Not meeting your goals


I gave up daily vlogging recently. On January 1, 2017, I announced I’d start uploading a video every single day. There was no end in mind. Some people have taken on this challenge and lasted days. Some people have lasted years. I lasted a little over 3 months.

The breaking point was a company meetup at Highrise, a simple CRM company I took over from Basecamp in 2014. Our meetup was just a handful of days. But those days were optimized to spend every minute possible together since we’re all working remotely the rest of the year.

There was a lot of great footage from the meetup, but I didn’t have any time to edit fun stories together. Or think about pacing. Add music.

I shot YouTube live videos to at least get something out and keep my commitment to the daily vlog, but my YouTube stats started to tank.

So, I decided to focus on creating better videos — ones I thought could get the most likes and views — for each and every upload. My daily vlog became a barely weekly vlog. Sometimes I’d get two videos done in a week. Sometimes none.

And I started disliking the project more and more.


On the first day of my Sophomore year in high school, there was a “welcome students” event in our auditorium. I was barely paying attention but heard my name called out. Ugh, what’s this about? The dread became surprise and then elation when they announced I had the highest grade point average so far of our entire class of 400+ kids. Woah. I was not expecting that.

With this newfound ability to compete at having the highest grade point average, I just wanted to keep competing. Could I be my high school valedictorian in a few years?

That Sophomore year, I was in an AP (Advanced Placement) art class. For some reason the teachers and I did not get along. And I guess I didn’t have much talent with the art assignments. It showed in my grade for the class. My hopes for valedictorian were evaporating. It felt awful.

Junior year rolled around, and work just got harder. More tough classes, even less time for school work with all the extracurricular activities I was doing. My goal of having the best grades got worse.

My stress got worse.

But then I started making better friends with this guy, Al Wyman. Al and I had known each other since basketball camp in grade school. When we found ourselves in the same ethics class Junior year, we began talking more and more.

Those talks changed something in me. We’d banter back and forth about the books we were reading (or supposed to be reading for class) from the likes of Herman Hesse or Camus. And I realized how much I enjoyed our chats about “school work”. Not the competition for grades. But the act of learning, debate, application.

Why was I so focused on grades, when I should be more focused on the act of education?

In that ethics class, there was a project about the famous Edward Hopper painting Nighthawks: Redraw the painting and write an essay of whose in our version and why.

I experimented with the idea that maybe I could just focus on learning and enjoying the experience instead of getting the best grade.

But there was a catch. There wasn’t enough time to thoroughly tackle this project without pulling yet another all nighter. So I just didn’t do it when the teacher wanted it done.

After the project was due, I finally had an opportunity to focus on getting the project done and give it my all, learning even more about the original painting, and about the people I felt interesting enough to belong in my version. I turned the project in a couple days later and felt great about what I had learned and produced.

What happened was kind of a surprise. The teacher took it, looking at me a bit quizzically. I said, “Sorry I couldn’t turn this in on time. But here is my work. I hope I can still get some credit for it.”

A few days later he gave it back to me, with a great grade on it — even accounting for the points he took off for turning it in late.

It taught me a valuable lesson. I could still “perform well” without actually focusing on that as a goal. Really, I needed to take care of myself, and commit to a system of learning, not a goal of the best grades.

My time in highschool got so much better after that. There were multiple projects I started turning in late so I could get more sleep. And I learned so much more in the process.

I still ended up with a really high average when I graduated. I wasn’t the valedictorian. I was close, but it didn’t matter anymore. That last year and a half of high school was some of the best time of my life, and I got so much out of it.


If I look back at my career, the best moments are when I repeated what I did in high school — focus on systems, not goals. If I focused too much on where my startup would be when I wanted it to be there, I was miserable. When I focused on just showing up, learning as much as I could, delivering things our customers wanted on a regular basis, I enjoyed it, and we still got great results.

My first Y Combinator startup from 2006 didn’t turn into the mega-success I had envisioned, but became an enjoyable ride that still propelled my career forward and turned into even better and brighter things for others as well.

I had a goal with Y Combinator in 2011 to create a Groupon-sized success. Again I became miserable. Until I instead focused on a system of creating things that met needs I understood well because I had them myself.

That led to Draft, simple writing and version control software. It wasn’t the thing I envisioned making in 2011, but the system got me what I’d call a pretty wild success.

Now I run Highrise. The founders of Basecamp handed me the reigns when they wanted to spin it off. That was never a “goal”. How could it be? No one could have made it an intention. But this system of showing up every day and creating new things regularly got me here.


Staring at my YouTube stats was a mistake. There’s so much to getting traction, and so much of it isn’t under my control.

What I can focus on is showing up every day. Filming. Editing (when I can). Getting on camera. Trying to find a story from the day even if it doesn’t work out.

So I started daily vlogging again.

I sure as hell enjoy it more. And I think I might still get great results. Maybe not what I envisioned at first. But it seems like things have a way of working themselves out.

P.S. You should follow me on YouTube: here, where I share more about how we run our business, do product design, market ourselves, and just get through life. Also if you’ve enjoyed this article, please help it spread by clicking the below.

And if you need a no-hassle system to track leads and manage follow-ups you should try Highrise.


Basecamp running on a laptop

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