(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.

1. 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.
2. 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.
3. 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:

1. 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.
2. 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.
3. 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.
4. 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.

Bullying is Okay

Earlier this year, Trunk was complaining about her kids. I don’t blame her — parenting doesn’t seem like a lot of fun at times and blowing off steam via Twitter is cheap, easy relief. Things got complicated when our thin-skinned heroine was sassed by some jackass in flyover country. What did Trunk do? For most people who aspire to the public eye, ignoring this would be right move. Maybe using Twitter’s block feature, if you’re an especially petty kind of douche, would have been called for. In any case, it’s hardly worth more than a few seconds of thought. I guess Trunk wasn’t busy enough with her family and leading her startup because instead of doing the grownup thing, she called his place of employment and saved their number with the intent of “ruin[ing] his life there if [she] ever felt like he needed to be taught a lesson.”

(I’m not sure crazy internet lady calling out of the blue and whining about 140 characters of abuse is something technically capable of ruining anyone’s life. I leave it as an exercise for the reader to determine what her true plan really was.)

Next, she called his wife. From the blog: “There was no answer. Maybe by then he had alerted his wife that he is being pursued by a psycho who maybe will kill her kids or maybe will kill him. Maybe they will never answer their phone again.“

(My emphasis.)

This is professional? This is what we do with our careers? There’s a word for this: unhinged. Self-revelatory stuff, right there.

Finally, Trunk penned a seething, rage-soaked blog post naming names and even the guy’s home town. She was impressed with herself, though, for having the maturity to not post his home phone number. Trunk was happy enough to ruin his Google mojo forever. She is, in fact, proud of that post to this day. (Notwithstanding the flurry of posts that came next, lasting just long enough to push the hatefest off her front page.)

Anti-Lesson: When you build a blog readership and a meager Twitter following, you should use these tools to bully the hell out of those who dare disagree with you. Anyone who tells you your behavior is unacceptable just doesn’t get it. It’s worthwhile to spend a significant amount of time and effort persecuting a grudge. You can use bad behavior to impress other people by appealing to the worst within them.

The real lesson: Self-control is important. In your life, especially as you become more successful, more and more jackasses will come out of the woodwork. How you respond to the least courteous of those around you speaks volumes about your true character. You can spend a lot of time getting vengeance against those who piss you off but the payoff is rarely worth it. If you want to make yourself seem smaller than you are, the best way to do it is to give attention to someone who doesn’t deserve it.

“Online Stars” Are Important

We’ve all been in this predicament before:

“So, D, who is really attentive and normal—two traits I have never had in a boyfriend, ever—is scary to me because I’m giving up the chance to enhance my brand by dating an online star.“

Yeah, I guess maybe not so much. Trunk is still in high school — approval of the internet cool kids is so important to her that not dating one who can improve her standing is a quandary worth blogging about. She has since resolved the quandary by electing to marry a farmer. He must be the retired co-founder of Skype or something.

Speaking of quandaries and farmers, the internet cool kids caused a conflict there, too. After accepting a reconciliation date from this then-estranged farmer fellow, Trunk realized she was double booked!

When I came out of my giddy stupor from his email, I realized that [the date] was the same weekend as maybe the biggest schmoozing event of my life: Guy Kawasaki invited me to spend a weekend on the USS Nimitz with Michael Arrington, Robert Scoble and others.

I said yes to the weekend, of course. Because how can hanging out with these guys not be great for me? It’s probably what I’ve been working up to my whole career: a weekend like that.

Trunk ultimately did what anyone with healthy priorities would do: she spent the weekend with someone who loves her instead of with a self-important group of perpetual children whose only interest in Trunk is how she’s able to further their own interests.

Invitation to dine with the Obamas? With Steve Jobs? With the late Norman Borlaug? Yeah, the farmer could take a hike. But these guys on the Nimitz? No one will know who they are in 20 years. There is no conflict. These guys were a group of assclowns who have never made any meaningful contributions to humanity. They’re worth skipping for someone who cares about you. If you’ve spent your whole career working toward a weekend with them, you need a new career.

Anti-lesson: People who have convinced the internet they are cool deserve our time, reverence and attention. If you’re going to waste your time with people who aren’t internet cool kids, there had better be a good reason. You should spend your whole career getting to the point where you can possibly one day hang out with these cool kids.

The real lesson: Often with little meaningful or useful accomplishment, people can convince the internet they are cool. Maybe they truly are. Just as often, these flavors of the minute will be forgotten within a decade. Either way, they’re just people. You have your own people. You should measure the value of your people by what they contribute to your life rather than their Twitter follow count. If your career is itself focused on convincing other people you’re cooler than you are, you should switch to a career where you’re actually doing meaningful work.

You Kind of Suck and Can’t Be Incredible

Penelope Trunk wants you to know: “[Dooce] is a marvel. And you are not.”

Dooce is, in fact, a marvel: a blog that pays her bills, millions of Twitter followers and a self-directed life right from the comfort of her home. Without even meeting you, though, Trunk dispenses the above defeatist advice: you’ll never be that, even if you want to be. Dooce is not an overnight success by any stretch: she has been writing her blog for eight years. While she is certainly talented in relating her thoughts, one of the greatest contributors to her success is her simple willingness to keep showing up, year after year. Woody Allen will tell us: 90% of success is just showing up. He should know — a large swath of the population finds his self-indulgent New Yorgies unwatchable. (I am on the fence.)

Anyone with a modicum of interest in an activity and a willingness to keep showing up over and over again will become a marvel. Malcolm Gladwell calls this the 10,000 hour rule.

Imagine if Penelope Trunk had given Dooce that advice, before she became a marvel? Imagine if she had told a young Heather Armstrong she’s not much of anything and should stick to doing jobs she doesn’t much like. Imagine if Dooce had believed it. (Not that it seems she would — by all accounts, Dooce is someone who does whatever it is she wants.)

Dooce is exceptional because she chose to be, not because a supernatural event anointed her with that status.

While the overall advice of Trunk’s post is so blindingly obvious as not to need saying (blogs won’t immediately make you money), the evidence used is part of an overall theme of her blog: Penelope Trunk thinks you kind of suck and you should just quit trying to build your career if the path you’ve chosen isn’t immediately marketable. But I’m getting ahead of myself.

Anti-Lesson: Things that are hard aren’t worth doing. Other people are better than you. You shouldn’t even bother trying. You kind of suck.

The real lesson: You’re in control of how great you are (or aren’t). You decide how quickly you reach 10,000 hours of anything. You’ll become incredible only if you choose to be: by doing the near-impossibly difficult work necessary to get there. Just like everyone else who ever chose to be incredible.

Unethical Behavior is Just Fine

If a company pays you to say something about them, Trunk says, there’s no real reason to disclose that. That’s for newspapers. You should just trust that she’s making money from smart companies, and that makes it all okay.

The trust of her readership is for sale to highest, smartest bidder.

The FTC, unfortunately, doesn’t agree that this is acceptable behavior. They’ll be going after companies who pay bloggers to endorse their products without disclosure.

Is it unethical? Of course it is. There’s a big difference between caring about a product or company for its own sake and caring about it because you’ve been paid to. Penelope may dance around this by saying she only picks good companies but that doesn’t change the fact that she failed to disclose a paid relationship. Her estimation of a post’s value after the fact doesn’t excuse the lapse, either. This kind of ends-justify-the-means rationalization is the hallmark of a crook.

It doesn’t matter if the conversation is between a newspaper and its readers, a blog and its subscribers or a friend and a friend. When one party is giving advice that could be influenced by an outside force, it is essential that the influence be announced openly. Anything less is simple dishonesty.

Anti-lesson: It’s fine to build a loyal readership and then sell their attention without disclosure. The rules of ethical behavior only apply to old media. You make your own rules — honesty is less important than cash money.

The real lesson: Don’t build trust and then quietly sell it for money.

Don’t Do What You Love — Do What is Easy Based on Your Existing Resume

“One of the worst pieces of career advice that I bet each of you has not only gotten but given is to ‘do what you love.’”

Yeah, she said that. Supporting evidence: “I am a writer, but I love sex more than I love writing. And I am not getting paid for sex.”

Trunk even had a talent for combining these things, writing “the best sex scenes” her writing professor had ever read. She gave up on her erotic literature career, though, because she believed it wasn’t important enough work.

“So if you are overwhelmed with the task of ‘doing what you love’ you should recognize that you are totally normal, and maybe you should just forget it. Just do something that caters to your strengths. Do anything.”

Hmm. So because Penelope can’t do it, there must not be any way at all to find a way to build a life and career around what you love, huh? Because you can’t immediately find a way to make your work impressive to other people, it must be impossible to find greatness in it?

Bye, Adam Savage. You love scifi, building things and using your imagination. Can’t think of any way you can parlay that into an enormous, satisfying career. Be a bricklayer.

Bye, John Gruber. You love details, design, Apple, and writing. There’s no way those things can possibly come together as a lucrative blog that lets you be your own boss. Go scrub toilets.

Bye, Phil Tan. You love music? What do you think you’re going to do with that? Go buy some CDs or something.

Bye, even, to my mother. Someone who didn’t even have the benefit of a complete high school education somehow found a way to turn her love of animals into a career that let her be her own boss while keeping me fed, clothed and housed my whole childhood. Seriously: there is not a thing this woman loves more than animals, as her past ownership even of ostriches will clearly demonstrate. The result of that and years of hard work is that she’s the best pet groomer in whatever city she’s in, bar none. She can do that because she cares about her clients’ animals in ways that other groomers, just paying the bills, never could.

I guess she should have just gotten a retail job and stuck with that, right, Penelope? Hey, you said do anything.

Anti-Lesson: Don’t do what you love. It’s hard! Since Penelope Trunk never figured out how, you shouldn’t bother, either. Instead of dedicating yourself to something you’re great at doing, absolutely love doing, become the founder of an also-ran social network for young people that provides none of the value of its competitors while alienating the sort of older, more accomplished professionals those young people need to meet.

The real lesson: Your passions give you deep, generous, unique insight into specific problems. With some luck, a little imagination and a ton of hard work, you can focus your career around the things you care about. There’s a significant chance that career will matter a whole lot more to you than just “doing anything.” You’ve got a better chance at finding happiness in work you find meaningful rather than trying to fit into roles that other, faceless people will deem great.

Does Penelope have a strong writing style and a compelling blog? Absolutely. Does she have a gripping sense of honesty and transparency? Sure. But let’s be clear: as a vendor of career advice, she is a charlatan. If a career of settling for second-best, letting other people decide the value of your passions and giving up on your dreams is what you seek, then you seek Penelope. If you want your self-worth to be short-changed, then get yourself over to Trunk. If you want to improve your brand image by writing psychotic screeds against nobodies in Ohio, then boy, do I have the role model for you!

In the final equation, the case of Penelope Trunk is a sad one. By letting other people decide what matters, what’s important, she took her passions out of the driver’s seat of her career too many times. By worrying constantly about other people’s estimation of her potential greatness, she condemned herself to a life of mediocrity. Her blog and its continual churn of the latest misery, the most recent stress, is a chronicle of the results of those decisions. I don’t want that to be me.

Trunk needs to do everyone a favor, herself included, and cut the career advice crap. She is at her best when she writes about herself. The drama queen schtick all on its own is more than enough to build content around. Her sycophantic hoards of hysterically, irrationally loyal commenter fans are evidence enough of that. While her bad choices make for poisonous, self-defeating career advice and a needlessly stressful life, they nonetheless make for entertaining, instructive, even inspiring reading. That’s a great focus and the best part is that it doesn’t presume to be qualified to tell other people how to manage their lives.

I have met men and women who have done incredible things. I have found role models in people who came from nothing, who had nothing but passion on their side, and who now spend their days being paid to do incredible things they absolutely love. It’s real. It’s possible. But I, for one, will never find that place by listening to someone who says I can’t. Who comforts herself by telling you that you’re not good enough. That’s poison. That’s quitting before you start. That’s being someone else’s person, fitting into someone else’s expectations, living someone else’s shortcomings, instead of being who you yearn to be.

My advice? Don’t listen to me. Don’t listen to anyone who tells you things online. Make your own decisions based on your own values, your own passions, your own drives, your own strengths. If you must, get advice for managing your life’s direction from people who know you, who care about you, who you can trust. Most of all, get it from people whose lives and careers approach a level of sanity and stability you’d like to emulate. If you must get advice on running your career from the internet, this is the only source I’ve seen with viable information:

Merlin Mann and John Gruber at SxSW ’09. They’re talking about blogs but their advice is broadly applicable to any career where you choose to do what you want to do.

Final advice, which you also should not take just because I’m saying it: Instead of writing comments on someone else’s blog when they piss you off, write your own post. Your content is yours — don’t fuel someone else’s blog with it. That’s their job. Also, don’t wait years to write that post. You’ll be stuck writing a long-ass screed like me.