When Will I Feel Confident Enough to Try?
Updated: Sep 18
TLDR: Confidence doesn’t come from already knowing you’ll succeed. It comes from trusting yourself to learn, adapt, and figure things out along the way. Throughout my life, I’ve discovered that the belief that I can learn something new has given me the courage to take on challenges before I felt fully ready. Whether becoming a coach, managing a home build, or stepping into unfamiliar situations, confidence came before competence. For leaders, this matters because tomorrow’s challenges will always require skills we haven’t mastered yet. The question isn’t whether you know how. It’s whether you trust yourself to learn.
Growing up, I don't remember anyone telling me I couldn't do something. Quite the opposite. Somewhere along the way, my parents gave me the belief that I could figure almost anything out. Looking back, that may have been one of the greatest gifts they ever gave me.
Of course, they weren't literally right. I can't do everything, and life has made that abundantly clear. The first time I tried surfing, I ended up with 14 stitches in my head. Wakeboarding seemed like a great idea until I wrenched my back five minutes after getting a massage that had finally relieved the pain. There are plenty of things I'm simply not good at, and I'm becoming more aware of that list as I get older.
What those experiences never did, though, was convince me to stop trying new things. If anything, they reinforced a belief I've carried most of my life: just because I don't know how to do something today doesn't mean I can't learn.
Learning Is The Catalyst
That mindset has shaped nearly every major decision I've made. When I decided to become a coach, I honestly had no idea whether I'd be good at it. I spoke with people who knew me well and trusted their perspective. They all thought coaching fit who I was, so I took the leap. The confidence wasn't that I'd already be a great coach. It was that I could develop the skills if I committed to learning.
I had a similar experience years earlier when we built our house. Instead of hiring a general contractor, I became one. I had never managed a construction project before. I didn't know how to coordinate subcontractors, schedule inspections, or solve the dozens of unexpected problems that show up during a build. Looking back, it sounds a little crazy. At the time, it simply felt like another challenge I could figure out one step at a time.
Some people might call that overconfidence. Others might call it naïve. Maybe there was a little truth to both. But I wasn't walking into those situations believing I already knew everything. I was relying on evidence from my own life. Every time I'd taken on something unfamiliar, I'd eventually learned enough to become competent. That history gave me confidence that I could learn again.
Confidence Isn't the Same as Knowing
Over the years I've realized that's very different from believing you're good at everything. I'm certainly not. I have strengths, and I have plenty of weaknesses. There are things I should never attempt without someone far more experienced standing next to me. Confidence doesn't erase reality. It simply keeps me from assuming that inexperience is a reason not to begin.
Most people think confidence shows up after competence. Once you've mastered the skill, then you finally believe in yourself.
My experience has been almost the opposite.
Confidence gave me permission to begin. Competence came from doing the work.
That distinction has become one of my favorite lessons from the Confidence discipline in COR.E Dynamics. Confidence isn't about certainty. It isn't pretending you already know the answer. It's trusting that you're capable of learning, adapting, asking for help when you need it, and figuring things out along the way.
If you've been following this series, from awareness and acceptance through fearlessness and authenticity, you've been building the internal architecture that makes this kind of confidence possible. Confidence doesn't replace those disciplines. It stacks on top of them.
Why This Matters as a Leader
Leadership demands that mindset because the problems you're solving tomorrow won't look like the ones you solved yesterday. You'll lead people you've never led before. You'll make decisions with incomplete information. You'll face situations no amount of experience could have fully prepared you for. If you believe confidence only comes after you've done something successfully, you'll spend a lot of your career waiting.
Instead, I think confidence grows from remembering your own history. Think about the hardest thing you've learned to do. Maybe it was becoming a parent, starting a business, leading your first team, or changing careers. At one point, you had absolutely no idea what you were doing. Then, little by little, you learned.
That's the evidence I try to carry with me into every new challenge. My past doesn't guarantee success, but it reminds me that I've figured out difficult things before. More often than not, that's all the confidence I need to take the first step.
One Question to Leave You With
So here's the question I'll leave you with.
What are you avoiding because you don't know how to do it yet?
Maybe the better question is this:
Have you forgotten how many times you've already figured something out?
Your past doesn't prove you'll succeed at everything. But it does provide evidence that you're far more capable than your doubts would have you believe. That's usually enough to take the first step.
Ready to Stop Letting a Lack of Confidence Stop You?
Lack of confidence is one of the most powerful inner blocks I work with in coaching, and one that has a large impact on people's life and job satisfaction.
If you are waiting for confidence to start something, let's have a conversation.
A free discovery coaching session is a low-pressure way to explore what is holding you back with someone who has been exactly where you are.
Check out our other posts in this series:
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