A recent conversation with a good friend brought something into sharp focus for me… writing something in her planner and not doing it is way worse than never writing anything at all. 

She said, “I’d rather get up and just work at whatever than plan and fail.”

“If I write this down and don’t do it, I’ll feel like a failure.”


Have you felt this way? 

I think the biggest thing for me is “feel like a failure.”

It came from a smart, beautiful, successful person… The LAST person I would expect. 

I was taken aback and am still processing the conversation but here are my initial thoughts:

We’re all the same.

I’ve had this realization many times in recent years. We may measure success in different ways but a common one is financial success. Power, money, position, etc. But I’ve had enough conversations with CEO’s, executives and small-business owners to realize we truly do put our pants on the same way.

Many traded healthy relationships (or their own health) for work and money. They, while locked down and put together at work, have horribly messy home lives. Others put on a happy face while burying pain, insecurities, and turmoil.

The common thread is imbalance. They found success and leaned into it at the expense of the other parts of their lives. Sure, it looks good from the outside, but that doesn’t mean it’s as perfect as it appears.

We need to redefine failure.

I think the majority of us shy away from failure because we see failures as a reduction of our worth… or proof of our low worth

That makes me sad to write.

I know those feelings. I’ve had them and, at times, still do. 

We need to reframe failures as learning experiences. It’s hard, though, mainly because society likes natural talent. We like to celebrate gifted people and give them god-like recognition. Rarely do we dig in and see the hard work they put in, and the failures they pushed through. 

Meanwhile, we expect that if we aren’t good at something, it’s just not meant for us. It’s easier to pivot and walk away rather than see a shortcoming and work on it. We don’t want to feel the struggle. Even more, we don’t want to be seen struggling. It’s weakness.

But it’s not. The best example I’ve ever read is that of a toddler… What if a toddler stood up, took a step, fell, hit her head, cried, and at that moment, decided walking just wasn’t for her? That’s not realistic! And neither is expecting that we won’t fail as adults. We will. The sooner we accept that, the sooner we can unlock the lessons we gain from failing.

We are our own worst critics.

Judgments, criticisms, labels… often the worst ones come from within ourselves. I’ve learned two things in relation to this point:

  1. We are far worse on ourselves than other people are. Most people are so worried about their own issues that they don’t care about ours. Even if they notice, they most likely won’t remember.
  2. The people who do criticize others are probably dealing with a very harsh inner critic themselves. So much so that they have to externalize it to make themselves feel better. While a minority in our lives, they are the loudest and most hurtful, so we give them a lot of space in our minds, and it hurts us.

Learning to be aware of our failings without becoming toxicly judgmental is imperative if we’re going to have a healthy relationship with failure and, ultimately, ourselves.

How to move forward…

Step back and assess what you truly value.

The biggest problem with people who live in imbalance is the regret that they didn’t live a life in alignment with their values and true purpose on this earth. They chased shiny objects, did what was easy, or simply didn’t realize they were on the wrong path. 

This is exactly why we spend a few minutes each day touching base with our goals in the Define My Day process – so that we can make the tiny, daily choices that gradually put us on our ideal path. It will never be perfect but it will be worth it.

Takeaway: Life is a journey. Your life’s purpose is the destination. Define My Day is your guidebook that helps you find the healthiest path to your ideal self.

Learn to see failure as an opportunity

“Fail early, fail often, but always fail forward” -John Maxwell

We learn best while failing. If you never fail, you’re probably living a limited existence – boxing yourself in. You already know it but take a moment to remember that everyone fails, though some are good at hiding it. And while failing can sting, if you can learn from the experience and improve, you’ll never regret the experience.

Takeaway: Failure is a key feature of learning and development. By taking lessons from failure, we can learn skills, improve our performance, and even have empathy for others doing the same. When we review in Define My Day, we do it with an eye toward small daily steps of improvement. 

Give grace

Once you understand that no one is perfect, we all make mistakes, and that everyone has their own struggles and failures, you can stop letting your own faults and shortcomings define you. It takes time but, as someone who was once intensely critical of himself, I know that you can give yourself grace too. 

Takeaway: In the Define My Day process, write some positive affirmations to use as a mantra when you are feeling hard on yourself. Practice gratitude by writing down something good you appreciate today. And, when planning your priorities, realize that sometimes you may need to prioritize rest and self-care. 

I hope you take the small steps today that move you toward the life you desire.

Keep moving forward,