These are some of my favorite books and other resources that I have used to plan for retirement financially and psychologically:

• Your Money or your Life by Vicki Robin and Joe Dominguez. The book that started the FIRE movement. Must read to help reset/reframe your relationship to money and time.
• Through the Dark Wood – Finding Meaning in the Second Half of Life  by James Hollis. Written from a Jungian perspective, helps you to understand meaning, psychology, and spiritual aspects of transitioning to a second act.
• Halftime – moving from success to significance by Bob Buford. Must read on how to think about the preparation and transition to a second act.
• Stuck in Halftime – Reinvesting your one and only life by Bob Buford. Follow on book on how to get past blockers during the transition.
• From Strength to Strength – Finding Success, Happiness, and Deep Purpose in the Second Half of Life by Arthur Brooks. I actually wrote a blog about this one and how to harness your crystallized intelligence to help others on their paths. Really good read.
• They Happyness of Pursuit by Chris Guillebeau – inspring story of his purpose to travel to every country. Shares a bunch of entertaining and audacious real-world quests from people all over the world. Inspired me to think bigger about my goals in the second half of my life.
• Work Optional by Tanja Hester. Practical take on the FIRE movement that accentuates more income so you don’t have to live on $5/day.
• Playing with FIRE by Scott Rieckens. Another practical take on FIRE with real case studies. Lots of young people living on little but inspiring.
• Set for Life by Scott Trench. Another useful take on FIRE.
• One Bullet Away the making of a Marine Officer by Nathaniel Flick – Excellent story about how to handle the identity transition, in this case an active Marine into civilian life. Great story about purpose and the importance of purpose. Recommended by a friend of mine who recently left active duty from the Marines.

Here is my take on the process:

• Financial
  • Figure out what you spend over a year and make it really accurate.
  • Model what inflation will do to your expenses over time and split expenses into ones that are affected and those that are not.
  • Get 25x your annual expenses (or close to it) in overall assets in liquid assets.
  • Get 1 year of expenses in highly liquid assets making at least 5%. I used bonds (worthybonds.com and treasury).
  • Build a dividend cushion of 2x your annual expenses in order to live off of payments instead of selling principal during down markets.
• Psychological
  • Read as many books as you can about this.
  • Talk to as many people that have done this successfully.
  • Start investing in your community, friendships, and hobbies outside of work, well before you quit your job.
  • Spend a lot of time on the mat working through any fears or anxieties.
  • Shore up your weak spots with backup plans. Your backup plan should have a backup plan.