When I first started out, I did have a roadmap/plan thing but circumstances changed and it kind of just went out the window.
Halfway through university (2010) I found a brochure for a government department offering graduate roles for designers so that was the plan and I joined that graduate program at the start of 2013.
During my grad year I developed a plan for my professional development and I was on track until just before the end of my grad year when a hiring freeze hit the entire public service and my plan was no longer viable.
I pretty much just threw the plan out and the plan became to not have a formal plan. I just went with the flow and learned as much as I could and set out on a mission to find and connect with UX people outside of government- I found you guys about six months later. I found that interacting with people outside of my environment enriched my thinking and my non-plan based career became very people focussed. I found the most important thing to me in my career was the people I worked with.
I stopped over thinking things too- a lot of my stripe earning achievements have come from simply living in the moment and talking to interesting people. The opportunity to write professionally came three days after I randomly tweeted something at someone.
I've just left my government job and I'm about to embark on an adventure in a new job in the private sector and I'm really excited about that will bring.
I still have many, many stripes to earn and I think the biggest challenge for me now is developing a deeper level of expertise and growing my technical capability. I also need to start developing the beginnings of the manager and leader stuff in preparation for the future.