Hoagies & The Impostor Syndrome
I originally wrote the following article more than 5 years ago, but it’s been sitting in draft ever since because I felt like it needed a massive edit to be more coherent. I still feel that way to be honest… but the irony of not publishing a piece that’s all about overcoming impostor syndrome because I don’t think my writing is good enough is just too much to bear. So, here we go, editing be damned!
I say “hoagie” instead of “sub” because I grew up in the Philadelphia area. Deal with it. Also, Lee’s Hoagie House makes the greatest Italian hoagies in the country, and that’s not up for debate. Now that we’ve gotten those two critically important details out of the way, let’s talk about the life-altering revelations that can come from regular interactions with sandwiches.
Some time before my first startup, Wanderfly, at some indiscriminate sandwich shop, the only thing about which I remember is that it was absolutely not one of Lee’s Hoagie Houses, I had an epiphany about hoagies. Well, actually it was more like the first half of an epiphany which would later be completed during the Wanderfly years. And it obviously wasn’t about just hoagies, or it’d be pretty weird to be talking about it here. It was about doing stuff. Yeah, I know that’s absurdly general. That’s what makes it an epiphany.
I had ordered an Italian hoagie and tweaked it to be as close as possible to what I’d normally get at Lee’s. Lettuce, tomato and onion, sweet, hot and roasted peppers, provolone, and of course somewhere between six and eight different types of Italian cold cuts. Then top the whole thing with a drizzle of oil and enough red wine vinegar to eventually saturate the bread entirely by the time you finish it. My mom taught me that last bit and I consider it to be one of my more important lessons growing up.
As the guy behind the counter got started, I found myself watching him intently. I’m not sure if this was a more packed hoagie than he was used to making, or if it was just his method, but he started by cutting into the roll deeply enough so when he opened it and laid it down on the cutting board, both sides were entirely flat and facing upward, fully parallel to the counter. Then he started piling everything on top of what had become this single, double-width flat bread surface, with no indication of intention to fold it at all and qualify it as a proper hoagie, or any proper sandwich for that matter.
As I watched the pile get higher and higher, I thought to myself, “How the heck is he going to fold this thing?! He’s packed it with so much stuff that it’s going to immediately push out of the middle, and he’s cut the bread so deeply that if he actually does try to fully fold it, it will immediately split at the seem and have fillings busting out the other side!” But I also then found myself thinking, immediately afterwards,
Nah, don’t worry. This guy is a professional. He does this all day long for a living. He must have a method.
Well, it turned out his “method” was to barely touch the hoagie itself, and instead pull up from the sides of the wax paper underneath, and speedily fold them together as he wrapped up the sandwich. In other words, he just didn’t deal with it. He passed the problem onto someone else — namely me, the customer. Years later and after countless more experiences observing things being done by people with this same astounding and depressing level of total apathy, I also arrived at what I should probably call a counter-epiphany to this one: there’s virtually nothing you can do to mitigate or compensate for someone who doesn’t even give a shadow of a fuck. More on that another time.
So anyway, the result of this half-assed job was basically an immediate open-faced hoagie explosion as soon as I broke the tape to unwrap it for consumption, which was about 30 seconds later. I ended up sorta half folding it using the move where you press the center down with a knife while pinching the bread together, sorta just dealing with eating it open faced, and sorta just eating it piece by piece, pulling toppings out and eating them directly, vinegar flying everywhere.
It was a complete mess, but here’s the thing: it was still a meal, and it was still delicious.
I’m not saying this guy would have won any awards for his deli skills, or that what he made would have even technically qualified as a hoagie for that matter. But he still got the job done, or at least got some job done, and moved on to serve the next customer, his sandwich-making presumably motivated by having no other choice (if he wanted to keep his job), and his method apparently defined by simply not caring.
The epiphany, or again, rather the first half of the epiphany, was a simple but undeniable feeling: I could have done that myself! Here I’d been watching someone make this hoagie, presuming him to be an expert, and hoping to learn or at least observe some special technique that the experts use in order to keep a loaded hoagie together, but there was no magic here, and no set of absolute requirements where a lack of compliance results in complete failure. If I’d been standing behind the counter, I could have cut the bread and piled those same ingredients on top, and since I did give a fuck, being that it was my lunch, I would have done a much better job of it too!
Now, given that we’re not talking about particularly haute cuisine here, and instead looking at a task that is generally recognized to not require a whole lot of professional training in order to complete, this whole thing isn’t terribly surprising. Of course I can make an Italian hoagie. But that’s kinda the point. As I’d find out later — the second half of the epiphany — there are a lot of scenarios where doing stuff is like making Italian hoagies:
If you have some access to the ingredients (most of which are optional anyhow), and you pay attention, and you give a fuck, that combo can get you most of the way there.
At Wanderfly, we went through this same process over and over and over again in just about every context imaginable. There were a few differences, which is why it took me a while to spot this pattern and realize the second half of the epiphany.
First off, whether we’re talking about technical architecture or product design or fundraising or media exposure or search marketing or acquisitions, there was no metaphorical guy behind the counter saying “Can I take your order?” and offering to do it for us. Or rather, there was, but in most cases these were prohibitively expensive professional service providers, costing somewhere between a thousand and ten thousand times as much as a hoagie, so there was always a motive to first try and figure it out ourselves.
And instead of an array of ten or fifteen food bins full of nicely laid out, pre-sliced ingredients in front of us, a few “how to” type Google searches on any of the above subjects would quickly yield several million potential options and examples and opinions. And instead of the next customer patiently waiting behind us in line, there were literally hundreds of other startups who appeared to be rushing over the counter and coming away with scrumptious looking hoagies themselves. But other than these few minor differences, the startup experience turned out to be just like making hoagies.
The pattern that emerged went something like this. First, we’d be faced with the need to do something that none of us had ever done before. In most cases there wouldn’t even be an opportunity for mental posturing or denial about the situation, because these challenges were so completely and obviously foreign. None of us had ever raised money, or talked to the media, or built a server to this degree of scale, or hired employees, or struck a commercial deal with a Fortune 500 company — the list was virtually endless.
So it usually began with a general understanding that we were all in over our heads, but also all in the same boat together, so we could push right past what I like to call the “ego bullshit” (more on that another time too) and get right down to the immediate collective goal of trying to determine how not to drown. From there, the next step was invariably information gathering. Every now and then we’d have an advisor or someone in our network who was in a position to try and point us in the right direction, but since these total unknowns were coming up on a daily basis, generally the starting point was Google. This would naturally lead to a flood of information, and while Google does an amazing job of surfacing and prioritizing the most relevant information, “relevant” here was highly subjective and would frequently lead to even more unknowns, so there was a never-ending process of information gathering and consumption.
Next, having gathered some potential ideas and plans of attack from all that information, we’d do… something. The something would frequently just be a first step toward an overall goal and might not feel like much at all, but it was always clearly distinguishable from the prior information consumption step in that it was invariably some action which could have some observable effect. Never talked to media? We’d respond to the email from the random no-name blogger who just contacted us and go have a meeting with him, pretending he was from the Wall Street Journal. Never raised money? We’d take our best shot at creating what we thought a fundraising deck should look like, send it to some people — investors or not — and see what questions they came back with. Never built a server that could handle the load we were getting at peak times? We’d simulate throwing ten times that load at it, and watch what happened.
The nice thing about doing something is that no matter how seemingly insignificant, that action can have results. Or in some cases, it can have no apparent results, and that can be useful too. Sent ten cold emails out and got no response? Maybe there’s something wrong with the message, or with how the recipients were selected, or both! Either way, this was where that second component of making hoagies, as I outlined above, came into play: pay attention! We’d gather some knowledge, do something, pay attention to what happened or didn’t happen as a result, and then try to do the most obvious thing in the world:
Follow what works!
Take the aspects of the action that appeared to be responsible for achieving the desired outcome, and do more of them. Take the ones that appeared to be responsible for hindering or blocking the desired outcome, and stop doing them.
It’s as if we were running a never-ending series of tiny little science projects. Do something, see what happens, adjust accordingly. Do it a little differently the next time, see what happens, inch forward or backward, tweak again. Rinse, repeat. Trial and error, ad infinitum. Plenty of times we’d take the wrong action, or mistakenly attribute these mini successes and mini failures to the wrong facets of our actions, and need to revert in subsequent trials. But as long as we kept paying attention and simply kept going, following what works was a way to cheat our way out of the science project. After all, we weren’t looking for results of random trials to publish in some academic case study; we were looking to tip the odds in our favor in order to get somewhere.
In each of these trials, any time you do something hoping to achieve some goal, there’s a range of potential outcomes which, at the extreme ends of the spectrum, goes from an utter-crash-and-burn-stop-everything-and-reassess-your-life degree of failure to a total-instant-win-immediately-celebrate-world-domination degree of success. And while we always hope for the latter, I find there’s also a small desire to see the former too in some cases, because then you know for sure that you need to change something in the next trial. The challenging part, though, is that it’s a bell curve type of distribution, and in the vast majority of cases, the result is somewhere in between. In fact, I can’t think of a single event in the entire experience, or in my entire life for that matter, that I’d classify as either endpoint of that spectrum. The meeting with the Fortune 500 company went well, but there was one pretty senior guy in the room who didn’t seem convinced. Or the product is working well and people seem to love it, but they’re not using it nearly as often as we’d hoped.
Do something.
Pay attention to results.
Change something and try again.
Follow what works.
Being completely immersed in this experience over time has one of two effects on people, which to continue my drowning metaphor from earlier, roughly corresponds to the two potential outcomes of that scenario: sink or swim. Sometimes it’s too much, and not at all what you expected, and you get out of the pool as fast as possible (or get dragged out by a lifeguard). Other times you discover that, whether you thought you could or not, you can swim! Then while your friend is sitting there shivering and catching his breath by the side of the pool, wondering why in the world you’d continue to subject yourself to this torture, you’re gleefully staying afloat, not feeling tortured at all, and amazed at your newly discovered ability. You might be swimming in circles, or you might just be treading water and not going anywhere, and you probably haven’t even identified or labeled what you’re doing as swimming, but at least you’re not sinking, and that’s new and exciting.
If someone had asked you beforehand how you knew you could swim, the only true answer would be “I didn’t!” And in fact, even despite this experience, you might still think to yourself or tell people, “I can’t swim” for some amount of time. This condition, when perpetuated, has been dubbed “Impostor Syndrome,” which Wikipedia defines as follows:
“A psychological phenomenon in which people are unable to internalize their accomplishments. Despite external evidence of their competence, those with the syndrome remain convinced that they are frauds and do not deserve the success they have achieved.”
Indeed, the objective reality of the situation here does not match the label. You may still not think you can swim or call yourself a swimmer, but you just spent twenty minutes moving around in the deep end of the pool without dying. So whatever you want to call it, it sure as hell bears a strong resemblance to swimming.
And that’s the exact experience of being in a startup for an extended period of time. It’s why people keep at it, despite what may appear to outsiders to be terrible conditions. It’s also why little kids, when they actually are learning to swim, routinely go from being deathly afraid of the water to staying in the pool for hours on end. It’s a raw, empowering experience: I can do this! Except that in a startup, “this” rotates from one deep end to the next on a constant basis. Two days ago, we didn’t know anything about building a search engine, but today we’ve got a rough prototype returning basic query results. Two weeks ago, we had no idea how go about fundraising, but tomorrow we have two VC meetings lined up. Two months ago we’d never hired an employee before, but just yesterday our first one started.
In each case, it’s easy to feel like you’re doing it wrong. And if it’s the first or second or even tenth time, you probably are! Or, more accurately, you’re probably not doing it in the best way possible. Your search engine will probably crap out when faced with a few concurrent users, and those first few VCs will probably not be impressed or invest, and there were probably some legal holes in the employment contract you found online. So you may still feel like you have no idea how to do it.
But you’re still doing it, which makes you someone who has done it, which makes you someone who does it. In other words, you’re not an impostor.
