Startup Lockdown — Day 5 — Goalie

Day Five was our broadest day. We started from the idea of “using your time better” and “doing tasks when you’re at the right energy level.” This somehow related to time usage and major goals.

For me, it was also the toughest. After four days of focusing from 9am — 8pm, it was hard to get the energy at the same level.

Fast & Slow Time

We tried to get a balance of the processes on this day. We had the idea of having some time that was talk, which was “slow” — and then some time that was pure execution that was time boxed very specifically.

I don’t think we optimized it as much as we would have liked to, but it was harder by Friday. If I were starting on a Monday again, I’d try to include this.

Designated Breaks

Day Five was also the first time we followed our designated breaks. Our photographer got goofy and asked us to juggle lemons, which ended up being really fun. If I were doing this again, I’d include designated breaks with wacky activities.


This was also the first one where we didn’t just have “normal” and “extreme” users. We also managed to talk to an industry expert, Leslie Perlow, a professor at HBS.

You can watch her TED talk here. Perlow’s work centers on the idea of how you have better balance in terms of achieving both professional and personal goals — and around having a shared team mentality for doing both.

This helped us move from the idea of interviewing individuals about their calendar, to how our tool might fit in for groups of people.

Idea Iteration

This was the day we iterated the most on the idea. We talked about times of day, energy levels, how necessary tasks were, “types” of tasks, long term goals, medium term goals, priorities, and “elephants” (our catch all word to try to express that not everything is a task or a goal). We talked about how these things are used in teams vs for individuals.

We sketched the most “different” products on this day, and also spent the most time exploring other calendar/task products that were available.

Consumerization of the Enterprise

This was also the first day we spent more time thinking about a specific trend in products. Caitlin brought in a lot of experience from having looked at many different deals involving individuals bringing tools to the enterprise.

We also learned that semantics matter a lot — these were some of our tensest arguments, even though it turned out we were all in relative agreement.

Personal applicability

This day was also fun because it was personally applicable. While we were working, I cleaned off my computer desktop (it feels so much better now!)

I also got to test out our frameworks using my calendar — so now my events are colored by:

Have to/want to
Have to/don’t want to
Want to/don’t have to
Don’t want to/Don’t have to

Just being able to see my calendar and how I feel about the events per week makes a big difference for me.

Sloppiness at the end

The last part is that we definitely got sloppy by the end. We accidentally made our logo the Windows logo. We moved more slowly. I can attest that the quality of my work Friday afternoon was rock bottom for my week.

I spend a lot of time thinking about “finishing strong” — but I definitely didn’t manage to this time around.

Final Product: Your Goalie — a way to re-evaluate your calendar based on what you want to do, and what you have to do.