Most guys quit growing their hair out at exactly the wrong moment. They hit the eight-to-twelve week mark, nothing is fitting right, it's too long to sit cleanly and too short to do anything with, and they sit back down in the chair and ask for it all to come off. It feels like a decision. It's actually just the most predictable phase of the process, and knowing it's coming is the only thing that makes it survivable.
The first month is usually fine. The cut still has its shape and you're just getting slightly longer. Month two is where it starts to feel intentional - you can tell something is happening. Month three is where most people fall apart. The sides are starting to push out, the back is doing something it shouldn't, the top is too heavy to sit flat and not heavy enough to train into a new direction. This is the awkward stage, and it's not a sign that the grow-out isn't working. It's just physics.
Here's the counterintuitive part: you still need to go to the barber while you're growing it out. Not to take length off, but to keep the shape maintained. The sides and back can be cleaned up, the neckline trimmed, the overall silhouette kept tight - all without sacrificing the length you're building. A grow-out that gets no attention reads as unintentional, and unintentional is the thing that makes the awkward stage actually look bad. A grow-out that gets shaped looks like someone who's deliberately doing something with their hair, which is a completely different impression.
The practical rhythm for most guys is a visit every four to five weeks during the grow-out phase - not to shorten anything on top, just to keep the perimeter clean and the shape readable. It costs a bit in the short term but gets you to the goal looking like you meant it the whole way through.
There's no hack for the time. The awkward stage is just a part of the process, and it ends.