DEV Community: Filipe Silva

8 Actionable Strategies to Give an Extra Boost to Your Side Projects

Filipe Silva — Sat, 30 Jan 2021 17:14:30 +0000

Software developers don't agree on a lot of things. You have infinite fertile ground for debate around programming languages, IDEs, frameworks, operative systems, libraries, patterns, best practices, or counter variable names. What we all agree on is that we hate wasting time on some piece of code that will not bring any measurable benefit, or worse, it will be deleted in 2 weeks. With experience, we become pretty good at sniffing that out from a distance, and, it's our responsibility to always steer the work we do into meaningful territory.

When we tackle our programming side projects we tend to have a higher degree of control than when developing software for others, and since I believe no programmer ever started a side project with the idea to get the least out of it as possible, I'm going on a limb here and say that, even if only deep down, we always have great ambitions for the software we craft.

We always want to get the most out of side projects we build. Even finish them, if we allow ourselves to go a little crazy.

This is part three, of my Side Projects Trilogy. In part one, I talked about How to Choose your Next Side Project, so that chances of getting the best out of them mount on your favor. In part two, I listed 12 Great Ideas for Programming Projects That People Will Use. And here, I'll be sharing my favorite strategies to make your side project journeys as enriching as possible.

Find a partner

“If you want to go fast, go alone. If you want to go far, go together.” - African Proverb

Working with a partner might not be the best solution for all projects and everyone. However, there's always a time where I wished I could brainstorm with someone as invested in the problem as me. Asking for help in a forum or Twitter wouldn't have the same impact. A partner would mean fewer blind spots, and fewer surprises sneaking up on you.

Your ideas get more chances to be refined into something great. Your tech stack knowledge hopefully is not a complete overlap, opening doors to leverage the best languages and frameworks for each type of problem.

The best thing about working with a partner is not tech-related though. There will be moments when life outside happens. When it will be difficult to keep advancing, where there won't even be a clear path to progress to. When one's output into the project suffers, the other can use that as motivation to keep going, knowing that a switch in roles will probably happen in the future.

The rule of thirds

“Hell, there are no rules here - we're trying to accomplish something.” - Thomas Edison

Named after the most famous photography cheat code, this is a framework to help you chose the most engaging tech stack for your project. You get the best technologies to get the work done, but with a little spice to keep things interesting.

Pick 3 main technologies for your project according to the following characteristics:

One where you consider yourself an expert
One you have been experiment with
One new to you

This distribution provides some benefits, even adds some fun to the experience. First, as software developers, we are always experimenting or wanting to. This allows us to accommodate that while mixing in other technologies where our expertise level guarantees us some reasonable level of productivity from the get-go. Also, the importance of including another technology we have been experimenting with can help us complete the picture on it, letting us know it's a tool we want to keep on our arsenal or not.

Second, this is also a way to escape the boring. When you are stuck or tired of working with one, perhaps you also use it on your daily job, you can jump into any of the other two.

Know your purpose

“Never doubt that a small group of thoughtful, committed, citizens can change the world. Indeed, it is the only thing that ever has.” - Margaret Mead

This is the platform that supports any success of our side projects. The more you know why you are doing it, the easier it will be to weather all the challenges. When things get hard, it's the quality of the picture in your head of your purpose that will keep you on your path. No solid foundation, no inner reason moving you, and abandoning the journey will be the most likely outcome.

Know why you are building a side project before knowing how or what.

Try some daily affirmations and surprise yourself. Open your note-taking app every morning and write in detail why are you working on the current side project. Do this every day and don't check previous entries. After 2 weeks, check all the notes and compare them. When you zeroed in on the same entry every single time you'll notice the difference.

Small milestones into big targets

“The process of delving into the black abyss is to me the keenest form of fascination.” - H. P. Lovecraft

The pursuit of a goal gives meaning to what we do. The pursuit, not necessarily the goal. Those goals we set for ourselves can be more or less within our reach and in that balance lies some of the reasons for success in side projects.

Set small milestones along the way in your project. Group a few features, and as long as you can release them alone while still adding value you are good to go. This gives you room to breathe. You can stop at any time you want, and chances are your project is stable and doing what it's supposed to do.

Several milestones strung together can lead you into your target objective. Make this target as big as possible, allowing for deviations along the way. You might experience technological impediments, obtain new user feedback, get improved designs, etc. Some features might disappear or be developed from scratch and it will be decisive how you handle the difference between what you envision in the beginning and what you might be getting a few weeks, or months, down the line.

In darkness, deploy motivators

“We are all in the gutter, but some of us are looking at the stars.” - Oscar Wilde

I already mentioned sometimes in this article how predictable dark times are when tackling a side project. You probably know what I'm talking about. We know they will come and so better be prepared for them. Most of the ideas I explain here are already preventive medicine for this problem, however, it's only appropriate if we reserve a special Big Gun for a special Big Boss.

When I feel less motivated to start, or continue, a project there are two kinds of motivators I call upfront. Podcasts and communities of other makers.

Hearing the struggles other founders go through when working on their products from podcasts like The Indie Hackers Podcast, or How I Built This with Guy Raz has always the positive effect of getting me pumped to pick up where I left off.

Communities like Indie Hackers, Product Hunt, or Starter Story, work differently. They make me realize that different products, more or less original, with different degrees of polish, target users, and technologies employed can enjoy the same level of success.

Place rewards on your roadmap and reap them

“Don't judge each day by the harvest you reap but by the seeds that you plant.” - Robert Louis Stevenson

I already mentioned milestones and here I want to emphasize the impact of rewards. Maybe you set a reward for each completed milestone, maybe for two or three milestones completed before X days. The rule is not as important as the object. It's really powerful when I can see that behind those small goals I'll get something that I won't have in any other way.

Be careful though with feedback loops. You don't want to set milestones with random features just so you can eat those extra fries. And rewards don't always have to be things. Maybe it's only more time to binge on a TV show. Use rewards wisely, but use them, and most importantly, go all the way in taking advantage of them.

Stop when you feel unstoppable

Wait, wait, not that kind of "quitting" stop. I'm talking about the Hemingway "stop".

“Always to stop when you are going good and when you know what will happen next. If you do that every day when you are writing a novel you will never be stuck. That is the most valuable thing I can tell you so try to remember it.” - Ernest Hemingway

This magnificent advice from Ernest Hemingway applies to writing as it applies to programming. Both are creative endeavors, where fluctuating levels of inspiration are to be expected. Sometimes is not where you want it, others you don't know what to do with so much of it.

Inspiration is not always unpredictable though. We can create the best conditions for it. A white screen with a cursor blinking is probably not it. Getting in the office and face a piece of code that doesn't even compile is, you guessed it, probably not it. On the other hand, the moments where you are in total flow are just as powerful, everything feels like magic coming out of your fingers.

I'm not saying to waste that precious, most productive, section of your schedule and stop it short. What you can do is aim for a finish when an interesting development is going to happen next; when you already know what you'll do and how it will play out. This works best if you don't have a fixed schedule, of course.

If you have a tidy time slot where to play inside, maybe it's time to use the rule of thirds: stop when it becomes clear what will happen next with one of the technologies. If you still have 40 minutes available, jump into another area of your project and get to a cliffhanger development there.

Do it in public

“I am always doing that which I cannot do, in order that I may learn how to do it.” - Pablo Picasso

One of my favorite reasons to build side projects is to Learn. Learning anything related to shipping a software product and have it being used (preferably by not just you), of course. With the growing trend of learning in public, describing the lessons you are going through while developing software is not just a way of increasing your accountability (people start expecting content from you) and authority (people start recognizing you as competent in the topic).

There's another layer of learning we can aim for. Learning guru, Scott Young, came up with a different style of project: a benchmark project.

Instead of going deep into some new web framework, seeing all the videos, reading all the tutorials and doing all the sample projects, which might feel good and provide us with a sense of nice practice, we should start by defining a clear benchmark that defines success.

Notice the difference between a clear benchmark like "Make 10 contributions to open source projects using the web framework X" and "Learn how to use web framework X".

Which one is propelling you further into action?

You can't hide inside 'tutorial zone' and pass it as learning with a benchmark like that. They work like quests on RPGs. You have to put in the work into something that will be measurable and impactful for others. There's only a better version of you on the other side of that quest.

Wrap up

We sometimes get lost along the way in our side projects. We lose sight of what made us start in the first place. We may even reach the destination we set for ourselves, but because it doesn't look like a finish line, with fanfare, confetti, and excitement, we stall or wander in the 80% that produces 20% of the results.

That is not the way it's supposed to be. Your side project is finished when you got the most out of it, and not necessarily at the finish line. These 8 strategies aim to help you get more out of the projects you start, and if that makes you faster to the finish line or the route more scenic I would say that is awesome. Give them a try, see what works for you, and let me know about it. Enjoy the views.

12 Great Ideas for Programming Projects That People Will Use

Filipe Silva — Mon, 25 Jan 2021 22:21:03 +0000

This is a dangerous article for you to read. There's a real chance that nothing good will come out of it once you are finished. This is a half-decent list of side project ideas, and like many times before this, you will be offered a choice at the end.

Will you start one or not?

Did more choices make you more confused? That will make it harder to start. You decided on one, but don't see how you can do it? That will make it harder to start. You are working on one already, and want to abandon it, so you can start another? That will make it harder to finish what you started. You got another proof of how many people have cool side projects out there while you don't? That is Fear Of Missing Out®©™, and you guessed it, it can depress the best of us and will make it harder to start.

Like I said, a chance of nothing good, but just a chance. Because there's also a chance of nothing terrible. A chance of you finishing this article and immediately create a git repository with one of these ideas as the title. A chance where you begin a journey of learning, fun, solving needs, and maybe even profit.

This is part 2, of my Side Projects Trilogy. On part 1, I talked about How to Choose your Next Side Project, so that chances of getting the best out of your side project mount on your favor.

Without further ado, here's a collection of hand-picked side project ideas, inspired by other articles before this, my experience, and what I've been reflecting on what makes a great programming project idea.

Digest of favorite twitter accounts

Most social media platforms have two things in common:

an algorithm to show you what they think you want to see
they have posts that you actually want to see buried beneath uninteresting content

Why not transform the contributions of your top Twitter accounts into a daily/weekly digest? This way you guarantee that you'll never lose those insightful posts, with the bonus it's you that decide when you will get to them. Maybe you can take the next step and send it automatically to your email. Or let other users curate and share their lists. Twitter is just an example, you can do it for Instagram, Facebook, or even the top posts of your favorite subreddits.

Backend skills: ⭐⭐⭐

Frontend skills: ⭐⭐

Ops skills: ⭐⭐⭐

Complexity: 🤯🤯🤯

Profitability chances: 💳💳

Inspiration: Mailbrew

Portfolio website

A project with compound interest. You will get the benefits during and after its finished. As a programmer you get to hone your frontend skills, maybe try a new CSS or JS framework. You can use a template, or try your hand in design and put your personality into it. Once done, it's your own place on the Internet, to show what you are up to, what's interesting in the world, how you can help people and organizations. You will even have a special place to display your side projects!

One of my favorite things about this idea is how incremental it can be. Go ahead, create a landing page and deploy it somewhere. It's live and it already counts. Next week add a "Start Here", in a month maybe your resume, and whenever you finish another side project you can open that gallery I just mentioned. As I said, it keeps getting better and better.

Backend skills: ⭐⭐

Frontend skills: ⭐⭐⭐

Ops skills: ⭐

Complexity: 🤯

Profitability chances: 💳

Inspiration: Nat Eliason, Devon Stank, Steph Smith, Dan Vega, or even my own (in case you are curious what a little bit of inspiration can do).

Weather app

Everyone has a favorite weather app. The one that you will build will have your unique touch and, I'm willing to bet, will be the favorite of someone else. The weather data is widely available in several APIs, but I think the secret here will be how you chose to present it; it's where you will make the biggest difference.

You can make it a mobile app or just a web app, depending on your objectives, but I would say that part of the challenge would be to, independently how you choose to start, leave the door open for growing in one of those directions.

Backend skills: ⭐⭐⭐

Frontend skills: ⭐⭐⭐⭐⭐

Ops skills: ⭐⭐

Complexity: 🤯🤯🤯

Profitability chances: 💳💳💳

Inspiration: Overdrop Weather, Today Weather, Windy

Automate something

What in 2021 still requires your manual intervention? No matter your programming skills there's an automation that you can build to match your skills and present you with a worthy challenge. Take inspiration in Al Sweigart's, fabulous, Automate the Boring Stuff with Python. Pick one chapter that interests you the most, either in theme or because you are messing with related technologies and complete one of the projects at the end of it.

Set a text message alert for when something on your wishlist gets a discount. Automatically back up your knowledge base. Generate the most common file structure of your projects from a single command. Track your favorite writers and automatically add their new articles to your reading list. I think you will come up with better ideas than these, but the principle is simple, find something that takes you time, and have a machine do it.

Backend skills: ⭐⭐⭐

Frontend skills: ⭐

Ops skills: ⭐⭐⭐

Complexity: 🤯🤯

Profitability chances: 💳💳💳

Inspiration: How I Eat For Free in NYC Using Python, Automation, Artificial Intelligence, and Instagram

Twitter bot

Like the "digest" idea, this can be applied to a majority of social networks where valuable contributions can earn you Internet points. Apply for a Twitter developer account, roam through Twitter API, find the endpoint that allows you to send tweets and hook that up to a list of interesting facts, quotes or Anthony Jeselnik jokes.

There's the reactive kind of bots too. When it's mentioned or certain words are tweeted, your bot can jump in and provide something useful to whoever tweeted in the first place. Maybe you can do one of each kind and have them compete in popularity.

Backend skills: ⭐⭐

Frontend skills: ⭐

Ops skills: ⭐⭐⭐⭐

Complexity: 🤯🤯

Profitability chances: 💳

Inspiration: Nassim Nicholas Taleb Bot (active bot), Thread Reader App (reactive bot)

Niche job board

This is your way to help companies connect with job candidates in fields that maybe are not well covered by existing job boards. Focusing on a niche will provide two benefits for this side project:

Reducing the scope of the domain you are serving
Easier to identify and understand potential customers for your product.

Another aspect of this idea, more than any other in this list, is how you will have to handle two different personas using your product: recruiters, and candidates. This will make for some interesting challenges on UX design, and, for example, on the backend on how you decide to manage different roles and permissions.

I also like this one for how clear it can be monetized. I'm not saying it will be easy, but the path seems more obvious than in most.

Backend skills: ⭐⭐⭐

Frontend skills: ⭐⭐⭐⭐

Ops skills: ⭐⭐

Complexity: 🤯🤯🤯

Profitability chances: 💳💳💳

Inspiration: Key Values, A Digital Accessibility Job Board, idealist

Quiz game about a favorite topic

This is the first of two game-related ideas on this list. Who doesn't like to test his trivia skills? Yeah, you probably know a guy who doesn't, but everyone else still has loads of fun with this kind of game. Again, I encourage you to focus on a niche. It will be easier to find questions + answers and find the public for the topic you chose.

You will also have other kinds of decisions to make, not present in other ideas that I suggest. If you want to deal with single and/or multiplayer, with sync or async play. What about rewards? How to manage a leaderboard and ways to keeps questions fresh. Possibilities are endless, don't let them drown you.

Backend skills: ⭐⭐⭐

Frontend skills: ⭐⭐⭐⭐

Ops skills: ⭐⭐

Complexity: 🤯🤯🤯

Profitability chances: 💳💳

Inspiration: Quiz game for Android (GitHub)

Deal finder

I have a special feeling for this kind of product. My latest side project, Win-Win was just that. I love board games and finding good deals on them. I hooked up to Boardgamegeek API, and now I can fetch all prices for the games I'm interested in. Then it just simple math, and finding items that are way below the average price. The feeling of pouncing on a game that is 70% below the median price, minutes after being posted, is incredible. The hope that others would think the same was what motivated me the most.

Think about other marketplaces that you use or types of products that are accessible with APIs and work with those. Even without complex math, you can compare items of the same type for the biggest discount or the lowest price per unit.

Backend skills: ⭐⭐⭐⭐

Frontend skills: ⭐⭐

Ops skills: ⭐⭐

Complexity: 🤯🤯🤯

Profitability chances: 💳💳💳💳💳

Inspiration: UnitPrice.org, diskprices.com, Scott's Cheap Flights

Recommendation system

When was the last time you had to choose between alternatives in a domain you are not an expert? Like last time you were at that favorite hobby store, of your significant other, that you know nothing about? Yup, we've all been there.

Focus on one domain, identify what are the meaningful items that you can recommend, and then start with a basic rule that returns some of those items based on an input. Later you can evolve your system to order recommendations, accept different types of input, or even let users inform your model based on the success of the recommendation.

Backend skills: ⭐⭐⭐⭐⭐

Frontend skills: ⭐⭐⭐

Ops skills: ⭐⭐

Complexity: 🤯🤯🤯🤯🤯

Profitability chances: 💳💳💳

Inspiration: Recommend.Games, Movie Recommendation System (GitHub)

Gamified habit tracker

The habit tracker is a regular in these articles. Only surpassed by the todo app and the chat app, which as we all know, are required by law to make an appearance in all lists. Check and check.

Here you give it an extra twist, with features like:

Give perks and achievements to streaks completed.
Unlock app features as streaks increase.
Create a Battle Royale style competition, with all users who want to do X (read 20 pages a day for example), until only one remains.
Create quests where users must follow a given habit formation process

Our app must provide a layer of incentives on top of all others our users might already have for adopting their new habits. This is what will separate it from the majority of all other habit trackers.

Backend skills: ⭐⭐⭐

Frontend skills: ⭐⭐⭐⭐

Ops skills: ⭐⭐

Complexity: 🤯🤯🤯

Profitability chances: 💳💳💳

Inspiration: Habitica

"Clone" one of your most used apps BUT add the one thing you miss the most

I'm not suggesting to commit some kind of trademark violation or be just another copycat with no soul. The thing you add to your solution must be enough to make it unique and worth existing by itself. Don't just clone a Kanban board and have it play the "Eye Of The Tiger" every time you pick a new...wait. That's an awesome idea!

Now, seriously, you probably have some 5 or 10 things that drive you crazy in your favorite/most used apps. Make that feature the reason of being of your project. If the pain is big enough to create a new project because of it, it will also make you the right person to understand what should be done about it.

Don't forget to peer into the support forums, subreddits, and Twitter of these products. These are places where suggestions, pains and feature requests are most abundant. Someone can provide that first spark you need, someone, probably, willing to pay for it.

Backend skills: ⭐⭐⭐⭐

Frontend skills: ⭐⭐⭐⭐

Ops skills: ⭐⭐⭐

Complexity: 🤯🤯🤯🤯

Profitability chances: 💳💳💳

Inspiration: This one is on you 😄

Choose Your Own Adventure game

This is a fantastic idea if you also want to exercise your writer's muscles. Dream of a story, don't let the stereotypes of fantasy genre limit you for this type of game and be prepared to throw everything at the player. The player will throw everything at you in return, so be sure to sanitize those inputs. Will you allow just commands through pressed keys, words, or full-blown text? Again, different levels of challenges and technologies to put into place. How will you store the text for the events? Will it have any kind of art?

For the player, will you be able to personalize its attributes? Will those attributes affect the game or just serve cosmetic effects? What about using the same character between games? Or share it with other players?

Backend skills: ⭐⭐⭐⭐⭐

Frontend skills: ⭐⭐⭐

Ops skills: ⭐⭐

Complexity: 🤯🤯🤯🤯

Profitability chances: 💳

Inspiration: A Dark Room, Magium

Wrap up

I want to start by clarifying the ratings I gave to each idea. Even though they are subjective to my experiences as a developer and how I imagined the final result, I tried to make them more of a metric of comparison between ideas. A complexity level of 🤯🤯🤯 only means the project should be of middle complexity considering all ideas in this article.

With that out of the way, I sure hope you don't take the fact that these are 12 ideas and build one each month of the year. That would be crazy. And awesome. Not sure if more awesome than crazy, but, definitely worthy of my admiration. Even if you just start one of these it would make my day to hear about it.

So, I challenge you again. Will you start one?

“Whatever you can do or dream you can, begin it; Boldness has genius, power and magic in it.” - Johann Goethe

Take that first, tiny, step. You are more than ready.

How to Choose your Next Side Project

Filipe Silva — Sat, 27 Jun 2020 11:36:42 +0000

If you are reading this article, I'm willing to bet you have also read your fair share of "side project ideas" posts. I also love going through those, curious as I am, in search of some magical spark, some rabbit hole to lose myself with abandon for a couple of months.

Well, this is not that kind of post. Not in isolation, at least. This will be a trilogy of articles about side projects and rest assured, I will also publish a list of project ideas as part II.

And on part III, we will conclude this trilogy with a collection of tips and strategies to increase your chances of getting the most out of your side projects.

The weird thing about those lists is this feeling that for each article written about fun projects, the more pressure we face to always be working on one. If that was not enough, I have to admit, they also induce some kind of analysis-paralysis. All projects have different pros and cons, technologies and degrees of challenge, which can make the first step, picking one idea and starting to work on it, almost impossible

I have been thinking about this problem, and I'm going to propose a few guidelines to help you decide on what you are going to have fun, developing, next. There are so many of us with skills to create something meaningful, that even if I get one person to get unstuck it would be already a big win for me.

So, fasten your seat belts, and come with me.

Why do you want to build a side project?

Investigate your Why. Ask yourself the question and don't stop on the first answer. Ask again why is that. This is not to discourage you if you don't like soul searching, or because you think you might find reasons that will make it even harder to get started.

The clearer you can make the reason why you want to start working on a new project, the easier it will be to make all the decisions leading you through it. Starting with, you guessed it, picking the right idea from all the ones in articles like this or those bouncing around in your head.

Let's look at an example, shall we?

“I want to build a side project because I want to experiment with some technologies”.

“Why do you want to experiment some technologies?”

“Because I see an increasing number of people talking about them and I want to see what they are all about”.

“Why do you want to see what they are all about?”

“Because I want to check if they could make my job easier”.

“Why do you want to check if they could make your job easier?”

“Dude, seriously?!”

Alright, that was a piece of dialogue that won't win any Nobel Prize. Let's imagine though, we reveal our why to be "I want to create a side project so that I can check if these technologies can make my job easier". We can use it to give us some perspective. We know what we do at our jobs, the kinds of problems we solve, some nagging constraints even.

If you are currently building some microservices backend for an online shop, and you want to start a side project to explore some technologies to help you with it, I would say the benefits of developing a recommendation service, or a weather app, are much more aligned to your purpose than another to-do app or a twitter bot. Notice I'm not saying those are bad side projects ideas, but only there are better alternatives to what you are looking for.

This is the great thing about figuring your why first. It narrows your choices, making clear what are the best options available.

My favorite reasons to start a side project

It helps to have a clear purpose to start something. That is clear. Which doesn't mean there will be only one reason why you would start that side project. If more than one reason converges into the same idea, I would say your chances of having a winner increased.

The list below is a non-exhaustive compilation of reasons I look for when evaluating if a side project idea has the potential to fulfill the purpose I establish for it. Use them to decide your next project if you see yourself in them.

I will learn something from it

The challenge, today, is almost not learn something when you develop a new piece of software. Even if you just turn on the auto-pilot and produce the same looking web page for the 40th time you will probably learn a new shortcut that will be part of your workflow from then on.

Being a new web framework, a new language, a new best practice, a new way to integrate existing tools, every day there is something new that can interest you and can provide a starting point to build something with it. Bonus points if you challenge yourself to step a little bit outside of your comfort zone. My advice is to never consider yourself incomplete, or missing out if you are not touching all bases. You can't learn everything, but you can always be learning something. That's the advantage of starting a project with this purpose in mind.

I will use what I built afterward

Building something you know you will use is awesome motivation. You will be after something you need, and it will be harder to stop you until you are done. Better yet, if it's something you need, there are probably others like you, who will gladly use what you come up with.

This can be one of the best filters of side project ideas. It becomes easy to exclude all project ideas that you already see you won't use or those for which you are already using a great product with the same features. Don't throw, what you think is, an interesting project idea just because you don't see a use for it, though. Others might find it the solution to their problems. Take into account you might be the only one using your project in the end, and so don't tie the value of what is supposed to be a fun experience into having others using it as well.

I estimate a short-medium completion time

A short-medium completion time is something between a weekend and two months. I would choose a side project idea based on this criteria because I don't know the future, if I will be having fun throughout the journey, or if I'm getting out of the project what I intended. So, to avoid spending too much time on something that is not going where I want I limit that time frame from the start. This would be harder to do if I started working on something that won't see the light of the day for six months, or a year. By that time, if I'm far away from my intended destination I might have lost six months, which hurts much more than one.

Reduce the size of the bets you make. It's your time on the line, it's the opportunity to be having more fun, learning something more interesting that you are not taking because you might be holding on to something for six months before any results. If your two-month project is complete, great! Time to review and assess if you have want to double down on it or start a new one, but independently of what you decide, you know you gave it your best shot and if there are any losses they won't be critical.

I see value in it even if I will be the only one using it

This one is related to "I will use it afterward". Maybe "warning" is too strong of a word, but I would say we should avoid deciding to start a side project based on the bet that others will have to use it as well for it to be successful. You are the only person you can count will use what you will build. So, if you want to go ahead and build a social network be prepared for the moment where you are the only one there. If you build a job board, be prepared to have zero jobs posted.

There's always a moment in every product where you are the only one using it, but if you are looking to start a side project this is a filter that might come in handy. If you want to have lots of other people using what you will be developing I would steer to a group of side projects ideas, and if you don't care if any people use it in the end, then I would consider another group entirely.

I want a new source of income

Like the previous point, this reason is something you can start from, but that you can't guarantee the payoff will be there for you after you finish. Unless you have people already paying you before you start, that's the picture. This shouldn't discourage you from starting a side project with this reason behind it. Survivorship bias or not, the examples of people that started with the same intention, and built profitable businesses are of it, are many.

It's also possible to filter your list of ideas with this reason in mind. You can investigate similar solutions to the ideas you have, by checking their 'pricing' sections on their websites, looking for public MRR reports, the number of paying users, etc. Find whatever you can get that lets you know if people are running successful businesses out of similar ideas to the ones you are looking into. This will let filter out many ideas where you don't see obvious signs of money being exchanged in the amount you are looking for.

I can't shake the idea out of my head

This is a special reason to start a side project. It works on many levels. If you look at list after list of ideas and there's this one you can't forget about, that's the one you should start. If you want to start a side project where every reason I listed until now doesn't apply, but you still can't let it go, well, the decision is made, and you should throw everything at it. This is a powerful reason to start something. On a deeper level of your subconscious, you are already convinced.

You should know yourself enough to tell if this happens all the time, where you could be just chasing a new shiny object, maybe even quitting the side project you are working on, to replace it with this new idea. Try to at least giving it a few days, see if you still want to start it then. Or if you are in the middle of another project, with a reasonable estimated completion time, why not finish that first, and if this new idea is that meaningful, you can build it afterward.

On side projects, default to start

This is apparently against what I just wrote throughout the article, but the strongest reason to start something will always be because you want it. If nothing else, start something and see where that takes you. You can always, with more or less difficulty, change course or start a new journey.

Looking in retrospect at my last side project, Win-Win, I can see in it all reasons I listed but one, as fueling my motivation, giving me a purpose. I didn't start with the idea of having a new source of income (it's still not very clear how to do that if you are bargain finding in the used board games market), but I was checking all the other boxes. I was putting into practice a new language I was learning and doing all the frontend development (being a backend developer ). I'm still using it almost every day since I launched it. I completed it in roughly two months. Its value is independent of having others using it. And, yes, I couldn't get the idea out of head until I finished developing it.

Next time you are looking for side project ideas, try to find first the reasons why you want to start it, so you can better decide what and how. We know ideas are everywhere and the means to bring them to reality were never so accessible as today. We know the execution of those ideas is what counts. If our chances of success increase 1% just because we work on something that aligns with our purpose, isn't that time well spent? Isn't that reflection worth it if it gets us a little bit further in our path to a successful side project?

Originally published at filipesilva.me
(Cover photo is by Victoriano Izquierdo on Unsplash)

For Something Special, Optimize Your Team for Harmony

Filipe Silva — Wed, 18 Mar 2020 21:22:16 +0000

A few weeks ago, I was on a 1-on-1 with my manager and he asked me a simple question: "How is the team?". At first, a simple question would mean a simple answer. There was a clear intention to compare impressions taken from another level in the organization and I appreciate that. The answer at first was indeed simple, but then System 2 took over.

Talking with Your Manager, Fast and Slow

In the omnipresent tome of wisdom that is Daniel Kahneman's Thinking, Fast and Slow, we are presented with two modes of thinking. Making my best effort to not murder with simplification the life's work of a Nobel laureate, it works like this: without noticing, we are either employing System 1, the fast talker, intuitive, sensitive and generator of impressions, or System 2, the calculating, careful, logic lover, and validator of impressions. System 1 is eager to help, System 2 is lazy. If you think this explains a lot about too many things, I know the feeling.

Now, let's do a quick exercise. We are both talking at work and I ask you the question "How is the team?". Quick now, think! What is your most immediate answer? Or, even more important, what are the gauges that you look at, in your imaginary team dashboard, that will inform your answer? If you are like me, you would, without a second thought, look at morale, followed by a close second, happiness.

That was System 1 talking and answering a very different question.

System 1 is so eager to help, so afraid to let us down, that it will do anything to get us a satisfactory answer. Including using a little trick called Intuitive Heuristic. When we are facing a difficult question, System 1 will answer an easier one instead. We don't even notice it most of the time. So, when our manager asks us "how is the team going?", we answer instead "how is the team morale?", or "is the team happy?". Which is much easier, right?

Morale and Happiness

I started answering with morale and happiness, but it's when you define those concepts that you might notice something is missing. For example, it was only after scratching the surface for a bit that I understood that I saw morale as a team property and happiness as a "player" property. It's also important to mention that morale and happiness could mean different things in another domain, but here I'm considering on purpose the specificity of the team environment, which could be in the workplace or sports.

What did I come up with?

Team morale is a shared feeling of how fair the results a team is getting considering how much effort is being put into them. I believe great team morale comes from conquering a great challenge, a true test to the team's mettle.

What about happiness?

Player happiness is how one feels about how much he's contributing to the success of the team times how much of his contributions to the team corresponds to what he does best. You probably have a different vision of happiness, but for me, it really peaks when I feel that I can impact the team with what I do best.

Having these two gauges on high levels is great. Rare as it might be, it's undeniable that work and results flow much easier when these two come together.

The Missing Link

I liked where I was heading, but at the same time I felt something was missing, something that tied together what was individual (happiness) with was of the team (morale).

Enter Football Manager. If you never heard of it, it's a simulator where you, surprise surprise, a football manager, take control of a club and try to lead it to glory. I gave it more hours of my life than I dare admit and I'm a football coach, in part, because of the damn game. Truth is, now I can appreciate the thought developers have put behind what makes a team successful and the variables that contribute to it.

Football Manager defines team harmony as the product of morale, happiness, and relationships.

It's so obvious now. Of course it's relationships. It's the first thing that exists in a team. It's what makes individuals more than the sum of the parts. It's the quality of the relationships that will make or break a team.

Relationships are with whom each person connects with inside the team, how strong each of those connections is, it's who gets the best, or worse, from whom.

It's even curious how people tend to gather around similar thinkers or who they most agree with, and not necessarily who gets the best out of them.

The Team Harmony Formula

It's through relationships inside the team, that one's happiness can impact team morale and vice versa. On a personal level, we can look at how the relationships of a person are affected by his mood, for example. A colleague with personal problems will interact differently than usual with other teammates, which might, in turn, affect the team mood. On a team level, personal happiness can be affected once involved in the dynamics of the team. Meetings that derail, conflicts that escalate, collaborations that go fantastic, office politics, are all instances of the group impacting the individual.

When asked how's my team, now I look at this triangle of morale, happiness, and relationships and I replace the question with a more interesting one: "how's the harmony in the team?". The answer, even if not as quick to provide, will be richer than what System 1 could come up with. Remember, you will be answering at least these:

How much do you feel team members are contributing to the success of the team
What's a rough percentage of tasks each team member has on what he/she does best
Who has strong relationships with whom
Who has poor relationships with whom
Who gets the best out of whom
How does the team evaluate the effort being put into challenges
How does the team evaluate the results obtained considering the effort they spent

Harmony is achieved when each person can contribute to the success of the team, against a real challenge, with their best skills, alongside people they appreciate to work with.

What Does This Mean for Managers?

When I challenged you to quickly answer "how is the team?", the first answer that came to your mind will tell you what are you optimizing for. If you see your team not getting the results you want, the behaviors you expect, or that the relationships are suffering, the first thing you will try to fix is the dimension provided by your quick answer. That's my bet at least, and that might not be the best course of action.

If you are looking for just one vertex as the problem, you are not seeing the triangle. I'm not even sure if there's only three, but the principle still stands, look at all the dimensions of the team and optimize for harmony, not the individual parts.

Look deeper into the strong suits that each member of the team can bring to the table, they might be hiding for lack of confidence, or because no one ever challenged them on that. Capitalize on the talents people enjoy employing that are most useful for the team.

What Does This Mean for Team Members?

Your control is limited. You have your actions and mindset. Your team members and leadership you can only aim to influence. There's value in being in the front lines though. Being first to recognize issues and problems as they come up is one of them, who is feeling unsatisfied, or undervalued. Where there is a gap in the skills inside of the team. How much more complex a given task ended up being. All these, and more, are triggers that will cause the team to lose its balance if not addressed in time and with the right toolset.

Optimizing for harmony is not hiding or minimizing problems. It's not running from confrontation, nor avoiding upset the status quo.

Optimizing for harmony is you stating the problem and gather support from your team to come up with solutions to solve it.

Optimizing for harmony is shining a light where you are hurting and help your leadership find the best resources to take care of it.

Optimizing for harmony can be counter-intuitive. It might mean doing the best job of your life while pissed at someone, simply because it's then the team needs you most. It might even mean doing the worst job of your life because you had to learn something new that made you uncomfortable, but since you were the best candidate of the ones available, you considered everything and optimized for harmony.

Parting Thoughts

Cover for your team. No matter what. Always be seeking where your team weaknesses are going to show and anticipate measures. Do a great job for your team and celebrate when others do the same.

Don't see harmony as a coagulant of behaviors, a standardization of opinions, or an ode to "we've always done it like this" BS.

Look at your team's harmony as a north star to help you consider your decisions. Time and the consequences of your options will make, or break, your team, but the way I see it, optimizing for people playing off each other's strengths, against worthy challenges, is a wonderful way to get everyone on the same boat, sailing to great results, and better versions of ourselves.