You Can Do Hard Things

Episode 2

August 21, 2026

If you never make your kids do hard things, they’ll never realize that they can do hard things. Am I saying that you should let your children flounder without support? No - absolutely not. But if they’re never challenged within a loving, supporting environment, they’re never going to realize that they are capable of rising to the occasion when you’re not around.

Remember that trend a few years ago that was something along the lines of, “I’m an Asshole Parent”? And parents would post pictures of their kids in tears because they wouldn’t buy them a second ice cream cone (after they threw their first one at their sibling) or because they wouldn’t let them make their pet rabbit do a handstand (true story), etc. I spend a lot of time - even today - feeling like an asshole parent. I have high expectations for my daughter - just like I have high expectations for all the people in my life. But I marry those high expectations with my support. In other words, I’m not ever going to ask her to do anything completely and totally on her own that I don’t think she can actually do. But if I never challenge her to do hard things, she’s never going to know that she can actually do hard things.

Case-in-point: We were in Santorini, Greece (BEAUTIFUL country…I highly suggest visiting…the Grecian flag is blue because that is the color of the sky there all the time…I know a great travel agent if you decide to take the trip). There are 588 steps that go from the old port up to Fira on Santorini. Many people take the cable cars or the donkeys to get to the top of the 588 steps. Being an animal lover, there was no way I was ever going to take a donkey, but I didn’t need to make that decision because we were at the top of the 588 steps. We didn’t need to figure out a way to get up as many tourists do. Like the crazy person that I am, I made my family walk down the 588 steps just so we could turn around and walk back up to 588 steps just so that we could say we walked up and down 1,176 steps because we could walk up and down 1,176 steps.  In my mind, COMPLETELY logical.

The 588 steps down were GREAT! The view was amazing! The steps were nice and wide so you could actually look around while you walked instead of being focused on your feet. Even the donkey poop was entertaining!

My daughter cried on the way back up. Sobbed. Bawled. Thought she was going to die.

For a hot second, I second-guessed myself. Did we carry her back to the top? Um, she’s 14 at this point and mom-sized so no. Did we go back to the bottom and tell her she could hop on a donkey and ride the donkey the rest of the way up? Hell no. She stepped her way up the rest of the steps. because 1) she’s absolutely physically capable of doing so and 2) if I would’ve let her quit, she would’ve never had figured out that she could hard things.

Now, did I walk behind her poking her with a stick every time she slowed down and demand that she maintain a certain pace? Certainly not! When she wanted to take a break, she took a break. When she wanted a drink, she took a drink. When she wanted to stop to cry, she stopped to cry. We allowed her to struggle within our supportive parental embrace (figurative embrace because it was like 90 degrees and we were climbing stairs so ew to embracing). And guess what? She made it to the top of those 588 stairs! She lived to tell her story about the 588 stairs!! Most importantly, she did something that she did not think that she could do because we pushed her to do it while we supported her every (literal) step of the way. In the end, that is what we should want for our kids - we should know that we are sending them out into the world with the skills that they need to take on hard things because we ensured that they had the experiences that proved to them that they are capable of doing hard things.