I sympathize with the "lost time" thing. I started my SW career at age 26, but didn't crack $100k until 34. I know inflation, etc. but you're doing better than you think! Anyways I think you have the right idea. Switch jobs every 2-3 years to get a diverse background of experience, and to elevate your pay. Salaries tend to plateau around 10 YOE, that's the marker for where it makes more sense to find a job you like long term and do senior+ or staff level work, because the large payoff of changing jobs gets a lot smaller IMO. You can shortcut this by jumping to a larger tech company, a FAANG, or a VC-backed startup (levels.fyi is great for checking if a prospective company is worth your time, at least for big companies). The startup risks are obvious, these are not stable jobs. The FAANG/big tech risk is they are so large, you may end up doing extremely niche work that doesn't translate well anywhere else, and a layoff leaves you hard to employ. Another shortcut is overemployment with remote jobs. Again, there are risks, but if you avoid the risks it is very lucrative. At your level, basic leetcode/DS&A will get you hired into a new role. In ~2 years, interviewers will start to expect you to do high level system design. The best way to get ahead of this is hands on work, so make sure each new role is also expanding the scope of the problems you're working on (subsystems in a component -> a whole component -> multiple components). You should also make sure it becomes easier to draw a direct line from your work to a positive revenue/cost impact on the company. If you score a big 50% raise or similar in your next role, take the opportunity to max out your 401k contributions. Ultimately "making up for lost time" is about living comfortably when you're done working. Some employers with middling pay might have amazing 401k matches too so don't sleep on that (best I ever had was a 12.5% match, the pay sucked, but I might be back). Final note is nobody is going to judge you on your age/appearance compared to your level. I've worked with career changers in their mid-50s. It's never too late to start a software career if you have the drive to make it work.