The closest you're going to get as a reloader to knowing your pressures is using what's in your load manual. You need to load as close to the listed OAL as you can, use the same bullet that the data calls for, and use the minimum powder charge for the given range.
Take this ammo to the range and shoot it over a chrono. Look at the velocity. If by some miracle, your velocities are similar to what's in the book, it would be logical to say that your ammo is at the lowest pressure listed for that powder/bullet combo. Most load manuals have pressure ranges; they list min and max.
The problem with picking a powder charge in the middle (if you're trying to determine pressure AND assuming your velocities for a minimum charge mirrored what's in the manual) is that you don't know the pressure curve of the powder as it progresses from a minimum charge to a maximum charge. How does it arrive from the minimum to the maximum? Unless you have a graphical representation of the pressure curve for that loading, you will not know what values to expect within the range of min to max.
Ok, so that was a lot of typing. In short, you probably will not know what pressure you are at. You could maybe get a ballpark number, but nothing concise. The reason that actual velocities you get at the range seem lower than the book is because they are probably using a test barrel, a length of which we do not know. If you're not matching velocities with a 4.5" to 5" barrel, it's safe to say they are probably using something that is 7-8 inches long, so using your chrono'd velocities is a crapshoot at best. There are just too many unknowns.