But it's even worse on a public stage – and when the guy in charge has an estimated net worth of more than $5 billion and is one of the most famous people in your country.
That was the ugly predicament facingthe Luna Rossa sailors, less than two weeks ago.
As the Challenger of Record and longest-running syndicate, they were meant to be strong contenders in Auckland, but struggled in the round robin series.
They lost all three races with INEOS Team UK and were trailing American Magic before Patriot's capsize. Their only other win came when the Americans failed to complete the course in fluky conditions.
It meant the Italians were consigned to the elimination semi-final, and seemingly not in good shape.
"[It was] not the greatest moment for the team," Luna Rossa co-helmsman Francesco Bruni told the Herald. "We knew we had to react, in every area."
Grinder Nicholas Brezzi was in his first Cup campaign but could feel the tension.
"It was quite tough," said Brezzi. "We [made] a great effort as a team to stay united and look at the positive aspects. [But] of course we did mistakes, we had to admit it."
So what was the message from team supremo Patrizio Bertelli, the Prada chief executive who founded the syndicate in the late 1990s?
"I think he is the best boss because he didn't send any message," said Bruni. "The best message was his silence. Sometimes it is better not to say anything…you feel more what he wants to say to us."
"Mr Bertelli is always pushing us to the limit, always giving us confidence," added Brezzi. "It's quite an honour, but the main thing you can see is he really has passion for the team and for sailing."
From considerable despair, the Italian renaissance started less than a day after their narrow loss to the British team in the final round robin race.
Inside their base on Hobson Wharf, there was a series of meetings, with some brutally frank discussions.
"It was important to analyse every detail," recalled Bruni. "Another message was that there should be no critics from one department to another. We all have to row in the same direction."
Though Bruni and Spithill put on a brave face publicly, the losses to the British stung, given they had been in strong positions in at least two races and it was a significant reversal from December's World Series.
"We discussed every single mistake we did racing against the British – there were a few – and there were a few things we could have done better," said Bruni. "I'm sure in every department there was the same criticism. We win as a team and we lose as a team."
The afterguard of Bruni, Jimmy Spithill and Pietro Sibello had detailed sessions with their coaches Phillippe Presti and Jacopo Plazzi, examining how they could improve individually and as a trio.
"[The relationship] has always been very good," said Bruni. "I like that when we lose there is no finger pointing. It's great; working with Jimmy, Pietro, with the whole sailing team."
Spithill is no stranger to difficult Cup situations – with many sweet and sour experiences over two decades – and saw their predicament as a blessing in disguise.
"It was a challenge," Spithill told the Herald. "That is why you are here. That's the great thing about sport. You are exposed, whether you win, lose, make good decisions or make bad decisions. For me it was a bit of curiosity to see as a group, how we would react to that."
At the same time, the shore crew was working relentlessly to improve the boat, modifying the existing set up and introducing some new hardware.
The end product was a spectacular transformation. In the semi final Luna Rossa was noticeably quicker and last Friday they buried the belief that the boat was only suited to light breezes. And the crew work was sharp and focussed – near flawless – as they swept the Americans 4-0.
A much greater challenge awaits, but the Italians take comfort from where they have been.
"We knew we had a long way to go and knew we could be doing things a lot better," reflected Spithill. "But we have got the culture there now. We got stronger, we got faster and there is a lot more to go. We want more and we need to get better. We are in for one hell of a fight."
Heading into the Cup racing?
• Give yourself plenty of time and think about catching a ferry, train or bus to watch the Cup.
• Make sure your AT HOP card is in your pocket. It's the best way to ride.
• Don't forget to scan QR codes with the NZ COVID Tracer app when on public transport and entering the America's Cup Village.