Operation 100, 108 Days In
My goals this year focused on creating habits in the hundreds. Here's how it's going. | Team Letter | April 19, 2026
April 19, 2026
There’s a famous story by Brad Isaac about meeting the comedian Jerry Seinfeld. Isaac was a software developer and aspiring comedian, and he recalls that at a comedy club one night, he Seinfeld his advice for a young comic. The answer was this:
1. Purchase a large, one-year wall calendar and a thick red marker.
2. Every day that you write (even if it’s just one joke), put a big red ‘X’ over that day’s date.
3. After a few days, you will see a chain of red Xs. The only goal is to not break the chain.
It’s the premise on which a lot of modern productivity advice is based — little habits, done often, create little gains that add up to big change. It’s what our work is based on too — Little Wins, anyone?
So, back in January, you may recall that I asked you the question “What will you do 100 times this year?”
Our company goals are fantastically audacious and I think the best way to achieve them is with great habits — things we do every day. So my personal goals for the year are centered around creating excellent habits that make the work of building a successful company and a healthy personal life feel less like a Big Initiative, and more like muscle memory.
Last week we saw the 100th day of the year (can you believe it!?) so I took a moment to take stock of what I set out to do this year, where I am on those habits, and how I might focus or change for the next 100. Yes, I made a sticker chart. It’s fine.
Here’s what I’ve learned so far, personally:
Mondays are where I shine. I start off the week really strong in my habits and find myself waning by end of week, and sometimes crashing into the weekend on Fridays. I think figuring out how to get a bit of a reset mid-week would help even this out.
Habits really do stack. James Clear taught us this in Atomic Habits and it’s always made sense in theory to me: creating a small habit and then attaching another one to it creates a high impact chain reaction. When you have a habit to see the sunrise, it’s much easier to add a 1-3 mile run each morning, because you’re awake for it! What I found in my data so far this year is that I have days where I knocked out 7 or 8 of my habits, and days where I put up 0. I’m excited to see what I can easily add to my established ones to stack some more, especially in the areas that I’m scoring low today. Like eating breakfast.
Habits need accountabili-buddies. Well, at least MY habits need friends and family to help me keep them. Every habit I have successfully built up this year so far, I’ve done with at least one other person. I talked to 60 potential customers because our team diligently set meetings for me. I see the sunrise most days because I’ve committed to meeting running friends at the gym. One of the most powerful things I can do going forward is to just ask one person: “Can you help me with this habit?” That’s easy enough for anyone to do. Need a buddy for a goal? Ask me, please! I’m honestly so grateful for those who are helping me with mine.
What I’ve learned has already been helpful. But like all habits and goals, the key is to a) keep working on them with honesty and transparency; and b) edit them based on what you learn. Here’s how my next 100 days of the year is focused:
I’m keeping the real goal first. Consistency without quality may be counterproductive, it turns out. I’ve run 108 times this year, but if I’m being honest, sometimes I got out there for 1 dumb mile just to keep the streak alive. It did the job of creating the habit, but it did not improve my running, like at all. On running and strength, I’m shifting my focus to “quality workouts every day,” and working with a coach who can actually help me improve. Running garbage miles wasn’t getting me to my real goal, which is to improve my running and my fitness.
The real goal in the company? Growth. If what we’re doing isn’t working, the answer is not to say “that’s not working” — the answer is to make our own luck. We learned that in Nashville, and we’re bringing it front and center this quarter.I’m asking for more help. More buddies, please. For the next 100 days, I’m looking for ways to engage more people (and more robots?!) in my goals, and to stack them in smart and creative ways. I started this week by asking my friend Claude for help with coming into conversations with potential customers with a greater level of hospitality, and it’s amazing what’s possible.
I’m tracking what’s easy. I’ll drive myself nuts if I try to keep track of or write down every time I make dinner for my family or text or call my parents. So, while I’m keeping some of those “hard to track” goals in mind and looking back at them regularly, I’m not tracking it all. I’ll track what’s already being recorded on my watch and my work apps, and “gut check” the rest.
(Also, using Claude to analyze your goals against your Strava exercise data, Garmin sleep data, NYT Crossword data, and Hubspot sales data? Nice little Saturday morning. Highly recommend.)
I’d love to know where your goals are this year, and how I can support you with them! Let’s grab coffee after sunrise but before customer meetings start and talk about it — it’ll be a stacked habit we’re both proud of.
Let’s go, Alpaca — big things to do!
KB
PS: Were you wanting the actual score card? Here are my current stats on the “hundreds” I set forth.
Work Goal: Our company’s goal is to grow customers, revenue, and team by 100% in 2026. The things I PERSONALLY want to do toward that goal:
100 meetings with education leaders: Currently at 55 held meetings with education leaders, 2 podcast recordings, and 3 customer meetings, so I’m counting 60 total. Good start for the year, but we can do more.
100 handwritten thank you notes: I’m at 10. This one needs work. Perfect candidate for habit stacking — adding 15 minutes for this practice after interviews, meetings, and demos would be easy enough.
100 new customers: So far, we have added a little more than 20 new customers, so we’re sliiiiightly off where I wanted us to be by April. Not to worry, we’ve got a team, a plan, and a great leader to help us get there (and so much more).
100 returning customers: It’s renewal season now! So this work is just beginning.
100 published posts/articles: Well guys, this one has fallen short, with just 13. Time to fire up the writing a little more often.
100 investor conversations (current or future): I’m so lucky that we are at 20 here, but closed our bridge round in record time!
100 team 1:1s: If I’m counting correctly, I’m at 38. My favorite ones this year? Hands down, it’s Excel School, the every other week mentoring meeting I do with Kaitlynn to discover how we can be more AI and data conversant in every aspect of our work. (It started off in spreadsheets but we’ve evolved!)
PERSONAL
Personal Goal: Be consistently ready to run a half marathon (healthy, strong, nourished), enjoy excellent relationships with every member of my family, and take care of myself.
Hit a 100 day running streak: I technically didn’t do it yet. I ran 100 days in the span of 102 days, but I missed 2 days due to international travel.
100 breakfasts: I think this number sits at 4? I may need a breakfast streak.
100 strength workouts: Started off a little slow, so I’m at about 12. This is a big priority for me this spring!
100 pre-10 pm bedtimes: Possibly my worst data point besides breakfasts. I have 12.
100 sunrises 🌅 CRUSHING IT! at 78 so far this year. Being up early is the literal best.
100 pieces of art made (any size!): Failing it! I’m at 5. Maybe 6, if you count the sticker chart that I made for my goal tracking. Thanks to Marina for making art part of our birthday happy hours, though! Those are 3 of my 5. (Wait Marina did you do that on PURPOSE!?!? You probably did.)
100 books read: This is a ridiculously audacious one, but I’m at 13. Did you want my favorites? Thank you for asking! Fiction: Theo of Golden. If anything surpasses it this year, I’ll be shocked. I loved it so much I’ve read it twice already. Non-Fiction: Unreasonable Hospitality. You won’t believe how this changes your mindset at work, honestly.
100 NYT crosswords completed: I’m at 62, and I’m quite pleased with this new habit in my life. It helps me feel sharper, it’s a fun thing to do with a friend, and the New York Times games app is just incredibly encouraging.