Inactionable advice

Enough with the actionable advice, already.

Let’s see some questionable advice instead.

Rather than guide with steps, stump with challenges.

Fewer answers, more questions.

Less following, more foraging.

More wonder, less known.

Figure it out yourself.

The Also/Or Dilemma

http://rework.fm is the result of OR, not ALSO.

For three years, we wrote, produced, recorded, and published a podcast called The Distance. Over nearly 60 episodes, we told stories about small private companies that had been in business for 25 years or more. The premise was that there’s a lot to learn from businesses that have figured out how to not go out of business. And there was.

Then, earlier this year, while The Distance was still going strong, we had an idea for another podcast focused more broadly on how to run a better business. One with our own point of view, not just other people’s stories.

Awesome — time to launch another podcast! Wait, not so fast. First we had to make a choice: We could continue doing The Distance and start a new podcast. This would mean running two podcasts. Or we could stop running The Distance and start a new podcast. This would mean running just one podcast.

This is a scenario many companies confront. I call it “also/or.” These two seemingly innocent words determine wildly different outcomes.

Most companies, products, and services start out simply. It’s rare that the first version of something is more complicated than the second.

But once a company starts saying yes to one good idea after another, it starts accumulating scars. And scars they are. When companies decide to do something and it works, it usually doesn’t go away. Ideas turn permanent. Before you know it, things aren’t so simple any more.

Saying yes to more and more good ideas without dumping some of the earlier commitments invariably leads to a place of compounding complexity. Too many good ideas eventually combine to make one big bad idea.

You see this all over software today. Setting after setting, preference after preference. Each one is an example of a company’s refusing to make a choice and offloading the decision to the customer. It’s sold as customization, but it’s often just one “also” after another.

By forcing a tradeoff on every new “yes,” you corner yourself into considering the value of something. And only once you value a thing accordingly can you make a better decision about what is worth pursuing. It requires you to reconsider: Is this still worth doing? Would we be better off doing something else? That’s a healthy exercise from time to time. The true test of how bad you want something is whether you’re willing to give up something else to make room.

So what did we end up doing?

The choice wasn’t obvious. It’s easy to end something that’s a clear failure. It’s much harder to end something that’s doing fine or better. The Distance was doing well. According to the number of weekly downloads and industry data, it was in the top 10 to 15 percent of all podcasts.

We debated it internally, and we chose “or.” Ultimately, we felt The Distance had had a great run, and that ending it on our own terms meant we could make room for something new.

For the new podcast, called REWORK, we didn’t have to hire more people, increase the size of the crew, or attract audiences for two different podcasts. We’ve released a half-dozen episodes, and we’ve already more than doubled the audience we got for The Distance. And it’s growing fast.

The next time you’re faced with this kind of decision, stop and think about the language. Instead of saying “Yes, we’ll do that also,” you have to practice saying “Sure, we can do that instead.” “Or” always forces a choice, and that’s a good thing.


This article also appears in the November 2017 issue of Inc. Magazine.

From an internal Basecamp announcement re: pings/IMs


Direct/instant messaging is something many people are doing more and more often at work. And while it’s a handy way to quickly get ahold of someone, it’s a forceful interruption often coupled with an expectation of a quick response. That makes it costly communication. And that’s why the etiquette around it is important.

Recently we noticed some internal behavior around pings (Basecamp 3’s name for direct/instant messages) that we didn’t like. David and I discussed it and we decided to post an internal announcement to everyone at Basecamp detailing the problem as we saw it. We also suggested ways to improve the efficacy of a ping, and reduce the burden of empty notifications for everyone.

I figured this might help other people outside our walls, so here’s the announcement in full (and here’s a link to the announcement in Basecamp itself if you want to share or reference it elsewhere):


📢 “Ping” / “You there?” / “Yo” / “Hey”

Direct one-to-one (or small group) messaging is an important part of working together. It’s very useful in a variety of situations.

But there’s a dark side. I’ve been seeing it crop up more and more, including in my own behavior, so I wanted to call it out and make sure we’re all aware of it (and stop doing it).

Do you ever start a ping with someone by first trying to get their attention? You say “ping” or “there?” Or “hey!” Or “Yo” (or whatever). You begin with a whistle, and then you only send the rest of your thoughts once someone has whistled back. I do this all the time. It’s time to stop.

Sending a ping with no information would be like sending an email with a subject “Hey” but with no body. Then only when someone emailed you back saying “What’s up?” would you follow up with a separate email containing your complete thought. That would be silly, but it’s exactly what we’re doing with pings.

What’s worse, compared to emails, pings are very interruptive. Being pulled away from your work to check out something with no information in it is bad for everyone involved.

So, let’s think of pings more like emails. You wouldn’t send an email asking if someone’s around to respond. You’d send the email — a complete thought — and someone would eventually get it, read it, and respond in kind. So when we send pings, don’t lead off with an empty “you there?” question. Instead, share the complete thought so when someone sees it they can respond with an answer, vs a “Yeah, why?”

So instead of…
Me: Ping. You: What’s up? Me: Got time to catch up today at 3:30pm? You: Sure. Me: How’s team room 2? You: Perfect, see you then.

You’d send…
Me: Got time to catch up today at 3:30pm to review the latest breadcrumb design? You: Yup, how’s team room 2? Me: Perfect, see you then.

In the first example, I started with a whistle — just an empty “Ping”. You had no idea why I was writing, so you had to respond with another empty whistle back.

In the second example, I my initiation included my complete ask. When you see it, you respond with a complete thought back.

The differences are subtle, but meaningful — especially when multiplied by the hundreds of initial pings we each likely receive every year. If you’re going to reach out and talk to someone directly, give them information to act on, don’t just whistle at them and wait for them to ask what you’re whistling about.

This should help introduce a bit more calm into direct messaging. It should cut back on the number of individual notifications, and also help everyone get to the point quicker so they don’t get pulled away from their work without a clear reason.

If I ping you with a “ping” or “hey” or “there” — please call me out on it!

— Jason


David added a comment:

Couldn’t agree more, and I want to cop to being as guilty of this as anyone.

In addition to using pings with greater care, I think it’s worth considering when posting the purpose of your ping as a fully formed message or todo in a fitting project could work instead. I’ve often pinged someone about something that really just needs to be a todo request or a message to the team. I will do better.

One way I’ve been thinking about pings is this: If we were in an office, would this be important enough for me to walk over to someone’s desk, interrupt them in whatever deep thought they might be in, and ask this? The answer is frequently no.

And it’s even worse with pings because you can’t see the rest of the foot traffic. Your interruption may well just be a quick question, but it may also well be the fifth someone had to field that day.

None of this means you shouldn’t ask questions, or seek help, or get input. Just that you should think about the timeliness of your requests and what format is the best fit.


I hope this was useful.

Look elsewhere

Entrance to the theater at Frank Lloyd Wright’s Taliesin. Spring Green, WI.

Don’t stare at your industry. Look in the opposite direction.

Have you noticed that Instagram has been looking more and more like Snapchat lately (of course you have)? When companies compete, they tend to borrow from each other. It’s one big, paranoid loop.

In software, people often turn to Apple for design inspiration. It makes sense — the company is wildly successful, it defines trends, and it pushes envelopes. But copying Apple doesn’t make you a trendsetter or a rule breaker. It makes you a follower. When everyone mimics Apple, everything tends to look the same. Apple’s clean and simple aesthetic is Apple’s — it’s not yours.

So here’s my advice: Look outward. Turn away from your industry and venture beyond the business world for inspiration. If you’re about to make software, instead of checking out the Top 10 apps in the App Store, try looking through a book on architecture.

Better yet, find a building that moves you and walk through it. Spend time understanding it. How do people flow from one part of the building to another? Is there signage? How do you know where you are in the building? How do you feel when you look at it from across the street? How does that feeling change when you walk inside? How do you feel when you leave?

All those experiences and observations relate to designing software. It’s about thinking through an experience, not drawing exact parallels. For example, bronze elevator doors tell you there’s a heft and heaviness and seriousness to the building. They make you feel secure. Contrast that with flimsy elevator doors that shake when they close, which gives you a sense of unease. How does your software make someone feel?

When I’m designing software, I try to draw from a variety of influences, including:

Nature

Want to find colors and patterns and shapes that go well together? Stop looking at catalogs of print designs or stock photos — look at trees and flowers and insects and animals. Their designs have been perfected over millions of years. They have beauty and utility figured out by now.

Watches

At their most basic, they all do the same thing — tell time with just three components: a minute hand, an hour hand, and markers on the dial. It turns out there are thousands of variations to accomplish this simple task, so don’t tell me there are only a few ways to display photos in your app.

Cars

I love looking at well-designed dashboards, instrument clusters, door handles, switches, and buttons. There’s so much to learn about what feels right and what falls flat. Sounds are telling as well — the engine, the snick of a manual shift, the click of the turn signal, the confident thud of a door that closes snug and tight. Those are all design features.

Chairs

A chair is such a basic device, but it can take thousands of forms. What does it feel like to sit in a chair that is nailed together, versus one that is glued or joined? What does a cotton-webbing seat feel like compared with wicker? Arms at different heights — or no arms at all?

The details may be different in software, but the feelings are the same. Other companies may prefer a serious museum look, and there are plenty of products that resemble museum pieces. But if you want something that’s comfortable and welcoming, Basecamp’s going to be more your speed. It has a “come on in and get cozy,” living room feel, not a cold, modern, “don’t touch it or you’ll mess stuff up” vibe.

So figure out what objects and places inspire you and immerse yourself in them. Pay attention to those details. Then, instead of imitating competitors, you just might find your voice.


This article also appeared in the June 2017 issue of Inc. Magazine.

New in Basecamp 3: An all-new Schedule design

Big update today! Starting right now, Basecamp 3 customers will see an entirely new design when they flip over to the Schedule screen in any team, project, or HQ.

The schedule used to look like this…

BTW, this is the actual schedule for our all-new REWORK Podcast.

It was colorful, and it provided a nice overview if you only had a few events, but it quickly got out of hand if you had a lot of events or to-dos mixed in. And when you wanted to get in there and see exactly what was happening next week, or if there was anything on the schedule this Friday, it fell down pretty hard.

So we fixed it. And more!

And here’s the new schedule…


At the top you have a grid showing the current month + the next month. You can page through the months using the arrows top left and right. Every event or to-do that’s due on a given day is represented by a dot. Three events, three dots. If there are no dots, there’s nothing on the schedule for that day. Now you can see gaps and openings and weekly overviews — something that wasn’t possible with the previous design.


A LIGHT project on the left, a HEAVY project on the right.

Below the grid is a straightforward agenda view. Events are clearly grouped by days (if there’s anything on a given day). And you can jump around the agenda view by clicking around in the calendar above. Want to see what’s happening next Wednesday? One click and it pops right to the top of the agenda view. This was something you couldn’t do before.


Events (or to-dos) that span multiple days are shown in a couple ways. First, if they’re on the current day, they show an “Until” right under the event. And then, they’re shown in light grey at the top of subsequent days. They’re also repeated on every future day so you can get a very direct sense of what’s happening on a given day. You couldn’t see this in the previous design because they were only shown at the top of a month, and not on individual days where the event occurred.

See how “KA Sabbatical” says “Until August 27th” below it at the top? Now you know KA will be out until the 27th. And on the 24th you’ll also see “KA Sabbatical” at the top along with “JS Out” “AB Out” and “CJ Out” — the other long-running events that continue that day.

One of the really nice benefits of this is that you can see overlapping long-running events. In the example below, you’ll see Tom is out on sabbatical, and then “SU” starts his sabbatical on the 23rd. Now from June 24th — 30th you’ll see they are both on sabbatical. This was non-obvious in the previous design. Now it’s clear as day.


Here’s another before and after. Before on the left, after on the right…


← Before ……………………….. After →

You’ll notice the previous design (on the left) doesn’t show that KA, JS, AB, and CJ are even out on the 24th— you’d have to go back up to the top of that month to figure that out. Forget to do that, or not even realize you have to, and you’re missing out on important information. This is fixed in the new design.

Lastly, we’ve pulled this design over to two more places: “My Schedule” and the “What’s coming up” report. An example:

This report shows what’s coming up across all teams and projects across your entire account. You can see we have a lot scheduled in August, but things begin to lighten up towards the end of September.

Summarizing the improvements on the new schedule design:

  • Jump to any day to see exactly what’s happening that day. Just click a cell in the grid at the top of the schedule and the agenda below updates instantly with the selected day right at the top.
  • Now you can see gaps in time. Looking for an empty day to schedule something? Now it just takes a quick glance at the grid at the top to spot openings.
  • See busy days or weeks at a glance. Lots of dots tells you there’s a lot going on on a specific day or week. Just click into a cell to see exactly what’s up.
  • See long-running events on every day they occur. You no longer have to scroll back up to earlier in the month to see if there’s something happening on a given day.
  • Jump back in time using the same interface. Previously, if you wanted to see past events you had to flip to a separate tab called “Looking back”. This wiped the screen clean and listed old events. It was cumbersome to see something that happened yesterday. Now you just navigate using the grid at the top and jump between future days and past days the exact same way.
  • Plus a variety of smaller improvements, specifically around speed and performance.

One more thing… Now that you have a calendar view up top with dots that represent events, you may be wishing for a way to assign colors to different kinds of events. We agree! While we haven’t built this into this first revision of the schedule, it’s something we’d like to do down the road.

So there you have it. An all-new and improved schedule, available today in your Basecamp 3 account. You’ll see the same design in the iOS and Android apps as well!



We hope you find the new design useful, and thanks again for your continued support.


If you’re a Basecamp customer, thanks so much! And if you aren’t, but you find yourself struggling with messy email chains, overwhelmed by chats and txts, finding stuff slipping through the cracks, and generally feeling like your process is breaking down, it’s time to give Basecamp 3 a shot. It’s free to try.

On being a bad manager

A fellow I admire just asked me why it’s so easy to be a bad manager. Goddamn, that’s a fantastic question. I made some bonehead moves myself yesterday, so I’m in the perfect position to answer this one.

Because I didn’t want to overthink my answer, I told him I’d write something up this afternoon and send him a link.

Here goes, stream of consciousness, unedited, and quick…


We’re bad at most things by default. The only way to overcome the deficit is with the right kind of practice.

We can practice badly and get over small humps, but if really want to break through from bad to good — or to great — we have to put in deliberate, focused practice. And plenty of reps.

With some things this is straightforward. Want to get better at a sport? There are clearly documented methods and approaches to practice. Want to get better at playing guitar, the drums, or the sax? Same thing.

But with those, even if you practice poorly, a certain number of reps will get you somewhere. And the reps are easy — you can sit down and practice the drums for hours, if you have the time.

But have you tried to manage for hours? How do you even practice management?

Professional athletes keep getting better at the same thing. They start playing a sport at a younger age, and gain expertise and experience in that same sport as they practice over the years. Professional basketball players play the same game at 5, 10, 15, 20, 25, 30 — they just play better.

But professional managers don’t start as managers. They’re generally promoted to management. They’ve actually spend most of their lives, and careers, doing something else. So by the time they’ve made manager, they’re beginners again. 3000 days into their career, they’re actually on day one. So, when they start, they’re probably not going to be very good. No different from the first day you pick up a guitar.

Sure, you’ve listened to music for decades. But your first day on guitar sucks. Just like you may have watched people be managed — and you were likely managed yourself. That doesn’t prepare you to pick up the management instrument and strum a beautiful melody. Observation is no substitute for doing.

There are more reasons too, of course. People are wildcards. Humans are emotional — that includes you! And it takes a while to really get to know someone in a way where you can predict their outcomes. Throw something at them, and they’ll react that way. Hand the same thing to them, and they’ll react another. Pick something up together, and there’s yet another reaction.

So people are complex, outcomes are often unpredictable. Over time, with experience, you get better at feeling out outcomes. Your if this then that prediction ratio improves. But the only way to really get that experience is to flub a bunch of shit for a while. Just like how you keep missing the A to G chord change. You have to keep playing, working on your timing, improving your hand strength, etc.

Managerial trials and reps are much harder to come by. And when you practice being a manager, you’re already on stage. Your flubs have consequences. Fucking up could cost you or someone else their job. It could cost a business money, customers, reputation. But when you practice guitar you can sit in your basement, alone. No one cares, and there’s nothing at risk, if your pinky can’t stretch three frets quite yet.

I don’t know… There are a lot of reasons it’s so easy to be a bad manager.

Another reason is that you feel like you have to contribute when there’s really not a lot you should be doing most of the time. Many managers over-involve themselves. Not even micromanage, but are simply around the work being done too often. They get in the way. It’s an easy mistake to make when you’re trying to prove yourself. Especially early on when you’re job title doesn’t really line up with your experience. You’re still just practicing.

And then there’s assumptions. Holy shit, managers — and this absolutely includes me — make too many assumptions about what people know or don’t know. Managers are often privy to information above them that hasn’t yet filtered down below them. But they’ll often assume there’s a symmetry. “Of course they should know that”… Actually, it’s more likely they won’t know that. When you assumed they’d know, you stopped the flow.

Great managers help fill the gaps so no one has to jump over a chasm to come to a conclusion. It takes a while to get good at even seeing the gaps. Then it takes even more time to get good at filling them.

“I had no idea they’d react that way” are the words of an inexperienced manager. Good managers are rarely surprised at how people react. And the only way to eliminate surprise is to have seen it all before. And a honed sense of empathy. That takes living it. Books, classes, and simulations won’t get managers there.

Here’s another assumption: Someone on your team will internalize the news the same way you would. Probably not. Everyone hears the same words differently. Words are always filtered through previous experiences, and everyone’s experiences are different. Good managers recognize this, but it’s a common mistake from new/bad ones.

The hardest thing about business isn’t the business part, it’s the people part. Business is ultimately digital. People are analog. And as teams shift, grow, or downsize, and teams from different departments collide, all sorts of energy can be released. And it’s not always good. Until you’ve seen this happen a bunch of times, and until you’ve had the chance to corral the energy and send it in the right direction, you’re probably going to make a mess of it.

Now some people simply suck as managers, no matter how much they try to get better at it. Management probably isn’t the right job for them. It’s surely not for everyone, but the corporate world puts that target in everyone’s career path. It’s unfortunate that management is the primary way to progress in one’s career. It’s often a regression.

That’s what comes to mind. Raw.

Was this helpful at all? Am I even close?

Three’s company

Three is lucky enough.

At Basecamp, three is a magic number.

Nearly all product work is done by teams of three people. A team of three is usually composed of two programmers and one designer. And if it’s not three, it’s two or one — not four or five. We don’t throw more people at problems, we chisel problems down until they can be tackled by three people, at most.

We rarely have meetings at Basecamp, but when we do, you’ll hardly ever find more than three people around a table. Same with conference calls or video chats. Any conversation with more than three people is typically a conversation with too many people.

What if there are five departments involved in a project or a decision? There aren’t. Too many dependencies. We don’t work on projects like that — intentionally.

What is it with three? Three is a wedge, and that’s why it works. Three has a sharp point. It’s an odd number so there are no ties. It’s powerful enough to make a dent, but also weak enough to not break what isn’t broken. Big teams make things worse all the time by applying too much force to things that only need to be lightly finessed.

The problem with four is that you almost always need to add a fifth to manage. The problem with five is that it’s two too many. And six, seven, or eight on a team will inevitably make simple things more complicated than they need to be. Just like work expands to fill the time available, work expands to fill the team available. Small, short projects become bigger, longer projects simply because all those people need something to do.

You can do big things with small teams, but it’s a whole hell of a lot harder to do small things with big teams. That’s a disadvantage of big teams! Small things are often all that’s necessary. The occasional big thing is great, but most improvements come as small incremental steps. Big teams can step right over those small moves.

Three keeps you honest. It tempers your ambition in all the right ways. It requires you to make tradeoffs, rather than keep adding things in. And most importantly, three reduces miscommunication and improves coordination. Three people can talk directly with one another without introducing hearsay. And it’s a heck of a lot easier to coordinate three people’s schedules than four or more.

We love three.

Lots of new Basecamp 3 stuff

We’ve been plugging away this summer on a wide variety of improvements on Basecamp 3. While there have been a ton of improvements on the iOS and Android side as well, this post will focus on some of the larger improvements to the web/desktop version.

Focus Mode

Need to do some deep work? Go into Focus Mode. This will turn off all notifications, and hide all unread badges.


To enter Focus Mode, click your avatar top right, and click the “Turn on Focus Mode” button.

Color and highlight your text

Lots of requests for this one. Now you can color and highlight your text in messages, automatic check-in answers, comments, to-dos, etc. Basically anywhere you can turn text bold, italic, etc, you can now also color it up.


Just click the dropper icon in the toolbar to add some color.

Quick jump to projects, teams, recently visited pages, and people

Big one. No matter where you are, hit COMMAND-J (Mac) or CONTROL-J (windows) and you’ll pull up the quick switcher. Just start typing to filter down and jump to another project, team, recently visited page (a to-do list, a message, a file/document, etc), your HQ, your assignments, your drafts, or other people.

Type someone’s name to quickly see what they’ve been up to, what’s on their plate, etc.

No more duplicated notifications on @mentions

Prior to this update, if you were @mentioned on a thread where a new message or comment was posted, you might get two notifications: One for the posting itself, and another letting you know you were mentioned in the posting. We’ve collapsed those two notifications into a single one. Now you’ll only get the @mention. This is better.

Automatic titles for Basecamp 3 links

Now, when you copy a Basecamp 3 URL and paste it into a Basecamp 3 message, comment, or document, we’ll automatically link it up using the title of the page as the link text.


My Schedule

There’s a new link on the home page below My Assignments and My Bookmarks called My Schedule. Click on that and you’ll see every upcoming event that you’re associated with.


Bulk to-do move and copy

Major workflow improvement: Now you can shift-select multiple to-dos on a list and move or copy them together to another list.


First you select which, then you say where.

Added list view to the home page

When we launched Basecamp 3, all teams and projects were shown as cards. We recently pushed an update which allows you to view teams and projects in a list format. You can control teams and projects independently — teams can remain cards while projects can be shown as a list, etc.

Pick your poison.

Add a personal note to invitations

Now when you invite people to Basecamp, you can include a personal note. It’s a great way to explain why you’re inviting someone, or give them a short introduction to Basecamp itself.



Message types

This one’s really useful: Now you can specify what kind of message you’re posting. You’ll see a series of options at the top of the “New Message” screen. If you pick one, the emoji will precede the message subject, making it more obvious from the start what kind of thing you’re publishing.



All-new emoji picker for Campfires and Pings

Just click the little smiley on the right side of the Campfire or Ping text entry box and you’ll see a panel with common emojis you can pop right into your message. You can always use any emoji you’d like — even ones not represented here — but this provides quick access to the most common ones.


Flexible scheduling for Automatic Check-ins

Basecamp 3’s Automatic Check-ins feature has been a game changer for so many of our customers. Automatic Check-ins prompt people, on a regular basis, to share specific kinds of information. Things like “What did you work on today?” “What are you planning on working on this week?” “How do you think this project is going so far?” “What’s inspired you lately?” etc. Originally we only provided a few recurring options — every Monday, every Friday, every other week, etc. But with this update you have far more flexibility in how often they’re asked, and when.


…And many more subtle tweaks, adjustments, and improvements.

Every day we’re improving Basecamp 3, and every 6–8 weeks we tend to ship significant improvements. We’re working on some great stuff now — we look forward to rolling it out when it’s ready.

Stay tuned to this blog, or follow us on Twitter at https://twitter.com/basecamp to stay up on the latest.

If you’re a customer, thanks so much! And if you aren’t, but you find yourself struggling with messy email chains, overwhelmed by chats and txts, finding stuff slipping through the cracks, and generally feeling like your process is falling apart, it’s time to give Basecamp 3 a shot. It’s free to try, and there are no limits during your 30 day trial.

One door at a time


Entrepreneurs are told to go big or go home. Stop obsessing over scale, and perfect the basics instead.

Last year, I met a first-time entrepreneur who was opening a tea shop. We’ll call him John.

At the time, he had a pop-up shop in my neighborhood. I really liked him, his vision, and the quality and presentation of his tea, so we kept in touch. When he decided to go from pop-up to permanent shop, he asked for my advice.

While we were talking about this permanent shop, which he still hadn’t opened, his attention would often drift to his next shop. And the one after that. And after that. And then building an app to make online ordering easy. And then, becoming the next Starbucks.

Whoa. Hold on, man, I told him. I get it, scaling the business seems sexy. But, I said, that is the entirely wrong thing to think about now. I wouldn’t spend even a second on it. You have a serious challenge in front of you: opening your first real store and getting your first customer (that isn’t a friend or family) in the door.

In getting just one store right, everything is against you. You have to design and build out the physical structure. You have to hire good people to run the shop when you aren’t there. You have to train those people. You have to get the menu right. You have to get the pricing right. You have to get the presentation right. You have to get customer service right. You have to get customers in the door. And then you need to get them to come back.

So much to get right in the here and now. Not down the road, but today.

I’ve noticed that John isn’t alone in his desire to go big. Something’s changed in what’s expected of the entrepreneur. Ten years ago, people were excited to just start a business, to create their own thing so they didn’t have to go work for someone else. They wanted to make a good living, buy a house, and be able to pay for their kids’ college.

But now, entrepreneurship seems like a sport. And the score depends on scale. How big can you get? How fast can you get big? How much power can you amass in the shortest possible time?

There are lots of forces pushing this scale-it-up, go-big-or-go-home mirage. Business schools are guilty of pumping pipe dreams into students’ heads: If you follow this framework, you can become the next Howard Schultz or Mark Zuckerberg or Elon Musk. Media worship of super-fast-growing companies — many of which are actually terrible, money-losing companies — fuels the fire. Reality TV and social media make it look like everyone can afford a $5,000-a-month studio apartment in San Francisco.

This narrative is out of whack. Your teenager may enjoy doing school plays, but you’d be irresponsible to urge her to move to Hollywood and try to become a movie star overnight.

If she is serious about acting, you might encourage her to audition for local roles (or head to a slightly larger city where there’s more opportunity), and build a reel and a reputation, which, hopefully, over time, would allow her to replace tips from waiting tables with paychecks from acting jobs.

Yet many entrepreneurs believe they can rush right to the top. Skip the fundamental work, and just scale, baby! One store is for losers; if you want to make it, you need 100 stores. This kind of thinking is poisonous. It sets entrepreneurs up to fail from day one. It’s like telling aspiring basketball players that all they need to practice are flashy dunks. Free throws? Dribbling with your left hand? Passing? Playing defense? Ha! Whatever! We know how that advice would turn out.

So, back to John. His ambition is good. And it’s good that he has a vision. But he would be much better off focusing all that energy on store number one, pouring everything into making it a destination people can’t ignore. Only then, once there is a line out the door, is it time to think about doing it again. One door at a time.


This article also appears in the July/August issue of Inc. Magazine.

Show me a business problem and I’ll do my best to avoid it


“One of the greatest ways to avoid trouble is to keep it simple. When you make it vastly complicated — and only a few high priests in each department can pretend to understand it — what you’re going to find all too often is that those high priests don’t really understand it at all…. The system often goes out of control.” -Charlie Munger

Many business problems are self-induced. Many wounds self-inflicted. The competition can win, but more often, the competitor loses to themselves.

Entrepreneurs are really good at making things hard on themselves. I talk with a lot of them and I see it everywhere. If they’d only put more energy into avoiding future problems rather than solving present ones they previously created, they’d make significantly more progress in less time.

We’ve built our business on avoiding problems. It’s the fundamental reason we’ve been able to do what we do, and keep doing it — profitably, and with a small team — for 18 years and running. Whenever we make big decisions, we make them in the context of future cost. Basically, how much will things suck later if we do this today?

We don’t see glory in tackling hard problems head on. We’d prefer to take the obvious way out and avoid predictable problems all together.

Here are some examples of things we avoid:

Avoiding growth

We’ve kept Basecamp intentionally small. We serve well over 100,000 paying customers, and a few million individual users, with a staff of just over 50. Small companies avoid big company problems. Less management is required, fewer layers necessary, less lost in translation, significantly fewer bottlenecks and formal processes that tend to keep people waiting around for permission to move forward with something. Everything’s more direct in smaller companies, and everyone’s closer to our customers, too. Surely some small companies can’t do what big companies can do, but we think that’s a very good thing.

Avoiding large teams

We keep our company intentionally small, and our teams intentionally smaller. Nearly every project we work on at Basecamp is done by a team of three people or less (two programmers, one designer). Many just two (one programmer, one designer), and more than a few with just one (a programmer or a designer). Could we take on bigger problems with bigger teams? Maybe — but we’d also be creating bigger problems with bigger teams. That’s not worth it to us. We’re happy doing many smaller projects with smaller teams. We can still accomplish whatever we want — just in smaller chunks. That allows us to more easily course correct along the way. And, frankly, that’s a better way to do things anyway.

Avoiding long time horizons

Few things are as demoralizing as a long-running project with no end in sight. While occasional infrastructure projects have unknown end dates, nearly everything we do fits into six week cycles, max (I’ve written about this in detail here). Many projects are intentionally small enough to take a few days or a couple weeks. So even if we end up putting 6 weeks into something, and we’re not thrilled with it in the end, all we’ve lost is 6 weeks. We avoid all the complications that come with pushing on when we know it’s probably not a good idea. Compare that with “too big to fail” or “it’s done when it’s ready” projects that take 6, 8, 12+ months… It’s highly unlikely you’ll walk away from all that work by the time it’s done. Long projects are morale graveyards.

Avoiding plans and promises

Similar to the point above, we rarely look beyond 6 weeks. We have some bigger picture ideas of where we want to go in a general sense, but those are held in our heads rarely written down. It’s unofficial oral tradition. We also rarely make promises about the future. Future promises are a huge source of headache and conflict. It’s easy to say yes about something down the road because it takes no work today. But when time comes due, you rarely want to be doing that thing you promised so long ago. Past promises are the genesis of so many problems in business. We avoid those kinds of promises like the plague. I’ve written more about this topic here.

Avoiding scale

Scale! Scale! Everyone wants to scale! WE DON’T! We try to avoid things that require scale to be successful. We look for things that work at any scale — small or large. For most companies, scaling is synonymous with “the economics don’t work now, but they will eventually”. Don’t get ahead of your skis — grow within your means. Be profitable as soon as possible with as few customers as possible, not with an imaginary many.

Avoiding dreadlines

We have deadlines. We avoid dreadlines. Dreadlines are deadlines that don’t give a fuck about you. They force you to sprint and rush, but they keep teasing you with a false finish line. They aren’t things you look forward to. What’s worse than not being able to see the end, is not believing the end when you see it. “They’ll just push it again”, “No way in hell will we be done in time…”. Attitudes turn negative, quality suffers, and people become more interested in just wrapping it up, than seeing it done well. The fun is gone when you’re constantly working behind schedule.

Avoiding miscommunication

Companies don’t have communication problems, they have miscommunication problems. Every additional person you add to a conversation exponentially increases the odds of miscommunication happening. Like Osmo Wiio says, communication usually fails, except by accident. Small companies and small teams inherently have a communication advantage over larger ones. Surely two people can misunderstand each other, but this is about playing the odds — small teams, small groups, small companies have far better odds of information traveling correctly than do their larger brethren.

Avoiding partnerships

Big companies come calling for us all the time. They want to set up partnerships. “We were wondering if you wanted to partner on something”… Huge red flag. Early on we followed these leads, and they always ended up in dead ends. Significant wasted time. This is especially true in imbalanced situations where a huge company wants to work with a small company. All things considered, it’s generally a huge amount of work for you (the small company), and a tiny amount of work for one of their many biz dev people who don’t have to do any of the implementation work itself. Avoid!

Avoiding bottlenecks

We avoid things that stop the flow of information and forward progress. We don’t set up management structures or policies that require permission. As long as what you’re about to do won’t destroy the company, just do it. Bottlenecks can take the form of people, process, paperwork, and permission. We’d much rather things run smoothly, than stop and verify at each step. Surely some things can go wrong this way, but few things do, and far more things just go right, frustration-free. Noah wrote more about this here.


This may be a weird metaphor, but I’m going for it anyway… It’s like cleaning the dishes as you go. If you eat and clean up immediately afterward, you never have to clean up later. You’ve avoided a hassle and extra work down the road. If you eat, and leave dirty dishes in a pile to be cleaned later, you’re actually creating a lot more work for yourself — or for someone else. Food dries, it’s caked on, it’s harder to scrub off. You’ve increased the difficulty level of the work that has to be done. Further, a pile is intimidating — piles often become bigger piles because no one wants to deal with them. What’s another dirty plate? I’ll just toss it on here. But if you clean as you go, it’s much faster, it’s part of eating (rather than separately cleaning), and you never have to return to the work later— it’s already done. The future is free and clear.

Don’t leave dirty dishes at work.


Bottlenecked? Is your team playing catch-up all day with unread emails and chats? Bouncing between too many things and unable to find time to focus on the work at hand? Stuff slipping through the cracks? Is the process that used to work starting to crumble? It’s time to graduate to Basecamp 3. It’s free to try — just visit basecamp.com and see what the alternative to “it’s crazy at work” looks like. It’s unlike everything you’ve ever tried before.