As he reveals in his autobiography, Some Fantastic Place,
it's certainly not been a case of entirely plain sailing en route to becoming one half of South London's celebrated songwriting duo with Glenn Tilbrook
behind chart act Squeeze.
He recalls that his awkward teenage years spent partly as a skinhead prone to finding himself in trouble did not suggest a future marked down for greatness.
But a valiant escape plan presented itself through his insatiable love of music, which he developed despite a school careers advisor mocking his early dreams of following in the footsteps of Pete Townsend.
As he enthuses, penning his book came easily, though he says its release amid Squeeze's 15th studio album slightly got in the way of a packed schedule
which now includes a round of UK solo acoustic book tour
dates. But it's a challenge he's welcomed and wouldn't have it any other way.
He says he set out to deliver an honest portrayal of his time with the band he formed chaotically in 1973 amid one of the most dynamic periods in British music.
There was clearly no shortage of local inspiration, with the likes of near neighbour David Bowie, who had radically reshaped the traditional pop landscape that opened seemingly infinite creative possibilities.
So when the newly formed Squeeze
recruited a certain effortlessly cool young keyboard player named Jools Holland,
the group soon clicked and began honing its act among the New Wave Scene.
"While I didn't manage to become quite as famous as Pete Townsend, we have had similar journeys in some ways, and my life"s been been better for the experience.
"I"d love to have been in the Who, but I've been in Squeeze instead," reflects Chris on his notable career that has included an Ivor Novello lifetime contribution to British music award along with Glenn, touring the world numerous times, and releasing several solo records for good measure.
His latest work, Pants
, based on the musical Fancy Pants written with Boo Hewerdine,
is out this month, which fans are likely to be treated to among material from across his career.
According to the songwriter, it was his fateful decision to place a 50p advert in a shop window seeking a guitarist for a band brazenly declaring the role came with gigs and a record contract (neither of which were true), which sparked his future musical partner's interest.
The pair, who hit it off after their famous meeting at The Three Tuns pub in Blackheath, have since been likened to the Lennon and McCartney of their generation for the strength of their lyrics and uncanny way with a memorable melody, have gone on to enjoy a rewarding career.
"I think Glenn and I both had spades of ambition, and as dreamers we went well together on our route to the hear and now.
"Overthinking life complicates its natural ability to be great, and for me that's not what I want. I love the unexpected, and together we are that."
As the group previously conceded, it took them a while to make their mark in the studio, with their début album reportedly heavily influenced by its producer, John Cale of the Velvet Underground. He had allegedly instructed them to re-write much of the material.
Consequently, the album failed to make the forty, but the band were offered a reprieve with their next foray into the studio, Cool For Cats – with its strutting title track becoming one of their most enduring hits.
The album spawned several other singles including Up The Junction, with its two lead singles proving to be their biggest chart hits, as both managed number two status), that set them on the road to recognition.
For Chris, perhaps the greatest thing he has taken from being in the band has been the life-long friendships that have been formed from it.
While their sharp-dressing keyboard ace Jools may have long since departed their ranks for solo projects and his own acclaimed TV show, it seems that he and Chris have a strong bond.
"I see Jools often, we write songs together and eat nice food once in a while. He is fun and inspiring to work with, and yes, the studio (in Maidstone, Kent) is always open to me if I wish to come along."
Fast-forward several decades from their inception, and touring recording their latest album, The Knowledge, has seen them re-enter the top thirty album charts, and remind fans of just what made them special the first time around.
By all accounts, Chris describes their recent US tour as "great fun" and a chance to re-connect with a fanbase that has remained decidedly loyal over time.
From their huge back catalogue of studio and live album recordings, you would imagine it must be pretty difficult for him to pick out a favourite song?
"There are so many, the most recent songs are very good from the last Squeeze album, 'Departure Lounge' is classic in every way and it feels like a corner is being turned musically."
Unlike many of his generation who's desire to make new music may have long since ebbed, it seems the lure of taking fresh material on the road has not lost its fascination.
As the 63 year-old explains, life is treating him pretty well in East Sussex, though there may now be a few more practical considerations to approaching a new tour compared to back in the 70s, yet it's no less rewarding.
"The roads are not as good as they once were, and the time it takes to get from A to B is ridiculous sometimes.
"But I love being on the road, thought it wasn't always the case. Today, I have a story to tell, and like a troubadour, I'm out on my horse most nights.
"I'm really looking forward to the tour, which is going to be fantastic with readings from my book and playing along with Boo Hewerdine, who is a great guy.
"It's just going to be a different kind of experience," he adds, explaining it's enjoyable to be able to see the whites of people's eyes, compared to some of the band's larger shows.
While life with his solo material and time with Squeeze has clearly dominated much of his time, it seems there are at least a few more moments to just stand back and take stock of a memorable career to date.
It's clear that grabbing the chance to spend time with the family between touring is something that he has highly prized, and has left him with plenty of positives that have inspired his music and writing.
"My wife supports me and so do my children – a day for me is leaning on a wall and looking at the sky thinking and dreaming of the future, and how to pay for the next brick in the wall. I love what I do and I love the people in my life who flow like salmon up stream with me."
Chris Difford plays the Ropetackle, Shoreham, on the 20th April 2018. CLICK HERE for more info.