I’ve already been working on this answer in my spare time and I wouldn’t want to see the effort go to waste, although it’s not strictly on-topic, anymore. Nevertheless I’m posting it here in the hope that it might by useful, both for others and for the OP in the more general case. I’m adressing the first version of the Gaypril logo.
There are few hard and fast rules in design, if any, and to my knowledge none that hasn't been successfully broken by designers. So, if the question is “How to make my logo better?”, then I’d have to ask back: “Well, what do you want to achieve? What means do you want to employ?” Leading to a back and forth exchange that quickly starts to feel like working with a client.
However, if the question is: “Here’s the model logo whose effect I tried to emulate. Here’s my own logo attempt, where, as far as I can see, I did everything like in the model. Why is it still not working?” That’s easier to answer, because I can point to the features of the Canada Road Trip logo and explain why these make the logo “work.” And I can explain how those features are in fact not present in the Gaypril logo. The Gaypril logo could employ very different means to achieve visual cohesion.
Nothing that I’m presenting here is in any way mandatory! I’m discussing the options realised in the Canada Road Trip logo that you took as your model. There are also numerous other options.
Because that’s what this is about: visual cohesion. Or in other words: composition. In design, you have to establish the rules by which your design works. I recently wrote in another context that design is about creating problems for yourself and then solving them. It’s in some ways like solving a puzzle, except that while solving you also invent the rules by which the puzzle has to be solved. That makes it actually harder!
The impression of boredom doesn't generally come from a lack of “interesting” elements. Rather it stems more often than not from the fact that those element are put together in a manner that appears to the eye as arbitrary. Interest stems from the expectation of surprise, yes, but randomness isn't surprising. To take an extreme example: No two white noise patterns are exactly the same. And still nobody would look at them with any expectation to see an interesting placement of white or black pixels. If you want your work to be interesting you have to compose it in a way that the elements fit together meaningfully and provide a sense of unity in an interesting way.
This is harder to do the more heterogeneous the elements are that you want to compose. This is why beginners are often advised to keep it simple.
Please note that I’m not trying to discourage you! Or making the task seem exceptionally hard. On the contrary, I think you are on a good way and noticing that something’s not working is the first step towards improvement. The rest comes with practise and experience.
I should also point out that I don’t expect that my analysis of the Canada Road Trip is what its designer consciously had in mind, at least not everything. Many decisions in design are made intuitively. I’ll come back to that at the end.
This logo has a clear circular form. Note how the mountains at the top protude. This is, because we perceive pictorial elements like these as a unity: The top line of the mountains (without the sunrise) are perceived as continuing the line of the circle. But since we perceive the mountains as unity, our eyes average their height. If the mountains where placed more towards the centre of the circle, they would appear as too low.
Note also how the “C” of “Canada” supports and continues the circle line. It, too, sticks out and has to, for the very same reason. The same is true, though to a lesser extent, for the letters “da”. In short, the form of the logo unambiguously evokes a circle and has little to counter that notion. The only element effectively going beyond the circular shape is the sunrise behind the mountains. But its lines carry much less visual emphasis, especially since the lines of the mountains are so much more dominant. And because the logo is generally well composed the slight disturbance of the circular shape appears as intentional and meaningful: It’s a well placed accent, so to say, the sunrise behind the logo itself.
Here the circle is fully supported only by the text at the bottom, which, in addition, is de-emphasized with a comparatively thin and wide-spaced font. The sun at the top has much more emphasis. Its vaguely star shaped at its upper outline (the rays) and the half circle of the sun doesn’t support the circle shape of the logo itself, but competes with it. In effect, the sun doesn’t just protude, it counters and escapes from the attempted circularity. The same, more importantly, goes for “Gaypril”: It clearly stands out as the most important visual feature. But not only does it not support the circle, and not only does it protude, it introduces a shape of its own: a parallelogram slightly warped to a wave form.
Nothing of these are a “problem” per se. You can have a counter shape in rhythmical contrast to the main shape. You can have elements “escaping” from the structure you are trying to create. You are creating your own rules and you are breaking your own rules.
Breaking the rules is good. But before you can break the rules, you have to establish the rules.
Here, the logo doesn’t successfully establish the circle.
Grey Values and negative space
Look at the grey values. (I hope “grey values” is the correct English word.) The average of black and white in the various elements is evenly distributed. If I added more blur, the logo would eventually become evenly grey. Only the bear stands out as a blacker area. As does, to a lesser extend, the mountain at the top, thus acting as a counter weight to the bear.
White space between the elements is roughly evenly distributed. Meaning: White space is neutral and not intended as a dominant element of the composition. There are works where white space (better dubbed “negative space”, then) and its shape is just as much important as the foreground elements itself, for instance in traditional Japanese woodcut printing. This is not one of those works.
As you can see, all the weight is at the top, with “Gaypril” having the most weight by a large margin and the sun coming second. Note in particular how little weight the bottom text in a half circle has. This contributes largely to the logo not establishing its intended circle shape.
I have a gut feeling that maybe you intuitively were aiming for this: A circle with the upper half being darker and the lower half lighter. If that’s the case, then it’s a good instinct. If the logo were clearer, were successful in establishing the circular shape, if it would give the overall impression of being thoroughly composed, then this could work very well. As it stands, there’s too much visual noise for this to take effect.
To some degree, this is an elaboration on white space, but with a different twist. The distance between various elements is roughly equal, in some cases very roughly. But that’s alright. The eye as little for comparison. If there were mostly straight lines, then more precision might have been necessary.
Note how the designer tilted the bear in order to have its back and front paw in equal distance to the circle:
(The dotted line is the line through the circle’s centre, orthogonal to the baseline of “Canada Road Trip”.) Often you have to cheat a little. And you may! What matters is the naked eye of the spectator, not what you can measure with a ruler. It’s a judgement call with how much you can get away. Here, if you draw a line from the top of the mountain through the centre of circle, then the bear is roughly orthogonal to it. Maybe that contributes to the bear’s tilt looking good. Maybe it even establishes a secondary axis. I honestly don’t now. This is a matter of interpretation.
Here the various distances differ widely. Why am I measuring the radial distance? And not, for instance along the tilted vertical axis and perpendicular to it? Because of the comparison to the Canada logo, which works as a circle. Here it’s actually unclear, which leads to my second iteration over shape:
Shape, the second
The Gaypril logo hints at a rectangular shape inside the attempted circle. Again I have a gut feeling that this might have been what you wanted on an intuitive level. And, again, a decision like that could very well work, if it were actually both clear by itself and not countered by conflicting visual clues.
There’s a rhythm to the Canada logo: The heights measured a long the baseline of “Canada Road Trip” are roughly repeating. I have the golden ratio proportions overlayed in red and blue. Again, there are no straight lines, so a rough correspondence is more than enough to establish a sense of rhythm to the naked eye.
The fact that it’s roughly the golden ratio matters less than the fact that it’s a repeating proportion. For instance, 1:2 or 1:3 would work just as well in terms of composition, though in a sense the golden ratio is probably more “neutral” in this context.
To my surprise, I learned from the internet that some people find the golden ratio dubious. There’s nothing magical about it, though: If you need a proportion that is smaller than 1:1 and larger than 1:2, yet is still distinguished enough from either to look intentional, then you cannot but end up at with what for all practical purposes is a “naked eye golden ratio”.
For the most basic purposes the golden ratio is roughly 2:3. Like here where there are no straight lines providing a clear reference. Or, for instance, if you just want to divide a page into two parts. In such contexts, a more precise division isn’t discernible. Finer precisions like 1:1.618 become meaningful only when building up visual relations spanning multiple golden ratio divisions, since only then the golden ratio’s unique mathematical properties might come into play. The target audience might be relevant, though: If, for instance, you design a poster for an exhibition on Mies van der Rohe or for an auction of renaissance paintings or some such, then your target audience might be more sensitive.
This proportion is also present on a larger scale:
Again, you don’t have to use repeating proportions. But in the Canada logo it’s one aspect that provides a sense of intentionality in its composition.
Practising your Sense of Composition
I mentioned that most designers probably make this kind of decision intuitively, often not consciously aware of it. But there is nothing mysterious about intuition. It comes with experience and it can be educated.
One very good exercise is what you just did: Trying to recreate something that you like. As you probably know, that takes time, though, and quantity does matter somewhat. Another good way to educate your sense for composition is to draw works that you like. Here’s an example from my sketch book:
As you can see, I’m not really good at drawing, but it serves my purpose. I try to make a habit of drawing one work that I regard as masterful every day. Well, in reality it’s just every other day, or every third day, but I’m trying to be more disciplined. That drawing doesn’t have to be good. More importantly, the aim is not to copy the original. Nothing would be gained, if you just put tracing paper on the original. The goal is to reconstruct the work on your paper. It’s best to think of it as “thinking with your pencil”. It’s about discovering what visual relations matter for the composition. It’s also about committing options for composition to your subconsciousness.