Sitting with Endings: A Different Kind of Year-End Reflection

This is not a year-end post about wins.

TLDR: If this year included loss, change, or quiet disappointment, you’re not doing it wrong. Endings deserve time without rushing to reframe. This is an invitation to sit with what’s finished before moving on. In this piece, I share some very personal endings, a framework I use, and a writing prompt that might help.

At the end of the year, we like to reflect on our successes: what worked, what we grew, and what we’re proud of.

Naming wins isn’t shallow; it can be a valuable reminder that we ARE actually moving forward despite sometimes feeling stuck. It can be particularly important for people who can get stuck in negative thought loops.

However, there is no shortage of places to celebrate. I’m seeing 2025 achievement lists everywhere on LinkedIn, in my email inbox, in Zoom gatherings, and in Slack channels. And we should reflect on success. Truly.

What gets far less airtime is what ended.

I’m not talking about the tidy kind of change we like to talk about. “I got fired, but I started my own business, and now I’m so much happier.” Not growth arcs or pivots that make sense in hindsight.

I am thinking about the things that just . . . STOP . . . sometimes quietly, often without your fucking permission, and leave you standing there trying to understand what exactly you are supposed to do with the absence.

That quieter kind of ending rarely makes it into a year-end reflection unless it can be reframed quickly. That’s ok, it can be too vulnerable to share.

The year is winding down. The shortest day of the year is fast approaching. Let’s make some space for endings.

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From 2023 through 2025, my life has been shaped by endings. There were beginnings too, of course. And yes, I can point to growth and redemption. But the endings have fucking loud, my friends. They have asked for more attention than I expected and more energy than I often felt I had to give.

Before I even start listing my endings, I want to rush to tell you I am okay now! I am better off! I have grown! They were all leading to a higher purpose! All true, but that’s now, with a lot of time and space and healing. Part of getting to that better place was sitting with the endings without trying to make sense of them too quickly.

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In 2023, my marriage ended. A serious hiking injury and nearly two-year recovery closed the door on certain kinds of physical movement I loved. My dog died. My oldest child left home.

Since then, there has been more loss. A job I cared deeply about came to an end. Some working relationships fell away. A personal relationship that did a lot of quiet healing for me ended painfully. I got fired from a fractional gig. Another fractional gig I loved and enjoyed came to a natural conclusion. Someone I loved working with got fired unceremoniously (and in my view, unfairly). My forties are about to end (I turn 50 in February).

None of these endings wrapped up cleanly or easily. These endings unfolded the way real ones often do, stretched out over time, tangled up with logistics, decisions, second-guessing, grief, and a lot of reliance on my ride-or-die people.

And here’s where I transition to work, because I think you’re reading this Substack not to read about how much my life resembles a country song but because of what I can share about making leadership more human.

Typically at work, we reward starts and beginnings: new strategies, initiatives, roles, pipeline, connections, careers, products, launches.

Endings, by contrast, are often handled quietly or not at all.

I have watched a senior leader leave in the middle of a packed quarter, their responsibilities redistributed in a spreadsheet that never quite gets discussed. There is a short all-hands with careful language. Then everyone is expected to move on. Nothing is formally closed; no one really says goodbye.

I went through an acquisition that completely changed the company's culture, led to massive layoffs, and meant several projects I was passionate about were shelved. The bright side: we all made some money! But we lingered so long on the bright side we never really dealt with the real grief of what was lost: the very fabric of a company we all loved.

(Buy me a drink sometime, and I’ll tell you about the utter douchebag who acquired us and how his antics reminded me of an SNL skit about a 28-year-old CEO in Silicon Valley. I think my non-disparagement clause has probably expired . . .???)

I’ve seen a product launch that people devoted literal sweat and tears to. . . fail. Just fall flat on its face with no explanation. There was a corporate pivot and a retro, but no real space for the actual ending.

A few months later, it showed up anyway. People hesitated. Energy dipped. Trust felt eroded, even if no one could quite explain why. The ending never finished, so it kept intruding on the present.

That residue-of-the-ending-that-never-really-ended becomes especially noticeable in December, when everything ir rushed and compressed. Everyone is so tired and overwhelmed, yet still trying to cosplay JOY and GRATITUDE and CHEER and SILVER LININGS and BRIGHT SIDES and QUOTAS AND GOALS AND ROI.

Many of the people I talk to every day are ending the year with a quiet grief they do not quite know how to name.

Maybe this is selection bias- people tend to call me when they’re having a hard time, not when they are high on life. Or maybe it is simply the moment we are in.

The people who call me are talking about work that disappointed them, identities that no longer fit, or a relationship to their job that has shifted without their consent. Sometimes they’re talking about how wider societal violence, political instability, and economic unrest makes acting normal at work feel impossible. There is no shortage of reasons to struggle this December.

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Over the last few years, I have been experimenting with a way of working with endings.

There are three parts:

1. Intentionality: Name the ending without dressing it up. This is over. This chapter is done. This role no longer exists in the same way. No rush to explain why the ending was good for you or what you learned or why you’re better off. No forced gratitude.

2. Processing: Tell the truth about what it cost and what it gave. Not the highlight reel version. The human one. What hurt? What do you miss?

3. Spaciousness: Resist the urge to fill the gap immediately. Let the quiet hang around a little longer than feels productive. Trust that something needs time to settle before it turns into clarity.

Teams need this space. Leaders need it. Organizations need it, especially at the end of the year. I’ve used this framework on my own and with individual clients. I wonder what would happen if a leader used it with their team and actually let everyone have feelings about an ending rather than just rushing to manage perceptions.

You do not need to make this year inspiring before you are allowed to leave it behind.

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If you want to explore an ending instead of skipping over it, here are a few writing prompts to sit with. Set a timer. Write without fixing or reframing.

• What ended for me this year that I keep minimizing or avoiding naming?

• If I said, “This is over,” what reaction would show up in my body?

• What did this ending cost me that I have not fully admitted yet?

• What did it give me that complicates the story I usually tell?

• What am I trying to outrun by staying busy or positive?

• What am I rushing to fill right now?

• What would it look like to let this ending stay unfinished a little longer?

• What might become clearer if I stopped asking this ending to turn into a lesson?

There will be time to celebrate. There usually is.

Endings ask for honesty first.

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Here’s a full writing prompt to help you explore endings (google doc).

Here’s the folder with all the writing prompts I use in my Inner Compass for Leaders and Work Pause workshops. (Google drive folder)

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As this year closes, I am not wishing you tidy endings or silver linings. I am wishing you endings that are honest enough to be felt, and slow enough to actually finish.

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Join Me for a Work Day Retreat

If this piece stirred something for you, you may want space to think instead of rushing to fix it.

I host small workday retreats for people navigating change, pressure, and uncertainty at work. They are quiet, facilitated spaces to slow down, reflect, and make sense of what is shifting, without needing to perform clarity or optimism.

After 18 months of offering them for free to hundreds of people, these sessions are moving to a paid model so I can keep the groups small and protect the container. The fee is refunded if you attend. You are paying to hold the seat. You get your money back by showing up.

Upcoming Sessions:

• January 9 – Clearing Space for 2026: Step back from noise and create room to think clearly.

• January 23 – Creating Boundaries at Work: Identify what you need to protect and where you are leaking energy.

• February 13 – Middle Age, New Ambitions: Explore how your goals and drive are shifting.

• February 26 – The Evolving Leader: Examine how your leadership identity is changing.

• March 6 – Managing Work Conflict: Understand your patterns in challenging conversations.

• March 26 – The March Work Pause: Reflect on the first quarter before moving into the next.

If one of these feels timely, you can find details and register here: