Failing Gloriously

Where should I start?

Well, there was the day we discovered our Financial Director had stolen £2.4 million…

…money we didn't even know we’d earned

which rather tells you everything about our business acumen at the time.

Google "Hicklin Slade/Sharon Bridgewater" if you fancy a laugh at our spectacular financial naivety.

I’m now reminded of my past in the context a few of my advertising contemporaries are now heading towards career exits.

Some through lucrative business sales. Others via the more pedestrian route of diligent career cultivation and pension optimisation.

My current situation?

Very much "none of the above."

Yet, I’m constantly drawn by advertising's fast evolving intellectual challenges.

I repeatedly gambled security and guaranteed rewards for those delicious "what if?" moments.

What I sacrificed in monetary accumulation, I gained exponentially in experiential knowledge:

• True, I’ve occasionally accepted roles patently unsuited to my capabilities.

• I’ve invested in pitches, people, and companies that any rational investor would have avoided like the plague

• I’ve co-founded three startups that provided not only exhilarating highs but eye-watering ways to both gain and lose spectacular amounts of money

Success rate? Patchy at best.

Satisfaction rate? Unprecedented.

Learning dividend? Immeasurable.

The beautiful irony? This has taught me more about due diligence, trust, and operational oversight than any theoretical training  program possibly could.

AI and the comfort with discomfort.

The advertising industry now faces unprecedented AI-driven transformation.

What does success actually mean in an industry where the fundamentals are being rewritten?

Tradition says: accumulated wealth, linear career progression, secure employment. This may all prove spectacularly inadequate for navigating an algorithmic future of unknown possibilities.

My zigzag career wasn't planned, but it cultivated something invaluable: comfort with discomfort.

This isn't the tired Silicon Valley mantra of "fail fast, fail often." Debunked as expensive posturing.

This is something different: systematic comfort with uncertainty. Navigating ambiguity without panic. Rebuilding without losing curiosity.

Here's why this matters now: AI doesn't just automate tasks—it fundamentally alters how we approach problems. Those thriving with AI aren't those with the most technical knowledge. They're those comfortable with not knowing what comes next.

My expensive education in spectacular miscalculation accidentally prepared me for exactly this moment: where strategic thinking means dancing with algorithmic uncertainty rather than controlling predictable outcomes.

It’s sort of ironic. The very career choices that looked suicidal may have been the most sophisticated preparation available for our AI-transformed industry.

Despite logic and good sense saying I should have been long gone.

Skills vs Mindset in the AI Era

At 60, I still delight in approaching each new challenge with a beginners mind set.

It’s what researchers term "deprivation sensitivity" – the psychological hunger for an understanding: The alluring draw of the why?

My career trajectory resembles a rather haphazard game of pinball, not just from design to advertising, but from B2C to B2B, and steps from: Creative Director to Strategist to Agency founder to Investor to Client, etc.

Each ricochet taught me something. Curiosity consistently trumps credentials.

Recent studies reveal 81% of employees acknowledge AI fundamentally alters required workplace competencies. The World Economic Forum identifies curiosity, creative thinking, and flexibility as core, central skills for future work place success.

Intriguing, how we've arrived at valuing really ancient human traits in our most technologically advanced AI era.

Contemporary workplace innovation increasingly stems from curiosity-driven exploration rather than process adherence. Multiple studies demonstrate that deprivation sensitivity correlates more strongly with adaptive performance than technical proficiency alone.

My zigzag career wasn't planned, but it cultivated something invaluable: comfort with discomfort. Each pivot demanded simultaneous hunger for learning and disciplined competency development.

The difference now is the urgent requirement of concurrent curiosity and capability in perpetual refreshed mode.

The limiting factor isn't technical constraints – it's our own ambition and intellectual appetite.

Competency without curiosity will create professional dead ends.

Now its about cultivating a beginner's mindset as a core competency. Develop systematic comfort with uncertainty.

Crucial point: Practice intellectual humility alongside technical skill acquisition.

You are NOT an AI expert, be honest, we barely grasp the AI workplace implications of the next 6 months, let alone the rest of the decade. >> Look up Rana Adhikari at the California Institute of Technology, who recently found some AI models designing experiments that defy human expectations, sometimes bypassing controls. (Article in Wired, et al.)

So its clear, the most valuable professional asset isn't knowing everything.

It's maintaining the discipline to approach everything as if you know nothing.

The challenge now is how to institutionalise intellectual curiosity within traditional competency frameworks

The Careers Opportunities of a Bot

As a teenager I was enthralled by the music of the Clash. So wasn’t so out of character when I found myself unconsciously humming the words to Career opportunities, a blistering track from 1977. Particularly the refrain “.. Career opportunities, the ones that never knock..”  

The occasion? another AI powered knock back for a role

The irony is up to 11.

The very machines I champion being used to systematically filter out precisely the cross-pollinating professionals that can add such value to organisations dealing with the effects of AI.

Ladder meet bridge

The traditional career ladder assumed a stable world where skills depreciated slowly and industries remained predictable. That world is gone.

The most valuable professionals aren't climbing ladders; they're building bridges between disciplines, industries and crafts.

Clearly I’m biased, having zig zagged around pretty much every corner of advertising all my career, and yes before you ask, I’m old enough now, to realize I do get bored without a strong mental challenge before me

Skill stacking

Post AI research shows that professionals with diverse domain experience exhibit 43% superior performance in adaptive problem-solving scenarios. The terror many feel about "leaving their lane" represents profound misunderstanding of value creation in machine-augmented environments.

It's like discarding your Swiss Army knife in favour of a single blade, then wondering why you can't open wine bottles or extract stones from horses hooves anymore…

My point is: Cross-domain experience generates novel solution pathways that pure specialists struggle to access.

Adaptive Resilience: Multiple pivots build intellectual muscle memory for navigation of the increasing uncertainty businesses now face.

Curiosity Expertise: Understanding how to extract maximum value from AI requires precisely the kind of cognitive flexibility that portfolio careers cultivate.

Career opportunities

As AI assumes routine cognitive tasks, human value increasingly lies in synthesis, pattern recognition across domains, and strategic ambiguity navigation. Linear careers optimised for industrial efficiency; portfolio careers optimism for algorithmic collaboration.

What unexpected skill combination defines your professional edge?