I was watching my sister-in-law dancing with her new husband this past weekend. Both their faces exuded the type of love you always hope a new couple feels. (And honestly, it’s interesting that I’m here talking about weddings again—given that it’s not a typical topic of mine).

I sat mesmerized looking at her. She was one of the most beautiful brides I have ever seen. Yes, she is gorgeous. In all the years I have known her, she never looked more happy.

And I contemplated the various moments that had led to this one. The beautiful children she'd raised. The pain of a previous marriage that ended. The years between then and now. And the blessing she'd found in the man standing beside her.

She joked that she was the only grandma bride, but looking at her, it would be the last thing you thought given her winning the gene pool lottery.

But honestly, she glowed with the kind of joyfulness and wisdom that only someone who understands what is truly worthy of cherishing in this life can own.

What struck me wasn't simply that something painful had eventually been replaced by something beautiful. That is too simplistic to attribute to this moment.

It was that the woman standing before me had been formed by a life she never could have planned in advance.

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It made me think of my own life.

My parent’s life.

The people around me whose experiences weren’t planned but formed the people they are today.

The juxtaposition of planning our perfect life and understanding the wisdom gained through life experiences we would have never chosen.

Sometimes we hold on to those perfect lives and the aspirations that we imagine will unfold when everything goes according to plan.

But how often does that actually happen?

We all have ambitions, and they are not wrong to hold. They are merely the starting point for an adventure that we decide to embark on.

But somewhere between the launching point and the final destination, we replace ambition with requirements. And we hypothesize that the outcome must be the way we imagine or else we have failed.

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I've felt this countless times in my life. Each time preceded by periods of questioning.

Questioning myself.
Questioning my decisions.
My capabilities.

Wondering if I was in the middle of some Dunning-Kruger moment where what I had once felt so optimistic about became something I wasn't quite sure I could see through.

Maybe I'm really not equipped to handle this.

It's usually in moments like these that I think I've reached the end—or the bottom, whichever feels most appropriate.

I've felt it in relationships, in my career, in business, and with homeschooling my son.

And I used to think these moments were followed by another door opening.

Sometimes they are.
But sometimes another door doesn't open for a very long time.
Sometimes the door that opens isn't the one we wanted.
And sometimes nothing about our circumstances changes at all.

We simply reach a point where we can no longer keep carrying the idea of how we thought things were supposed to turn out.

I felt something similar this week as we began a new year of school.

When I set out to homeschool, I had no idea what I was doing. And after five years of feeling the same roller coaster of emotions, you’d think I’d have overcome this. But the thought of teaching junior high plagued me over the past year.

And those same questions came looming again.

Am I doing the right thing?
Am I capable? Qualified? In my right mind?
Have I failed my son?

So I began pondering our options.

What I couldn't see at the time was that something else had already been changing.

Over the past year, I had been clearing out my calendar. Ending partnerships. Removing commitments and roadblocks. Letting go of things that were pulling me further away from my priorities.

I didn't do any of that because I knew what was coming next.
I did it because the way I was living wasn't working anymore.

Then we found a new hybrid curriculum that was rigorous and aligned with our values—one that would require considerably more of my involvement and teaching.

A year earlier, I wouldn't have had the capacity for it. I didn't know I was making room for this. I just knew I needed to make room.

And when I look at my business, I can see the same pattern.

For years, I was trying to figure out how to become successful in the eyes of everyone else—doing what my business coach and fellow colleagues were all doing.

But what I mostly wanted was to do meaningful work. Not busy work.

I wanted to help people. I wanted to build something that supported my family and gave me the freedom to be present for the life I had intentionally chosen.

They were desires that had kept me going.

But somewhere along the way, I developed an idea of what succeeding online was supposed to look like.

More clients.
More revenue.
A clearer offer.
A bigger audience.

A business that looked like the businesses of people who seemed to have figured it out, but also led lives that were starkly different than mine.

And slowly, the thing I had built to support the life I created began competing with the life I valued.

The same thing happened with homeschooling.

I cared so much about doing it well that I began carrying an image of what a good homeschool was supposed to look like.

And when reality didn't match the image, I assumed I was failing. That's the uncomfortable thing about perfection that we don't always say out loud.

Sometimes holding onto perfection makes us terrible people.

Not intentionally.

But the stress of trying to force reality to conform to the picture in our heads can make us impatient. Controlling. Distracted. Resentful. Perpetually dissatisfied.

We can become so consumed with creating the perfect business that we lose sight of what the business was meant to serve.

So focused on creating the perfect education that we stop seeing the child sitting in front of us.

So committed to becoming who we think we're supposed to be that we have very little compassion for the person we actually are.

The problem isn't always that we care too much.

Sometimes we've simply asked the thing we care about to carry something it was never meant to carry.

Our identity.
Our worth.
Proof that we made the right decision.
Proof that we're capable.
Proof that the sacrifice was worth it.

And when that thing begins to fall apart, it doesn't merely feel disappointing. It feels like something about us is falling apart with it.

I had to let go of becoming the kind of coach I thought I was supposed to become before I could see something deeper in the work I'd been doing all along.

I had to let go of creating the perfect homeschool before I could see other ways of supporting both my son and myself.

Neither happened because I suddenly stopped caring.

I think I cared enough to finally admit that the way I was carrying it was hurting the thing I loved.

Maybe that's part of why letting go is so difficult.

We're rarely just letting go of a plan. We're letting go of the person we imagined we'd become if the plan worked.

For me, this is where trust enters.

My faith means that trust ultimately rests in God. But I don't mean trusting that God will eventually give me the outcome I wanted, or that every closed door guarantees a better one waiting conveniently around the corner.

I don't know that.

None of us can foresee the future or know fully that everything will be okay.

Trust, for me, has increasingly meant accepting that I cannot always see how I am being formed while I'm in the middle of the formation.

And I think there is a principle here that extends beyond faith.

We simply cannot know what every decision, disappointment, relationship, failure, or unexpected turn will eventually mean.

Looking backward, I can see patterns in my life that I couldn't have recognized while I was living them. There were things I desperately wanted that never happened, and things I never wanted that changed me in ways I couldn't have anticipated.

I wouldn't have asked for many of those experiences. Some required pain, disappointment, or the reshaping of a life I had become deeply attached to.

That doesn't make the pain secretly good. And I don't think every disappointment needs to be turned into a lesson to justify its existence.

But I do know that some of what I once interpreted as failure became inseparable from who I am now.

Which makes me wonder how much time we spend focused on who we think we're supposed to become without noticing how our lives are already forming us.

There is nothing wrong with making plans or pursuing excellence. I still do both. But I am beginning to understand how easily a plan can become something else entirely. We stop allowing it to guide us and start requiring our lives to conform to it.

Perhaps that's where letting go matters.

Not because another door is guaranteed to open. Sometimes it doesn't. Sometimes what comes next looks nothing like what we wanted. And sometimes we have to live in the uncertainty much longer than we'd like.

For me, trust is learning to live there without requiring an explanation for everything that has happened or certainty about what happens next.

I can look back now and see things I fought desperately to preserve that needed to change. I can also see how often I called something a failure simply because it didn't turn out the way I had imagined.

I'm sure there are things happening in my life right now that I won't understand for years. Maybe some of them I never will.

I think I'm becoming more comfortable with that.

I don't have to understand the whole story to live the chapter I've been given.

And perhaps part of living it well is learning the difference between what is ours to carry and what we are finally being asked to let go.