Highrise 2015 — Getting Stuff Done

At the end of 2014, Highrise was spun-off from Basecamp so it could get some well deserved love, and boy did we give it some love last year.

I don’t how you guys accomplished so much. I really don’t. –dhh

One of the ways we’ve been able to accomplish a lot with such a small team (5 full-time, 1 part time) is by implementing a train schedule:

On day one, I established a train schedule — we’d make major announcements on a regular basis. If something isn’t ready, it misses the train. But an announcement is going out; something better be on it.

Another thing we try to make sure to do is to celebrate our successes. And the amount of improvement we’ve brought to Highrise over the last year is very much worthy of celebration. Here are just a few of our favorite things from 2015.

Top 3 we’re most proud of

These three level up the power you have in Highrise. We kept hearing from customers how important it was to make sure contacts were followed up with if they wrote in, how often people had to export contacts and spend more money to send emails from another tool, and that Deals could be so much more useful if they just had a bit more flexibility. Our solutions were Good Morning, Broadcast, and Deal custom fields.

Good Morning — your group inbox // 19-Oct

Broadcast — bulk email // 1-Dec

Deal custom fields // 16-Dec

But we’ve talked with so many customers and have heard many more important needs and insights. From those chats, we realized customers have too many steps getting data in and out of Highrise, so we’ve been nibbling away at them, making things more automatic and native to the tool itself. We’ve added things like the ability to connect directly to your Gmail account, and auto-forward all your mail from Gmail right into Highrise.

We also wanted to really extend our support for email. So we added the ability to help you collaborate and share important emails you find yourself sending over and over with:

And we rounded it all out with features you’d expect in a full class email client like:

We found we were often getting the same questions over and over, so we started making changes to the Highrise Help site, but found we really needed a complete redo. We released the new help site in July.

And once we did, we saw an immediate decrease in the number of tickets coming in. We love talking to our customers, but it’s even better when we can remove the step of having to reach out to us :).

Speaking of tickets, the number one thing that caused the most tickets is imports. There are so many ways an import can go wrong when trying to get data from one system into another. So we also completely redid how Imports work in Highrise. The biggest change was simply avoiding frustration with better indicators when we find something wrong.

And the number one feature request was an iOS app. We delivered a 5 star app early in 2015:

I have been using Highrise for many years and this new app is just the thing I’ve been waiting for!

Really, the above is just a few things we’ve done. We polished, tweaked, and improved so much more based on all the great feedback we’ve been getting. You can see the full (and much longer!) list on our blog.

And 2016 is going to see more of the same. Improvements to all the things we’ve already added, but we hear everyone loud and clear on what they need. Better reporting, an Android app, more powerful filters and custom fields. It’s all coming. 🙂

And if you haven’t checked Highrise out in awhile (or ever) now may be a good time! We’re just getting started.

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).”

Putting on the shipping goggles


One of the biggest challenges of shipping a product is knowing when to put on the shipping goggles.

The shipping goggles make you less sensitive to little nits and scrapes and things that might be able to be a little bit better, but really don’t need to be right now. Stuff that we could tweak, but really shouldn’t be grabbing our attention given all the other high value bits we need to hit.

It’s sort of like squinting — you lose the detail, but you can still see the overall big picture shape, form, and function. Your peripheral vision shrinks, but the center is still bright. Knowing when to squint is a good thing to know.

It’s not that the details don’t matter. They do, but details aren’t fixed — they’re relative. And of course any time you talk about details mattering, you’re speaking in very broad generalizations. Some matter, some don’t. Some never matter, some matter later, but not now. And some really matter now and can’t wait for later. Like everything, there are varying degrees.

Part of training yourself to ship is to recognize what details are really worth nitpicking and when. There are no hard and fast rules here — it just takes judgement and experience. These are skills that build over time. Once you’ve been around it for a while you tend to improve your sensitivity to what’s worth doing before you ship and what can wait until later.

And BTW, nitpicking may be construed as a pejorative, but I don’t believe it is. Nitpicking is a valuable skill, as long you deploy it at the right time for the right reasons. One of the penalties of nitpicking at the wrong time is that nitpicking often attracts a crowd. Someone nitpicks this which is an invitation for someone else to nitpick that. And before you know it, half a dozen people are spending time discussing tiny details that really don’t demand that level of attention.

Again, there are no facts around when it’s worth nitpicking and what’s worth nitpicking — I’m only speaking to the awareness how situations unfold.

We can all get better at this. I’ve been shipping stuff for years, but I still have to get better at recognizing the right moments to bring up certain things. I definitely fall into the trap of spending time making changes to things in the 11th hour that are really perfectly fine and can be addressed later if necessary. I absolutely find myself regretting going down a rabbit hole that really didn’t need to be investigated. I still find myself distracting others with change requests or suggestions that really didn’t need to cloud their vision and sap their attention. It’s hard!!

We just shipped and entirely new version of Basecamp! If you’ve got work to do, and it involves other people too, then Basecamp’s for you. It’s an entirely unique way of working.

A few words of advice to brain pickers

A few times a week I get an email from someone asking if they can pick my brain for 15 minutes. I appreciate their interest in what I might have to share, but when it’s pitched as a brain pick they’re making it hard to say yes.

I’m all for giving back, and I try to do it as often as I can, but I wanted to extend three quick points of advice to people who ask to pick people’s brains.

1. Picking someone’s brain sounds like an entirely one-sided appeal. Give me what’s in your head. That’s a hard sell — especially when you are pitching someone who’s busy and occupied with trying to focus on their own business. Whenever you ask someone for something, always ask yourself what’s in it for them? What can you do to fill their brain rather than pick their brain? So, rather than pitching it as all-take, try pitching someone some give, too. “I’d love to ask you a few questions about X, Y, Z, and at the same time share some perspective I have on A, B, an C.” Everyone has perspective, everyone has experiences that are unique to them. The more you can suggest that it’s a give and take, and that the person you want to talk to could learn something from you too, the better the chance of lining up the opportunity.

2. There’s no such thing as a 15 minute call, or coffee, or meeting with someone you don’t really know. It takes 5 minutes just to say hello and warm up. It takes another 5 minutes just to begin to get into a conversation. And then you’re left with 5 minutes — which is never really enough time to have a substantive conversation (which is the kind of conversation you really want to have). So just be honest and set the expectation clearly, because surely the other person doesn’t believe you’ll only be taking 15 minutes of their time. Suggesting it’ll only take 15 minutes either says to me you’re being disingenuous, or you aren’t sure what you really want to talk about. “I was wondering if you might have a full hour for an in-depth conversation about this product problem I’m struggling with… It’s…” makes me take you more seriously. I still may not have an hour, but I know you understand what you’re asking for.

3. Offer to come to them. When you are pitching someone, and asking for their time, you want to make it as easy as possible for them. And one of the best ways is to offer to come to them. Don’t pick a lunch spot or a coffee shop. Don’t even suggest a time (“lunch” is a time, “coffee” is a time). First suggest that you are willing to come to them or meet them wherever and whenever they prefer. That shows you’re courteous, concerned with their time (when they don’t have to go anywhere they save travel time), and it shows you are willing to make more of an effort to make the meeting happen. “If it would be easier, I’d be happy to come to you or meet you wherever is most convenient for you”.

If you follow these three simple rules, I think you’ll increase your odds of landing a meeting with someone. The odds may still be slim, but at least you’re setting yourself up to show that you 1. know what’s in it for someone else (you’re asking but you also have something to offer in return), 2. respect the true time involved to have a substantive conversation (and that that’s what you want to have), and 3, that their location and time is easier for them (and if it’s not, they’ll tell you).

Hope this helps!

The Fidelity Curve: How to weigh the costs and benefits of creating UI mockups

Here at Basecamp we do a lot of paper sketching. Usually we jump straight to code after making a rough sketch. But it’s not a black and white rule. Sometimes we make tappable prototypes to test an interaction, or a pixel perfect Photoshop image to communicate a concept. How do we choose which level of fidelity is appropriate for each project?

I think about it like this: The purpose of making sketches and mockups before coding is to gain confidence in what we plan to do. I’m trying to remove risk from the decision to build something by somehow “previewing” it in a cheaper form. There’s a trade-off here. The higher the fidelity of the mockup, the more confidence it gives me. But the longer it takes to create that mockup, the more time I’ve wasted on an intermediate step before building the real thing.

I like to look at that trade-off economically. Each method reduces risk by letting me preview the outcome at lower fidelity, at the cost of time spent on it. The cost/benefit of each type of mockup is going to vary depending on the fidelity of the simulation and the work involved in building the real thing.

Suppose we have four levels of fidelity…

  • Rough sketch (on paper or an iPad)
  • Static mock-up (eg. Photoshop or Sketch)
  • Interactive mock-up (eg. Framer, InVision)
  • Working code prototype (HTML/CSS, iOS views)

(I didn’t include wireframes in the list because we don’t make them at Basecamp. For us a rough paper sketch is the same as a wireframe, without the extra time wasted on sharp lines and shiny presentation.)

Depending on the feature you’re working on, these levels of fidelity take different amounts of time to create. If you plot them in terms of time to build versus confidence gained, you could imagine something like a per-feature fidelity curve.

Eg. take a simple CRUD web UI, where you’re just navigating between screens.

A fidelity curve for a simple feature. Building real code doesn’t take much more time than faking it.

It doesn’t take much more time to build the real version than it does to mock it when the design is simple. If you were to build out an interactive mock first, you would end up spending twice as much time in total without gaining much out of it.

Going straight to real code is more worthwhile for a simple web UI.

Contrast that with a complicated Javascript interaction. Or a native iOS feature that requires programmer time to build out.

The curve is different for a complex web or native app UI.

If it takes substantially more time to build the real code version, then it may be smart to do an interactive mockup first.

Here’s one thing to be very careful about. If you put too much fidelity into anything that’s not code, you can end up spending lots of time on deliverables that are thrown away in the end anyway. This often happens when people fiddle with colors, positioning, fonts, etc too early.

Spending time on unnecessary details stretches the curve.

These illustrations show that mockups aren’t good or bad, and there isn’t a black and white answer for when to make each kind. But there is a trade off to be made. Being conscious of that trade-off can help you make more rational, economic decisions when people have differing opinions about what to do next in a design process.

We still mainly draw rough sketches on paper or on our iPads when we’re working on UI for Basecamp 3. Now that we offer full-featured iOS and Android apps, I’ve learned that prototyping tools can be useful before building the heavyweight UI code those platforms require. See Basecamp 3: Mobile Prototypes for more.

Why are some people so much luckier than others?

James Scott Bumgarner, more famous as James Garner, film and TV star, passed away recently at the age of 86. Many people shared how great a guy he was and stories about his life.

A few things caught my attention. Not the least of which was how lucky he seemed. How does a guy without any acting experience and who hates talking in front of people land a well connected Hollywood agent to jumpstart his career? Luck?

In 1935, Hollywood created their talent scout system. Just like athletic scouts, folks would monitor Broadway plays and radio for talent. But occasionally they’d “discover” someone in public who didn’t have any acting experience — they just looked like a movie star.

Lana Turner, one of the most glamorous and popular female stars of Hollywood during the 40s and 50s (pictured here at the right with James at the 1966 Academy Awards), is a great example.

She was 16, ditching a high-school typing class and drinking a Coke at a soda shop in Hollywood, when someone spotted how attractive she was. He recommended her to his Hollywood agent friend and soon she was in a movie. Gorgeous girl — right place at the right time — lucky.

James had a right place at the right time story, too.

Before acting, James Garner had dozens of different jobs. He’d work them a few months, save money, quit, coast for awhile, and then find the next thing.

At 17, one of James’ jobs was pumping gas at a Shell station in Hollywood. That’s where James met Paul Gregory who worked at the drugstore across the street manning the soda fountain.

But Paul Gregory had a dream of being a Hollywood agent and talked about representing James.

James after all was good looking — enough people told him so. But James had no intention of being an actor. He just laughed it off.

Years later, James was coming back from a tour of duty in the Korean War and he spotted Paul’s name in Newsweek. Paul was now a stage producer with three big hits.

And about a year after that, while visiting LA and driving back from a failed attempt at getting a job drilling oil wells in Saudi Arabia, James spotted a sign: “Paul Gregory and Associates”. He wasn’t planning on stopping, but all of a sudden he noticed a parking space open up in front of the office.

James parked the car, went inside to visit his old friend, and Paul immediately decided to become James’ agent, send him to acting school, and help get him a job. The rest is a brilliant career in television and film.

It reads like another guy-gets-lucky-in-Hollywood story. But is it?

success or failure apparently brought by chance rather than through one’s own actions

Richard Wiseman was a professional magician before he became a famous psychologist. Given his interest in magic, he has a healthy dose of scepticism for things like superstitions and good luck charms. So Wiseman has spent a good deal of his career studying luck.

In one experiment, Wiseman asked people to self identify themselves as lucky or unlucky. Then he gave his test subjects a newspaper. “Count the number of photographs inside”, he told them.

There were 43 photographs.

On average, the unlucky people took 2 minutes to count them all. The lucky people? Seconds.

The lucky people noticed the giant message that took up half the second page of the newspaper. It said, “Stop counting — There are 43 photographs in this newspaper.”

The unlucky people missed it. They also missed the equally giant message half way through the newspaper, “Stop counting, tell the experimenter you have seen this and win $250.”

The “lucky” people weren’t lucky. They were just more observant.

And James was observant.

James fought in the Korean War and had more than a few close calls with death. James explains in his autobiography, The Garner Files, an event that could have turned out disastrous:

Like our South Korean allies, the Chinese and North Korean troops lived on a diet of fish heads, rice, and garlic. One night while on guard on the line, I caught a faint whiff of it coming from the direction of the enemy positions. I couldn’t see anything, but I knew there was someone out there and they were coming closer. Once I sniffed them I could hear them, too. It turned out to be a patrol heading straight for our position. They were just the other side of a rise when I passed the word down the line. We were ready for them and stopped them in their tracks.

His observation of enemy troops nearby likely saved a bunch of his fellow soldiers lives including his own. But it wasn’t James being lucky. It was James being observant.

Wiseman notes from his research that unlucky people also identify themselves as being tense and anxious, so he performed another experiment to confirm how anxiety affects people.

He had one group of people watch a moving dot on a computer monitor while other large dots flashed on the screen. They noticed the large dots. He did the experiment with a second group of people, but this time he offered a financial reward to make them more anxious. This group missed a third of the large dots that appeared.

Anxiety focuses us, but it also becomes an obstacle to observing opportunities in our lives.

One thing you notice from people talking about James’ life is how relaxed the guy was.

Appreciating the relaxed genius of the late James Garner.


RIP James Garner. One of my favourite cool actors. Always looked so relaxed on screen. A proper film star.

Russell Kane (@RussellKane)

James had a reason to be relaxed.

He and his brothers grew up in a home of mental, physical and sexual abuse. His father would force the kids to sing, and if they didn’t he’d whip them. His stepmother raped his teenage brother and beat the boys constantly.

If that wasn’t terrible enough, James grew up during The Depression in Oklahoma, meaning he, his family, friends and neighbors battled things like the Dust Bowl.

You want to put pressure on somebody, live through the Depression. In Oklahoma. In the dust. After that, studio executives don’t bother you at all.

James didn’t worry about much because nothing could be as bad as the life he had already lived.

Wiseman also found lucky people go out of their way to try new things and meet new people.

Remember all those jobs James had?

And James knew everyone: crew, cast, people in the towns he’d film in. Gretchen Corbet, one of the co-stars in James’ series, The Rockford Files, remembers, “Everybody loved him — but he took care of not only the actors and me but the whole crew. He knew everybody’s name, he knew everybody’s kids’ names.”

This wasn’t just after he was famous. He was doing it constantly.

I used to go around with the three of them — [Henry] Fonda, [Johnny] Hodiak, and [Lloyd] Nolan — as a sort of bodyguard-gofer-mascot.

At the table reading on the first day of rehearsals, Lloyd never had to look at his script. Everybody else was reading their lines, but Lloyd was letter-perfect…Fonda was amazed, because Queeg was a difficult part. “How the hell did you do that?” he wanted to know. “I hired Bumgarner,” Lloyd told him. So Fonda asked me if I would cue him, too, and I gladly agreed.

James considered himself an introvert. But that didn’t mean he didn’t take every chance to befriend someone else. He was happy to clean movie stars’ dressing rooms, or help them remember lines, just to get closer to new people.

One last point from Wiseman’s research — lucky people think the things that happen to them are lucky, even if they’re the same things that happen to the unlucky people.

In another experiment, Wiseman asked his lucky and unlucky test subjects how they would describe a hypothetical situation where the subject was in a bank, and a bank robber comes in firing his gun, shooting the subject in the arm. Unlucky people lamented about their terrible luck at being in the wrong place at the wrong time.

Lucky people were thankful — the situation could have gone so much worse. One of Wisemen’s lucky subjects noted, “It’s lucky because you could have been shot in the head.”

Again, given James upbringing, you get the sense that he too felt like anything after that traumatic childhood was just a blessing.

In a story James has about having to share a motel room with two other guys:

There were only two beds so I slept on the floor. The two Marines stayed up all night moaning about how unhappy they were — it was their first Christmas away from home and we were all just teenagers — but I was quiet on the subject. They were depressed and homesick, but there I was, lying on the floor, happy as can be.

It’s easy to look at successful people and chalk up their achievements to good luck. And sure enough, some people really do just win the lottery, or get born so beautiful that someone notices them on the street and puts them in a movie.

But if you go back through James’ story:

Paul Gregory was just one of many, many friends James kept making. He noticed his friend’s name in Newsweek, that sign in Hollywood, that parking space that opened up not because he’s lucky, but because he’s so keenly observant. And of course he’s observant; he’s one of the most relaxed people you could have met. He’s just happy to have gotten through that horrific childhood.

Is James Garner luckier than you or me? Maybe. But that’s because James Garner created his own luck.

When I started acting, I didn’t have a clue what I was doing. I was just stumbling around, hoping to get lucky.

P.S. You should follow me on YouTube: youtube.com/nathankontny where I share more about how we run our business, do product design, market ourselves, and just get through life. And if you need a zero-learning-curve system to track leads and manage follow-ups, try Highrise.

Reducing Incident Escalations at Basecamp

Incidents escalated to PagerDuty are generally “all hands on deck”.

tldr; The bottom line is that we had fewer actual site down interruptions and false alarm escalations in 2015.

Here’s a non exhaustive list of contributing factors to these improvements over the years:

  • Eliminating scheduled maintenance that would take a site offline
  • Limiting API abuse (and a general decrease in the number of abuse incidents)
  • Automated blocking of other common abuse traffic
  • Fairly generous ongoing hardware refresh with better distribution across cabinets
  • Completely new core and top of rack network switches
  • Hiring the right people (and the right number of people)
  • Moving to more stable storage (EMC / Isilon to Cleversafe)
  • Taking control of our public Internet connectivity and routing (Our own IP space, our own routers, carefully selected providers, filtering traffic)
  • Right sizing database hardware for every major application
  • Better development / deployment practices and consistency in following those practices (local tests / ci, staging, rollout, production)
  • Practicing incident response and keeping play books up to date
  • Vastly improved metrics and dashboards
  • Better application architecture and design choices with regard to availability and failure modes
  • Being ruthless in our tuning of internal monitoring and alerting (Nagios) to only escalate alerts that really need to be escalated
  • (Full disclosure we actually had more incidents escalated from our internal monitoring this year. The “quality” of those escalations is higher though.)

“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.


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.