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Nobody who fits in ever becomes wildly successful, which is the mindset shift that changed both my social life and my business. My blog failed for its first few years specifically because I wrote what was already out there and refused to take a position on anything.
In this solo episode I share some genuinely embarrassing childhood stories to make the point, including the classmate who built a reputation as the funniest kid in third grade by repeating my jokes out loud while I stayed silent.
Below are the five lessons that came out of finally speaking up, and why each one applies directly to building a business.
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Table of Contents
Key takeaways
- Nobody is watching you as closely as you think. The paranoia is entirely internal.
- Your fears are almost always irrational. We invested $630 and had nothing real to lose.
- Playing it safe killed my blog for years, until I started expressing actual opinions.
- Following the crowd guarantees mediocrity in stocks, in products, and in marketing.
- Everyone is strange in some way, and successful people leverage it rather than hide it.
- Only weigh opinions from people who matter, since you will never meet the vast majority of critics.
- Hate mail is a signal you are working. Nothing happens until you strike a nerve.
- A change of environment resets your persona when a peer group has pigeonholed you.
Why I stayed quiet for most of my childhood
I was raised to fit in, work hard, and let my grades speak for me.
The result was being painfully shy. I never spoke in class, rarely started conversations, and was the quiet kid in the corner who did well on tests.
What made it worse is that it was not what I wanted. I wanted to be liked, and pictured being the popular kid rather than the nerd.
The obstacle was fear of saying the wrong thing, which defaulted me into silence.
The clearest illustration is third grade. A classmate sitting next to me found my running commentary funny enough that he started shouting my one-liners to the room.
Everyone loved them, because they were my jokes, and he spent the year known as the funniest kid in the class.
I never had the courage to say them myself, and he did give me the useful information that my personality was actually funny.
Why a change of environment lets you reset
Three weeks at an overnight camp before ninth grade is where I actually changed.
The reason it worked is that nobody there had any preconception of who I was.
That removed the consequence entirely. I could say whatever I wanted knowing I would never see any of these people again.
What I discovered is that simply acting like myself made me stand out, and I was popular for the first time.
The general lesson is that a peer group holding you in a fixed persona is difficult to escape from inside it. Sometimes changing environment is what resets it.
Lesson 1: Nobody is paying attention to you
Insecurity produces the conviction that everyone is monitoring your every move, and the opposite is true.
My own worst example was spending an entire evening sitting cross-legged on a sofa so nobody would notice a stain on my pants.
The domestic version arrives whenever my wife asks which earrings to wear to a party. Both look good, and nobody at the party will be evaluating either.
The reality is that everyone else is occupied with themselves. We consistently overestimate how much of anyone’s attention we occupy.
Lesson 2: Your fears are usually irrational
The imagined consequences are almost always far worse than the actual ones.
When we launched our store, we were genuinely afraid of losing everything. I pictured being ridiculed by my Stanford classmates for selling handkerchiefs online, and had recurring nightmares about us begging at the roadside.
The actual exposure was $630 plus a lot of work.
The worst realistic case was that the business fails, my wife returns to work, and life continues.
The same reframing works socially. I used to fear approaching strangers, and now I ask what the worst outcome actually is. Rejection almost never has any lasting effect on anything.
Lesson 3: Playing it safe is why my blog failed
I spent my first years blogging producing content that had no reason to exist.
The approach was writing tutorials from what I read elsewhere and what I did with my store, sticking to facts and avoiding opinion.
The motivation was wanting everyone to agree with me. I said nothing critical about the tools I used and never departed from accepted best practice.
The result was a blog that failed for years, because it was a restatement of what was already available with no perspective attached.
Traction arrived the moment I started writing what I actually thought.
Someone once told me you are not successful until you receive your first piece of hate mail, and I believe it. Nothing happens until you strike a nerve.
Lesson 4: Fitting in guarantees you stay ordinary
The lesson transfers directly from trading stocks to running a business.
Warren Buffett’s advantage is buying when nobody else wants to and not panicking during a selloff, which is entirely about not following the crowd.
The business version is identical. Selling the same products as everyone else drives prices toward zero, and copying everyone’s marketing produces no sales.
The uncomfortable prescription is that the path forward is being strange.
Anyone who claims they are not strange in some way is hiding it, and the sooner you accept your own eccentricity the sooner it starts working for you.
The successful people I know all lean into it. Pat Flynn uses his geekiness and love of a specific film franchise to be relatable, and Derek Halpern’s snark is why people listen to him.
My own version is sending Photoshopped images to podcast guests as jokes, like threatening to expose the founder of a green smoothie company drinking an elaborate coffee drink instead.
Lesson 5: Only weigh opinions from people who matter
Caring what people think is human, and you can choose whose opinion counts.
A decade of blogging has produced a fair amount of genuinely hateful mail.
The reframe that works is that you will never meet 99.9% of the people who dislike you, which makes their opinion structurally irrelevant to your life.
The opinions worth weighing come from people you trust and admire.
Meeting critics in person is also instructive. The few I have spoken with over video or in person were perfectly pleasant, because anonymity makes people considerably bolder than they are face to face.
Why weird beats conformity
The turning point was when I stopped suppressing my own personality.
The instinct not to rock the boat is natural, and blending in is precisely what prevents anyone from noticing you.
Almost nothing you are afraid of turns out to be as frightening as anticipated.
Not everyone will like you, and being yourself is the only way to find out who does.
People consistently gravitate toward someone with a clear opinion, whether they agree with it or not. Trying to please everyone pleases nobody.
Frequently asked questions
How do you stand out in business?
Stop doing what everyone else does. Selling the same products drives prices down and copying everyone’s marketing produces no sales. Leaning into whatever makes you unusual is what makes people notice you.
Why do most blogs fail to get traction?
Because they restate what already exists. My blog failed for years while I wrote safe tutorials from other people’s material, and it gained traction the moment I started publishing actual opinions.
Is it bad to get hate mail?
It is a signal that you are working. Nothing happens until you strike a nerve with an audience, and content nobody could disagree with is content nobody has a reason to share.
How do you get over fear of failure in business?
Compare the imagined consequence to the actual one. We invested $630 in our store and imagined losing everything, when the realistic worst case was that my wife returned to work.
Does anyone actually notice your mistakes?
Far less than you assume. Insecurity produces the conviction that everyone is watching, and everyone else is occupied with themselves. I once spent an evening sitting cross-legged to hide a stain nobody would have seen.
How do you handle online criticism?
Weigh opinions only from people you trust and admire. You will never meet the vast majority of critics, and the ones I have met in person were considerably nicer than they were behind a keyboard.
Can changing your environment change your personality?
It can reset how people perceive you. A peer group that has pigeonholed you is hard to escape from inside it, and three weeks somewhere nobody knew me is what let me actually speak up.
Should you take strong positions in your content?
Yes. People gravitate toward someone with a clear opinion whether they agree or not. Trying to please everyone produces content with no soul that pleases nobody.
