Don’t ‘Fake It ‘Til You Make It’
Instead, remember what you know
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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.
What to do when you get stuck
Even after all that journaling, you will not know for certain or with very high precision how a given investor will respond. But you don’t need that level of certainty simply to reach out or make a pitch. You just need to know that the potential upside outweighs any plausible risk or cost, which is often more minimal than your unexamined anxieties would have you believe.
If you still find yourself stuck in making this assessment, then it might be worth checking in with yourself, ideally in writing, to reduce the risk of getting caught up in unconstructive thought loops. You can ask yourself whether there are still fears or other hang-ups you have not fully articulated and examined. Perhaps you're holding yourself to an unreasonably high standard of certainty simply to avoid the emotional risk of putting yourself out there. (In that case, the knowledge you need to remember may simply be that nothing worth doing is risk-free.)
The upshot here is that “remembering what you know” assumes you’ve done the prior work of figuring out what you know (and don’t know) in the first place. In addition to the journaling exercise described above, there are plenty of other therapeutic tools to help you with this work:
- The cognitive restructuring tools of cognitive behavior therapy (CBT)
- The working through of psychodynamic therapies
- The values clarification of third-wave therapeutic approaches
- I’ve also described this process in steps 4 and 5 of my earlier Every article: “In Defense of Radical Self-Betterment.
But even once you reach that point of knowing what’s true or best for you, your emotions do not automatically “catch up” to that knowledge.
For instance, most founders I work with already know, at least on some level, that their impostor syndrome is irrational. They’ve heard the same stories I’ve heard about scrappy founders who won over their investors with ruthless honesty rather than posturing, and they know as well as I do how few ambitious innovators really “knew what they were doing” or “had all the answers” at the start.
Yet this knowledge is not what’s operative as they head into the investor meeting. At that time, all they can think about are the other big-name investors who’ve passed them up already, or how they’re going to talk their way out of acknowledging that they haven’t yet found product-market fit.
So how do you make your knowledge accessible and real to yourself when you actually need it most? You show it yourself in action, over and over again, until it really sinks in.
Acting on what you know
If you want your emotions to catch up to your conscious conviction that you have what it takes, then you'd better take your fears and doubts by the hand and let them see what actually happens when you pitch some big-name investors.
This is another core process common to every major therapeutic approach—from the exposure and behavioral activation strategies of CBT, to the corrective emotional experiences of psychoanalysis, to the committed action and opposite action techniques of various third-wave approaches.
But if you try to white-knuckle your way through the anxiety-provoking pitch meeting (or the difficult breakup conversation, or the scary job interview, or even the morning run) all the while mentally cursing whatever “made you do it,” you will only reinforce the conflicting emotions that made it hard for you to do it in the first place. Your fearful inner voice will say to you, “See? That was just as awful as I said it would be!” You will have no answer to give it, since you will have been mentally caught up in that narrative all along.
And by the same token, if you try to BS yourself out of feeling scared or hopeless or guilty (“fake it or make it” style), this will only erode your self-trust over time, while souring you on the possibility that your BS narrative might actually happen to be right.
Instead, if you want to give yourself a chance at genuine emotional transformation, you need to remember, in the most vivid and tangible form possible, whatever truth you want to impress upon your emotional self through this experience. So, for instance, as you head into that pitch meeting with the big-name investor, you need to remember that you are up to this challenge, and that you have an idea worth pitching.
And when I say “remember,” I don’t mean merely that you're able to recite these phrases a la empty “positive affirmations” of the Stuart Smalley variety. I mean you have ready access to some of the key evidence and experiences that make these truths viscerally real to you, such that they can stir and direct your actions in spite of your own lingering emotional resistance.
How do you reliably give yourself this kind of access, especially in emotionally heated situations where you don’t have much time to think about it? This will vary greatly depending on the context, of course, but here are some general pointers:
Sum up what you know into first principles
Write down the truth you’re trying to make real and accessible to yourself (like “There is only upside in pitching investor Y”). Then ask yourself: “What is the deeper or more general truth that makes this true?” Keep asking this of each “truth” you write down until you get to one so fundamental that you can’t go any deeper—and focus on remembering that.
Usually such principles will identify a core underlying cause or purpose that explains or motivates a wide range of the particulars of any given situation. For instance, in the case of remembering that you’re not an impostor and you really do have good reasons to be pitching this investor, the relevant first principle probably has to do with the fundamental reason both of you are there. You’re probably not there to establish how smart and capable you are, and they’re probably not there to make a quick and easy killing. Rather, you’re both there to bet on a vision of the future worth betting on.
By formulating it in these terms, you can cut through a lot of the distracting specifics in your head and focus on the essential question: Do I have a vision of the future that investor Y could plausibly find worth betting on? If the honest answer is “yes,” then you have a reason to pitch this investor—notwithstanding your lack of this or that experience, or your lack of clarity on this or that aspect of your go-to-market strategy.
Connect first principles to tangible life experiences
First principles are broad, deep abstractions over a vast range of concrete particulars. As such, they are only as powerful as your ability to connect them back to concrete particulars. To make the relevant principle vividly real to yourself in the moments when you tend to need it most, think back to a particular experience that compellingly illustrated it, so you can mentally replay the crucial beats in the narrative—and their emotional impact on you—when you need it.
For instance, perhaps you can recall a time when you’ve boldly approached and struck up a values-based connection with someone who seemed utterly “out of your league” (especially if it’s someone who then went on to become a partner or other major stakeholder).
Mentally travel back in time to that moment where you were filled with anxiety and you didn’t yet know how the situation would turn out, but you took the plunge anyway. Try to recreate how you were feeling, down to the knots in your stomach or the flush in your cheeks.
You can also set the physical scene for yourself. Wear the suit or the perfume you wore on that one previous occasion when you were really able to embody the perspective you’re trying to make real. Or try putting a sticky at the top of your monitor with a one-line quote that encapsulates the relevant moment or perspective for you.
- What powered you through those toughest moments?
- What were the best and worst case scenarios you were anticipating at the time, and how did the situation actually turn out?
- Why did it turn out that way, and what does this reveal about the variables that actually matter (and the ones that don’t)?
- What wisdom can you draw from that experience, and how might you bring it to bear on your current decision (e.g., about whether and how to approach investor Y)?
For some real-life examples of how this internal dialogue has played out for some of the founders I’ve personally coached, you can listen to my Founder’s Mindset podcast conversations with Fabien Koutchekian (cofounder/CEO of Genomines) and with Victor Borsche and Aswin Ramachandran (cofounders of Theo). Both episodes offered glimpses into the inner work required for early-stage founders to pitch their audaciously ambitious product visions to initially skeptical investors. They also share some of the internal and external rewards that eventually follow.
Use narrative aids from history and art
While your own life experiences will ultimately hold the greatest sway with your emotional self, you’ll need to have already taken a critical mass of emotional risks in order to accumulate those life experiences in the first place. But fortunately you’re not the first or last human to have faced whatever fundamental challenges you’re facing. A well-told story of someone else’s analogous struggle—be it real or fictional—can serve as a uniquely powerful reminder of what you know in principle.
For instance, if you’re trying to remember that what matters in pitching investors is your own judgment that you have a vision worth betting on, consider watching the movie Moneyball. There’s one particular scene where Billy Beane, general manager of the Oakland Athletics baseball team, stakes his job and reputation on a highly unconventional method of recruiting and trading players.
When his assistant general manager asks whether they may be risking too much, Billy says, “I don't think we're asking the right question. I think the question we're supposed to be asking now is: Do you believe in what we're doing or not?” The answer for both of them is clearly yes, and so they proceed.
Or, if you prefer to take inspiration from a fellow founder, I suggest reading the story of Sara Blakely, door-to-door fax machine saleswoman turned billionaire Spanx founder, who famously took a Neiman Marcus representative into the women’s bathroom to demonstrate the value of her new product on (quite literally) her own backside.
Reaping the emotional fruits of integrity
Acting on your fully considered judgment, even in the presence of conflicting emotions, is not “faking.” On the contrary, it is staying real with yourself. It is bringing your full knowledge—including but not limited to what you’re feeling—to bear on what you choose to do. It is acting with integrity.
This approach makes your decision-making process fully transparent to you, and it gives your emotions their best chance to evolve rather than stagnate in the face of new knowledge and experience. Rather than suppressing your emotional signals or uncritically succumbing to them, “remembering what you know” is about staying fully conscious and principled with respect to them. Only then do your emotions get transformed in line with your principles over time.
The reward of “remembering what you know,” then, is not only the wiser decisions it buys you—but also the sublime, unconflicted joy and deep certitude that eventually accrue to those who live their lives with integrity.