Being insecure while doing a complicated thing, especially if everyone else doing it appears very confident, is called Imposter Syndrome[1]. More than likely, the other people are faking confidence too - I certainly am in most situations!
Imposter syndrome involves a competent individual who significantly underestimates his or her competence. It has nothing to do with the complexity of an undertaking, or how confident one is relative to others.
Are there founders who exhibit imposter syndrome? I'm sure there are. But can every instance of founder insecurity be attributed to this? Absolutely not.
It might not be the politically correct thing to state, but there are lots of founders who have good reasons to be insecure. They have no domain expertise. They are trying to start a business with little to no capital. And so on and so forth.
Telling these folks that they're merely suffering from imposter syndrome does them a disservice.
Perhaps. But this founder (OP) doesn't seem to fall into that category to me, given how she writes.
Also, note that I said "while doing" - not "while trying to". Imposter syndrome does indeed require a moderate success, a total failure does not suffer from it.
The writer is over-analysing things and, with the risk of complete generalisation, is a trait more in women than men.
She needs to concentrate on the job, and more importantly, the duty, and stop thinking of non-existent worries and bad potential possibilities/outcomes. Duty is sometimes placed in a bad light, but for a founder, it's the only thing that matters. In fact, I will argue with anyone that duty is much more important than passion. Duty gets one through the shit times and grunt-work, passion does not.
She says she doesn't worry about customers and yet that is the only thing she should worry about. Not (as she writes) investors, advisors, and the craziest one of them all, other founders (jeez). She needs to worry about getting and satisfying customers. Period. They are the only things that matter.
The job of a founder is to create a self-sustaining business. And by self-sustaining, I mean the ability for a business to operate based on its own cash-flow. No investor, or advisor, or other founders are necessary for this, but customers are.
So she needs to concentrate on duty. And her duty is to attract, keep, and satisfy customers, so that they sign and continue to sign cheques. And by doing this, all those other fears will dissipate.
I'm thinking of an observation I made when I first committed to working full time on my startup... I'd heard that the only two emotions founders feel are elation and terror, but I didn't know they were at the same damned time!
Right now, I'm still in my first week of full-time startup work. I wake up worrying in the middle of the night.
I think she nailed it on "Empirically, it seems like the more you need from other people in the startup community (advice, introductions, feedback, funding), the more of a popularity contest it feels like.".
I say this because I live on an opposite environment. I am a solo founder in São Paulo, Brazil. There is a startup scene in here, but as an early one, not as helpful and omnipresent as in Silicon Valley. So when I actually founded my startup I quit it. I quit the events, the meetings, everything. These were either for wantrepreneurs or "lets-congrat-ourselves-how-successfull-founders-we-are" kind of events. I am neither.
So, sure, I have no one to go ask for advice, to talk problems through (that's why I read so much HN and this founder's blog posts). But I also do not have this pressure, this insecurity. I personally also were always very self-confident, don't know why, just knew everything would turn out good on the end. But I do feel a lit bit of this because of my angel investors. They are the ones I want to impress. So I imagine if had this urge to impress not only for the three of them, but for lots of VC investors, fellow founders, mentors, press, etc.
Another difference in the environment that makes my life easier as a founder is that no one here actually expect me to succeed. Sure, my friends and family hope I will get lucky, be a millionaire, etc. But all the time they offer me job opportunities, talk about possible carreers, companies to work. It is not that they expect me to fail, they actually think it is worth a try at being a founder. But they know that probably I will fail and I need to have a plan B, a job.
In Silicon Valley, i imagine a culture where fail ocasionally may be ok, but not quiting. You see this "fail is accepted" everywhere, but actually is ok to fail if you are still trying. You fail a company, if you found another and another, everyone will still have hopes for you to someday succeed. Even the investors of your failed one. But I don't see the same praise if you fail your company and accept a job on Google (or god forbids, a small, humble software company) and tell people you will retire there. Oh no, this failure and quitting will not be accepted. Then you will be a loser.
But here in Brazil is not like that. If I fail this company and try to found another, I will be irresponsible. But if I fail this one and get a good job, i will have succeed. I will be seen as having done a risky thing that could compromise my carreer (founding an startup), but in the end I got a good job, so everything is ok.
As I believe I could get a good job in the end, I feel less the pressure for not to fail and this "impostor syndrome" is not a thing for me.
The doubt is: is the easy going environment bad for my chances to succeed as a founder? Is this meat grinder culture that is SV actually good for its founders? At least the ones that survive it?
I like to think that no, that this is just a negative externality of the real factors that make the difference for SV founders (a lot of mentors, investors, developers, successfull founders, etc.). I like to think that I may be very successfull without the onus of overwhelming peer pressure. But who actually knows?
On the note of "Empirically, it seems like the more you need from other people in the startup community (advice, introductions, feedback, funding), the more of a popularity contest it feels like."
In the must read book called, "Winning Through Intimidation" by Robert Ringer, he postulates that...
"The result you get in a negotiation is inversely proportionate to how intimidated you are by the other person."
His solution is what we call Takeaway Selling...where you remove the opportunity to do business with you...creating an environment where they stop thinking about WHY they should work with you (or invest) and focus on how to get you to let them work with you in the first place. (Much like pinterest did so successfully with their beta invitations.)
Yeah, it's a weird place to be. I recall another local founder speaking at an even last year and telling the crowd something like "being a founder you're simultaneously ridiculously optimistic and expectant about the future, AND scared shitless and terrified".
I heard that and immediately thought "Yeah, that's me lying in bed before going to sleep every night."
Am I scared we'll fail? Absolutely. Am I completely confident we'll succeed? Absolutely. Sounds like a contradiction. Maybe it is, but what can ya do?
I also recall somebody (pg?) saying something to the effect of "the most important thing in founding a startup is managing your own emotional state". That strikes me as very, very true. It's OK to be afraid, but you still have to do what needs to be done anyway.
This is one reason I think sports (like football, wrestling, whatever) are more important than many geeks give them credit for. You learn a lot about perseverance, "intestinal fortitude", etc. from sports. And sports can serve to reinforce that mindset that says "Success isn't permanent and failure isn't fatal; it's the courage to continue that counts". Your team fumbled the ball near the goalline while down by 5 pts with 59 seconds to play in the 4th quarter? Great, guess what, the game isn't over. Keep playing, score a safety, return the free-kick-after-safety deep, and kick a lst second FG to tie the game. It can happen. And if it doesn't, well, there's always another game.
Here's something motivational for anybody who's doubting themselves... It's 2002, at the NCAA National Wrestling Finals. Rob Rohn is wrestling Josh Lambrecht, and Rohn is down by something like 10 or 11 points with around a minute to go. He's close to losing on a technical fall, and certainly has no chance to come back. The TV announcers are already starting to congratulate Lambrecht on the win.
>>"I also recall somebody (pg?) saying something to the effect of "the most important thing in founding a startup is managing your own emotional state". "
Horowitz in "the hard thing about hard things" has a chapter called "the most difficult CEO skill". Starts with:
"By far the most difficult skill I learned as CEO was the ability to manage my own psychology."
I just found this PG quote, "One of the most interesting things we've discovered from working on Y Combinator is that founders are more motivated by the fear of looking bad than by the hope of getting millions of dollars. So if you want to get millions of dollars, put yourself in a position where failure will be public and humiliating."
Thank you for posting this. I have no data, but I think it's very common for people to have insecurities about what they're doing. I know I do, all the damn time.
I don't go to counseling but I do have a mastermind group that I talk with daily. We discuss the things we're working on and get help from each other, both technically and emotionally. I very much recommend either joining or starting one.
This was a very brave post. Not because anyone will have a problem with your insecurities,(no decent person would take issue), but rather because it means you have made a MASSIVE step in the direction of being much more secure.
The fact that you are no longer afraid tells me that you are no longer insecure.
[1] http://en.wikipedia.org/wiki/Impostor_syndrome - for clarity, not actually a disease, just something everyone feels once in a while.