Great question, and excellent to see the convo happening here. I'm in my 40's now and started thinking about this around age 35. My theory was that as I got older there would be younger designers willing to work longer hours for half my rate, so I knew that I needed to pivot myself to a position of leadership in one form or another in order to continue to provide value to my employer.

Leadership could be management, but it could also be a very high level IC role. This is an important distinction to make. A strong Principle Designer or Staff Designer or whatever you want to call it is invaluable to a company—so an IC path still has possibilities for leadership.

I noticed things in myself that made me lean more toward management. I enjoy the people aspect for sure, but more importantly I noticed that I cared less about the creative work that I was producing and became more interested in helping others produce incredible work. Since taking the management track, I've worked with designers who can design circles around me, and I love it. I love being able to help them produce their best work.

As for retirement, I'm doing the usual 401k, savings, stocks, investments, etc. I've worked out a spreadsheet with my best guess for how much I'll need to live on per month when I'm retired, and I'm working backwards from there. Here is an example of that type of spreadsheet (https://docs.google.com/spreadsheets/d/1991xCRgJWznq6WAUt6j-va4xXKZ2Q2y1mGO4vTZXELI/edit#gid=1319135868)

I will also add that because our industry is so young, I do feel it is important for folks with more years under their belt to remain in this industry to raise up the next generation through mentorship, education and leadership.