The Year of Firsts: How to Lead Through Personal Loss

I was alone on a late-evening flight home to Minnesota, watching a show on Netflix, when a scene hit me so hard I completely fell apart. A character had just lost his father, and his coach walked up and said something simple: "This is going to be a year of firsts for you."

That was it. The emotions rained down. This was not a single tear rolling down my cheek. This was a full-blown, ugly splattering of emotion at thirty thousand feet. I may have even scared the person next to me.

The line struck me because I had lived it.

At the time of that flight, I was nearly four years into an estranged relationship with my oldest daughter, Abby. On Easter Monday 2017, she unexpectedly decided she didn't want to be in relationship with me or my family any longer. No contact. No warning. No explanation that made any of it easier.

And then the year of firsts began. The first birthday without her. The first Christmas. The first Father's Day. The first time someone asked about her and I had to find words. Every holiday, every milestone, every quiet Sunday afternoon carried a weight that people who haven't experienced it can't fully imagine.

My whole family went through it. My wife Jen. Our other six children. Each of us navigating our own version of that first year.

And then came the year of seconds. And thirds. And fourths.

Grief Doesn't Clock Out When You Clock In

Here's what most organizations don't understand about personal loss: it doesn't stay at home. It walks through the office door every morning with the person carrying it. It sits in every meeting, hums in the background of every phone call, and makes even routine decisions feel heavy.

When I was in the thick of my pain, I still had to show up as a leader. I still had to be present for my team, make strategic decisions, and perform at a level that justified my role. There were days when I nailed it and days when I was barely holding on.

The people around me at work had no idea what I was going through. Because I was hiding it — just like millions of professionals hide their grief, their loss, and their brokenness every single day.

Loss takes many forms. It's not always death. It can be an estranged relationship, a divorce, a health diagnosis, a child struggling with addiction, a miscarriage nobody talks about, a friendship that ended without closure. The common thread is this: something that was part of your life is gone, and the absence reshapes everything.

What I've Learned About Leading Through Loss

I don't have a doctorate. I don't have an MBA. I'm not a licensed therapist. But I've lived this. I've hit what I hope is my own rock bottom, and I went on a journey of healing. Here's what that journey taught me about leading through personal pain:

You cannot lead others well if you're not leading yourself first.

Self-leadership is where everything begins. Before you can show up for your team, you need to acknowledge what you're carrying. Ignoring it doesn't make it go away — it just redirects the pain into places where it does damage: your health, your relationships, your decision-making.

You need people, not just productivity.

When I was in the deepest part of my grief, the thing that kept me going wasn't my work ethic. It was the handful of people in my life who knew my story and refused to let me carry it alone. I have five men who I meet with regularly — a personal board of directors — who hold me accountable for my wellbeing, not just my performance. Everyone needs this.

The story you tell yourself matters.

For a long time, my internal narrative was one of failure. I failed as a father. I failed Abby. I wasn't enough. That narrative was poison, and it infected everything. Healing began when I started challenging those lies with truth. I did the best I could with the tools I had. I wasn't perfect, but I loved my daughter fiercely. And regardless of the outcome, my worth isn't determined by whether she comes back.

Healing is not linear.

There are good days and terrible days, and sometimes they're the same day. Six years in, I still have moments that knock the wind out of me. A song, a memory, someone else's daughter calling them "Dad" — these things still sting. That's not failure. That's being human.

Your pain can become your purpose.

The deepest pain of my life — losing my relationship with Abby — is the reason I wrote my book, the reason I speak on stages, and the reason I'm writing these words right now. I didn't choose this pain. But I can choose what I do with it. And what I've chosen is to help others know they're not alone.

What Your Organization Can Do

If you lead a team, manage people, or organize events, here's what I want you to take away:

Create space for the year of firsts.

When someone on your team experiences a significant loss, understand that the impact doesn't end when they return from bereavement leave. The year that follows is full of triggers — anniversaries, holidays, seemingly random moments that bring it all back. Check in regularly, not just in the first week.

Don't assume you know what someone is carrying.

I looked fine at work during the worst period of my life. Many of your people look fine, too. Ask the real questions. And when someone opens up, don't rush past it.

Normalize talking about hard things.

When leaders share their own experiences of loss and adversity — not for sympathy, but for authenticity — it gives the entire organization permission to be human. Vulnerability begets vulnerability.

Invest in the whole person.

Performance reviews are great. But are you also asking your people how they're doing at home? Do they have support systems? Are they sleeping? Are they OK? These questions feel uncomfortable, but they communicate something powerful: You are more than your output. You matter as a person.

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The Other Side

I want to be careful here. I don't want to wrap this up with a bow that minimizes the pain. Some losses don't get resolved. Some years of firsts lead to decades of carrying something heavy. My story with Abby is still unfinished, and I've had to find peace with that uncertainty.

But I can tell you this: the journey through that pain made me a fundamentally different leader, father, and human being. I listen better. I'm more present. I see people more clearly because I know what it feels like to be unseen. The worst thing that happened to me became the thing that opened my eyes to what matters most.

Everyone is going through something. Some people are in their year of firsts. Some are in their year of sixths. Some haven't even begun to process what they've lost.

Be the leader who notices. Be the person who asks the real question. Be present enough to hear the answer.

The little things mean everything. And sometimes, the most important little thing is simply letting someone know they don't have to carry it alone.

Frequently Asked Questions

How long does the "year of firsts" really last?

The term refers to the first year following a significant loss, where every holiday, milestone, and routine moment is experienced without the person or relationship for the first time. In practice, the intensity of the year of firsts evolves but doesn't disappear on a calendar schedule. The triggers become less frequent but can still surface years later.

How should leaders support grieving team members?

Show up consistently — not just in the first week, but throughout the following months. Check in with genuine questions. Offer flexibility without requiring the person to justify their need for it. And don't avoid the topic — silence can feel like indifference. Simply saying "I'm thinking about you" goes further than most people realize.

Can personal loss actually make someone a better leader?

It can, though it's not automatic. Leaders who process their pain, seek support, and allow the experience to deepen their empathy often emerge with a more authentic and connected leadership style. The key is not suffering in silence but engaging with the grief intentionally and allowing it to expand your capacity for compassion.