Contrarian thinking only pays off when you're contrarian AND right. Instead, what you need to do is take intelligent, considered risks/opportunities while thinking through to (at least) the second-order consequences of those immediate actions.
Jumping off a cliff is no doubt contrarian thinking (you just need to do the exact opposite of everyone else, right?) - but I doubt you would reap much benefits from this particular type of contrarian thinking.
On the other hand: skipping college and channeling the money and time saved to get a head-start on learning sales & marketing, product development and other key business skills?
That's contrarian thinking (thankfully less so in recent years) AND right.
The key is in getting the qualifier “and right”, well, right.
You don’t want to be contrarian for the sake of being contrarian.
Now in many cases it’s hard to tell if your decision or action will ultimately turn out right - but sometimes it’s obviously and plainly not right, so why the heck are you even doing it?
I've met more than my fair share of people who by *default* always “do the opposite of everyone else” because that’s “jUsT hOw I aM”.
For them it’s an almost identity-level issue – i.e. “I will do the opposite because that’s how I define myself”
(In other words, “I’m different and it’s personally important to me to be different because it undergirds one of my core inner identities”)
Frankly (and in my opinion) it’s a bit of a stupid approach to life to knowingly adhere to any sort of rigid, dogmatic approach just for the sake of adhering to said rigid, dogmatic approach.
It’s also an overly simplistic way of looking at the world - and a very wrong one that could produce very real negative consequences.
And don't also just reflexively "do the opposite of everyone else" because the latest and greatest rah-rah-rah popular business book or celebrity "thought leader" du jour tells you to (I have a few in mind, but I won’t name names)
Take the risks you need, but make sure you're also doing it in intelligent, considered ways while thinking through to *at least* the second-order consequences of your immediate actions.
As a bootstrapped founder (particularly a first-time one) you probably have a lot less margin for error than others with a secure 9-to-5 job or those with cash in the bank from an exit.
Enjoy your weekend.