This is a good question! It is all a matter of how to define an improper integral. The traditional way is to write
$$\int_a^b f(t)\, dt = \lim_{x \to a} \lim_{y \to b} \int_x^y f(t)\, dt$$
whenever one of the bounds is worrisome. In particular, we can write
$$\int_a^b f(t) \,dt = \lim_{x \to a} \lim_{y \to b} \left(\int_x^1 f(t) \, dt + \int_1^y f(t)\, dt \right)$$
or
$$\lim_{x \to a} \lim_{y \to b} \left(\int_x^1 f(t) \,dt \right) + \lim_{x \to a} \lim_{y \to b} \left( \int_1^y f(t) \,dt \right) $$
so that
$$\int_a^b f(t)\, dt = \lim_{x \to a} \left(\int_x^1 f(t) \,dt \right) + \lim_{y \to b} \left(\int_1^y f(t)\, dt \right).$$
Now convergence means that the integral is finite and the only way for the sum of two numbers to be finite is if both are finite. Hence your professor's comment. All of the above assumes $a < 1 < b$ and that there is no trouble with $f$ near $t=1$.
But you are right that you can get cancelation if you take the limits differently. Instead of taking the limit to a and then the limit to b sequentially, if you took them at the same time--that is to say you combined them--you could possibly get cancellation.
Here's an example. If define instead the improper integral as
$$\int_{-\pi/2}^{\pi/2} \tan t\, dt = \lim_{x \to \pi/2} \int_{-x}^x \tan t\,dt$$
then
$$\int_{-\pi/2}^{\pi/2} \tan t\, dt = \lim_{x \to \pi/2} \left(- \ln \cos(x) + \ln \cos(-x) \right) = 0.$$
What you are thinking of is a useful concept and it often comes up with the term Principal Value in more advanced calculus courses.
Best Answer
Consider the following summation:
$$ A=1\cdot 1+\frac12\cdot1+\frac13\cdot1+\frac14\cdot1+... $$
That's a sum of the areas of an infinite number of rectangles of height $\frac1n$, where $n\in\mathbb{N}$, and width 1. Do you agree that's nothing more than the harmonic series? Moreover, the area under the curve $f(x)=\frac{1}{x}$ from $1$ to $\infty$ is clearly less than $A$ and lies totally within $A$ (see the picture below). However, the area under the curve $f(x)=\frac{1}{x}$ from $1$ to $\infty$ doesn't add up to a finite number. It goes to infinity. What should be happening with a piece of area that's even larger than that? Obviously, it must also be infinite. Therefore, the harmonic series diverges.