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We’re told to embrace failure these days or, at least, not be afraid of it. If we want to be successful, we need to fail more.

But it’s not easy to follow that advice. Fear and risk get in the way.

Consultant Bill Wooditch tackles those two bugaboos in his book Fail More. It starts with learning what fears are causing your inertia – the one or two key points. Acknowledging them and exposing yourself to their spectre will reduce the barrier.

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Separate rational from irrational fear. “Rational fear is the early warning system that alerts you to danger. Irrational fear is a product of your imagination. You perceive a ‘threat,’ you project a future harm, and your body reacts in the same way as it does to real danger,” he writes.

We all carry emotional baggage with us – not just our own bad moments but the negative experiences of others we project onto ourselves. But the past won’t guide or determine your future, he insists. Stop fearing things that have already happened.

Be aware of these three signs of your fear: Procrastination, distraction, and rationalization. You tell yourself “I’m not ready,” or “it’s not the right time.” So you avoid acting. But there is no perfect time. You’re probably ready and are deceiving yourself with those justifications.

You can’t succeed, he insists, without failure. “The first condition of success is failure,” he writes. Winning demands accepting failure. At the same time, you don’t want to rush headlong into failure and hold pep rallies when it occurs. You want to only pursue intelligent risks. When you fail, conduct a post-mortem to discover the issues that caused things to go wrong.

In order to take risks intelligently, he says you need to:

  • Be clear – what is the worst thing that can happen if you fail?
  • Be real – can you handle the failure? If not, when might you be able to handle it? Make a commitment to such a time line.
  • Be practical – is there a smaller risk you can take that will provide the momentum and experience you need to later take bigger chances?
  • Be objective – will the emotional or financial pain of failure be greater?

He also urges you to be reflective, keeping a success journal with up-to-date notes on what worked and what didn’t. And this isn’t just for big gambles. “Each day you can learn from what happened the previous day if it’s written down in a straightforward manner. No excuse, no bias – just straight-up facts,” he notes.

Prepare best- and worst-case evaluations before the bigger decisions. Play out your worst-case scenario to determine the ultimate downside you are facing. Ponder the financial and reputational costs, to assess if the risk is worthwhile. Write down the steps you would need to take to mitigate the impact of the worst-case scenario.

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But don’t neglect the upside: What is the best-case scenario you can realize from this risk? Estimate the financial rewards that might flow from taking this course and then reduce it by 20 per cent to keep your expectations under control.

“Failure taught me that I better well know my worst case before I even start to think about my best case,” he stresses. But don’t give in too quickly to those fears. Keep in mind that setbacks can be constructive, a price to pay for greater success.

Quick hits

  • Meetings may seem like a drag but there’s always an opportunity in disguise hiding within the session, Stephanie Fairyington reports for Thrive. Approach meetings as a learning opportunity.
  • Whether your company has a tech policy or not, you can create a policy for yourself – guidelines around how you use technology, how people should interact with you, and when and how you’ll respond to messages.
  • If things go wrong in a job interview, don’t panic. Executive recruiter Gerald Walsh notes you can’t change what happened so stay upbeat and look for an opportunity to explain yourself better after a later question. Or he suggests addressing the issue directly: “I don’t feel I answered your earlier question fully. Let me tell you more…”
  • Sales consultant Colleen Francis says the formula for social media success is to do these three things three times a week on platforms of your own choosing: Share unique, high-value content you created such as a comment, how-to tip or video; share three pieces of content from other sources; and three times a week comment on your customer’s articles or post to let them know you’re paying attention to them.
  • Stop Microsoft Word from capitalizing words automatically by going to Options (on the file tab), clicking Proofing and then the Auto-Correct tab. Expert Allen Wyatt advises you to now clear “the Correct TWo INitial Capitals check box,” the “Capitalize First Letter of Sentences check box,” the “Capitalize Names of Days check box” and the “Automatically Use Suggestions from the Spelling Checker check box.” Finally look through the list of AutoCorrect entries and modify or delete any entries that lead to capitalization of a word.

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