When the opportunity presents itself, we should all put our money where it is most convenient.A record number of people left their jobs in 2015 for a variety of reasons. Many people quit their jobs because they are focusing on their mental health. Or maybe they realized how efficient they were working from home and the company insists that they return to work. Perhaps it was the opportunity to finally bet on their own.AdvertisementDennis Schrder did not quit his job but he completely bet on himself. This is a concept that we love to romanticize with other athletes as well as people in general. It's much easier said than done. Some cases can even be dangerous. Schrder is at the top of those who have placed a wrongly managed and misguided bet on themselves. He could overtake Victor Oladipo's crown, although that was only circumstantial.Oladipo was still playing for the Indiana Pacers in the early part of last season. He was offered a renewal, starting at $25 million annually. A four-year contract with a value of almost $113 million was all Indiana could offer. This is similar to the $4 million offered by the New York Knicks to Julius Randle this year. If he had entered free agency, Oladipo could have earned four years and $145million (just like Randle in the past year). Instead, Oladipo chose not to accept the money that was offered to him at that time.After the 2019-20 season, Oladipo, who had suffered a ruptured quad the previous season, was able to be offered the deal. He averaged uninspiring numbers. After being traded to the Houston Rockets in the James Harden trade, Oladipo declined a $45 million two-year extension from his new team. After playing four games for the Miami Heat, Oladipo was again moved to Houston Rockets. He then re-injured the quad and decided to have surgery. This could keep him out of action until November or even longer. Oladipo is now back with the Heat, apparently for the veteran minimum. Womp womp.Schrder's mismanagement is unique because his contractual woes have not been attributed to anything health-related. After having his best season yet, the 6-foot-3 combo guard almost won Sixth Man Of The Year in 2019-20. In the final year of his $70 million four-year extension, he was traded to the Los Angeles Lakers. He had previously signed the extension while playing for the Atlanta Hawks many years ago. He was reportedly feeling down and rejected a $84 million four-year contract with the Lakers. This contract was similar to the deals that Fred VanVleet, Malcolm Brogdon, and Lonzo Ball signed just days before. Schrder was reportedly looking at the $100-120million range.Perhaps after the Thunder season or a second consecutive Thunder-like Thunder season (but still under the Laker spotlight), Schrder might not have reached that range. But, perhaps $90 million would have been possible if he had four seasons. We will never know because Schrder didn't get the offe and also didn't perform well under the magnifying glass of purple and gold. Through 61 games, Schrder averaged 15.4 and 5.8 points per game. His shooting percentages were only 44/34/85 which was very close to his career averages. He played in 65 games in 2019-20, only two of which he started, and averaged 30.8 minutes per game. He averaged 18.9 points per game and 4.0 assists per contest while playing with Chris Paul and Shai Gilbert-Alexander. His 47/39/84 shooting totals were his highest career totals. In the playoffs, Schrder scored 14.3 points per game and 2.8 assists per game on 40/31/85 shooting in the Lakers' first round six-game series loss to Phoenix Suns.Eight days after free agency officially opened, most of the major players have signed. The money has dried and Schrder is being offered a one-year contract worth $5.9million. Schrder may have to accept this offer if he wants the NBA's best team to win this season.AdvertisementThis is the lesson: Don't be afraid to place your bets. If you can, do it. You just need to be able to either proceed with reason or accept the potential ramifications. It is not as bad as it sounds for Oladipo and Schrder, both of whom are extremely wealthy, and neither are over 30. It might be worth it for you because it is unlikely that you will turn down these types of figures!