How To Successfully Fail In Business

When it comes to failing, what if you chose to embrace the experiment?

Posted Apr 02, 2018

Photo by chuttersnap on Unsplash
Source: Photo by chuttersnap on Unsplash

Katherine Minshew pitched her career development website to over 100 investors, and she received 148 rejections. In one interview, she says she had a “no” for breakfast and a “no” for lunch.

Yet she persisted.

In 2016, she raised over $16 million. Her website, The Muse, now serves over 50 million people.

Sometimes the “no”s in our professional lives are opportunities, but we’ll never experience them if we cling to our fear of failure.

Atichyphobia, or fear of failing, is a serious professional fear that can plague even the most confident, competent of people.

According to Theo Tsaousides, Ph.D., author of Brainblocks: Overcoming the 7 Hidden Barriers to Success, in his article ‘Why Fear of Failure Can Keep You Stuck’ (2007), the root of this fear comes from:

the emotional, cognitive, and behavioral reaction to the negative consequences you anticipate for failing to achieve a goal.  It is the intense worry, the negative thinking, and the reluctance to take action you experience, when you imagine all the horrible things that could happen if you failed to achieve a goal.

The active attempt to avoid the hypothetical bad-feeling is your brain’s way of cutting yourself off at the pass. This debilitating habit is all too easy to fall into, particularly when the personal investment is so high.

Take Michael, who fantasizes about leaping from his job and becoming a speaker on a subject he knows quite a bit about. What he doesn’t know anything about is public speaking. What if he got in front of an audience of New York business executives and flopped on his face? What if he were actually invited to a conference and froze in front of 5,000 people? What if he left his job and failed in front of his friends? So he decides that, equipped with all of those fears, it’s best that he never try.

He keeps himself safe.

This fear of failing is dressed up like a kind of perfectionism. By convincing himself that perfection – in this case, knowing everything before he gets started – is the only way to make a difference, he’s stopped before he can be ‘proven wrong’.

He’s also stopped himself from doing anything at all. What else could he have done instead of letting fear of failure paralyze him?

There is a way to fail “successfully” in business. It shifts the understandable psychology of fear into useful action. This shift from fear to useful action is corroborated by new studies on the value of experimentation and prototyping.

Failure, or Data Gathering?

Like anybody who has dared to build a successful career, I’ve experienced “failure” in my professional and creative life. I’ve produced work only to have it rejected. Launches have fallen short of the mark, or talks I’ve given haven’t reached their target. I’ve even worked extensively on big ideas for months, only to recognize that it was time to pull the plug.

Yet I consider none of those efforts failures.

Instead, I’ve used these efforts as an opportunity to gather data. I’ve recognized that the power of the work is in the act of doing the work, and I’ve improved myself and my workflow. After all, you might find a thousand directions that don’t work for you, but you’ll be able to take much of the knowledge that you’ve gathered when you find the path that leads where you want to go.

What matters is being able to delineate the reasons we’ve failed, and instead of taking the rejection personally, making it useful. If it isn’t useful, then it has to be left behind.

Enter the prototyping mindset.

Mindsets: Personal Prototyping & Entrepreneurial Experimentation

Prototyping as concept and advantage has been studied at least since the 1980s in the computer user field. With the advent of CAD (computer-assisted design), designers could create manufacturing models for aerospace and automotive industries. Those models let engineers troubleshoot potential problems before going to the high expense of actual production and then discover fatal flaws in the design of parts.

Yet prototyping has become a staple for anyone - entrepreneur, agile creative, accomplished professional - who wants to advance her best ideas in the world.

Norris F. Krueger, Jr. argues in ‘What Lies Beneath? The Experiential Essence of Entrepreneurial Thinking’ (2007) that “entrepreneurs are made, not born.” His study concludes that emerging entrepreneurs must form role identity formation and begin perceiving themselves as entrepreneurs in order to advance, eventually, toward an expert or master. An integral part of thinking like an entrepreneur, Krueger argues, is learning a problem-solving skill set.

The following is our variation at Tracking Wonder, based on the classic model as defined in The Art of Thought (Wallas, 1926). Imagine the creative problem-solving process looking like an iterative, cyclical (not linear) process that more accurately reflects the ways in which agile creatives work through their creative and entrepreneurial challenges.

Identify the Problem

  • Intentional Preparation (or what our consultancy calls “Priming the Mind”): Gather your information. Analyze it. Tap previous ways you solved similar problems.
  • Deliberate Incubation: A time to divert your focused attention. Mind-wander. Explore. Daydream. “Sleep on it.”

  • Eureka Insight: You get the idea. However, this often either happens during incubation when you’re not focused directly on the problem or while actively working. In other words, quite often just priming your mind consistently will train your mind to watch for insight.

Assessment, Action, and Execution

In the creative problem-solving process, what entrepreneurship and design thinking have added is prototyping. This is a critical part of the Assessment stage. In order to get feedback on the value and viability of an idea, you want to build in time for low-scale tests.

Before you launch a big program, test it out on a few colleagues behind the scenes. Before you run a big-pay retreat, run a retreat with a few friends. Before you launch a whole new website-based business model (e.g., Zappo’s), create a prototype website to see if people actually enjoy and will use the website-based business.

This is the crucial stage of data-gathering. Sometimes your experiment works just as you planned. In most cases, every creative and entrepreneurial experiment requires refinement.

Did one of your efforts bomb? Assume the reframe posited by Dr Tina Seelig, In her book Ingenius: a crash course in creativity (2015): Failure equals data-gathering.

Self-Inquiry as a Foil for Failure

After a lot of data-gathering, it’s possible to feel frustration, bitterness, or cynicism. I’ve found that my own high standards and expectations act like a trap. Particularly for mission-oriented businesses, it’s easy to fall into the idea that our valuable work is worthy of support and business.

Which may well be true, but it’s important to keep challenging your own expectations. Self-Inquiry is essential to make sure that what you think you’re doing and what you’re actually doing are aligned.

The questions of self-inquiry come in three phases. First is when you’re examining your offering - be it a creative project, new course, startup idea, or new business offering. If you feel like you’re suffering from a shortage of appreciation for your work, ask yourself the following:

  • Have I earned this expectation?
  • What part of what I am offering is valuable to others? How have I learned or validated this information?
  • Am I offering something that earns me the right to ask something of someone else?

The self-inquiry doesn’t stop there, but turns toward necessary skill development.

  • Have I learned the skills necessary to communicate its importance and value?
  • Do I have the skills to create something that will captivate my audience and enlist them to actively engage?

Finally, the most vital of the questions.

  • Am I enjoying the skills I’m learning?

If the answer to any of these questions is no, then you have the opportunity to develop a new roadmap to address them. While it can seem easy to turn inwards, lick our wounded ego, and not continue when staring at too much gathered data and not enough victory, perhaps the greatest way to control the fear of failure is, in the words of Samuel Beckett, “Ever tried. Ever failed. No matter. Try Again. Fail again. Fail better.”

Fail More. Fail Wiser.

Leaning into the benefits of data-gathering is what I call Wise Failure. By assuming an intentional, hypothetical, pro-active stance towards the creative work and presence-building, you start to cultivate a scientist’s approach to experimentation. It’s a winning proposition because we’re going to enjoy learning from the experience anyway.

This kind of data-collecting radically differs from “accidental” ad-hoc efforts that more likely lead to attached, wasteful frustration and resentment.

  1. Strategic Learning

    There’s no guarantee that you know how to do any of the things necessary to make your business a success. Rather than letting that stop you from trying, break down the skills you think you need to master.

    Set aside time every week to learn what you don’t know how to do that will get your creative medicine out into the world. Study and break down what other people do. Assess what resonates with who you are and doesn’t. Form genuine relationships with people who can help you – not just to take from them but to give back to them.

    If you are only taking expertise from a person, then you might expect to pay for it – especially if you have no pre-existing relationship with that person and you’re in turn expecting people to pay for what you create and offer. It is an investment in your continuing education as a mid-life creative.
  2. Learn the Give & Take

    Because creative-minded people are accustomed to floundering with money, many of them feel as if they’ve been generous enough with their time and creations and that now is their time to earn more back. But there’s an art to bring out our natural generosity, of giving – sometimes for free – what we do for people who could otherwise support us.

    Find ways you can naturally be generous and giving before asking and taking. It’s a matter of wise give & take. Adam Grant – yet another under-40 Wharton School professor publishing provocative books – crystallized what I’ve been exploring in his thought-provoking leader book Give and Take: A Revolutionary Approach to Success (2014).

    Building on the classic paper ‘Interpersonal attraction in exchange and communal relationships’ (Clark and Mills, 1979), Grant adapted the claim that many relationships can be defined by how they treat the giving and taking of benefits. While Clark and Mills saw interpersonal relationships as either exchange relationships or communal relationships, Grant turned his focus to relationships in the workplace.

    In Give and Take, Grant offers convincing evidence of the factors that motivate and contribute to how people give in wise ways – without being manipulative. This way of giving is not reciprocity (expecting a tit-for-tat balance of give & take). This latter point is why I call this kind of giving “natural generosity.” Successful teachers, engineers, entrepreneurs, and others who give successfully – or, I would say, wisely – keep in tact a healthy self-interest while being generous.  Grant calls them “Other Givers” versus the selfish Takers or self-sacrificing Givers.
  3. Think like a creative. Experiment like a scientist.

    An ambitious writer gave me an update recently to say that she had “failed” at meeting her writing goal this month. I suggested she treat her writing practice like an experiment. Make an hypothesis: “If I do X for X number of hours/days, then Y will result.”

    The same mindset applies to building your presence in the world. Actually, work with reasonable goals – even if you’re not goal-oriented. Test out your efforts. See what lands and what doesn’t. There’s a lot more to building your presence as a creative than these four points. Knowing how to leverage your native modes of captivating and elevating other people, for instance. Knowing what the Story is that you or your project are about and co-creating with your audiences.

    Treat it like a wise creative endeavor itself. Create an experimental environment.

The Power of Prototyping

Prototyping is the essential tool to challenge the paralysis of fear.

To thrive, high-performing creatives surround themselves with people who are forgiving of error, clear in feedback, and agile enough to change course.

If you're a business of one, cultivate more self-compassion. If you work with other people, talk about your mutual understanding of being able to take risks, make mistakes, and move on.

When you look back on your year of wise work, you want to see yourself at your best and say, with confidence, “You’ve come a long way, baby.”

And that long way rarely happens by accident. It’s a look in the mirror with a tad of admiration, maybe astonishment.


Clark, M. S., & Mills, J. (1979). Interpersonal attraction in exchange and communal relationships. Journal of Personality and Social Psychology, 37(1), 12-24.

Grant, A. M. (2014). Give and take: A revolutionary approach to success. London: Phoenix / Orion Books.

Krueger, N. F. (2007). What Lies Beneath? The Experiential Essence of Entrepreneurial Thinking. Entrepreneurship Theory and Practice, 31(1), 123-138. doi:10.1111/j.1540-6520.2007.00166.

Seelig, T. L. (2015). InGenius: A crash course on creativity. New York: HarperOne.

Wallas, G. (2014). Art of thought. Kent, England: Solis Press.

Tsaousides, T. (2017) Why Fear of Failure Can Keep You Stuck. Retrieved from