Career Advice: Penelope Trunk is a Charlatan
(Or: Physician, heal thyself)
Let’s start with this: I’m an idiot. I’m 24 years old and I don’t know anywhere near as much as I need to. I convince myself otherwise because without the strength of thinking I know at least something, I could never get much done.
That said, I do know this: there are only a few people who you should take advice from. I mean life advice: advice on how to be who you are, how to manage your world, how to grow as a person.
- People who have demonstrated an interest in your success and years of loyalty. You’ll be lucky if you get one of these. I hit the lottery, and I have two. You’ll know them with this test: If they asked you to drop everything and save their ass (business, product, family, life) for a month, you’d do it without hesitation.
- Your significant other. This is someone who spends a lot of time with you and sees all that you struggle with, all that makes you happy. You’ve been through good and bad and get wistful recalling both. My luck continues: my girlfriend is the wisest counselor I could ever ask for.
- Yourself: If you cut the crap and take a long walk alone, you can ask yourself anything and usually get the right answer. Make the time to know your own thoughts: you might be surprised how much is waiting in your own brain.
That’s all. Here are people who should not be trusted for advice:
- Some dick with a blog (even me). If you’ve ever read a top-ten post on a blog, you know the content is cranked out to drive pageviews. The author probably slapped the content together in the space of two hours to benefit an audience of thousands. Like with drive-by legal or medical advice, you’re a fool to assume you can get something directly applicable to your case from a one-size-fits-all post.
- Parents. Your mileage may vary but parents are often too invested in your safety and security to be able to weigh the benefits of those risky life decisions with huge payoffs and incredible experiences. If your parents are batshit insane (thankfully not my case, but I have seen this) that investment may yield terrifyingly bad advice. Even if the advice you get is reasonable, there’s plenty we don’t need to tell our own parents.
- Your social circle. Excluding a choice best friend or two, your social circle can’t tell you anything useful about how to run your life. Groups breed conformity and breaking from that might be consciously or even subconsciously discouraged.
- Penelope Trunk. (cf. #1)
Penelope Trunk wants to tell you how to run your career. She presumes to be an expert on this subject. She’s not.
Once upon a time, as a young man desperate for growth and success, a blog specifically like hers, geared toward shameless career ambition, seemed like crack. Loyal readership taught me otherwise. Penelope Trunk is someone barely in control of her own life. That she is honest and open about her flaws is endearing but doesn’t change the fact that she cannot provide viable career advice based on personal experience. She’s proudly a trainwreck and while that may be great for her blog’s readership, would you trust a fitness trainer who doesn’t exercise and can’t stick to a healthy diet? Mental health counseling from a patient in a psychiatric ward? Computer advice from someone who uses Windows 98? Come on. I may be an idiot but at least my bullshit detector works.
Only when Penelope Trunk is viewed as a cautionary tale will you find viable lessons for your own career. I would never claim to be qualified to advise you on how to run your life. Nonetheless, if you take the things Trunk has done with her life and imagine the opposite, you may find valuable guidance.
Read on for these lessons.
No boss, No paycheck, No worries
I’ve been collecting a paycheck since I was 15. It began at Publix, the best damned supermarket you’ll ever visit. I was a shy kid, reluctant to be employed and encouraged by a dramatically unstable home life to stay as hidden from the world as possible. But I went. I interviewed. I didn’t know much about interviewing at that point. The myriad job hunting bullet points had yet to be delivered to my brain. I don’t remember what I said or even what I was asked. It wasn’t an impressive performance, surely.
But they called me. I had a job.
And I loved it. I’d never had more fun in my life. Thanks to a handful of adult mentors, I went from being shy and insecure in front of strangers to being outgoing, helpful and outrageously courteous, as befitted Publix’s customer service mission. I got to meet people, learn about their lives and help make their day better, all in the time it took to bag up an order and pack in a car. Publix has a firm “no tipping!” policy and this was spelled out on a button affixed to my apron at all times. Despite this, not a week went by where a kindly retiree or harried but grateful parent didn’t stuff a couple bucks into my hand or pocket, buying me a sandwich or drink to end my shift. With a home life that was terrifyingly unpredictable and school that was tedious and unsatisfying, Publix, the people and the tangible benefits of my work there, became an escape that I craved.
There was plenty of reward in the fun of the job, but I found that throwing myself into my work with such gusto had other perks. When all of the front service clerks got reviews, there was much kvetching in the break room. Nickels and dimes, my teenaged colleagues moaned. They barely gave them anything for a raise. When my turn came, my boss, Mr. Starkey, called me into his office. After rattling through his estimate of my performance, I was given a fifty cent raise. It was the largest, Starkey confided, that anyone in my group had gotten. In retrospect, too, I realize that I was rarely tapped to do cleaning chores, since my management seemed to prefer me in front of customers as much as possible.
It was all so perfectly Randian, in a way that satisfied my then-Randroid brain. I gave honest effort in exchange for honest reward and recognition. Love your work, I thought as I pushed a pile of carts back into the store, and nothing feels like work.
Of course, it wouldn’t last. Home, as was its wont, took another lolloping, staggering jolt. For the second time in less than a year, we were moving away. Mr. Starkey was crestfallen. He’d been eager to groom me into cashiering and beyond. These were remarks that were and remain deeply flattering – it didn’t seem like he especially enjoyed terribly many of the other kids who had my title. At my request, he eagerly typed up a letter of recommendation. My favorite line, then and now:
“I would rehire him immediately if he were to return to Sarasota.”
I enjoyed it both for the heartfelt endorsement and for the tiny, whimsical implication that I was somehow in control of my existence.
I went on to be a salesman, an intern, a marketing manager and a project manager. With each job, I hoped to find the feeling I knew at Publix. The feeling of throwing myself into my work, enjoying every minute, and always hungry for more.
To be sure, I had some amazing jobs in the years since. Tremendous opportunities that provoked growth and change. But none of it could ever recapture the lost innocence of that first, magical time I worked at the supermarket. This realization, each time I started a new gig, was always a tiny disappointment.
For almost a decade, I’ve drawn a paycheck from someone. Until now. Not having been to the office, or any office, feels vaguely like retirement. Except there’s a ton of work to do.
And it’s back: that magic Publix feeling.
I love my new job. I’ve spent the last week building a new iPhone app from scratch. My new boss, me, really likes how it turned out. This is the most incredibly rewarding productive activity I have ever chosen for myself. The app is about done; I’ll have more to say about it soon. The most tremendous and powerful discovery came through its creation: I love developing applications for the iPhone. I can do it all day and night until my fingers hurt and still want more. It’s the most satisfying thing I’ve ever invested my working time doing. All I want is to get better and keep building.
Like Publix ten years ago, it doesn’t feel like work. It’s fun. It’s… wonderful.
Time will tell if this feeling and the products it creates will be sufficient to feed and house me. For now, I’ve got enough to hold out for awhile and give it everything I’ve got.
It’s a scary prospect to abandon security and regular cashflow, move across the country, and go into business for yourself, all the while hoping to hell everything will work out okay. Like many projects, it’s one of those things where if you truly took the time to consider all the attendant difficulty, complication and risk, you’d never bother to do it all.
It’s the best decision I’ve ever made.
Love what you do, do it for you
As I begin this post, I am nine days, six hours and 31 minutes away from leaving a very comfortable, generously-paid job where my colleagues and leadership respect me and treat me well. In just over a week’s time, my girlfriend (and adventuring partner), Aubrey, and I will be driving off into the night, embarking on an incredible roadtrip to seek out a new home somewhere beyond the Rocky Mountains.
There are no words to convey my excitement.
For as long as I’ve existed, there has always been an obligation to someone else’s rules lurking just beyond the horizon. Even on vacations, where time is theoretically mine, there was the lingering, ever-present knowledge that before I knew it, I would go back to a world of obliging someone else’s whims. For the first time, I’ll escape those bonds. It’s a feeling of freedom I’ve never known.
It must be stressed that while Full Sail has been a great place to work and I’m grateful for the experience, I had a job there and I have a handful of problems with working any “job,” no matter who supplies it. When I say job in this context, I mean any paid activity wherein you provide 40+ weekly hours in exchange for a regular paycheck, benefits and perhaps a reasonable approximation of social interaction. I’m a difficult, demanding, even impossible person, so these problems loom larger for me than perhaps they do you.
Dark Day
I have removed GlobeJot 1.0 from sale. Here’s the scoop:
Anti-Piracy is Anti-Productivity
For the last two years, one of the most fun parts of my (soon-to-end) day job has been giving the occasional tour for visiting VIPs. Sometimes my boss has his schedule packed so tight that he can’t do these tours, so I get called in as his relief. I’ll definitely miss this when I’m gone — it’s one in a small list of things I do extraordinarily well.
A couple of months back, a Washington DC-based intellectual property attorney from a prominent national firm came for a tour. Let’s call this guy Rich. I was tapped to run the tour, but when one of the owners decided to come along, I spent the bulk of the morning opening doors and walking quietly alongside the conversation. I was extra quiet when the subject turned to the recording industry. Rich explained that he wasn’t terribly popular for representing the recording industry but that it was important work. He then trotted out the same tired old tripe suggesting that a decline in recording industry revenues was caused by piracy — a decline Richard assured us could be reversed if only young people were educated on the importance of respecting intellectual property.
This is Bullshit
I listened to all of this and swallowed so hard I bruised my own throat. First of all, as has been mentioned, piracy is murderous, ruthless work done by indefensible criminals. What these guys mean is bootlegging.
I failed to ask Rich if it were possible, just even the slightest bit possible, that recording industry revenues were on the way down because the record companies make over-priced garbage. I failed to mention that education is indeed necessary… for the luddite morons who ran these businesses into the ground in the first place. I failed to point out to Rich that if each pirated track really represented a lost sale, any miraculous absence of bootlegging would have to also transform the economy dramatically as to permit people the opportunity to drop $20,000 on a half-filled iPod Classic.
I failed to say any of it. Whaddya want from me? I’m not my own man for another few weeks yet.
Even so, the encounter was instructive. I learned that there still exist real, living, breathing people who believe this bullshit. Not to be ageist, but I suspect being over 30 years old has a lot do with this, though surely there are exceptions in either direction of that mark.
The recording industry has spent millions of dollars on technical and legal measures to prevent bootlegging. The pinnacle of that achievement? A multi-million anti-piracy measure that was defeated with a Sharpie and the most impressively tarnished image of any industry that doesn’t make guns or pollution. I’m talking out of my ass, but I expect that the number of people who partake in bootlegging has only grown since this crusade began. Talk about money well spent. Can you imagine where their business model would be if, instead of wasting their money fighting an unstoppable force, they’d instead took a good hard look at the way the wind was blowing and invested that cash in reinventing their business model in such a way that made bootlegging irrelevant?
The result would be a recording industry that neither you nor I could recognize.
Instead, the RIAA makes a habit of suing the very people to whom they’d like to sell their product while attempting to destroy any service or platform that challenges the traditional ways for people to discover music.
Unstoppable Force
Anywhere there exists a non-scarce encapsulation of value, that value will be reproduced and distributed outside the bounds of the author’s license or intent. Put another way, if your shit is digital and desired, your shit will be pirated. The question with piracy isn’t whether or not it will happen. The question, rather, is whether or not your digital property is valuable enough to be worth the trouble of pirating. Trouble, here, has a very flexible definition, depending upon how much stands between wanting to distribute and being able to distribute. This varies from platform to platform, from absurdly simple with digital music to decently pain in the ass with console games.
Why? There are two simple reasons. People want things and, as we know from economics, the capacity to produce is infinitely outstripped by the capacity to desire. Secondly, and most crucially, distribution is gratifying. People feel good sharing — that’s simple human nature. In many cases, too, distribution of something digital, something protected, requires solving someone else’s puzzle. The high that comes from accomplishing something intended to be impossible is well-known nerd crack.
Piracy is Always Possible
This recipe creates a world where the dreaded boogeyman of scary piracy will always exist. Any business model where a 100% lack of piracy is integral to success is doomed to failure. What to do about this truth is a difficult question — one beyond the scope of what I can tell you here.
What’s important to understand is that time spent fighting the unstoppable is almost always time wasted.
By definition, anti-piracy measures require an investment of development time that will never benefit your paying users. Who are you working for, if not your paying users?
You have a choice. You can allocate 500 hours to one of these options:
- Building an incredible feature set that your customers love
- Developing a new anti-piracy scheme that will be defeated in X weeks and may genuinely annoy your paying customers
Which do you choose? The exhausted Microsoft vs. Apple comparison is apt here. If you’re Microsoft, you roll out Windows Genuine Advantage and truly piss off anyone who ever has to reinstall Windows. If you’re Apple, you sell a five-pack license and let your customers buy on their honor. I’m sure there’s a decent set of folks who install Leopard on more than their purchased share of machines, but the Leopard family pack is ranked #201 in Amazon’s software sales and was an even better seller when Leopard was new. And you know what? Apple makes more money through the family pack than if they were dicks by using anti-piracy measures and only selling single-user licenses.
I’ve Got One Boss
And it’s not me. The boss is the customer. By definition, my customer doesn’t give a damn about the boogeyman. They want the very best features in a piece of software that does everything it possibly can not to annoy them. As far as I’m concerned, every minute I spend on anti-piracy measures for my apps is a minute I should have spent making something incredibly useful. I’m in this to make people happy with incredibly useful stuff. If can’t focus my time on that, there’s no point.
The only time I should worry about writing code related to users who haven’t paid me money is when their existence will affect users who have. If pirates adversely impact resources essential to your paying users’ happiness, by all means, write a bit of throttling code that gives their requests a lower priority.
You’ve Got a Decision to Make
Whether or not you spend time writing code that benefits you instead of your paying customers is a personal choice. I can’t tell you what you should do — that conversation is one you need to have with your collaborators and moneymen. The temptation is a strong one. I remember how angry I was when I discovered Tallymander being distributed by iPhone bootleggers for the first time.
Still: last week, I submitted my latest app, GlobeJot, for App Store review. GlobeJot’s source contains precisely 0 lines of copy protection code.
The choice is made easier for me by Apple’s inclusion of good-enough copy protection for iPhone OS apps. Even without that, though, I wouldn’t bother putting up much of a fight. I want to make money by creating honest relationships with paying customers who appreciate that I spend every last ounce of my energies making something they will love to use.
If that ideal one day ceases to be realistic, I’ll find somewhere else to put my productive ability.