I’ve never been a big fan of formal mentorship or the push for new people to find mentors. I’m okay with the concept and if it get’s setup properly, then great. I think it puts too much pressure on mentees and it can be frustrating if the assigned mentor isn’t into it. On the flipside I’ve heard plenty of good mentors give mentees recommendations and then don’t see a follow through. I’ve also started seeing young professionals getting hung up on this concept and hold themselves back because of it.

A lot of that is from my own experience. There’s not one individual person or group of people that I can point to as being exceptional mentors for me. They’re out there. I just haven’t had the fortune to run into them. Instead I’ve appreciated the more organic mentors I’ve had. The ones that are peers of mine or even subordinates. Yes, subordinates or people early into their careers are a mentor to me because they bring fresh ideas and perspectives. That’s why I wrote the blog post - Mentorship is a two way street. A year later I’ve discovered that there’s another form of mentor, books.

As I’ve reflected on my career and who I am as a person I can find certain books that have really impacted me and helped me more than any one person. Specifically books about current and historical people. The last several years I’ve been studying stoicism and a lot of that study includes examples of philosophers from the pasts. Their words, their difficulties, and even more importantly their actions. I’ve also read books on Will Smith, Bruce Lee, and Winston Churchill. Churchill in particular has been fascinating for me because he dealt with a lot of politics. His struggles have aligned with some of the struggles I’ve had moving into management. That’s what a mentor provides. Experiences and difficulties they’ve had and how they handled them.

Again, not saying mentors aren’t important they are but it doesn’t need to be a person. Below are some books I’ve read that I feel have helped mentor me in my career (and still are).

Mentor Book Recommendations

The Official Biography of Winston Churchill - This is the current series I am going through. It covers the entire life of Winston Churchill and everything he or others have written about him. The shortest book is 700+ pages. I’ve found these books helpful as I’ve moved into management and run into the same type of politics at the companies I’ve been employed.

Man’s Search for Meaning - This is a powerful book by Viktor E. Frankl who lived through the worst conditions during World War II. It covers survival and the psychology around it. If you’re struggling at work this will highlight how insignificant a lot of it is when surviving a concentration camp in WWII required a mindset and luck. I spent several years trying to figure out my purpose. This book flips that on it’s head and says I get to make that determination.

The Supreme Commander - This is about Dwight D. Eisenhower and his leadership during World War II. It covers all the planning and execution of the Allied invasion of Europe. From this I learned about leadership, planning, and the higher up the chain the less control you have over individuals and the execution of your direction.

I Was Right On Time - Buck O’Neil is a fascinating figure in baseball. A lot of that is because he had such a great attitude towards life and the trials he went through coming up as a player through the Negro Baseball League and Major League Baseball. I’ve tried to foster a more positive approach to work and life though I am no Buck O’Neil he is someone to look up to as a positive influence. Also, check out The Soul of Baseball: A Road Trip Through Buck O’Neil’s America.

Final thoughts:

As you can see I have a very heavy lean towards World War II. Anything by Stephen E. Ambrose is excellent and covers individuals and leaders in tough situations and how they handled them good or bad. I’d also recommend Bernard Cornwell if you’d like some fictional mentorship. He writes historical fiction and looking back on my career I’ve modeled my professional career around two of his characters: Richard Sharpe and Uthred Ragnarsson.

You don’t have to read my recommendations. I would recommend identifying your interests in security and outside of it and look for leaders in those spaces and read up on them. Especially, if you feel frustrated with finding a mentor. There are multiple ways we can interact with a mentor.

This blog post first appear on Exploring Information Security