One of my coaching clients had recently experienced a string of failures. A business venture that had consumed a great deal of her time flopped. A new line of business she was attempting to market was finding little response in the marketplace. Several of her long-time clients stopped working with her.


She woke up one morning feeling depressed. If her business was failing, perhaps she was a failure as a person. Maybe she needed to give up her business and get a job. Or find a different kind of business to be in. She was feeling lost, stuck, and discouraged.

Seeking inspiration, she ran across this quote, often attributed to Winston Churchill: “Success consists of going from failure to failure without loss of enthusiasm.” She emailed it to me before our next coaching session. “I think there’s an idea there that could help me out of this funk,” she said. “Can you help me see what it is?”

We spent an hour together examining her current situation and what had brought her there. I asked her about the quote and what she thought it meant. “How would things be different for you,” I queried, “if you believed this quote were true?”

By the end of our session, her mindset had shifted. She recognized that her recent failures had a great deal to teach her, and that this learning could become a new source of enthusiasm for her business. Here are some of the things my client and I determined that a self-employed professional or creative can learn from failure:

1. What caused you to fail?

Sometimes we’re afraid to ask ourselves this question. Perhaps you fear you will discover something unpleasant about yourself. This fear may be completely unfounded. Your failure may have been caused by circumstances that were beyond your control, or an event that couldn’t have been predicted. If you discover that you failed due to no fault of your own, you may quickly regain your enthusiasm to try again.

If you did cause the failure in some way, determining what you did wrong may be the only way to figure out how to do it right. If you avoid examining your failure, you will be far more likely to repeat it. So even if it’s uncomfortable, take some time to look at exactly what happened, and why.

2. What’s one thing that could make a difference?

Sometimes a simple change in your approach can make the difference between failure and success. My client realized that she had been guilty of Lone Ranger syndrome, implementing plans without asking anyone else for input. When she began asking others what they thought about her new line of business, she quickly discovered what had been missing from her marketing messages, and began to see some response.

3. Failure teaches you what doesn’t work.

This is no small thing. Trying to make a business succeed is often like arriving at a crossroads with a dozen different paths in front of you and no road signs. The only way to choose the correct path may be to travel down several wrong ones first. It may seem like these are false steps, but actually they represent progress.

Every time you take action and don’t get the results you want, you learn more about which actions to avoid. Eliminating the unsuitable choices makes it much easier to identify the appropriate course. It may seem inefficient, but taking steps in the wrong direction is much more productive than just standing at the crossroads wondering which way to go.

4. Failure teaches you what makes you unhappy.

It’s a curious aspect of human nature that we often find stronger motivation in negative emotions than in positive ones. If your failure makes you sad, angry, or frustrated, this can be just the kick in the pants you need to head in the opposite direction.

If losing a prospective client to a competitor makes you angry, it’s a powerful impetus to work on improving how you communicate your competitive advantage. When you become frustrated by the lack of referrals from your current network, it may be the nudge you need to start making new contacts. Dissatisfaction with your business can make you realize you need to reinvent the whole thing. Learning what makes you unhappy can teach you a lot about where happiness lies.

5. How much do you want to succeed?

Setbacks can make you realize how strong your desire for success is, and what you’re willing to do to get it. My client discovered that her wish for a thriving business was more powerful than her dislike of asking other people for their opinion. She found a new level of motivation for becoming a savvy businessperson, willing to step outside her comfort zone when it would serve her desired success.


We all fail at times. The key to success is not avoiding failure; it’s grasping how to learn as much as you can from it so you can try again. It may seem as if successful people are lucky, but more often, they are persistent. The real failure is when you give up because your first attempt — or your second, or your third — doesn’t succeed.

This post was first published in 2019 and has been updated for 2024.

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