Successfully Failing and Personality Types

Darrell’s avatar

Who wants to fail?

The answer to this question might surprise you. Many successful people not only expect failure, but embrace it. As Winston Churchill said, “Success is stumbling from failure to failure with no loss of enthusiasm.” And as comedian Chris Harwick put it, “No human ever became interesting by not failing.”

Yes, failure can hurt. It can damage our reputations and weaken our resolve. But when it creeps into our lives, failure can also provide us with many invaluable lessons. It can strengthen our resilience, teach us what doesn’t work, and give us the experience or leverage we need to make our next endeavor a success.

Our relationship to failure is a reflection of who we are and how we face the world. How easily are we deterred when things don’t go our way? If an idea for a project fascinates us but has a slim chance of success, do we go after it or do nothing?

There are no correct answers to these questions, but some perspectives are more constructive than others. When failure knocks at our door, we can choose whether the experience will harm our self-esteem or strengthen our resolve. And fear of failure, if left unchecked, can keep us from taking the risks that enable us to do something rather than nothing. Unless we view failure from a healthy perspective, we may fall prey to a state of learned helplessness that can lead to ennui, emotional stagnation, or even depression.

If we want to grow and develop over the course of our lives, learning to move on from failure is essential. Everyone falls short at one point or another, and this doesn’t have to be a bad thing. Trial and error can be an excellent way to learn and progress, and many people would argue that failure actually paves the way for a full, successful life.

So how do various personality types behave when they don’t succeed, and how can we use this knowledge to develop a healthy, productive relationship with failure? Below, we’ll explore a few trait dyads to see what they can teach us about taking necessary risks and recovering from disappointment.

Assertive vs. Turbulent

As you might expect, Assertive people – who tend to be confident, self-assured, and easygoing – are more at ease with the prospect of failure than their Turbulent counterparts. Turbulent people are often plagued by self-doubt, and they are acutely sensitive to failure, criticism, or even perceived failure. Their perfectionism leads them to set high standards for themselves, and these personality types may be dissatisfied with their performance even when they’ve done well.

Sure, Assertive people may feel bad about a failure, but they probably won’t let it do permanent damage to their sense of personal worth. Turbulent personality types, alas, tend to see failure as evidence of their inadequacy or unworthiness, and they may even experience deep shame when things don’t go their way. If they constantly work to compensate for their perceived shortcomings, Turbulent people are living in reaction to failure rather than charting the lives they truly want for themselves.

To break free of this pattern, Turbulent personality types need to separate their failure from their personal identity. Our successes and our failures do not change who we truly are, and if we take them personally, we are reducing our self-image to a tiny slice of our true identity. In addition, both Turbulent and Assertive types can benefit by looking for the silver linings in their failures: what lessons did they learn, and how can they carry these insights into their future endeavors?

Of course, there is one upside to expecting failure. Because they tend to envision worst-case scenarios, Turbulent types are motivated to prepare, learn, and practice their skills before they take on a project. As long as they don’t procrastinate indefinitely, this degree of preparation can – paradoxically – boost their chances of success. By contrast, Assertive personalities might spend less time preparing for their endeavors, which can prevent them from doing their best.

Extraverted vs. Introverted

How you handle failure will also depend on your degree of Introversion or Extraversion. Because Extraverts tend to have more extensive networks than Introverts, they are in a better position to ask for support and assistance when things go south. Extraverted personality types may also be more likely to seek reassurance from others, which can help them bounce back from failure.

There are some downsides to this approach, however. Extraverts can fall into a pattern of bemoaning their failures to others, revisiting them time and again. They may find themselves standing around a water cooler, “awfulizing” a failure with a group of kindred spirits. This type of exchange can be helpful in the immediate aftermath of a disappointment, but in the long run, it can prevent Extraverted personalities from fully moving on – particularly if they’ve shared their weaknesses with people who will rehash them in the future.

Introverts, on the other hand, may expect themselves to process failure entirely on their own. On the plus side, this approach can build self-sufficiency and prompt deep reflection. It can also isolate Introverts, however, preventing them from reaching out to people who would help them. Introverted personality types may need to balance their self-reliant tendencies with a willingness to call on other people when necessary.

Intuitive vs. Observant

Intuitive personality types – especially those in the Diplomat Role – may let their fear of failure prevent them from trying new things and pursuing their dreams. Relentless visionaries, they have a clear picture in their minds of what they’d like to achieve. Unfortunately, this vision can be so shining and perfect that falling short seems inevitable.

Moreover, Diplomat personality types are more likely than any other Role to say that minor failures lower their self-confidence. The result: they’re at risk of second-guessing themselves indefinitely, never taking action on their ideas. Analysts can also fall into this trap, as their Intuitive trait enables them to picture ideal future outcomes that may or may not be achievable.

Sentinels and Explorers – who share the Observant trait – are less likely to be hamstrung by the fear of failure. Practical and efficient, these personality types view failure as a mandate to take action and do whatever is necessary to move on. Because Sentinels and Explorers live in the present moment, they tend not to dwell on past shortcomings or future worries.

This doesn’t mean that they never fear failure, only that they are able to respond proactively and constructively to such fears. As a result, these personalities are less likely than their Intuitive cousins to let failure paralyze them.

Paradoxically, in the wake of repeated failure, Analysts and Diplomats are less likely to abandon their major goals than Sentinels or Explorers. Because their objectives are typically visionary and abstract, Analysts and Diplomats are well poised to adapt to changing circumstances, and their idealism may prevent these personality types from giving up, even when the evidence doesn’t seem to be in their favor.

On the other hand, Sentinels and Explorers may interpret repeated failure as “beating a dead horse,” which would lead their practical natures to move on in search of a new pursuit.


As you analyze your relationship with failure, you’ll notice two major considerations: to what extent are you limited by your fear of failure, and to what extent are past failures holding you back?

In an ideal world, you’d have just enough fear of failure to prepare well for your endeavors, but not so much that you’d never take action. And you would view past failures as learning opportunities, moving on when appropriate but not giving up too soon.

An awareness of personality types and traits can help you optimize your view of failure and your response to it. If you’re Turbulent, you may need to encourage yourself to take risks in the name of your goals and passions. If you’re Assertive, you may need to spend more time preparing for your endeavors.

If you’re Extraverted, you may need to make sure that you’re not dwelling on past mistakes in conversations with friends or colleagues, and if you’re Introverted, you may need to allow yourself to call on others more often. If you’re Intuitive, you may need to allow yourself to pursue the vision in your head, even if the results will be imperfect, and if you’re Observant, you may need to check that you don’t abandon your endeavors the moment they seem impractical.

Whatever your personality type, failure doesn’t have to herald the end of your hopes and dreams. Instead, failure can present you with a unique opportunity to learn, reflect, and grow into the person you most want to be.