One of my favorite podcasts to listen to is How I Built This, an NPR show hosted by Guy Raz. It's a raw, authentic, and vulnerable look into the lives of notable entrepreneurs and the journey of creating their companies. The most recent episode featured Steven Madden, the owner of his self-named shoe empire. He delved into his $3 billion company and the atypical route he took to get there.

According to the podcast, he's not very welcome in the shoe industry for a few reasons, but mostly because doesn't hail from a fashion capital (read: Paris or Milan), and doesn't have a background in design. Madden is uniquely himself. He just genuinely loved designing and selling shoes.

But it wasn't all fun and easy for Madden. He served two and a half years in prison for financial crimes, but upon reflecting on it, he doesn't regret a day in prison. He regrets being greedy for money, but not for the actual time he spent in there.

After all is said and done, Madden had one strong takeaway for all entrepreneurs:

"You know, so there were some mistakes that we made, but we did so many great things. And the thing about that is if you start getting gun-shy and start being afraid to make a mistake, you'll never have the brilliant ideas."

Oftentimes, we are so scared to try new things because we are afraid to fail. We don't want to embarrass ourselves or look bad. But here is Madden, a man who served time in prison and is still running his self-founded shoe company, telling us that we should still be unafraid to try new things (with caution to not end up spending time in the former).

So, how does a person go about trying new things without being afraid?

I implemented a personal program that helped me step out of my comfort zone and motivated me to try new things without fear of failure. If you're looking to do the same, try this self-tested technique.

  1. Write a list of all of your ideas. They can be big picture items related to a life or career change, or they can be solution options to a current issue. Write them all down - the good, the bad, and the weird.
  2. Narrow the list to your top five or top ten.
  3. Reflect on each idea and acknowledge why you haven't tried it yet. If the answer is something like, "I'm too scared to fail" or "I don't want people to think I'm crazy", those are considered invalid excuses and should stay on the list. If the answer is a bit more consequential and can result in actual damage, then remove those from the list.
  4. Spend the next 30 days executing the list.
  5. What works is successful because you've found a solution to your issue. What doesn't work is also successful because you've learned a key lesson from it.

Last month, I tried this exact program and it led me to my latest venture of starting a corporate wellness company. My other four ideas didn't pan out too well, but now I can stop thinking about whether or not these ideas are good. Now I have a solid answer and I can move on to the next batch of ideas.

When it comes to trying new things we oftentimes can feel scared or unsure of the consequences, but with a carefully curated and thoughtful list, this can all change. At the end of the day, don't be afraid to make mistakes. Don't let the unknown fear of results hold you back from finding out or landing on your next big idea. You owe it to yourself to try new things.