Learning, Life Hacks, On Writing

Pattern Minded

 
My happy place is an art studio where all of the items have their own section.

I love to draw. Ever since I can remember I’ve created doodles, pictures, paintings, and other kinds of art. And it generally comes naturally to me – the kind of skill that other people call “artistic” and that I call “just drawing” – until it doesn’t.

I’m not sure what this gap feels like to people who don’t draw, so I’ll try to describe it in terms most people find easy to understand: imposter syndrome. When I don’t “feel” like drawing, I come up with every excuse to avoid that practice. I stay away from art materials and all of those wonderful colors. I stop drawing because there’s no chance of messing up.

That’s really not fun. Sometimes it has lasted for years. I am not sure of the first time I had this feeling but I would guess it happened when I enrolled in a Ph.D program in History instead of renting an Art Studio and drawing for a living. Maybe not drawing was a good thing, though.

If I hadn’t taken a break from drawing I would have spent much less time with computers. I might have missed out on learning to program. I might also have not engaged with new technologies like mobile and social and local commerce.

I am drawing again.

 It doesn’t take much to get started again on drawing. Just a little bit of time.
The hack that got me going again? Repetition. Small pictures. Doodling. Pretending “this drawing doesn’t matter.” Because the real benefit to creating and writing about it is a pattern itself – the self-reinforcing loop that happens when you make stuff, and look back later to see whether it’s good – and its absence is an anti-pattern.

So if you see me stop drawing, ask me to draw you something. Give me a commission. It doesn’t need to be paid, and it can be just enough to give me an idea. Making art pays off for me in many more areas of my life than the artwork I create. That process of making is a pattern that leads me to a place where I build amazing things. 

Life Hacks, On Writing

Future You Will Thank You for Handling Email Better

We get a lot of email – especially the kind we don’t want. The worst is getting email from sites that you don’t even know (when they got your details from the people that you did want you to send email originally.) How does this affect an average person? You might be spending 28% of your time just answering email, as this graphic from McKinsey demonstrates. That could be two or three hours out of every day.

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(source: http://www.mckinsey.com/insights/high_tech_telecoms_internet/the_social_economy)

I understand how this feels. I used to feel completely overwhelmed by email – and it was a constant game of “ping-pong” where when I received emails I would need to either delete, answer, or file them for later. Deleting wasn’t hard – it was easy to find the emails I didn’t really need to answer. Yet it was more challenging to store the emails I kind of wanted to read and didn’t need to act on.

My solutions for this organizational problem were to put everything in a folder. I then tried the “pomodoro” method of only answering email a few times a day for a set period of time. And I also tried answering all of the emails. None of these items really worked. I still ended up with a lot of email that I didn’t really want to read. And it seemed like it got harder and harder to unsubscribe over time. It still felt like I was wasting my time instead of either enjoying the email or just ignoring it.

Three actions solved my problem with email. The first was to turn on Gmail keyboard shortcuts. The second was to adopt Keith Rarick’s method of dealing with email using just a few shortcuts. And the third was to use Sanebox to automatically filter my email.

After starting to use Sanebox, I had two great benefits: first, all of my mail got filtered automatically into “News”, “Bulk”, and “Top” folders that I could also rename and train if I wanted (but frankly, I’ve just left it at the “set it and forget it” mode because it just works). And I also gained the “SaneBlackHole”, a folder into which I can drag any email that I never want to hear from again. There are lots more great features in Sanebox (works in any client, has lots of cool “snooze” and reminder features), but it’s worth it to me to subscribe just for the automatic filtering and the Black Hole feature.

Trust me, future you will thank you for trying it out. You can do that here.

Life Hacks, On Writing, Product Strategy

The hard thing about realizing it’s a hard thing

If you haven’t already picked up Ben Horowitz’s book The Hard Thing About Hard Things, you should. When I started to read Ben’s book, I thought that I already knew many of the things he would share, and that the payoff of reading the book would be learning about his particular struggle and viewpoint on startups. I was wrong. Full stop. Reading this book made me realize that when you’re working on a hard thing there are no easy answers and that you have to do everything you can to solve them. I knew these problems are hard – I’ve worked in startups before – but this realization was different.

Doing everything to solve a problem also means you don’t have the ability to solve every problem all of the time. You don’t have the ability to spend all of your time at work. And you don’t have all of your time available to be with your family. And you certainly don’t have time to be alone in your head not thinking about the problem. What you do have is the ability to work on the most important thing possible and to keep asking yourself at different points in the day, “Am I working on what’s most important?” Ben’s point is that you have to be brutally honest with yourself to know what’s important.

The meaning of important will change throughout the hour, day, week, and month. And the insight I gained from Ben’s book is that the most important thing isn’t always evident – it’s a combination of what you feel in your gut and the data that you gather – and you need to try very hard to stay true to that instinct. You won’t always be right, and it’s in fact guaranteed that you will make some mistakes. So what should you do when you realize you’re working on something hard?

You need to keep your body and brain going. That means that you need to eat right, get at least some exercise, and figure out when you can get sleep. When you’re working on a hard problem you often need to put in extra hours. If you put in extra hours every night you’ll run out of gas before you solve the problem. I’m not sure what works for you, but it helps me if those aren’t consecutive late nights. And family time? Yes, that’s important too. Turn off your phone. Turn off your laptop. Try your darndest to make some of your time real family time (no, not multitasking time, but actual family time.)

There are only so many hours in a day. If you want to spend your time solving hard problems, you will have to give up some of those hours to solve the problems. Make the hours you spend count. You’ll only know how hard the the problem was when you look back and see how high you climbed.

Agile, On Writing

Getting to the next big small thing

Startups are a constant tug between hyperbole and reality. One day you might be wearing many hats and completing a series of tasks that you didn’t know were on your plate that morning. Another day you might be thinking of the Next Big Idea. Which is real?

Both of these things are very real every day. When you work in a startup, the team is the sum (and occasionally, multiplied by) the individual actions the team does every day. The clock is always ticking toward the next big small thing.

One way to deal with the ups and downs of startup life is to treat every day as “one in a row.” Help your team. Move stuff forward. Repeat. It may sound trite and on the days when you’re less sure how to move things forward having a routine helps.

When you get a success story, celebrate! And keep moving things forward to the next big small thing you can affect today.

Life Hacks, On Writing

Write out the list of things you need to do

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You should do more writing when you’re thinking about the list of things you need to do. I wrote this list in longhand. That may seem strange in a world where we type practically everything, and I find it a particularly good way to organize my thoughts.

It is it productive to make lists? You might find it to be busy work, a useful skill, or just a procrastination effort. I find that making a list of things allows me to stack rank or highlight the most important things, remember when deadlines occur, and to see more clearly where the items fit together.

Writing text (or anything in longhand) is useful for a couple of reasons. First, it forces me to slow down – I can type faster than I can write these days – and makes me think. Seeing the words appear little by little on the page makes them feel more deliberate and considered. I believe it’s harder to commit to an idea when the information just appears (poof) fully formed from a cut and paste or other method. Writing the words out forces you to think about why the idea is there on the figurative page and what you really meant to say.

The second reason working in longhand is useful is that this practice builds in a guaranteed cycle of reading and revising. How often do you write something the first time, then upon reading it later wish you had taken the time to improve it? Even when I have trouble reading my own handwriting, I gain at least one editing pass to say the words out loud or in my head and to rephrase my thoughts. The first draft is not usually finished at the end of that first writing.

Finally, writing with a stylus (your choice – use a pen, pencil, chalk, whiteboard marker, or something else) activates different parts of your brain. Writing longhand gets you thinking in a more expansive way than typing or tapping.

Learning, Life Hacks, On Writing

This year, I learned to write

Photo by http://www.flickr.com/photos/jjpacres/
Photo by http://www.flickr.com/photos/jjpacres/

This year I learned how to be a writer. The easy part was deciding to start. The hard part was continuing to write. I don’t mean that any individual piece of writing was hard to start, or hard to finish. The hard part was realizing and understanding how much work there is to producing a great piece of writing, and knowing that much of the time, I wasn’t going to get there.

Unless I did get there. Much like the practice of drawing, writing only looks easy when you turn your head back at the body of work and say “that was good” or “that wasn’t so good”, and you have to do the work of writing to arrive at words that people want to read. This year I learned that whether you’re having a good day or a bad day doesn’t make the writing easier – it just makes it writing.

I thought I was doing a good job at writing before this year. Words, words, and more words have always been easy for me to produce. But not always words that conveyed meaning. When I left my last job I added “Writer” to my list of occupations – and started paying more attention to the craft of putting the words together efficiently, expertly, and beautifully.

Great writers (Orwell, Lamott, and White among them) sometimes explode off of the page and often state with absolute clarity facts and feelings. They bring intensity, passion, and verve to their craft, and it’s a joy to see it happen.

For next year, I want to apply this practice to other things that I do so that I take less for granted. When I talk to customers, I want the writing that I do to be as meaningful as the best essay I wrote last year. When I write emails, I want to make sure that the meaning is emerging in the smallest number of words that make sense. When I engage with my family and friends, I want to make those words matter even more than they do today. I’m certain I’ll often get my words wrong, confuse people when I think I’m being clear, and say different things than I intend. And I know I’ll be working at the practice of making them better.

Learning, On Writing

Is Blogging Still Useful?

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photo by http://www.flickr.com/photos/mariareyesmcdavis/

“What’s a Web Log”?
Once upon a time there was a Blog (web log). It was a place where you would go to read pithy insights, long form articles, and think pieces by people whose writing you respected. Over time this term was replaced and superceded by the simpler “blog”, which came to mean lots of things from “share a photo”, “create a domain name just to make a point”, and still “share interesting writing so that other people who care might have a good place to read it”.

Anachronisms happen fast.
The concept of blogging now seems quaint, like the rotary dial, a long-playing record, or a black and white tv did when I was a teen growing up in the early days of the Internet and computers. “Blogging” meaning “writing with the express purpose of placing your work in one place and finding an audience so that you can compete with other established publishers” now seems to be an outdated concept. The Blog is Dead.

The Conversation is Alive.
Yet there is this curious thing that’s happened to “blogging” or the activity we used to call blogging. Everyone who writes has turned into a syndication network of sorts, sharing almost everything almost all of the time. When was the last time you met someone who writes for a living and then learned that you could find their writing only in one place? In the same way that long form writing became “share photos in one place” and “share articles in another place” and “share random 140 character blasts” in a third, blogging no longer really exists.

There’s a paradox here. We’re both here having this conversation. It looks a little bit like a blog – having medium form content shared on a specific subdomain – and also has social features that allow you to upvote it (please do), share it, and comment about it. The blog has evolved from being an essay with comments to an almost constant conversation. To me this is a good change because it feels more like talking to other people.

What’s the use in blogging?
You might then ask, why write? There are lots of reasons to write every day (Dear Founders, Startups are Easier if You Write Every Day) and the most salient ones include:

  1. Get better at explaining your ideas to others – if you can’t form a few sentences that make sense to other people, you won’t be able to explain these same ideas in person.
  2. Explore a long-form idea over a series of posts. In the same way that you have a conversation with people over an extended length of time, your thoughts on a topic may change. Write about it – the results may surprise you.
  3. You never know who you will meet. Amazing people will find you because they read what you write. The possibilities are endless.