“Quality is remembered long after price is forgotten.” — Henry Royce, of Rolls Royce

I was a strange kid.

I practically lived at the library, where I would spend hours crawling around — literally on all fours on the grey industrial carpet, the better to see those lower shelves — and read just about everything. That’s how I discovered programming. And how I ended up reading such business classics as How to Win Friends and Influence People, and SPIN Selling, and A Whack on the Side of the Head. (Along with the entirety of Stephen King’s terrifying oeuvre.)

I don’t remember exactly how I wound up reading The Motley Fool’s Investment Guide at the age of 13, but I definitely did. Then I read pretty much their entire web site.

By then, I had saved up over $1,000 I had earned from various lil gigs.

And thanks to the brothers in foolscap, I wanted to invest it in the stock market.

I did my research - and I wanted to buy AAPL.

It was early 1998. AAPL was under $20. Steve Jobs had just reverse-acquired Apple via NeXT and negotiated the Microsoft coup. I expected good things. The stock market didn’t — when has it ever? — but the P/E ratios were there. (Plus their price-to-cash-stockpile was great, even then.)

This was not long before the iMac, and well before the iPod. Before all those stock splits.

Today that $1,000 would have exploded into a small fortune

(Especially if I’d sold it at its peak last year.)

But no matter how smart and prepared you are at 13, you’re not able to open an investment account. I was a sneaky kid and I’d skirted all kinds of age requirements through trickery and obfuscation, but E-Trade unfortunately required paperwork. Lots of paperwork. Paperwork I couldn’t produce.

That meant I had to get adults to sign up for me.

So I took my money and my research and made a pitch to my parents.

They told me, “No.”

They said, “It’s too risky.”

They said, “You could lose all your money.”

There was no convincing them otherwise. They didn’t care what the experts said. They didn’t care what my research said. They listened, briefly, then shut me down.

No investments for Amy.

What happened to that $1,000 I had saved?

Who the fuck knows?

I blew it on something, and I can’t even remember what. It wasn’t a new computer. It must have been a series of small things, pointless things.


Cash was risky.

I lost every last cent.


I’m >$180,000 poorer today.

That’s the way it is with “risk”

The point of this story isn’t “Amy’s parents were dumb.” They weren’t dumb, they were just unthinking, acting on instincts. Stimulus-response. Like banana slugs. Something novel zapped their gill flaps and they shied away. End of story.

That’s the natural (read: automatic) response to perceived risk. Emphasis on perceived.

It’s not the actual risk that makes us dance away — it’s the uncertainty.

Yes, it’s absolutely natural to prefer a certain loss over an uncertain loss. Yes, you read that right — a certain loss:

  • Certain: There was no chance in hell that a 13-year-old was going to hold onto $1,000 in cash until she grew into an adult.
  • Uncertain: But there was a chance that 50 shares of Apple stock would greatly appreciate.

Uncertainty is uncomfortable because by its very nature, it’s unpredictable. Uncertainty demands thought, consideration, adaptability, imagination… aka mental and emotional work. Certainty, on the other hand, is comfortable, because it’s knowable. Certainty lets us go about our business with no extra effort at all (even if it’s an unpleasant certainty).

So when faced with uncertainty, we often choose… to do nothing.

Then, to justify our inaction, we tell ourselves a lie: By not trying, not dedicating our time, not spending our energy or our money… we’re not just procrastinating. No! We’re actively saving ourselves. We’re saving time, money, energy, risk, fear, pain.

After all, “That action might not pay off!”

But we’re not really saving anything.

The action might not pay off… but inaction will absolutely not pay off.

Time keeps on slippin’, slippin’, slippin’ into the future. It doesn’t matter whether you spend it intentionally or waste it — it disappears all the same.

And money? Money’s pretty much the same. Either you spend it or invest it intentionally — or it has a habit of slipping away. Shit happens.

So, when you think about it — if time and money are going to drip through your fingers anyway

Isn’t it time to invest in yourself?

Instead of embracing another year exactly like all the previous years… wouldn’t it be good to spend your time and money intentionally to create a better result in 2016?

Wouldn’t it be worth it, to risk a little now for the potential payoff?

Uncertainty isn’t the funnest of all experiences, for sure. But neither is waking up January 1st 2017, feeling just like January 1st 2016 and January 1st 2015.

The certainty-loving habit can be tough to break, at first, but it is something you can change.

Your new habit: Flip the fear

In our class — 30x500 Academy — I often have to help our students rewire this natural inclination. Some of them feel paralyzed and tell us that they haven’t tried one of the exercises (like outlining a useful blog post) because…

  • “What if nobody reads it?” or
  • “What if nobody likes it?” or the worst of all,
  • “What if they dislike it and think I’m an idiot or really egotistical to even dare write it and somehow that actually makes me DIE?!”

(Thus far nobody has literally, outloud, painted a causal chain to the point of actual death, but believe me, the implication is there.)

I sympathize — but they’re not paying me for my sympathy (which keeps you stuck).

So I turn it around on them:

  • And what will happen if you don’t do it?
  • If you never do it?
  • What will people think of you then?
  • Who will read your nonexistent blog posts?
  • Who will subscribe to your nonexistent mailing list?
  • Who will buy your nonexistent product?
  • How will you change your life?

That’s the way to break the cycle: Focus on what you will absolutely lose if you don’t act.

Turn the table on the “OMG BUT WHAT IF…!” narrative in two steps:

  1. Let go of what might happen if you try
  2. Take the time to imagine what will absolutely happen if you do nothing

Take a good, hard look at what you’re choosing to endure, forever, by default.

And then…Choose to take a little risk.

You don’t need to go base jumping or pour all your money into penny stocks. Those things are pretty much certain to hurt you.

But too safe is too risky. A lifetime of stasis is risky.

Life, like money and time, will disappear… whether you spend it wisely or not.

So…how will you invest in yourself this year?

How will you make 2016 the year you climb out of the ever-hotter pot of comfortable certainty?

Will you spend your time to learn a new skill?

Will you invest your energy in research and negotiation to get a big raise or new job?

Will you spend money on tools that will help you work better, faster, more profitably?

Will you invest in education?

Will you risk shipping something… even something small… even though people “might not love it”?

If you’re ready to get off your ass in a small way and finish what you start… there’s no better assistant than my book Just Fucking Ship. I wrote it based on my experience coaching hundreds of people just like you — smart, creative, stuck and risk-averse. JFS will help you break down your project and goals into tiny, risk-free nibbles.

Get your butt in gear. Buy now.