12 Rules For Life: The Entrepreneur’s Edition


By now, I’m probably one of the last bloggers on the planet who hasn’t jumped on the “12 Rules for Life” adaptation train.

To say I’ve been busy is an understatement. But since my Mom told me I should do more writing, I’m making more time for that now. (I’ve got some catching up to do).

These “rules” are mostly written for myself. Specifically, my younger self. I wish I’d followed them more closely. I’m doing my best to follow them going forward.

Perhaps you’ll find them useful in some way.

Anyway, here’s my take on it:

1) Don’t rely on what you know.

“Hey Siri, tell me why I’m right..”

The mobile revolution has all but devalued knowing things as a social commodity. Arguments about virtually anything tangible, factual or historical can usually be settled in about 9 seconds by whipping your phone out & searching Google.

There is some value in applied knowledge, as well as intrinsically understanding certain topics – but only if it gives you a tangible edge over the baseline population (in general, in your industry, in your peer group… etc)

This is why conventional education is usually enough to get you into the bottom rungs of a career… but it’s never a fast-track.

In contrast – unconventional results are the result of doing unconventional things.

This is what produces a platform of influence, leverage & power. And if this is your objective, then you’ll need to embrace the fact that knowledge (alone) isn’t enough. You’ll need to take that knowledge and do something very unique with it.

A good place to start is by studying unconventional people.

2) Learn how to surf.

The sport itself is challenging, fun and totally unlike anything else.

But the real reason you should learn to surf is because it requires you to somehow harness the power of a medium that you have absolutely no control over.

The power in those waves (especially on big days) is something that needs to be experienced to be appreciated. Going “over the falls” or getting caught in the impact zone will turn even the most capable watermen into rag dolls, helplessly dragged under by the magnitude of energy released.

Surfing, then, actually depends very little on how hard you paddle, how much balance you have, or otherwise any physical input from your end. (That stuff is maybe 5% of the equation).

Instead, it’s all about positioning, timing, and adaptation.

You need to know where to be, when to be there, and which adjustments to make as you paddle in. It is a sport that demands an intrinsic understanding of your environment before you can even participate – let alone improve your skills.

And mastering the art of harnessing an elemental power – like the ocean – has a very similar “feel” to harnessing the undercurrent of a market, or being able to read the fall line of social momentum.

In both cases, your survival depends mostly on positioning, timing and adaptation amidst an environment outside of your control.  Much moreso than your own strengths or abilities… or how hard you try.

So try it out. You’ll learn a lot more than you might expect.

3) Don’t let your bridges burn themselves.

Often more than the things you choose, the course of your life is dictated by the things you avoid, delay or reject.

This might be opportunities, people, careers, commitments… etc. It’s unavoidable. The proverbial roads not traveled.

Usually the roads we reject are fairly obvious, straightforward decisions. But where this gets a little more challenging is in the things we avoid & delay.

Because while it may be possible to keep the options open for a while, there comes a point where the “unwatered plants” will wither beyond recovery.

So carefully consider what or who you are avoiding, because that bridge is already smoldering.

4) Stay in your comfort zone.

Much of the self-help section at your local bookstore seems to peddle strategies for becoming someone else. Or at least some other version of yourself.

At best, this amounts to well-intentioned, feel-good bullshit.

Aside from medical intervention to treat psychiatric conditions (where the ideal outcome is just returning to optimal baseline, anyway), there is no realistic way to “upgrade” your fundamental personality – the bulk of which is demonstrably genetic. All attempts to do so will ultimately fail, leaving you feeling like a pseudo-failure. Needlessly.

We are who we are.

But this doesn’t mean that we can’t drastically change our present situation. Not only is this a possibility – it’s actually the hallmark of our species. The spectacular success and proliferation of homo sapiens on the Earth has nothing to do with our physical attributes like strength, speed or agility. It has everything to do with our ability to compensate for those weaknesses with tools & ingenuity.

We didn’t get to the moon by getting really good at high-jumps, or flapping our arms really really fast.

So embrace your personality – and maximize your comfort zone. Your default settings will be the best foundation for building momentum you can actually sustain. And instead of focusing on “getting better at __________”, simply compensate for those areas just like our ancestors – through collaboration & tool-making.

This is how you really play to your strengths.

5) Understand that time isn’t money.

It is far more valuable. Guard it relentlessly, because you can never get it back.

You can always make more money. Or in the worst case scenario – at least you can hit the reset button. There are no such luxuries with time. And you also have no idea how much time you really have left.

So don’t squander it on pointless commitments, busywork, biding time, half-assed projects or people who don’t matter.

And in business, focus as much on earning time as you do on earning money. And when the money does come in, use it to further guard your time by choosing investments that aren’t “jobs in disguise”.

6) Don’t invest to win. Invest to not lose.

There comes a point where it becomes clear that, regardless of the polished advisors & their fancy offices, nobody actually knows a goddamn thing about investing.

This was brilliantly highlighted by the man himself, when Warren Buffett won his $1M bet against the hedge fund industry, the argument being that the world’s best active managers couldn’t consistently beat the passive indexes.

As such, you should never pay a premium for someone’s apparent expertise, or specialized knowledge of the markets. Because – plain and simple – they don’t have any.

So at least with the bulk of your capital – instead of trying to get an edge, or chase outsized growth – focus on the factors you can control.

This includes things like management fees, risk-profile allocations, tax efficiency, cash management and rebalancing. (For my fellow Canadians, I recommend being a couch potato).

If you can prove me wrong – awesome, good for you. But the odds, and the evidence, are very much against the invest to win approach over a long enough time horizon. The real winners in finance, the people who can actually stay rich, are the non-losers.

7) Disappoint the right people.

When I was 19, I responded to an ad for a “management position” in the newspaper. They wanted me to show up for an interview a few days later.

It turns out the interview was actually a presentation, convincing a bunch of desperate interviewees in bad-fitting suits (myself included) to sell overpriced vacuum cleaners to impressionable seniors. The presenter was this 20-something dipshit with pretentious shoes & a fake rolex.

I forget his name, but let’s just call him Shallow Hal. Most used car salesmen would probably need a shower after meeting him.

Anyway, the presentation came to its climax, and Shallow started asking who wanted to go on the first “business trip” that weekend, which meant going door to door and begging seniors to let us steam-clean their couch. A few people hesitantly raised their hands. But apparently not enough to satisfy Shallow, so he started pointing at each person, asking what our excuse was for forfeiting such an amazing opportunity.

The finger landed on me, and I explained that I’d just met a girl, and that the upcoming weekend was our first official date.

“I hope she’s worth it bro – huge mistake”.

Disappointing Shallow Hal was the best decision I made in my life. Three years later I married that girl. She’s the best thing that’s ever happened to me. We’ve been married for 13 years now, with two beautiful daughters to show for it.

You will meet many Shallow Hal’s along your journey. These are your social climbers, parasitic suck-ups and vapid, narcissistic status-mongers. They’re usually sociopaths, which means that their charisma can often mask overt self-interest. But eventually, they’ll mess up their lines and reveal their true nature.

It may be necessary to tolerate them for a short while, at certain times. But as soon as possible, put them in the rearview mirror.

And never disappoint someone who matters on account of a Shallow Hal. They are mere props on your movie set. Nothing more.

8) Floss.

Root canals are about $2,200 CAD per tooth on average. And implants start at $4,500 CAD per tooth.

It’s a lot cheaper to floss. Buy one of those water-flosser things if you don’t like using the floss string.

Also… bad breath.

Take this one seriously.

9) Get over yourself – sooner than later.

“I am not young enough to know everything”  ~ Oscar Wylde

There is an obsession with confidence in Western culture. It is the magic formula for making all your dreams come true, becoming successful, getting the girl, finding the treasure, discovering your true self… yada yada.

Confidence doesn’t hurt. It sure beats indecision and paralysis – all day long. But where it becomes problematic is when you’re in uncharted territory… especially if you don’t realize you’re in uncharted territory.

Being assertive and self-assured when you don’t know what the hell you’re doing is a great way to create huge setbacks, waste tons of time, and ultimately look like a giant ass. Needlessly.

This is where a little humility can pay huge dividends.

The key is to be confident about your goals, and then seek advice from a range of smarter / more experienced people about how best to accomplish those goals.

Because you actually don’t know it all, and you’re not as smart today as you will be this time next year. So don’t let your smarter, “future self” down by being a cocky little shit (in the present) that makes unnecessarily dumb decisions.

This especially applies if you’ve had some successes already. Much like investing – though past performance can instill confidence, it does not indicate future results.

10) Re-align with your child identity.

Ever notice how reconnecting with your childhood friends – even if you haven’t spoken in decades – is pretty much effortless?

I’m convinced this is because, as children, we form relational bonds without any pretense. This is when we are our purest form of personality – long before identity-posturing becomes a social utility into adulthood.

Therefore, reconnecting with these people as adults is seamless since you already know their fundamental traits – regardless if they’re now buried under layers of facade to others.

But it’s not just them. You’re also tapping the inner core of your own personality. Your child-self, essentially. This is what puts you at ease, dispels insecurities, and seems to make everything effortless in general. People often refer to this as a state of “flow”.

I think a lot of people are unhappy or unfulfilled because they’re doing stuff that’s totally out of alignment with their child identity. Who they really are. Whether it’s their careers, the focus of their business (or their role in it), their social life… you name it. In a nutshell, and for whatever reason, they’re pretending.

They’re living someone else’s life.

Consider your interests and tendencies as a child. For myself, I loved finding & collecting treasures. I was obsessed with finding the rarest minerals, and I spent all of my allowance money on things like ancient Roman coins, cool fossils, rough gemstones, etc. I’d spend hours poring over the same books, encyclopedias and old magazines that had anything to do with my hobbies.

I think in essence, I was fascinated by things that were rare or difficult to obtain – and I had a tendency to obsess on those topics with a sustained intensity that baffled my parents (along with what few friends I had).

On reflection, this is why I gravitate towards any role or business model where I’m “prospecting”… looking for hard-to-find treasure; finding the secret entrances to a market; identifying overlooked paydirt – and building tools for those purposes. It’s the same interests, just manifesting in an adult context.

That is what feeds my inner child.

What about you? Carefully consider what the “grown-up version” of your childhood interests & tendencies could be… and how you might align with those as an adult.

You’ll be tapping into an primal fuel source that most never discover.

11) Never replace good friends.

Yes, we’ve all heard that stupid quote: Your income will be the average of your five closest friends. What a great example of failing to understand the difference between causation & correlation.

Furthermore, anyone shallow enough to actively exclude good people from their friend group – or even their calendar – based solely on the desire to elevate one’s own status is not the target of this rule. (Those people are sociopaths, and the only thing I can offer them is my contempt).

Rather, this rule is written for entrepreneurs who may find the landscape of their social lives gradually, unintentionally shifting over time.

As you become more established, you will face different challenges than, say, a floundering newbie. And therefore it is natural to seek the company of people who get it. This often means moving “up” the socio-economic ladder to prospect for companionship.

While there’s nothing wrong with this, remember that your career is just a single facet of your life – it shouldn’t consume your life. One of the ways of ensuring that it doesn’t, is to actively maintain friendships with people that have zero connection to your career.

Not only is this simply “not being a douchebag, 101” – it’s also essential for your sanity. Because if all of your friends are more successful than you, then regardless of your current accomplishments, you will feel like a perpetual failure. Your vantage point is always from the back of the pack.

This breeds a deep sense of unhappiness, and I’m convinced that this is why an outsized percentage of objectively successful people are depressed . Their ever-acclimatizing peer group allows them no reprieve. No time to enjoy the fruits of their labour. They are always behind.

You need to actively protect the areas of your life – and the friendships – that have absolutely nothing to do with your career.  Consider that the whole point of starting your business / career was likely to let you spend more time with these people in the first place.

So let these bridges “self-burn” at your own peril. Your prospects for happiness may burn right along with them.

Lastly, and most importantly…

12) Call your Mom.

You might be very busy and important. You might have just way too much going on right now.

Calling your mom – or returning her calls – may seem like an inconvenience at times. Something to try and fit in, when you can.

She might occasionally say things that annoy you. Your conversations might have predictable elements that cause you to roll your eyes on the other end of the line.

She still can’t help but see you as a child, after all.

There will come a day when you will trade every fucking thing you’ve ever accomplished, every dollar you’ve earned, every accolade bestowed upon you, and every day of “crushing it” just for one more conversation with your Mom. Eye-rolls and all.

So call your Mom more often. Tell her you love her.

All the other shit can wait.

Trust me on this one.


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About the author

Chris Rempel

Founder, marketer, writer, futurist.

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By Chris Rempel