I had this teacher in high school, very unconventional older man, keen on deviating from the program to impart insightful life lessons to 14-year-olds once in a while, or spend an hour talking about his cat.

He once told me, in front of the whole class and in a distinctly sarcastic tone:

You just do things your own way, don’t you?

I was dumbfounded, taken aback. Believe it or not, I was really shy at the time, so it took a lot to answer “Yeah, it’s worked well so far“. He chuckled, and told me to be careful. “It won’t always be this way“, he added.

I didn’t really understand him at the time, and now, nearly 15 years later, I understand his warning even less.

Conventional knowledge

I believe what he meant was there is a conventional, “tried & true” way to do things, and that it exists for a reason. That’s not wrong in itself.

While he recommended I adhere to convention for my own sake, I couldn’t help see established patterns as, in the best case, a canvas for experimentation, and in the worst, a cautionary tale.

I’ve made a lot of unconventional decisions, and I’ve failed at a lot of things. It’s interesting to notice there’s little to no overlap between the two.

Successful decisions I’ve made were either based on intuition, or researching from the ground up, forgoing conventional knowledge entirely, or at least examining it closely beforehand.

Failed decisions were based on “that’s the way things are” mentality, trusting authority, or blindly following advice.

  • Trying & failing college. Twice.
  • Gaining weight in the first place.
  • Getting into ill-advised relationships, both personal & professional.

I’m not trying to shift blame where I messed up. Those decisions were ultimately mine, I was either too intimated, overwhelmed, or uninformed to make them properly.


Every time I go towards an unconventional way, I encounter major resistance from my relatives and friends.

  • “That’s not the way you’re supposed to do things!”
  • “It’s dangerous!”
  • “Do you think you know better than the experts?”

It’s gotten to the point where if I’m not pissing at least one person off with a decision, I’m probably not being bold enough.

There are a lot of reasons why people, some of whom genuinely care about you, would give counter-productive, if not downright shitty advice.

They want to protect you

People close to you, most often parents, will instinctively try to shield you from risk and hardship. While this comes with the best of intentions, they might be keeping you from realizing your potential by guiding you to the path of least resistance.

It worked for them

They followed the TriedNTrue® way, and it yielded good results for them. Why would you not do the same?

There might be a generational gap, a world that’s radically changed in between, or you might simply be too different to do things the same way. Advice pertinent to a field might be ineffective in another.

They aren’t used to deciding

Most people live life on auto-pilot. They defer to authority from kindergarten to retirement. Teachers, then boss, then spouse, then state, etc. I’m not necessarily being critical, to each their own. But it would make sense that such a person would be reticent, if not alarmed when a person close to them goes against the grain.

They don’t want you to succeed

Sadly, this seems to be the most common. Other people have a fixed mental description of who you are, used to build their world view, interaction map & social hierarchy. We all do that, it’s automatic. When you step out of that canvas, it triggers resistance. For the human brain, it’s easier to convince another to step back in the canvas than to update the whole model.

We’ve all heard “you’re perfect just the way you are” at least once. They’re not being nice, their brain is just being lazy.

Others live with a “crab bucket” mentality: they’d rather nobody succeed if they can’t. They’re the dangerous ones. They’ll give you purposefully deceitful advice to ensure you fail.

The unconventional way

Given the many pitfalls of conventional knowledge, you should pay attention to the following points while exercising your decision-making process.

Knowledge might be outdated

The “way things are” oughta be renamed “the way things were“. Even in professional circles, a surprisingly high amount of people don’t bother updating their functional knowledge after graduation.

Advice always comes with intent

As described above, advice is seldom purely objective, even less so from people close to you. Is their advice in your best interest, or theirs? In the rare case where it’s both, go nuts (and keep them around).

Gather as much data as you can

Your intuition might be on point, but you can’t make an appropriate decision without sufficient data to back it up. Read studies, survey your market, study peers or competition in the same area to suss out the things to do (or to avoid!).

In conclusion

This is your life, and it’s up to you to live it. Blindly following advice, resting on established doctrine can only lead to an unfulfilled life of regret. Be critical of conventional knowledge, be critical of friendly advice. Be daring, but well-informed.

You might still fail, or you might win big. At the very least, you will have done your due diligence of critical thinking.

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