Planning for a New Year Starts With Looking Honestly at the Old One

Every year, right around this time, something shifts in the organizations I work with. The calendar starts to thin out. People begin to take a few deeper breaths. Leaders start asking bigger questions.

“What do we want next year to look like?”
“What do we need to change?”
“How do we get better from here?”

This is the season when my work as a consultant is less about solving problems and more about helping leaders slow down long enough to see themselves clearly. Planning is hopeful work. But it’s also honest work. And most leaders are good at the hope part. It’s the honesty that’s harder.

Because planning requires something uncomfortable: The willingness to look back.

Not with excuses. Not with defensiveness. And not with selective memory.

With reality.

The Past Isn’t the Enemy, but It Can Be the Shadow

There’s a saying I’ve used for years: “I am not where I am going to be, I am not where I want to be. But thank God I am not where I was.”

It stirs something in me every time. It captures the tension leaders live in, the space between gratitude and ambition. But buried inside are a few truths that planning forces us to face:

You are not where you want to be. You are not yet where you’re going. And where you came from still matters.

A lot of people want to plan for growth. But far fewer want to look back at the darkness that held them in place.

The conflict they avoided. The ego they protected. The decisions they rushed. The people they failed to develop. The systems they outgrew but never replaced. The pain they carried into the room without meaning to.

This is the Shadow, the Upside Down version of our leadership. It’s not who we want to be. It’s who we were when pressure, fear, insecurity, or exhaustion got loud enough.

And if we don’t look back at it with honesty, we carry it right into a new year and act surprised when we find ourselves in the same patterns.

Leaders Love Growth Plans… Until It Means Owning the Shadow

Every November/December, I hear the same thing:

“We want to grow next year.”
“We want to level up our people.”
“We want to scale.”
“We want more accountability.”
“We want more clarity.”

Growth is inspiring. It feels good to say out loud. But growth exposes whatever we haven’t dealt with.

If you avoid conflict at 10 people, you’ll drown in it at 50. If you refuse to delegate at 1 million in revenue, 5 million will break you. If you cling to being the hero, your team will never become leaders.

And if you don’t turn around and look straight into the shadow of last year, you’ll repeat it, just with more weight on top of you.

Looking back isn’t punishment. It’s preparation.

The Daylight Requires Ownership

My new book that comes out early next year, The Upside Down Leader is rooted in this truth: Leaders don’t rise by avoiding the darkness. They rise by naming it.

Growth requires a strange combination of humility and hope. You turn around, look straight at the version of yourself you don’t want to be, acknowledge it… and then choose not to carry it any further.

You say:

“That mistake doesn’t define me.”
“That season doesn’t get to follow me.”
“That pattern might be familiar, but it’s not my future.”

You look back into the shadow, not to shame yourself, but to own the story so it stops owning you.

Then, and only then, do you look forward with clarity.

Planning becomes more than a checklist. It becomes a shift toward Daylight. The best version of your leadership. The healthiest version of your culture. The truest version of your organization.

Daylight is who you were meant to be before the world pulled you sideways.

A Few Questions to Ground Your Planning This Year

Here are some questions I use with leaders when they’re planning for a new year. Simple, but they open doors most people never walk through on their own:

1. What worked this year because of my leadership, and what struggled because of it? Don’t let yourself hide. Celebrate and own both.

2. Where did I lead from the Daylight? And where did I slip into the Upside Down? Patterns don’t lie. They just wait for you to notice them.

3. What am I avoiding that will follow me into next year if I don’t confront it now? Avoidance compounds. Courage compounds too.

4. If next year goes exactly the way I hope, who did I have to become to make that possible? Planning isn’t just about goals. It’s about identity.

5. Where did my team shine this year, and what kept them from shining brighter? Leaders remove obstacles or create them.

6. Who do I need to reconnect with, repair trust with, or re-engage before we step into a new year? Nothing grows in a fractured culture.

A New Year Isn’t Magic, It’s an Invitation

January won’t fix anything you refuse to face in December. But it will give you a fresh canvas if you’re willing to bring the truth with you.

You are not where you want to be. You are not yet where you’re going. But thank God you are not where you were.

Look back with reality. Look forward with hope.

And plan from the Daylight, not the Upside Down.

A new year is coming. Bring the brightest version of yourself with you.