I recently wrote about why being comfortable with failure is one of the best parts of working at Actionable. It’s not like my managers are encouraging me to mess up on a regular basis, but it’s clear that they know I’m a human being (not a robot), and that slip-ups are going to happen from time to time. I don’t think I’m alone in associating the word “failure” with catastrophe—the stuff of nightmares. In reality, “failure,” especially as it pertains to the workplace, is not so dramatic.

For those running consulting and coaching businesses, I understand that the notion of failure can be terrifying—you’re the expert, and your clients are paying you to give them insights into how to avoid mistakes in their own organizations. Why would you want to embrace failure?

Here’s the short answer—you won’t be able to avoid it. Unless you are a robot (and I would commend you for your reading interests if you are), mistakes will be made. Your brilliant marketing strategy doesn’t get the traction you hoped, your client is “underwhelmed” by your deliverables, or the “game changing” client ends up choosing another firm after you poured your heart and soul into a pitch.  

Getting comfortable with the notion of failure means that whenever a mistake is made, you won’t feel like the world is crashing down around you. You can pivot your marketing strategy, respond graciously to bad news, fix the problem, and move on.

I have curated a list of three summaries from the Actionable Books community about getting comfortable with failure that can help you navigate these uncomfortable circumstances as they arise.



Fail Better
Anjali Sastry and Kara Penn

Stop thinking about failure as an event, and start to approach it as a learning opportunity. Many of us think of failure as something shameful, to be hidden from those around us. When I make a mistake, my first instinct is to pretend it never happened, sweep it under the rug, tell no one, and get bright red if it ever comes up. I am learning to fight those instincts. The truth is that failure makes for an excellent learning opportunity. If you pretend something didn’t happen, you won’t be able to learn from it. Thinking of failure as a learning opportunity will help you to approach the issue more objectively, and pivot your strategies as required.



How to Fail at Almost Everything and Still Win Big
Scott Adams

This book, from the creator of Dilbert, offers excellent insight into how to harness a failure into something productive. Scott Adams recommends approaching failure as a systems problem, not a moral one. This reframing is very useful: you didn’t fail because you’re a bad person, or because you’re unqualified for the job, it more likely has to do with a failure in the system that you depend on. It’s not personal, so it’s easier to look at objectively, and move on from. When a project doesn’t go as planned, look to the systems that support it. Maybe making some changes to your CRM system, or providing clarity around communication strategies, will address the issue.



Jamie Notter and Maddie Grant

Although the specifics of this book focus on digital communications, the central premise—that people need to be treated as human beings—is crucial. Treating your clients as a line item in your revenue projections won’t yield sustainable results. It feels strange to have to say it, but your employees, partners, clients, and support staff are all human beings. They are messy, complicated, and imperfect. They are going to mess up, and so are you. The first step to making sure that these failures don’t negatively impact your business is to accept them as inevitable. Despite our best intentions, people are imperfect. Embrace that as a contingency in your planning, and you won’t get blindsided by disruptions.


Reviewing these summaries has been a great reminder for me to extend the same kindness to myself that I extend to others. I’m going to mess up, but I can also learn from my mistakes. When those around me fail, I can empathize, and try to help them through.

You, and everyone you work with, are human. Failure (in some capacity), is unavoidable. Will you embrace it? Learn from it? Or will you try to pretend it never happened?