Lately, I’ve been trying to simplify parenting to a few key principles.  The goal of the exercise was to lessen my corrective frame of mind.   “Stop doing that”, “leave that alone”, and “put that down” gets old and noisy.  While multiple kids make any parent susceptible to this energy, surely simplification would help me, I thought.

Things always change, so principles don’t come naturally to me.  I’m more apt to always explore than land on an exact way to be.  Regardless, I did arrive at a few principles and, interestingly, I thought there were some personal finance parallels.

There are tons of traits parents want to instill in their children.  We all differ on those traits in magnitude of importance for more reasons than there are traits.  As a starting point, here are a few traits I think parents would welcome seeing in their children:

· Compassion · Strong work ethic · Kindness · Fiscal responsibility · Self-confidence · Open mindedness · Humility · Patience · Honesty · Dependability · Grit · Gratitude · Empathy

These all sound nice.  Although, I wanted to place my focus on “root” qualities and to simplify the mission. 

For comparison, most psychologists agree upon the notion that anger is a secondary emotion – that in order to experience anger, we must have experienced pain or fear first – i.e. our feelings get hurt or we’re afraid of something.  It’s an interesting exercise to ask ourselves when angry or frustrated – what am I afraid of or what has hurt my feelings?

(Side note: Golfers, we’re mad because we’re afraid of looking stupid in front of our friends and/or deep down our feelings are hurt that we haven’t measured up to our own expectations).  How pathetic!

Hence, my focus on “root” qualities.  Are there other traits that make the traits mentioned above more likely to be second nature to our children – or for that matter, ourselves?  One step further, is there a way to narrow the focus on just a few key principles?  As much noise as kids make, maybe my “don’t do that” and “put that down” could be a lot less, too.

My 3 Cs of Parenting:


I remember a great uncle saying once, “I care that my children learn to be happy and self-sufficient.  That’s all.” 

First, I think there’s wisdom in that you can ‘learn’ to be happy.  We might even say it’s a choice that requires lots of practice.  This mode of thinking is a 180 from leaning on external validations to grant happiness.  We look within and walk towards the angst, rather than waiting for the next piece of good news or for someone to pat us on the back.

Second, happiness likely needs clarification.  Definitions vary.  The most long-lasting and sustainable version of happiness that is available to most everyone is peace from mind – or contentment“The mind is a good servant but a terrible master”, (original author up for debate, but not me).   Our past has no regrets or failures, just learning opportunities.  And, in regards to our future, per the old Monopoly analogy, “it all goes back in the box”. 

Every single past encounter is/was food for learning.  And, some day, we’ll put everything we’ve acquired “back in the box”.  That leaves us with ‘right now’ and contentment.  The ability to not continually move the goalposts – neither avoiding sadness nor seeking happiness – might be the greatest source of peace (and wealth creation vehicle). 

Interestingly, this type of happiness paves a path for self-confidence, patience, kindness, and grit. 

With contentment, we’re not in a hurry to expect the next customer, the next pay raise, for someone to agree with us, or to quit on a worthwhile cause.  We don’t need ‘the answer’ now.  Moments of sadness are just as interesting as those of happiness.  Content people aren’t in a hurry to mask insecurities, which usually manifest with a lack of kindness when suppressed.    

In this way, contentment grants us the grit to stay the course and the patience to contend with encounters and people that don’t make sense to us right now – whether waiting for our turn on the monkey bars or for a market in turmoil to rebound.


Maybe curiosity killed the cat.  But the upside potential is too much to ignore.

Curiosity lends itself to qualities like compassion and kindness.  And, compassion, it seems, is a prerequisite for kindness (a separate deliberation).

Often times, I think we confuse pity and compassion.  Pity says, “I feel bad for you because you lost a loved one” or “look at all that war over there – those poor people.”  There is an ‘us’ and a ‘them’.  Pity deals with our emotion (not theirs) – an unpleasant one at that – and, naturally, we rush to mask it or make it go away.  The darker side of pity says, “at least it’s not me”, or “I should be grateful, because I could be *insert circumstances of a less fortunate person*”.

Where compassion is a shared feeling – “I feel your pain for losing a loved one” and “their war is my war”.  It acknowledges a collective mission and a sense of oneness.  This might sound utopian.  The leap from pity to compassion is tricky – because while the words are in the same family – they’re distant cousins.  Compassion likely opens more doors and stimulates more action because we’re actually experiencing someone else’s pain.  The burden is shared. 

The leap requires curiosity.

Do we complete a book or watch a television program and think to ourselves, “Great book/great program, it confirms what I was thinking”, or do we say, “Hmm…I’ve never thought of it that way”?  I suppose both are required – there’s nothing wrong with seeking affirmation so long as it’s not at the expense of drawing a harder line between ourselves and others.

Genuine curiosity blows this useless statement/thought process up: “How could they possibly think that way?” 

Curiosity is antithetical to dogma and identity politics.  Dogma and identity politics, almost by definition, end the conversation.  It creates a barrier – and us and them.  We’ve prioritized leaders who toe the company line over self-exploration or inquiry.

These types of predicaments enforce barriers – and curiosity is the barrier’s enemy.  While it may not eliminate the barrier entirely, curiosity is like taking an eraser to an extra bold line of pencil lead.  And this will serve us better as playground opponents, parents, spouses, bosses/employees, company/consumer, political adversaries, and socioeconomic classes.

(**An aside: I suspect we always need some version of us/them.  Humans function on story.  Story moves the needle of progress.  You need a protagonist and antagonist, otherwise the plot never propels.  The mission is not to bolden the line, however.  The name of the game is to recognize each other’s role in the story and appreciate the necessity of each).


Lenore Skenazy, President of Let Grow and Free Range Kids, famously let her 9-year old son ride the NYC Subway alone.  Despite horror stories of child abductions, she hesitantly gave her eager child permission to head home alone via public transportation.

Skenazy sent her son on his way with a map, a $20 bill, and some quarters (didn’t want to lose a cell phone).  She acknowledges being scared to let him go and afraid of what others would think, but also acknowledges the dilemma of watching too much Dateline and the paralysis caused by fear.    

Despite taking international backlash, Skenazy’s child made it home safe and sound with an abundance of pride.  And, Lenore started a huge movement towards courageous parenting and not succumbing to cataclysmic thinking.

It takes courage to see fear as a mere obstacle, to try new things, to be ourselves, and to do our best.  All of these might leave us with disappointment or even on the wrong side of statistics (as Skenazy’s critics pointed out) – it takes courage to see the unlimited upside of being authentic, sticking with something, or laying it on the line. 

As it turns out, being courageous enough to stay true to ourselves and ignoring the naysayers is the most generous thing we can do for others.  This act far exceeds any tangible present with a pretty bow or even an act of service.  It’s easy to default to giving in the traditional sense (i.e. gifts or a simple favor) because who knows what the reaction would be if we give the world our true selves? 

Skenazy admits to fearing the barrage of ridicule that she ultimately received and the extreme outlier statistics when leaving your child alone – but, she promptly used the attention to create awareness for raising brave children.   How courageous and generous to face her fear and to recycle that emotion for new. 

Even though courage might only apply to taking our first steps or riding a bike at first, this later becomes applicable to larger next steps – like, getting on the subway, applying for jobs, negotiating raises, proposing to a future spouse, having children, leaving a job you hate, ending a bad relationship, and even retiring.  Each next step requires some degree of courage.  After all, it could go wrong, and people might not like us.  But, the upside of facing fear has no ceiling.


Contentment, curiosity, and courage. 

Be happy where we are.  Explore what we don’t understand.  Appreciate fear as a growth vehicle.  The rest can flow from there – for parents and investors.

My mind will be clear for our kids now – this weekend, anyways.

Thanks for reading,


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