The great thing about business is that business is really about people, much as tech folk would like to convince you otherwise.
There’s never been a truer adage than “people buy from people”, for example.
Or the well-worn advice that people are more likely to do business with those they know, like, and trust.
These are entirely human judgements and, like it or not, almost entirely subjective.
It’s fair to say our tech overlords occasionally do a half-decent job of faking all of those things – certainly good enough to fool some of the people all of the time – but, like all fakery, eventually the chickens come home to roost.
There really is no substitute for humanity in business.
You can pretend otherwise, and believe everything is just about 1s and 0s. But you’re only fooling yourself.
And even to the extent it works, it’s vastly more expensive and resource-intensive to fake things than to be human. Which means the fall from grace, when it comes, it much harder and deeper than it would have been otherwise.
If you doubt me, consider the amount of effort Enron put into trying to maintain the illusion of being successful – up to and including committing outright fraud, for which several people went to jail – when they could have done very nicely out of just being honest about their business.
And if you’re not old enough to remember Enron, stay tuned. I’m expecting a similar dynamic to present itself in the course of this autumn’s slate of IPOs for AI companies.
But Enron’s failure was fundamentally a human failure, not a business one. The human failure came first, the business failure followed.
By the same token, extraordinary humans can make great business decisions. Sure, it requires some creativity, some ambition, some hard work. And humans are flawed, of course, but they’re several orders of magnitude less flawed than tech solutions.
Not every decision a human makes is a good one. But when humans make good decisions, a whole new world opens up.
So today, I’d like to highlight three great decisions made by humans as an example of this phenomenon.
As it happens, they are all women. And, as it happens, they are all examples from the music industry. But every one of these are phenomenal decisions – brave, creative, insightful.
Decisions you’d never make based on a spreadsheet.
These decisions came from the heart, and they are decisions only a human could make.
All three are the opposite of logical. There were millions of really good reasons to do the exact opposite, yet these three women zigged when the world was telling them to zag.
I admire them all immensely.
Taylor’s version
The most recent example is from Taylor Swift – someone so famous that I don’t need to explain who she is, even to people who aren’t fans of her music.
There is a little twist to this tale, even if you think you already know it, so stay tuned.
As a teenager, Taylor Swift signed a recording contract in which the rights to her master recordings belonged to her record company. In fairness, that’s not an entirely unprecedented arrangement in the music industry.
In the blink of an eye, though, Taylor Swift went from being a teenager writing songs on the bedroom floor in her family home to being one of the biggest recording artists on the planet.
After a few years she was so successful, Taylor Swift wanted to buy the master recordings so she owned her entire body of work. However, as a result of some murky, and much-disputed, events (which are not essential to the point of this story) that didn’t happen.
Her record company was bought out by a famous music industry manager, and soon after re-sold to a private equity outfit who proceeded, as private equity companies do, to sweat the assets of the business they’d bought.
Determined not to be bested by her record company, Taylor Swift then re-recorded all her early albums in what became known as “Taylor’s Versions”, so that she now owned the masters of her “Taylor’s Version” recordings of her back catalogue.
With a legion of adoring fans, sales of her original recordings plummeted and sales of the Taylor’s Version recordings soared, even among people who had previously bought the originals.
I don’t know what happened in detail as that isn’t publicly available information, but I think it’s safe to say that value of the income-producing assets the private equity firm bought tanked and their investment was no longer the gold-plated opportunity it had initially appeared to be.
There are two little twists to this story.
The better-known one is that, in 2025, some five or six years after the original buyout of her record company went through, Taylor Swift did come to an agreement to buy her original master recordings back.
By taking a stand, thinking creatively, and being determined not to be beaten, Taylor Swift got what she wanted in the end. All credit to her for demonstrating some top-notch human decision-making there.
The other twist, which I only discovered recently, is that American Idol winner Kelly Clarkson had a hand in this too. Back in 2019 she tweeted to Taylor Swift that she ought to re-record all her songs so she would own the masters, and offered her support.
That’s not to say that Taylor Swift didn’t have the same idea independently – I have no idea one way or the other. And to give Kelly Clarkson full credit as a human being, she has since acknowledged in interviews that Taylor Swift would probably have come up with the same idea herself anyway, so she isn’t looking for any credit.
Wherever the idea came from, though, Taylor Swift executed it to perfection and saw through a course of action that very few people would have taken.
As business moves go, what Taylor Swift did is one of the best ever.
All because she thought like a human, not a machine. And because she said “no” when it would have been so much easier just to say “yes”, and take whatever crumbs were on offer from her record company.
Dolly Parton
Dolly Parton is legendary in the world of country music – somewhat less so outside it. She is, however, one of the best-selling musical artists of all time. Along the way she has picked up 11 Grammy awards and written some tremendous songs – I can’t listen to “Coat of Many Colours” without finding a tear in my eye, just for starters.
Dolly Parton started performing as a child, had some success writing songs for other people along the way, and some modest success in her own right as a singer.
In her early 20s, Dolly was invited to join Porter Wagoner’s immensely popular weekly country music TV show, which gained her considerable public recognition. But she was very much playing second fiddle to an established star and her solo career took a back seat for a while even though a series of duets with Wagoner did well in the country music charts.
She did keep writing songs, though. Standards like “Jolene” were written about this time.
Eventually Dolly Parton decided life as the second act in a duet wasn’t really what she wanted, and spilt with Porter Wagoner, even though I’m sure she could have had a very decent long-term career had she stayed.
That was human decision number one. The logic might well have said “stay”. The heart said “go”.
Human decision number two came along shortly after.
In 1975, Dolly Parton wrote and recorded a song called “I Will Always Love You” about her split with Porter Wagoner, which went to Number One in the country music charts.
Particularly if you’re a Brit, you almost certainly don’t know that version of the song.
But, wherever you are in the world, I can guarantee you know Whitney Houston’s cover for her 1992 film “The Bodyguard”. That version spent 14 weeks at the top of the Billboard Hot 100 in and sold over 25 million copies worldwide.
What is not so well known is that back in the mid-1970s, soon after Dolly Parton wrote “I Will Always Love You”, she was approached by Elvis Presley’s manager to see if she would let Elvis record her song.
Now, at the time, there were probably few better outcomes for a songwriter than having Elvis record one of your songs. And, to be fair, I think he’d have made a tremendous version of Dolly’s song.
The only problem was, the standard deal when Elvis recorded a song was that he’d get half of the publishing royalties.
Dolly Parton reached the very human decision that she wasn’t prepared to sign away half the rights to the song she’d written and said no.
The easy, logical answer would have been to agree to Elvis’s terms. Dolly Parton took a human decision.
I know this is speculation, and involves 20/20 hindsight, but if Elvis had recorded the song he’d probably have had a decent hit with it. It is, however you look at it, a great song.
But I doubt the producers of “The Bodyguard” would have chosen such a well-known song as the centrepiece of their Whitney Houston film – they needed a great song, but not one that everybody knew already.
So Dolly Parton traded a relatively certain million-seller from Elvis for an iconic performance by Whitney Houston and sales of over 25 million copies. Even though at the time she turned Elvis down she had no way of knowing that, 20 years later, someone would want her song for one of the biggest motion pictures of the 1990s.
Taking a human decision generated so much more for Dolly Parton over the year – critically, musically, and financially – than the logical decision she could have taken in the mid-1970s.
As business moves go, Dolly Parton’s human decision was one of the best.
Andrea True
At some level, you are probably familiar with Taylor Swift and Dolly Parton – however superficially.
With Andrea True, that’s much less likely. Unless you’re of a certain age, in which case you’ll certainly remember her biggest hit record. But more on that in a moment.
Andrea True had a very musical mother, and had studied music herself, but wanted to become an actor, and moved to New York from her home in Nashville. Along the way she kept her singing career going in pubs and clubs as a way of helping make ends meet.
She didn’t get the results she hoped for in her acting career, but in the mid-1970s she was hired by a real estate business in Jamaica to feature in a series of TV commercials.
After shooting the commercials the Jamaican government had one of their periodic fallings-out with the US government and prevented people taking money out the country. Andrea True would have had to either forfeit her fee or spend the money in Jamaica before going back to New York.
Instead she took a smart, but very human, business decision.
Andrea True contacted a friend in the music industry who had an instrumental track he’d been working on and used the fee from her commercial work it up into a something more like a finished product with the help of some Jamaican musicians. That music could then, perfectly legally, leave the country.
Back in New York, she and her friend, Gregg Diamond, worked on the song and Andrea added her lyrics to the instrumental track. Along the way the song was turned into a disco anthem and the result was the 1976 UK and US Top Five hit “More, More, More”.
This piece of shimmering disco pop was a staple of the dance floors for a large part of the mid-to-late 1970s and quite rightly features in Billboard Magazine’s 2025 list of “100 Best Dance Songs of All Time” at Number 36.
If you’re not familiar with the song, don’t worry, I’ve got you covered – you’ll find a link to it below.
But before we get there, let’s just reflect on Andrea True’s very human decision that there was no way she was going to let the Jamaican government take the money she’d worked for. It took some “outside the box” thinking and a degree of grit and determination that all good ideas take to come to fruition.
Logically, it would have been easier for Andrea True to book herself into one of Jamaica’s nicest hotels and spend a couple of weeks in luxury, thanks to the fee she’d earned from her commercials, after she found out she couldn’t take her money out the country.
Instead, she used her human powers of decision making to turn the potential loss of all her money into a Gold record in the US and an international smash hit.
Well done to Andrea True – that was a great business move, and vastly better than just spending her money on a nice hotel break, thanks to her human, rather than logical, decision.
What does this mean?
There’s no real moral to these stories apart from the observation that a logical decision is often the easy path. Doing what people would expect, being able to express your decision in seemingly-objective terms, conforming to the norms are all the result of logical decisions.
Most of the time, being logical won’t make you broke.
But being logical also means you’ve likely given up a huge percentage of any potential upside.
It would have been logical for Taylor Swift to shrug her shoulders when her record company went against her, and just keep going with her career.
It would have been logical for Dolly Parton to let Elvis record her song and give up half her royalties.
It would have been logical for Andrea True to have a nice holiday in Jamaica instead of recording a global smash hit.
All of those decisions would have been entirely logical. Completely defensible.
And, at the same time, they would all have given up an upside beyond their wildest dreams.
While logic has a role, the sort of human decisions that only humans can make – often seemingly “illogical” at the time those decisions are made – are where all the upside in life is, inside or outside the music industry.
However these three women from the music industry have, between them, made some of the best business decisions of all time.
We could all learn a lot from them.
Music mentioned
In case you got this far and aren’t familiar with any of the songs referenced above, here they are:
Taylor Swift “Shake It Off (Taylor’s Version)”
Dolly Parton “Coat of Many Colours”