It was a decision Tom Naylor seriously contemplated – without even knowing what the next step was.
As a dispirited teenager in Mansfield's academy, the midfielder weighed up hanging up his boots.
Despite regularly training with the first team, Naylor couldn't see a light at the end of the tunnel.
As his youth team-mates were consistently being handed their first professional contracts at the Stags, the Sutton-in-Ashfield ace thought being released at the end of his scholarship was an inevitable conclusion.
He was that serious about quitting he spoke to his family about life away from football before the anticipated bad news would arrive.
Days later, though, Naylor was finally offered pro terms – a two-year deal rather than 12 months like those who'd proceeded him.
And his willingness to accept the contract proved to be the best decision of the 28-year-old’s life.
Arriving from Burton last summer, Naylor heads into Pompey's renewed League One play-off push as an indispensable member of Kenny Jackett's squad.
He made 53 outings as the Blues suffered play-off semi-final defeat to Sunderland last term, while he was crowned the Players’ Player of the Season.
Yet if he'd have quit football, there might be one more name in Nottinghamshire’s Yellow Pages.
Naylor said: ‘Mansfield was my first professional club and I was going to leave at one point.
‘I knew I was doing well in the youth team because I was training with the first team quite a lot.
‘A lot of the youth boys weren’t but they were getting professional contracts anyway.
‘I was thinking “This is a bit weird, why are they getting deals before me?” They were all getting one-year contracts.
‘I was really close to leaving. Everyone was getting contracts and I thought they obviously weren’t going to offer me one.
‘Despite doing well, there wasn’t much more I could have been doing.
‘I spoke to my family and told them I was thinking about packing it in altogether
‘Eventually the gaffer did pull me in a few days later and told me he wanted to give me a two-year deal.
‘That got my confidence up and perked me up. I dug in and worked hard to try to get into the first team.
‘I then went on loan a few times before breaking through.
‘I wouldn’t have had a clue what I’d have done if I’d have left.
‘It was the best decision I have ever made not sacking football off because I wouldn’t have had a clue what to do.
‘Maybe I’d have ended up getting a trade or something. That would have been the easiest thing to do but I’m buzzing I didn’t.
‘All the lads who got deals before me aren’t playing anymore. They’ve just got normal jobs, really.’
Like a host of his Fratton Park team-mates, Naylor has climbed out of non-league and up the Football League pyramid.
Before making his breakthrough at Mansfield when they were in the Conference, he gained crucial experience on loan at Belper Town and Alfreton Town.
He’d win a switch to Derby in January 2012, but struggled to make a real impact.
It was at Burton where Naylor really showcased his talent, helping propel the Pirelli Stadium side from League Two into the Championship.
A return to the second tier is what he aspires towards with Pompey – but he hasn't forgotten his grounding in the unpaid ranks.
Naylor added: ‘It’s hard when you’re young. Sometimes you’ve got to start lower down and work your way up the ladder. That’s what I did.
‘Some people start high and aren’t in the game anymore. It’s a hard world out there.
‘As a youngster, I went on trial at Derby and Forest but I didn’t think I was quite good enough at the time.
‘I got picked up by Mansfield when I was about 15 just playing on a Saturday morning.
‘From there, I went into the youth team then broke through when they were in the Conference and the only way has been up from there.
‘I made my debut at 17 and eventually I made it into the Championship. I’m 28 now so it’s been 11 years in the pro game.
‘Working your way up is the best way to do it for me.’