But the 31-year-old admits even he has known nothing like the past week as own goals, conducting contract talks with two clubs himself and a truly surreal meeting with Leeds United chairman Ken Bates combined to make it one he will not forget in a hurry.
In the end, everything worked out well with O'Brien's future now sorted after agreement was reached over a two-and-a-half year deal at Elland Road and his new club extended their unbeaten run to 12 games courtesy of a dramatic stoppage-time equaliser by Luciano Becchio against Middlesbrough.
For a time, however, the former Bradford City defender admits the stress and worry of deciding whether to join Leeds or promotion rivals Cardiff City was keeping him awake at night.
O'Brien, who made one appearance in a friendly for England Under-21s before opting to play for the Republic, said: "It has been quite a week, starting with those own goals against Portsmouth, and I haven't slept much. I don't have an agent so I did all the dealings myself.
"I prefer to do it that way as sometimes when a third party gets involved then things can get lost in translation. It did mean I spoke to Ken Bates on my own and did the negotiations with him.
"The meeting with the chairman was something I will remember all my life. It was a bit like when I signed my first contract at Bradford with (then City chairman) Geoffrey Richmond – that was entertaining as well.
"My Dad came in with me initially and he is a big bloke of around 20 stone. The chairman's first words were, "We'll sign the fat one instead." My Dad replied he had been on a diet for six weeks, to which the chairman said, 'Well that isn't effing working, is it?'
"Dad is quite quick-witted and said back, 'Well I don't know what your excuse is'. It went from there but the great thing is I lived to tell the tale.
"I also had an offer to go to Cardiff and went down there to speak to Dave Jones. I got the impression Cardiff liked that I had the guts to do everything myself without an agent.
"What I wanted to do was be up front all the way through and not mess about behind anyone's back. I like to think I did that.
"Cardiff came in with an offer and the first thing I did was ring Leeds and tell them exactly what the deal was. There was a bit of toing and froing and then I said, 'If you offer me what Cardiff have offered then I will sign'. That is what happened.
"It is a relief to have sorted things out. Two months ago, I was scratching my head as to where my future would lie. Now, I am just glad that I know where I am going to be for the next two-and-a-half years.
"There was an agreement to keep me here (on loan from Bolton) until the end of the season but I wanted security. It would have been a risk, as if I got an injury then I would have had nothing come the season's end. So, it is great that everything is now sorted."
The news of United having reached agreement with O'Brien was relayed to the 30,452 crowd shortly before kick-off and greeted with a rapturous ovation.
For the United fans, it was the last thing they had to cheer for the best part of two hours as their side turned in a flat performance that, but for Becchio's late strike, would have handed Middlesbrough all three points.
Misplaced passes, poor decision making and an over-reliance on pumping long balls forward that were easily dealt with by the hugely impressive defensive pairing of David Wheater and Matthew Bates meant chances were at a premium for Leeds until the closing stages.
By then, Boro were ahead thanks to Wheater's second goal in as many games, the defender deftly flicking Julio Arca's corner past two defenders on the line and into the net.
Just 20 minutes had elapsed but it took until the closing stages for United to build up any kind of momentum as, first, Sanchez Watt headed wide and then Ross McCormack shot just past a post.
Watt compounded his earlier miss by shooting straight at goalkeeper Jason Steele in the 89th minute before Boro were punished for an amazing miss by Justin Hoyte with Becchio finishing from eight yards out.
There was still time for McCormack to somehow head wide after being found unmarked inside the six-yard box, though it has to be said a winner then would have been desperately cruel on a Boro side whose only crime was that they handed the initiative to their hosts by retreating deeper and deeper in the closing stages.
Scott McDonald, who flew out last night to join up with the Australia squad ahead of the Asia Cup getting underway, said "We played really well but just couldn't keep them out. A lot of people were hanging their heads in the dressing-room because it almost felt like a loss."