Non-linear Career Development

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I’ve recently been asked several times, mainly by younger people in their 20s, what do I actually do for work, and how did I end up doing what I do?

Regular readers will know that career development is a topic I have commented on many times in past articles, either as a result of my coaching and consulting engagements, or in response to the current state of the world.

This month marks 10 years since I started working in the crypto and digital asset industry. While it’s not a full-time job, and I serve as a freelance consultant, it’s now the longest period of continuous “employment” I have had in a single role, sector or organisation. Not a bad gig for something that started out almost by accident – it certainly wasn’t part of a well-planned, linear and structured career path!

If I look back on my career, there is probably one constant factor – that at heart, I am an editor, and by and large, I have always worked in “content”, whether in traditional publishing, on-line data, or new media. My specific roles and the organisations I have worked for have been varied, but the output or format has been consistent.

After graduating in law in the early 1980s, I spent a stressful and frustrating few years as a paralegal in local government, helping people with housing difficulties or facing homelessness. Within 5 years, I was burned out, and needed a change.

So I retrained, and completed an evening class in journalism and sub-editing, run by a couple of senior editors from Fleet Street. However, my aspirations of working for glossy titles or cultural magazines came to nothing, as by this time I was probably too old to be hired as a trainee journalist or on a graduate program. Luckily, I spotted an ad for “legal editors”, and putting my formal qualification together with my recent night school learning meant I was exactly in the right place at the right time.

That initial foray into publishing took me from London, to Hong Kong, and then to Australia, and along the way I transitioned into financial services, market data, international roles, business development, product management and digital assets. And I still use my legal knowledge every day, and “content in context” (hence the name of this blog) is relevant to everything I do.

Fast forward to 2026, and here I am running a media company serving the crypto industry. (More on that next week).

Looking back, there was no master plan, or grand strategy. My curiosity just kept pulling me from one industry or one role to the next.

1. Law taught me how to think.
2. Publishing taught me how to communicate.
3. Capital markets taught me financial infrastructure.

And when I walked into a Bitcoin pitch night in Melbourne more than 10 years ago, I felt at home (which is perhaps a little weird when you think about the somewhat impersonal, anonymous and 100% on-line world of crypto).

I appreciate that my career path looks messy from the outside, and it’s not for everyone, but it all fits in the bigger picture.

I didn’t become a lawyer, but I use legal thinking every day.

I left traditional finance 15 years ago, but that background is largely the reason I ended up working in crypto and digital assets.

If you’ve had a non-linear career, you will probably recognise the following:

Every skill you have picked up, every industry you wandered into, and every unplanned detour has been accumulating in the background.

You don’t necessarily connect the dots looking forward, you only ever connect them looking back.

But in the end, it all fits in the bigger picture.

Next week: My 10 Years in Crypto

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My thanks to Simian Giria for helping to initiate this topic.

Old School Ties

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Last month I visited my old high school to attend the annual reunion. This was the first time I’d been to a formal alumni event, only 46 years after I left.

That’s not to say I haven’t kept in contact with my school mates, despite living on the other side of the world. Among the Class of ’79 who had turned up, I’d seen all but one of them in the past couple of years, and I try to catch up with this group each time I go back to the UK.

Despite the passing years, I was surprised by how much the old place felt so familiar – I guess having more than 450 years of history behind it means that tradition runs deep.

At the same time, it also felt quite alien – I realise that although I am originally from the local area, I feel less and less of it. Nevertheless, I was reassured that however much things may change, my immediate circle of school friends endures.

Why should that be so? Yes, “old school ties” can form the basis of life-long relationships, linked to a specific educational institute; and those ties can be both tangible and metaphorical. But more importantly, these connections are built on a mix of broad common values, our shared experiences, and the age we met.

 

More on AI Hallucinations…

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The mainstream adoption of AI continues to reveal the precarious balance between the benefits and the pitfalls.

Yes, AI tools can reduce the time it takes to research information, to draft documents and to complete repetitive tasks.

But, AI is not so good at navigating subtle nuances, interpreting specific context or understanding satire or irony. In short, AI cannot “read the room” based on a few prompts and a collection of databases.

And then there is the issue of copyright licensing and other IP rights associated with the original content that large language models are trained on.

One of the biggest challenges to AI’s credibility is the frequent generation of “hallucinations” – false or misleading results that can populate even the most benign of search queries. I have commented previously on whether these errors are deliberate mistakes, an attempt at risk limitation (disclaimers), or a way of training AI tools on human users. (“Spot the deliberate mistake!) Or a get-out clause if we are stupid enough to rely on a dodgy AI summary!

With the proliferation of AI-generated results (“overviews”) in basic search queries, there is a tendency for AI tools to conflate or synthesize multiple sources and perspectives into a single “true” definition – often without authority or verified citations.

A recent example was a senior criminal barrister in Australia who submitted fake case citations and imaginary speeches in support of a client’s case.

Leaving aside the blatant dereliction of professional standards and the lapse in duty of care towards a client, this example of AI hallucinations within the context of legal proceedings is remarkable on a number of levels.

First, legal documents (statutes, law reports, secondary legislation, precedents, pleadings, contracts, witness statements, court transcripts, etc.) are highly structured and very specific as to their formal citations. (Having obtained an LLB degree, served as a paralegal for 5 years, and worked in legal publishing for more than 10 years, I am very aware of the risks of an incorrect citation or use of an inappropriate decision in support of a legal argument!!!)

Second, the legal profession has traditionally been at the forefront in the adoption and implementation of new technology. Whether this is the early use of on-line searches for case reports, database creation for managing document precedents, the use of practice and case management software, and the development of decision-trees to evaluate the potential success of client pleadings, lawyers have been at the vanguard of these innovations.

Third, a simple document review process (akin to a spell-check) should have exposed the erroneous case citations. The failure to do so reveals a level laziness or disregard that in another profession (e.g., medical, electrical, engineering) could give rise to a claim for negligence. (There are several established resources in this field, so this apparent omission or oversight is frankly embarrassing: https://libraryguides.griffith.edu.au/Law/case-citators, https://guides.sl.nsw.gov.au/case_law/case-citators, https://deakin.libguides.com/case-law/case-citators)

In short, as we continue to rely on AI tools, unless we apply due diligence to these applications or remain vigilant to their fallibility, we use them at our peril.

 

Cultural References

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Most days I like to try and solve a cryptic crossword. It’s a hobby I picked up from my dad, when I was in my early teens. He probably regretted introducing me to this particular pastime, as we used to compete for the newspaper…

I think I have persisted with this hobby because I have an innate interest in word-play, and solving puzzles helps to maintain my cognitive agility.

Apart from having a large vocabulary and an understanding of the rudiments of solving different types of cryptic clues, it also helps to have wide general knowledge. In my own case, this is underpinned by having received a “classic education” – that blend of critical thinking, an inquisitive approach to learning, and a mix of the liberal arts, formal science and a hint of classics.

Cryptic clues frequently involve specific and oblique references to weights and measures, chess, bridge, languages, history, geography, the arts, literature, politics, current affairs, religion, sport, law, technology, entertainment and the sciences. Puzzle setters also rely on lexical techniques such as abbreviations, palindromes, homophones, anagrams, synonyms, antonyms and phonetics to construct their clues.

Many times, I find I just “know” the answer because some word association triggers mental recall. Often, though, clues are solved by a process of deduction and logic to parse the cryptic component to align with the factual meaning or definition.

I am increasingly challenged by references to current popular culture. Sometimes, I can deduct the reference to the name of a chart-topping singer or title of a Hollywood movie franchise – and not from hearing the music or watching the film.

It does make me think about what defines “general knowledge” – the stuff you should know without having to use a search engine? The public canon obviously shifts and evolves over time, but increasingly our individual knowledge is becoming fragmented, siloed and insular – not helped by algorithms designed to serve up more of the same or push us deeper into very narrow bands of information. Obviously, tastes and currency change with the times, but what constitutes a core foundation of personal wisdom and understanding to help us navigate the world?

This thought struck me recently during a family games night. One of the teenage participants was given a particularly difficult film title in a round of charades: “Dog Day Afternoon”. I was certain our young contestant had never seen (let alone heard of) this controversial 1975 movie (but which even now, seems highly topical). Yet, our plucky player rose to the challenge, and acted out a very literal interpretation, which made it relatively easy for the rest of the team to solve. It was great to see the process of deduction based on limited information!

So, maybe as long as we keep teaching basic general knowledge plus strong problem-solving skills, we’ll be OK?