Being able to share success with family members makes it all the more rewarding, and that was the case fourteen and a half years ago for brothers David and Neil Gregory, when they made Football League history.
In front of nearly 20,000 people at Wembley Stadium, the duo both pulled on the blue and white of Colchester United to become the first set of brothers to play alongside each other for the same team in a Play-Off Final.
"Once the game starts, you forget that your brother's out there," David reminisces.
"There were plenty of times where we knew what each other was going to do. He would get treated the same as any other player, though. I'd shout at him just as much as anyone else if I thought he'd made a mistake.
"We always walked out together, even if I was captain, he didn't let the keeper come out second - he would. And that didn't change for the Play-Off Final but one thing that did surprise us was the fireworks going off as we walked out."
After the fireworks had died down, it turned out to be a good evening under the lights of the national stadium. David played the full 90 minutes, Neil got 70, and the U's won promotion for the first time in 22 years by beating Torquay United 1-0.
And who got the only goal of the game? David, of course - from the penalty spot.
"When the ball went in, there was no thought about scoring the winning goal at Wembley as there was too long left to play for that," David added, "It's only afterwards that it takes on any meaning.
"I should have had the chance to score again in the second half but the referee missed a blatant foul on me by Paul Gibbs, who had left us for Torquay the previous summer."
Colchester had the ideal preparation for the Final against the Gulls; they had appeared at Wembley the year before in The Football League Trophy.
They lost that day, against Carlisle United on penalties, but it helped shape the future, in David's opinion.
"That was a day out and everyone was a bit in awe of the place [at The Football League Trophy Final]. For the Play-Off Final, we knew exactly what to expect and I know that helped us," he added.
"It was an amazing time leading up to the big day, as well as afterwards with our family. Our parents were there and they met us for a drink before we went on to the club function in London in the evening."
David's Play-Off appearance at Wembley came in a career spanning just shy of 20 years, which took him from Ipswich Town, to short spells with Hereford United and Peterborough United, followed by Colchester, before ending up with Canvey Island in the non-league circle, once again playing alongside his brother Neil.
It was a rapid introduction to football for the now 42-year-old, though.
"It all happened pretty quick for me. I only came into the football environment when I was 16 and within a week of starting pre-season training with the youth team at Ipswich, I was training with the pros and played some pre-season games for the reserves.
"The first real highlight was being offered a pro-contact a month after my 17th birthday. My full debut for the first-team was another great occasion - I scored a first half hat-trick against Watford.
"Being at Ipswich when we got promoted into the inaugural Premier League in 1992 was a good time to be at the club and playing and scoring in the top league obviously counts as one of the highlights of my career.
"The only downside to my time at Ipswich was not playing as many games as I would have liked, and never getting the chance to play in the same Ipswich first team as my brother Neil, but that obviously came at Colchester.
"Neil was on Ipswich's books far earlier than I was so I always thought he would make it in the game."
Three years the elder David surprisingly reveals that when it came to football there wasn't much competition between the brothers, that was reserved for life away from the pitch and whenever they played other sports together.
"Whether it was tennis, golf or snooker - we both desperately wanted to win every time," he said.
"I'm sure our sister Catherine used to hate us when we were kids, especially with our parents having to take one or the other of us to play football every weekend. She was as proud as our parents that day at Wembley, though."
The two made history in football back in 1998 on that Friday evening, and the game still has them both.
Neil has coached and managed since hanging up his boots, and he is the current manager of Stowupland in Suffolk.
David, meanwhile is back pulling the strings at the Essex club. Not on the field, though. His duties lie in the media department, as the club's communications and public relations officer.
"I often did the co-commentary for BBC Essex when I was injured and when I left, I did a page for the matchday programme for a season.
"I was fortunate to get my job and have really enjoyed learning a whole new side to football, while at the club I had a lot of great times at as a player."