There are excellent and lousy versions of venture-backed and independent software companies. But differing priorities trend towards divergent paths in the long run.

Stay independent or plan an exit? The risks of selling out too early.

Don't sell your company before you've built it.

We’ve grown over the past ten years without taking a dime from investors.

Of course, that’s nothing special. Most businesses work that way.

That is unless we’re talking “startups.” Since the internet frontier opened in the 90s, there’s been a gold rush on staking claims in tech that might disrupt entire industries — even change the world.

As an internet company, most people assume Pathwright is investor-backed. But we chose a different path: independence. It isn’t for everyone or every kind of product. But a decade in, we’re happy with where it’s led us.

In 2011, Mark and I were busy building a beta version of Pathwright in a spare bedroom. It didn’t take long for “seed funding” to come up. Many thoughtful, qualified people pushed us to raise money or risk losing to more well-funded players in a hot edtech market. We received the first of many investment offers pre-launch and were cautiously curious.

But then, every conversation with an investor ended on the same note: our “exit strategy.” What timeline would we, the founders, be comfortable selling increasingly more shares to investors until we exit with a big payday?

Mark and I wanted creative freedom to create an innovative tool for teachers — Talking about exit plans felt like bringing up a prenup on a first date!

But an exit strategy is the entry point for a venture-backed company.

Of course, there are excellent and lousy versions of both kinds of companies. But differing priorities trend towards divergent paths in the long run:

Venture companies race to the exit (or else).

A venture company’s formula for success is to:

Sell shares of ownership to future investors at a profit.

A typical venture-backed startup is a financial instrument first, product second. Money doesn’t play a supporting role — money is the point.

Success means exiting with a sale to a larger company or the public as an IPO at a 100X return.

Of course, accomplishing that is no small feat: it takes talent, grit, and sheer luck to accomplish an almost impossible juggling act: competing in the market for a runaway product success while also competing for worthwhile investors’ buy-in.

It’s no wonder more than 9 out of 10 startups fail. Sadly, when they do, the exit strategy triggers a sell-off to the highest bidder or selling off the company for scrap to prevent potential further loss. Again, money is in the driver’s seat. It doesn’t matter how many people genuinely loved the product if the exit ROI targets aren’t looking good enough.

This intense pressure to stay on track (or else ) often evolves into filtering critical decisions through increasingly shorter-term ROI calculations as the investment runway runs out: Scrambling to hire a bunch of okay fits instead of waiting for great fits; Pump and dump sales techniques to hit the next quarter’s numbers and jack up the business valuation; Pivoting away from interesting, promising innovations that won’t move the dials soon enough.

Few manage to smoothly exit this treacherous highway — fewer still with souls intact. The best-case scenario for most is that the original owners exit owning a lot more money — but no longer owning the destiny of the company they poured so much into.

Independent companies grow at an organic pace.

The formula for making an independent company work is simpler — but challenging enough:

Starting from scratch forces independents to prioritize product value over everything else. And to keep doing it — there are no shortcuts or fallbacks.

Money plays a supporting role — it validates and fuels improvements to the product.

It means a smaller team, feature set, and promotional spend — smaller (and slower) everything.

But there’s a hidden benefit: a more natural pressure-to-growth ratio. In most of life, we grow in direct proportion to the tiny stressors we respond to: an extra rep, a thoughtful reply, a dollar saved — each increment yields a little more to build on later.

By necessity, independent companies make smaller, incremental bets in response to pressing customer needs. They don’t have the luxury of swinging for the fences or punting sustainable business models down the road. It’s a slower path — but more natural and satisfying in the long run.

And here’s the best part: As profit grows to fuel more possibilities, the company can reinvest it on its own terms and timeline. No outside investor need sign-off. And we get to keep building for as long as we’d like in the way we like.

For us, saying “no” to taking a venture-backed path ten years ago and many times since came to one question: do we value independence more than ROI?

We admire entrepreneurs who manage to create and sell multiple companies and generate a lot of money for many people — but that’s not us.

But independence gives us the flexibility to make daily decisions based on what we’re motivated to create. Only our customers can tell us if we’re on the right path (and better believe you do!). Best of all: we can keep building as long as we stay on the path — and we’re in it for the long haul.

(1) There are notable exceptions, of course. Apple is perhaps the most successful product company of all time and was funded with venture capital. Naturally, many investors (including those pitching us) often use them as an example. But it’s not quite an Apple to apples comparison: Apple had hard costs, rare talent acquisition, and other barriers to entry that most software startups don’t approach. They required investment and used it to fund innovation directly, not just to fund rapid expansion. Further, under Steve Jobs, Apple remained notoriously product first — investor second. Apple is a great case to consider, as long as we keep in mind that they’re an exception to many of the rules.

Why rebrand after a decade? I'll answer that in a moment. But first, let me rewind.

Why rebrand after a decade? I’ll answer that in a moment. But first, let me rewind.

I’ve worked on every version of Pathwright’s brand for the last 11 years. Even back when we were called Coursebook! In retrospect, updating our name to Pathwright in ’12 was the most clarifying brand change we’ve ever made.

But lately, I haven’t felt the clarity. So I’ve been drawing new logos for Pathwright for a couple years. But none of them stuck. We knew it was time to refresh, but I didn’t have the guiding star that tells you where and where not to go with. A brand needs a big idea.

I started chasing the next big idea in earnest late last year. ’21 was a special year. I got to see so many thoughtful and creative customers use Pathwright in delightful, wholly unexpected ways. They’d moved beyond our brand’s academic adventure tone to innovate within academia and far outside it. So I made it my goal for our brand to follow them. I think none of my previous sketches stuck because they were all about us—a mistake.

I adjusted to follow the universal thing we and every one of our customers have in common: Paths. Paths are the core of Pathwright. Making a path with Pathwright should turn a task, program, or topic into something as simple to use as a road in front of you. But, of course, the thrills don’t come just from making a path. Like a road, paths are meant to be travelled!

But what about the folks behind the paths? I set out to follow our customers. After all, they’re who we made up the word “pathwright” for. That silent “w” makes all the difference, as do the makers behind every path.

Then a funny thing happened on the page as I sketched. If I rounded the silent “w” in “Pathwright”, it looked an awful lot like a winding path.

With simple lines and half circles, I had a logo, one that let me emphasize what Pathwright is for and who it’s for at the same time.

People who make paths made them long before they picked up Pathwright. They’re the “who” at the center of Pathwright, not us. We think they deserve the best possible tools, which is what we hope we’re making with every update. Great tools don’t replace craftspeople; they multiply every ounce of their effort.

A logo needs a word and a color. After tossing out dozens of fonts that didn’t fit, I drew the word myself. I can’t even tell you how many different r’s and p’s I drew. Dozens, definitely. Making the type myself was the only way to match the angle and tone of the logo. After spending weeks on it, I can say: Don’t go this route unless you have to. But in this case, it seemed like the only way.

Then I added red. That’s a big change after eleven years of gold. Why red? A few reasons.

Red, black, and white remind me of Swiss Modern, the style of choice for saying more with less. Pathwright exists on the increasingly crowded, complex internet. We’re saying “simplify” about more and more challenges these days.

Red also makes me think of high performance, like a race car. If you’re looking for the best designed, most powerful tools for making paths, you’re looking for Pathwright.

Red could be a spark of understanding that grows into a flame when you have someone to show you the path. Red signals heat.

For us? Red helps us, a group who puts a lot more time into our work than into talking about it, use our outside voices. Important things are good to be loud about. Red is undeniably the best color for speaking up.

So why rebrand after a decade? Because we understand things better than we used to. And we see where you want to go—where you’re already going!—more clearly.

And we know the most important thing we can do is make a Pathwright that goes with you.

I've talked about my work a lot in this article. But nothing to come out of a team is a solo effort. Big thanks to Mark and Paul Johnson for helping me shape these ideas, and to Lindsay Ramler and her team who took my Figma files and made a real website out of them. In the end, it took our whole team.

If you'd like to design a course, we invite you to try out Pathwright for free.

You can also send questions, comments, or topic suggestions our way on Facebook, Twitter, or Instagram or email lydia@pathwright.com. We'd love to hear from you!

Experts are expected to be teachers (and vice versa). If we confuse these two equally important skills, we dramatically devalue what makes them particularly helpful.

Writer Joy Beth Smith tweeted about the demands of publishing her first book. As if publishing wasn’t challenging enough, she also must promote her book — a job requiring skills very different from writing. What should she charge for speaking engagements? How can she compress 60,000 finely-tuned words into a half hour speech?

Education as a field might suffer a similar confusion. Experts are expected to be teachers (and vice versa). If we confuse these two equally important skills, we dramatically devalue what makes them particularly helpful.

Put simply: Experts advance a discipline; teachers advance learners.

An expert focuses on mastering a discipline in order to advance it. By contrast, a teacher transfers disciplines to others. Teachers operate within their specific community of learners to help those learners attain mastery. Hopefully, their learners become experts.

Why do we confuse these roles? What's lost in the process?

Not too long ago, lecture circuits were like Netflix. Vast information bound up in books didn’t move easily. Unless you were wealthy enough to be literate or lucky enough to live near a library, you had little means to learn. Unless an expert came to town. On this rare occasion, you’d gather in a big hall and binge on lectures for hours.

If you were really lucky, you might be able to afford university — experts talking for hours and days on end. Then, you became the expert! You could lecture, too!

Repeat this process for hundreds of years. Congrats, you created our education system.

Eventually, digital circuits got pretty great at transferring information, too. This sadly hasn’t yet changed much about how we teach. Learners still sit through long lectures to get information or wade through millions of pages of Google search results that never seem to stick.

Somehow, we still require teachers to play experts, conveying the minutia of their fields in a few interminable minutes (regardless of the strain this puts on learners and teachers alike).

Earlier, I said teacher and expert are different roles. If we emphasize their superpowers, they start to work together.

Export their answers for other experts and teachers

Understand the lexicon and essential questions of their discipline

Engage their specific community of learners

Adapt essential resources for their communities

Invite learners along a path to new levels in their discipline

What strikes me is that these roles don’t compete — they complement. Scramble them together and you have long, dull lectures. But treat them as white and yolk in the same egg, and I think we’ll forge an alliance that finds answers and explains them for communities who need them.

The rare few will master both roles. But we might more often need to say, “Those are totally different skill sets!” If we create easy channels for experts to share their expertise and effective tools for teachers to bring that expertise to their communities, we’ll be in better shape. Teachers, experts, and learners alike will certainly be happier.

At Pathwright, we aim to equip both experts and teachers. That’s why we’ve made tools for both. Experts can now offer their curriculum for teachers in communities around the world. Teachers get power-packed courses complete with teaching tools that make helping their learners even easier. Here’s a short article from our guidance team on offering your course to multiple Groups. If you’d like to find out more about Pathwright, check out Intro to Pathwright.

How much of their limited attention can teachers give to learners? For a long time, we’ve operated as if only two choices exist. But I think there’s an Option Three.

Learner Attention vs Scale at Odds Then, Not Now

This post is an expansion of my own notes from working on our new About page. You can check that out for a quicker overview and cooler pictures.

Let’s say you have one bottle of Dasani. Just one. But on the table in front of you sit two dozen potted tomato plants, just beginning to bear fruit. What do you do?

Do you divide the water fairly between all twenty-four, even though each would get less than an ounce? Maybe give the water to just a few, so they actually grow? Drink the water yourself and learn to like tiny, green tomatoes?

Today we're looking at a problem parallel to this tomato teaser. How much of their limited attention can any teacher give their learners? For a long time, we’ve operated as if only two choices exist. Option One—limit learners to increase per capita attention—or Option Two—scale over everything. But I think there’s an Option Three.

For Option One, we flip to the front of the history book. Back in Aristotle’s time, the mid-300s BC, teachers work with very few learners. Aristotle teaches only a few aristocratic pupils at a time. Later, Jesus educates at a teacher-disciple ratio of 1:12 (excluding his TED Talk-like addresses). Da Vinci manages an even lower ratio—more like 1:7.

Let's start graphing. I know, I know, I'm excited too! But settle down, please.

We draw one axis for how many learners each educator teaches at once—"# PPL." Now we draw another for how much attention each teacher could afford per learner—"ATTENTION." Our apprenticeship examples in purple fall on the far right. Low number of people, high amount of attention.

Okay, we flip forward in history. Now we're in the 1700s and 1800s. This era marks the rise of what’s sometimes misleadingly called industrialized education. The teacher-learner ratio changes; we find Option Two.

In Europe and North America, smart folks like Horace Mann wonder how to make educated citizens out of their diverse, far-flung populations. They begin developing a concept we'll later call the "common school"—the seeds of our modern public education system. As education goes national, they discover a new appetite for scale. I’d like to think those early meetings must have sounded like start-up pitches—“But how will it scale?”

Education leaps from a few learners at a time to dozens at once.

We flip further to the back of the history book. Starting in the 1920s, radio helps audiences experience arts, education and entertainment as it happens. Everyone watches the 1969 Apollo 11 mission on TV. Fred Rogers uses his show to reach 1.8 million homes at its peak in 1986. Geography and history game “Where in the World is Carmen Sandiego?” sells more than 4 million copies by 1995. The learner masses grow to almost inconceivable scale.

Let's revisit our attention-to-people graph and add Option Two. A few blue dots for public school in the middle, a few at the far left for mass media.

When we draw a curve to connect all of our points so far, we get this:

It looks like Option One and Two combined to create a system that biases toward giant settings. Most learners represented on our graph would be in the head, with very few filling out the long tail. We can tell that teachers figured out how to give a few drops of attention to a lot of learners at once. Learners, on the other hand, don't receive much personal attention unless they're long-tail outliers. This system bias results in extreme efficiency but risks efficacy in the process.

Earlier, I dangled the possibility of Option Three. What would a third way look like?

At Pathwright, we've spent the last decade working to balance the curve with thoughtful, creative educators and organizations. We gave customer Krista King the features to personally tailor thousands of her individual learners’ paths just for them. Fellows programs like the C.S. Lewis Institute used Pathwright to scale their high-attention mentorship. They scaled to many new cities while helping supervisors give the timely attention their fellows need to explore through independent study.

Option Three uses a modern learning platform like Pathwright to share engaging learning with a personal touch. If we draw the curve our customers created, we get something very different:

This curve accounts for a few turnkey courses on the left tail. But it scales both attention and learner headcount nicely, for the first time. To compare, here’s the curve Option One-Two created, overlaid with our Option Three curve.

It seems to me that education has wound through the phases of a start-up over the last few millennia. It incubated in tribes and apprenticeship settings. It launched a compelling MVP in the 1700s and 1800s as education went to market at scale. But now it’s upgrade time.

I think education deserves to get out of beta, don’t you?

Both schools and organizations work better with clear paths and close connections. At Pathwright, we’ve seen giant institutions use well-designed paths with effective teachers to bring their scale down to each learner. So I'm certainly not suggesting closing schools. We’ve also seen two-person operations scale out to serve thousands. So apprenticeship isn't dead either.

We think you should be able to scale your attention with your learners—our amazing educators provide the proof. We’re not here to change the world (you’re doing that already). We’re working to give you the creative tools you need to keep doing it without having to choose between attention and scale ever again.

Give every plant the water it needs to grow.

Again, this post draws from my own notes as I worked on our new About page. All of these ideas wouldn't fit on that page. If you have a sec, check out our About page for a more fast-moving, visual overview of what we're here to do.

Coffee Walks is a new and ongoing interview show from the Pathwright team. Mark Johnson discusses the importance of side projects in his own life and the Pathwright team.

Coffee Walks is a new and ongoing interview show from the Pathwright team. We'll talk about technology and teaching through stories that connect them. In this episode, Mark Johnson discusses the importance of side projects in his own life and the Pathwright team. 

Host: Christian Shockley
Guest: Mark Johnson

More from Mark:

"How I Launched Six Side Projects in 2017" 

Have an idea for an interview topic? Send questions, comments, or topic suggestions our way on Facebook, Twitter, or Instagram or email christian@pathwright.com. We'd love to hear from you!

coffee_walks_1-_mark_johnson_on_side_projects.mp3

The first person to ever complete a Pathwright course was a retired gentleman in his 70s. He’d never even used a computer before. His granddaughter set him up with a laptop, internet connection, and a barely-working Pathwright account.

The first person to ever complete a Pathwright course was a retired gentleman in his 70s. He’d never even used a computer before. His granddaughter set him up with a laptop, internet connection, and a barely-working Pathwright account that he used to blaze through the course faster than all the other beta testers.

That was in 2011 when Pathwright was just two twins (Mark & me) hacking together in our spare bedroom and spare time. Our first goal was to design a course experience so simple anyone could do it. And this fine gentleman validated that we were on the right track. That felt great.

Back then, we wanted nothing more than to make a simple, beautiful product that teachers and learners alike would love. We spent the next five years bootstrapping Pathwright from a side project into a team of people serving thousands of educators.

But, after launching Pathwright 2 in 2016, I slumped into dissatisfaction with our product. It’s not that it wasn’t working. In fact, people loved the changes we’d made. But I’d begun to fall into the Silicon Valley trap of thinking that somehow our little software app needed to “change the world.”

Now we’ve never fit the mold of a Silicon Valley startup. We turned down venture capital in favor of bootstrapping and have always been profitable because we’ve had to be. We've always run Pathwright more like an ordinary business. That isn’t to say we’re not ambitious, but we're not motivated by truckloads of money or fame. We're more interested in making a dent in the world for good while we can.

Despite this, I’d drifted towards the stereotypical Silicon Valley siren call that our product might just change the entire world. But the reality is that most businesses — and especially software businesses — aren’t going to change the world. And that’s ok. Software is merely a tool, after all.

We’re not hoodie-wearing heroes, we’re the craftspeople and tool makers. Our role in the story is more like Ollivander, Harry Potter’s wand maker, Batman’s assistant, Alfred, and Don Quixote’s horse.

Let’s get over ourselves. Sure, viewing our trade as techsmiths isn’t as glamorous but it is fulfilling and noble.

Once we stopped navel-gazing at our product and put ourselves in our proper place, we had the clarity to formulate our true purpose. Here’s what we came up with:

Our mission is to multiply the impact teachers make on the world.

This simple mission frees us from struggling to play the hero and focuses us only on helping the people who truly make a difference in the world: Teachers.

If you’ve got something to teach, then you’re the hero of our story. And if our Pathwright can cut down your busywork so you have more time to teach and give you tools that help you teach more personally and reach more people, then we’re multiplying the impact you already have. And that’s what changes the world.

We couldn't get away from the feeling that we were running on a treadmill we had no way of switching off or even slowing down. Recovering a more natural rhythm of work and rest humans are wired for, here are five benefits of working in 6-week cycles that we can't do without.

During the summer after I graduated from college a sinking feeling began to creep up on me. While I'd readily said "goodbye" to school for good, now I was looking at a seemingly-endless expanse of time ahead of me with no new semesters, long breaks, advancements or graduations to look forward to... just work and whatever I made of it. I like work and making my own path through it, but something about this horizon of unstructured sameness unsettled me enough that I got very close to signing up for more school.

Over the following decade, I got used to the never-ending stretch of time, and we began to build Pathwright as a never-ending series of projects. (Software is never "done".) We'd start and finish projects and then pick up the next. We hit (and missed) plenty of launch dates in no particular rhythm. We tried out many project management tools and methods from kanban boards to project management software to sticky notes and saw marginal improvements.

In other words, we worked pretty much the same way as every other company. But no matter how hard we tried, we couldn't get away from the feeling that we were running on a treadmill that we couldn't switch off or slow down. As the product and team grew and projects stacked up, we ran into frequent periods of intense work and subsequent burnout. After a particularly rough stretch of time leading up to launching Pathwright 2, we knew we had to get off the treadmill. That's when we stumbled across this article about how Basecamp works in six week cycles. We've learned a lot from Basecamp over the years and had nothing to lose by giving this method a try in the new year of 2017.

Most new ideas we try on for size work to a degree, and we adapt them a bit for marginal overall improvement. But this idea was not like that: It worked immediately. It worked amazingly. And it's still working.

Now, it's hard for us to imagine not working in six-week cycles that we refer to as "Trails." In addition to recovering the more natural rhythm of work and rest we humans are wired for, here are five benefits we can't do without:

1. Time-boxing projects into six-weeks helps us plan smaller & smarter.

It's notoriously impossible to predict accurate timelines or costs for software projects (and that's true of any multifaceted, creative project). Humans are simply no good at predicting the future. Once we finally accepted our finite planning powers, we gained a tremendous amount of mental clarity and focus from simply limiting our time horizon for projects to "what can we realistically accomplish in just six weeks?"

As for how many projects we plan during one trail, we followed Basecamp's lead and commit to:

⛰ Expeditions: A few bigger projects that will take four to six weeks.

🏞 Hikes: Seven to ten smaller projects that take anywhere from a couple of days to a couple of weeks.

After the first few trails of taking on quite a bit too much, we added a "Notch Day" smack in the middle of the six weeks that acts as a checkpoint to review project progress, share feedback, and help each other edit down projects to even smaller sizes when we can.

2. We get to hit the reset button every six weeks.

While we try to keep projects within the six weeks, we don't stress out if we don't quite make it. Instead, we hit the "reset" button during the two weeks in-between trails.

We call these two in-between weeks 🏕 "Camp weeks" which are a break from focused projects to focus instead on review, exploration, and planning at a slower pace.

Any projects not finished in the previous trail are reframed and reshaped as a new project for the next trail or put on a waiting list for a future trail.

3. There's time to look back, think, and plan.

Our 🏕Camp Weeks in-between each Trail are a welcome respite. We take a slower pace, re-orient ourselves towards our goals and mission, and begin to map out the next six-weeks of work.

Camp weeks not only provide us with a nice break, but also help us zoom out from periods of detailed focus to reflect on our mission, strategy, and goals. This big picture review every six weeks helps us avoid the common pitfall of prioritizing the urgent over long term impact.

4. We have a rhyme and reason for saying "later."

Before we worked in trails, it was more difficult to tell team members and partners with a great idea or pressing need that we'd have to get to it "later." While later is necessary 93% of the time, it could come across as subjective and arbitrary when our only framework for planning was whatever we decided was next in line. Additionally, we spent a lot of time and energy attempting to synthesize all this new feedback with current plans as it came in (which was all the time).

Now that we work in Trails, we can simply share that we'll consider the idea during an upcoming Camp Week and get back with them — and then forget about it until then. While we still have to say "later" to most requests, at least there's a rhyme and reason behind it and our team and customers have all generally found knowing the rhythm of our work reassuring.

5. We get to share more of what we've accomplished.

🏕 Camp Weeks carve out enough time to share what we accomplished in the previous trail with our team and customers every seven weeks. We call this 👩🏼‍🏫 "Show & Tell" and it's become a something we look forward to. It's a bit like a mini-graduation we get to experience together six times a year. We're twelve trails in now, and I'm still amazed by how much our team accomplishes in just six weeks.

If you feel like you're running on a treadmill, experiencing bouts of "sprints" and burnout,  then  it's time for you to try something new as well. We unequivocally recommend giving some form of this work & rest rhythm a try and would love to hear how it works for you.

Let us know on Facebook, Twitter, or Instagram or email lydia@pathwright.com with thoughts, questions, or topic suggestions.

There are – and always will be – hundreds of features that we could build but haven't. If you’ve ever wondered about how we prioritize what to build, well…

Pathwright has many features already, and we launch new features or enhancements every 6 weeks. Even so, there are—and always will be—hundreds more features that we could build but haven't yet. 

If you’ve ever wondered about how we prioritize what to build, well . . . read on:

We love to hear suggestions for new features, so if you have one, please let us know. And just so you know what to expect, we'll respond in 1 of 3 ways:

1) That's on the roadmap. If your feature request is already on our roadmap, we'll confirm with two important qualifications: 

We usually can't confirm when a feature will be available (see "how we work").

Our roadmap is always subject to change (see "how we prioritize").

2) That's not on the roadmap. If we don't have plans to build it, we'll be up front about that.

3) That's an interesting suggestion! If we're not sure about it, we'll likely ask a few more questions and catalog the feature requests to consider later.

We work in 6-week cycles to complete 1-2 big features and a batch of smaller enhancements that are completable within 6 weeks.

We plan what to build next in between cycles. After each cycle, we have 2 planning weeks where we decide what roadmap features we’ll commit to for the next 6 weeks.

We pick which of the hundreds of features we could or should do at some point by . . . 

Selecting the highest impact features for all our educators that fit within our strategy and are within reach of our design and development resources during the next 6 weeks.

Prioritizing features that a partner funds and provides feedback and testing on when we can do so without impacting #1 significantly.

Running often is not a comfortable choice. Yet almost every day, I find myself hitting the trail for a run even though it’s much easier to do practically anything else.

How to use “creative endorphins” to foster a healthy habit of making

Running often is not a comfortable choice. Yet almost every day, I find myself hitting the trail for a run even though it’s much easier to do practically anything else. One reason I keep doing this is that I’m chasing that “runners high” (a.k.a. endorphins). I’m literally addicted to running. So if I don’t run for a few days, I start to feel mild withdrawal symptoms.

I find that this dynamic overlaps a lot with fostering creative habits. Great creative work can also be painful and time consuming, but that feeling of making something and putting it out there gives an endorphin-like kick to your brain. Once you’ve done it enough times, you’re hooked. It’s no longer nearly as appealing to spend most of your time on consumption activities when the lure of creating something new is right there.

Quick aside: I believe creative work is any effort that produces something new to increase efficiency in or enjoyment of life. That could be art, spreadsheets, code, etc…

So how do you foster this kind of creative addiction? It’s pretty similar to how you become a runner.

⏱ Put in the time. When it comes to learning new things or creating new habits, there simply is no shortcut for time invested. Don’t believe anyone who tells you otherwise (especially if they’re selling something). I don’t get my endorphin hit until mile eight of a run. Similarly, it takes some hours for creative work to give you that same satisfaction.

🚢 Ship it. It’s not done until it’s out there. This is tough for anyone with high standards, but you won’t get that endorphin hit until you do. To foster a healthy addiction to creating, you must ship frequently.

👟 Dress for success. One way I trick my lazy self into going out for a run is by putting on my running clothes well before I need to. Similarly, having a ritual and environment in which you create will allow you to “put on” the proper context for creating. This will help you commit to the hard work and long time blocks.

As a dad and teacher, I think a lot about how I can foster a habit of creating instead of consuming in my children and students. Scheduling blocks of open time, praising them when they “ship,” and creating a context that encourages creative work will help the next generation become creative addicts who just might change the world with what they make.

Whether you’re wrangling your team to reach a milestone this week or psyching yourself up to launch your course this month, you can ride the primo wave of a supportive process to get there.

You start your week with the best intentions. This is the one—you’re going to knock it out of the park this week. But by Friday, a dozen random tasks pulled your attention away from your goal. Exactly what your goal even was seems very, very hard to remember. 

In 5 simple steps, here’s what we’re trying at Pathwright right now:

1. Set your destination for the month, quarter, etc.

Project planning gets a lot simpler if you set your destination before embarking. If you’re not used to filling out a project brief, just try answering these three questions to set your destination:

How would you summarize the project in 2-3 sentences? Pretend you’re explaining the project to a coworker over coffee.

What potentially contentious or high-ambiguity questions surround the project? You’ll need to answer these with someone who’s qualified during planning.

What jobs to be done does this project solve for? If you’re new to JTBDs, here’s a great primer.   

The time frame is up to you. We work in six-week project cycles at Pathwright. After trying week-to-week and quarterly, six week chunks works perfectly for us. Your situation may vary, but I recommend not planning too far out.

Since you know your destination, what strategic goal for this week will take you there in time? If you’re planning to launch a new course by the end of the month, then maybe your goal for the first week sounds like “write a set of learning outcomes for my course.”

At Pathwright, we recently tried pushing ourselves to build a prototype the very first week. For a new feature, that meant developing an ugly but testable version. Prototypes shouldn’t look too nice, but they should uncover problems that were invisible before and would have derailed the project later. So maybe your goal for week one is “outline my course in Pathwright.”

For most of us, goals don’t work if we’re the only ones who know them. It’s too easy to downgrade my ambitions or reschedule the deadline. To prevent those outcomes, tell your team your destination and weekly goals.

Our company uses Slack and IFTTT for this. I set up these automatic questions to ping everyone…

At 9am on Mondays: “🏞 What's your goal for this week that'll help you reach your 6-week destination?”

At 9am on Tu/We/Th/Fr: “💪 What's your goal for today?”

At 3pm on Fridays: “🏁 How'd it go with your goal for this week?”

4. Be public about if you hit your goal this week.

Cheer with each other when you make it, and figure it out together when you don’t. Shame doesn’t belong here; you need to keep the process supportive, or it won’t work. Everyone misses goals sometimes for all kinds of reasons. Patterns of success are great to build on; patterns of failure are great for encouraging experimentation.

For missed goals, try asking these questions:

Was my goal specific and reasonable enough? It’s hard to hit a moving target, or a target that’s a football stadium away—try a tighter goal next week.

Did too many other things get in the way? I won’t always be able to, but I need to say “no” to things that get in the way of my goal—try saying “no” more next week.

Does weird stuff happen every week? Maybe I didn’t define the project enough before starting—try revisiting the brief.

Do I feel behind all the time? Maybe I don’t have as much open time for the work as I thought—try cutting scope.

Show your work from your weekly goal and tell your team a little about it. I’m surprised by how accessible work way outside my own discipline is—development project, sales initiatives, etc.—after a link and a few sentences of explanation. 

A quick screen recording of a new feature Robert worked on.

A Google Doc for a new process Paul spent the week developing.

A link to a beta version of a site Lindsay built.

So far, it seems like if we decide to show and tell about our work every week, anything can be show-and-tell’d. Again, we use Slack for this. It’s amazing to see a digest at the end of the week summarizing the cool things everyone worked on. I think you’ll be pleasantly surprised how amazing your own team is when you share your work every week.

That’s it! These 5 steps keep our teams on track at Pathwright. We’d love to hear if it works for you and what you’re trying on Facebook, Twitter, or Instagram.

If you’re tired of not being sure your people are learning what they need to, try Pathwright. We built it from the ground up for ultimate clarity—from powerful outlining to seeing actual faces move from one step to the next. Get started free.

How to reach your weekly goals with your team or for your online courses.

The first days of class are what I remember best from my time teaching. Covering syllabi, mispronouncing names on the roll, trying to wrap up early to build goodwill with my students.

The first days of class are what I remember best from my time teaching. Covering syllabi, mispronouncing names on the roll, trying to wrap up early to build goodwill with my students. I rarely knew any of them yet.

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