How do we learn best? From our successes or failures?

Personally, I’ve always learned from getting something wrong, then reflecting on it.

That’s why I’ve always been a bit of a gambler.

I like to take a controlled risk. Way back when I was a scrappy digital marketer, managing ad budgets at Bath & Body Works or wrangling wild concepts for tech startups in NYC, I clung to a simple principle:

80% of the spend on proven winners, and 20% on big bets.

I don’t know where I learned this principle. I just know that it has worked for me.

20% put towards new risky campaigns or ideas, felt a bit like wearing a safety harness while still bungee-jumping off a cliff – thrilling, but not entirely reckless.

That lesson from 25 years back stuck with me: real success demands that we invest a slice of our budget in ventures into uncharted territory.

Fast-forward to today, as a founder of a 150-person digital agency, I’m shocked to see this principle vanish.

Marketers seem reluctant to gamble even the smallest fraction on new ideas.

Maybe it’s the fear of having to explain a “wasted” budget line, or the pressure to report safe numbers.

But if we don’t treat our budgets like an investment portfolio, how will we discover the next big breakthrough?

Digital marketing, much like life, rewards those who step off the well-trodden path.

A bit dramatic? Maybe.

But if we forever rely on safe bets, we’re basically the investment equivalent of keeping our money under the mattress – no chance for growth, no heartbreak, but … zero upside!

I get that not every marketer, or every boss, craves the thrill of a big, hairy bet.

But if we learn so much more from mistakes than we do from successes, then we need to program them in. That means taking controlled risks whenever we get the chance.

In truth, I’m still figuring out how to balance caution with ambition. Some days, I’m the confident risk-taker, other days, I’m wearing body armor under my hoodie because I’m terrified of messing up…

Yet I keep returning to that fundamental question: do we play to win or play not to lose?

If you’ve got a perfectly rational reason for squashing the 80/20 rule, I’d love to hear it – no sarcasm intended (okay, maybe a little).

Leaning into the 80/20 rule requires both fierce determination and a touch of vulnerability. Here’s how I’m attempting it (emphasis on ‘attempting’):

1) I push myself out of my Comfort Zone – I remind myself that playing defense (ahem, autopilot campaigns) is comfortable but rarely yields breakthroughs.

2) I learn new skills – I always ask my team to keep a dedicated slice of the ad budget. Start with 5% if 20% sounds terrifying – to test new channels, creative angles, or audiences every single week or month.

3) I want to create not just average, but exceptional value – I ask my team to measure results obsessively, but I also cut everyone all the slack when experiments flop. After all, flops are just stepping stones to bigger wins.

4) I move up faster and get better – I celebrate the small victories and openly share the “learning opportunities” (read: fiascos :). Turns out, transparency fosters a culture where risk isn’t … a four-letter word. If I’ve learned anything, it’s that bravery today builds the momentum for tomorrow—both in marketing and in life. Let’s keep testing, and see where that leads us. I’m still learning daily.

(Btw, the above 4 steps follow my Return on Marketing Career (RoMC) framework - to learn about RoMC, read this post.)

In a 2022 Deloitte “CMO Survey” of over 300 marketing leaders, 54% who allocated at least 20% of their budgets to untested channels reported a 40% higher brand engagement year over year.

Harvard Business Review has similarly championed structured risk-taking in marketing, highlighting that “only by systematically testing new ideas can organizations outpace competitors.”

Meanwhile, Google’s 70-20-10 principle, originally introduced under Eric Schmidt’s leadership, recommends investing 70% of resources in core products, 20% in related growth, and 10% in breakthrough innovations.

This framework helps maintain stability while fueling bold experimentation.

A 2019 Boston Consulting Group study revealed that companies committed to an 80/20 or similar mixed approach were 1.5 times more likely to achieve higher-than-average ROI from digital campaigns.

Finally, Forrester Research emphasizes that performance marketing success hinges on balancing caution with innovation, advising that “brand equity suffers when marketers remain perpetually risk-averse.”

Taken together, these sources reinforce the notion that a strategic blend of safety and risk can unlock superior returns, both in digital marketing and organizational growth.

No wonder the 80/20 concept endures.

If you’d like to discuss your career journey with me one-to-one, please feel free to email me at [email protected] or message me on LinkedIn.

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