Don’t ‘Fake It ‘Til You Make It’

In coaching early-stage startup founders, I hear a lot of speculation about what investors care about: They’re more likely to invest in someone who “sounds like they know what they’re doing,” who “can answer their questions with confidence,” etc. These speculations are usually accompanied by a great deal of impostor syndrome—i.e., the nagging fear that one’s facade of certainty and confidence will be stripped away to reveal the floundering rookie founder underneath. 

We’ve all been in some version of this situation: We’re faced with a great opportunity, be it our dream job or a prestigious graduate school program or a meeting with a big-name investor, and we have trouble believing we’re really qualified. 

What’s the best approach to take in such situations? Is it, as is so often advised, to “fake it 'til we make it,” puffing ourselves up like a blowfish and affecting an air of confidence that we inwardly lack? Is it, on the other hand, to wear our self-doubts on our sleeve, perhaps even passing on the interview or the investor meeting entirely because we don’t want to waste their time? 

The real answer is neither of these, as they are two sides of a false dichotomy proceeding from the same unchecked assumption: that our felt doubts are grounded in reality. We feel like impostors who aren’t qualified for this job or that investor pitch opportunity, so we take that emotional narrative at face value, and then we either work to conceal it (via “faking”) or we openly endorse it. 

What if, instead, we take our anxiety as a cue to form (or re-form) a fuller and more honest view of the situation, and let that be what guides our response? I refer to this approach as “remembering what you know.” It is a framework that helps me understand and more effectively implement the wide range of science-based techniques both for regulating our conflicted emotions in the moment, and reprogramming them over time. 

In the rest of this piece, I will explain the framework in detail, then give you research and experience-based guidance for employing it, both in emotionally charged moments and as a general practice. Those of you familiar with therapy modalities like CBT and DBT may recognize many of these tactics, which I’m deliberately reconceptualizing here through the lens of “remembering what you know.”

Defining the concept: “Remember what you know”

To bring the concept of “remembering what you know” to life, let’s return to the original example of pitching an investor. (The same thought process will apply to other high-stakes situations, like job interviews.) Instead of burying your fears or acting on them unquestioningly, what if instead you take stock of the distinct combination of skills, perspectives, or character traits you might bring to the table? 

For instance, what if you remember why the investor was intrigued enough to want to talk to you in the first place? Or what if you consider what gives you the sincere conviction that your startup idea is solving a real problem in the world and you'll find product-market fit eventually? Or what if you ask yourself what you might stand to learn from or teach this investor that might make the interaction maximally valuable to you both, whether or not you end up getting the funds? 

Then you can center your communication with the investor on that knowledge, rather than whatever it is you think they want to hear.

“Remembering what you know” is radically different from the “fake it till you make it” adage, since it involves precisely the opposite of faking. It is about zooming out to examine the wider landscape of knowledge that can and ought to be brought to bear on your situation, rather than getting faked out by unwarranted (or partially warranted, or misdirected) anxiety. By contrast, “fake it till you make it” implies turning a blind eye on the anxiety and whatever legitimate dangers it might be signaling—which, by the way, is an open invitation to impostor syndrome. 

Beyond the particular case of impostor syndrome, I have found “remembering what you know” to be a useful heuristic for any circumstance in which you feel emotionally conflicted about some course of action despite some part of you “knowing better.” It is applicable, for instance, when you feel too depressed to go for a run or out with friends, despite some part of you knowing these are precisely the sorts of activities that would lift your mood; or when you are in the throes of an unhealthy addiction (be it to a substance, a video game, or an abusive partner) and you constantly crave the next “hit,” despite some part of you knowing it will only hurt you in the long run. 

“Remembering what you know” is easier said than done, of course. Below are some key principles and strategies I’ve accumulated both for doing this in the moment, and for making it progressively faster and easier on yourself in the long-run. 

Figuring out what you know

The first question to ask yourself when you feel emotionally conflicted is: “What do I actually know, and with what degree of clarity and certainty?” Merely having an authoritative-sounding assertion in your head—like “I am (or am not) good enough to pitch this investor”—does not mean you know it (as I’ve written about elsewhere). 

Journaling can be a great way to check and organize your thinking at this stage. First you might write down what you're feeling and the judgments or assumptions that underlie those feelings. (E.g., Perhaps you notice some anxiety and guilt stemming from the judgment “I’m not good enough to pitch this investor,” as in the above example.) Now you're positioned to subject these judgments to full rational scrutiny, if you haven’t already. For a judgment like “I’m not good enough to X,” your first question might be: “‘Good enough’ by what standard and relative to what valued aims?” 

In my experience working with founders, there is a big disconnect between the standards on which founders imagine themselves being judged by investors, and the criteria that actually matter to investors. It’s a classic breeding ground for impostor syndrome. Few VCs expect early-stage founders to “have it all figured out” or “answer all their questions with confidence.” On the contrary, they want to invest in founders who are honest and self-aware enough to recognize their own vulnerabilities. And those who don’t are likely not the kinds of stakeholders you want owning a share of your company anyway.

To make sure you're thinking about this in a constructive way, you might ask yourself: what standards or criteria are actually relevant to the decision at hand? If the decision is whether—and how—to pitch your startup idea to a given investor, then the relevant standard is: Do you both stand to gain more than you lose from such an interaction? The answer may then depend on a mix of contextual factors that you can pull together in another round of journaling. 

For instance, you might ask yourself:

• What business models or technologies tend to excite this particular investor, and how does your business idea match up?
• Does this investor seem interested in supporting and mentoring relatively “green,” pre-seed founders like yourself, or do they only invest at later stages?
• What sort of network do they have access to?
• What sorts of fruitful collaboration might you bring to that network given your own distinct background and interests?
• Do they tend to give “second chances”? In those cases, you may have nothing to lose by reaching out.
• Or do you only get one shot at pitching them?

With these considerations in view, you might conclude your journaling session with the considered judgment that you need to do more customer development or make more progress toward an MVP before taking your one shot with investor X, whereas there may be only upside in approaching investor Y.