@anon0938 Always take the option that pushes you away from a "comfort zone". The best heuristic you can follow for career is: Do what you are most curious abou

@anon0938 Always take the option that pushes you away from a "comfort zone". The best heuristic you can follow for career is: Do what you are most curious about and meets your current & projected financial needs and still allows you to spend time with loved ones (where applicable). I have consistently selected jobs/work where I'm most likely to learn in the areas I'm curious. Pen-testing (one of your options) is a great area that is only going to grow in demand. As Marc Andreessen is often quoted as saying: "Software is eating the world". The problem is that the vast majority of the code that is written is insecure! If you are able to do the 6-12 month learning program and it results in a certification, that certificate is a "safety net" that you get to keep for the rest of your career whatever you do next! I did something similar and have no regrets. It opens doors and being the "security expert" on a software project means you always get consulted when something mission critical has to be built. Once you have enough cash, invest it in cashflow-producing assets so you have an additional stream of income (if you don't already...). Then you can afford to re-think what you do with your time and do exactly what you want with your life. If you feel "insecure" write down why you feel that way. If you don't already keep a journal, start today. Write down your thoughts on why this decision is difficult. And refer back to your writings on a regular basis to "check-in" with yourself. Bottom line: invest in yourself. keep your learning curve steep and switch jobs (upgrade) whenever you feel that you are no longer learning. This might feel like a "lack of loyalty" to your employer, but the fact is that you will be more valuable as a team member the more you learn, and if you can impart your knowledge on a given project in 3 months, why would you stay there for a year?! I started contracting 6 years ago and have never looked back. The money is much better than "full time" and it's also way more flexible. If you develop the skills/credibility, you will never be without work. And if you cannot handle the "uncertainty" of contracting, you can always get a full-time job again.