Ask HN: Dev promoted to more strategic role in startup. What literature?
Honestly I would get a mentor.  Find someone either in your org or out of your org that has the skills and career you would like to work towards and start talking to them.  If you hit it off you may have found someone who can help you through the bumpy parts of your career and help you plan your next steps.   Some people charge for this as career coaching and that can also have some value but it's challenging to sort out the best ones.  Every place I've gone I've looked for a mentor to bounce ideas off of and generally double check my thinking and how I'm approaching problems and my career.  You can go to industry events and start reaching out or just look for people you admire and reach out and start a dialog.I personally think the concept of apprenticeship is lacking in the technology industry and we loose out on what other older professions have with clearer career paths because of their established practices of guiding people though their careers.  That said I've seen it abused too so there always needs to be balance in these things.I personally coach about five people (for free) in my current company and they come from all areas of the org not just my group.  I was very lucky in the early days to have several great mentors in my life who helped me and I feel it's my job to pay that back now in the latter years of my career.Books are wonderful but nothing beats interacting with successful people.