to let their high school aged children babysit my own, while I worked longer hours. Ironically, this was always positioned as a sacrifice the duo were making for XCo, and since Irony has no shame nor heeds no conventions, I soon found myself consistently working 12, 14 and 16 hour days with greater frequency than ever before.

Within a few months, we had our next company meeting. The group had shrunk rather considerably. We were approximately 10, down from 20, and were discussing radical cutbacks to the original roadmap. Two months later, we were 7.

The duo began proposing radical changes to our business model: running Kickstarter campaigns, starting a private high school, developing product for companies while the same product (funded by the grant) had yet to be delivered to the university, increasing marketing and sales for their publications. I would get inspired text messages at 4:30am with new ideas. I requested politely that non-critical text messages be deferred until waking hours. The duo informed me that such requests were not “CTO like” and that any Silicon Valley CTO would never complain.

In the last 2 months, the atmosphere began to change radically. Routine weekly meetings were suddenly cancelled, last minute, just before their appointed time. These meetings then magically vanished entirely from my calendar. My own critical Monday meetings with the CEO were suddenly cancelled with terse, “Nothing to discuss this week” cancellation messages.

I began sending email summaries of the tech progress on a week by week basis to the CEO. I would detail the work accomplished against the requirements and try to provide estimates. For lack of better eloquence, I felt weird doing this — and I never had a response.

In the first week of December, I included in my weekly report a summary of all the features that were to be delivered or delayed, based on an aggregate of all my previous progress reports. More suddenly than I was aware possible, I received an immediate response. In ALL CAPITAL LETTERS, the CEO asked who had authorized me to make the decision not to release a feature?

I think I responded politely. I cannot be sure. By this point, to my mind, I continued to be the nominal CTO of an amorphous confederation of promises, backed by travelers checks of dubious authenticity. Still, I was the CTO. If any person in the company has the authority to determine what technology features go into a release to the public, I hope by the gods below that the CTO is one of them. And where were the responses to all the other emails? How could this news be new news? Why were we not talking in person? How is it conceivable for a CEO to send an ALL CAPS EMAIL? Who does this?

I responded that I had informed him of the delays several times over the past 3 weeks but had not had a response. I said that the continued cancellation of our tech meetings only hindered the communication of these critical issues.

More suddenly than before, I received another ALL CAPS EMAIL: “Provide at least three different forms of proof that you ever communicated this to me.”

This was exceedingly easy, but I selected only one. I forwarded him an email in response with delicate golden highlights across my estimates and delivery projections, the dates quite clearly visible.

Less suddenly, but with the hour, I received a final, standard email. “Christopher, my lack of acknowledgement is never acceptance of your decisions.”

I must admit that I was stunned. A year later, and I still have no response to this; but, I was not done. I am stubbornly optimistic. To faults of faults. And loyal.

This whole exchange now as forgotten (or at least distant) as possible, we were a mere week or so later discussing a perceived outage on our website. A customer reported it “down”.

I logged into the site from my laptop, which seemed fine. I have long subscribed to a VPN service, which among other things, allows me to switch which country I am in. This is terribly useful when developing software for the web, because I can quickly switch to Ireland or China or Argentina and see how my web app behaves from that physical location. This also happens to be extremely useful when trying to determine whether something is “up” or “down”. Generally Ordinarily, if users in Germany, Russia, China and the UK can all access your website — your website it “up”. So, I checked. My website was “up”.

I explained that the global round robin had revealed no issues, to which my CEO said, “That’s great, since we don’t have any customers in Russia or China.”

I explained that in this case, this type of error can happen to any user of any app, anywhere in the world. Typically, we tell people how to reset their systems so that they can reconnect successfully — but there is absolutely nothing wrong with our application or our server.

My CEO responded, “Great. I’ll let our customers know that our CTO can’t be bothered to pull his head out of his own ass and fix their problems.”

I said, “OK. You should do that.”

“Go fuck yourself.”

That was the 10 second moment. Maybe my “OK. You should do that” line crossed the line. I don’t know. But the second that I heard those magical 3 words, I knew that I was done.

In that moment, I began to wonder how I had let it come to this. I was paying an Australian developer (as a contractor) out of my own pocket to help meet deadlines. I was working insane hours. The customers to which the CTO had alluded were really just Cornell University college students, using our app to do their homework for classes the duo’s taught there. We had no real users. Our roadmap looked like an Asian buffet — fried chicken next to pizza next to lo Mein. I had been working in the blind — my boss was not just ignoring me, he was refusing to communicate at all. 8 months into this position, and I still had no official position at all. I was CTO on a mound of dirt.

So, deep into yet another December, I realized that I needed to leave. I spent a few days trying to patch up my CV, but I began to feel the weight of despair closing in again. Hiring. Interviews. Finding a remote position. Waiting. Desperation. Then it occurred to me — something that I hadn’t even realized that I had done (or not done). I left DrE on excellent terms. I spent considerable time making sure their needs were met. DrE and I parted ways more than cordially. DrE told me: if you ever change your mind — if you ever want to come back, we believe in 2nd chances. You are welcome back here.

Burn your bridges wisely.

XCo had elements of a mission that I actually think is worthwhile — but everything else about the company is rotting from the outside inside outside in. That bridge, I happily detonated. I quit on the spot.

I called Edan. He hired me on the spot. DrE embodies the part of humanity that I want to serve, protect and embetter. They treated me well; I treated them well. Mutual respect and decency can make the difference between worlds. I am enormously grateful to have had the opportunity to cross this bridge again.

As I reflect on the choices I have made in my life and how I have responded to the challenges and opportunities that have risen before me, ultimately, I can find no escape from Optimism.

As I reflect on the state of our world, while the Darkness surrounding our species feels greater now than ever before, I must believe that winter will pass. There is a Spring waiting. There has to be.