The Intersection of Overconfidence and Self-Doubt

I remember the first nice camera I purchased. It was 2010, and our first child was on the way. Growing up, I had always enjoyed taking pictures, so I thought this would be the perfect excuse to upgrade to a real camera – a DSLR. 

I remember getting it out of the box, a Canon Rebel T2i. I was in awe of the sleek black frame. The interchangeable lens. The weight of it in my hands.

While my wife was eight months along, her pregnant sister was just ahead of her, expecting their third child any day. When the day came and our newest niece was born, we went to the hospital to celebrate. With my new camera in tow, I was excited to document the happy occasion.

Our new baby niece was so peaceful, and her older sisters were fascinated by her. They cuddled up in the hospital bed to meet their sister. I was standing by, camera in hand, and shooting away. 

Then it happened. Just as the sisters were getting to know their new baby sis, she yawned. Snap. I knew I had a good one.

Above: My nieces meeting their baby sister for the first time. As a budding photographer, this was my first glimpse of the joy of capturing a special moment for someone else.

What a moment! I felt so happy that I had captured this special moment for my in-laws, and I was proud of myself. Clearly, this new gear had uncovered my photographic talent. I was supremely confident – I was an amazing photographer!

Fast forward just a couple of months. As I continued to photograph, I started to get frustrated. I would see something beautiful or interesting with my naked eye, and then when I tried to capture it in-camera, it didn’t look the same. Perhaps the light was too bright, or too dark, or the subject was moving too fast. It was a frustrating experience – I saw something in my mind's eye, but I couldn’t recreate it in reality. I started to wonder what the different settings were on the camera. What were things like aperture, shutter speed, and ISO, and would knowing what they were help me to capture better images?

The frustrations mounted. The more I learned about photography, the more books I read, the more I realized I really had no clue. That first photograph was a lucky moment in time – a happy accident. The subject, the lighting, the framing – everything came together in one magical moment, and despite my inexperience, I didn’t screw it up. The camera happened to pick the correct settings at that moment. 

But if I wanted to be able to capture more of those magical moments, I had a lot of learning to do. 

Have you ever noticed that the more you learn about something, the less you realize you actually know? That the deeper you go down the rabbit hole, the deeper the rabbit hole gets?

This phenomenon of early overconfidence, followed by self-doubt, and eventually by mastery and humility has been studied, and it has a name – The Dunning-Kruger Effect:

Above: The Dunning-Kruger Effect describes the relationship between confidence and competence. The more you know, the more you realize you don't know (link).

The principle at play here is that we underestimate the depth of a topic or discipline early on. The dominant assumption is, “Yeah, I pretty much get it.” 

This naivete leads to an inflated sense of confidence, even though competence is low. Because they don’t know they don’t know, they assume they have some level of mastery.

As the individual learns more, the more competent they become, which is when feelings of despair set in. 

Do I even know what I’m talking about? Experts call this the valley of despair… I’ll never understand this!

But self-doubt is on the path to self-confidence. 

The Dip

Seth Godin wrote about this concept in a book called The Dip. The subtitle says it all – “A Little Book That Teaches You When to Quit (and When to Stick).” 

He describes the Dunning-Kruger effect as a journey, using learning to ski as an example. It can be fun to wedge your skis down the bunny slope early on. But inevitably, as one progresses and starts to learn real ski techniques, it gets really hard. 

Many people never make it out of the dip – they quit when it gets hard. But for those who push through the dip, the reward on the other side is the joy that comes with competence and mastery. (And I would add, hopefully, a healthy dose of humility because one understands how hard it is).

The principle is that anything worth learning in life is going to have a dip – a point in time when you know enough to have a sense of how much you truly you don’t know. That is where self-doubt comes in. 

I faced the dip many times while writing my new book, The Rise of Sustainable Giving. About a year into the process, I was doubting myself. Who am I to write this book? What if I’m wrong about some of the lessons in it and mislead people? How will I ever know enough?

After a conversation with Peter Greer, author of more than a dozen books, he helped me to realize that I will always be learning – and that’s a good thing. But at the same time, I had enough of what I needed to start the writing journey. The following two years of research and writing were pushing through my own personal dip of understanding and mastering Sustainable Giving. 

I know more than I ever have about sustainable giving, but I’m also more aware than I have ever been of how deep this rabbit hole goes, which gives me humility. I don’t assume I know everything about sustainable giving, so when I meet people, I can continue to have a learning attitude. 

Godin points to another lesson we can learn from the valley of despair – that not everything is worth pushing through the dip. He says the smartest leaders know when to stick, and when to quit. They know that to master anything is going to get hard – and they ask the question – “Am I going to be willing to push through the dip on this?” If the answer is “No,” they quit early or don’t even try, reserving their energy for areas where they will persevere. 

💡 Takeaway: Those who stick with a subject long enough to achieve mastery rise up the other side of the dip. They will never be quite as sure of what they know as they were early in their journey, but that’s due to maturity because they know, after all, “It’s complicated.”

Let’s close with three lessons we can apply from the dip.

Lesson #1: Assume every field is a deep rabbit hole.

I’m continually reminded of this when I meet people who work in fields that are new to me. Or co-workers who have other roles in our industry. It’s easy to assume “My job is hard and complex and nuanced, but theirs, it’s pretty simple, really.” 

Today, I default to assuming deep expertise is required for anyone who is successful in any field, and I treat them with the respect and curiosity that will help me get a glimpse into their deep expertise. 

💡 Takeaway: Treat others with the same level of respect you would hope to have for what it’s taken to get good at what you do.

Lesson #2: Know that it’s going to get worse before it gets better.

When things get hard, I may not like it, but I’m no longer surprised. I’m better prepared for the reality that as I learn anything, it’s going to get harder before it gets easier. As I learn more and move towards competence, there will be frustrations.

As a photographer, I look back at some of my early work and think, “Oh man, that’s not very good.” But that’s because I’ve learned and grown – I wouldn’t have it any other way. 

💡 Takeaway: Going through the dip is a part of the journey, and viewed with perspective, it’s rewarding because it’s where actual growth and competency happens. 

Lesson #3: Anything worth mastering is worth pushing through the dip.

If it’s worth doing, it’s worth getting to the other side of the valley. It’s going to take discipline, but it’ll be worth it. Similarly, if you know you aren’t going to push through the dip, then it is better to quit and focus on another endeavor that you know you will push through. 

Everything has a dip. The question is what will be worth pushing through? This is also a reason to bring in outside experts, because you can’t possibly master every subject and discipline – you don’t have to be the expert.

It’s a reason I love being brought in to help nonprofits grow their recurring giving program. I’ve pushed through that particular dip, and I can bring a tremendous amount of experience and discernment to making the right decisions to drive growth.

💡 Takeaway: Everything has a dip. The question you should ask is if mastery is worth pursuing – if so, push through, learn from doing, and learn from others.

What is an area where you are facing the dip? Is it going to be worth sticking through to the other side? 

As someone who has reached the “other side” of the dip in a few areas of life, I can tell you that the view is beautiful from here!

Until next week… Surfs Up! 🌊

  - Dave

About the Author | Dave Raley

Consultant, speaker, and author Dave Raley is the founder of Imago Consulting, a firm that helps nonprofits and businesses who serve nonprofits create profitable growth through sustainable innovation. He’s the author of the book The Rise of Sustainable Giving: How the Subscription Economy is Transforming Recurring Giving, and What Nonprofits Can Do to Benefit. Dave also writes a weekly innovation and leadership column called The Wave Report, and the co-founder of the Purpose & Profit Podcast — a show about the ideas at the intersection of nonprofit causes and for-profit brands. Connect with Dave on LinkedIn.

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