My experience was that I picked up “real life” really quickly. But, I'd also say that it was very different from “book”. I don't use much “book” on a day-to-day basis, but “book” is a very good framework to build from for “real life”. Here's my analysis, though, of how some people do better or worse with the transition:
Some people are great at book knowledge. Some people are great at real-life application. Some people are mediocre at both. Some people are great at learning one or both, but not as great at using that one or both, and others are great at using it, just take awhile to learn it. Because of these varieties of people, you get varied experiences in the transitional phase.
The mind required to ace an exam isn't the same mind required to be a great accountant. Sorry to disappoint anyone. 😛 I've known some people who were excellent accounting students and terrible accountants. People like that are where some of the “real life experience and book knowledge are totally different worlds” stories come from, cause you can be excellent at book knowledge and terrible at real life applications.
Conversely, the mind required to be an excellent accountant can be terrible at taking an exam or writing a paper, so can be a terrible student. Again, that leads to “real life vs book is totally different” stories.
But, there's some people that their mind excels at intertwining both. Those people are the ones that look at this notion and scratch their head. I'd say @KayBee is one of those – she reads the textbook, applies it to her work, sees how both relate to each other, and both experiences are enriched.
There's also the people who excel at both, even if they don't always see how they relate to each other. I'd put myself more in this group. I wasn't a Straight A's, 4.0GPA, EWS winner, but school comes easily to me, and I'm pretty book-smart when it comes to accounting. At the same time, “real-world” accounting has come fairly easily to me. But, it's not because I've been able to mix the two together very well – I find the book knowledge has given me a framework to build on, and there's things that it alerts me to that I might miss otherwise, but on a practical day-to-day basis, the knowledge I use is the knowledge I've gained through life and working, not through books.
So, in conclusion, I think that the people who find real-life and book knowledge to have a lot of overlap aren't as common as the people who don't, just cause there's more categories of people who don't, but that doesn't mean that everyone finds real life harder. It's just different skill sets. Sometimes the people who are stars in school suck at life or vice-versa, and some are good or bad at both, but most people average out over life. Real-life wasn't a hard shock to me, but it wasn't because school prepared me, more cause life from 0-21 prepared me for 21-25 (and I hope it's prepared me for 25-105 😛 ).
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Edited to add contribution to the software conversation: Most new software I've had to learn at a new employer was the Lotus suite (wouldn't use Office) – their calendar was really weird, so it counts as a new program, a bookkeeping/payroll tax program, and an income tax program. At another employer, we used 2 different ERP systems, and at my current employer, we have one ERP system. I'm just glad that all except the one have used “real” Excel – I missed my Excel so much when I was at the Lotus employer… The most challenging from a software perspective was the employer with two ERP's, though, since it was my first experience using an ERP system, and I was learning two simultaneously, one of which no one in the office knew well; however, within a few months, I was able to troubleshoot both better than many of my coworkers. The trick to learning software is to have a comfort level with software in general. You don't have to know EmployersCrazyAccounting 123, you just have to know software in general, and then you can pick up whatever software is thrown at you. That's one of those things where life prepared me for accounting work. My accounting information systems class didn't do anything to help me learn two ERP's at once or to learn Lotus's antique ways of doing things, but 20+ years of poking around computers and exploring my world in general did teach me how to explore a program and learn its quirks, including a new ERP system.
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