How to Take Risks, Build Confidence & Keep Going: A Guide For the Sensitive & Shy (Like Me)

I took a risk last week.

I didn’t publish a typical Hackerella post – one that marries personal anecdotes and insights with research and data.

Instead, I decided to share 2500 words (and accompanying photos) about a little girl who finds a magic wand in the woods.


Not exactly the work you’d expect to read on this blog, but it was the final result of my creativity challenge, so I went for it. I hit publish and went about my day.

And then…. crickets.

I didn’t receive much of a reaction from anyone. Very few comments or compliments, and a bunch of email list unsubscribes.

It was scary to share something I put so much time and effort into, scarier yet that it was beginner work (my best work, but beginner work nonetheless). So it sucked to not have it validated.

But I didn’t take it personally because there was nothing personal to take.

I completed what I set out to accomplish and am proud of the end result (well, I’d started the musical interpretation of the story complete with narration, piano, and layers of computer generated synthesizers and melodies, but I don’t have anything to share quite yet).

garage band

Anyway, a lot of effort went into this challenge. It pushed me creatively, forced me to be resourceful and scrappy and vulnerable, and I loved every minute of it; not in spite of it’s difficulty, but because of it.

Shifting Mindsets

I never expect to cruise through a challenge without encountering any setbacks. Easy games, easy challenges, easy problems to solve – where’s the fun in that?  The real satisfaction lies on the other side of our comfort zones.

Goals should be difficult to achieve because those achieved with little effort are seldom appreciated, give little personal satisfaction, and are often not very worthwhile. – John Wooden, Wooden

I’ve written about the importance of persistence before, and how we have to take risks and open ourselves up to failure. Now, having done 14 challenges in a row, I finally feel I can anticipate and deal with obstacles (and failure and rejection) without being blanketed in a wave of self doubt.

The Buddhists call the practice “turning poison into medicine”. Others call it grit, endurance, or mental toughness.

Either way, it’s a mindset. An ability to commit and play the long game.

Female soccer great Mia Hamm says (as paraphrased by Carol Dweck in her book Mindset):

When eleven players want to knock you down, when you’re tired or injured, when there referees are against you, you can’t let any of it affect your focus. How do you do that? You have to learn how.

So let’s talk about how to learn how.

1. Expect and embrace failure

As Michael Jordan said in his famous Nike ad “I’ve missed more than nine thousand shots. I’ve lost almost three hundred games. Twenty-six times I’ve been trusted to take the game-winning shot, and missed. I’ve failed over and over and over again in my life. And that’s why I succeed.”

We have to expect obstacles. We have to find a way to turn them into motivation, and have faith in our ability to overcome them.

The process of changing a habit or pursuing a new endeavor, requires the assumption that that things will not go according to plan. The key is to use the roadblocks as drive to press on, and not as reason to question talent and self worth.

2. Analyze the feedback

Some decisions lead us in the right direction, and others lead us off course. The only way to assess progress is to listen to the feedback.

Here, all of the comments, responses, lack of responses, opens, likes, unsubscribes, and suggestions help me adjust and refine my approach to this site. Case in point: the short story, wherein I’d neglected to take into account something very important – my audience. People sign up for the newsletter to read about personal development and wellness, not to read stories for children, no matter how phenomenal they are, and I need to remember this each time I design, write and package up a post and a challenge.

3. Ask yourself – what’s next? 

At this point, the only thing left to do is accept what’s happened and move on. Take the feedback, decide what’s next, and take action on it.

I immediately made a list of all the things, big and small, I could do to improve my blog, my writing, and even the story too. And then I got right back to work.

4. Keep stepping outside of your comfort zone

Because the more we expose ourselves to uncomfortable things, the more we’ll get used to dealing with drawbacks. Repetition breeds familiarity, and it makes a world of a difference.

Kids,  Mindset & a New Challenge

All this talk on mindset got me thinking, how do I teach this to my kids?

We all want the same thing – to raise confident, happy and successful kids. But there’s no specific blueprint for how to do that. We do our best, but even then, not a day goes by where we don’t second guess the decisions we make for our children.

That’s why I’ve decided to spend the next two months (aka summer vacation) on “the parenting challenge”.

kids mindset

I’ll be experimenting with the different child-rearing philosophies out there – schooling, un-schooling, routine, discipline, play, creativity, memorization, experimentation and more.

At the end of it all, I want my girls to know (my five year old in particular) that we are all works in progress. That we can always grow our abilities and our character and do anything we set our mind to, even if they’re hard. Especially if they’re hard.

Parents think they can hand children permanent confidence—like a gift—by praising their brains and talent. It doesn’t work, and in fact has the opposite effect. It makes children doubt themselves as soon as anything is hard or anything goes wrong. If parents want to give their children a gift, the best thing they can do is to teach their children to love challenges, be intrigued by mistakes, enjoy effort, and keep on learning. That way, their children don’t have to be slaves of praise. They will have a lifelong way to build and repair their own confidence.
― Carol S. Dweck, Mindset: How You Can Fullfil Your Potential

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