The switch from government to the cut and thrust of commerce is not an easy one to make, as David Cameron has discovered to his great cost.
The former Prime Minister has gone from being the face of luxury garden sheds to the pin-up star of the biggest meltdown in global finance as an adviser to the bust lending shop Greensill.
It hasn’t exactly gone smoothly for Philip Hammond either. Spreadsheet Phil was rebuked by an independent watchdog earlier this month for using his government links to help Oaknorth, the start-up bank where he is a non-executive director, on a project it was involved with.
And the less said about Nick Clegg’s stint at Facebook the better. Does anyone really think that a man who struggled to leave his mark on UK politics will be able to temper what is expected to be the most aggressive regulatory assault against the tech industry in its history under Joe Biden?
Still, nothing will ever top the reinvention of Tony Blair, who has gone from toppling dictators to advising them, earning a fortune in the process.
So what are the chances of George “nine jobs” Osborne making a seamless transition from shameless portfolio career to City dealmaker extraordinaire at secretive Mayfair advisory firm Robey Warshaw?
The former chancellor swapped a string of high-profile roles, including a £650,000 salary for working four days a week at investment giant Blackrock, to join the firm in April.
Well, after a slow start, Osborne has been credited with bringing in his first piece of business, and what a mandate it is for a firm that prides itself on discretion: advising EN+, a company set up by Oleg Deripaska, a Russian oligarch with links to Vladimir Putin, and someone who once hosted the former chancellor on his yacht, to boot.
Not only that but this is an organisation that has previously been sanctioned by American authorities for its close ties to the Kremlin, and whose billionaire founder is the subject of a US travel ban.
Reports suggest that Osborne landed the role because of his relationship with Greg Barker, EN+ chairman, and the man who brokered the lifting of sanctions in return for Deripaska standing back from the company in 2019, though he still retains control with a near 45pc stake.
But Osborne also knows Deripaska, having been a guest on his yacht in 2008 under controversial circumstances. The then shadow chancellor was accused by financier and former school friend Nat Rothschild, who had also been aboard, of trying to solicit a donation.
Osborne denied the claims, saying they drank tea while discussing British and Russian politics, education and Russian history.
Still, there is at least an undeniable theme to his private sector work – Osborne’s other dilettante career as a newspaper editor was largely thanks to the help of another Russian sponsor in Evening Standard proprietor Baron Evgeny Lebedev of Hampton and Siberia.
You can see why Osborne was keen to join Robey Warshaw. After all, this is a firm that has raked in just north of £200m in fees since setting up in 2013, a sum that has largely been shared between its three partners Simon Robey, Simon Warshaw, and Philip Apostolides, all former investment bankers.