Five is one of the most powerful members of The Umbrella Academy, he often misses the mark when it comes to traveling through time. It's easy to overlook, but Five's lack of control and accuracy is one of the pivotal features of the plot in seasons 1 and 2. So why is he so bad at using his abilities?
The Umbrella Academy is littered with the unreliable results of Five's time travel, often kicking off conflicts that drive the series. The first time Five tried a major jump in time he overshot, becoming trapped in a post-apocalyptic future before making his way back home. When Five did manage to return to his "present," he accidentally deaged himself, turning from a 58-year-old man into a 13-year-old boy. Later, in season 2, Five again tried to travel in time, in this instance with his six siblings in tow. But with more stressful circumstances, a bigger jump and more people to carry, it's no wonder Five got it wrong again, scattering the other members of The Umbrella Academy throughout the 1960s.
Five begins to gain control over his powers toward the end of season 2, succeeding in a smaller time jump of only a few seconds, rather than failing in a jump of days, weeks or years. Some of Five's newfound control can be attributed to an increase in practice. Since Five's first unsuccessful time jump in season 1, he's had decades to learn more about time travel (with the help of the Commission) and practice dozens of time jumps in a variety of circumstances. Five's newfound control is also triggered by a tip from Reginald Hargreeves, proving that some of Five's problems stemmed from a lack of support and coaching from Hargreeves (who forbade him from practicing time travel in the original timeline).
Five displays a rebellious attitude from the beginning of The Umbrella Academy, perhaps explaining why he's ranked fifth among his siblings despite the scope of his ability. Although Five is powerful, he's unwilling to blindly obey Hargreeves, like Luther does. Five is also not easy to manipulate or control, like Diego. Therefore, he falls to the bottom of Hargreeves' list when it comes to training. Five and Hargreeves are both aware that Five is capable of more, but Hargreeves refuses to share knowledge or theories with him, setting back Five's ability to control his power. When Hargreeves shares just a hint about the deeper nature of Five's power with the boy in season 2, Five becomes immeasurably more adept.
Five's arrogance at the beginning of season 1 also explains why he may have so little control over his ability to time travel. Five believes himself capable of anything, so he's unwilling to admit there are any areas in which he needs work. Five's mistake in traveling to a post-apocalyptic world in season 1 and additional error when traveling back humbles him, making him more willing to think about where his power might go wrong and how he can fix it. Five hones his power at the end of season 1, safely transporting his siblings back in time, though off-target. Finally, at the end of season 2, after much practice and thought, Five effectively uses his ability to save his siblings from the Handler.
With that success, Five displays a dexterity with time travel that is similar to the ease with which he travels through space. That bodes well for the other members of The Umbrella Academy as they face new threats in the form of other super-powered people. By the end of season 2, instead of examining the disasters wrought by failed time travel, the series has shifted to focus on the unexpected consequences of successful time travel. Five succeeds in transporting himself and his siblings back to 2019, only to discover that they've created an alternate timeline in which Reginald Hargreeves is alive and running the Sparrow Academy.
