There are obvious parallels with Lessing 12 years ago and Alistair Brownlee now.
“The Olympics weren’t a great experience for me,” he tells BBC Sport. “I didn’t enjoy it and I just wanted to get out of there.”
Lessing is referring to Sydney 2000 when, as the world’s number one triathlete, he was widely expected to win gold for Great Britain.
He finished ninth, years of dominance in the sport were forgotten in an instant and he returned home to be met by his postman demanding £10 back for a failed bet.
Twelve years on and four years into retirement, Lessing can afford to laugh at how he even made the pages of GQ. “They listed the top 10 failures of the year and I was at number nine,” he chuckles.
For those not familiar with the world of swim, bike and run, Lessing is an icon. Winner of four world and three European titles, plus an Ironman champion to boot, he was named the greatest triathlete of all time by 220 Triathlon magazine. And if you need further proof of his impact on the sport, consider how many triathletes have been made an MBE.
Read more: News.bbc.co.uk