Sunday Notes From the Deep End

There's a quality that separates those who attempt from those who achieve, those who dream from those who build, those who wish from those who do. It's not intelligence - plenty of smart people never launch. It's not capital - some of the greatest ventures started with almost nothing. It's not even opportunity, because opportunity is everywhere for those who can see it.

It's confidence.

Not the loud, chest-thumping bravado that mistakes volume for strength. Not the reckless certainty that ignores reality and crashes through guardrails. Real confidence - the kind that draws people to you, inspires trust, and enables you to navigate the inevitable storms of entrepreneurship.

Confidence is an attracting quality. People want to follow the confident, work with the confident, invest in the confident. Properly sized and placed, confidence makes those around you more comfortable. It provides a kind of psychological shelter in uncertain times. When you believe in the mission, others find it easier to believe too.

But here's what nobody tells you at the motivational seminars: confidence isn't something you decide to have one Tuesday morning. It's something you build, brick by brick, failure by failure, achievement by achievement.

For some people, confidence seems to come naturally. They walk into rooms like they own them. They speak with certainty. They make decisions without agonizing. For others, confidence feels like a foreign language they'll never learn to speak.

If you're in that second group, your self-messaging probably goes something like this: "I'll never be a confident person. That's just not who I am. I'm too cautious, too anxious, too aware of everything that could go wrong."

Here's the brutal truth: this is one case where what you tell yourself will absolutely determine the outcome. You're not born without the capacity for confidence. You've just convinced yourself it's impossible.

Even naturally confident people know fear. The difference isn't the presence or absence of fear - it's what you do about it. Confident people feel the fear and move forward anyway. Not because they're braver, but because they've trained themselves to act despite the fear.

It's difficult, if not impossible, to launch your own business without confidence. Think about what you're attempting: you're asking customers to trust you with their money, employees to trust you with their livelihoods, investors to trust you with their capital, and vendors to extend you credit.

Why would they? Because you believe in yourself, your idea, and your ability to make it happen. This belief must be so strong in you that you can overcome the inevitable hardships you didn't plan to experience - and trust me, they're coming.

The market will turn against you. Key employees will quit. Products will fail. Cash flow will evaporate at the worst possible moment. Capital will dry up. Customers will sue. Partners will betray you. The regulations will change overnight.

Without deep confidence - not in your plan, because your plan will change, but in your ability to adapt and overcome - you'll fold at the first real test.

But here's where it gets tricky: confidence must be balanced. Overconfidence can harm you and everyone around you. Cross that line too far and you'll come down hard.

History is littered with the wreckage of overconfident leaders who believed their own mythology. The real estate developer who over-leveraged because he'd "never had a deal go bad." The tech founder who ignored market signals because she was "disrupting the industry." The investor who bet everything on his "sure thing."

Overconfidence blinds you to risks, makes you dismissive of warnings, and causes you to overreach beyond your actual capabilities. It turns allies into yes-men, feedback into noise, and caution into cowardice.

So the first battle is to get confident. The next battle is to temper that confidence with a healthy dose of realism.

You don't gain confidence from participation trophies. You don't get it from affirmations in the mirror or motivational Instagram posts. You gain confidence through actual achievement.

Some of it is innate - certain natural abilities that come easier to you than others. But natural talent alone doesn't create confidence. Plenty of naturally gifted people lack confidence because they've never pushed themselves beyond their comfort zone.

Real confidence comes from the combination of:

Acquired knowledge. You studied. You learned. You understand the fundamentals of what you're attempting. Knowledge doesn't guarantee success, but ignorance almost guarantees failure.

Learned skills. You practiced. You failed. You tried again. You got better. Skills are knowledge in motion, and each small improvement builds confidence.

Repetitive application to the reflex point. This is where confidence deepens into mastery. You've done the thing so many times that you no longer have to think about it - you just do it. Professional athletes don't think through each movement. Skilled artists don't consciously calculate each brush stroke. Public speakers don't memorize every word. Business leaders don't agonize over routine decisions. They've reached the reflex point.

Repetition creates reflex. Reflex leads to increasing confidence. Confidence feeds more repetition and even greater skill levels. It's a virtuous cycle - if you can get it started.

Beyond repetition, confidence grows from:

Overcoming fear. Each time you do the thing you're afraid of, the fear diminishes. Not completely - you're not trying to eliminate fear. You're trying to prove to yourself that you can act despite it.

Faith. Whether in God, the universe, or simply your own resilience - believing that you'll figure it out somehow, that you won't be abandoned in the storm, that there's meaning in the struggle. Faith isn't certainty. It's confidence in the face of uncertainty.

Encouragement from others. Remember the Waterboy? "You can do it!" Sometimes you need someone else to believe in you before you can believe in yourself. There's no shame in that. We all need champions.

But life has a way of teaching humility to those who need it. Young children often seem supremely confident, blissfully unaware of their limitations. Then life beats them down, sucks the confidence out, and replaces it with anxiety and self-doubt.

This is painful but necessary. Confidence without reality-testing becomes delusion.

The Waterboy says "You can do it!" but life sometimes says "You can't do that!" Both messages are important.

Realistic self-appraisal. As Dirty Harry said, "A man's got to know his limitations." You're not good at everything. You don't have unlimited resources. Some opportunities are beyond your current capacity. Acknowledging this isn't weakness - it's wisdom.

Going trophyless. Not winning it all. Coming in second. Getting close but not quite making it. This teaches you that confidence isn't about being the best - it's about being capable and continuing to improve.

Failure. Not winning at all. Complete, humiliating, expensive failure. This is the crucible. You either emerge with tempered confidence - now aware of your limits but still willing to try - or you emerge broken. The difference is often just your interpretation of what the failure means.

The sweet spot isn't pure confidence or pure caution. It's the combination: confident courage.

Confidence from experience. You've done hard things before. You've survived setbacks. You've adapted when plans failed. This history gives you legitimate confidence that you can handle what comes.

Cautious courage in taking on something new. You prepare. You mitigate risks. You dip a toe in before diving. You're not reckless, but you're not paralyzed either. You move forward with eyes open.

Periodic self-review. Be brutally honest with yourself. Better yet, give someone you trust permission to be brutally honest with you. The moment you stop questioning yourself is the moment overconfidence begins creeping in.

Seek the company of superiors. Find people who are further along the path and learn from them. Accept their input. Trust their processes. You don't need to understand why something works at first - just follow the example of the person for whom it is working. Their confidence can inform yours.

Lend a helping hand to others behind you. Teaching forces you to articulate what you know and reveals gaps in your knowledge. Plus, helping others climb builds confidence in your ability to lead.

Embrace difficulty. This might be the most important one. Setbacks, conflicts, and difficulties aren't obstacles to confidence - they're the building blocks. As we climb the mountain we call life, it's the bumps that give us handholds and footholds, enabling our ascent. Smooth surfaces offer nothing to grip.

If you lack confidence, you can build it. Not overnight. Not by wishing. But through deliberate action: learning, practicing, failing, adjusting, and trying again. Each small win adds a brick to the foundation.

If you have confidence but lack results, check for overconfidence. Are you ignoring feedback? Dismissing warnings? Overreaching beyond your actual capabilities? Pull back. Temper it. Balance it.

The goal isn't to become fearless - that's psychopathy. The goal is to become someone who feels the fear, acknowledges the risk, and acts anyway because you've built legitimate confidence in your ability to adapt and overcome.

Confidence doesn't guarantee success. But the lack of it almost guarantees you'll never try anything worth doing.

So here's your assignment: Do one thing this week that scares you but that you're capable of. Not something reckless - something that stretches you just beyond your comfort zone. Then do it again next week. And the week after that.

Confidence isn't found. It's built.

One brick at a time. One difficult conversation. One uncomfortable phone call. One pitch to an investor. One attempt at something you might fail at.

The mountain is high. The path is steep. The bumps will bruise you.

But they'll also lift you higher than you ever imagined possible.