Come up with many possible point Bs where you'd like to end up. Find people in those positions, whether it be CTO, lead programmer, freelancer, or whatever and ask them what it took for them to reach that destination.
Part of the difficulty is that if none of the people at point B has gotten there by going through point A, it is going to be hard for them to know your challenges.
For example, if a history major from a small liberal-arts college asks me how to get into DevOps, my answer is going into be affected by my having been able to spend several years hanging around SIPB, which is basically MIT's DevOps club. Maybe they can do the same, but it would be pretty expensive.
My response would be "Why DevOps?". That's it. Let them talk.
Then information can be found. Interesting responses and experiences. Find a winner.
Responses, motivations, and pointers, telling me far more than, that you did to your hypothetical applicant: plant into a well and expect them to be able to jump out by having a DevOps club experience at an 'expensive' (unclear if social, financial, or other cost) club. Grow people or crush people?
Doesn't have to be the same club or a formal club at all. The takeaway from you is to get involved with a group who enjoys what you want to get into. Good advice.
Them problems comes when all the people in those positions just got the job from their friends, are thankful for the jobs you helped get them, but just don't have any time for you.
Come up with many possible point Bs where you'd like to end up. Find people in those positions, whether it be CTO, lead programmer, freelancer, or whatever and ask them what it took for them to reach that destination.
Plot your course from there.