Brian Gilham

Engineering leader, husband, and father

monday-mailer

What's Your Criteria?

I often hear from readers who have a list of side project ideas a mile long but struggle when it comes time to pick one. It’s easy for some — they just pick one and get on with it. But others, faced with seemingly endless choices, freeze up and start to procrastinate. Previously, I’ve written about why it’s important for you to have a North Star; something to remind you why you started working on side projects in the first place.

I often hear from readers who have a list of side project ideas a mile long but struggle when it comes time to pick one. It’s easy for some — they just pick one and get on with it. But others, faced with seemingly endless choices, freeze up and start to procrastinate.

Previously, I’ve written about why it’s important for you to have a North Star; something to remind you why you started working on side projects in the first place. But, when it comes to deciding which project idea to work on, it’s equally important to know what your criteria are for a worthwhile, valuable side project. If you don’t know — on a personal level — what constitutes a good project, you’ll waste time jumping from one project to the next hoping to find something that sticks.

I work on side projects to keep my skills sharp, share knowledge with other people, and build an audience for my writing. I keep an extensive list of project ideas in Evernote. When I evaluate which project to take on next, I consider each idea on my list and ask three questions:

  1. Would this idea involve skills I want to maintain or improve? Lately, this means new projects have to involve a fair bit of writing.
  2. Is this idea something other people would find valuable or interesting? It’s fine to scratch your own itch, but I find it far more satisfying to provide value to someone else.
  3. Assuming it’s successful, is this idea something I can iterate on and improve? I love to update, reuse, and build on work I’ve done in the past. I repurposed old articles for my email course, for example.

Before I even begin to consider working on something new, it has to meet at least two of my criteria. Preferably all three — the more, the merrier.

Have you considered what your criteria for good side projects might be? If you often find yourself struggling to decide what to work on next, take some time today and figure it out. There’s a good chance you’ve thought about them before, if only subconsciously. Write them down and keep them handy.

Next time you’re staring at your list of project ideas, frozen, pull out your side project criteria. Use them to test the viability of each and every concept, cutting bad ideas as you go. If nothing else, you’ll reduce the cognitive load of making your decision.

What’s your criteria for a good side project? Hit reply and let me know!

Until next time,

-Brian


Start Paddling

I’ve launched a lot of side projects over the course of my career, but I still get nervous each and every time — especially when I’m trying something for the first time, like selling an icon set or an Apple TV app. A laundry list of doubts creeps into my brain. What if nobody likes it? What if there’s a bug I haven’t found? What if it turns out I’m not all that good at this programming thing?

I’ve launched a lot of side projects over the course of my career, but I still get nervous each and every time — especially when I’m trying something for the first time, like selling an icon set or an Apple TV app. A laundry list of doubts creeps into my brain.

What if nobody likes it?

What if there’s a bug I haven’t found?

What if it turns out I’m not all that good at this programming thing?

My hand hovers over the keyboard. I could walk away without risking anything, I tell myself.

And then I launch it anyway.

It isn’t because I’m brave, or free of fear. It’s because, over the years, I’ve learned pushing through my fears is the only way to learn and grow. 

You can plan all you want. You can fiddle with a landing page design until your eyes bleed. You can hem and haw, and worry how your side project will be received. But, in the end, you only make progress when you look over the edge of the cliff and jump. You’re never going to feel ready.

It’s easy to sit around forever, waiting for the moment you feel prepared to dive into something new. But that moment is never going to come. You always could have worked more, tested more, practiced more. There’s always something more you could have done. But, at some point, you have to launch the damn thing.

I often think about the first time I went whitewater rafting. One of the first things they teach you is you don’t sit in the raft; you sit on the edge of it, right next to the rushing water. I won’t lie; it scared the crap out of me. I constantly felt off-balance, and I was sure I’d end up in the drink at any moment.

But here’s the secret: the only way to keep your balance is to paddle. It’s only by putting your oar in the water and getting to work that you’ll stay in the boat. If you wait until you feel stable, you’ll be waiting a long time. Because it never feels stable. 

Unless you have a crystal ball — and let’s talk, if you do — you’ll never be able to look into the future. Accept that you’ll make mistakes and be criticized, no matter what you do. Pick a direction and get moving.

Perfection is something you can strive for, but you’ll never reach it. Launching something imperfect can feel risky, to be certain. But I think it’s a far bigger risk never to launch it at all.

Until next time,

-Brian


One Foot in Front of the Other

Many people think there’s a secret formula for attracting an audience online. I hear from developers weekly who figure there’s some hack they haven’t discovered yet; a trick for making people care about their projects, apps, or blog posts. If you fall into that camp, I have some good news. There is a simple way to grow your audience. But it’s far from easy. To build an audience for your work, you “simply” need to produce quality work and consistently share it with the world.

Many people think there’s a secret formula for attracting an audience online. I hear from developers weekly who figure there’s some hack they haven’t discovered yet; a trick for making people care about their projects, apps, or blog posts. If you fall into that camp, I have some good news. There is a simple way to grow your audience. But it’s far from easy.

To build an audience for your work, you “simply” need to produce quality work and consistently share it with the world. That’s it.

But many developers, faced with a launch that failed to garner the attention it deserved, decide to give up. Worse, some walk away without finishing anything. Their hard drives are full of half-finished apps, book drafts, or designs. They get so close to the point where, with a bit more effort, they could have created something impactful.

In both cases, developers encounter resistance and think it means they’re on the wrong path. In The War of Art, Steven Pressfield says:

“Rule of thumb: The more important a call or action is to our soul’s evolution, the Resistance we will feel toward pursuing it.”

Translation: The things we feel the most resistance toward doing are the very things we most need to do.

You will encounter failure, in the course of your career. Some of the greatest makers on Earth have experienced failure, many times over. Steven Spielberg was rejected from theater school on three separate occasions. Walt Disney got fired once, due to a “lack of imagination.”

People with real passion, who care deeply about their craft, refuse to be dissuaded by failure. Instead, they lick their wounds, get up out of the dirt, and try again. And again. And again. They show up, ready to do the work. Each and every day.

The only way to find your version of success is to keep producing work. Your career isn’t a single moment in time; it’s a collection of moments. Some moments bring failure; others will take you to heights you didn’t think possible. You have to go along for the ride, either way.

Lots of people like to talk a big game. They boast about the things they’re going to accomplish, the moves they’re going to make. Usually, they make these proclamations while everyone in the room rolls their eyes. It’s obvious they’re all talk and no action. You needn’t join their ranks.

The fact that most people give up so quickly is the reason you can be successful — if you’re willing to stick around longer than they do. Sharing your work with other people is scary. Trying new things is scary. Being vulnerable on a regular basis is downright frightening. But that’s how you’ll stand out — by doing the things that scare others away.

You can push through resistance to create something great. But you need to make a conscious decision to fight on a daily basis; to have the grit to keep showing up — each and every day.

Start today.

Until next time,

-Brian


Finish Your Damn Side Project: Update #1

Last week I announced Finish Your Damn Side Project, a new book I’m self-publishing this summer. The reaction has been nothing short of amazing. I knew people were struggling with shipping their side projects — it’s part of the reason I write the Monday Mailer — but it’s obvious developers are hungry for a resource that goes deeper than a weekly newsletter. I’ve wrapped up planning and outlining the book, so I thought it would be a good time to pause and share what’s happened so far.

Last week I announced Finish Your Damn Side Project, a new book I’m self-publishing this summer. The reaction has been nothing short of amazing. I knew people were struggling with shipping their side projects — it’s part of the reason I write the Monday Mailer — but it’s obvious developers are hungry for a resource that goes deeper than a weekly newsletter.

I’ve wrapped up planning and outlining the book, so I thought it would be a good time to pause and share what’s happened so far.

Research

I’ve wanted to write a book for a long time. But I don’t want to write one just for the sake of writing it. Over the last eight months, I’ve had the opportunity to chat one-on-one with many of the 1,200+ people subscribed to the Monday Mailer. Like me, they see the potential for side projects to improve a developer’s skills and level up their career. But, when I ask about the challenges they’re facing, I hear the same issues over and over again:

  • “I don’t have time.”
  • “I’m feeling burnt out.”
  • “I don’t know how to get motivated.”
  • “I have trouble coming up with ideas.”
  • “I’m not sure how to get started.”
  • “I have trouble maintaining focus.”
  • “I keep procrastinating.”
  • “I think too much, instead of taking action.”
  • “I don’t know how to build an audience.”
  • “I’m not sure how to promote my work.”

I see the same concerns pop up in my conversations with other developers, and on sites like Reddit, Hacker News, Designer News, and more. I don’t claim to be an expert when it comes to this stuff. But I’ve managed to consistently ship side projects, throughout my career, while working full-time. I’ve learned some useful techniques along the way, and I think I can help.

Brainstorming

Once I decided to pursue writing the book, I sat down and started brainstorming potential topics. I opened a new document in Ulysses and added a new bullet point for every idea that popped into my head. No editing, no critique. Just opening the flood gates and letting ideas pour out.

I initially tried to do this in MindNode, but quickly realized it wasn’t the right tool for the job. Using MindNode, I felt tempted to try and organize my ideas prematurely. I don’t know about you but, for me, nothing puts the brakes on brainstorming faster than trying to generate ideas and organize them simultaneously.

This process produced somewhere in the neighborhood of 80 different ideas for topics.

Outlining

I knew I didn’t want to start writing until I had some idea of the overall structure. So, I wrote every possible topic down on a Post-It Note and stuck them to the wall.

It looks like pure madness, I know. But it was a fantastic way to see the big picture and start organizing my ideas into distinct sections. Patterns began to emerge, and I knew, if I couldn’t find a section to slot a topic into, I needed to consider cutting it. In the end, I managed to lose 10–15 bad ideas this way.

Getting Organized

My next step was to fire up Trello and create a new board. On it, I created 12 new columns:

  1. Topics
  2. Outlining
  3. Outline
  4. Writing First Draft
  5. First Draft
  6. Writing Second Draft
  7. Second Draft
  8. Writing Third Draft
  9. Third Draft
  10. Being Edited
  11. Edited
  12. Done

I filled the “Topics” column with a card for every topic that made the cut during the outlining step. As I work, I move each card along the conveyor belt of columns. It might seem like a lot of steps, but it means I’ll never lose track of my progress or what I need to do next.

Writing

On Friday, I started writing in earnest. My goal is to write at least 500 words per day. I’ve already completed a 2,000-word first draft for one of the essays. I know the importance of maintaining a daily habit when it comes to side projects. So, I’ll be working hard to try and stick to my daily word count.


Learning to Communicate

When you work with someone else, even someone you like, it can sometimes feel like you’re speaking two different languages. There’s a disconnect happening; you’re on separate wavelengths. You might agree on the goal you’re trying to accomplish, but be at odds on how to get there. It isn’t anyone’s fault, necessarily. You’re both skilled, hardworking people. You’re just approaching your work, and the world, from completely different mindsets. Sometimes the person you’re struggling to communicate with is your boss, compounding the problem.

When you work with someone else, even someone you like, it can sometimes feel like you’re speaking two different languages. There’s a disconnect happening; you’re on separate wavelengths. You might agree on the goal you’re trying to accomplish, but be at odds on how to get there. It isn’t anyone’s fault, necessarily. You’re both skilled, hardworking people. You’re just approaching your work, and the world, from completely different mindsets. Sometimes the person you’re struggling to communicate with is your boss, compounding the problem.

You can try to hash it out as long as you like; one of you will always leave the conversation more frustrated than when it started. When that happens, you need to accept that your usual approach to conversations just isn’t going to work.

I’ve been reading about this topic a lot lately. It’s opened my eyes to how different thinking and communication styles can be from one person to the next. Frustratingly, it’s often contextual. You get along fine one day and struggle the next. You just get sidetracked, somehow.

When communication starts to break down, it’s helpful to focus on listening intently and empathizing with the other person — a skill I’m constantly working on. As I’ve been reading, I’ve learned that people primarily fall into one of two ways of approaching life & problem solving: compartmentalization or connection.

People who compartmentalize are skilled at assigning the disparate parts of their life into different mental boxes. They have one box for work, another for their relationship, and another for their hobby or side project. These folks can jump from one box to another, but they’re always occupying one box at a time. This is the style I most identify with. If you start talking to me about a project at work, my brain jumps into that box. Want to talk about something else? Give me a second, my brain has to move to that box.

The ability to compartmentalize is important for a programmer. You need to consider how different parts of your code interact, sure. But you spend a lot of time working through one component at a time. Heck, they teach it in school. I tend to jump into one box, solve any problems I find, and move on to the next. As I’ve gotten older and more experienced, my ability to jump between boxes — and notice connections between them — has improved. But I’m still at my most comfortable when I can settle into one until I feel like I’m done.

On the other side of the spectrum — and it is a spectrum — there are people who primarily approach life by identifying and thinking about the connections between different issues. For these folks, life is full of connections just waiting to be explored. They see how one issue affects another. And another. And another. They’re naturally skilled multitaskers, rapidly jumping from one topic of conversation to another. They’re still solving problems, but they take a different approach. In exploring connections, they find the bigger picture.

“Compartmentalizers” feel overwhelmed, unable to jump between boxes quickly enough to keep up. “Connectors” get frustrated, unable to understand why others don’t see the connections they do. Neither style is right or wrong. Different situations call for different skill sets and approaches. You can even find one person embodying both styles, at times. I often switch from one to the other — though I struggle to do so in every aspect of my life.

Next time you’re struggling, at a fundamental level, to communicate with someone else, try to think about how their brain is working in that moment. Are they trying to focus on just one problem and solve it? Are they bounding from one thing to another, trying to grasp the bigger picture?

Thankfully, both situations can be improved with the same approach: working to understand where the other person is coming from.

If you’re working with someone who leans toward compartmentalization, take a breath and recognize their need to focus on a single topic for a while. You’re going to want to take the conversation in 100 different directions. Resist the urge. Once you’ve worked through the topic at hand, you’ll find a more receptive audience for your next thought. 

If you’re talking to someone who works by exploring connections, you might feel overwhelmed with information. That’s okay. Realize that talking through those connections is how they’re going to process their thoughts. Go along for the ride, with patience and understanding. Eventually, they’ll reach a point where things start to feel actionable.

Dealing with different personalities in the workplace — andlife, really — can be challenging. But programming is a team sport, much of the time. You can certainly try to put your head in the sand and hide at your desk. But you’ll advance more quickly — and learn more — if you take the time to improve how you interact with other people.

Until next time,

-Brian


I’m Writing a Book

For a few years now, I’ve had a secret goal: write a book. I’ve always admired people like Wes Bos, Jarrod Drysdale, and Nathan Barry — folks who teach what they know, write, edit, record, and sell their work. Developers, designers, writers, and countless others are in a unique position; they have the means to both create and share, or sell, the things they create. I’ve successfully sold products in the past — everything from an icon set to iOS & tvOS apps — but the idea of self-publishing a book has never gone away.

For a few years now, I’ve had a secret goal: write a book. I’ve always admired people like Wes Bos, Jarrod Drysdale, and Nathan Barry — folks who teach what they know, write, edit, record, and sell their work. Developers, designers, writers, and countless others are in a unique position; they have the means to both create and share, or sell, the things they create. I’ve successfully sold products in the past — everything from an icon set to iOS & tvOS apps — but the idea of self-publishing a book has never gone away.

I’m tired of just thinking about it. I’ve decided that 2017 is the year I’m finally going to do it. I sat down a few weeks ago and started outlining. Today, I’m ready to commit publicly.

My book, Finish Your Damn Side Project, will be available this summer.

Over the course of my career, I’ve become skilled at brainstorming, developing, and shipping side projects. In the last few years I’ve released more than ten apps, written countless blog posts & articles, and spoken at events & meetups on a variety of topics — all while holding down a full-time job that I love. Through it all, I’ve learned habits, concepts, tips, and techniques that I — and many other developers — have used to ship side projects consistently.

I share a lot of that advice & research with the Monday Mailer, my weekly newsletter. But feedback from subscribers, along with my research, shows many developers are hungry for more. I don’t claim to be an expert; I’m just a developer who has seen the power of side projects to improve your skills and level up your career. I think I can help.

I won’t lie; I’m a bit nervous. The book will be the first time I’ve taken on a writing project of this size. But I learned a long time ago that it’s important to start new, scary things before you feel like you’re ready. Because you’re never going to feel truly ready.

I honestly believe you don’t need someone else’s permission to share your passion, build an audience, and publish your work. The Monday Mailer is one part of that philosophy, for me. Finish Your Damn Side Project will be another.

Even if it doesn’t go as well as I hope, I’ll still learn a lot along the way. And isn’t that one of the biggest benefits of working on a side project?

In the weeks and months to come, I’ll be sharing regular updates — both in the newsletter and here on Medium. In my next update, I’ll share some of the steps I’ve taken to plan & outline the book, along with how I’m approaching the first draft. Want to stay in the loop and get a discount when the book launches? Sign up for the Monday Mailer.


It's Okay to Quit, Sometimes

When I started learning Swift, I hated it. I’d been programming in Objective-C for six years, and Swift felt unfamiliar and unforgiving. I can’t remember how many times I must have cursed out loud working with optionals or custom initializers the first few times. But I stuck with it and, eventually, things started to get better. Now I write everything in Swift and love it. If I’d given up at the first sign of trouble, I wouldn’t have picked up a valuable new skill.

When I started learning Swift, I hated it. I’d been programming in Objective-C for six years, and Swift felt unfamiliar and unforgiving. I can’t remember how many times I must have cursed out loud working with optionals or custom initializers the first few times. But I stuck with it and, eventually, things started to get better. Now I write everything in Swift and love it. If I’d given up at the first sign of trouble, I wouldn’t have picked up a valuable new skill.

When a side project makes you uncomfortable or frustrated, it’s often worth it to push through the discomfort. If you aren’t willing to deal with those early frustrations, you’ll never grow as a developer. Only quitters quit, right?

Except, there are times when leaving a side project behind is the right move. You have to know when it’s time to hang up your saddle and move on. I tend to step away from a side project when I started to feel like I’m overextending myself; taking on too many commitments at once. If you’re always working at 100% capacity, you won’t have any room left for new opportunities that may pop up. Not to mention, you’ll eventually burn out completely. So, I try to leave myself some margin — mentally, physically, and emotionally — to take on something new.

As a society, we equate quitting with failure. If we quit something, we worry people will see us as weak; that we couldn’t “hack it.” But the truth is, most people don’t care. You don’t earn extra credit for slogging through a side project you hate. If it leaves you feeling frustrated, depressed, or angry, you need to ask yourself why. Are you just have a bad week, or is there something deeper going on?

Quitting a project, particularly after spending a lot of time and energy on it, is hard. It’s so intensely personal. You’re the one doing all the work and making all the decisions. It feels like you’re letting yourself down. But you can’t let yourself fall prey to sunk cost bias.

Let’s say you and your partner decide to head to the movies for date night. You pay for the tickets & popcorn and settle into your seats, ready to be entertained. But you quickly realize the film sucks. Your first instinct might be to stick it out. You’ve already paid for the tickets and snacks, after all. If you leave you’ll have wasted all that time and money, right? Except, deep down, you know that isn’t true. The money is long gone, whether you like it or not. You might as well salvage what’s left of your evening and play mini-putt or something. There’s nothing to be gained from sitting through a terrible movie. 

The same idea applies to our side projects.

A good side project should bring you joy. It should be something you can’t wait to work on, full of interesting problems to solve. It should teach you a new skill, or expose you to new people. But if you’ve been working on it for a while and aren’t getting anything out of it — except frustration — it might be time to quit. In many ways, it comes down to prioritization. Is finishing your side project more important than other activities you could be doing instead? If not, it’s time to throw in the towel.

Here are a few questions to ask yourself:

  1. Have you been making measurable progress on your side project?
  2. Is your side project teaching you something new?
  3. Is the process of working on your side project still enjoyable?
  4. Does the idea of working on your side project leave you feeling depressed?
  5. If you finish your side project, will you feel good about how much it cost — in terms of time, money, or energy?

There are times we need to grit our teeth and fight through a bad situation. But if your side project, a commitment you’ve willingly chosen for yourself, is the thing bringing you grief, it’s time to quit. Free up your time for a project that will improve your skills, help you grow, and — most important of all — make you happy.

Until next time,

-Brian


Pay Attention

Many developers recognize the value of working on a side project but struggle to come up with an idea for one. It’s easy to look at people pumping out project after project, like Mubashar Iqbal, and think they have some gift. While some certainly have an innate talent, most have cultivated two critical skills; taking notice and being curious. Ideas are everywhere if you’re willing to pay attention. In your daily life, what’s something that annoys the heck out of you?

Many developers recognize the value of working on a side project but struggle to come up with an idea for one. It’s easy to look at people pumping out project after project, like Mubashar Iqbal, and think they have some gift. While some certainly have an innate talent, most have cultivated two critical skills; taking notice and being curious.

Ideas are everywhere if you’re willing to pay attention. In your daily life, what’s something that annoys the heck out of you? Maybe it’s your awful commute, a frustrating search for lunch, or poorly-designed software you’re forced to use. Start there. It’s a cliché, but it’s true; the best projects are born from scratching your own itch.

But you needn’t focus solely on yourself. Get outside the tech bubble and learn about the struggles of others. Can you create an app to improve the experience of taking transit in your city? What if your elderly neighbours could automatically receive a reminder about trash day on your street? Don’t worry about coming up with something groundbreaking or original. Build something useful for other people. Technology can improve almost everything we encounter, in some way.

Cultivate friendships and hobbies outside your usual circles. Strike up a conversation with the cashier at your grocery store. Chat up your cab driver. People will often share ideas without realizing it if you listen to them, instead of just waiting for your turn to speak. When you do open your mouth, ask questions. What are their aspirations? What challenges do they face at work? How does technology help or hinder them? Think about how you can apply your skill set to problems in a different space.

Carry a notebook with you, or start a new list on your phone. Every time you have even an inkling of an idea, write it down. Cultivate a curiosity about the people, places, and processes around you and, with a bit of persistence, that list will be full in no time.

Until next time,

-Brian


Monday Mailer Survey 2016

Two weeks ago, I wrote to the Monday Mailer and asked if my readers would do me a favour and fill out a quick survey. People spend so much time and energy trying to figure out what their audience wants — I figured I’d just ask them. 130 people were kind enough to take 6 minutes (on average!) out of their busy schedules and fill it out. Their answers will help me create great content for the newsletter & podcast in the year to come.

Two weeks ago, I wrote to the Monday Mailer and asked if my readers would do me a favour and fill out a quick survey. People spend so much time and energy trying to figure out what their audience wants — I figured I’d just ask them. 130 people were kind enough to take 6 minutes (on average!) out of their busy schedules and fill it out. Their answers will help me create great content for the newsletter & podcast in the year to come.

I thought it would be interesting to share some of the results.

Job Titles

84% of respondents identified as a software developer. Of those who didn’t, the most popular job titles were variations on:

  • Product Manager
  • Student
  • Teacher
  • Writer
  • Soldier

Side Projects

68% are working on a side project of some kind, with 58% planning to monetize it. 8% of those who responded have already monetized a side project.

When I asked the other 32% what was holding them back from working on a side project, they said:

  • A lack of time/too busy
  • Not having any ideas
  • No motivation
  • Feeling burnt out
  • Having trouble deciding what to work on

Challenges

Asked what the biggest challenge they were facing in their work was, most people said:

  • Time management/balancing goals & timelines
  • Maintaining motivation
  • Producing good work consistently
  • Staying focused
  • Suffering from imposter syndrome

Learning

Most respondents want to learn more about:

  • Marketing & building an audience
  • Team management & leadership
  • Monetizing their work
  • Learning design skills
  • Improving their time management skills

Elsewhere

When asked about other sites, authors, and podcasts they liked, the most popular answers were:


A Punch to the Gut

I fucked up pretty badly a few weeks back. The particulars don’t matter. I wouldn’t be able to share them, even if they did. But it was a big one; the kind of mistake that hits you like a freight train. People were hurt and angry — and rightfully so. It felt like I’d been punched in the stomach — the air rushed out of my lungs, leaving me speechless. I’m usually pretty good at picking myself up, dusting myself off, and moving on after I screw up.

I fucked up pretty badly a few weeks back.

The particulars don’t matter. I wouldn’t be able to share them, even if they did. But it was a big one; the kind of mistake that hits you like a freight train. People were hurt and angry — and rightfully so. It felt like I’d been punched in the stomach — the air rushed out of my lungs, leaving me speechless. I’m usually pretty good at picking myself up, dusting myself off, and moving on after I screw up. Not this time.

I spent the next day moping around, feeling sorry for myself. I wanted to run away; to get as far as possible from the person I saw in the mirror. That jerk.

But, on the second day, I remembered: This wasn’t the first time I’d screwed up in my life, and it certainly wouldn’t be the last. The fact that I’d made a mistake was important — I’d had a negative impact on other people. But how I responded to it would matter more, in the long run. I decided to focus on the people I’d affected, instead of my ego, and get to work fixing the situation. Time will tell if I’m successful or not.

On the internet, behind screens and keyboards, it’s easy to look at other people and imagine they’re perfect. All you see is their successes — the highlight reel. Fantastic vacation shots on Instagram. Tweets about crushing it on their latest project. And yes, newsletter articles about productivity. We all do it — selectively sharing things that present us in the best light possible.

But we’re all just regular people, trying our best to make today a little bit better than yesterday. And when you put yourself out into the world and try new things, you’re bound to screw up once in a while. Sometimes it will be minor. Other times, you’ll fuck up so bad you won’t even know who you are, for a bit.

In those moments, remember you aren’t alone.

Until next time,

-Brian


How to Start Writing

Writing and publishing the Monday Mailer has been one of the most positive experiences I’ve ever had online. It’s allowed me to share my work, improve my writing, and connect with people all over the world. I often hear from folks who want to start writing on a regular basis but don’t know where to begin. It’s easy to look at individuals who write and publish new articles multiple times a week, like Seth Godin, and feel intimidated.

Writing and publishing the Monday Mailer has been one of the most positive experiences I’ve ever had online. It’s allowed me to share my work, improve my writing, and connect with people all over the world. I often hear from folks who want to start writing on a regular basis but don’t know where to begin.

It’s easy to look at individuals who write and publish new articles multiple times a week, like Seth Godin, and feel intimidated. But it’s important to remember that everyone, from world-class authors to niche bloggers, starts at the same place: zero.

Zero writing skills. Zero online presence. Zero audience. Zip. Zilch.

If those people can improve their skills, publish on a regular basis, and build an audience, so can you. It all comes down to consistent, daily practice. Putting your butt in the chair and doing the work. Start by setting a target; maybe 250-500 words a day. Every day. No matter what

In the beginning, write without worrying about proper spelling, punctuation, or grammar. Don’t get hung up on that stuff. It’s far more important to focus on creating a new habit; on making words happen with some regularity. What you write might suck, at first. That’s perfectly normal, and should be expected. You’ll want to throw it all away, but I encourage you to resist the urge. One day you’ll look back at those early pieces and marvel at how much you’ve improved.

Write about your life, your challenges, or something you’ve learned recently. Write about the weird thing your dog did this morning. Write about your relationships, or your career. Whatever pops into your head. Try to be vulnerable and honest. Everything under the sun has been written about before, but no one can replicate your experiences and what they’ve brought to your life. You have a unique angle on just about everything – express it!

With time and a bit of dedicated practice, you’ll be cranking words out in no time. That’s what I love about writing. You may not be the next Stephen King or have formal training, but you don’t need it. You don’t need to wait until someone else proclaims you a “Writer.”

As long as you’re writing, you’re a writer. So, get to work.

Until next time,

–Brian


Focus on Your Strengths

Follow Up Last week, I asked for your suggestions for reducing the activation energy for your work. Here’s a few of the replies: ”One technique I’ve found useful is chaining. This article covers it and some other useful things pretty well.” —Steven ”One I use is telling myself I can stop after 5 minutes, since the hardest part is starting. That usually works, and I end up having to pull myself away from the task later after doing it for an hour or two.

Follow Up

Last week, I asked for your suggestions for reducing the activation energy for your work. Here’s a few of the replies:

”One technique I’ve found useful is chaining. This article covers it and some other useful things pretty well.” —Steven

”One I use is telling myself I can stop after 5 minutes, since the hardest part is starting. That usually works, and I end up having to pull myself away from the task later after doing it for an hour or two.” —Matt

”I found out that for me it is really important to be frequently doing something that I like. In my case it can some exercise (mainly running, martial arts and/or some dynamic fitness program, like crossfit), playing guitar, watching movies, doing zazen (buddhist sitting meditation, although this one can be really difficult most of the time), etc… Finding some balance in between leisure and work, for me, is really important, even when I’m working on something that I love.” —Liordino

Thank you to everyone who took the time to share their suggestions!  


I recently got an email from a reader who was feeling a bit stuck. She was in the process of launching her lettering business but was held up trying to finish her website redesign. She had the skills to code it herself, but the idea of doing it wasn’t appealing at all. So, she kept putting it off. She wanted to focus on one her strengths: lettering. But she couldn’t get past one of her weaknesses: coding.

I talk a lot about pushing through those “stuck” moments and beating procrastination. But I’ll you what I told her: focusing on your weaknesses too much is the wrong move, too. She could have spent 10 minutes making a landing page with Squarespace and gotten back to what she really cared about: her lettering projects. In the end, she traded some lettering work for a friend’s coding skills and launched a simplified version of the site. And it looks great.

As a society, we spend way too much time worrying about the things we struggle at. It leaves a lot of people feeling unhappy, unfulfilled, and stuck. What if we spent time figuring out our strengths and focused on them, instead?

We all have limited time, money, and energy. Slightly improving one of your weaknesses doesn’t strike me as a good use of your day. Instead, focus on something you’re good at, and take it from good to great. You may never overcome a weakness, but you could make a huge impact on your life and career if you focus on your strengths.

So, how do you figure out what your strengths are?

Talk to the people who know you best: your coworkers, friends, and family. Ask them what they consider your strengths to be. Tell them to be brutally honest. Where do they think you excel? Be ready for these conversations to sting, a little.

Don’t discount any of the feedback they give you. If your inner circle loves the way you write, for example, think about all the ways you can leverage that strength. Can you adjust your career path to incorporate more writing? What if you started a blog – or a weekly newsletter – where you could practice and refine your writing skills?

Examine the times you’ve done your best work; the kind of work that left you feeling happy, energized and fulfilled. What are the commonalities? Which your skills did you employ? How can you re-create those moments?

It can be a lot of work, to be honest. But if you can figure out where your strengths lie and put more of your effort into those areas, I bet you’ll be happier, more productive, and – ultimately – more successful in your work.

What do you think? Is laser-focus on your strengths the right move? Reply to this email – I’d love to hear your thoughts.

Cheers,

–Brian


How I Write & Publish a Weekly Newsletter

I often receive questions about how I run the Monday Mailer, my weekly newsletter about shipping side projects, productivity, and doing your best work. Readers ask what my writing process is like, and which software tools I use. While I firmly believe tools aren’t all that important — you can make something great, no matter the means— I thought I’d write some of it up for anyone interested. Planning I publish my newsletter every Monday, and the occasional article during the rest of the week.

I often receive questions about how I run the Monday Mailer, my weekly newsletter about shipping side projects, productivity, and doing your best work. Readers ask what my writing process is like, and which software tools I use. While I firmly believe tools aren’t all that important — you can make something great, no matter the means— I thought I’d write some of it up for anyone interested.

Planning

I publish my newsletter every Monday, and the occasional article during the rest of the week. I also contribute guest posts to other sites, from time to time. I manage all of my writing tasks through Trello. My writing board has a lot of lists on it — 17 in total. They cover everything from the latest newsletter drafts, to guest posts I’m writing, to tracking where I’m publishing & promoting my work. Here’s a quick rundown:

  • Ideas: Whenever I think of something that might make for a good article, I throw it in here. I try not to edit these thoughts too early — if it’s rattling around in my brain, it goes on the list. There’s somewhere in the neighborhood of 60 cards, so far.
  • On Deck: Cards from the “Ideas” list I’m hoping to work on next.
  • Process: Lists that cover every step in my writing & editing process: Outline, 1st Draft, 2nd Draft, 3rd Draft, and Edited.
  • Published: Lists for every place I regularly post my articles: Mailing List, Medium, and LinkedIn.
  • Promoted: Lists for every site I usually use for promoting my work: Hacker News, Designer News, Reddit, and more.
  • Pitched: A single list for keeping track of which publications I’ve submitted to, along with the article and current status.

Phew! My Trello board is probably getting a bit out of hand. But I have so much going on every week; I need an external brain to keep everything organized. Okay, let’s dive into my writing process.

Writing

Like many writers, I take an iterative approach. Each round builds on the last. Here’s what it looks like, roughly:

  1. Fire up Ulysses and write a quick and dirty outline. I spew my thoughts onto the page. Every little thought that pops into my head gets written down. I don’t edit or change anything at this stage — it’s all about getting my brain warmed up. If there’s something I need to research, I jot it down as well. Then, I walk away for a while.
  2. Come back, throw the outline on the left side of my screen, and open a new document on the right. I start by expanding on the bullet points in the outline. Again, I’m not too worried about details at this point. I write until I have something mostly resembling sentences and paragraphs. Then, I walk away for a bit.
  3. Put the last draft on the left side of the screen, and a new document on the right. Noticing a pattern, yet? Now it’s time for the real work. On this pass, I work on refining my ideas. I ask myself a few questions: Are things coming across clearly? Am I writing in a way that feels authentic to my personality? Are there any obvious problems? I fix anything I find and then — you guessed it — walk away for a bit.
  4. For this last pass, I run the article through Grammarly. I shell out for the Premium plan every month. It isn’t perfect, but it usually catches a few things I missed in the last draft. Worth every penny, considering the amount of writing I do each month.

I try to dedicate a couple hours to writing every morning. Some articles take a few days — or weeks — to complete; others I can knock off in a few hours. Doing a little bit every day means I always have something I can publish. It also means I’m sometimes a week or two ahead of schedule, which is useful for those moments life throws a curveball my way.

Publishing

The Monday Mailer has 1,168 subscribers as of this writing. I use Mailchimp’s Send Time Optimization tool to send new articles at an ideal time for the majority of my readers. It usually lands somewhere between 9–10am EST.

After I schedule the week’s newsletter, I add the article to my blog. I used to enjoy fiddling around with hosting my website, but I use Squarespace and enjoy the simplicity it offers. Again, worth every penny. I schedule the blog post to publish two weeks after it goes out to the mailing list. I do the same for the Medium version.

Squarespace automatically tweets a link to the post, once it’s live.

A few people have suggested LinkedIn as a good place to share new articles, so I’ve been giving that a try, as well.

Interacting

My favorite social network is my mailing list. I set time aside all week to respond to emails from my readers. I’m lucky — they’re never short on feedback and suggestions.

Since the public version of the article is scheduled ahead of time, I can mostly forget about it until it goes live. Once it does, I spend a good chunk of time monitoring the comments, as well as social media, for comments and reaction. I make sure to thank everyone who shares my work. Everyone I can find, at least.

Fin

That’s it! It’s a relatively simple process. But it’s one I can repeat consistently, week over week. And that’s the most important part.


Activation Energy

There’s a chemistry term I recently learned: activation energy. It’s the amount of energy required to start a chemical reaction – which is always higher than the amount needed to maintain the reaction. It’s like trying to push a giant boulder. You strain and grunt at first, struggling to push it even an inch. But once it starts rolling, it takes a fraction of that initial energy to keep it moving.

There’s a chemistry term I recently learned: activation energy. It’s the amount of energy required to start a chemical reaction – which is always higher than the amount needed to maintain the reaction. It’s like trying to push a giant boulder. You strain and grunt at first, struggling to push it even an inch. But once it starts rolling, it takes a fraction of that initial energy to keep it moving.

It’s a concept that applies to our work, too. There are times I sit down to write the Monday Mailer and, despite the brainstorming and outlining I’ve done, the words just won’t come. But I know if I start typing something, anything, it’ll get easier.

Here’re some of my ideas for lowering the activation energy required to do your work.

1. Set a timer

I’ve recently become a fan of the Pomodoro Technique. I sit down, set a timer for 25 minutes, and focus exclusively on writing until it goes off. I don’t worry about sentence structure or proper grammar, I just write. More often than not, it helps my brain warm up, and I write for an hour or more.

2. Do a little bit, every day

A small, focused task – done daily – beats sporadic effort every time. It’s hard to gather the energy to start something new; especially after an extended absence. If I write a little bit every day, it’s a lot easier to publish the newsletter each week. But if I wait until Sunday night, it feels like an impossible task. I recently started dedicating two hours to writing every morning, and it’s made a huge difference in my output.

3. Be prepared

There’s a term from the culinary world I love: mise en place. It means “putting in place.” It refers to the work you have to do before you start cooking – organizing your ingredients and tools. It’s the work before the work. We can steal this concept for our projects. At the end of the day, take the time to clean up your desk, cross items off your to-do list, and make a plan for the next day. You’ll thank yourself, tomorrow.

This stuff works for me, but I’m curious: what techniques do you have for gathering the energy to start something new? Reply to this email and let me know. I’ll try to share some of the ideas in next week’s email.

Until next time,

–Brian


Make a (Public) Commitment

I’m writing this article because I have to – I’ve set a deadline. One new article a week, no matter what. It’s a time limit that’s entirely self-imposed, but I’ve committed to it publicly, and now I have to stick to it. Setting a deadline and sharing it with the world is the most effective strategy I’ve found to force myself to be productive. The more public the commitment, the better.

I’m writing this article because I have to – I’ve set a deadline. One new article a week, no matter what. It’s a time limit that’s entirely self-imposed, but I’ve committed to it publicly, and now I have to stick to it.

Setting a deadline and sharing it with the world is the most effective strategy I’ve found to force myself to be productive. The more public the commitment, the better. If I tell everyone I’m going to write one article a week and fail, I’m going to feel pretty awful. So, I work hard to make sure I don’t have to feel that way.

It’s a strategy I’ve used in my personal life, too.

For a long time, I hated running. I tried it a few times over the years, but always gave up. I’d look at the thin people running laps around me and decide, time and time again, that running just wasn’t for me. I hated that I gave up so quickly. So this summer, when a coworker started recruiting people for a 5k, I decided to make a change.

Before I could second-guess myself, I signed up for the race and paid the registration fee. This time I would have to stick with it. Otherwise, I’d end up looking pretty bad in front of my team. I committed. To up the ante even more, I tracked my runs with Strava and posted the results to our Slack channel, along with Twitter and Instagram. Lots of people responded with words of encouragement – which felt great. But it also made me feel accountable to them.

In October, I ran my first 5k without stopping. A small distance for most of you, I’m sure. But to me, it felt like all the distance in the world. It was easily my biggest accomplishment of the year.

To become good at our work, we have to put the hours in. A deadline, announced publicly, forces you to stop being precious. It kills perfectionism and resistance to just getting shit done. The more deadlines I set, and commitments I make to other people, the more I’m able to get done.

Until next time,

–Brian


Batching Tasks

Lately, I’ve been struggling with the amount of context-switching I have to do each day. One minute I’m knee-deep in coding, the next I’m interviewing a prospective employee or doing a 1-on-1 with a member of my team. And that’s before I get to any meetings I have to attend. Oh, and don’t forget about the emails piling up in my inbox. It’s frustrating. Every switch means 20 minutes of trying to get back in the “zone” and, by the time that happens, it isn’t long before I have to run off to my next task.

Lately, I’ve been struggling with the amount of context-switching I have to do each day. One minute I’m knee-deep in coding, the next I’m interviewing a prospective employee or doing a 1-on-1 with a member of my team. And that’s before I get to any meetings I have to attend. Oh, and don’t forget about the emails piling up in my inbox.

It’s frustrating. Every switch means 20 minutes of trying to get back in the “zone” and, by the time that happens, it isn’t long before I have to run off to my next task. I haven’t been able to give 100% of my attention to anything. And that isn’t fair to me, or my coworkers.

Despite having quite a bit of agency over how I schedule my time, I’ve never actually taken advantage. So, last week I decided to experiment with a technique I’ve heard a lot about over the years: batching similar tasks. I decided to tackle the two biggest pain points first: meetings and email.

Meetings

I’ve moved all of my non-project work to one day a week: Wednesday. From morning to night, Wednesday is now my “sit in a room and talk to people” day. Internal meetings, client meetings, interviews, 1-on-1s, you name it. Where possible, they all happen on that same day. I try to schedule consecutive meetings in the same room to cut down on the amount of running around I have to do.

It isn’t perfect – last Wednesday was a long day – but it means I can put myself in the right state of mind for whatever the day will bring. Is it Wednesday? Okay, that means I need to be ready to sit down, be mentally present, and have real conversations with my team. Any other day? Time to crank out code.

Email

I’ve scheduled two 30-minute blocks each day for processing my email; 9 am and 4 pm. All other times, my email client is closed. I’ve also set it to only fetch new mail manually, just in case my muscle memory kicks in and I open it accidentally.

When an email block rolls around in my calendar, I take the approach that every email in my inbox has to be dealt with in that time. I force myself to make a choice to either respond immediately or ignore/archive it. Every once in a while, an email has to wait until the next email block – or even the next day. But I never go over my 30-minute window. I’ve found most emails can be answered right away, or don’t need a response at all.

Experimenting

I’m only a week into this experiment, but the results have been promising so far. I’ll be sure to let you all know how it goes. At best, it will improve my productivity. At worst, it’ll be a good example of what not to do.

Like most things in life, I suspect the answer will fall somewhere in the middle.

Until next time,

–Brian


Test Your Idea (And Assumptions)

Lately, I’ve been playing around with the idea of creating a Monday Mailer podcast featuring audio versions of my articles, along with occasional original content. I’ve dabbled with audio projects in the past, but never on a regular basis. It’s an exciting idea, but I’m most definitely an amateur when it comes to this sort of thing. It can be scary to try something outside your comfort zone, whether it’s a side project, added responsibilities at work, or a new hobby.

Lately, I’ve been playing around with the idea of creating a Monday Mailer podcast featuring audio versions of my articles, along with occasional original content. I’ve dabbled with audio projects in the past, but never on a regular basis. It’s an exciting idea, but I’m most definitely an amateur when it comes to this sort of thing.

It can be scary to try something outside your comfort zone, whether it’s a side project, added responsibilities at work, or a new hobby. You’re putting yourself out there, raw and vulnerable. But if you don’t push your boundaries every once in a while, you’ll never grow.

I have no idea if my podcast idea will be well-received. So, instead of jumping in with both feet, I’m reframing the concept as a simple test. There’re a few questions I’m hoping to answer:

  1. Is a podcast something my audience wants?
  2. Do I have the ability to produce a quality episode, each and every week?
  3. Can I speak in a way that’s warm and inviting, rather than annoying?

Instead of committing lots of time and resources to trying it out, I’m putting on my lab coat and testing a hypothesis: “I can produce a podcast episode that people will enjoy listening to.” You can take this approach in your work, too.

Break your idea down into the smallest possible version of itself. Ask yourself:

“What’s the least I can do to test this out in front of real people?”

Cut everything else out and share it with the world. Right now. It isn’t easy – you’ll worry it isn’t polished enough. But that’s the point. If your audience doesn’t “get it” in the rough stages, it’s unlikely a few extra hours of work will change their minds. You can always improve it later if the feedback is positive.

In my case, I recorded a quick test track – around a minute and a half long – and put it up on my website. I added a quick, anonymous survey and tweeted out the link. So far, the feedback has ranged from “This is awesome!” to “You sound like you’re copying Ira Glass.” Some of the more critical comments sting a little, at first. But I’d rather hear them now than ten episodes down the road.

It’s important that we separate ourselves from our work, sometimes. Don’t hold any idea so tight you can’t make changes or move on if needed. It might take 100 failed experiments before you find something that works. And that’s okay.

Real success isn’t hitting it out of the park with every at bat. That never happens. Real success is spending your time on what matters and making the most of it.

Until next time,

–Brian


Making Time for Side Projects

This week’s article is as much a reminder to myself as it is advice for you. I haven’t done a good job of managing my time, lately. Instead of writing or pushing my side projects forward, I’ve been binge-watching Netflix, reading blog posts full of productivity tips, and playing copious amounts of Pokémon Go. Time to re-focus. Here are some tips for making more time for your side projects. I’ll be re-implementing a bunch of them myself, this week.

This week’s article is as much a reminder to myself as it is advice for you. I haven’t done a good job of managing my time, lately. Instead of writing or pushing my side projects forward, I’ve been binge-watching Netflix, reading blog posts full of productivity tips, and playing copious amounts of Pokémon Go.

Time to re-focus.

Here are some tips for making more time for your side projects. I’ll be re-implementing a bunch of them myself, this week.

Control your schedule

Do everything you can to control your schedule, free of interference from other people. When you do creative work, you need extended periods of uninterrupted time to focus. It’s up to you to create that time.

If someone walked up to you and asked for $100, you’d rightfully have questions. But we rarely apply the same standard to our calendars. Don’t blindly accept every meeting request you receive. Figure out when you’re most productive and schedule around those times.

Granted, this can be difficult if you work at a full-time job or have family commitments. Those hours are accounted for already. But there’s lots of wiggle room if you’re intentional about how you spend the rest of your time.

Stop consuming, start creating

I know it’s a bit ironic for me to suggest this, what with running this mailing list and all. But, at a certain point, you have to stop consuming other people’s content and start creating your own. Articles full of tips & tricks, productivity hacks, and other bullshit can be helpful – for a while.

But every second you spend learning about productivity is a second you aren’t, well, being productive. How often do you apply what you’ve read to your work? Almost never, if you’re anything like me. It’s a trap.

Once you’ve read something valuable stop, think about how you can apply it to your life, then close your browser and go do it. Favour action. You’ll learn more that way, anyway.

Stop doing shit you hate

Often, out of a sense of obligation or guilt, we commit to doing things we hate. It doesn’t just eat up your time; it erodes your overall happiness and satisfaction. Derek Sivers put it best: “If you’re not saying ‘HELL YEAH!’ about something, say ‘no.’”

Cancel any commitment you aren’t 100% invested in.  

Prepare for tomorrow

Sometimes the hard part isn’t making time for your work; it’s getting started once you’re staring at a blank page. It isn’t always easy to turn free time into productive time (see: my Netflix binge-watching). The more you can reduce the effort it takes to get down to work, the better.

As you’re wrapping up your day, ask yourself one question: “What’s something I can do – right now – to make it easier to do my work tomorrow?”

It could mean cleaning off and organizing your desk. Or writing a to-do list. Or deciding on your next writing topic. It will be unique to you and whatever you’re working on right now. It’s a habit you’ll have to work on developing, at first. But once you do, you’ll thank yourself each and every morning.

Until next time,

–Brian


What's Your North Star?

On a clear night, with just the right conditions, there’s about 6,000 stars visible to the naked eye. As far back as the 2nd century, human beings have looked to those stars to help determine their location and heading. And none is more well-known than the North Star. The North Star has one unique property: it never moves. Okay, that isn’t strictly true. But for all intents and purposes, you can count on it staying put — right above the North Pole.

On a clear night, with just the right conditions, there’s about 6,000 stars visible to the naked eye. As far back as the 2nd century, human beings have looked to those stars to help determine their location and heading. And none is more well-known than the North Star.

The North Star has one unique property: it never moves. Okay, that isn’t strictly true. But for all intents and purposes, you can count on it staying put — right above the North Pole. If you were trying to navigate in the days before GPS, knowing which way was north turned out to be pretty handy.

When it comes to doing our best work, I think we all need our version of a North Star — something that reminds us where we’re going and what we’re trying to accomplish. My North Star is “Be Useful.” When I’m feeling lost, unsure of what to do next, or stuck, I know I can’t go wrong trying to bring value to someone else.

I’ve said before that procrastination is a byproduct of fear. Fear of failure. Fear of other people’s opinions. Fear of not being “good enough.” But I think there’s another angle.

Procrastination is forgetting our North Star.

When we get stuck on a project, it’s helpful to remember why we started working on it in the first place. Most of my early side projects were a response to a job I hated. The work was uninspiring, the clients were awful, and I wasn’t learning anything new. I knew I wouldn’t be able to get a better job with the kind of work I’d been doing. So one night, at the peak of frustration, I said “fuck it” and started coding. I realized there was only one person who could change my situation: me.

You’d think that would be sufficient motivation to carry me through to the end of the project. But it wasn’t. There we so many nights where all I wanted to do was flop onto the couch and watch TV. But it didn’t take long before a tiny voice in my head spoke up.

“I thought you wanted more than this?”

Once I remembered my purpose — my North Star — it became hard to justify six hours of TV on the couch.

Your North Star can be anything that speaks to the heart of why you started a side project in the first place. Landing a more fulfilling job, satisfying the creative half of your brain, improving your skills, or creating a better life for those you love.

No one can tell you what your North Star is. It’s something you have to decide for yourself. So decide, right now. Write it down and put it somewhere you’ll see it every day.

And when those dark, tired moments happen — and they will happen — take a look at that piece of paper, and remind yourself of what drives you.

Until next time,

–Brian


Crossing the Finish Line

Before I dive into this week’s article, I want to extend a warm welcome to everyone joining us for the first time. After Be Kind reached the top of Hacker News, the Monday Mailer grew by more than 600 subscribers – in less than 48 hours. I’m glad you’re here! Have you ever found yourself close to finishing a side project, only to become stymied by one last task you need to complete?

Before I dive into this week’s article, I want to extend a warm welcome to everyone joining us for the first time. After Be Kind reached the top of Hacker News, the Monday Mailer grew by more than 600 subscribers – in less than 48 hours. I’m glad you’re here!


Have you ever found yourself close to finishing a side project, only to become stymied by one last task you need to complete? You have to figure out how to integrate Stripe payments. Or you’re futzing around with the landing page design. You know you should just ship the damn thing but, for whatever reason, you can’t.

It feels like running the New York Marathon. Except when you near the finish line, there’s a brick wall in your way. At that point many of us give up and walk away, promising to do better next time. But the cycle continues. We start the next project full of energy. Then, as we near the finish line, we stall. Again.

I’m as guilty of it as anyone. Here’s a gem Facebook surfaced recently. 

Facebook Screenshot

I never did ship that project, by the way. If I had a nickel for every side project I’ve abandoned, I’d be living large right now.

Why do we allow ourselves to get so far, only to succumb to procrastination? 

Often, deep down, it’s because we’re afraid. Afraid of failure. Afraid of what our family and friends will think. Afraid that, if everything isn’t just perfect, we’ll have wasted our time. Afraid that we’ve built something nobody wants. It’s safer to keep fiddling around – secure in the knowledge that, as long as the project sits on our hard drive, we don’t have to risk anything. 

It’s self-sabotage. And, for those of us trying to do our best work, build an audience, and make an impact, it’s a habit we have to break.

A lot of times people fall into this pattern because they put the concept of “Launch Day” on a pedestal. They think they get one shot to reach a huge number of people and impress them. They’re not only wrong – they’re limiting their audience

When I started working on Chronicons, my icon set for Apple Watch apps, I took the opposite approach. Instead of hiding it away from prying eyes, I shared what I was doing as often as possible. I wrote about it on my blog, posted updates on Twitter, and solicited feedback on Dribbble. I got valuable comments and advice from designers around the world and built up an audience of people who couldn’t wait to buy from me. And they stuck around once the launch had come and gone! It’s a process I’ve repeated a few times since, with similar results. 

I won’t lie – it’s hard to do, the first few times. But it gets easier with practice.

You side project could be a huge hit. Or, it could be a disappointing flop. But until you can set aside your fears and share it with the world, you’ll never find out. 

You – and your work – deserve better.

Until next time,

–Brian