On the Welcome End of a Black Year

At the beginning of 2011, all I wanted was a year of single-minded focus on our work at Simple. 2010 was a frenetic year for me, full of change and excitement, risk and commitment. I had made a number of life-altering choices in 2010 that I was eager to see through in 2011, and work was foremost amongst them.

Around this time last year, I remarked to my wife one day that things were going almost too well. We were loving our new home in Portland. I was loving the excitement of getting Simple off the ground alongside the brilliant people I get to work with every day. The other shoe had yet to drop.

Then, just as I was about to leave the office one night in March, I got a call from my mother.

“[Your step-father] is dying”, she sobbed.

And there went 2011.

Memorium

My step-father, Rodney, was a remarkable human being. Born in South Africa, he got his start in the forestry service, engaging in early conservation efforts and planting forests in Mexico as well as his home country. Diplomatic work later took him to New Zealand. Eventually, disgusted by apartheid back in South Africa, he moved his young family to the United States and found work in the decidedly niche field of nuclear transportation. There, he excelled, ultimately co-founding Transport Logistics International, which he ran until its effective sale in early 2010.

Think about this for a moment: like it or not, the world has many nuclear weapons, plus a number of nuclear reactors used for power, medicine, scientific experimentation, and so forth. In the last several decades, most of the world has decided that nuclear weapons are bad, but that nuclear reactors can be quite good and useful when operated correctly. To that end, there are international cooperative efforts, like Megatons to Megawatts, that turn nuclear weapons into fuel for power plants. So, who moves the actual nuclear material from those weapon sites to places where it can be used for good? Who moves nuclear material to and from reactors? Who keeps it safe in the process?

Well, Rod did. Which, whatever your opinions on the safety and efficacy of nuclear power, you have to agree is a phenomenal thing: moving potentially planet-destroying nuclear material around the globe safely and predictably while billions of people simply go about their days.

In many ways, Rod was my model for entrepreneurship. Throughout my teenage years, I watched him start a company, grow that company, cope with its with ups and downs, handle politics both interpersonal and international, and ultimately exit TLI successfully after more than a decade of hard work. His surprisingly small team performed their critical task from a modest office in suburban Maryland. He demonstrated every day that it’s possible to run a company ethically, do good and important and meaningful things, treat employees fairly, and still make a profit. Before knowing Rod, I never would have considered the world of business. Having known him, it’s hard to imagine doing anything else with my life.

Fighting and Dying

With most of my extended family living across the country, death was always a remote event, something that happened “over there”. Our relatively small family hasn’t been free from loss, but we’ve also had fewer funerals in our past than many other clans I’ve known. Upon receiving my mother’s call, then, my immediate reaction was to outright dismiss the distant – in all senses, distant – possibility that what she was saying was true.

My step-father had been diagnosed by his general practitioner with pancreatic cancer, a type of cancer that’s recently seen a lot of press in relation to Steve Jobs’s death. There are several main varieties of pancreatic cancer; some are operable and some are not, but the overall survival rate on a not-particularly-long time scale is not high. If you have your choice of cancers (and you don’t), this is not the one to choose.

Rod had been told by his doctor, bluntly and unkindly but ultimately truthfully, that he wouldn’t live to see Christmas (2011). We, of course, refused to accept that. We searched every available resource, contacted everyone we could who might have some insight or direction, considered every experimental option. Rod was quickly enrolled at the Sidney Kimmel Comprehensive Cancer Center at Johns Hopkins, which we deemed to be both the best and the most practical option for his treatment, as my mother and step-father then lived less than an hour’s drive away.

That was early Spring. Over the next several months of in-person visits and frequent phone calls, things went up and down repeatedly. One week, Rod would be feeling better and numbers on tests would be interpreted as saying good things; you wouldn’t guess from looking at him that he was dying from cancer. The next week, he’d be a wreck, and the numbers were now telling grim stories. Then it would all shift around again. Surgery wasn’t an option in his particular case, so our hopes of spending more time with him rested on drugs and chemotherapy.

It’s hard to say how much time the treatment bought us, and if it was worth the pain and time and expense. As summer drew to a close, I got on a plane yet again. I knew from the grim tone of the doctor I had spoken to that I wouldn’t be coming home until my step-father was dead.

The man I saw when I arrived at the hospital was a faint shadow of the man I had known throughout my adolescence and early adulthood; a pale gray crescent of a person who had always shone brightly with determination and conviction. We talked for as long as he could manage, and after he fell asleep, I wept at his bedside until I could physically produce no more tears.

That seemingly endless week in August was the conclusion of our family’s personal tragedy. Rod had sold his company a little more than a year before his diagnosis. So here, dying in barely-contained agony, was a man who had worked tirelessly his entire life, only to be felled mere months after his retirement. His regret was palpable, never at having worked hard, but for having worked too hard, sometimes putting the wrong things first. It was a final lesson.

After

Reading an article on how doctors choose to die some months later, I found myself nodding sadly along. For as far as we’ve come with medical treatment, diseases like pancreatic cancer still have the best of us. For the future, we need to aggressively fund and remove barriers to research. For today, we need to acknowledge that simply managing pain for as long as you’ve got may well be the best option. I wish Rod had spent less of his final weeks in a hospital being filled with hopeful poisons and more with us, doing whatever he damn well pleased.

I was happy to see 2011 go. The remainder of the year was filled with unpleasant reminders of death as Steve Jobs, John McCarthy, Dennis Ritchie, and Christopher Hitchens – all men I revered – passed away one after the other.

With the support of my wife, my friends, and my unbelievably kind and understanding coworkers and board at Simple, I feel ready to make 2012 the focused year that I hoped this past one would be. Life, after all, is for the living. Rod taught me how to live better and work better. That’s what we’re here to do.

—Jan 09, 2012

Obligation

Back in March, I wrote (and subsequently removed most of) a ham-fisted post about the obligation that smart, privileged people should feel to work on things that might make a difference to other people. This was discussed in the context of questioning whether so-called lifestyle businesses are a good idea for entrepreneurs and society at large.

I’ve mulled over the idea of obligation and how it relates to entrepreneurship off and on in the intervening months. That thinking has changed my tune pretty significantly.

There are several obvious problems with obligation as it relates to work:

1. Some people don’t feel obligated to do much of anything.
2. Most people don’t like to feel obligated to do something, even if it’s the optimal thing for them to do. We like choice, or at least the illusion of choice.
3. If what you’re doing isn’t making you happy, you probably won’t do a good job at it. You might even subconsciously sabotage yourself.

That final point, on happiness, is by far the most important of the three. Even if we had a magical machine that told us the optimal, most societally beneficial job for every individual – that is, the job we should be obligated to do – it wouldn’t matter if we were all assigned jobs that we hated. Fulfilling a sense of obligation isn’t a substitute for actual unqualified happiness, and it’s certainly not a recipe for good work.

At the end of the day, the best thing you can do is to figure out what makes you happy and then do the hell out of that thing. You’ll probably do a great job at whatever it is you’ve decided to do. Hopefully, your passion for your work will result in positive outcomes that benefit you and your community. Maybe we’ll all luck out and the job that makes you happy ends up benefitting a large number of people. If not: hey, at least you’re not miserable.

Problem is, it’s really really hard to figure out what makes you happy. It’s way easier to guilt yourself into a sense of obligation which you then use to rationalize the decision to do something you don’t actually enjoy. (Other popular happiness-avoidance tactics include doing nothing, trying to make a lot of money, bad relationships, and over-education.)

The type or scale of work you do doesn’t really matter as long as you’re happy. Some people are made happy by running a lifestyle business. Some people are made happy by running a Fortune 100 multinational. Doesn’t matter. Do what you love. If you don’t, you’re not going to make things better for anyone, very least yourself.

This advice is so completely and utterly not new, but it’s repeated over and over again because so few of us actually seem to remember it. Or maybe people do remember it, but they never create or are afforded the opportunity to do what they love. I’m not sure. All I know is that trying to do what you love as a guiding principle makes a helluva lot more sense then acting out of a sense of obligation. That, and I was pretty damn wrong.

—Jun 27, 2011

One Year In Portland

I realized the other day that I moved to Portland, Oregon just over a year ago.

Part of me feels obligated to write a big long post talking about the city, my favorite and least favorite things about it, its suitability for startups, the absurdity of thinking that any place can or should be the “next Silicon Valley”, if it’s really like that Portlandia show, how to deal with the rain, and so on.

I just don’t have that post in me right now. Quite honestly, I haven’t felt like writing or tweeting or really sharing much at all, lately. I just want to focus, to do good work, to recognize others’ good work, and maybe, eventually, should my endeavors deserve it, be recognized in kind for what I’ve produced, not for what I’ve said.

When I look back on so much of what I’ve written over the years, I see … well, I see the person I’ve been: young, pissed-off, inexperienced. There are things I’ve written that I still very much enjoy and am proud of, but then there are things that make me wince. That’s the way it goes, though, particularly if you’re an experiential learner fumbling your way through life. Every day is a good day to fuck up and learn something. It has to be.

About Portland, though, I will say this, if only because it was a perfect moment given to me by chance, and such moments deserve to be shared.

Two Saturdays Ago in the Japanese Garden

Portland is not much of a tourist town, unless you’re a food tourist. There’s Powell’s, the mammoth bookstore that occupies a solid city block. There’s a zoo, a couple nice museums, farmer’s markets, some pretty hikes. And then, inexplicably, there is an almost obscenely beautiful and peaceful Japanese garden perched high up in the west hills.

Two Saturdays ago, I took my visiting father and his wife to the Japanese garden. She opted to wander the paths at her own pace, and so my father and I went our own way. We strolled down by the waterfall, up by the stone sea of the Zen karesansui, by ponds and by shrubs. Finally, we stopped at the edge of the garden at a spot with an expansive view of the city.

My father is friendly and kind, understated despite formidable intelligence. He’s the sort of person that constantly gets asked for directions. Strangers look at him and think, “here’s a guy who knows what’s up and won’t give me any trouble”. When I was younger, I didn’t understand some of the decisions my father made. With every passing year, that confusion fades.

We stood there, in the garden, looking out over downtown. The sky was typical Portland gray, hinting at the possibility of rain, but the buildings were clear in the distance. My father spoke.

“It’s not exactly the most architecturally interesting city, is it?”

He thought for a moment, his eyes turning towards the trees, the mountains.

“But then, as pretty as it is here, you’d never really notice the buildings, would you?”

In that simple statement, my first year in Portland.

—May 26, 2011

All We Will Ever Have

At the end of last week, I tried to convey my perspective on a particular and narrow category of entrepreneurship that I do not believe is optimal. I stand by what I had to say, but the way in which I said it at the time was not effective. Such is the nature of debating challenging ideas: the burden is on the challenger.

At the very least, the exchange was food for thought. It helped me realize what’s worth arguing about through words and what’s worth arguing about through action.

Just as I was wrapping up a day of minor sound and fury over my post and comment, I found out that someone very close to me was diagnosed with pancreatic cancer. This person may not live to see the end of the year.

In light of that news, I’ll leave the “words” portion of this discussion with a quote from the poet Philip Appleman:

“Whatever we are, whatever we make of ourselves, is all we will ever have – and that, in its profound simplicity, is the meaning of life.”

—Mar 23, 2011

Not A Waste

Last night, after several long days, I was clicking through news and found a recent blog post by self-styled “solopreneur” Justin Vincent. Its title, Entreporn, The Fallacy That Wastes Your Life, sort of says it all, but it’s worth a read to understand the perspective of a vocal minority in the tech industry.

Frustrated by what I read, and by the post that inspired it from longtime acquaintance Amy Hoy, I left a ragey, unnecessarily personal, and vitriolic comment. I’d like to clarify that comment and my broader position on the discussion.

Regarding Freckle

I said two things that, were I still able to edit my comment, I would now remove:

1. The phrase “duping credulous customers”. This is a stupid, loaded phrase. No reasonable person is being duped by Amy Hoy’s Freckle time tracking product. Her customers have ample information with which to make a decision to subscribe to the service.
2. The word “overpaying”. This is too subjective. For a certain type of freelancer, Freckle may be well worth the monthly outlay. Value is relative.

To be clear: I did mean to call out Freckle and its creator, in no small part because she dishes it out when it comes to business and startups. I intentionally didn’t mention her by name because I wanted to imply that online time-tracking tools aimed at freelancers are not exactly in short supply. My jerky comments could have been describing Freckle, but they also could have described a dozen other web applications.

At any rate, I should have omitted the above two items and engaged in more civil discourse.

Wasn’t There More Here Before?

Earlier today, there was the more of a blog post here. The original content is still available if you look for it, but I’d prefer if you didn’t.

I tried to argue a very difficult-to-communicate point, and I largely failed. What I wrote baffled and infuriated friends and strangers alike. Some people got the gist of what I was trying to say, but most didn’t. It’s an idea that is probably better expressed through action than through words.

I have been in the habit of writing here to explore ideas that I’m struggling with. Perhaps it’s time to break that habit and find another avenue for those ideas. I’ve come to that conclusion before, and the fact that I’m coming to it again is telling.

Apologies to Amy, and to you, reader, for wasting your time.

—Mar 18, 2011