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Failing Forward (and Why Baby Boomers Don’t Succeed)

Baby boomers have been raised to fight failing—and that just might be why many don’t succeed. Learn more in this week’s Grey Matters.

Failing Forward (and Why Baby Boomers Don’t Succeed)

Failing forward: Five big business mistakes baby boomers should avoid

[4:39] – Introducing this week’s podcast: The concept of “failing forward.”

  • The fear of failure often paralyzes people, especially the baby boomers who were raised to fight the idea of failing at every turn. In contrast, millennials have an entirely different philosophy about it: fail if you must, and learn from your failure. This attitude can mean the difference between success and failure, and is the reason why many of us from older generations ultimately never even bother to take a shot at success.

[11:07] – What having a side hustle means.

  • The philosophy of failing forward is you have to put 100% effort in no matter what, but success isn't necessarily the goal. It’s embracing the fact that the experience that you get from any new venture is the real goal, as opposed to a predefined success point.
  • The next philosophy is “fail big, shoot for the stars.” Regardless of when you fall short, you're still way far ahead. Baby boomers often shoot for success, causing us to limit our goals to only what we think we can attain. The reality, though, is that you will plan bigger if you don't have the fear of failure. 
  • The next key: how you react to failure. Analyze it, accept it, and embrace it. And then, you have to move on. 
  • Analyzing it means that failure is only worthwhile, if you learn something from it. Analyzing also means accepting the realities of the situation (“What did you have control over? What didn't you have control over in it?”) and then embracing it (“Okay, I'm good with that. Let's do this again, or let's do it this time, slightly differently.”)
  • Without the fear of failure to hold you back, you're free to make more radical, more aggressive decisions, without worrying too much about the potential consequences.

[16:48] – What having a side hustle means.

  • A side hustle is a job that you do outside of your normal activities, even when you’re already retired. If you’re employed to some capacity (or self-employed), a side hustle means that it’s something that's not right at the core of, and not with the same business goals and objectives as, your main business. 
  • A side hustle can be a hobby, a charitable initiative, a passion project, or a seed that you can eventually grow into your main hustle or main area of income. 
  • Having a side hustle can be the mechanism that transitions you out of that main industry, or an insurance policy against you losing your job or being forced out of employment.

[20:31] – The five most common mistakes that baby boomers make when they're starting a business.

  • Mistake number one is not testing your new career first. 
  • Number two is not managing expectations.
  • Number three is not knowing what matters most. 
  • Number four is not seeking training first, like that one. 
  • Number five is not having a plan B. 
  • All of these mistakes can be mitigated by having a side hustle: it helps you test the marketplace, get a good idea of your performance and earnings, look at long-term survival, have time to learn and experience unfamiliar paths, and develop your skills.

Resources

Baby Boomers have been trained from the time they were born to fight failure. As children we were punished, sometimes severely for failing, it has been anathema to our generation.

Failing is not such a bad thing in many Millennials opinion.

“If you aren't failing you aren't trying”

They believe we learn from failure and it is a natural part of our journey. Even to the point of encouraging each other to embrace failure as a step forward, a positive outcome, necessary to reach our goals.

Heady stuff! And for many of my generation, passing strange.

But there is wisdom here, real value, I am entranced by the concept of “Failing Forward”

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