“How do I get out of my writing rut?”

Weird truck

Often I get asked a variation of:

I’ve been writing for a couple years, but I have no more inspiration, and little readership. How do you write? Where do you get inspiration? How do you get out of the rut and get people to start reading?

We all get this way. But here’s a few things that have helped me keep pushing through that, and eventually ended up with some stuff that’s done well on places like my blog Ninjas and Robots, or Signal v. Noise, and have even found their way into The Huffington Post and Fast Company.

1) Create a schedule, and go with what you got.

Years ago I felt I was doing a somewhat decent job writing, but I just wasn’t getting any traction. Dustin Curtis had just launched a new blogging platform called Svbtle that was getting a lot of attention and was only publishing authors he had invited. I didn’t have an invite. But I knew his attention could rub off on me. So I took a shot, emailed him and showed him some samples of my work.

As I hit send, I felt very pessimistic about my chances. The other folks writing on Svbtle were much better and had better followings than me.

No way I’m getting an invite.

I got an invite.

Huh, I should stop assuming things won’t work.

But writing on his blog network came with a caveat, publish one thing a week. I didn’t know what would happen if I didn’t, but I assumed he’d kick me out, and I really didn’t want that. I needed this opportunity. So I kept publishing once a week. If I was up against the end of the week and hadn’t had inspiration, I would just find something to even take a picture of. Like that truck I saw as I walked down the street.

Or I saw an interesting article in Esquire about Bill Murray. Again, under the gun to get something published that week, I wrote up a few sentences on why I thought it was interesting.

Not my most brilliant post — turns out to be one of my most trafficked posts.

Don’t worry so much about meeting the schedule with the same quality and quantity. Running up against your schedule deadline, find a picture of something interesting and write a hundred words about why it’s interesting. That’s it. Write a yelp review even. Get some personality in that review and put it on your blog. Just do something, anything, to keep the momentum going. Sometimes you’ll surprise yourself.

The momentum will actually push something through that your weird brain pessimistically thought was terrible and turns out awesome. As journalists like to say, “Go with what you got.”

2) Stop writing the same thing.

If you write about yourself, start writing about other people. Or vice versa. I personally like to share a lot of anecdotes about my life, but I find I get into a rut. I don’t want to talk about me all the time. Especially if I’m going through some really tough struggles. But there are so many interesting people to write about. Here’s: a great example on my blog. I took myself completely out of it. Just wrote about someone in the news (James Garner) who had recently passed away and how cool his life was. A lot easier to write about him, when I feel stuck writing about myself.

3) Take a class!

I don’t know why we as writers stop taking classes. They are great places to learn new things and get yourself on a schedule. There’s probably a ton of places to find a fun writing class. I took one at Gotham.

It was in that class actually that I wrote that article above about James Garner that went gangbusters. It was another thing pushing me to write something different. If you’re stuck on your blog, I’m sure a homework assignment can shake some new stuff loose.

4) Bands don’t keep playing the same song in the same place. Write somewhere else.

Find a new place to share your stuff. Stop the blog for a bit. Get your stuff in a magazine, the Huffington Post, wherever. Go pitch some editors for some guest posts and articles.

5) Bands also don’t keep playing completely original songs at each venue either.

They repeat their hits or their latest album. They might improvise and riff on old songs, but they reuse a lot. That’s beauty of #4’s advice about finding new outlets to write — you can recycle some of the ideas you are most proud of. James Altucher is great at this. It’s like the guy is a writer Everywhere. And you see some of the same stories. But that’s fine. Very few people are like me and reading his stuff on all these different places. He’s out there making new audience members constantly from these new channels.

6) Practice your idea muscle.

It’s been super interesting hanging out with Jason Fried these days since I took over Highrise. The guy always has an idea for something. A new book, a new blog post, a new product. Only executes on a tiny fraction of those things he thinks are worth it, but man does he have a wealth of things to pick from.

Need a little push to do the exercise? Come up with lists. Everyday, push yourself to come up with lists of things to write about. Most will suck. But don’t let your brain atrophy. Keep coming up with stuff.

7) Get out and do some new things.

Go to a new museum, or weird place. Pick up a new or strange hobby for a bit. Go buy some strange magazines you’d never ever buy. Learn what other people are reading and caring about. Lots of interesting things to draw from those experiences.

8) Copy someone else’s template.

I’ve literally taken writing I’ve liked and dumped it into my writing software and just written on top of it, working to match the flow and structure, deleting their stuff as I go.

Go find a writer that you like, and write something using their piece as a template. Maybe you try and copy their tone. Or structure. How they use analogies, or anecdotes. Or even copy the argument. Try to make their same argument with a different analogy or method. It can be freeing to use the constraint of someone else’s writing.

9) Stop writing. Talk.

Pretend you’re giving a talk instead. Or some kind of presentation. Get out of the chair and walk around with your phone recording your voice. Moving and talking have a way of loosening up whatever it is.

10) Put together chocolate and peanut butter.

Take two unrelated things, stories, or people and show everyone what makes them so interesting together. Why was writing Frankenstein like stealing cars? What does Elon Musk have in common with a boy who wants a pet moose?

Take things that people haven’t put together before and put them together to show what an interesting combination they make. Fries and milkshakes? Yes, try that.

11) Buy books like they’re free.

When you’re broke, like I’ve been many many times, you need to find some creative ways to get by and you get to complain all you want about the prices of books (Like wtf college? Why do you keep releasing new versions of the same text book when all that changes is mostly page numbers and not the physics of the universe. There goes another $80 down the drain for the “new edition”).

But I don’t get most other people’s hangup with how much books cost. If you aren’t living paycheck to paycheck, and buying a $20 book isn’t going to change the food you buy your family, give yourself a huge budget to buy books.

If there’s something I’m really interested in, I’ve turned off the nag in my head, “oh man, this should be 15% less. I’ll wait.” Or “I’ll wait for the library”. I need more ideas, quicker; instead of waiting for the rare library visit.

The other weird thing people feel about books is that they’ve “invested in it”. This leads them to feel, when they realize they hate the book they “invested in”, they can put it down for fear they’ll waste their investment. But they never finish the terrible book. So they rarely get to another.

Throw more books away. It’s a sunk cost. Forget about the past “investment”. Move on to something interesting.

I buy books like they are free. I saw a physics textbook that looked interesting. Maybe there’s something in there to help me think about problem solving. Oh it’s $99. I don’t care. I didn’t even finish it. I got something interesting out of it after a couple chapters, might make its way into an article, and the book is there if I want to learn more physics.

Again, if you live on a tight budget, you have to be a lot more careful. But if you want to introduce yourself to new thinking and options as a writer, and your budget has money for clothes, drinking, eating out, vacations, cable, televisions, etc., I’d rethink the lack of allocation you have to books, magazines, and anything that can potentially get new ideas across your brain faster.

12) Stop hitting the delete key.

I want to create something out of nothing but nothing isn’t a great place to draw from. -Mitch Hedberg

Just write. Free write. Take your writing software or notebook and just go nuts. DO NOT DELETE or edit yourself. You need a body of thoughts before you can edit. You need that place to draw from.

Don’t underestimate paper either. It’s a great place to just flow. Typing can be too slow to get all the thoughts out there.


I hope that’s helped some. If there’s something else on your mind and you feel like you could use some more help, please don’t hesitate to ask. It would be awesome to meet you on Twitter, or see where all this writing stuff led to what I’m now doing with Highrise.

Always Glad You Came

Illustration by Nate Otto

On the day after Christmas, as buckets of freezing rain and sleet fell on the Chicago area, I white-knuckled my way to the 61-year-old Uptown Tavern in the suburb of Westmont to interview the owner, Bill Carlson. I wasn’t expecting to find anyone at the bar, but when I walked in, there were 15 people drinking, chatting and watching TV.

It’s always busy at the Uptown, which hosts fundraisers, serves a free turkey dinner on Thanksgiving and provides a place for local third-shift workers to unwind in the early morning. Not bad for what Bill calls “a little shot and a beer bar.” He knows that even a humble tavern needs to keep evolving to survive. Pop open a can of Old Style and settle in for a story about a friendly neighborhood dive.


Transcript

WAILIN: Bill Carlson has two rules when it comes to bartending. Number one: Always pay attention when you’re behind the bar. Bill takes this principle so seriously that eight years ago, he stopped smoking months in advance of the state smoking ban so he wouldn’t have to step out for breaks.

BILL: I’m so anal about waiting on customers that I wasn’t going to be outside when a customer might need a beer or a drink. So, you know, I get very upset with my bartenders if they turn their back to the bar to have a conversation. You can have a conversation and still scan the bar to see if somebody needs something.

WAILIN: Bill’s second rule of bartending, which relates to the first one: Listen to your customers.

BILL: You just try to be a good listener and not offer too many solutions. That seems to work out better than just — being a good listener is, I think, very important and remembering what they’re telling you. So if they come back in a day or two, you can ask them about it. Yes, I do believe that’s very big.

WAILIN: Bill has been listening to his customers for a long time. He started bartending in 1977 and has spent most of his career as the owner of the Uptown Tavern, an unassuming watering hole in the Chicago suburb of Westmont that’s been open since 1955. Bill describes the Uptown as just a little shot and a beer tavern, but the bar has been constantly evolving beneath its wood-paneled surface, and that’s largely because of Bill’s listening skills. Not just lending a sympathetic ear at the end of a long day, but paying attention to what his customers want. For example, no one seems to order Cutty Sark or JB Scotch anymore.

BILL: Now you better have Johnnie Walker and Dewar’s and onto the next line of ’em, you know. Bush Mills Bourbon, you know, I’d never heard of it. “You gotta get Bush Mills, everyone likes Bush Mills.” Okay! We got Bush Mills, you know? So just stuff like that. So you gotta keep up with the times, ask your clients or your customers what they like, what’s the new trend, you keep up, you’ve gotta keep up, you know, think young. You want a younger crowd to come in and spend their money as far as the bar business, think young and ask questions, ask your people, ask the customers at night what they want, you know, what they’re looking for.

WAILIN: Pull up a stool at the Uptown Tavern on this episode of The Distance, a show about long-running businesses. I’m Wailin Wong. The Distance is a production of Basecamp. Introducing the new Basecamp Three. Basecamp is everything any team needs to stay on the same page about whatever they’re working on. Tasks, spur of the moment conversations with coworkers, status updates, reports, documents and files all share one home. And now your first basecamp is completely free forever. Sign up at basecamp.com/thedistance.

BILL: It’s a blue collar town, it’s a working man’s town.

WAILIN: The Uptown Tavern is located in downtown Westmont, Illinois, a town that earned the nickname “Whiskey Hill” during Prohibition because the alcohol kept flowing. The bar is across the street from a commuter train station and kitty corner from where the legendary blues musician Muddy Waters used to live. For decades, the Uptown opened at 6 am and drew an early morning crowd of workers coming from overnight shifts at the nearby hospital and manufacturing plants. In 2009, the village of Westmont banned alcohol sales before 9 am, and those regulars disappeared.

BILL: They stopped coming in because they, you know, if they get off of work at 7 and we couldn’t open ‘til 9, they’d go get something to eat or something. They’d go home and start doing a project or doing whatever, found other places that were open earlier, so kind of lost all that trade.

WAILIN: Bill fought to get the time moved earlier, and the town relented. Starting January first of this year, the Uptown got to open at 7 am, and Bill is hopeful that his morning regulars will return in a few months as word gets around. Here’s how a typical day at the Uptown unfolds.

BILL: It’ll be an early morning crowd. It’ll thin out around, you know, after The Price is Right because it’s very — Price is Right is big around here, from 10 to 11, you know, and then it’s the Jeopardy crowd from 3:30 to 4, and you’ve got your after-work crowd. About 6, they start clearing out, and then about 7, 8 o clock, when we have our live entertainment for the evening starts up, it picks up again.

WAILIN: The Uptown is a modest place, located in a building that used to be a taxicab stand. There’s a large U-shaped bar, four tall tables with stools along the side wall, six TVs, five video gaming machines, a machine that sells Lotto tickets, and a digital jukebox that no one is allowed to play during Jeopardy. Aside from a collection of model race cars and some beer posters on the walls, there’s not a lot of decor. It would be easy to look at the Uptown and think this is the way it’s always been. But the place is very different from how it was in 1988, when Bill started working there after 13 years at another bar around the corner.

BILL: Oh boy, it’s totally changed. It had a drop ceiling. It had one TV that was in that corner that was about a 20-inch TV. It had an antenna, like on the roof, to pick up Bear games ’cause back then, they were getting blacked out because they couldn’t sell out all the time, so you’d pick the signal up from Rockford. It was a bunch of older people in here that were very bigoted, lack of a better word, I mean, and they were, and it was horrible. There were a lot of fights and we cleaned the place out.

WAILIN: A few months after Bill started working at the Uptown, the owner of the bar, an older man who had been in the hospital and wanted to retire, offered to sell him his share of the business. Bill had a young family to support and jumped at the chance. A few months after that, the previous owner’s business partner wanted to sell his share, so Bill brought in a friend to buy that stake. That was in 1989. And there was no real passing of the torch. Bill and the old owner closed their deal at 2 in the afternoon, and Bill was behind the bar that evening when his predecessor came in.

BILL: He walked in at five o’clock, took all the money out of the cash register, and walked out. And that was the only advice he gave me was: Don’t leave that cash register open. ‘Cause I was so appalled, I called my lawyer, and he goes, “Don’t worry about it. In a year from now, you’re not even going to think twice about it.” Twenty-six years later, I still think about it! How could he do that? He had a snoot full and he said, “Hey, you know, we closed today so I guess I get today’s receipts too.” So he just came and took all the money out of the cash register. I was standing behind the bar with my mouth ajar. I was like, what did you just…? And he walked out the door. That was the last time I actually saw him.

WAILIN: And with that, Bill was left to run the Uptown. At the time, the bar had just two beers on tap: Miller Lite and Old Style. The place was the kind of friendly neighborhood dive where you could get your paycheck cashed on Fridays instead of going to a currency exchange, and where you could spend two dollars to enter a non-legal, low stakes betting pool. None of that exists anymore, but Bill’s strategy for running his business is the same as it was back then: Give customers a reason to visit. And the Uptown is popular. On the day after Christmas, in the middle of a downpour of freezing rain and sleet at three thirty in the afternoon, there were 15 people at the bar. Bill knew pretty much all of them. And he was expecting even more people in the evening.

BILL: We’re a little shot and a beer bar, but we’ve expanded as far as the liquor we carry, the beer we carry. We’re trying to keep up with the Joneses kind of a thing, but in order to attract people, you give people a reason to come in, my philosophy, and you make it priced accordingly, you know, to draw ’em in and you have different things to bring ’em in. The poker machines, karaoke, live music, whatever it takes.

WAILIN: You can still get Miller Lite and Old Style at the Uptown, but the bar also stocks a rotating selection of 15 craft beers and a wide variety of liquor. Bill has tried a lot of other things to get people in the door over the years. He’s hosted a yearly pig roast, a blues night, and Super Bowl parties where you could fill up a 25-ounce mug of beer for a dollar. His bar was the first one in town to have a CD jukebox. For the last eight years or so, the Uptown has featured live entertainment. Tuesday is open mic night, where you can play an instrument or read poetry. Thursday is karaoke. And bands play on Friday and Saturday nights. Bill stopped working nights when he turned 50, but sometimes you can still find him behind the bar on busy evenings, washing glasses and getting ice.

BILL: At night, it’s definitely gotten younger, especially when I quit working nights, you know, we went younger with a younger girl bartender, which brought in a younger crowd and it just makes sense, I mean, without a doubt. And as I’ve gotten older, you know, I could see like the crowd getting younger and younger and when I come in here at night, from knowing 95 percent of the people, that’s down to, like if I come in here at 10 o clock at night, five percent of the people know who I am. Who’s the old guy over there, you know? Or I’ll go behind the bar and do something, you know, who’s that? They don’t know me. Which is nice, it really is.

WAILN: The daytime crowd tends to be older and more price conscious, and Bill is sensitive to that. He’s kept his prices down, charging just two seventy five for a pint of Miller High Life or Miller Lite, and he offers different specials each day. The Uptown crowd might be price conscious, but it’s also very generous. Bill holds a lot of fundraisers. It started years ago, when he raised money to cover the funeral expenses of a friend who had died without the means to be buried, and the philanthropy grew from there. The Uptown raised over ten thousand dollars for Make A Wish in 2015. For the last four years, Bill’s hosted a summer cookout to raise money for disabled American veterans.

BILL: So I like the fundraising. I enjoy it, you know, I think it’s for a good cause and people get behind it, even people who don’t have a lot, you know, we try to do raffles and stuff like that for people that don’t have a lot of money but they want to give, so it’s not the upscale raise a hundred thousand dollar kind of a deal, but it’s more local, you know, and people get behind it.

WAILIN: Bill estimates he’s raised ten thousand dollars for disabled American veterans over the years. There’s a bucket over by the video gaming machines for unredeemed vouchers. When someone is left with just a few cents and they don’t feel like cashing out such a small amount, they can toss their voucher in the bucket.

BILL: They don’t care about two cents or five cents, and I spend the time to redeem them all and turn it into cash. Hey, if it’s a couple hundred here, a couple hundred dollars there, it means something to a disabled American vet. If it’s a car ride to a doctor, whatever.

WAILIN: Bill likes to take care of people, whether it’s the beneficiaries of his fundraisers or his customers. The Uptown is open 365 days a year. It’s hosted weddings, including the ceremony and reception of a couple that met at the bar. On Thanksgiving, the Uptown serves a free turkey dinner with all the trimmings. And on any day, if you come in while Bill’s behind the bar, you’ll get friendly service and a sympathetic ear from a guy who looks a lot like the actor Sam Elliott.

BILL: I love people. I love tending bar. I feel like I’m on stage when I’m behind the bar. I’m a very shy person when I’m not behind the bar, and the bar seems to bring out the best in me.

WAILIN: At 61, with almost 40 years of bartending experience behind him, Bill has perfected the art of listening and making his customers feel at home. His son, Bill Junior, who goes by Billy, worked briefly as a bartender and remembered how his dad taught him to always be scanning the bar and not talking too long.

BILLY: I went away to college and I got a bartending job and that was my hardest part, was I didn’t want to say like, “Okay, I have to go now, nice story!”

BILL: People talk and you just gotta walk away and go serve and walk back, and they’ll just continue where they left off. They don’t mind. They want to tell you what they want to tell you. They don’t care.

WAILIN: Bill doesn’t drink and he hasn’t for years — Billy has never seen his father drink. Bill has taken to walking six to seven miles a day. He thinks he’ll work for another five years and then look for someone to buy the Uptown. His business partner — the friend who bought a minority stake in the bar 27 years ago — is still involved with the business, taking care of the bookkeeping and ordering, and at some point he’ll want to retire too. Bill thinks they’ll get out together, although he’s not ready to say goodbye entirely.

BILL: Part of the sale would be contingent on me still getting to work here because I really like what I do, and I really think I’m good at it, and my partner tells me, he goes, you’ll know when it’s time to stop. You’ll know. People will tell ya. Why are you such a crab ass? Or for whatever reason, you know. So, I mean, as long as I get good reports, I’m still busy. People come in and they ask me when are you gonna work or when are you working? You know, you know.

WAILIN: The Distance is produced by Shaun Hildner and me, Wailin Wong. Our illustrations are done by Nate Otto. Special thanks to Billy Carlson for introducing me to his father. I’ve started posting transcripts of each episode. If you want to check those out, visit thedistance.com, where you can also sign up for our newsletter. The Distance is a production of Basecamp, the leading app for keeping teams on the same page about whatever they’re working on. Your first Basecamp is completely free forever. Try the brand new Basecamp Three for yourself at basecamp.com/thedistance.

Announcing the first “The Basecamp Way To Work” workshop

Learn how we do this!

For years people have asked us how we work at Basecamp. We’ve shared our business and development philosophies in Getting Real, REWORK, and REMOTE, but we’ve never lifted the veil on our unusual work methods.

What does our day-to-day look like? How do we organize and manage work? How do we communicate across the company? How do teams coordinate? How do we gather ideas, consider feedback, break work into digestible chunks, build, and deliver?

This year we’re going to launch a new live-in-person workshop series called “How We Work”. But before that, we’re going to hold a pilot workshop — a test run — on Thursday, January 28th. The pilot workshop will run for 3 hours. This will be a back and forth — showing, questions, sharing, questions. We’ll set the tone, but the audience will determine the direction.

We’ll share everything behind the scenes. We’ll show you how we use Basecamp to run Basecamp. Everything will be exposed. After this workshop you’ll have a new perspective on how people can work together, how and when to communicate this way vs that way, and how keeping everything together in one place is the secret to a few small teams making some really big things.

None of this has been shared in an interactive setting like this before. The workshop will be held in the theater in our headquarters in Chicago, IL. Only 25 seats will be available, so don’t miss out: Buy your ticket here.

We look forward to seeing you on the 28th.


UPDATE: The event has sold out. The plan is to do these often, and eventually make this material available online for anyone to watch. Stay tuned to our Twitter feed at twitter.com/basecamp for announcements of future events.

Try harder to be someone else

Bullshit

“Just be yourself!” is commonly served as encouragement for people facing challenges in life. Whether that be in personal relationships or job hunts or speaking at a conference. If you’re already the perfect person, that’s sound advice. If not, it’s worth closer examination.

Whoever you happen to be right now, at this very moment, is highly unlikely to be the person you ultimately want to be. Maybe you occasionally have a short temper. Maybe you don’t know as much about programming or speaking at conferences as you’d like to. Maybe you procrastinate too much.

Whatever it is, you could probably stand to be more like other people in a bunch of areas. Being content merely being “you”, and whatever incremental iteration on that concept you can scrape together, is a sigh of resignation.

This is where the power of envy comes in. As emotions go, envy doesn’t exactly have much popular support. I mean, when you make it onto the list of the seven deadly sins, it’s probably best something to steer clear of, right? I say wrong.

Envy is a useful jolt of motivation to be more like someone else. Better, smarter, wiser, hell, even prettier and richer (oh, the horror 💀!). All attributes that can be refined through your own actions. You can learn new skills, you can read more, you can work out, you can save money.

I’m not the same person I was 20 years ago. Thankfully! I decided early that there was nothing so special about this happenstance of personality traits, skills, and knowledge I had acquired by age 16. Not only that, I reveled in the fact that there were lots of people that were downright better than me at all sorts of things. Things I wanted to be better at. They provided a clear template to first emulate, then adopt from. In other words, I was envious.

I remember attending JAOO 2003, a programming conference in Denmark, and seeing Kent Beck talk about Extreme Programming. Not only was the subject matter interesting, but even more so the manner Kent delivered it. I felt deeply envious at his excellent delivery and vowed to be more like Kent. To study and emulate him until I had become more Kent than me (at that time) at delivering a convincing argument on stage.

Same thing happened when I discovered the writings of Gerald M. Weinberg. I devoured Secrets of Consulting, Are Your Lights On?, The Psychology of Computer Programming, An Introduction to General Systems Thinking, and his Quality Software Management series. I got deeply envious of not only Gerald’s stellar writing skills, but his profound insights. I set about to notice and ponder the world of programming and teams like he had. To be more like Gerald than I was myself at the time.

I could go on and on about this. I’ve had similar pangs of envy watching the onboard videos of Patrick Long driving my race car in 2010. Of reading Kathy Sierra’s insights on making users kick ass. Of the tranquil state of mind and techniques employed by Marcus Aurelius and Seneca. I’ve wanted to change myself so many times to be like so many other people, and I think I’m far better off for it.

So don’t be so quick to fall in love with who you are right now. Allow yourself to imagine being more like someone else than yourself. Then make it happen through envy and emulation.

Blow your deadline, blow your budget, and chalk it up as a success!


At the end of 2015, we launched an account switching feature in the Basecamp 3 Android app. On the surface it’s a pretty basic feature — if you’re part of more than one account, you can just tap a menu and flip over to another account.

This feature met all the criteria our team looks for when picking new work to start: it was something customers wanted, it was something we wanted, and it seemed shippable within a two week budget.

The result: We shipped a great version of the account switcher. Success!

The fine print: It took us six weeks to ship. We completely blew the budget and deadline. 😭

Six weeks to ship this? Sheesh.

What happened? How did we balloon from two weeks to six weeks? And how can we call this a success?!



The Problem: We Didn’t Have All The Information

As many programmers have (rather painfully) experienced, we didn’t have all the information up front. When we originally budgeted two weeks worth of time, we assumed that our foundational code was solid enough to keep building on.

That assumption was wrong.

Over time and in the natural rush leading into launch, some things slipped. Our code wasn’t quite as organized as it used to be. AsyncTasks were making our code hard to read, and even harder to maintain. Our local data storage scheme was hard to use. Somehow four different authentication paths got bolted on. Our unit test coverage wasn’t as robust as it should have been.

But none of that was obvious during week one of building this feature. Or even week two. Or even week three. You get the picture.

The Real Measure Of Success: Laying The Groundwork

Sam Stephenson, a programmer at Basecamp and one of the smartest people I’ve ever met, said it best:

Then, instead of solving the problem with an ad-hoc, one-off change, lay the groundwork for a general system that facilitates the specific change you want to make.

That, in a nutshell, explains how our two week feature turned into a six week mini-project. And it’s why we absolutely classify this venture as a success.

We ripped out AsyncTasks and replaced them with Android Priority Job Queue. We rewrote our entire data storage system. We cleaned up our authentication code. We wrote new tests and improved others. We did a bunch of things that would take too long to list here. We did everything we could to improve our general systems for future work. (And oh yeah, we wrote all the new code to make switching accounts work too!)

In short, our team recognized the incredible value in doing things the right way, not the fast way. We knew that rewriting, refactoring, and reorganizing large chunks of our codebase was a worthwhile effort to give us a more solid foundation going into 2016.

Yeah, we could have shipped this feature in two weeks. But it was far more important to lay a solid groundwork in six weeks. We respect our deadlines, but we respect the quality of our work much more.


What Did We Learn?

Even though we were happy with the end result, there were certainly things we could have done better. So what did we learn?

  • 📅 After one or two weeks, we could have paused for a couple of days and taken a step back. This would have given us time to analyze more deeply, reset expectations, and set a new soft deadline. Even if we came to the same conclusion / deadline, resetting still would have been beneficial for getting us all on the same page and reassessing our current priorities.
  • 🎥 As soon we had a feeling this was going to take more than two weeks, it would have been helpful to schedule regular Google Hangouts for our team. Discussing things “face-to-face” (in moderation) can really bring out a lot of good ideas and attack vectors to problems.
  • 📝 We could have done more frequent, small written pitches to help describe interactions and systems. When discussing something complex, sometimes rapid-fire conversations in Campfire can be hard to follow. Luckily, Basecamp gives us a lot of options like to-dos, documents, or messages to take things down to a slow gear — letting us write more methodically and thoughtfully to clarify our thinking.
  • 🏃 Rushing gets you nowhere. There were a few moments where I felt the need to push harder, to rush, to race to the finish line. I think that’s only natural when you’re motivated and want to do great work. But my teammates were supportive and we were able to refocus on the long-term. Great teammates will always help you make the right decision.

So in the end, we shipped a pretty nice feature, laid the groundwork for 2016, and learned a lot along the way.

I guess doing all that in six weeks doesn’t seem so bad. 🎉


We’re hard at work making the Basecamp 3 and its companion Android app the best it can be. Check ’em out and let me know what you think!

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.

How can I find someone to help me?

Wanderer above the Sea of Fog by Caspar David Friedrich

I’ve been running businesses for over 10 years. I helped start Inkling at the end of 2005 with Y Combinator.

One of my biggest frustrations was simply how little the company spread through blogs and news sites. I echoed the wants of every other entrepreneur. How can I get more press? How can I meet more bloggers who want to write about us? Do I need to hire a PR person?

We had a blips of press when we first started. But for 9 years it was in business (was acquired last year), it’s a minuscule list.

Inkling had been able to stand despite the difficulty spreading the word the way I wanted, but I hated that feeling of being beholden to other people to spread what I was working on.

As I found myself dreaming of what I’d work on next, I was haunted with the struggle of finding people to spread my work.


In the late 1980s there was a teenage actor who was doing well finding movie roles. But as quick as his career started, it stuttered.

So he fell back to Plan B, and went to college. But he couldn’t let the acting bug go away. He kept looking for and landing parts. Then in his final year of college, he landed the best role of his life — a starring role in a movie filled with A-list actors and a great director. This was an Oscar-worthy movie.

So he quit school and moved to LA to pursue a professional acting career full-time.

Except, the movie bombed.

Critically, it did well. But it was a box office dud. And his hope that this was his stepping stone to stardom was squashed.

He was back to being a largely unknown actor, sleeping on friends floors in LA, with endless competition. He’d get an occasional minor role, but was making less than when he was a teenager.

He needed a breakout role. But no one was giving it to him.

So, he decided to do it himself.

He dusted off a script he had started in college, and with a friend put serious time into turning the half-written document into an actual screenplay. When they thought they finally had something, they started shopping it around. And, it wasn’t half bad. They got some interest from a big name studio, and made a deal.

Just one problem. The studio decided they didn’t want either of these guys to act in it. They wanted A-list celebs to star in the movie.

The whole point of writing the screenplay was to give them big parts to help launch their careers, and now the plan was falling apart.

But another friend of theirs with some clout at a movie studio, was able to step in and find a new buyer for the script. The new buyer green-lit the movie, and put the friends back in charge. They gave themselves the parts they wanted, and the rest of the story is very well known.

In 1997, on Christmas day, the movie premiered. It made over $225 million in theaters, was nominated for nine Academy Awards, including Best Picture, and won two of those awards, Best Supporting Actor, and most importantly…

The script Matt Damon had started while attending Harvard became Good Will Hunting and won Best Original Screenplay for Matt and his good friend, Ben Affleck.

Matt and Ben’s careers soared, catapulted by the success of that movie and their roles in it. All because they worked hard to become what it is they tried so hard to find — someone to put them in starring roles in a great movie.


Become that which you seek

Everyday I bump into someone struggling to find someone else to help them with their project or career. They are business people looking for technical co-founders or people like me at Inkling looking for someone else to write about me.

Now, from all these years in business, I realize that Matt Damon had it right. Instead of looking for some executive producer to give him a starring role, he was just going to become the executive producer.

If you’re a “business guy” stuck because he can’t find a technical co-founder: go become the technical co-founder. Go to some classes, conferences, meetups. Read and use the same blogs and forums. Do what you think a technical co-founder would do. You’ll be surprised that the action of trying to accomplish this actually puts you in the company of a great deal of people who would make… really great technical co-founders.

You know who Matt Damon met on the set of his movie? Steven Spielberg. Who then cast him for a role in Saving Private Ryan.

I was so sick of no one writing about me and the companies I work on, I decided I needed to become that writer. I put in years of practice and patience of publishing blog post after blog post and having three people read them (my wife, my mom and me). But, eventually, my blogging gained some traction and followers.

One of those followers turned out to be Chris Dannen, a senior editor at Fast Company, who asked me to write for them. About what? About me. And now, that’s turned into invites to write about my projects for other magazines and newspapers.

I had spent all this time looking for someone else to write about me. But, when I spent that time instead becoming the writer, better opportunities presented themselves.

Of course, this took a while. Everything worth it does.

But a funny thing happens when you do the work to become the thing you seek so much from others. You find it.


P.S. It would be awesome to meet you on Twitter, or see where this has all led to what I’m now doing with Highrise.

Basecamp is hiring interns for summer 2016

Basecamp is looking for talented interns to join our team this summer. We’re excited to work with you, and the things you work on will impact millions of users at the world’s leading online project management tool.

About the Basecamp summer internship program

Interns at Basecamp work on real projects and are mentored one-on-one by a member of our team who will guide you throughout your time at Basecamp. The projects you’ll work on as an intern at Basecamp are all derived from real problems we face as a business, and we expect you’ll have a meaningful impact during your time here. You’ll leave Basecamp with new technical, creative, and business skills and having accomplished something significant.

Internships at Basecamp are remote — you can work from anywhere you want, provided there’s some overlap in time zones with your assigned mentor. We’ll fly you to Chicago once or twice during the summer to get together with your mentor and the rest of the intern class, and you’ll talk regularly with your mentor via phone, Skype, or Google Hangouts. You’ll also participate in some of our dozens of Campfire chat rooms every day.

All internships are paid and require a commitment of 8–12 weeks of full time work between May and August 2016 (we’re flexible on start/end dates, planned vacations, etc.).

About you

We’re hiring interns interested in working on programming, product design, operations, marketing, and data.

Regardless of role, there are a few key things we’re looking for in interns:

  • You are independent and self-driven. Basecamp is built on the concept of being a team of managers of one, and that applies to interns as well. You’ll get plenty of support and guidance from your mentor and the rest of the team, but no one will be telling you how to spend each minute of your day, so it’ll be up to you to make sure you’re making forward progress.
  • You are an excellent communicator. We write a lot at Basecamp — we write for our products, we write for our marketing sites and initiatives, and most importantly, we write as our primary way of communicating internally. Clear and effective communication is essential to being successful at Basecamp.
  • You have fresh ideas and you’re willing to share them. We don’t know it all, and we actively want to hear fresh ideas and perspectives that we haven’t considered.
  • You’re eager to learn. You’ll dive right in to new technologies, new approaches, and new concepts and apply them to your work.

How to apply

To apply, send an email to internships@basecamp.com explaining why you want to be an intern at Basecamp, what projects you’re interested in working on (see below), what work you’ve done in the past, and why we should hire you. Feel free to include your resume, but we’re big fans of great cover letters over resumes. Be sure to tell us what dates you’re available this summer and where you’ll be located.

We’ll be accepting applications through Wednesday, February 24th. We’ll be in touch to confirm receipt of your application and let you know about next steps shortly after we receive your email.

The projects

As an intern at Basecamp, you’ll work on one of the following projects directly with a mentor.

  • Programming: Research and implement new features for Trix, our open-source rich text editor (JavaScript / CoffeeScript) and integrate those features in Basecamp 3.
  • Programming: Make our Android app more Androidy. Taking into consideration the foundation of our hybrid (web + native) app development philosophy, our Android team will help you explore ways to make uniquely powerful Android features — ones that make our customers reach for their Android device instead of the desktop app.
  • Programming: Change the way people find information internally at Basecamp by unifying various internal search tools into a single source of all the information people need to respond to customer problems. You’ll talk to internal clients, survey the state of the world, and then build out a solution.
  • Design: Understand how people work with clients in Basecamp through a mix of quantitative analysis and customer research (surveys, structured interviews). You’ll work to structure the problem, identify the data that you need, write survey questions and interview guides, conduct interviews, and synthesize findings and implications for client features within Basecamp.
  • Marketing: Help us target a specific industry (or “vertical”) by picking an industry, identifying the various stakeholders who are involved, interviewing them, and building out a sample Basecamp to demonstrate how Basecamp can help them accomplish their work. You’ll launch your work and then measure the impact of that work on the targeted vertical.
  • Marketing: Identify what people are saying about us on social media by using your analytical and digital marketing skills to help determine both quantitative and qualitative ways for us to know what people are saying about Basecamp. Are they generally happy? Satisfied? What are they talking about? How can we measure our impact?
  • Operations: Bring us into the IPv6 age by coming up with a plan for us to add IPv6 support to our public sites, testing support, deploying the new configuration, and providing documentation and training for our operations and support teams.
  • Operations: Establish a way of offering custom domains for Basecamp 3 customers. You’ll figure out how to automate provisioning, handle terminating thousands of SSL certificates, monitor for problems, and make it a great customer experience.
  • Operations: Upgrade our hardware provisioning process so we have a fully automated process to take a server from the point of arriving at our datacenter to being production ready.
  • Operations: Make it easy for new people to come on board or set up a new computer by figuring out how to run everything you need for development in a virtual machine or container.
  • Data: Help us find problems before we feel the pain of them by improving our ability to identify unusual values in the over 30,000 services we monitor to tell us about the health of our applications and businesses. You’ll identify the right algorithms to use to detect aberrations, the parameters needed to ensure that we balance false positive and false negative alert rates, and put the system into production.

Discouraged — I’m not any good

Uranium hexafluoride — I used to make this stuff

I’m currently trying to teach myself coding and feeling a bit discouraged at the moment. Trying to hear of other’s success stories to see if it’s worth it to see it through to the end. (zeexik asks on Reddit)

Who hasn’t felt like this about something? We’re out of school, but there’s things we want to still learn to get where we want to go. But it’s daunting. We get discouraged.


17 years ago I spent my summer in Paducah, KY. It was friggin hot. It was even worse because on a lot of days I was wearing an acid proof suit — those things are made of an unbreathable plastic something that doesn’t react with acid; see Breaking Bad and why you don’t use acid in your bathtub 🙂

Why was I in this suit? Because I was doing experiments at a uranium processing plant where we used a lot of hydrofluoric acid. If that sounds dangerous, it was. We’d have to carry gas masks around all day; go through radiation detectors; some guy had recently burned a hole through his shoulder from some tiny, accidental leak somewhere.

It was my first real gig doing chemical engineering, and I hated it. I mean, aspects of using my education were incredibly enlightening, but I didn’t want to work in plants like this after college.

Fortunately for me that summer, I broke my ankle.

They wouldn’t let me in the plant anymore for fear my cast would get contaminated with uranium. You know, typical summer intern problems. 🙂

It was fortunate because they stuffed me in a trailer outside the plant where I couldn’t get into too much trouble. And the only thing I could then do all day was use a computer. They’d give me Excel spreadsheets and ask if I could help them with some macros to speed up their calculations. It opened my eyes to what I really wanted to be doing.

I loved that work. Programming macros turned into me creating visual basic UI’s to make all these things that made the lives better of people around me at that plant. The feedback was instantaneous. Unlike the experiments I was doing that were dealing with all these messy chemical and physical problems people still couldn’t understand from decades of academic research, the computer obeyed my will, and allowed me to make so many people happy when it made their lives easier. I was hooked. I just dove in. Found everything I could about programming. Started making websites.

But then college was almost over, and I was still a chemical engineer, and instead, I wanted a job programming computers. So I took the closest thing I could get near the software business which was as a consultant for Accenture. And that sucked.

I was stuck gathering requirements all day. Typing up meeting notes. I didn’t have the skills for them to let me do any software engineering tasks. So I just kept at it. I’d bug all the engineers around me on what they were doing and learning. I’d go home and make more software. More websites. Try more things. Eventually I bugged enough people at work about the stuff I was making, they saw I had a hunger and new set of skills and they started letting me do some tasks on the side. I still had my requirements gathering and grunt work to do, but I’d stay after work for hours programming things for them, and learning some new reporting tools they had that they didn’t have time to learn yet, which included the ability to program UI’s to pull up the reports.

Eventually, I moved on from that role and they started putting me in software engineering roles. I still wasn’t any good. But I just sponged all the knowledge I could from the senior people around me. I did my work off hours too to see if I could make it better than they expected of me.

Eventually, I moved on from that company and was a pretty damn good engineer finally, and got a job at a software company.

Eventually, I moved on from that job and started creating my own software companies. First Inkling, where I was the CTO, then I was an engineer for the Obama campaign, then I made Draft (http://draftin.com) and then all of this led to Jason Fried and Basecamp picking me to take Highrise (http://highrisehq.com) and turn it into a separate company where I still get to write software every day.

So heck yeah, I’ve taught myself software development and make money at this. It wasn’t fast. It took at least a year of really hard work on the side to get people to give me some tasks that were programming related at work. And years after that before I’d say I was any good.

But it’s like anything. It takes practice. We suck at so much stuff when we start out.

I have a 19 month old daughter. She’s awful at everything.

Right? 🙂 Crashes into walls. Falls down constantly. Can’t figure this out or that. But we know she’s going to be awesome at this stuff she struggles with today. Look at how far she’s already come! It’s ridiculous how much she learns and learns and learns. And that doesn’t have to stop.

Don’t pick up software development if you’re just doing it for a paycheck or what you think the paycheck is going to be in the future. Pick it up because you like figuring out things like that. And I guarantee you, with enough practice and work, you’ll get better. And then better. And then better after that.

And as for the coding schools, I haven’t done any myself, but sometimes those are the best ways to learn for some folks. Some people get by with a book and a keyboard. Some really need the mentors and fellow students around them to bounce things off of. I would definitely experiment and check them out. I know people who’ve taken those courses and gone on to make their own things or gotten really great jobs. Claire Lew is a great example. She took a course at Starter League, and now Basecamp put her in charge of Know Your Company. That’s not everyone’s story of course. But let me share one more anecdote:

An acting teacher told his class of total beginners (which included me): “New York and LA are inundated with actors. It’s tough to make a career there. But… you can absolutely achieve it in Chicago. You won’t get everything you want all the time, but if you do the work you can get enough acting jobs, including commercials or industrial films, to make the money work. If you want to have a career as an actor, it’s yours.”

He absolutely believed that it wasn’t about what we looked like or innate talent we had at acting. If we wanted a career in acting, we just had to do the work.

And as I started watching the people around me succeed at acting, that’s exactly what they were doing. They were making a living at it. It wasn’t A-list Hollywood stuff all the time. Sometimes it was appearing in training videos about workplace sexual harassment, or chemical safety, or whatever. But those paid the bills so they could get up on stage every weekend to perform a play for a hundred people. The people with the rigid goal of Hollywood now or nothing? Those folks were bitter and gave up.

If you want a career in software, it’s yours. There is nothing stopping you from learning this. Just put in the work to learn it like anything else. It might take a bunch of only fair jobs before you’re good enough, but take what you can get and learn.


P.S. It would be awesome to meet you on Twitter, or see where this has all led to what I’m now doing with Highrise.

Employee benefits at Basecamp

Our headquarters in Chicago.

I’m often asked about the benefits we offer at Basecamp. Potential employees are obviously curious, but most of the questions I get are from fellow business owners and entrepreneurs. Everyone’s looking to know what everyone else is doing — as are we — so I figured I might as well post our current benefit list publicly.

Note: Since the majority of our staff works remotely, and some outside the US, some of these benefits are provided in different ways. For example, the 401k is only available in the US. We’re currently working on making sure everyone, no matter where they work, have commensurate benefits (or at least as similar as possible). We’re still working on this, so hopefully I can write more about how we’ve addressed this down the road.

Keep reading “Employee benefits at Basecamp”