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.
  • Diversify across growth, income, fixed, real estate, and VC/PE.
  • 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.
    • Note on this, dividends can become a value trap and will go down in times of rising interest rates. You have to be patient and hold for the dividends, buying more when the price goes down, increasing your revenues.
    • Beware high dividend-paying stocks. I like 5-12% as the highest I trust.
• 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.
  • Do the work while you are in it.
• Trading
  • Buy great companies for the long term.
  • Buy incrementally.
  • Sell when you have a profit that is reasonable to you. Let some ride if you want.
  • Always put a stop-loss limit order in.
  • Do your homework on the market and individual stocks if you are a trader.
  • Don’t panic while everyone else is.
  • Never use market orders, always use limit orders.
  • Don’t own too many stocks – I have less than 10 in my trading portfolio and only swap in if I sell another.