In Praise of Doing Hard Things (Badly)

Introduction

I recently bought an online singing course.

Yes — me. A guy who, in high school, was told (by his best friend no less) that his back-up vocals were so wildly off-key that it “actually worked as harmony.” Spoiler: it didn’t. That wasn’t a compliment.

So why, at this point in my life, am I subjecting myself to the vocal equivalent of trying to ice skate uphill? Because failure, done right, is a feature, not a bug. That tension — the possibility that I’ll fall flat on my face — is exactly why I’m doing it.

This post riffs off something my partner Paul recently wrote — a short piece about why we should choose to do hard things, even when we don’t have to. His point: voluntarily taking on challenge reminds us that we can do hard things when we do have to.

I’d like to take that a step further. What if challenge itself is the point? Not just pursuing goals that happen to be hard. Not just gritting our way through discomfort to build resilience. I’m talking about embracing challenge — and the possibility of failure — as a foundational habit of a well-lived life.

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“You keep using that word… I do not think it means what you think it means…”

— Inigo Montoya

What Counts as a Challenge?

Let’s start with a working definition:

Challenge: a situation that requires great mental or physical effort in order to succeed — and by definition, tests your ability.

The key feature here? Uncertainty.
If you know you’ll succeed, it’s not a challenge — it’s a task. A box to check.

Sure, you may be relentless in pursuing success — in fact, you should be encouraged to do so. Settling for failure without ever returning to the drawing board to figure out how to try again differently is definitely not what we are after. You may have a great track record of eventually figuring things out and making progress toward goals. But if you’re setting the bar so low that you end up batting 1.000 on the first try, you’re not challenging yourself — you’re reinforcing competence, not stretching into growth.

Let’s call it what it is:

If you never fail at the things you call “challenges,” they probably aren’t.

That doesn’t mean we pursue failure. It means we pursue things that are hard enough that failure is a possibility — maybe even a likelihood at first.

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Why Bother? The Psychological Upside of Failing (Well)

Taking on hard things you might fail at builds you in ways comfort simply can’t. Here’s how:

1. Growth Mindset

Failing is proof that you’re in motion — that you’ve stepped out of the loop of repetition and into the terrain of growth.

Josh Waitzkin, in The Art of Learning, warns against what he calls the “anorexic hermit crab.” A hermit crab has to shed its shell when it outgrows it and go find another to relocate to. It is vulnerable during this process until it finds a new dwelling. The metaphor resonates with our pursuit of true challenge: the crab stays inside a too-small shell, refusing to grow because it fears the vulnerability of change. But staying “safe” becomes suffocating. Eventually, it dies in the very shell it refused to outgrow.

Your comfort zone will kill you. Slowly. Silently. Comfortably. It’ll look like productivity. It’ll sound like confidence. But if you’re not risking a little — you’re not growing at all.

2. Resilience

This is Paul’s thesis, and it’s dead-on: we do hard things when we don’t need to so we can still do them when we must.

Failing in low-stakes environments is how we inoculate ourselves against future adversity. Every challenge taken voluntarily becomes practice for life’s involuntary ones.

Think of it like this: every time you finish something that scared you a little — not because of danger, but because of uncertainty — you’re stacking emotional proof that you’re stronger than your excuses.

3. Humility

Humility is more than a virtue; it’s a force multiplier in real challenge. When you take on something where the outcome is uncertain, you remember that effort, training, and support are essential — not optional.

I’ve noticed that when I’m too comfortable in something, I stop asking for help. I stop listening. I start assuming. Taking on something new breaks that habit fast. Humility reminds us to respect the process — and to respect the people who are further along in it.

And like any muscle, humility atrophies when unused.

4. Beginner’s Mind

This one hits close to home for me — as a teacher, mentor, and lifelong learner.

Taking on something new reconnects you with what it feels like to not know. It forces you back into that vulnerable, foggy, uncertain place your students and mentees live in all the time.

You want to be a better mentor? Go fail at something in public.

That singing course I mentioned? One of the biggest reasons I signed up was the pitch: the instructor used to be terrible. He got better through deliberate practice — not divine talent. His former teacher, by contrast, was so naturally gifted she could no longer identify with the struggles of beginners. Her feedback stopped helping.

This resonated with me immediately — not just as a student, but as a coach. I’ve seen the same thing happen with some of my chess students. A few had worked with Grandmasters who were absolutely brilliant… but too far removed from the beginner’s experience to explain or empathize. Their advanced students flourished. The newer ones floundered.

And it wasn’t because the Grandmasters were bad teachers — it’s just that empathy fades when you forget what it feels like to be lost.

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What Happens When We Avoid Challenge?

Here’s where Jonathan Haidt enters the chat.

In The Coddling of the American Mind and The Anxious Generation, Haidt outlines a phenomenon he calls safetyism — a culture of excessive risk avoidance, wrapped in good intentions but riddled with consequences.

The short version? Our overcorrection for safety and emotional shielding has led to a spike in anxiety, depression, and fragility — especially in younger generations. There’s also research showing that learning benefits all ages and may even help stave off cognitive decline later in life. But the effects don’t stop at the individual scale.

Economist James Pethokoukis goes even further in The Conservative Futurist, arguing that this fear of failure has even stalled innovation — including in climate tech like nuclear energy — because the political and emotional risks of failure were too high. We’re not just risking personal stagnation anymore; we’re trading societal progress for short-term comfort.

Avoiding the discomfort of small failures leads to the certainty of bigger ones.

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So What Do We Do With All This?

Let’s get practical. If challenge is the point, how do we intentionally incorporate it into our lives — without being reckless or performative?

Here are some ways I’ve been doing it lately:

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Five Ways to Make Challenge a Habit (Even When You Might Fail)

1. Pick a 50/50 challenge.
Not a sure thing. Not a guaranteed disaster. Find something that sits right in that maybe-I-can-pull-this-off zone. That’s where growth lives.

2. Try something brand new — or just unfamiliar.
This week I’m at a music workshop. I’ve played a musical instrument for 40+ years, so I’m not new to music. But even in a domain I know, I’ve found brand-new edges to lean into.

• I signed up for a songwriting class, which ends with composing a song and lyrics and performing your original tune in front of the class. I’ve never written a song. I’m still a terrible singer. Honestly, calling this a coinflip might be generous.
• I also picked an ensemble ukulele workshop. I started learning last year. This year, the goal is to improvise and solo in a group setting — something I’ve never done on this instrument.
• To top it off I asked my current blues guitar teacher for any recommendations on the workshops. He identified a terrific flatpicking bluegrass guitar player for me to check out. This isn’t a style of music I’m actively studying, but it has the benefit of challenging my picking hand in a way that my usual music styles can’t.

Even when you know a field well, there are adjacent challenges that will stretch you. That’s the key: stay adjacent, but uncomfortable.

3. Share the challenge.
My wife and I recently started learning tennis. We were both athletes in a former life and still stay active, but tennis is new ground. We’re terrible — I mean laughably terrible, but it’s cool because we’re learning together. There’s something deeply connective about shared incompetence. We get to fumble and grow together as partners, not just players.

4. Let failure teach you.
Don’t just fail and walk away. Let it sting a little. Try again.  Reflect. Laugh. Swear. Ask what worked and what didn’t. Try again. Let it be messy — and meaningful. Find a coach, read a book, check out that YouTube video. Try again.

5. Use the discomfort to deepen your mentoring.
Every time you stumble through something new, you earn more credibility with the people you teach, coach, or guide. You’re not just telling them to be brave — you’re showing them what bravery looks like in practice. We dragged my son out to the court recently. He’s a terrific athlete, but he is a special kind of awful on the tennis court — but it wasn’t about getting to Wimbledon. It was a good opportunity to learn together, spend time, and model what real mentoring and parenting look like in action.

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Final Thought

You don’t have to be good at everything. In fact, you shouldn’t be.

But you should regularly try things that make you nervous. You should aim for goals where the outcome is uncertain. You should learn to fail — without folding — because that’s where real growth lives. That’s where the story gets good.

A life without challenge might feel safe — but it won’t feel alive.