If there is one thing that you should be learning from listening to the Cash Flow Diary podcast, it's that failing is a part of success. You cannot avoid failure events. It's how you handle them that matters.

If there is one thing that you should be learning from listening to the Cash Flow Diary podcast, it's that failing is a part of success. You cannot avoid failure events. It's how you handle them that matters. In this episode you get a little insight into some of the small failure events that occurred at our recent Black Friday live-streamed Cashflow 101 board game event. Things didn't go as smoothly as we intended, but it's okay. The game happened, we had a great time, people as far away as Barcelona were watching us and learning how to run games better, and we received excellent questions from viewers and players in the room. We learned from all the little things that didn't go well or as well as they could have. Awesome! We didn't just pack it in, take our ball and go home. We managed the technical issues and moved forward anyway. Apply this insight to what you're doing as a Real Estate Investor. If you talk to 10 people and still don't have a YES from a seller, buyer or investor, don't stop and tell yourself “it” isn't working. Keep going. Take from those experiences and see what you can learn from them. Dissect the experiences. Define your process. Redefine the process. Get better at what you're doing. Study the Four Levels of Learning. Even if you've watched our video on that topic before, go back and watch it again. Your goal is to become Consciously Competent! That's the fourth level. For now, listen to this episode and learn why getting comfortable with failing forward and failing often is okay. Listen Now

Show Notes


On this episode of Cash Flow Diary, J shares an inspirational quote by Willis Rodney Whitney, “Some men have thousands of reasons why they cannot do what they want to do, all they need is one reason why they can.” If you adhere to what J shares with you in this podcast about learning to fail, you will have a greater shot at making it!

Episode Rundown: 

[02:45] Giveaway update 

[03:17] J’s inspirational quote 

[04:07] Three things to benefit from 

[05:32] Fail forward 

[07:33] Seek with intent to correct

[08:34] Fail fast

[11:13] The four levels of learning

[15:15] Fail frequently

[20:51] The schooling system and failure

Key Lessons Learned:

  • Many of us believe that it’s okay to say “oh well, I’ll start that next year,” but it’s not.
  • Keep the momentum going with whatever you’ve started and make sure you finish. Whatever you think you want to start, make sure to start now. Don’t wait.
  • An offer is just an invitation for a conversation.

Learning How To Fail: 

1) Fail Forward 

  • Start before you think you are ready and fail forward.
  • You learn from what went wrong.
  • ‘Wrong’ is just something that did not go the way originally intended.
  • When you execute a strategy make sure to review the process. Ask “what didn’t go as intended? What in that experience can I use the next time I attempt, and improve upon the experience I just had?”
  • Seek with the intent of correcting.
  • Seek areas where you may not have gotten it right.

2) Fail Fast 

The Four Levels of Learning: 

  • 1) Unconsciously incompetent (we don’t know what we don’t know)
  • 2) Consciously incompetent (know what you don’t know)
  • 3) Consciously competent (know what you need to do)
  • 4) Unconscious competent (the zone)
  • The skill set for the above is perseverance.

3) Fail Frequently

  • What would the world look like if Thomas Edison or Michael Jordan only attempted once?
  • We can model and imitate others, but the only time we truly learn is through failure.
  • Sometimes you have to try something 100 times to master it.
  • The schooling system has taught us to get it right the first time, without help and immediately.
  • When you choose to become an entrepreneur, it is difficult to become more than you are because in order to do that, you have to experience the process known as failure.

Thank you for listening! If you enjoyed this podcast, please subscribe to the show in iTunes  

Links to Resources Mentioned 

Cash Flow Diary Events 

Learn Investing Now  

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Are you prepared to fail forward? Find out why you should learn how to fail w/ J Massey cashflowdiarypodcast.com @CashFlowDiary   

Failing frequently can be one of the best things you'll ever do. Find out why  w/ J Massey cashflowdiarypodcast.com @CashFlowDiary 

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