For someone who first walked through the Aggborough doors in 2005, he knows the good times have been in short supply for at least a decade.
He doesn’t need reminding either that the shelf-life of your average Harriers manager doesn’t even allow for the dust to gather.
In the 18 months since before his appointment, five have come and gone.
Add in global pandemic into the equation and you begin to get an understanding as to why there’s a reluctance to talk up the club’s chances.
Penn at 34 may be one of the youngest managers in the three National League divisions, but the club’s desire to claw back some pride through one of their own has already gone a long way.
In the latest in our series of special summer features, he explained: “In the past two seasons the club has finished 15th and 11th.
“That’s not good enough really. It’s got to be better, so it’s now about finding a way to do it.
“We need to respect the National League North perhaps a bit more than we have done in the past few years.
“In terms of mentality, we need to recognise there is a difference between playing on our pitch at Aggborough and playing at, say for example, Blyth Spartans.
“I know the game, I know the area and I know the level. It’s about respecting it and finding ways to win games.
“You don’t have to tell me how much the fans here need a season they can really enjoy again - I may not have been here continually since I first signed 15 years ago, but trust me I know.
“The bottom line is that the National League North is tougher to get out of than the National League in my eyes.
“We need to try and find a way to push this club forward and hopefully give the fans a reason to keep coming back.”
Penn has been busy, with summer signings including the deadly Amari Morgan-Smith, hardworking Lewis Montrose and bringing back the experienced Keith Lowe.
They get down to work in two weeks time and Penn is grateful Covid-19 has not forced the board into a big decision.
“It’s massive to remain full-time,” he added.
“We may not have the budget of a full-time club as such, but what we can offer is an environment where players can thrive and an education as well.
“We’re standing at 14 players so far, and that’s a number I am quite happy with.
“It may be a case of quality over quantity, but I am pleased with the players we have managed to add and although we lost (top scorer) Ashley Chambers to Brackley we will be in a positive frame of mind.”
Harriers fans may want to hear their manager tell them a promotion place is achievable, but he is keeping his powder dry.
“As I said, the last few finishing positions haven’t been good enough, we know that,” he said.
“We need to be better - I’ll leave it at that! It’s always better to keep ambitions to yourself as a manager, but we want to improve and we want to put smiles back on faces.
“I don’t want a stamp on Russ Penn’s head with his promises - and I don’t want the team talk done in other dressing rooms either.
“But this is a club with a real history and I’m so proud to have the faith put in me to steer it forward.
“The owner, Richard Lane and CEO Neil Male have been fantastic. They are determined to make the club better. Also my assistant Jimmy O Connor needs a mention. They are all a massive part of what we are building.”
It needs stability in the dug-out, as well.
The turn-over of managers was addressed by the board when Penn was offered the job full-time before the coronavirus struck.
He joked: “I hope I’ll last a little bit longer than some of the others!
“The club have come out and said they need that consistency and stability. I’m a local lad and I want to be here for three, four or five years.
“I started planning for this in my 20s and I now hold my A-Licence. I may be young but I have had this first job as a manager in my thoughts for a very long time.
“It’s something I have been working towards for years. I knew I wanted to be a manager ten years ago and I have been putting in place what is needed ever since.”
Does he take heart from unexpected champions King’s Lynn, and the unfancied other recent promotion winners like Altrincham and Chorley?
“Absolutely,” he said. “Sometimes not being tipped can really work in your favour. You never want to add pressure.
“It’s such a demanding division. The numbers of big clubs and the number of other sides not shy about spending money is scary - there are so many established clubs at this level now. It’s what the Conference was ten years ago.
“But I am very enthusiastic. It’s what has kept me going for the past five months!
“This is a wonderful challenge and I will give it everything I have got, make no mistake about that.”