With the S&P 500 and the S&P/ASX 200 racing ahead approximately 27% and 10% in 2021, it's fair to say investors have had a surprisingly good year. Despite the ups and downs of COVID-19 (of which we are still suffering through now), lockdowns, and border closures, if investors were fully invested, they would have walked away with truly impressive returns over the past 12 months. 

That said, there are always some positions that hurt more than others, which cause both headache and heartache as we watch their share prices fall lower and lower. 

And while it's easier said than done to cut your losses, as revealed in this video, it can sometimes pay to stay convicted in a poorly performing position. 

As part of our annual Outlook Series, we took it to nine of Australia's most respected fund managers to share their worst trade of 2021. From companies that saw their share prices halve during the year, to calamity over a capital raising, an IPO gone wrong and an opportunity forgone, our Sydney-based fundies candidly reveal the painful positions (or lack thereof) that kept them up at night during the 12 months just past. 

Plus, they share the lessons they took away from these headaches so you can better invest in 2022.   

Our featured experts include:

Simon Shields, Monash Investors 

Eleanor Swanson, Firetrail Investments 

Steve Johnson, Forager Funds 

David Moberley, Paradice Investment Management 

Hamish Carlisle, Merlon Capital Partners

Chris Demasi, Montaka Global Investments 

Bob Desmond, Claremont Global 

Anthony Aboud, Perpetual Asset Management 

Matthew Kidman, Centennial Asset Management