In the book I Am That, a compilation of his talks, he spoke about the road being the goal and to “enjoy its beauty and its wisdom”. The thinking is that always being on the road allows life to become natural and simple.
Try telling that to those Rangers fans who traipsed out of Forthbank Stadium on October 6, 2012, beaten 1-0 by a Stirling Albion side whose manager wasn't even present due to his own wedding.
From that day it would be nearly nine long years before the Ibrox club were at the top of Scottish football once more.
The fall. The controversy. The disillusionment. The comeback. The success. The elation.
The road back, or “the journey” as Rangers fans like to call it, was arduous – and at times downright embarrassing.
But when the Scottish Premiership was wrapped up last season with many games to spare, and an invincible league campaign achieved, those defeats to Stirling, Annan and Peterheard made the success that little bit sweeter.
At every moment along the way, however, the goal was the Scottish Premiership.
For many, whether it be individuals or teams, a moment like that league victory for Rangers would, once celebrations quietened and passed, prompt relief and perhaps complacency. A time to breathe.
That can’t be the case at Ibrox.
Trophies are the goal
Such is the nature of the club, the demands, once one goal is achieved the next one is on the horizon. There is always something tangible to be aimed for. The road is a means to an end.
Now, the goal, as it is every season at Rangers – and Celtic – is to win the league again. And again. And again.
Looking further ahead, there is a chance to put some real distance between them and their floundering city rivals who resemble the most dysfunctional of Wacky Races teams. They’ve fallen off cliffs, they've been stuck in trees and they’ve been cut in half by Rufus Ruffcut and Sawtooth.
That in no way takes away from Rangers’ success. While Celtic have been regressing, the Ibrox side have been progressing, on and off the field, under the astute management of Steven Gerrard and his backroom staff.
Stronger than last season
That can be witnessed in this summer’s recruitment.
So far they have picked up two players in Fashion Sakala and John Lundstram on free contracts who would, if contracted, cost well more than £10million combined. They have added more pace, power and strength to the squad.
Just as important, they have not yet lost any key players.
There is no longer a need for overhauls. It's about continuity, quality over quantity, plus it would take many millions to bring in upgrades on the likes of Connor Goldson, Borna Barisic, Ryan Kent.
Last season’s 25-point gap between Rangers and Celtic looks more likely to increase, rather than decrease – simply in the case that one side has got stronger and the other weaker.
The depth across the pitch for Rangers, especially in the centre of midfield – Glen Kamara, Ryan Jack, Steven Davis, Lundstram, Joe Aribo, Scott Arfield, Stephen Kelly, Ianis Hagi and, when fit, Nnamdi Ofoborh – and attack is staggering.
It’s reached a point where if Rangers were a box of celebrations, the manager could stick his hand in and know he is likely to pull out a Malteser, a Galaxy or a Galaxy Caramel, while knowing the chances of getting a Bounty are slim to none.
The squad building over recent transfer windows has presented a side which is now capable of evolving from Gerrard’s take on the 4-3-3. That remains the default setting, the trusted system which the players could run through the movements and positional play in their sleep.
But, as if playing Football Manager, the Rangers boss could go to the formation drop down menu and be presented with more options.
The rise of Nathan Patterson provides the chance to go with three at the back. A front pairing in attack, as was trialled last season, gives the team a different attacking dimension. Then the midfield options offer up so many solutions, whether in a single or double pivot.
It has reached the point where it's not a case if Rangers win the league, it’s how they win it.
Their biggest enemies will likely be themselves and perhaps involvement in the Champions League.
Being the champions means being the team which is being hunted, the ones with a target on their back. This is different to this squad and requires a mentality shift, starting on Saturday when they welcome Livingston to Ibrox for the start of the 2021/22 cinch Premiership campaign.
Even the very best get complacent. Manchester City found it hard to win back-to-back titles in the Premier League, then there was Liverpool. After such a long wait for a league title they struggled coming back for more.
While it is easy for external forces to say Rangers will walk the league, the last thing the players can do is allow themselves to think that.
The return of fans adds another dimension. There will be an expectation to not only win but do so handsomely, especially at Ibrox. That in itself brings increasing pressure.
Gerrard said: "We have to embrace the pressure of being Champions from last season, but we have to remain humble and keep the hunger we have had over the last 12 months.
"The evidence from training shows me the players are ready to go again.”
You can only go on what is delivered on the park but first-team coach Michael Beale is constantly looking to evolve, Ross Wilson’s comments about what attributes the team required more of is encouraging for supporters then there is Gerrard.
The Liverpool legend is the type of character who strives for more. Someone who knows the road is there to be travelled to get to the actual goal, winning football games and bringing more titles to Ibrox.