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.
