Failing Forward: Daily Practices to Encourage Growth

Todd Zipper
Monday Motivator
Published in
6 min readOct 31, 2016
2016-10-31-mm-social

I love reading about entrepreneurs. Entrepreneur stories are, for me, a little like fairy tales: Someone like Mark Zuckerberg or Steve Jobs starts a business in their garage and, as if by magic, it becomes a Facebook or an Apple. Of course, I know it’s not magic; entrepreneurs put a lot on the line to get the success that seems so fantastical to us, and it’s hard work. Lately, the entrepreneur story that’s captured my attention the most is that of Sara Blakely, the founder, sole owner and CEO of Spanx.

In 2012, Blakely became the youngest self-made female billionaire at age 41, according to Forbes. A few months ago, I watched an interview with Blakely, and I was struck by how well she articulates something that I think a lot of people struggle with. In the interview, Blakely shares her thoughts on failure and success. She talks about her father’s influence on her mindset, how he used to ask her what her failures were each day at dinner and how he’d congratulate her for them, even “high fiving” her. The lesson she took from that shaped who she became. She learned that making a mistake wasn’t the real failure; not trying was.

There’s a great Teddy Roosevelt quote: “It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.”

I think Blakely and Roosevelt are describing the same thing. I’ve talked in the past about growth mindset, grit and resiliency, and learning from failure is a big part of those concepts. You don’t accomplish anything by avoiding situations where you might fail.

10 Questions I Ask Myself Before Bed

This got me thinking about how I try to live these ideals in my own life. I’ve talked about the power of the Five Minute Journal before; what I want to focus on is the part that happens before bed, when you’re supposed to list three amazing things that happened that day and think about how you could have made that day even better. I love this exercise because it really forces me to reflect on the day and see where I can improve. Lately, I’ve expanded this into a list of 10 questions I go through before I go to bed.

How was I challenged today?
Growth comes from challenge and struggle. We need to remind ourselves every day of the benefits of challenge. This is especially important when a challenging situation makes us feel uncomfortable.

Did I learn anything new today?
If you were challenged during the day or if you failed, you should have learned something. Learning is about growth, but it’s also about change. In an interview, Amazon CEO and founder Jeff Bezos talks about how leaders shouldn’t be afraid to change their minds. Changing your mind isn’t the same as flip-flopping on a position; it’s a natural response to learning something you didn’t know before.

Was I kind today?
Pay It Forward, with Kevin Spacey and Haley Joel Osment, is one of my favorite movies. In the movie, Spacey plays a social studies teacher who challenges his class to change the world. Osment takes him at his word and comes up with the concept of passing on kindness you receive to people you meet — paying it forward instead of back.

We all get caught up in our daily lives, and this can make us a little self-centered. Sometimes it’s good to perform a simple act of kindness for another human being. This can be as simple as buying a coffee for the next person in line at Starbucks or helping someone out with a project at work. There’s very little downside to being kind, and it helps make the world a little bit better for everyone.

Did I help others to advance their lives and goals?
I try to always be the best version of myself and to help others do the same. I’ve discovered increasingly that these two ideas are inextricably linked: The more I focus on helping others achieve their goals, the more my goals become a reality. I’ve talked about Adam Grant’s Give and Take before — the idea that there are givers, takers and matchers. I tend to be a matcher in my life, but what if more of us tried to be givers? How much better would the world be?

What am I grateful for?
I’m not even sure if I knew what gratitude was until about 10 years ago. Gratitude isn’t the same as just saying “thank you;” it’s something you have to constantly work at. I work on it every day; I look at all the gifts I have and all the great things in my life, and I appreciate them and am grateful for them. Gratitude is a powerful positive emotion and a good antidote to stress.

What has me excited?
Often, your gut isn’t right. That said, you should still listen to what it’s saying. Your gut is often telling you what you’re excited about doing or what you’re leaning toward. When I used to work on Wall Street, my gut told me education was my passion. What might have happened if I’d suppressed that notion?

Did I laugh?
Life can get really serious. Too often, I’m Captain Serious. My kids are a great reminder to not take myself so seriously and to be present in the moment more often. Laughter, like gratitude, is a fantastic stress-reliever. My favorite show, when it was still on, was Seinfeld, because it was so goofy. It was a cultural touchstone and still is, and it was all about laughter. Even now, people in The Learning House office joke about sleeping under their desks, and they call it “pulling a Costanza.”

What am I afraid of?
Fears can be debilitating, but it’s important to examine them to find out why you’re afraid and what you can do about it. This is where the real growth starts. Like many people, I used to be afraid of public speaking. When I examined my fear, I found that it was all about ego: not wanting to be seen as a bad speaker, a bad CEO or even a bad person. I overcome that fear by realizing how ridiculous it is. It’s one speech; what’s the worst that can happen? It’s astonishing how powerful and liberating that question is: What’s the worst that can happen?

What am I frustrated by?
Frustration, anger and other emotions like it are all just manifestations of fear, and I find it useful to tackle the little frustrations of the day the same way I handle the things I’m afraid of. Did a person irritate me? Did an event not go as planned? Was this something that was in my control or out of my control? Do I have a strategy to accept the situation or change it? What am I really afraid of here, and how can I move past it?

Am I ready to crush tomorrow?
You have to lean into tomorrow; it’s a day full of potential. If you cultivate the habit of getting excited for tomorrow, you’ll find yourself ready to face all of life’s challenges with a can-do attitude, to learn from your failures, and to celebrate and be grateful for the successes of the day.

Blakely’s attitude of celebrating failure is a good one to have. It encourages reflection, growth and doing the things you’re afraid of. People tend to live in their comfort zones, myself included, and this daily practice has helped me push myself outside of my comfort zone, to where the good things happen. It’s like they say in the musical Hamilton: “When you got skin in the game, you stay in the game/But you don’t get a win unless you play in the game/Oh, you get love for it. You get hate for it/You get nothing if you wait for it.”

What do you do to learn from the challenges and failures in your life?

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Todd Zipper
Monday Motivator

Todd Zipper serves as President and Chief Executive Officer at Learning House. Todd writes about issues in higher education, and personal/professional growth.