One of my common pieces of advice is that when doing something or making something, you should separate your planning into two distinct goals: - How good do you need the thing to be? - How good would you like the thing to be?

Most importantly, however, when you make it up as you go, you get to do what you think, not what you thought. All plans are rooted in the past — they're never what you think right now, they're what you thought back then. And at best, they're merely guesses about the future. I know a whole lot more about today, today, than I did three months ago. Why not take advantage of that reality?

And perhaps a bigger benefit, my brain can let it go when it’s done, and give my full focus to relaxing or doing housework or exercising. We talk a lot about work/life balance, and perhaps hobby/life balance is just as important.

I’ve never dreamed big enough. You know what happens when you’re too scared to dream big? Or when the circumstances of your life limit your imagination? By the time someone finally asks you what you want, you have no idea how to answer that question. You have to practice knowing what you want, just like you have to practice anything else. Can you describe your wildest dreams to someone else? Can you even describe them to yourself? Practice now. Why not?

Because we aren’t committing to a roadmap, we aren’t setting expectations. And because we don’t set expectations, we don’t feel guilty when that great idea never gets any build time because we decided something else was more important.

There is no clear winner, only an ever-changing list of survivors. Losing is just a failure to adjust and relate to the present context most directly.

The minute I created this roadmap, I felt more grounded, motivated, and in control. I can see the path forward, and I can see myself progressing down that path. It’s hard to overestimate how good this feels. So whenever I’m feeling overwhelmed, I ask myself: how can I create a feeling of progress? And it’s very hard to feel a sense of accomplishment if you aren’t clear on what exactly you want to accomplish.

The easiest way to do this is to map out your current habits and ask yourself, “Why do I do this?” over and over again—the way a little kid would. Usually, the things that feel like “goals” to us are 2–5 degrees of “why” removed from your daily actions.

I asked everyone what a successful outcome for them would look like…and what they would focus on, if they were doing my job. I want to gain some understanding of the choices that were made before I was employed at the company, but not to make any judgements about those choices. I might not necessarily be the smartest engineer in the room, and that’s OK. I know it takes a mixture of skill sets to build a great product. One manager admitted to me she was itching to see results, but admired my ‘maturity’ to do thorough research first.

(Dropbox mirror: https://www.dropbox.com/s/3k81gi7m03m72ua/Follow%20your%20heart%20%E2%80%94%20with%20caveats.pdf) The longer you sit and theorize the further you get from actually finding the answer. You need to get into the brute force business. And that’s something that I had to learn first-hand. One of the ways I’ve been able to tell if I’m doing something primarily out of a sense of obligation to someone else is to use the “relief” test: I imagine that the other person came to me and said, “I don’t think we should do this anymore.” If my anticipated reaction to that event is a sense of relief, then I know I’m holding on for the other person. If my anticipated reaction is sadness or regret — then I know there’s something else going on.

Ways to contribute to an operation in two rough buckets: Determine the work to be done. Do the work. Player-coaches fit right between the two. When you are determining the work, I think of it as being the DJ. You and/or a team are choosing what track to play, for how long, in what sequence, and at what time. This enables the individuals you manage to go and actually play that song.

When picking what I want to cut, I often take a good hard look at any big feature I'm working on and asking what the MVP of that feature-arc is. Often I'll cut parts of a feature-arc, vs an entire feature itself.

In the middle of my sketching hours, I don’t want to be worrying about whether I’ll be ready for my classroom prototype next month. Within a given day, action-oriented “butt-in-chair”-style advice does help; meta-thought is just distracting. But go too long without error correction, and you’ll misspend hours in the chair. ​ The rest of the day’s work becomes roughly deontological. I give myself permission to be satisfied with the day if I spent three focused hours sketching like I’d planned. ​ From time to time, I flip back into execution mode. It feels like an old friend. We say hello, dance for a while, and part ways smiling, just as it always was. Open-ended mode is more enigmatic, reserved—yet occasionally it sparks some moment so singular it lights up the whole year. Those moments don’t happen without the days spent together between those moments. I’m slowly learning to make the most of our quiet strolls.

I like structure. This is probably an understatement. I love overarching themes, identifying and creating patterns. I look for narratives. I want to know how each piece fits into an arc, has meaning and significance. I use a lot of anaphora in my poetry. ​ I thought a vacation would be the end of my exhaustion. I went to Alaska very tired, and I came back less tired.