Don’t Fake It ‘Till You Make It. Do This Instead.


Earlier this week, as I was exploring a potential investment property, the real estate agent provided my with the range of rental incomes for the property. However, as an avid follower of Samuel Zemurray’s advice (“Never trust the report.”), I dug a bit deeper. I called two rental agencies who represented units in the building and got actual numbers for what the property earned.

As it happened, the numbers were quite good, on the high end or better than what the agent had estimated. When I saw this, I smiled, not only because of the good news, but because the agent had unintentionally followed another piece of advice related to that first piece of advice.

It comes from the great John Boyd. In his wonderful biography of the eccentric fighter pilot and military reformer, Robert Coram tells a story about a case that Boyd was attempting to make against the B-1 Bomber. After finding what he felt was definitive proof that the plane wasn’t going to work and was horribly over budget, Boyd declined to use these numbers. Instead, as Coram writes,

“Boyd did not want to take these numbers to the Air Force, not yet. He ordered Leopold to recompute everything as a “best case,” that is, to give the B-1 advocates the benefit of every doubt. Every time Leopold had a choice of numbers, he was to use the most conservative. This meant that under scrutiny, and the Air Force would indeed subject the study to the most rigorous scrutiny, the numbers would only get worse; that is, any adjustments would show only higher costs.”

The agent I was speaking with could have stretched the truth. He could have given me optimistic numbers about the rental prospects of the property. Most clients would probably not only not notice, but would in fact extend it further with their own wishful thinking. But some people will check and if they catch you exaggerating, as the Air Force was hoping to do with many of Boyd’s criticisms, they’ll have the perfect excuse to stop listening.

In this case, finding that the potential upside of the investment was greater than expected, created a number of benefits for the agent. I trust him implicitly now as I know he is not the type to make a hard sale. I am now comfortable that the investment works even with this conservative math. And most of all, one of the excuses I was looking for as a buyer—one should always look for reasons not to do something they are excited to do—has evaporated.

Again, this was more than just a tactical insight from Boyd. When he was in high school he took an IQ test that, clearly by way of some error, said he had an IQ of 90. Yet even at that age, he was smart enough to refuse to take the test again. He felt he’d just been given an enormous advantage. For the rest of the life, he would tell people about that score and cultivated a reputation as a dumb jock, a simple fighter pilot. Those who believed this first impression would eventually rue underestimating him.

Yet what is the advice that we give most people? It is exactly the opposite of this! Fake it until you make it. Act the part. Market your best qualities the loudest. What are we telling people here? We’re telling them, in short, to over-promise. We’re asking them to misrepresent the numbers—about their skills, their confidence, their understanding—and hope they don’t get caught.

That has always struck me as a horrible way to kick off one’s career…and a worse way to continue one.

As far as branding goes, many more established people fall into the same trap. They master appearances and positioning and copywriting in a way that often papers over weaknesses or flaws. They look great on their website or in their work, but meet them in real life and you’re disappointed. God forbid you end up getting a look under the hood—at their real financials for instance or just have the experience of hiring them—and you’re just disgusted. And you’ll never make that mistake again.

Early on in my life, after having a couple encounters with people whose work had painted a very different picture of who they were, I decided I would make Boyd’s strategy my overall life strategy. Call it the Boydian Lowball. On a more tactical level, I wanted to make sure that if I was, say, challenging someone’s project or idea, I would give them the benefit of the doubt first (Peter Thiel calls this the “steel man” tactic). I wouldn’t use the stick just because I had it, but reserve it for later. But on a more personal level, I wanted to make sure whatever brand I created as a writer or a public figure undersold the goods.

I want my bio to understate my accomplishments. The sales figures I use or the stats I mention in my writing are going to be conservatively proven rather than optimistically expressed. When I edit my writing, I actually try to go back through and soften certainty and intensity. Because that’s more honest, even if slightly less compelling.

Another example: I give a lot of talks to groups and sports teams and conferences because of my books. First off, it’s always interesting to me, knowing a lot of other people who do this for a living, how much insane exaggeration there is in the industry about what other people get paid. I don’t engage in any of that. But when I give talks at the end, there’s usually a long Q&A session, which I love doing. A significant portion of the time, after the event is over, one of the organizers will thank me for doing the Q&A and express appreciation that I was good at it. That struck me as off, of course I should be good at answering questions about what I just talked about. I mean, that’s my job and it’s why you hired me. The first few times this happened, I asked what they meant. Are other people not good at Q&A? It turns out, no, they aren’t. They give great polished talks but when it comes time to speaking extemporaneously they can’t perform.

To me, this is a great example of the dangers of overpromising. If you present yourself as an expert about something, you better be able to deliver on it all the way through. Many speakers can practice a talk until it looks masterful but can’t actually speak about the topic (or related topics) authoritatively. The worst part for them is that the Q&A comes at the end of the talk, so they leave the stage having followed up their initially positive impressive with a negative one.

My goal as a writer and as a person is to undersell and overdeliver. There is very little upside in the long term at attracting fans to your work by posting pictures of you on a private jet. Or talking about how much money you make—particularly if you are exaggerating that number for effect. The same goes for name dropping. Or adding extra labels to your name. Ryan is an angel investor, entrepreneur, MENSA member, whatever.

Be who you are. Let your work speak for itself. Let it speak quietly too.

You should avoid these things beyond the minimum not only because you don’t want to be a douche. Or rather, when you’re a douche, you also make yourself a target, and the more you do it, the bigger the target gets. I can think of one author I know who has upwardly inflated his sales figures for many years. Not only do I think this has deprived him of the real pleasure of enjoying what he actually accomplished, the bad habit has fed on itself and created a cycle of exaggeration and attention seeking. Sadly, I don’t think the deceit is even intentional at this point. It’s been repeated enough times for long enough that the author believes it. Dishonesty is bad for the soul and when it becomes a behavior tic—driven by ego—it begs for a hit piece by a journalist.

As I wrote in Conspiracy, the founder of Gawker, Nick Denton is a good example of this dance in both senses. On the one hand, the company benefited for a long time by making itself look bigger and more powerful than it was. This deterred most of its enemies. Gawker also deterred its enemies by exaggerating its weaknesses, as Denton explained to Playboy, “I lower everyone’s commercial expectations. ‘Oh, nothing to see here. There’s no business here. This thing has the revenue of a hamburger stand. We have no journalistic ambitions. If we ever commit journalism, it’s by accident.’”

And again, this worked for a long time. The problem was that eventually someone, in this case the billionaire Peter Thiel, actually checked. What he found was that both the extreme elements of Gawker’s branding—that it was a large, powerful media outlet that shouldn’t be messed with and conversely, that it didn’t have any assets or ambitions—were misrepresentations. Thiel did the math himself and found there was something to go after and at the same time, Gawker was perhaps a paper tiger that needn’t be feared.

And the result? A $140 million dollar, bankruptcy-inducing verdict against Gawker.

That is why you don’t want to bullshit people. Why you don’t get too far out over your skis.

Because if you get caught, you will fall. It will hurt.

Being underestimated, underselling is better anyway. Provided that it’s backed up, ultimately, by impressive goods. One of the most powerful and viral emotions is surprise. Use that.

Be more articulate than they expect. Nicer in person than they would have thought. Have more ideas than interns usually do. Make honesty a policy where few do. Be in way better financial shape than anyone would guess. Reveal that new or interesting hobby later, after they already like you. Keep that stick behind your back until you really need it—pull it out an whack them with it right while they’re in the middle of doubting you.

That’s what real winners do. And they do it while posers are both busy pretending to be those things and paranoid they’re about to be caught for it.

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