Becoming Wise Through Looking Foolish

Admitting that you don’t know something is honest, brave and often the best option. Why we should risk looking foolish more often.

‘The man who asks a question is a fool for a minute, the man who does not ask is a fool for life.’


In general we enjoy learning new things and feeling wiser. But at the same time, we often find it hard to admit that we don’t know something. We prefer to hide our ignorance rather than risk looking foolish.

However, by hiding our ignorance and avoiding asking questions we miss the opportunity to learn and grow, as well as to better connect with the people we care about. Here’s how we can learn to take more risks in our professional and personal lives.

The Temptation To Avoid Looking Foolish

We’re going to start in the workplace, because it’s a great example of human interaction in groups.

I’m going to use my experience from the world of finance (in particular investment banking). For those who unfamiliar with this world, let me paint you a brief picture:

The world of investment banking:

  • Men (and some women) in suits meeting VIPs to discuss Important Finance Transactions.
    NB: in finance-speak a VIP generally means a Chief Finance Officer, not a film star or Enrique Iglesias unfortunately.
  • Excel spreadsheets of complex NASA-level financial analysis, summarized in Powerpoint presentations of 200+ slides.
  • Late nights and early mornings.
  • Thousands of (unread) emails.
  • Conference calls on weekends – where possible done at home in your pajamas (hoping your boss can’t hear the neighbour’s newborn crying).
  • Eating lunch and dinner at your desk reading the ‘Wall Street Journal’ online. Also secretly reading a gossip magazine like ‘People’ in a smaller browser window. And dropping crumbs all over your keyboard.

Now you have a visual of the backdrop (and are perhaps wondering how you overlooked finance as a career choice), let’s talk about the fear of looking foolish in the workplace.

The fear of looking foolish

There can be a reluctance in a workplace setting to admit “I don’t know” because of the fear that this will be interpreted as saying “I am an incompetent fool who does not deserve this job. I should go pack my desk items into a box and take my sorry self home.”

Now to be fair, we should know our field of expertise. It would not look good if the client asks ‘Thank you for the *yawn* 200 slide presentation. So should we go ahead and buy this company at $XXMM?‘ and the Managing Director were to respond with ‘Errr.. I have no idea. What do you think?’.

He really should go pack his things into a box and take his sorry self home.

I am not talking about the times when you really should know the answer (as in, it’s your job to know). I am referring to the times when you genuinely don’t know something but are reluctant to ask.

Am I the only one that’s confused?

At times we are afraid to admit ignorance in a group setting because we assume (often wrongly) that we are the only ones who are confused.

This can be illustrated in the corporate world in meetings. For example, I can recall brainstorming sessions where everyone was excited by the new ideas and nodding enthusiastically. But as the meeting is concluding, I’m sitting there confused and wondering ‘But what did we decide in the end?! Why am I the only one confused?’.

However, whenever anyone in a meeting had the courage to say ‘Sorry but I’m confused. Please clarify‘, it would often turn out that many of us weren’t sure. It was just that people felt foolish saying, ‘It sounded reeeally great boss, but umm… eerrr… what do you mean exactly?

We each assumed that we were the only one confused and that everyone else understood what was going on (in psychology this is referred to as pluralistic ignorance). Likewise our boss thought we understood because no-one was asking questions.

The pressure of being in groups can increase the temptation to remain in ignorance, rather than risk looking foolish by asking questions.

The problem with being afraid to admit your confusion is that you (and everyone else) remain in ignorance. The only way to get more clarification is to ask for it. Further, asking earlier is better. It is easier to ask for clarification on something said earlier today, than to admit to your boss that you’ve been confused about a project for the last 6 months

As I gained experience I found I preferred to ask questions and risk looking foolish rather than suffer the agony of being in confusion. I also discovered that asking questions was viewed positivity, as showing curiosity and initiative. I was fortunate to work in environments where asking questions was encouraged and over time it became a habit.

How admitting ignorance creates trust

In investment finance we spent a lot of time analysing the risks and benefits of investments in companies. For the more serious investment opportunities, we would engage in ‘due diligence’.

‘Due diligence’ is investigating the risks, benefits and costs of a potential investment. For example, when you become serious about buying a house and instead of admiring the open-plan living space and marble benchtops, you start eying the walls for signs of termites and mould.

A large part of our due diligence involved asking questions. If management of the company we were analyzing did not know the response to a particular question, they would generally ask for more time. This was a normal part of the process – admitting ignorance was not seen negatively.

By contrast, if management had instead tried to cover up their ignorance (or even worse lied), this would have raised some serious doubts, not just in relation to the question we had asked, but to the integrity of the team.

If someone admits when they don’t know something, you have more confidence when they tell you what they do know. By contrast, covering up or lying about ignorance can lead to decisions based on bad information and destroy trust.

Making Asking a Habit

‘The only true wisdom is in knowing that you know nothing.’


Asking questions and admitting ignorance is useful in all aspects in life, both professional and personal. It’s the way we learn and growth.

And I don’t mean when you FINALLY admit you’re don’t actually have a built-in GPS in your head and need to ask for directions.

Learning to admit ‘I don’t know’ applies to situations when we are too embarrassed or proud to ask because we think you should already know. We also need to learn to recognize when we’re simply making assumptions, rather than asking to find the real answer.

For example:

  • Have you asked your partner lately what s/he considers romantic or wants in the bedroom (you might be surprised)?
  • Do you know what your best friend or kid’s biggest worry is, or are you just assuming you know?
  • When you have to make a big decision (job, relationship), do you admit what you don’t know and ask for advice?
  • If a decision you’ve already made isn’t working out, are you open to considering that you might be misinterpreting something or missing some helpful information?
  • How often do you question your key underlying beliefs, particularly the ones that limit your growth? Do you question the excuses you make for not trying new things?

The openness to admitting that (i) you might not know something or (ii) something that you assume you know may not be correct, brings opportunities for learning and growth. It also leads to better understanding the people that matter to you.

Becoming Wise Through Looking Foolish

Admitting that we don’t know something can be hard. It takes vulnerability and therefore courage. It means moving out of the comfort zone of certainty into the territory of the unknown.

But one thing I have observed is that asking questions is something that you can get better at. You can learn to cultivate an attitude of humility and open curiority. When faced with uncertainty, instead of rushing to defend yourself or hide your ignorance, you choose to see it as an opportunity to learn and grow.

The people that I have observed as being really good at asking a lot of questions are some of the wisest people I know.

So be courageous – risk looking foolish in order to become wise.

‘The greatest gift is not being afraid to question.’

Ruby Dee

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