Failure + Reflection + Another try

Failure + Reflection + Another try = Competence.

Brandon Webb

The meaning of the quote

In 2009, Brandon Webb sat in his pickup truck on the cliffs above the Torrey Pines glider port in San Diego while his lawyer told him his first startup was finished.

Webb had put his life savings into the company and raised just under $4 million from investors. His marriage ended around the same time. He walked away flat broke.

Instead of replaying the loss, he wrote down what the failure had taught him. He now knew how to raise money and read a financial statement, and he had learned the hard way to pick his business partners more carefully. He took a job, saved up and started a small website called SOFREP from a sketch on a napkin. It grew into a military news company with more than 50 employees, most of them veterans.

The quote packs that story into a single equation. Webb treats competence as something you build, with failure as the first ingredient, and each part of the equation falls apart without the other 2.

Failure

A failure only counts in the equation if you stay in the game afterward. In the podcast The James Altucher Show, Webb drew that line himself:

“Failure is necessary to be successful in life. There’s a big difference between quitting and failure.”

The golfer Bobby Jones learned that at 19, when he tore up his scorecard at St Andrews during the 1921 Open Championship and walked off the course. He came back 6 years later and won the Open on the same course. Coming back is what turned his walk-off into a failure he could learn from.

Reflection

Reflection is the part most people skip. They lose, feel bad for a few days and then try again the same way, so they get the same result.

The US Army built reflection into its routine with the after-action review. After an exercise or a mission, the team sits down and compares what was supposed to happen with what did happen. Nobody hands out blame. The review runs through 4 plain questions:

• What did we expect to happen?
• What happened?
• Why was there a difference?
• What will we do differently next time?

The last question turns the review into a plan for the next try.

Another try

The next try has to be a different try. In 1978, James Dyson started building a vacuum cleaner that wouldn’t lose suction as it filled up. Over 5 years he built 5,127 prototypes, and he later said each failed version brought him closer to solving the problem. The last one became the first bagless vacuum cleaner.

You don’t need 5,000 attempts for the equation to work. A student who fails a driving test on parallel parking, works out that she turns the wheel too early and practices that one move before the retest is running the same equation on a smaller scale.

Exercise:

Which part do you skip?

Most people are strong on 1 or 2 parts of the equation and weak on the third. These 4 steps show you which part is yours.

1. Pick 1 setback from the last month.
   A test, a job application, a match or an argument that went badly. Write it down in 1 sentence.
2. Check what you did next.
   If you stopped trying, you skipped the last part. If you tried again the same way, you skipped reflection. If you’re still thinking it over weeks later and haven’t tried again, you’re stuck in reflection.
3. Answer the 4 after-action questions.
   Write your answers on paper and keep the last one to a single change you can make.
4. Put the next try in your calendar.
   Pick a date within 7 days and make that one change.

Run that loop enough times and the last part of the equation takes care of itself.

About the author

A few weeks after his 16th birthday, Brandon Webb fought so badly with his father during a family sailing trip across the South Pacific that his father threw him off the boat in Tahiti. In the book The Making of a Navy SEAL, Webb opens his life story with that moment.

He made his way back to California alone and returned to the scuba diving boat he had crewed on since he was 12. The owner let him keep working there while he finished high school.

Navy SEALs sometimes dove from that boat, and meeting them gave Webb a goal. He joined the Navy in 1993, trained as a helicopter rescue swimmer and finished SEAL training with Class 215 in 1998. He deployed with SEAL Team 3 to the Persian Gulf and to Afghanistan.

Later he ran the West Coast SEAL sniper course, where his students included Chris Kyle and Marcus Luttrell. In the foreword to The Red Circle, Luttrell writes that Webb stayed after class hours to work with students and credits that training with keeping him alive in Afghanistan.

Webb left the Navy in 2006 to spend more time with his family. After the failed startup and the success of SOFREP, he built a second company, Crate Club, and sold it in 2020. He has written or co-written more than 12 books.

16 years after that talk with his lawyer in the truck above Torrey Pines, Webb shared the equation with James Clear, author of Atomic Habits. Clear published it in the October 9, 2025 issue of his newsletter 3-2-1, where you can find it next to his other ideas for that week.

Resources

• The Making of a Navy SEAL (Book)
• The Red Circle (Book)
• Brandon Webb on The James Altucher Show (Podcast)
• How losing first taught me to win big later (Article)
• 3-2-1 newsletter, October 9, 2025 (Article)
• After-action review (Wikipedia)
• I never learned anything (Article)
• The garden of failures (Article)