As someone who has known nothing else but the beautiful game since leaving school at 15, it has been a strange sensation being out of work since the summer.
An initial period of rest and then contemplation after such an unbroken stint in football – especially given a tumultuous first half of 2018 initially with Barnsley and then Leeds United – may not have necessarily been too bad a thing.
But after some quality time with the family and attempting to lower his golf handicap, among other things, the 41-year-old – still young in managerial terms – has been refreshing the skills set required for the ever-evolving world of football management in preparation for his next challenge.
Days have been structured like working ones, countless games taken in and the opinions of various luminaries, whether they be in football, psychology or business, have been canvassed.
After rebuffing offers to return to management he now feels truly ready.
Heckingbottom, who left Leeds at the start of June, told The Yorkshire Post: “It was a great summer in terms of the weather and the kids were off and I enjoyed all that.
“But I also had things I wanted to do and it felt like I was still working too. I was getting up to tick a list off and thought, ‘I need to do this and that’.
“Then about a month ago, I started to think, ‘what am I doing?’ It hit me that I was not in work for the first time ever. It crept up without me realising.
“So I have got even busier and I am trying even harder and out even more. I have an ambassador role with the LMA (League Managers’ Association) and I am doing bits and pieces and charity work with them.
“I have now got itchy feet, big time. But I know I was right not to jump straight back in. I made that commitment to get better at certain things and I have done. But it is still difficult when you are watching at games all the time.
“I have been down to various clubs when I can and studied games – things which I know I needed to do. I downloaded 10 games of (Maurizio) Sarri playing 4-3-3 for Napoli for instance and looked at his differences compared to (Pep) Guardiola. It is just daft little things.
“I have spoken to everyone; managers who are not working and ones who are now. It was good going up to see Rafa Benitez at Newcastle for example and we spoke a lot about the politics of football and things like that and there were certain parallels between Newcastle and me at Barnsley.
“But now it is time to get back to work.
“Even when I go and play golf I am still on the phone on the golf course and I am always thinking about it (management).”
Being sacked just four months into his 18-month contract at Elland Road, allied to some stressful experiences towards the end of his spell in charge at hometown club Barnsley, might have put many off a return to the managerial ‘madhouse’, but Heckingbottom is made of sterner stuff and highly driven.
His experiences – good and bad – in what has effectively amounted to a two-and-a-half-year crash-course have seen him witness every facet of life as a manager.
It has provided him with invaluable lessons for future challenges ahead and a steeliness to succeed.
While his time at Leeds was short he is adamant that those experiences will make him a better manager in the long run.
Heckingbottom, who also has a Masters degree in Sports Coaching, said: “Leeds was a big job and a big club and I loved it. There were lots of things we needed to do and change behind the scenes and lots of big, tough decisions needed to be made.
“But Barnsley was a lot more all-consuming as you felt you were on your own a lot of the time.
“In the couple of years I was there I took on a lot of roles and responsibilities and was driving to get things done. At Leeds there were lots of staff there and decision makers and it was totally different. The value of both experiences have been really good, definitely.
“Leeds wanted a head coach, but I just felt that the decision-making around the first team had to change and the atmosphere, make-up, recruitment strategy and staffing, and they have done it.
“I took a lot of positives from Leeds when I look back. But the disappointing thing was that they came and got me because they wanted X, Y and Z and spelt it out and said, ‘This has got to happen’. But within a couple of weeks it was not happening.
“I took people on and had arguments over it and tried to make changes and did. It maybe quickened my exit a little bit. But the worst thing I could have done was sit tight knowing it is going to fail 10 months down the line and then get the boot.”
While quickly appreciating that time was likely to be called on his Elland Road reign at an early juncture in the close season, Heckingbottom’s move from hometown club Barnsley was rather more dramatic.
Thankfully water has gone under the bridge since he controversially headed to Leeds at the start of February shortly after details of his new contract were announced by the Reds.
The Oakwell outfit expressed their shock and disappointment in a club statement with Heckingbottom’s move triggering much anger among fans who had previously adored him.
Aspects regarding how his departure was handled plainly did not sit well with him at the time. But he has quickly “moved on” and returned to Oakwell as a Sky TV pundit for the recent home game with Luton Town.
Looking back to events earlier this year Heckingbottom said: “The club, to protect their own back, fuelled it a little bit, which I did not like.
“I do not think there was any need for it, but understand why they did it.
“It was nice to go back (for the Luton game). I will always go back; I was in the Legends Lounge for a few hours after and was seeing everyone and it was great and I enjoyed it.”
So to the future with the sight of Heckingbottom watching his former club intently while on media duties a fortnight ago being a reminder of what he misses and craves – a return to the managerial frontline.
“There is lots wrong with management in how crazy it is. It can be an impossible job, but it is a drive,” he observed.
“I have had a taste of it and three good years at it and have learned a lot and that all-consuming challenge is what I miss. Until that changes I will keep doing it.”