I read a lot of year-end posts in December. Most of them are victory laps dressed up as reflection.
The wins get listed in detail. The losses get listed only if they make a tidy comeback story. The hard moments get smoothed over into "lessons learned" so quickly that the lesson never quite lands. By the time the post wraps up, the writer somehow looks more impressive than they did at the top, which is a neat trick when the actual point is supposed to be honesty.
I am not going to do that this year. I have been writing this series for fifty weeks now, and you and I have spent enough time together that I owe you a different kind of post for week fifty-one. Here is my list. No spin. The things I got wrong in 2026, the patterns underneath them, and what I plan to do about it.
If this lands the way I hope, it gives you permission to write yours.
I let one client situation drag too long
Mid-year we had a client engagement that was clearly off track by the end of Q2. The project manager flagged it. The team flagged it. I had three separate conversations with the owner where I should have either reset clean or ended it.
I did neither. I kept hoping the next milestone would settle things down. By the time we finally had the hard conversation, three more months of team energy had been spent on a relationship that was not going to recover. Two of my best people were quietly burnt out by the time we walked away.
The pattern is the one I have written about in this series and apparently still need to learn myself. Avoiding the conversation does not buy you time. It costs you time. The bill always lands on the people who can least afford it.
What I am doing differently in 2027. The first time the team flags an engagement as off, that is the trigger for me to schedule the conversation. Within ten days, no exceptions.
I overestimated my own bandwidth twice
I run two organizations. The agency I started in 1999 and a chief of staff role at a church with about two hundred and fifty staff. That is more than one person can carry well at the same time, which is why the team on both sides matters.
Twice this year I told myself I could personally take on something the team should have handled. Once at the agency, once at the church. Both times I told myself it was a unique situation. Both times I was actually feeding a quiet appetite to be needed, dressed up as leadership.
The cost was not catastrophic. Both projects shipped. But I lost weeks of margin that should have gone to the people who live in my house.
What I am doing differently in 2027. When I notice myself reaching for work I should have handed off, I write the actual reason on a sticky note. If the reason is "I want to feel needed," the work goes back.
I was slow to say I was wrong on a strategic call
I made a call in the first half of the year about how to position a service line at the agency. I felt strongly. The leadership team had questions. I held the line.
By the end of Q3 the data was clear the call was wrong. Just wrong enough we needed to reverse course. I held it for another six weeks longer than I should have because admitting it meant unwinding decisions that had stacked on the original one.
Here is the part that bothers me. I wrote a whole post in this series about being willing to be wrong. I still slow-walked the actual moment when it cost me something to apply it.
What I am doing differently in 2027. The leadership team has a quarterly "where is Jay slow-walking it" review on the calendar, with permission to point at the thing I am protecting.
I underestimated the speed of the AI shift inside my own building
This one is humbling.
I have been writing about the AI shift all year. I run a team using these tools every day. We have rebuilt internal workflows. I have written a book on it.
I still got caught flat-footed twice by the speed at which a capability went from "interesting demo" to "this is the table-stakes way our team works." Both times the team was doing something differently for weeks before I caught up. Not because they were hiding it. Because I was assuming I knew how fast the curve was moving and the curve had moved past me.
The lesson is that being early in one moment does not protect you from being late in the next. You have to keep paying attention or you become the leader who was loud about the right thing two years ago and quiet about the right thing today.
What I am doing differently in 2027. Monthly time blocked to use the new tools myself, hands on. The leader who is not using the tools cannot lead the team that is.
The pattern underneath all of it
Read all four of those back to back and the pattern is the same. I knew the right answer. I taught the right answer. I just did not always do the right answer in time.
That is the gap I want to close most in 2027. Not knowing more. Doing what I already know, faster.
- What is the conversation you teach others to have but slow-walk yourself?
- What boundary do you draw on paper and bend in practice?
- Which client, project, or person have you been hoping settles down on its own?
- Where did you reach for work that should have stayed with the team because you wanted to feel needed?
- Where is the curve in your industry moving past you while you assume you are still ahead?
What is on your list?
