Short time horizons keep it fresh

When do we do our best work? When we’re excited about something. Excitement morphs into motivation. We do our best work when we’re motivated. A great way to stay motivated is to work on something new. No one likes being stuck on a project that never seems to end.

The typical project

Long project waveform

The typical project starts out great but then our motivation and interest wanes as time goes on. It’s natural. Staying interested in a project over a long period of time is a challenge for anyone. The longer the project the thinner the tail. You’re not going to do your best work in the tail.

The ideal series of projects

Project series waveform

When you do a series of small projects, or break a single big project into smaller individual projects, you stand a better chance at maintaining motivation and rekindling interest. When you have a pile of tiny projects you get the chance to work on something new more often. We do our best work when we’re excited about starting something new. That’s why the bulk of our projects fit into cycles that last 6-weeks or less.

Credit for the waveform concept goes to Jim Coudal.

“Write drunk; edit sober”

A quote often (and probably inaccurately) attributed to Ernest Hemingway. And if you take the quote too literally, you’ll miss the power of what it teaches.

We have at least two sides when it comes to creating something.

On one, we see endless possibility. We can create anything our minds conjure. The muses are everywhere.

On the other, our brains are great at tearing down all the bullshit, and finding the kernels of what’s efficient. What’s practical. What’s actually good. And that side often doesn’t like what it sees of the other.

When I create, I try to take “Hemingway’s” advice.

To begin something I want to create, a blog post, a software feature, a YouTube episode, I’ll start from a thread of optimism. A motivating book. A TED talk that has me inspired to teach. A workout where I was able to push just a little further than last time.

I hype myself up to get closer to that feeling where anything is possible.

From there, I throw tons of stuff onto my canvas. I’ll write pages of run on sentences. I’ll code just to get the idea working. It’s not the best stuff. It’s not even good. But the goal is to get something, anything on the page.

Eventually, I’ll take a break. I’ll get a solid night’s rest. A walk. Lunch. Something to mark the change because it’s time to switch modes.

I start to edit.

I take all these things I created and pare them down.

What you see as 500 words today, started with 1200. The code you see tomorrow is the result of two dozen versions.

One thing I’ve noticed about editing is that I know I’m getting closer to something decent when the editing starts to hurt. When it feels like I’m starting to cut bone.

I start to throw away the things that I had previously considered good, in order to make room for what’s sitting on the canvas now. I remove that anecdote I was originally convinced HAD to be there. Or I realize no one is going to need this feature after all, even if it was the thing that had me most excited to start.

My best work comes when I balance my two selves — the one who can do anything and the one who’s my strongest critic.

When I find a way to invite both of my selves to a project, but make them work separately, that’s when things get really good.

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How shaking off the feeling of embarrassment helped this entrepreneur compete against a…

In 2010, a young wannabe entrepreneur, Michael, met a potential business partner. They struck up an idea, and by 2011, Michael put his entire life savings of $35,000 into starting the business. But $35,000 isn’t a lot, even with today’s create-a-startup-on-the-cheap-hosting days, and especially for this company — he wanted to take on Procter and Gamble. P&G probably spends that much a week on coffee.

How could this guy possibly make it?

First, let’s look at someone else who recently didn’t look like he was going to make it, professional golfer Jason Day.

Jason here looks like he’s drunk or falling asleep at the 2016 PGA Championship. Was he about to pass out?

No. This is just his pre-shot routine. Before every shot he closes his eyes and visualizes hitting a great golf shot.

What kind of effect has that had on his game?

In 2012, Jason’s career was imploding. He had his worst year since his PGA start in 2006. So in 2013 Jason started that pre-shot routine he crafted with a mental coach. That year he was the 17th ranked player in the PGA. Next year he was 10th. Then 3rd.

And now today in 2016, Jason Day is the number one player in all of the PGA.

But what really got my attention isn’t so much that he uses visualization. Lots of successful athletes do. Michael Jordan. Tiger Woods. Serena Williams. That’s a subject for another day.

What surprises me is that Jason Day actually had a visualization routine earlier in his career, but he stopped. He was embarrassed by what it looked like to other people. But when he overcame embarrassment, his career skyrocketed.

Our entrepreneur, Michael, happened to learn a similar lesson through a different route — improv.

For years before moving to California and starting that new business to take on Procter and Gamble, Michael had studied improv at the Upright Citizens Brigade (UCB) in New York. The UCB is an improv troupe which has at least one founding member who needs little introduction, Amy Poehler. Today the UCB churns out many promising comedians you see on Saturday Night Live and well known comedies.

One important piece of wisdom from the UCB is to get out of your head. Will Hines a member of UCB from 2009–2013 says this about it:

Getting out of your head refers to the desire to be doing improv without having your head full of rules and thoughts and worries.

Being in your head is that place where you become paralyzed with indecision. There are so many worries about how you’re performing and what people will think of you that you become frozen.

Will Hines mentions various pieces of advice on getting out of your head. The one that sticks out to me the most: “Beware of Trying To Please Just One Person (Who Isn’t You)”.

Do not get in the habit of letting your view of yourself be dependent on what someone else thinks of you.

Those classes and practice at improv gave our wannabe entrepreneur the training he needed to stay out of his own head, to make things without being paralyzed by possible embarrassment.

You see it in how comfortable Michael is in a video of himself talking about his product. Later he created a second product that made even his investors uncomfortable: butt wipes.

Those videos and products went viral. And just a few weeks ago Michael Dubin sold his company, Dollar Shave Club, to Unilever for $1 Billion.

I still struggle with the worry of what I look like in front of other people. Recently, I started a new YouTube vlog to share advice I’ve collected from over a decade of running my own businesses.

One day I was going out to lunch with some of folks at Basecamp (our parent company) and I thought about grabbing my camera. But I worried what it would look like on the street carrying this big camera around filming us.

I left it behind. I ended up having this great conversation about marketing new podcasts. It would have made a fantastic vlog post. I completely missed an awesome opportunity because I was worried about being embarrassed.

It’s not easy to shake off the nagging feeling of being embarrassed. Even when we know the thing we’re embarrassed by can make a positive impact on our well-being like Jason Day’s pre-shot routine. But the greatest success stories are people who shook off the worry of what they looked like in front of other people and just did their thing.

Somewhere in you is the belief that you are good… It is ultimately what will solve the problem of being in your head forever.

Will Hines

P.S. If you enjoyed this article, you should follow my YouTube channel, where I share more about how history, psychology, and science can help us create better businesses. And if you find yourself overwhelmed while organizing your own small business or handling customer support, check out how Highrise can help!

The first step is to start

Many people ask me, “How can I get started in web design?” or, “What skills do I need to start making web applications?” While it would be easy to recommend stacks of books, and dozens of articles with 55 tips for being 115% better than the next guy, the truth is that you don’t need learn anything new in order to begin. The most important thing is simply to start.

Start making something. If you want to learn web design, make a website. Want to be an entreprenuer and start a business selling web based products? Make an app. Maybe you don’t have the skills yet, but why worry about that? You probably don’t even know what skills you need.

Start with what you already know

If you want to build something on the web, don’t worry about learning HTML, CSS, Ruby, PHP, SQL, etc. They might be necessary for a finished product, but you don’t need any of them to start. Why not mock-up your app idea in Keynote or Powerpoint? Draw boxes for form fields, write copy, link this page to that page. You can make a pretty robust interactive prototype right there with software you already know. Not computer saavy? Start with pencil and paper or Post-it Notes. Draw the screens, tape them to the wall, and see how it flows.

You probably don’t even know what skills you need, so don’t worry about it. Start with what you already know.

You can do a lot of the work with simple sketches or slides. You’ll be able to see your idea take form and begin to evaluate whether or not it really is something special. It’s at that point you can take the next step, which might be learning enough HTML to take your prototype into the browser. The point is, go as far as you can with the skills and tools that you have.

Avoid self doubt

Many times the reasons we don’t start something have nothing to do with lack of skills, materials, or facilities. The real blockers are self-criticism and excuses. In the excellent book, Drawing on the Right Side of the Brain, the author, Betty Edwards, discusses how we all draw as kids but around adolescence, many of us stop developing that ability.

“The beginning of adolescence seems to mark the abrupt end of artistic development in terms of drawing skills for many adults. As children, they confronted an artistic crisis, a conflict between their increasingly complex perceptions of the world around them and their current level of art skill.”

At that age kids become increasingly self-critical and equally interested in drawing realistically. When they fail to draw as well as they know is possible many give up drawing at all.

This feeling continues into adulthood. We want to design a website or build an application but if our own toolset doesn’t match up to the perceived skillset we never start. It doesn’t help that the internet gives us nearly limitless exposure to amazing work, talented individuals, and excellent execution. It’s easy to feel inadequate when you compare yourself to the very best, but even they weren’t born with those skills and they wouldn’t have them if they never started.

Do — there is no try

People who succeed somehow find a way to keep working despite the self-doubt. The artist, Vincent Van Gogh was only an artist for the last ten years of his life. We all know him for masterful works of art, but he didn’t start out as a master. Compare these examples from Drawing on the Right Side of the Brain showing an early drawing compared to one completed two years later:

Vincent Van Gogh: “Carpenter”, 1880 and “Woman Mourning”, 1882

He wasn’t some child prodigy (he was 27 when he started painting), he learned his craft by hard work. If he’d listened to his own self doubt or despaired that his skills didn’t compare to Paul Gauguin’s it’s likely he never would have even tried.

This is all to say that there are many things that can get in the way of the things we should be creating. To never follow a dream because you don’t think you’re good enough or don’t have the skills, or knowledge, or experience is a waste. In fact, these projects where there is doubt are the ones to pursue. They offer the greatest challenge and the greatest rewards. Why bother doing something you already have done a hundred times, where there is nothing left to learn? Don’t worry about what you need to know in order to finish a project, you already have everything you need to start.

Originally published at, a blog by the team behind Basecamp, the world’s #1 project management app. Start 2016 (and your next project) with a free account.