What Are You Still Holding Against Yourself?

A moment from 10 years ago. I understand it differently now.

We often judge our younger selves with wisdom we had not yet lived long enough to earn. I caught myself thinking recently about some of the expectations I had for my kids when they were younger. There were times I expected them to be more focused, more disciplined, more responsible, more certain about what they wanted. I could get frustrated when they were goofing around instead of taking something seriously or making a decision that seemed so obviously wrong to me. Looking back, I can see moments when I expected a ten-year-old to think like a twenty-year-old. I wanted them to understand consequences they had never experienced and make decisions with perspective they had not yet lived long enough to earn.

At the time, I thought I was preparing them for life. I was teaching them to work hard, make good decisions, and become capable adults. Parents are supposed to guide their children. But I also wonder how many times I was frustrated with my kids for simply being the age they were.

When they were young, I wanted them to find the sport they were best at. Now I understand they needed time to play all of them. They needed to run onto fields and courts and try things they might eventually quit. They needed to discover what came naturally and what did not. Every season did not need to lead somewhere. Some seasons were allowed to simply be fun.

Then they got older, and the questions got bigger. What do you want to study? Where do you want to go to college? What do you want to do with your life? I wanted them to have answers because I thought answers created direction. But how is an eighteen-year-old supposed to know exactly what they want to spend their life doing when they have barely had a chance to experience the world? How can someone know who they want to become while they are still discovering who they are?

Today, I can see both of my kids becoming themselves in ways I could never have planned for them. Zac found his way into real estate. Aspen is in college, running, learning, experiencing life, and continuing to discover what matters to her. They are not finished. They are not supposed to be. Neither am I.

They did not need me to know who they were going to become. They needed time to become them.

There are things I could have told my kids a thousand times that they still needed to learn for themselves. Some lessons cannot be transferred from one person to another. They have to be lived. A disappointment changes you. A conversation changes you. Someone believes in you. Someone breaks your heart. You succeed at something you were afraid to try. You fail at something you thought you were good at. You leave home. You miss home. Life gives you enough experiences to finally understand things no one could have explained to you sooner.

And then I realized something. I have spent years looking back at earlier versions of myself with the same expectations I once placed on my children.

I have replayed decisions and wondered how I did not see what now seems obvious. I have questioned why I stayed too long, waited too long, made the wrong business decision, worried about something that never mattered, or failed to appreciate a season until it was gone. I have looked back at a younger Craig and expected him to know what I know today.

But he had not lived these years yet. He had not had the conversations I have had. He had not made the mistakes I have made. He had not watched his children grow up. He had not spent thousands of conversations listening to people talk about their lives. He had not lived through cancer. He had not yet learned what only time could teach him. Of course he did not know what I know now. How could he?

We give children permission to grow into who they are. We understand that a ten-year-old cannot have the perspective of a twenty-year-old because ten years of life stand between them. Yet we look back at ourselves with none of that understanding.

We judge a decision we made twenty years ago using twenty years of information we did not have when we made it. We criticize ourselves for missing signs we only recognize because we now know how the story ended.

You cannot use today’s wisdom as evidence that yesterday’s you should have known better.

That does not remove responsibility. We should own the choices that hurt people, apologize when an apology is owed, learn, and grow. But growth should never become another weapon we use against the person we used to be.

The fact that you can look back and see something differently is not proof that you failed then. It may be proof that you have grown since.

I wish there were moments when I had given my kids more time. More time to play. More time to figure things out. More time to be uncertain. More time to become. I cannot change those moments. But I can let what they taught me change the way I see my kids today.

And maybe I can finally offer the same understanding to myself. The person I was did not have the years that followed. He needed time too.

What are you still holding against yourself... that only time could have taught you?

Write a future you’re excited to live.

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​If this letter made you think differently about the person you used to be, The 10-Year Letter will help you think more intentionally about the person you are becoming.

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