Brian Gilham

Engineering leader, husband, and father

side-projects

If you’ve been following me for a few years, you might remember when I wrote the Monday Mailer — an email newsletter about productivity, side projects, and feelings. I’m really proud of some of those articles. Some of them make me cringe. Regardless, you can now find the archives here.


Finding the Time

“I’d love to work on my own projects, but I never seem to find the time.” If I had a nickel for every time I’ve heard some variation of that line, I’d have a whole lot of nickels. Several vaults worth, at least. You’ve probably heard it too — coming out of your own mouth, even. The idea that you’ll magically “find” the time to work on your side projects is silly.

“I’d love to work on my own projects, but I never seem to find the time.”

If I had a nickel for every time I’ve heard some variation of that line, I’d have a whole lot of nickels. Several vaults worth, at least. You’ve probably heard it too — coming out of your own mouth, even.

The idea that you’ll magically “find” the time to work on your side projects is silly. Once you’re done working at your day job, spending time with friends & family, and dealt with personal commitments, it’s hard to imagine finding even a spare second for anything else. Oh, and let’s not forget about those times life decides to throw you a curveball or two — as it does, from time to time.

But there’s something we all know deep down, even if don’t want to admit it to ourselves.

Thinking you don’t have any time is just an excuse.

(There are exceptions, to be sure. We all have moments where side projects are far from a priority. Having gone through it recently, I know that quite well. If you’re going through just such a time right now, feel free to disregard this advice until your life is back in order.)

We all feel like we’re working too much — that we have enough on our plates already. But if you’re going pursue the projects you’re most passionate about, you’re going to have to start prioritizing them. You’re going to have to optimize the time you have available.

Life will eat up every spare moment if you let it. If you’re serious about pushing your projects forward, you’re going to have to fight for the time to do it. 

How? By eliminating time spent on bullshit.

What’s bullshit? It’s time spent on consuming other people’s work, rather than producing your own. Or time spent on mindless busywork. Or doing things just to “stay busy.”

How much time are you spending: * Watching hours of television, or playing video games? * Reading every last post in your social media feeds? * Reorganizing your desk, or hard drive, for the 1000th time? * Hanging out with people you hate, doing things you don’t enjoy? It’s time to take control of your schedule.

If I walked up to you and asked for $100, you’d rightfully have some questions for me. Like, “Why the hell should I give you $100, random stranger from the internet?”

But when was the last time you applied even that low standard to your time? Time is one of the few finite resources in life but, far too often, we give it away freely.

Stop blindly accepting every meeting request you receive. Learn to say no to things you don’t want to do — or can’t contribute to in a meaningful way. Figure out when you’re most productive and schedule your days around that time.

Ask yourself some hard questions. Why are you spending time watching TV, or reading blogs, when you could be coding your next web app? Why are you blowing time reading Twitter, when you could be brainstorming your next great idea? Instead of listening to someone else’s podcast, why aren’t you creating your own?

Why are you reading this email, rather than doing something else?

You need to consciously decide to change those habits. It won’t be easy. But you’ll be amazed how much time you can “find” once you stop consuming and start creating. And start being intentional about your time.

Until next week,

-Brian


The Tao of Gordon Ramsay

I don’t watch much television these days, but one of my guilty pleasures is old episodes of Kitchen Nightmares. Each episode, through the power of cursing and walking around in dramatic fashion, Gordon Ramsay works to turn around a struggling restaurant. After a quick look around, Gordon inevitably finds a laundry list of problems — everything from dirty fridges to undercooked food, to terrible service. But there’s one problem that crops up, time and time again: large, unfocused menus.

I don’t watch much television these days, but one of my guilty pleasures is old episodes of  Kitchen Nightmares. Each episode, through the power of cursing and walking around in dramatic fashion, Gordon Ramsay works to turn around a struggling restaurant.

After a quick look around, Gordon inevitably finds a laundry list of problems — everything from dirty fridges to undercooked food, to terrible service. But there’s one problem that crops up, time and time again: large, unfocused menus.

Frequently, chefs and owners think the surest path to success is to overwhelm their customers with hundreds of options, spanning multiple cuisines. Their menus are confusing, wait staff are overworked, and the kitchen is chaotic. Each time, Gordon has to sit them down and explain the value of doing a handful of dishes well. Often, he ends up cutting their menu in half.

The result? Customers are less confused, wait staff can recommend their favorite dishes, and cooks aren’t forced to run around like chickens with their heads cut off, trying to cook everything under the sun.

I’ve started to recognize the problem with large menus at the restaurants I visit. More often than not, it means poor food and service. It’s *almost* a universal truth.

A similar problem pops up in failing side projects.

Often, developers worry they’ll “blow it” by cutting features from the first version of their product. Driven by fear, and lacking real feedback on their ideas, they delay launching while they add “just one more feature” or spend three days pushing pixels on the home page.  They try to cram their app’s menu full of *everything* that pops into their head — both figuratively and literally. Then, they wonder why they never seem to launch anything.

Gordon would be disappointed.

In my experience, shipping something half-finished hurts a lot less than never shipping it at all. 

It’s easy to look at someone else’s work and marvel at how polished it is. But remember, every side project could have been better or included more features. Those developers, the ones who consistently ship? They’ve embraced an important idea — at some point; you have to stop. You have to ship.

Until next week,

-Brian


5 Reasons to Boost Your Career with Side Projects

If you’re a programmer, *particularly* early in your career, there’s no better way to learn new skills, promote yourself, and improve your job prospects than working on side projects. Full stop. Brainstorming, developing, and releasing side projects has been a force multiplier in my career — and it can do the same for you. Always working on side projects comes naturally to me, but I know that isn’t the case for everyone.

If you’re a programmer, *particularly* early in your career, there’s no better way to learn new skills, promote yourself, and improve your job prospects than working on side projects. Full stop. Brainstorming, developing, and releasing side projects has been a force multiplier in my career — and it can do the same for you.

Always working on side projects comes naturally to me, but I know that isn’t the case for everyone. Why should you spend your precious free time coding when you could be watching TV, hanging out with friends, or playing video games?

It’s a question worth examining; why *are* side projects so important?

The answer to this issue has a few different angles — and it’s going to be a little bit different for everyone. But here’s five reasons I think you should be working on a side project.

Low-stakes learning

We all know how important it is to stay on top of changes in the programming landscape. There’s *always* a new technology, library, technique, or platform to learn. Things are moving fast and, if you don’t keep up, there’s a good chance you’ll find yourself out of date. Working on a side project gives you the opportunity to pick up new skills in a low-stakes environment. If a side project fails, you don’t need to worry about letting down your team, pissing off your boss, or not being able to pay rent. You can try new things and learn from your mistakes, all at your pace.

Becoming an expert

If you’re willing to jump on new platforms before anyone else, you can quickly become the resident expert at work. When the Apple Watch SDK came out, I poured hours into building apps, mocking up potential interfaces, and sharing what I learned.

When the opportunity to do an Apple Watch project came up at work, I was the natural choice to lead it. Now, when new Watch projects pop up, I’m often asked for guidance and advice. It’s just one way I’ve increased my value at work and differentiated myself from others.

Landing your first job

If you’re a junior developer, looking to land your first job, side projects can help. There’s one big thing holding you back; your resume is more Sales Associate at Home Depot, less, Front-End Developer at Company X.

A lot of junior developers bump up against that wall for *far* too long, stuck at a crappy job with no real opportunity to learn and grow. Side projects give you a way out, building a reputation and portfolio for yourself.

Cultivating a portable reputation

Working on side projects can give you what Sean Fioritto calls “portable reputation.” If you’ve worked at one place for a long time, there’s a good chance you’ve built up a fantastic reputation and a fair bit of credibility. But there’s a big problem; that status is locked up with your employer.

If you leave, and you haven’t put time into cultivating a portable reputation, you’ll be relying primarily on your resume to help you stand out from the crowd. Can you land a job solely on the strength of your resume? Of course. But why not take *every* advantage you can get? The demand for developers is huge right now, but it won’t last at this level forever. Side projects give you the opportunity to build a reputation independent of your employer. And reputation is leverage.

Sweet, sweet cash (maybe!)

While it shouldn’t always be your primary goal, there’s also the possibility of a side *project* turning into a side business. Some of the most successful companies were born out side projects — Gmail, Buffer, and Todoist come to mind.

Between apps and other digital products, I’ve managed to make some significant money from my side projects. Nothing life-changing, mind you. But once you start making money from a product or service of your creation, you’re forever changed. When you know how to plan, execute, promote, and sell your work, you become more self-sufficient. Once you realize you can generate income based on value, and not time spent, there’s no going back.

Until next week,

-Brian


Walk Before You Run

You sit down to start your next project, full of energy and enthusiasm. You’re excited; starting something new is an opportunity to make something great. It starts out simple but, over time, grows into something unmanageable. You add a new feature here, a design tweak there. Until, eventually, your perfect little side project has become something else entirely. Later, with a huge list of tasks to complete and no sign of launching on the horizon, your energy fades.

You sit down to start your next project, full of energy and enthusiasm. You’re excited; starting something new is an opportunity to make something great. It starts out simple but, over time, grows into something unmanageable. You add a new feature here, a design tweak there. Until, eventually, your perfect little side project has become something else entirely.

Later, with a huge list of tasks to complete and no sign of launching on the horizon, your energy fades. You start getting frustrated. Working on your side project stops being fun. You aren’t learning anything new; you’re just trying to *finish* the damn thing.

We’ve all been there. It’s a struggle as old as time itself.

It’s a cycle of failure and, if you don’t change your approach, it’s one you’ll repeat over and over. Managing constraints, priorities, and scope is easy — when you’re at work. There are external pressures and expectations motivating you to get shit done. But when you’re working on a side project — when every decision is yours, and yours alone — you struggle.

Take a moment, right now, and think about why you failed to ship your last project. You might believe the problem was a lack of willpower, discipline, or motivation. You might think your idea, well, sucked. But there’s a good chance that wasn’t the problem at all. The problem was scope management.

You don’t become a master painter overnight. No, you start by painting something small. Taking some classes and learning the basics. *Practice, practice, practice.* The same principle applies to shipping your side projects. Once you successfully launch one small, manageable project, you can ramp up a little bit. Then, ramp up some more. Shipping is a skill that can be learned and practiced, like any other.

So start practicing.

Until next week,

-Brian


5 Thoughts on Doing Effective Work

When I talk to fellow side project enthusiasts, I often hear them say, “I wish I could get more done.” It isn’t surprising. When you’re working on a side project — constrained by your day job, friends, family, and more — even the smallest productivity gain can make a huge difference in your overall output. If you only have an hour each morning to push your project forward, every minute counts.

When I talk to fellow side project enthusiasts, I often hear them say, “I wish I could get more done.” It isn’t surprising. When you’re working on a side project — constrained by your day job, friends, family, and more — even the smallest productivity gain can make a huge difference in your overall output. If you only have an hour each morning to push your project forward, every minute counts.

One mistake developers make — myself included — is trying to get as much done as possible, rather than focusing on doing work that matters. We plug away at what’s easy, instead of what’s important; the tasks that truly move the needle on our projects.

Here are some thoughts on how you can consistently identify what’s important and make progress on your side projects.

Clear Your Mind

I used to hate using a calendar, to-do apps, or a planner; I didn’t think I needed them. I was wrong. So very wrong.

When you have 100 different tasks, events, and ideas bouncing around in your head, it’s easy to get overwhelmed and start procrastinating. To gain the clarity needed to do useful work, you need to get that clutter out of your head and into an external system.

It’s like remembering phone numbers. When I was growing up, it was important to recognize a variety of phone numbers. Today, every number I could ever need is stored on my phone, or easily found online. Heck, most of the time I just need to tap on a person’s face, and I’m connected to them instantly. The phone number itself doesn’t matter. Thanks to technology, I’m able to free up the part of my brain that used to remember phone numbers.

You need to do the same thing for your to-do list. It’s almost impossible to get anything organized until it’s out of your head. Once you clear your mind, you can more quickly focus on the work that matters.

Learn from Eisenhower

You need to realize most tasks fall into one of two categories; important or urgent. They’re rarely the same thing. Dwight Eisenhower once said:   > “I have two kinds of problems; the urgent and the important. The urgent are not important, and the important are never urgent.”

The “Eisenhower Method,” described in First Things First, categorizes tasks into one of four quadrants:

  • Important/Urgent: Do it now.
  • Important/Not Urgent: Plan when you’ll do it.
  • Unimportant/Urgent: Delegate it.
  • Unimportant/Not Urgent: Don’t do it at all.

For each task on your to-do list, take a page from Dwight Eisenhower and ask yourself if it’s important, urgent, or neither.

Break it Down

There’s one significant benefit to moving your to-do list from out of your head and into an external system; it becomes much easier to break tasks down into smaller pieces and start to schedule them.

When you’re working on a project, it’s easy to imagine the end product and get overwhelmed. If I pointed at a fancy SUV and asked you to build me one, there’s a good chance you’d get stuck and procrastinate. That’s because “build me an SUV” is a terrible request. Where would you even begin?

The project starts to look a lot more manageable when you break it down into smaller tasks. Instead of “make a car,” you might start with “learn how a car engine works.” Once you’re through that, you might move on to finding the parts you need, ordering them, then finally building the motor.

After that, maybe you’d move on to the wheels. Or the chassis. Eventually, one small piece after another, you’d have an entire car.

Now, that’s a silly example. Most of us aren’t learning to build an entire car from scratch. But the same approach can be applied to your work. One of the biggest secrets to my productivity is making tasks as small as humanly possible. If I only have time to get through one 30-minute task in a day, and I finish it, I consider it a successful day.

By breaking my tasks down into ever-smaller pieces, it’s harder for me to lose track of progress. And I’m always crossing things off my to-do list — which feels great.

Deadlines, Deadlines, Deadlines

I’m a huge fan of setting public deadlines for my projects. I often remind myself of Parkinson’s Law, which states:   > “Work expands to fill the time available for its completion.”

There’s never enough time in the day. Or week. Or month. By setting a deadline, you’re forced to cut your project’s scope down to a manageable size. It pushes you to be realistic about how much you’ll be able to get done.

Take a Break, Once in a While

We’re all familiar with the culture of HUSTLE pervading the programming & startup communities these days. I’m as guilty of buying into it as anyone; I constantly feel like I’m falling behind and should be doing more. But, as good as it can feel — temporarily — to forgo sleep and crank out code like there’s no tomorrow, you’ll eventually pay the price.

You shouldn’t try to push yourself to the limit during every waking moment. It’s unsustainable. Eventually, you’ll burn out. Hard.

Instead, your goal should be to do good work over the long haul. To do work you’re proud to show off. To do it at a pace you can sustain over time. Your career is a marathon, not a sprint.

It’s easy to push off exercise, relaxation, and eating well. I’ve done it before, many times. But as I’ve gotten a bit older, I’ve realized those are the very things your body most needs to do your best work. If I spend too many days at my desk without exercise, I start to feel awful pretty quickly. 

I’m willing to bet your best ideas don’t come to you when you’re at your desk, slaving away. No, I’d bet they come to you when you’re relaxing, in the shower, or riding your bike.

You have a finite amount of energy, each week. When you work at 110% capacity every day, it disappears pretty quickly. Your brain needs time to relax before it can produce good, creative ideas. Respect your limits, and your productivity will skyrocket.

Your Turn

What strategies do you have for discerning between tasks that are urgent or important? How do you decide where your focus should be? Shoot me a reply, right now, and let me know.

Until next time,

–Brian


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


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


Side Projects = Investments

There’s a trend I’ve noticed lately — both online and in my inbox — that I find troubling. Someone will share an idea for a side project and immediately follow it up with a comment like, “But there’s no point in doing it — it isn’t monetizable.” What? When did working on a side project become so driven by a desire to make money? Sure, it’s hard to read an article titled, “Tricks to Monetize Your Side Projects” and not want to get a piece of the action.

There’s a trend I’ve noticed lately — both online and in my inbox — that I find troubling. Someone will share an idea for a side project and immediately follow it up with a comment like, “But there’s no point in doing it — it isn’t monetizable.”

What?

When did working on a side project become so driven by a desire to make money? Sure, it’s hard to read an article titled, “Tricks to Monetize Your Side Projects” and not want to get a piece of the action. But a good side project can offer so much more.

A side project is a long-term investment in your skill set, creativity, and career development. I landed my job at TWG based on the strength of my side projects. I found many of my friends and acquaintances through side projects. I picked up a lot of skills through — you guessed it — side projects.

If your project ends up making money, awesome. But if you’re thinking about starting something new, monetization should be the last thing you think about — not the first. If it stops you from getting down to work, it’s just another form of procrastination.

Don’t throw away the opportunity to invest in yourself just because you don’t see a path to profits.


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


Be Boring

I’ve become known as a prolific doer of side projects. In the last few years, aside from my responsibilities at TWG, I’ve released six apps, served as technical reviewer on a book, published a weekly newsletter about Apple Watch development, designed and sold the first icon set for Apple Watch apps, spoken on a variety of topics, and published more than 40 blog posts, articles, and tutorials. Phew! That list isn’t meant to impress you.

I’ve become known as a prolific doer of side projects. In the last few years, aside from my responsibilities at TWG, I’ve released six apps, served as technical reviewer on a book, published a weekly newsletter about Apple Watch development, designed and sold the first icon set for Apple Watch apps, spoken on a variety of topics, and published more than 40 blog posts, articles, and tutorials. Phew!

That list isn’t meant to impress you. If anything, it might just illustrate an unhealthy disregard for rest and relaxation. I’m not here to shout HUSTLE MORE! at you. I’ve been that guy before. That guy sucks. If you’re happy with your output, by all means, you do you.

But I get asked about my productivity a lot, and if you’re like me – always looking for the next project, never able to sit still, always wanting to do more – I have some advice.

Focus

Work on one project at a time. Work on one task at a time. You probably have a list of 50 different ideas you’d like to work on. And another 10 or so rattling around inside your head. It can be tempting to jump from one task to the next, particularly when things get hard or boring. Resist the temptation. The more you focus on a single task, the faster you’ll get it done.

Set a deadline

Release to the App Store in April. Put the sales page up by the end of June. One blog post, every week. No matter what. Set an ambitious deadline. If it feels like you won’t make it, cut scope. Then cut it again. A deadline is a little promise we make to ourselves. And it feels like shit when we break that promise. Wanting to avoid that feeling helps me get stuff out the door. 

Schedule it

The idea that you’ll magically “find” the time to work on your side project is silly. Between your day job, friends, family, and just plain ol’ crap-hitting-the-fan moments, life has a way of eating up every spare second. By scheduling time for your side project – in your calendar, along with all your other commitments – you protect it from being overrun by something else. Even if it’s just 15 minutes on Saturday morning.

Most of my productivity advice is pretty boring. Focus on one thing at a time. Set deadlines. Have a schedule. I don’t mean to undersell passion or excitement – those are important too. But, in my experience, what ships side projects is time, dedication, and a little bit of practice each day.

Be boring in your life, so you may be fearless in your work.

Until next time,

–Brian


Shipping Is a Muscle

I used to be terrible at shipping side projects. It always started the same way: I’d have an idea, get a head full of steam, and plow right into making it a reality. My fingers would fly across the keyboard, code flowing from my brain to the editor with ease. But, often, things would fall apart. I’d get bored or hit a technical roadblock and the project would end up languishing on my hard drive.

I used to be terrible at shipping side projects.

It always started the same way: I’d have an idea, get a head full of steam, and plow right into making it a reality. My fingers would fly across the keyboard, code flowing from my brain to the editor with ease. But, often, things would fall apart. I’d get bored or hit a technical roadblock and the project would end up languishing on my hard drive. I’d move on to my next brilliant idea, hoping that would be the one I’d actually ship.

You can guess how well that worked out. Sound familiar?

On your first trip to the gym you might struggle to lift even the smallest of weights. Your muscles, twitching and quivering, haven’t been trained for what you’re asking of them. But, with a little persistence and dedicated practice, you start lifting a bit more. Then a bit more on top of that. One day, you surprise yourself with how strong you’ve become.

Shipping is a muscle. And, like any muscle, it can be trained. Here’s some tips to make it a bit easier:

1. Cut scope

When you have a day job, particularly if it’s one you enjoy, your first responsibility is to your employer. Which means the majority of your side project work has to happen on nights and weekends. You need to make sure it’s manageable — and the best way to do that is to aggressively cut the scope of your project.

For every potential feature ask yourself two questions:

Be honest with yourself!

  • Is this just a nice-to-have, and not really core to the product?
  • Is this something that can be added or improved upon later? (More on this in a second)

If the answer to either of those questions is yes, leave it out of your first version.

2. Iterate. Iterate. Iterate.

You can always improve your side project — particularly once you have feedback from real users. You need to adopt the mentality that until an idea is out of your head and into the hands of other people, it basically doesn’t exist.

When I launched Draftly, my Dribbble client for Apple TV, it let you do three things: see a collection of shots, see a bigger version of an individual shot with some details, and view a user’s profile. That’s it. But in the weeks after launch I added more features, refined the UI, and refactored the codebase. If I had waited until everything was “perfect”, I might never have launched at all.

Perfect is procrastination.

3. Stop wasting time

It’s a cliche, but it’s true: we all have the same 24 hours each day. It all comes down to priorities. Stop watching Game of Thrones. Or watch it while working, at least. But you’d get a lot more done if you didn’t.

Try to value creation over consumption. Instead of watching television, write a blog post. Rather than scrolling through Twitter or Facebook on a long bus ride, fire up the Notes app and brainstorm project ideas.

Granted, some items on your calendar are immutable. If your kids need to get to daycare, you can’t skip the drive and put in an extra hour on your side project. But if you examine your schedule closely, and aggressively cut scope, I’m betting you’ll find ways to eke out time here and there.

Work that muscle

With some practice and these tips, you’ll be well on your way to becoming a shipping machine. Why not start today?


Side Projects + Open Data

Working on side projects is an important part of any developer’s career. You can learn new skills, team up with others in your field, and practice promoting your work. In a job interview, talking about a side project you’re excited about is often more effective than showing off a portfolio full of school projects or client work. It shows you’re passionate and eager to learn — particularly if you’re a junior developer.

Working on side projects is an important part of any developer’s career. You can learn new skills, team up with others in your field, and practice promoting your work. In a job interview, talking about a side project you’re excited about is often more effective than showing off a portfolio full of school projects or client work. It shows you’re passionate and eager to learn — particularly if you’re a junior developer. But we’re all busy, and it isn’t easy to find the time to plan, develop, and promote a side project. I want to share one of the shortcuts I use for side project concepts: Open Data.

Open Data is the idea that data — particularly government data — should be freely available for anyone to use, remix, and republish. Many governments have bought into the idea. Toronto, for example, maintains a repository of data sets in its Open Data Portal.

Governments often don’t do a good job of utilizing or presenting the data they have. When looking at a data set, I ask myself two questions:

  • Can I improve access to this data, or make it easier for the average person to browse?
  • Can this data be useful when paired with the technologies uniquely available on mobile devices? (GPS, Health tracking, etc.)

You could use the Parking Tickets data set to power an app that warns drivers when they park somewhere that is ticketed heavily.

You could create an app that monitors the user’s route to work and, using the Road Restrictions data set, warn them about accidents and construction. Heck, throw the Traffic Cameras set in there and you could let them see how bad traffic is for themselves.

You could combine Heat Alerts and Extreme Heat Alerts with Air Conditioned Public Places & Cooling Centres to alert those vulnerable to high temperatures and direct them somewhere they can cool down.

The ideas are endless.

When Toronto released the results of the Core Service Review (a fancy survey, basically) browsing the responses, well, sucked. It was a fantastic opportunity for me to create What Toronto Said, a site where every response could be browsed, mapped, and read easily. It was my first foray into Ruby on Rails, which meant it wasn’t just an opportunity to make things a bit easier for my fellow Torontonians, it was a chance to improve my skills.

And not just my technical skills. As Austin Kleon points out, your work doesn’t speak for itself.

“Our work doesn’t speak for itself. People want to know where things came from, how they were made, and who made them. The stories you tell have emotional significance and bring value to your work. Everyone wants to feel connected, and stories make things more personal.”

Once the site was ready, I contacted a few local media outlets and let them know it was coming. I ended up doing a few interviews, appeared on the radio, and got traffic from a bunch of local blogs. It was so much fun. Not to mention, jumping into Rails on my own helped me land my gig at The Working Group.

Learning to ship, improve, and promote your work doesn’t come naturally to most people — myself included. It’s a skill, like anything else. And that means you can work to improve it.

Side projects are a great way to practice all your skills. And with the insane amount of Open Data out there, it would be silly to pass it up. Instead of working on yet another todo list app, why not create something that allows you to up your game and help out your neighbours, all at once?

Everybody wins.