What I'm Worried About, And What I Am Not

Adding “worry” to the subject is mostly click-bait. You have to read it now. That’s marketing!

The purpose of these letters has been to help me better communicate what’s on in my mind, so you don’t have to guess. It’s also my hope that these letters give you confidence in yourself, in our team, and where we are headed. This has been a long year in many ways; frankly, I’m tired. I don’t want to write about the past after this letter. It’s time to look forward. With that in mind, this letter is to put the past…in the past.

What I’m Worried About:

Doing what other companies do [purely because they do it]: What attracted me to Apptegy seven years ago was a bizarre, contrarian approach to almost everything. Before signing my offer letter our founder asked me about the startup cliche, “What do you think about ‘move fast and break things’?” My answer was yes, do it, that’s what a startup is all about. He responded by saying that it’s wrong, that we should be more deliberate, and think deeply about the second, third, fourth… effects of decisions. That mentality is why I joined Apptegy (and the source of many frustrating days) and I believe when we think, really think, about those downstream effects we become more thoughtful and build the capacity to own the decisions we make. Keep thinking and challenge the “best practice” so we can, occasionally, create a “better practice.”

Putting process ahead of psychology: This is my concern for our team and for you individually. Yes, we need processes and, in the past, we over-indexed on non-systems. That said, psychology matters far more. Your psychology, or how you think about and talk to yourself, matters. The right psychology can handle the toughest situations in life and work; and it can build great processes too. But it’s rare that great processes build great psychology. I’m worried that we’ll go through the motions instead of challenging ourselves to our best work. Each morning, when you sit down to unlock your laptop with your password ask, “What’s standing in the way of me and my best work?”

2024 has also been the Year of David Whyte so here’s one more quote from him: “The marvelous thing about a good question is that it shapes our identity as much by the asking as it does by the answering.”

Measuring Metrics; Not Outcomes: See November’s team letter. I’ll add this, it’s unlikely that you’ll be proud of a metric 5-10 years from now. Instead you’re more likely to be proud of producing work that:

a) was truly unique

b) stood the test of time, and

c) challenged your psychology.

In 2025, we’re going to be more strategic. Metrics will help us know how we’re doing; but the whole purpose of a strategy is to create a result—an outcome—not a number or a percentage.

What I’m Not Worried About:

The future: “We’ll cross that bridge when we get to it.” I wish I could live my work-life in alignment with that phrase. Instead, my mind tries to cross bridges that aren’t here yet (and frankly, may never be).

One (of many lessons) I learned (and continue to learn) this year is to put my strengths to work on solving today’s problems—not tomorrow’s. We can (and have) figured it out when it arrives; no matter what it is. I’m not worried about our ability to build a new strategy or a way to change tactics to win at the strategy we already have. In case I’m not the only one, you shouldn’t worry about that either. Instead let today’s worries be your focus—meet them head on; but let the rest wait.

Team dynamics: We have a good team that cares about our work and about each other. I don’t communicate this as often as I should. I enjoy our team and am grateful that our work is about the work—not politics or status or blame. Let’s continue to assume good intent and help each other, especially as our pace quickens and as we hold each other accountable.

Our work going unnoticed: A year ago, it’s fair to say that we all had a bit of anxiety of being misunderstood (or worse, unnoticed) by the rest of the company. That doesn’t worry me in the least anymore. Our work stands out on its own. We’ve learned how to promote our work by making it visible. There is data and anecdotal evidence that our work is being seen too.

It’s great to be noticed. And yet, the reason that our work is more visible than it was 12 months ago is because we’ve connected to our colleagues and school leaders more directly than ever before. We’re doing good work by being intentional about who our work is for; and that’s the right reason for our work being difficult to ignore.

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After you’ve read this, come talk to me. I want to know what’s on your mind: What are you worried about? What are you not worried about?

When we come back to a new year, it’s eyes forward. Thank you for sticking it out this year. I’m grateful we get to work together.