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Arrogance, Confidence, and Insecurity

“The moment you think of yourself as great, your slide toward mediocrity will have already begun,” Jim Collins.
“Wisest is he who knows what he doesn’t know.” Plato

I read these quotes the other day and I really like them both. I think mainly because it is an interesting time for my career as for the last year I’ve been put in new situations almost every day. As such, this can leads to time to insecurity and confusion. I guess I’ve moved out of my work “teenage” years where I knew it all and thought I was smarter than my bosses. That’s definitely not even close to being true these days.

When you are put in these new situations, it is tricky on how to play it.

Do you pretend you know what you are doing when you don’t? Fake it until you make it.
Do you admit your insecurity and confess your inexperience in the task at hand?
Or do you try for somewhere in the middle? Act confidently but still ask questions?

In life, you are constantly trying and learning new things. I think it is important in how you approach learning new things. Nobody likes the person who is complete insecure and reminds you on how bad they are at the task at hand. However, the opposite is just as bad – the person who thinks they are a genius and have everything figured out even though they have never attempted the task at hand.

Lately, I’ve been trying a middle road. Acting confidently at the task at hand. However, I also try to find the experts of the task and get their advice on the side. A little flattery, curiosity, and (sometimes) chocolate can go along way. And I notice I can usually figure out the task and am ready the second time around.

As one of my mentors said when I was discussing this year, “X has 25 years of experience working on Y. Really, that is one year of experience repeated 24 times. You’ll have just as much knowledge about Y in one year.” I’m just trying to get one year of experience on a lot of new areas.

How do you handle new tasks at hand? How do you deal with the arrogant, the confident, and insecure?

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Michael O. Johnston

Great Blog,

Although I am new to the nonprofit sector, and have yet to be exposed to the public sector (I hope to be exposed to such in the future), but as I am being trained in my new position I am having the same feeling which you have mentioned that one of your mentors told you in a discussion, “X has 25 years of experience working on Y. Really, that is one year of experience repeated 24 times. You’ll have just as much knowledge about Y in one year”.

A great example I believe of this is after only two days of training my trainer put in her notice because she got a job offer that was less of a drive for her from her new house, and have now taken on the role of Health and Safety Coordinator and have to speak during staff meetings and evaluate our location for potential health and safety hazards. Another example would be within only a week of training in my position I have also already trained another person in set-up at a secondary location of the Afterschool Program that work for.

This is not to say that I have all the knowledge needed for Y after only being trained for a little over a week, but what knowledge I have gained has been maintained, and to go even further with this I would like to say that I hope that over years to come in my profession I hope there is not a day that goes by that I don’t learn something new each day and/or further my knowledge on items that I already have some knowledge on.

Lastly, to answer your question on how I handle new tasks at hand. At my new job I have become responsible for several new tasks in a very short amount of time, which were all commented on in the previous statements. I handle such by using a median somewhere between confidence and insecurity.

What I mean by that is my insecurity is exposed by always not being afraid to ask questions for items which I am unsure of. While my confidence is displayed on items which I have either been trained on and have maintained the knowledge and/or items which I have been trained on in my previous position as a trainer in the food service (i.e. As the Health and Safety Coordinator for the Afterschool Program which I work at many of the items which I am responsible for are very similar to the health and safety rules and guidelines for my previous role as a trainer in the food service industry).

Andrew Krzmarzick

Hi Steve,

About 3 years ago, my former boss gave me a great book called “Radical LEAP” by Steve Farber. One of the memorable elements of the book was the Oh S—! Moment. The OS!M example used in the book is getting on a skateboard on top of a hill in San Francisco, lying on your belly and pushing off! Of course, Farber is not advocating for reckless behavior; rather, he is urging the reader to seek out something they fear and act upon it on a daily basis. Those moments when we experience the greatest fear are precisely when we grow and learn the most. It sounds like you are having several OS!Ms lately. I would highly recommend this book.

P.S. I am actively seeking OS!Ms…like parasailing this past weekend! Nothing like being tied to a boat with a quarter inch cord and a parachute suspending you 400 feet over the ocean below to make you exclaim “Oh Snap!” Check one off my Bucket List.

Engaging in fear-laden activities is also championed by Tim Ferriss in his book “Four Hour Workweek” (which I just finished yesterday). He assigns readers a “Comfort Challenge” at the end of each chapter, like gazing into the eyes of a stranger until s/he breaks contact or attempting to communicate with a celebrity/someone that you think would not respond. Ferriss contends that there is a direct correlation between increasing your “sphere of comfort” and advancing in pursuit of your goals and dreams.

Both of these books encourage the reader to overcome insecurity and fear not just by facing them as a byproduct of what someone else assigns you…but actually looking for activities that cause you consternation! One of my favorite quotes is “Do what you fear and watch it disappear” (Author unknown). Another one is “Courage is being scared to death…and saddling up anyway (John Wayne).”

Now go find yourself a skateboard and a hill… 🙂


I think the key is to be confident about your abilities, not necessarily your knowledge. They are two very different things.

When I am in a new situation, but one I know I can learn if I just am shown the process, I have no trouble asking. I’ve learned that it’s ok to say “I haven’t done this before, will you show me?” It strikes the right balance between insecurity and overconfidence. Only the worst of people would knock you for it or react in a negative way. Most people are happy to see someone confident enough to ask, and they are more willing to help a person like that than a snivelling dweeb or a swaggering jerk (who, of course, didn’t ask for the help but desperately needs it).

Learning that kind of self-confidence can take a while. It all depends on how much you had at the start of your career – and we can all dig into our childhoods for the answers to that one. But once you find the groove, go with it. The truth that we don’t realize as teens is: it’s ok not to know. It doesn’t reflect on us as intelligent people (most of the time). All it shows is that we haven’t encountered a particular situation before.

Sure, there are those people who rightfully should be embarrassed by their lack of knowledge, but chances are they are the swaggering know it alls anyhow. And that’s not any of us, is it?


Thanks. I really like your idea to be confident about your abilities not necessarily your knowledge. I think that’s a good distinction and very helpful.