Yes. Absolutely.
I haven't got a solution for it, but I know that solutions exist, because I know that sometimes I'm better able to switch tasks successfully than at other times. That variation implies that there are factors that make it harder or easier.
Practice is probably one of them; the more you practice transitions, the easier it gets. Knowing the next step after the transition helps, too. Knowing when they are expected to happen makes them more natural. Routines help, doing the same thing every time so as not to get stuck because you don't know the next step.
Check out "executive dysfunction". That's basically what you're dealing with. Find tips that are meant for people who have the milder types of executive dysfunction, such as what comes with ADHD, (the negative symptoms of) schizophrenia, or brain injuries to the frontal lobe. The level of executive dysfunction that most of us deal with tends to be bad enough to be a real problem without being so bad that people have to prompt us through basic self-care (but that happens, too, especially for autistic children). It's more of a problem with switching mental gears and planning tasks on the fly.
I've found that many of the tips recommended to people with ADHD help me, too--provided that they're from people who know enough about ADHD to realize that the hyperfocus of ADHD is as real as the inability to focus. There's less literature out there for people with TBIs that cause executive dysfunction, but there's some. It's worth a look.
And if you find any really useful strategies, do come here and tell us; we might want to try them too.