Words of Wisdom about Failure

I recently came across a post on reddit (r/Entrepreneur) in which someone posted about how he has “failed” numerous times on his entrepreneurial career path and is losing hope:

Since graduating back in 2005 I’ve been starting and running a number of my own companies, when times got hard I’d take on work but these jobs would last a couple of months at best as I’m simply not capable of working a 9-5. I literally lose my mind and find it impossible to even go into a regular office and spend all day with strangers doing something I hate. Unfortunately, following the long term failure of all my business ventures over the years I’m now in debt, have earned a tenth of what my peers have in the same time and I’m back living with my parents at the ripe old age of 33. I really feel like I’ve reached the end of the road and my confidence has bombed so low I feel I couldn’t even imagine walking into a job interview for a low level job never mind running a business. I guess I just wanted to see if anyone here has managed to pull through long term failure and poverty like this and if so, how did you manage? Thanks for reading.

As always, the comments/replies to this post were extremely, extremely insightful, inspiring, eye-opening, and a nice cold “slap-in-the-face” reality check. These are the top comments I loved:

  • List your last 5 projects. I would bet that your projects are more of the “brilliant idea” types and not the “simple solutions that other people already provide” types. I could be wrong, but I’d be interested in seeing what your last 5 were.
  • I hear you when you say you hate working 9-5, but if you don’t have a steady income you hardly can focus on your own venture, you will be distracted by emotional pain. Don’t treat your life as a failure. It’s an experience. You can build something on it. You know what doesn’t work for you, which is good. You certainly won’t repeat many mistakes. Divide your goals into short-term (aka “survival” goals) and long-term. Find an occupation that meets your short-term goal. Something you can sustain. In these situations people usually hate jobs, because they feel like defeated. Don’t feel like that. Any job, new people give you a chance to study something new, probably that’s where the business idea of your life hides from you! So meet that short-term goal, but keep your long-term goal in mind as well.
  • Entrepreneurship requires great discipline and working a lot of tedious jobs. People who can’t stand 9-5 jobs usually also have no discipline and can’t deal with tedious jobs.
  • Entrepreneurship is not just about having good ideas, it’s about working for yourself. It’s about work, it’s about seeing opportunities and taking advantages of them, even if it’s not fun. Self discipline is probably the most important skill in this field, if not in life in general. I really wish I would have know that when I was younger. If there was one thing I would go back and tell myself as a child, it’s that you need to learn self discipline and control, that things that are difficult should still be done, even if they’re not enjoyable. Productivity and accomplishment come from either passion or discipline (however, this doesn’t guarantee success). Ideally you have both. But few people have passion enough to last through the hard times, it’s discipline and a sense of duty that sustains. I know a guy who everyone thinks is brilliant, and he is, but I’ve known the guy for 30 years and can tell you that what makes him valuable isn’t his intelligence, it’s the amount of work he puts in to things, even if it’s stuff he doesn’t enjoy doing. It’s purely the amount of work and effort that he puts into things that keeps his company going and profitable. I remember some magician, I think it was Penn Jillette, who said that a lot of magic tricks are really about spending an insane amount of time learning to do something that no sane person would spend time learning to do.
  • Dude, I’m still reinventing myself at 42. All this stuff that happens makes you a better, more rounded CEO when you get back on the horse. Don’t stay down long, …6…7…8… get back up and start swinging. Keep meeting people, keep finding new things to do and keep learning. You’ll be fine. Last point, this shit is a game. If you don’t enjoy playing the game and only care about winning every single time, you’re in the wrong game. Go make furniture or something. Business is hard and you are going to get your ass kicked sometimes. How would you know if you’re up if you’ve never been on the mat, with your consciousness waning and the taste of pennies in your mouth.
  • Mindfulness my friend. Retake your brain. Your post is all about can’t and not reaching what others have. Your current situation is more than likely a product of letting your thoughts run the show. Trust me, if your were successful you would still be in this state of mind. Fix the foundation first.



There were a ton of more golden pieces of wisdom in that thread, but the most important theme that resonated throughout most of the comments was the need to have the right attitude and mindset. Many would say persistence is the key to succeeding, but I would argue that it’s actually very difficult to keep persisting if you don’t have the correct mindset in place first. How do you see the path in front of you? Do you have a “do whatever it takes” mentality? This post gave me the inspiration and dose of reality I needed to understand at least the foundation I need to start building as I start looking ahead toward the goals I want to accomplish. Failures will come and go – they are inevitable. But with the right mindset, they should be seen as “challenges” or “lessons” rather than “failures” and I think this is one of the foundational keys of success for those that were able to achieve the things that we dream of one day achieving.


Be nimble, and keep moving and pivoting when you hit a wall. It’s like a maze – are you going to just give up when you hit a dead-end, or are you going to keep moving until you finally figure out how to reach the end. Keep going.