(Not) Shipping is a Virtue

One of the most important Basecamp features I ever designed never actually made it into the product.

Back in 2009, I designed the due dates for To-dos feature in Basecamp Classic (looking back it’s hard to believe Basecamp was without due dates on To-dos for its first 5 years!). Shortly after we thought it might be useful to see those due dates on the two-week calendar that appears at the top of your Basecamp Dashboard.

Basecamp Classic’s Dashboard shows upcoming dates over the next two weeks

It seemed pretty straightforward. We’d need to design a way to display any dated to-dos alongside your milestones while making them visually distinct. We’d need to figure out what to do if you had too many to reasonably show at once as well as what happens when you click one. A very typical feature brief. We spent about a week going back-and-forth until we came up with a pretty nice solution.

This is my original mock-up showing our solution for mixing Milestones and To-do due dates on the Dashboard.

Later we figured out how to deal with collapsing the items when there are too many to show at once

… and we designed an overlay that displayed the full details when you clicked one.

Everyone felt good about the direction so former Basecamper, Josh Peek, and I set off to build it out and got everything ready to ship—all that was left was to get a thumbs-up and run a database migration. So we let the rest of the team know we were ready and then… *crickets*.

At first I remember being a little worried. Did they miss my message? Was it no good? Was anyone paying attention? Then I realized: it didn’t matter. You see, there wasn’t a manager with crossed arms tapping their foot; no due date; no client itching for it; no schedule pressuring us to move on to the next thing. There was no external pressure at all and the feature wasn’t making a case for itself.

So now what? We’d done everything right. We had an idea for a useful addition to Basecamp and so we worked hard to come up with a good, solid design. We felt good enough about the feature to fully implement it. This is what we do in product, development, right? We come up with ideas for making the product better, we design, implement, test and… ship. I mean, we did all that work? Shipping is the period on the sentence of product development! But we didn’t ship this and it’s still not in Basecamp Classic today.

Why not?

Everyone at 37signals knew we’d been working on this (we were a very small team), we used Basecamp all day, every day and nobody ever said, “Man, I really would have liked to see that to-do on the calendar…when’s that finally coming?”. Customers weren’t asking for it either. As time went by, the feature branch was still in my local Git repo, but nobody ever mentioned it again.

It was good, probably useful, it might have even made some customers really happy and we spent weeks working on it. I believe most companies would have shipped it so why didn’t we?

Every feature has hidden costs. Some are worth the cost—sometimes many times over—but others only drag your app into the red. One more thing on the screen you can click, one more option, another setting, more decisions for users to make (Kathy Sierra calls this cognitive load). Your app gets slower and customers notice it feels slower. Designers have to juggle more pieces. Development gets more complex, difficult, and time-consuming with every new piece you bolt-on. That’s a lot to ask of a feature that’s only fine.

Shipping != Success

I think about this feature often. It’s probably the most memorable one I’ve worked on because it never shipped. It reminds me that what’s important isn’t how much time I’ve spent or how hard I’ve worked because those things have no bearing on its value to customers. Sometimes you have to get real before you can tell if your design is working, sometimes you’ve got to build it out. It’s a clear sign of a healthy process when you can say “no” and move on at any stage. It takes maturity to not count it as a failure but see value in the lesson. It says a lot about a company that values more than sunk cost.

If projects that ship are the only ones that are deemed successful then you’ve set the bar pretty low. Who’s going to ever risk trying a radical idea, invent a new technique, imagine an original interaction, or try anything at all that isn’t a sure thing if there is any chance they’ll be deemed a failure? Who will risk missing a deadline, going over budget, or trying something that ultimately just doesn’t work? If your goal is always to ship, you’ll probably do a lot of that but it won’t be your best work. Besides, who wants to use a product where every idea ships?

The Homer

Because everything happened in Basecamp I was able to go back and review this nearly 7 year old project, read the entire conversation, and find all my design mock-ups. If you can’t do this with your work, maybe you should be using Basecamp, too. Your first one is free when you sign-up today.

What’s new in Basecamp 3.2 for iOS

The latest version of Basecamp 3 is available today in the App Store! If you Basecamp on iPad we think you’re going to be particularly pleased. Here’s a quick look at what’s new…

When I’m not drawing, I’m making Basecamp 3 for iOS with Dylan Ginsburg, Zach Waugh and the rest of the team at Basecamp. It’s also available on Android, Mac, and Windows — anywhere you’ve got a web browser and an internet connection. Your first Basecamp is completely free so try it today, it takes just a minute to sign-up.

What’s new in Basecamp 3.1 for iOS

The latest version of Basecamp for your iPhone and iPad is here and it’s the most significant update so far in 2016. Here’s our latest GIF-injected look at what’s new…

Don’t take our word for it—launch the app and the Happy Camper will show you what’s new. He also likes reviews. Seems a little needy to me, but throw the guy a bone, would you?

Add the Basecamp 3 widget to your Today screen to see upcoming events from your Basecamp schedules and to-dos that are due soon. It also has a row of shortcuts to a few of your most relevent Ping and Campfire chats. I use it all the time to jump right into chats and to-dos from my phone’s lock screen.

Add Basecamp 3 to your Today screen to see what’s coming up and get quick access to chats you frequent.

We’ve also introduced a new and improved full-screen experience for writing and editing comments. It’s far less cramped and distracting. Need to peek back at the previous discussion while writing? Just tap on the preview at the top!

Write and edit comments in the new full-screen composer. Just tap the preview at the top to peek back at the thread for reference.

Smart people who use 1Password to make their lives easier and more secure can now use the 1Password extension to log in to Basecamp on iOS devices. I mean, don’t let me stop you from typing out 3PmL&nopav23)E#ohqa/ if that’s your thing (not my real password, don’t be creepy).

Basecamp loves easy and secure log ins. You should, too.

Google Docs
Google Docs, Sheets, and Slides in Basecamp now open with their apps (instead of Safari) if you have them installed.

Smoothly move between Basecamp and your Google Docs.

My new friend Rajiv (real name, don’t be creepy) is super happy about it:

Thanks for v3.1! 
A well deserved app store review is coming right up…

– Rajiv Sinclair

Now you can select an image that was copied to the clipboard after tapping the attachments (paperclip) button. The clipboard image is called-out specifically in the recent photos row with a special style.

The first image in the recent images list is from the clipboard. Copy and paste in Basecamp has never been so easy!

And more!
As always there were tons of small improvements, polishes and bug fixes. Every app update ever mentions these non-specific improvements so they might be easy to overlook but they are super-important for keeping the app fast and crash-free. It’s not exciting or sexy work that garners tons of applause but please tell the very much sexy Zach Waugh and Dylan Ginsburg know how much you appreciate their continuing to make this work a priority.

♥️ Team iOS,
Dylan Ginsburg, Zach Waugh, and Jason Zimdars

Basecamp 3 works where you do on iOS, Android, Mac, and Windows — anywhere you’ve got a web browser and an internet connection. Your first Basecamp is completely free so try it today, it takes just a minute to sign-up.

The latest in Basecamp 3 for iOS

Hello again from Team iOS here at Basecamp! We’re spent our spring making Basecamp better for you—here’s a GIF-powered look at what’s new…

Mark all as Read
Last time we introduced a way to swipe individual unread items on your Hey! screen to mark them as read (you know, like when you ✌🏻read✌🏻 Great Expectations in high school). Now you can just tap and hold on the Mark all as Read button to completely clear everything in your Hey! box.

Quick jump
Tap the Basecamp’s title in the Navbar from most any screen to quickly jump to another section in the same Basecamp. It’s handy when you’re looking at a to-do, for example, and you want to jump up to see all the the other to-dos.

Peek and pop
If you have an iPhone 6s or iPhone 6s Plus with 3D Touch you can use Peek and Pop on unread items to preview them.

Login options
There are several ways to log-in to Basecamp and now you can manage them right from Basecamp for iOS. Tap your avatar on the home screen, then Login options to set a password, change your password, and enable or disable Google log-in.

All the sharing
The share action is now available on every screen in the app. This sends you to the iOS system Share Sheet where you can copy the URL or send it to another app or extension. It’s particularly handy for copying and pasting a link to something elsewhere in Basecamp to a comment.

Sneak peak: @mentions
With summer approaching we’re already hard at work at the next round of updates and a big one on the list is full support for @mentions in Pings and Campfires. We’re already testing it interally and it’s a huge upgrade—we can’t wait to put it in your hands. Here’s how it looks so far:

Basecamp 3 for iOS is always free, get the newest version with all these goodies in the App Store. Thank you so much for using Basecamp and please let us know in the comments how Basecamp is working for you on your mobile devices and how we can make it better.

♥️ Team iOS,
Dylan Ginsburg, Zach Waugh, and Jason Zimdars

Basecamp 3 works where you do on iOS, Android, Mac, and Windows—anywhere you’ve got a web browser and an internet connection. Your first Basecamp is completely free so try it today, it takes just a minute to sign-up.

Until the End of the Internet

On software and services built to last

Illustration by Nate Otto.

At Basecamp we think a lot about the long-term. The company has been around since 1999, the product since 2004, and we even offer our employees benefits for the long run that put their health and long-term happiness before maximum productivity.

It was with this kind of long-term thinking that we launched the first major new version of Basecamp (in 2012) as a brand new product rather than foisting it on everyone as an upgrade. 2004’s Basecamp Classic (as it’s now known) continues to work just as it always has and we’re happy for customers who prefer that version to keep using it as long as they’d like. Change is hard. Particularly when you’ve got deadlines, clients, and work to be done. Suddenly waking up to a completely new version of any software can be so disruptive that some customers waited months or years so they could move to the newer version on their terms. Many others have happily stayed with Basecamp Classic and have no interest in upgrading at all.

When Basecamp 3 arrived in October 2015, it similarly launched as a brand new product. There is no pressure for customers on Basecamp 2, or even Basecamp Classic, to move to the new version. All three Basecamps are here to stay.

How we got here
For our first 15 years in business we were called 37signals. We changed our name to Basecamp in 2014 to reflect a new focus on our most popular product and at that time made the hard decision to stop selling our other products. Ta-da List, Writeboard, and Backpack all stopped accepting new customers but for those who have been relying on these products for years they continue to work just as they always have. We became dedicated to supporting them forever (or until the last customer turns off the lights). Internally we’ve come to call this policy Until the End of the Internet and though we’ve only announced it publicly for Ta-da List we’ve been operating as if it were true for all our apps ever since. Today we’d like to make it official.

Until the End of the Internet is a promise
Internet software and services disappear all the time because of whimsy (“changing priorities”), acquisition, financial failure or worse. It’s become a risky venture to place your trust and data in services that could disappear at any moment, for any reason, and with no guarantee that your data will be safe, preserved, or even portable. We’d like Basecamp to stand against that.

Here’s what that means:

  • The day you become a Basecamp customer you can trust that Basecamp will be around. In the event that the Basecamp product you’re using enters a legacy phase you can keep using it, as-is, indefinitely (assuming you continue to abide by our terms of service and keep your subscription active).
  • Your data is safe. Regardless of status, all of our products receive the same rigorous care when it comes to security and privacy. While we may not add new features to legacy products we’ll continue to apply the latest security updates; maintain the infrastructure that keeps them safe, fast and secure; and continue to offer customer support. Have a question about Ta-da List, fire away!
  • Basecamp is our life’s work—we’re in this for the long haul. In the unforeseen and unanticipated event that the company or one of our products is acquired by another company, we’ll do everything in our power to make sure the product and this promise live on.

Permanence, Trust, and Legacy
When they launched, each of our products was our finest work. They were the result of countless hours laboring to build software that is simple, clear, easy-to-use and honest. They remind us where we’ve been, how we got here, and point to where we’re going. We’re proud of these products and honored by all the customers who have supported us over the years, who made our tools partners in their success, and who continue to rely on them every day. This isn’t free or easy but we believe that standing by our customers and our products is the right thing to do.

Basecamp, built-to-last since 1999.

For more details about this policy visit basecamp.com or contact us.

What’s new in Basecamp 3 for iOS

Hello from Team iOS here at Basecamp! We’ve been hard at work making Basecamp better for you, here’s just some of what’s new…

Better sharing
Basecamp 3’s share extension has been redesigned and powered-up. Post a funny GIF in a Campfire, Ping Zach that URL, or drop a PDF into Docs & Files all without leaving the app your’re using or launching Basecamp at all! Basecamp even remembers the places you share to most. If you haven’t yet made this part of your Basecamp workflow—definitely give it a try.

Share from Photos or other apps on your iPhone, then choose where to save in Basecamp.

Pin me!
Now organizing the Basecamps and Campfires you use most is much easier. Pinned Basecamps and Campfires stick to the top of the list for quick access—just tap the pin. Now, for instance, you can easily jump into a Campfire even if you’re not following it.

Pinned Basecamps and Campfires stick to the top of the list for quick access.

More control over what’s new
Our Basecamp is a busy place, every day there are tons of new notifications about new Pings, comments, @mentions or Campfires. Swipe on any unread or recent item to see more options for dealing with it quickly. Swipe and Mark as Read to clear it or tap Unfollow to prevent any further notifications from the thread. Make a mistake? You can always swipe to Mark as unread and pop it back into the unread list.

Swipe from the right for quick actions: Unfollow, Mark as Read, or Mark as Unread.

More fun!
Basecamp is a serious tool for getting work done but that doesn’t mean you can’t have a little fun with your team. Basecamp 3 for iOS now supports third-party image keyboards like Bitmoji, KIMOJI and all of your various moji-based keyboards (you’re welcome, millienials!). In fact, you can simply paste images (Hello animated GIFs!) right into Pings and Campfires, too.

Who says work can’t be fun?

And that’s not all…
Swipe-to-go-back is even easier (just swipe toward the right on any screen to go back, not just from the left edge)… see who’s been talking in new Campfire activity… a brand new flow for starting new Pings (even with multiple people)… plus tons of bug fixes and behind-the-scenes improvements to speed and stability.

See who’s talking in Campfires (left), Swipe toward the right to go back (center), easily Ping even several people.

As always Basecamp 3 for iOS is free, get the latest version with all these updates in the App Store. Thank you so much for using Basecamp, for your kind words, and great suggestions! Stay tuned, we’ve got a lot more in the works—let us know in the comments what we can do to make Basecamp even better for you!

♥️ Team iOS,
Dylan Ginsburg, Zach Waugh, and Jason Zimdars

Basecamp 3 works where you do on iOS, Android, Mac, Windows, and anywhere you’ve got a web browser and an internet connection. Your first Basecamp is completely free so try it today, it takes just a minute to sign-up.

Basecamp 3 for Mac and Windows is here!

One of the best things about Basecamp is you can use it almost anywhere. All you need is a web browser and an internet connection. Laptop, phone, tablet, hotel lounge, school computer lab, Mom and Dad’s den — you know, the one with the CRT monitor… Anyway… Basecamp also is available in fully featured apps for iOS and Android that offer the additional power and convenience of native features on your phone or tablet.

Today, in that same spirit, we’re proud to announce Basecamp 3 for Windows and Mac.

Basecamp 3 for Mac (left) and Windows.

If you’re using Basecamp 3 daily on your computer we think you’ll find the app a big level-up from the browser experience. Here’s why:

It’s right at home

Once installed, Basecamp 3 has its own icon on your desktop, in the dock on your Mac, Windows taskbar, and when switching applications. Instead of being hidden in tab within your web browser, Basecamp is now front-and-center.

Basecamp 3 in the OS X dock (top) and Windows taskbar.


Turn on notifications and you’ll see them right there on your computer as they happen. Even when you’re working in another application, a quick glance at the system tray icon or OS X menu bar will let you know when there is something new in Basecamp. Focus on work without missing a thing!

Basecamp Notifications on OS X (top) and Windows.

Available now

Basecamp 3 for Windows and Mac are free and available now. You can download them using the links below. For installation instructions view our help docs.

Download Basecamp 3 for Windows or Basecamp 3 for Mac.

Basecamp 3 works where you do on iOS, Android, Mac, Windows, and anywhere you’ve got a web browser and an internet connection. Your first Basecamp is completely free so try it today, it takes just a minute to sign-up.

Why I work remotely (hint: it has nothing to do with productivity).

Illustration by Nate Otto

These are some of the things I can do because I’m fortunate to work for a company that lets me work from anywhere:

  • Hug my kids and feed them breakfast before they leave for school in the morning.
  • Greet and make a snack for them when they get home; hear all about their day.
  • Work from my favorite coffee shop.
  • Spend a week with the whole Basecamp team in our Chicago office.
  • Spend a week with my team in sunny Austin, TX (while it’s -2ºF in Chicago).
  • Run an errand for a friend.
  • Walk my dogs.
  • Work with a friend.
  • Care for a sick child without taking a sick day myself.

After you’ve read all the books and articles about keeping on-task when working from home, setting up the perfect home office, avoiding loneliness, staying connected, sidestepping distractions, and avoiding interruptions I’d suggest one thing: embrace interruptions.

Keep reading “Why I work remotely (hint: it has nothing to do with productivity).”

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

I’d rather text than talk

Illustration by Nate Otto

Are we truly introverts or just socially and emotionally undeveloped? Here’s how I came to learn that truth about myself, how it’s changed the way I think about making software, and why if you make software Sherry Turkle’s “Reclaiming Conversation: The Power of Talk in a Digital Age” is a must-read. If you’ve ever thought, “I’d rather text than talk”, this is for you.

I’ve long considered myself an introvert. If you’re a designer or programmer, a self-proclaimed geek, a computer enthusiast — if you live on the web — you may think so, too. Perhaps this sounds familiar: I was content to play alone as a kid spending hours building with Lego, lost in my imagination. I made art, read books, and was fascinated by computers.

The computer would do amazing things if I could master its secret language of esoteric syntax. It was absorbing and stimulated the mind. Predictable and consistent, never doing any more or less than instructed.

Unlike people. They were messy and inefficient and cared about the most trivial things! I wasn’t without friends but my tribe mostly cared about the same things I did. When we did get together it was often to share techniques and experiences from our time in solitary activities. Instead of being intertwined by friendship we journeyed through life in parallel. The things we were passionate about made no sense to adults. They didn’t advance our social standing or impress the girls. So we retreated further.

It wasn’t until the internet arrived that it all suddenly made sense. I remember distinctly in college and in my first job after college the elation to learn that I could be paid to indulge in all the things I was already doing. I was able to work with computers all day long, figuring things out, reading, making, building, tinkering. The internet was wide open and seemingly crafted especially for us geeks. You didn’t even have to take a class — everything you needed to know to make things on the internet was on the internet.

Building the case for introversion

Not only did the web allow me to get paid for work I’d have done for fun but it helped me to connect with other people just like me. We worked and communicated through the web. Email and IM meant no one had to comb their hair, put on pants, make small talk, or stand in the corner while the extroverts had all the fun. Asynchronous communication was efficient and transactional. I didn’t have to ask you about your haircut or pets before requesting the information I needed from you. My “friends” were right there, neatly contained in that narrow little window on my screen. There when I need them, minimized when I didn’t.

As we geeks became more essential to the companies we worked for we were coddled. They bent the old rules to make us feel comfortable because we were shy and temperamental. Casual dress codes, unlimited Cokes and foosball tables were standard issue. We were special snowflakes who passed around articles to explain why were were so different and how we should be treated*.

It all came to a head for me a few years ago when I read Susan Cain’s Quiet: The Power of Introverts in a World That Can’t Stop Talking. Here was the definitive apologetic I’d been waiting for. I didn’t need to feel bad for being awkward, for preferring emails to phone calls, for wanting to stay in rather than go out — it was just how I was. Here introversion was presented as an advantage, not something to be ashamed of. Damn the extrovert agenda!

Whoever you are, bear in mind that appearance is not reality. Some people act like extroverts, but the effort costs them energy, authenticity, and even physical health. Others seem aloof or self-contained, but their inner landscapes are rich and full of drama. So the next time you see a person with a composed face and a soft voice, remember that inside her mind she might be solving an equation, composing a sonnet, designing a hat. She might, that is, be deploying the powers of quiet.

Years ago when I first joined 37signals I was overjoyed at having found an introvert’s dream job. Here I could work from my home hiding behind a computer nearly 100% of the time. Not working in an office meant nobody to drop by for small talk or force me to speak in front of a crowd. Customer support? Email. Meetings? Toxic. We only got together in-person a few times a year.

I remember those in-person meetings reinforced my self-diagnosis. Sitting around the conference table, the ideas and options came fast and furious. I could hardly get in a word. My coworkers wanted to work out the design now, iterating on a whiteboard in REAL TIME! What I wanted to do was take in all the information, go home and work it out in solitude, at the computer. I knew I could think as creatively as anyone else but I needed to do it on my terms.

Why take the risk of sharing a possibly stupid idea off-the-cuff when I could retreat to my cave and craft a perfectly edited proposal or iterate on a polished design in solitude?

Cain’s book validated all of this. I didn’t need to feel bad, this is just how I was and I needed to assert myself such that I could work on my terms. The book even stresses, “Don’t think of introversion as something that needs to be cured”. So I didn’t look to change, I just kept justifying. Is there anything we’re better at than justifying our faults and failures? And the internet makes it all too easy to follow only the people who agree with us and read only what represents our worldview. I may be a weirdo, but there are thousands of people who are just as weird.

Now my point is not to deride Cain’s book (which is very good) or somehow deny introversion. There is no question that introversion is real and many, many people are wired this way. If you think you might be, “Quiet” is a great read. The problem for me is as great as the book made me feel about my behavior, I don’t think I was actually an introvert.

Introverts are easily overwhelmed by too much stimulation from social gatherings and engagement, introversion having even been defined by some in terms of a preference for a quiet, more minimally stimulating external environment.

Extraverts are energized and thrive off of being around other people. They take pleasure in activities that involve large social gatherings, such as parties, community activities, public demonstrations, and business or political groups. They also tend to work well in groups. An extraverted person is likely to enjoy time spent with people and find less reward in time spent alone. They tend to be energized when around other people, and they are more prone to boredom when they are by themselves.

Extraversion and introversion

I didn’t dislike social gatherings and didn’t need to balance social time with solitude in order to recharge as is commonly said of introverts. Some of the best times of my life were in social settings. I couldn’t think of any time with my computer that would crack the top ten. I wasn’t sure what to do. Introversion justified my behavior but the more clinical definitions left me with questions.


It was only recently, years later, in divorce and another book that I found an answer. Divorce viciously unmasked my self-deception. Covering my social and emotional deficiencies in the echo-chamber of the internet and the apologetics of introversion made me feel better but it let the problems fester. In losing everything I was forced to turn to real people for healing. First in the few relationships I had left, later in seeking and forming new ones. I could have stayed home continuing to wrap myself in the comfort of the misunderstood introvert. Instead I sought change. Forming new relationships and asking for help required a humility and vulnerability I’d never thought possible but offered rewards beyond imagination.

Being comfortable with our vulnerabilities is central to our happiness, our creativity, and even our productivity.

Sherry Turkle’s Reclaiming Conversation: The Power of Talk in a Digital Age was the final piece of the puzzle. It’s a rather damning look at how the way we communicate in the smart phone era is killing real, face-to-face conversations in our friendships, families, schools and workplaces and what we’re losing when that happens.

We’ve gotten used to being connected all the time, but we have found ways around conversation — at least from conversation that is open-ended and spontaneous, in which we play with ideas and allow ourselves to be fully present and vulnerable. But it is in this type of conversation — where we learn to make eye contact, to become aware of another person’s posture and tone, to comfort one another and respectfully challenge one another — that empathy and intimacy flourish. In these conversations, we learn who we are.

Reclaiming Conversation: The Power of Talk in a Digital Age

The book is particularly focused on a population who have never developed the skills to truly have a conversation in “real time” and how that’s destroying empathy (sound familiar?). How social media offers the unrealistic promise of connecting without giving anything of ourselves. How the ways we’ve become wired to avoid boredom at all costs — stimulation is just a tap away — has assaulted our ability to be secure in solitude, rest our minds, and open them to the serendipity and creativity that comes from unstructured reflection. How even the presence of a phone on the table changes the depth and nature of a conversation.

In seeking productivity and efficiency we’re turning conversations into, as Turkle’s puts it, merely “transactional” exchanges of information. We’re treating people like apps that we tap when we need stimulation, close when we’re bored, switch away from when something more interesting comes around and delete when they no longer offer anything in the transaction.

What does this have to do with software?

At Basecamp we make software that helps people communicate, get work done and stay connected. Millions of people use it to increase their productivity enabling them to work when, where and how they want. It works on Macs, PCs, iOS and Android, phones and tablets. It notifies you when a task is due, a meeting is starting or someone needs your attention — anywhere in the world, any time of day. I’m proud to help make a tool that helps so many people get things done but I often worry about the other side. Should I be proud when a mom is using Basecamp instead of watching her kid’s soccer game? Who’s fault is it when dad comes home from work on-time but isn’t really present because Basecamp keeping pinging his phone all evening? Every time Basecamp sends a notification should I wonder if it’s helping someone be a better worker or impeding them from being a better person?

The age of the smartphone is here to stay. Well beyond the days of Web 2.0 our industry is making the best software ever seen. Everywhere you look there are beautiful, fast, intelligent apps that allow us all to do more both simultaneously and cumulatively. We’ve had tremendous success in making people more productive but what have we gained? Do we have more free time? More leisure? No! As Turkle aptly puts it, “We are living moments of more and lives of less.”

Reclaiming Conversation ends with a call to make software that has moved beyond mere productivity and thinks about the human on the other side. Can we make apps that are less-sticky, less addictive, that reward users for completing a focused task then quitting rather than enticing them with something else? Can apps encourage uni-tasking? Can they help users take back their time?

I’m proud to work for a company that’s starting to ask these hard questions and seeking real answers. Basecamp’s Work Can Wait feature let’s users create a clear separation between when they’re working and when they don’t want to be bothered with work—even on mobile devices. This is a great step forward. Granted, many apps and operating systems have recently incorporated similar features the help us manage the noise but the future is here when computers are proactively helping us be more human, not less.

Reclaiming Conversation has completely changed the way I think about people, computers, social media, and designing software. If you’re a parent, a co-worker, or a friend; if you’re dating or married; if you’re a boss; if you make apps; if you’ve ever thought, “I’d rather text than talk”, this book is a must-read. It’ll make you think about the way you use software, the ways software can use you, and what you’re losing every time you glance at your phone. Our industry may truly be full of introverts, but I suspect that at least some of you are like me, not realizing how you’ve let these tools change you. I hope I’ve made you curious enough to find out. If you make software, I hope you’re inspired to help your users find balance, too.

Visit Basecamp.com to learn more about the all new Basecamp 3, try it for free and start living like Work Can Wait.