Since being Rookie contracted in 2012 via the Cricket Superstar television program, he has been delisted, had a record-breaking couple of years in Victorian Premier Cricket, was re-contracted, made his first-class debut, was delisted again, before now earning a three-year contract in the UK with County side Hampshire.
His story is anything but traditional, but the Ringwood product credits his ability to look beyond cricket, and into his life after, for keeping him focused on what is important and how his life is going to look once his professional career ends.
"Initially, it didn't happen for me straight away as an 18, 19-year-old, which was probably a blessing in disguise in terms of overall life balance and what I wanted to do after cricket," Holland said.
"At that stage I just went to University and I completed two years out of three in Exercise Science and after I got a Rookie contract, I did the final units part time.
"There was then a four or five-year period where I was on-contract as a Rookie, then off-contract, then back on-contract with Victoria. That was probably five years that I didn't quite feel settled with cricket.
"I know a lot of people never feel settled within their career, which is just the nature of the beast."
After completing his degree, Holland then pursued two ACA Beyond the Boundary placements in sports science before realising that he still wanted to be on the other side of the 'sporting fence.'
"It was good to understand that it is not what I want to do at this stage of my life," he said.
"I then thought about teaching, and started studying that part-time, which I think was probably a more of a safety net than anything; then with me going over to England with the intense schedule and the time difference, I didn't have the time to do the study via correspondence.
"So, then I thought: what are my other interests?"
Holland returned this summer with a full County season under his belt, and is relishing not having to 'fight' for a contract in Victoria, with his UK future secured for the time being. This has allowed him to explore other paths, to keep searching for the career that will take him beyond cricket.
"As I have two more years at Hampshire, being back in Melbourne presents a nice little opportunity to dip my toes into a few things," Holland said.
"Recently, I have been lucky enough to have an opportunity with a friend's business doing a mentor internship, which has given me a taste of how the business world works.
"I have also been interested in the stock market over the last few years, and after chatting to [ACA Transition Manager] Carla Dziwoki a few weeks back, she made it clear that I still had access to the Education Grants current players receive.
"So, the ACA were able to pay for a short course in stock trading.
"I am also involved in a mental health program called 'Outside the Locker Room' with [former Richmond Tiger] Jake Edwards, so doing things that are a bit more meaningful with my time as well has been one of the priorities for me while I am back in Melbourne."
Dziwoki, who facilitates the ACA Transition program, says that Holland is a fantastic example of a player who understood that players have to plan for life after cricket, even if they aren't sure of exactly what they want to do.
"Ian has tried a number of educational and extra-curricular interests whilst on contract; which we encourage, and despite not being completely committed to a long-term career goal.
"He has used all the resources available to him through the ACA, like Education Grants and Placements, to explore areas outside of cricket that were of interest, to help him make informed decisions around what he might want to pursue when his sporting career comes to end.
"The reality is players careers can be limited, so it is important athletes continue to develop their skills away from the game, which Ian has done exceptionally well."
Holland's advice for players young and old is clear.
"You have to be real with yourself: if you're lucky you will play until you are 30, then after that you have to walk into another career.
"So, having a look at the big picture, you would be naïve not to take advantage of the network and opportunities you have within the cricket family.
"I feel so fortunate to have the resources of the ACA, which has opened up a lot of doors down different avenues.
"I think if you are on contract you would be silly not to use those, because let's be honest, cricket careers rarely last as long as you would like them to."