How to start a
Side Project

A free micro-book by Bibakis

About the book

Everyone should have a side project. It is a magic journey into entrepreneurship that opens up a new world of possibilities.

This guide will help you make the most of your time and increase your chances of success. It contains knowledge obtained from personal experience and also by monitoring many solopreneurs online. It is distilled knowledge from hundreds of people who succeeded and many others who failed.

If you have an idea you keep thinking about implementing or even if you don’t have one yet this guide is for you. It will walk you through all the steps you need to go through for your side project to be a success. We’ll discuss finding the right idea, validating it and then we’ll go over the many necessary details that make or break a project.

Table of contents

  1. Come up with an idea.
  2. Ask other people about their opinions.
  3. Validate your idea.
  4. Focus on what is important
  5. Start with what you know. Play to your strengths.
  6. Be passionate about it.
  7. Start small, stay small.
  8. Build something you'll use yourself.
  9. Show up every day.
  10. Frequently re-evaluate everything.
  11. Failure is an option.
  12. Goals help you succeed.
  13. Break large tasks into smaller ones.
  14. Don't get carried away.
  15. Avoid burnout.
  16. Consider a partner.
  17. Well known successful side projects.
  18. Epilogue.

1. Come up with an idea.

You may think it's hard to come up with an idea but it's actually the easiest part of a side hustle.

Don't think that you can only get an idea with a eureka moment. There are a number of tricks that can help you. This is what we'll discuss in this section.


First of all, if you are like most of us you have a list of "cool" domains which you've purchased over the years. For example I have registered domains about an app that organizes meetings, a wallpaper sharing website and many more.

So check out the list of your domains. Do you see anything that stands out and could be transformed into a successful app or service? It should be a concept that allows you to charge real money, preferably applicable to companies.

If you don't have purchased any domains or if your domains don't look strong enough, don't worry. Domains don't matter anymore. Nowadays people just use Google to find what they are looking for. Nobody types the actual domain in the browser anymore. Once you find your idea the domain can be a compound word. For example if your app is called SuperApp the domain can be or something similar.

Examine your workflow

Try to thoroughly examine your daily workflow for pain points. For example Stripe (the famous payments processor) identified the problem that creating a system to charge credit cards over the internet required developers to go through badly written documentation and archaic technology. They created a system that was very easy to implement and their customers loved it.

Every time you work on something that is hard to do you should examine the possibility of an app or service idea. It is very unlikely to be the only person having this problem. If you have it, chances are others are having it too.


Another thing you need to look out for is repetition. Are you constantly doing the same task multiple times a day (or week)? This is another possible opportunity. For example, at the start of the month I get multiple emails with invoices which I then save to a certain Dropbox folder in my computer. Once I collect and organize them by name and date, I forward them to my accountant.

Of course this process takes place only once per month so I'm not sure if I would pay for a tool that solves this problem. However it illustrates the concept of repetition. People are willing to pay for something that automates a repetitive workflow. The reason is that everybody wants to save time if possible.

For example Zapier created a platform that automates all kinds of things. It connects 3000 different apps to allow you to create automations for all kinds of tasks. For example you can automatically save email attachments to your dropbox and have it alert you on slack.


Not everything worth building starts with a problem though. Many times you can "Take a sad song and make it better" as the Beatles used to say. This applies to you especially if you have an interest or background in design.

A lot of existing products have a bad design or in general have an ill designed workflow. This is a chance to take an existing idea/product/concept and create an improved version. For example offers a better way to issue invoices which look more beautiful and more professional. created a better, smarter way to use email. They used innovative thinking to create features such as: the screener, decide if you want to be getting email from someone. The imbox, a place for your IMportant email. The feed, for reading newsletters and casual email.

In our examples people took existing concepts (invoices, email) and brought them to the modern age. The world is full of old concepts in need of a renovation. You think gmail is boring? Why not create a modern gmail client?

Ask people for problems they are facing.

If you still don't have any good ideas, turn to the people around you for inspiration. Ask your coworkers, friends and family about their problems. This opens you up to a new world view as people from other professions share their own views. This allows you to break free from the bubble of your limited perception.

It's important when asking for opinions to create an environment where people feel genuinely free to share their thoughts. The goal here is to gather information. Don't criticize their thoughts (yet). The time for idea validation will come later.

Steal an idea

Still can't get a great idea? Why not steal one? The concept is that it's ok to steal someone's idea but you still have to be unique. Take for example pizza restaurants. They copy each other's concepts but all of them try to differentiate.

The same model can be found in the software world as well. There are many weather apps and there are many todo apps. Sure some of them are more successful than others and some of them make no money at all. But isn't that the way things go in every business segment?

I'm not proposing that you create clones of things. However if you try to differentiate you can have a reason to exist (and succeed). Instead of the next generic todo app, try to make a todo app that integrates with a company's intranet, or one that integrates with email systems, or one that uses OCR to scan handwritten todos.

Instead of the next instagram, try a photo sharing site specifically for mobile wallpapers, or one for cat pictures. The list of variations of successful concepts is endless and the only limit is your imagination.

2. Ask other people about their opinions.

Our brain sometimes plays tricks on us. It's very common for somebody to be overly optimistic and overlook important details of a project idea. Don't get caught in a dream state where you go from zero to billionaire in your head.

Other people's opinions can be a reality check for your imagination. Reach out to friends, coworkers and family and ask their honest opinions about your business ideas. Do they think it'll work? Most importantly, would they buy your product or service?

At this point I suggest that you read an excellent book by Rob Fitzpatrick called "The mom test". It takes you through the process of gathering feedback and avoiding biased opinions. Written by an introvert who is bad at meetings, this book will give you the tools to talk to customers and learn what they really want.

More opinions mean more information. More information means more validation and more informed decisions. Just make sure to extract the right information from raw data (which in our case is people's opinions).

Be careful not to get caught in an "analysis paralysis" state. This is a state when overthinking and overanalyzing can cause decision making to halt. When you find yourself paralyzed, take a break, move away from the data for a bit and try to see the bigger picture.

Ignore the naysayers. People who reject an idea without arguments simply have a negative opinion. Don't make them doubt yourself and your ideas. You should be able to filter out negativity (for the sake of negativity) and keep only the opinions that bring you actionable data.

If possible, engage in conversations. Every person has a different logic and follows a different pattern in his head when it comes to validating an idea. A conversation gives you a wider perspective since it lights up many data points.

Don't try to project your opinions on people. Ask open ended questions where people are free to express themselves without having an opinion "extracted" from them. It's up to you to extract information from other persons' opinions. Remember you are the one who benefits from this process even when you don't like what you hear.

3. Validate your idea.

If you've spent lots of time using the methodologies in part 1, you should have quite a few nice ideas by now. However you can only really build one of them. So how do you select the best one of them?

SWOT analysis

The first thing you can do is a SWOT analysis. SWOT are the initials of the words: Strengths, Weaknesses, Opportunities, Threats. It is a strategic planning technique that you can use to evaluate ideas and projects. SWOT starts with creating a 2x2 matrix as you can see in the image below.

The four parts of SWOT as described in wikipedia are as follows:

SWOT assumes that strengths and weaknesses are frequently internal, while opportunities and threats are more commonly external.

Strengths: characteristics of the business or project that give it an advantage over others.

Weaknesses: characteristics that place the business or project at a disadvantage relative to others.

Opportunities: elements in the environment that the business or project could exploit to its advantage.

Threats: elements in the environment that could cause trouble for the business or project.

This matrix will give you a more complete picture of the overall attainability of the idea. So if you apply this analysis technique to every idea you will eventually end up with only a few.

Real world validation

When Zappos was created, it didn't own any inventory at first. They were making $2000 on orders every week but not making any profit. The reason was that every time an order was placed, the owner would buy the shoes from a local store and then ship them to the customer.

At first the goal was not to create a business but to validate the concept. It didn't matter if there was no stock and no warehouses, but if people were willing to buy shoes online.

Dropbox founder Drew Houston had created a prototype of the now famous file sync app. But it was full of bugs and far from perfect. So he created an explainer video and released it on Hacker News website back in 2007. This was before the app was ready. It served the same purpose as the Zappos example above. Validate the original idea.

Building a proof of concept

You may have heard the quote: "In theory, theory and practice are the same. In practice, they are not". Your idea, your assumptions, even your SWOT analysis, all that… That's the theory. But the business you want to create? That's practice.

The concept of idea validation is to put a little practice into our theory to see if it holds up in the real world. Doing so is very easy but it's much more important than what you realise right now. After all there may be benefits and knowledge in building something. But the rewards are huge if what you'll be building is also of interest to other people.

It's post Covid era so you can expect that people will find your idea online at first, even if it's an offline business. So the first step to idea validation is to create a website. It doesn't have to be professionally designed although it should be what we call "presentable".

If you have no idea how to create a website, start with a blank piece of paper. Put the main items in place, like a menu, some text and draw some pictures. This process is called wireframing. You can then turn this wireframe over to a professional designer to get something that looks like a full blown website.

The text in your website should describe your business and what your customer will be getting. The pictures are of less importance but it helps if they are pictures related to your product. Are you making an app? Put up a screenshot of your designs. Are you planning on selling something? Put up pictures of your products (even if you don't have them yet).

The most important part of your website is the CTA. It stands for Call To Action and it's the button that people will be clicking to request what your service offers. If you're making an app it should be a "Sign Up" button. If you are selling products it should be a "Buy Now" button.

Buy a domain name and some cheap hosting and upload your website online. Don't worry if you can't find a great domain at first. It's not important. Also don't worry if you can't find a .com domain but only a .net or .io or something else. It's also not important at this point.

Now with your website online it's time to drive some traffic to it. Make an account in Google or Facebook ads and set up a small budget. Something in the range of $100 to $500 depending on your abilities. Write some copy for your ad and hit publish.

Make it so you get an email when someone hits the CTA on your page. So after the campaign ends it's time to do the maths. How much hypothetical money did you make? Subtract the money you spent on advertising and you have an idea of the likelihood that your idea will be a successful business.

I know that perhaps you feel a little confused right now. How to buy a domain? How to connect it with web hosting? How do Google ads work? Unfortunately explaining these concepts is outside the scope of this article but I'll do my best to cover them in future posts. Until then Google is your friend!

4. Focus on what is important.

One of the skills you'll need for your side hustle to succeed is prioritization. The reason is that it is something you will do in hours outside of work. You would be lucky if you can allocate three to four hours a day, five days a week.

When your resources and your time are scarce you have to learn to prioritize. This means that you have to be careful about spending your money and resources and even more careful how you spend your time. Actually everyone should learn to prioritize anyway. Nobody ever has infinite resources.

Focus on the things that matter. Write down what the most important parts are, and focus on them. Do you need a professional made logo for your project ? Well in theory it would help but is it important at this point? A lot of things "would help" but they actually don't. Instead they take time and resources you need to allocate to the core of your business.

Let's say you are building a todo app. What is the epicenter of your app? Task management, right? So focus on getting that right first and foremost. The ability for people to chat through your app, or to export their calendar is nice but it's not the epicenter. People will expect great task management by buying your app. Everything else is secondary.

Say no to anything other than the epicenter. Say no to nice-to-have features. These will be created later. If and only if you get the basics right first.

Set some goals and create action items based on them. For example if your long term goal is to quit your job set smaller goals. Like getting the first paying customers. Create all the features that will make people pay for your product and ignore everything else until the time comes. You'll know when the time comes because it will be the next step required to reach your next goal.

5. Start with what you know. Play to your strengths.

It may look as if a new project is a great time to try something new and exciting like a new programming language. Why not seize the opportunity to have fun while you work? After all this is your project. So why use the same boring stuff you do at your day work?

However, that's not the case. Starting a business is a very hard thing to do. Even more when you start a side hustle. You have even less time and resources. If you spend time learning new things you further limit your available time.

On the search for customers and profitability you will be competing with others who have similar offerings on the market. Even if you start with a unique idea, others will try to steal it and copy your product. Unfortunately there is nothing you can do about it. That's one more reason to play to your strengths.

You may have heard the "principle of least effort" or the similar term "path of least resistance". It is a theory that covers diverse fields from evolutionary biology to web page design. It maintains that humans and animals naturally choose the easiest way to achieve a goal. In our case the "path of least resistance" is sticking to what you already know.

Sometimes you are forced to use something new. For example when you want to create an online store but you don't know anything about websites. Even at that time you should do it in the simplest way possible without getting into the trap of adding more work to your plate.

Besides, let's not forget that other than you, nobody will ever care what tech you use to provide a product or service. Nobody ever used Google because it was based on the X or Y tech stack. People use it because it delivers results.

The new skills you should be learning is talking to customers and giving solutions to their problems. What is the point of a fancy tech stack product if no people are using it? Like Arvid Kahl says in his article "How to kill your business": "Entrepreneurship is about empowering people, not trying out new tech."

6. Be passionate about it.

When you return home from a hard day at the office it's hard to get back to work for another four or more hours. What will get you through the hard times of working more is passion. This gives you willpower and mental strength to go through the extra work.

To have passion you have to genuinely believe in your idea. If the idea you chose does not inspire passion in you, then it's not the idea you are looking for. Keep the brainstorming going until you find an idea that does the click.

You also need to be excited about the technology and tools you will be using. Like we already discussed, it's best to stick to what you already know. If your current tools feel boring to you, then it can be ok to extend your stack. However lots of people choose tools out of fear of keeping up with tech. This is a big mistake. Some of the biggest successes out there were created with good old fashioned tools.

Also if you choose to have a partner, make it so he/she is one that inspires you and gives you positive vibes. You can't commit to something long term if the other person does not share your passion about the project.

Every one of the parameters of your environment (tools, tech, people) contributes to your potential success and raises your chances if you are passionate about it.

7. Start small, stay small.

Don't be intimidated by bigger competitors. Trust me, it's a huge advantage being small, agile and flexible. Big companies dream about having the flexibility and options that small companies have.

Take software for example. People just love it when there are no nagging configuration screens and wizards in software. Simple wins every time. You can take advantage of this in your product as well. You have little time and limited resources so make your product as simple and easy to use as possible.

If you present your idea as a small and simple solution to a problem, there are lots of customers who will immediately be excited. This is how you can differentiate from your competitors and provide unique value.

The same is true in ecommerce as well. There are thousands of successful small companies who love what they do and stay small by design. Take the caudabe iPhone cases for example. It's a small company in Chicago who makes perhaps the best cases out there. They win by staying small and not trying to imitate what the bigger companies do.

Staying small will force you to stick to the epicenter of the problem you want to solve. Your constraints will make you find creative solutions to difficult problems. In the end this is all that matters. Everything else can wait until much later.

You need to be creative about problems you are facing and find easy solutions that will get you forward faster. For example, do you need to create your own blogging system or will a wordpress installation work fine and save you hours of coding work ?

8. Build something you'll use yourself.

The best way to understand the needs of your customers is being one yourself. It may sound trivial but there is even a term for it and is an important business practice many organizations use to validate and improve their products.

It is called dogfooding. Many companies do it to test products before they are released to customers. It stands for using the product or service you are creating yourself. There are enormous benefits to dogfooding and it's obvious why it's in use across the tech industry.

By using the product you are developing you get to see bugs first hand. You also get to see if those bugs are important or trivial. If they are important you get to fix them and move on. If they are not, put them in a backlog and again move on.

When your users/customers have submitted say 100 bugs, how do you know which ones take precedence? With dogfooding you get to see first hand the severity of each problem in your product before it even gets reported. This increases the quality of your product and makes you more efficient and more likely to move forward faster.

If your project idea was bad you need to know about it as soon as possible. When using your problem it will become obvious if your idea was simply a solution looking for a problem. If using your application every day doesn't seem all that important, it may be the case of a bad idea. If your product or service is really something worth building you will seek to use it yourself.

Many times during the building of your product you will come across a crossroad. Should you build that new important feature, improve the design of your app or fix a pile of bugs on your backlog? Who can safely and surely make such decisions? Who can really know which task is the most important at the moment?

Once again eating your own dog food comes to the rescue. If you get to know which pains your app has, it gets easier to decide how to move forward. Besides, let's not forget that you are not a simple user of your product, you are one of the most active users of it.

You get to be on the same team as your customers. You will have similar needs and similar priorities. And above all you get to speak their language. During the validation phase it's easy for people to tell you something pleasant just to look nice. However when you're one of your customers you know how to ask the right questions which will give you valuable information.

More importantly it will make you deeply care. Would you trust a founder who doesn't use his own product? Your customers won't either.

The term dogfooding was born back in 1988. Paul Maritz, an employee at Microsoft emailed his manager using the subject "Eating our own Dogfood". As you would undoubtedly guess the email was about the idea of Microsoft employees using their own product. Which in this case was a new operating system for computer networks.

Another famous case of dogfooding is the one at Apple. In February 1980, Apple's president at the time, Michael Scott, wrote a memo announcing"Effective Immediately!! No more typewriters are to be purchased, leased etc., etc. ... We believe the typewriter is obsolete. Let's prove it inside before we try and convince our customers." The end goal was for Apple to be free of typewriters by the end of the year. The rest is history.

Facebook back in their early stages had a terrible Android app. The iOS counterpart was great but the Android one was quite behind. This was no coincidence as most of the company's engineers were iPhone users.

The first measure Facebook took was to ban the web version of the network internally. Then it encouraged it's engineers to start using Android phones. This made the engineers live first hand the pain the users were feeling. The results were impressive. The Android app started to constantly improve to the point where it came to par with the iOS app.

9. Show up every day.

Have you failed in the past at tasks that required dedication ? Have you ever wanted to start a blog or newsletter only to have it fail later on ? We've all been there. You start full of excitement, select the design, plan the posts you will be working on, maybe even write a couple of them and then…

You had planned to write a post for this Friday but it didn't happen. Then it didn't happen next Friday as well. And just like that your ambitious goal was abandoned, making you feel bad towards yourself and your willpower.

However people (wrongfully) believe that when you have enough willpower you have the ability to work a lot. It may come as a surprise to you but the truth is that willpower is the exact opposite. Willpower is a muscle. And you train it by working on what matters most.

But just showing up is not enough. You have to show up every day. And the way to do that is by forming habits. This is the way to train your willpower muscle. Unfortunately this means that it's hardest when you are just getting started. Indeed the first few days of forming a habit are the days you find excuses and procrastinate.

However if you just keep showing up your willpower muscle gets trained and it only gets easier as time goes by. For most people it takes from 20 days to two months (or more) to form a habit. Once you get to that point then you're on autopilot. It becomes very easy to do something which you have done every day for the past two months.

So how do you "survive" past the first few hard days? There are a few tricks that can help. First of all, make a routine and stick to it.

For example when I want to work out on the treadmill I first select a few YouTube videos to watch on my iPad. Selecting videos is far easier than working out. So it's not a hurdle for my brain and my willpower. But doing this simple task gets my brain in the mood for running. And that's because my mind knows that selecting the videos is followed by working out.

Writer Shawn Blanc likes to play the Monument Valley soundtrack every time he gets down to write. Yes, he listens to it every day. It may sound boring but it's part of a routine. It creates a connection for the brain to get down to work.

When you are working or simply being on routine preparation you should treat it as something very important. Avoid checking email or social media. This breaks the habit and makes concentrating hard again.

Another way to make it easier for yourself is to embrace constraints. Have you noticed that most people are most productive within a time limit ? There is a reason for that. Freedom creates a chaotic situation for the brain. I'm not saying that people should not be free in life. Just that when you place limits upon yourself you make working much easier.

The limits can be time related or topic related. For example as I write these words I have set a limit for myself that I should write one section per day. I can't get off the computer until I get one section of the article ready. Once that's over my work is done and I can rest or do whatever I want (leisure time).

When I'm coding I'm limiting myself to complete a feature or fix a set of bugs. I can't stop until the feature is over or the bugs are fixed. Once this is done I step out of the computer and rest. I should stress the importance of resting as part of the general habit forming process.

You should reward yourself every time you have fulfilled your commitment. This is a"thank you" for your brain. It gives yourself a pat in the back. It enables you to feel great for what you do and keep on doing it every day without it feeling like a chore.

Some people like to keep a work journal and log their progress. This allows yourself to experience the progress that was made. Besides that, journaling has a lot of other positive effects which however are beyond the scope of this article.

Be persistent even when the odds are not in your favour. You'll have bad days like everyone else. Don't get discouraged. Keep putting in the work. This trains your willpower muscle and makes things easier. Persistence and perseverance is the key. Great things take time to build. Rome wasn't built in one day.

10. Frequently re-evaluate everything.

Business plans are a waste of time

First of all let's talk about business plans. Formal business education suggests that the first thing you have to do when you start up a business is to write a business plan. It is a document that details a company's objectives, activities and the way it "hopes" to get there.

However there is a problem with that. And that is that business plans are a waste of time. Let me explain with an example. Business author Paul B. Brown set out to write a book about a collection of business plans from the early days of various successful companies.

He ended up scrapping the book. The reason was that he noticed that most companies turned up something completely different from what the business plan originally envisioned. And this was not in a subtle way. For example hardware companies ended up as software companies and so on.

Once you stop guessing about the future (because essentially that is what planning is) and enter the arena of real business, you will experience a totally different reality. One that is dictated by cash flow, survivability meeting customer demands and so on. A document you wrote two years ago doesn't matter anymore.

You should treat the market the same way we treat the weather or earthquakes. You can only see a week or two ahead. Anything more is wishful thinking. The market is constantly shifting. The best thing you can do is embrace it and act accordingly. Futurists of the past predicted flying cars, not the internet or smartphones.

While you are planning your competitors are selling and introducing new products to the market. Can you afford sticking up to a document with lots of guessing? That would be like a way to avoid reality and change. "It is not the strongest of the species that survives, nor the most intelligent that survives. It is the one that is most adaptable to change."

So how can you put this concept into action ? Set a schedule about reviewing your progress. For example on the first day of each week or each month. Go through each todo on your list and re-evaluate it. Is it really important right now? If not, you should delete it and move on.

Are you still on the right track? Talk to your customers about the features they need or the bugs they need fixed. This information should enable you to make informed decisions about where things are going. Features that looked necessary on day one could be not so important now that you got more knowledge.

Do you have a product but no customers ? Then perhaps it's time to focus on marketing instead. Do what it takes to get those customers coming and eyeballs focused on your product. Constant re-evaluation is the best tool to put you back on track.


Pivot is the act of repurposing your offering when you're not meeting your business objectives. Usually it's a complete shift in direction like the example of Slack. Now famous business communication suite Slack used to be a game called Glitch. The founders were on the brink of bankruptcy when they decided their concept needed a complete overhaul.

They had made a small tool for internal communication, which allowed people to message each other and see past messages every time they logged in. They decided that they should release it as a standalone product. Going from a multiplayer game to a business communication suite is not something you see every day. Yet it is what led slack to success.

Sometimes it's only a small part of the company or product that needs to change. This is how instagram was born. The founders had a location sharing app called Burbn. The most active part of the app was image sharing. They rebuilt it into a standalone app, and thus instagram was born.

When should you pivot?

When you have reached a point where your product or service does not get enough customers anymore you should consider a pivot. It could be simply a sign of bad marketing on your part. If that's not the case it could be a time to consider a radical shift in your strategy.

If your offering has a hard time due to more than enough competition it could be a sign of a market being saturated. This has the side effect that the concept is validated but sometimes competition can go too far to the point where it can suffocate your product. When this happens don't be afraid to shift course and start anew.

When you reach a point where your product is average but there is one section that performs great it is another case of a potential pivot. Like in the instagram example above, you can take what works from your app and re-release it as something new. In this case you should aim to serve a niche, not being an all around solution.

11. Failure is an option.

Not all ideas are great. You don't know which idea works unless you put it to the test. You may have done all you can to validate your idea, but sometimes ideas fail the real world validation test. The only test that matters.

The only ones who don't fail are the ones who don't try. But ironically, not trying is the greatest failure of them all. Can you imagine Michael Jordan being afraid to take a shot because he would miss it? If he was, how would he ever take the next shot which would win him the game? In his own words:

"I've missed more than 9000 shots in my career.I've lost almost 300 games. 26 times,I've been trusted to take the game winning shot & missed.I've failed over & over & over again in my life. And that is why I succeed."

Failure is part of the game. Sometimes you win, sometimes you learn the hard way. It's true nobody likes losing. But it's even worse carrying on with a failed idea when you know you can move on and work on something better.

For example, a few years ago I set out to create a small social network for the greek market. It would be similar to For those of you not familiar with goodreads, it is a social network for people who read books. As you may have guessed it was created by Amazon.

Learning from what I preached I created an MVP to validate the idea in just two months. My rationale was that I could create pages for each book available in the network. In turn google would index all the books and give me some SEO juice and some clicks. Those clicks would translate to users and the first people would spread the word and so on.

My lesson learned was that when you try to build a social network you need huge amounts of users to make the experience valuable. The little traffic I got from Google was simply not enough to create a vibrant social network.

I should have known you might say. But how could I have known that for sure? What if the traffic was enough and I was missing a huge opportunity? Now I know for sure because I gave it a try and I failed.

In the end it's not so bad. I lost two months of my life working mostly nights and along the way I upped my coding skills a bit. Now I have a better, real life understanding of network effects and moved on to other projects.

If you don't get results from your project within a reasonable timeframe simply call it a day. It's a real shame to see people in the indie hackers community working on "nice" ideas for two or three years only to realise in the end that the idea was fundamentally flawed in one way or another.

Even the smartest and most talented people and companies fail. Just visit google cemetary to check out how many failures google is having. Even the legendary Steve Jobs failed more than once: The Apple Lisa. Macintosh TV. The Apple III. The Powermac g4 cube. iPod socks.

12. Goals help you succeed.

First of all let's talk about goals. Goals are a set target that you want to achieve in a particular amount of time. There are short term goals and long term goals. Short term goals are timed in a quarter or year (the most). Long term goals are more like visions of where you want to be in 5 or 10 years. Long term goals are beyond the scope of side projects so we'll be focusing on short term goals here which we'll refer to as just goals from now on.

To better understand goals let's see a few examples of realistic ones.

  • Fix all outstanding bugs by the end of this month
  • Release version 1.0 by the end of the quarter
  • Get 100 paying customers by the end of the year

Goals you set should be SMART. This stands for Specific, Measurable, Attainable, Relevant, Time-bound. For example "Get more customers" is not a SMART goal as it fails most of the SMART criteria.

So why are goals important and why should you care? First of all, goals help point the ship in the right direction. It's very easy to wake up and sit at your desk working on things of low importance. However if you have specific goals you will find it easier to spot the important things to work on. It will be the ones that drive you towards your goals.

Another big problem goals can solve is the way to measure your progress. As you may have guessed, the simple and general rule of thumb is that if you're meeting your goals you are making progress. Of course if you are constantly meeting your goals with ease, maybe it's time to make them a bit harder. Goals should be realistic and not an excuse for faking progress.

Goals motivate you to get more things done and stay on track. Have you noticed how all sport games rely on goals to track the progress of individuals or teams? It's not by accident. Humans by nature rely on goals to track progress.

It's one thing to just sit at a desk and expect yourself to get to work and a whole different story to work with an end goal in mind. Goals give you a purpose at work and most important, reasons to celebrate. When you reach a small or bigger goal it's time to give yourself a pat in the back. And when you don't reach your goals it's time to reflect and see what went wrong. This is why goals also keep you accountable against yourself.

In the end, goals help you define success. The bigger picture, the ultimate goal is always the success of your project. And to get there you need smaller goals to act as stepping stones. Plan your way to your end goal correctly and thoroughly and you'll make your life much easier and your success more probable.

13. Break large tasks into smaller ones.

The best way to reach your goals is to be great at moving forward with your tasks. And the best way to do that is to master the art of writing great tasks. Tasks should be "small" and well defined. By small we mean that each task should not take you more than one hour to complete.

Large tasks are intimidating. When you have a task for example titled "Add chat functionality to the app", it's only natural not wanting to get it started. It's much easier to start a task titled "Design the chat interface" and it's far easier to start a task titled "Choose color palette for the chat app".

Break down your tasks until you can't think of anything smaller for any task. Hopefully what you'll end up with, is a list of perfectly defined tasks of reasonable size. Such a list can be started easily and can be processed through without any problems.

Small tasks help eliminate procrastination and reduce the "blank page syndrome" effect. It may take some time to prepare your task list but in the end it's always worth it. A well defined task list will make you more productive in the long run.

Another aspect of tasks is their categorization. Start by defining large chunks of work as "projects". For example our imaginary "Chat functionality" task from a few paragraphs ago is the ideal size to be considered a project.

It's large enough to be considered a project since it meets the following criteria: 1) It's a big part of the overall application. 2) It's large enough to contain a sufficient number of sub-tasks.

Once you have your projects planned out it's time to start breaking them up.

The next level in this hierarchy is called "task groups" or "todo lists" depending on the software you use to write them down and of course your personal preference. For example in our imaginary chat project the task groups could be the following:

  • Design the chat interface
  • Design the database schema
  • Code HTML & CSS
  • Client side functionality (JavaScript)
  • Server side code

Only then you should proceed to start adding the real pieces of work we call simply tasks. Don't hesitate to add a new task group midway through, if you find that it would help you categorize your tasks better.

If after all this process you still find that some tasks are quite large and you can't break them up, you can use a technique called "time boxing". Using this technique you add a duration next to the task.

For example if your task is "Write SQL queries", and you estimate that it will take you 3 hours to complete, then add 3 tasks titled "Write SQL queries for 1 hour". Of course the unit is up to you depending on the task. Imagine the following examples: "read 3 pages of...", "write 500 words for..".

14. Don't get carried away.

As we said before in section 11, failure is an option. Unfortunately not only an option, but a harsh reality for most people. Stats show us that 9 out of 10 businesses fail within their first 5 years of operation.

As you can easily guess it's even worse for side projects. When you have only a limited amount of time and money it's even harder to turn a side project into an organization that will make a profit.

Don't get carried away with unjustified optimism thinking you can survive without a stable income. The harsh reality is that paying customers are extremely hard to find and money doesn't grow on trees.

Instead of dreaming big about thousands of customers, try to validate your idea with 10 customers first. It sounds easy but it's not. You will have to do some marketing in order to have an operational funnel in place which can lure people in.

If you have a background in marketing then you know that building a product and simultaneously promoting it can be hard and time consuming. Get your project rolling first with a small but steady inflow of users and paying customers.

If you overestimate you will be greatly disappointed and fail. If you work hard for a long time and then fail hard, it can take you years to recover. The web is full of stories of founders failing with their startups or side projects.

Don't quit your job based on assumptions and an unvalidated idea. Only quit your job when your side project makes you more. Or at least an amount you can live comfortably with.

15. Avoid burnout.

You may have heard of burnout before. It's a stress condition caused by continuous exposure to stressful situations. You may have gone through it before yourself or may have had the early warning signs of burnout.

Why does it apply to you? Because taking on a side hustle can be exhausting. Trying to find work-life balance is a challenge in itself. Let alone trying to find work-life-side-project balance.

What causes burnout:

  • Time pressure beyond normal levels.If you are under time pressure at work, constantly trying to meet deadlines. If you have a job where ASAP is the dominant culture.
  • Lack of controlWhen you have little or no control on aspects of your work such as planning your daily schedule and workload.
  • Social isolation at work.Lack of communication and support from a manager. If you are feeling isolated in general it is a factor for increased stress levels.
  • Heavy workloadWhen you have too much on your plate. Your task list is always full and every day you have to work overtime.

These burnout symptoms can help you identify if you are at risk:

  • You are feeling constantly tired
  • You don't have the energy required to be productive
  • Every day is a bad day
  • Your sleeping schedule is different
  • You feel your motivation and optimism are greatly reduced
  • Your creativity is reduced
  • Your performance is suffering

How to battle burnout and work stress in general:

Take good care of yourself. Try to give up on junk food and eat a healthy diet. Add fruits and vegetables to your meals and try cooking at home if you can as it can take your mind off work.

Start working out. Find activities you like and get to it. For example I try to run on the treadmill or in a nearby forest at least half an hour a day. If you are not fit enough for running just start with short walks. Get your headphones and your favourite music and go for a walk somewhere calm like a park.

There are more relaxing activities you might enjoy, that will help you out. The easiest one is meditation. You only need a quiet room and 10 minutes from your time to meditate. You can also try yoga or tai chi.

Do anything you can to reduce your stress. Your body and mind will thank you in the long term. If you need to, put your side project on a temporary hiatus.

16. Consider a partner.

All the help you can get

You know how I have repeated throughout this guide about side projects being hard to do and how most of them fail. It is because it's true unfortunately. You are about to embark on a big journey with lots of obstacles in the way. That's why you need all the help you can get. And what could be better than sharing half of the burden with someone else?

In fact a partner can share the stress with you. Every time you freak out about a problem you can't solve, there will be someone near you who will tell you "Hey, we got this". This is a lonely endeavour, so you need someone by your side to take some weight off your shoulders.

A partner can also provide funds in addition to their time investment in the project. If you need equipment for your project or some other kind of resource (like buying ads on the internet for example) it's easier to get by if there is another person along.

A different perspective

You should not try to find a co-founder who will have a unique set of skills similar to your own. For example if you are a programmer why not bring another technical person aboard ? Two programmers, twice the speed, right ? Unfortunately it doesn't work like that.

It may sound counter intuitive but this is a mistake most people make. If you need a specific set of skills why not just hire that person? A partner should be someone who complements you. What you should be looking for in your partner is a different point of view.

A different perspective is what you need to perfect your decision making. If you are a technical person it's easy to prioritize your workload according to what is comfortable to your skillset. But a business co-founder can give you a unique point of view and "correct" your bias.


He/she should be someone who inspires you (and vice versa). You both should share excitement about the idea and the project in general. If you have to work hard to convince your partner about the project then likely, he's not the right person.

At the end of the day, do consider a partner, but don't think it's necessary. You can do it on your own. You can find lots of heated discussions on the internet about whether you should partner up with somebody. There are good arguments from both sides. All I wanted with this section is to get you to consider it.

Even if you decide to bring someone in, you should not rush it. The more advanced your side project is, the more equity you can claim when you are trying to bring a partner in. When all you have is an idea it's very hard to negotiate for a majority stake. But if you have at least a working prototype it gets much easier.

17. Well known successful side projects.

Let's have a look at some (inconspicuous at first) side projects that made it big. From side projects to successful great businesses millions of people love and use everyday.


Jack Dorsey (later CEO of the company) was initially a programmer for Odeo. He was then an undergraduate student at New York University. Odeo was a podcasting platform troubled by Apple's decision to include podcasts on iTunes. The year was 2005.

After a daylong brainstorming session at Odeo, Dorsey introduced the idea of an SMS based social network. The initial name for the service was twittr. The main reason it was not called Twitter initially was that the domain was already taken. It was six months later when they acquired the .com domain and changed the network's name to Twitter.

Dorsey began working on the project in March 2006 and published the first tweet ever."just setting up my twttr". Twitter went on to become the primary social network for news with a user base of over 300 million MAUs (Monthly Active Users). Twitter generated $3.7 billion revenue in 2020.


Software developers use a version control system called git. The most popular git host on the web is GitHub. It is an essential part in the development of almost every software project right now. As we speak it has more than 60 million users and $650 million in revenue.

Tom Preston-Werner and Chris Wanstrath were developers in the Ruby on Rails web development community. The problem they had identified was that Git was not very friendly to developers and that the whole process of online collaboration was virtually non-existent. At the time there were no commercial Git hosting options on the market.

They started working on GitHub in late 2007 as a side project. The website was made available for a few months as a beta and was released to the general public in April 2008. GitHub went on to adopt several innovative features such as a social networking layer. After many successful years of leading the market, GitHub was acquired by Microsoft in 2018.


Kevin Systrom and Mike Krieger (the founders of Instagram) were working on a mobile check-in app called Burbn (yes after the booze). They realised that it was too similar to Foursquare and that people were using it more for sharing pictures rather than sharing their location. Hence they created a new mobile app focused on just that, sharing pictures. Its name of course was Instagram.

On the first day Instagram launched (October 6, 2010), 25,000 people showed up. Two months later it had one million users! Another year down the line, it had 10 million users. It grew on and on exponentially and in 2012 Facebook bought Instagram back in 2012 for $1 billion. It was a wise decision. Instagram grew to more than 1 billion users in 2018.

In the beginning it was an iPhone only app with just a handful of filters. It wasn't until 2012 when an Android counterpart was launched. The key takeaway here is that you can find success with a simple idea, simple but polished execution and leave building non-essential features for later.

18. Epilogue.

Side projects are certainly a path worth walking. Even if your side project does not end up getting big like twitter or instagram it might just change your life. With enough luck, determination and skill you can turn it into a business that can support you and your family.

On top of that, when taken full time it can give you the opportunity to break free from 9 to 5. You can set your own rules, limits and boundaries about how and when you work. Do you want to work from home? You can do that. Do you want to travel with your laptop working from around the world? People have succeeded with that as well.

They are called digital nomads and they do just that. And it's possible to become one if you have a project that can make you enough money to quit your day job. It takes hard work, but above all it takes smart work.

Through the course of this micro-book we have discussed exactly that smart way to work. We have gone through the way to find and validate your idea. Then we discussed in detail about the right mentality to have when taking on a side project.

From setting goals, to avoiding burnout. From being passionate to dogfooding. This guide is here to help you now that you're starting out but also in the future. For all those times that you may feel stuck or just need a helping hand.

I'd love to hear your opinion on this guide. Feel free to hit the link to my website on the top of the page and contact me about your thoughts and ideas. I'm making a living off side projects and I think that maybe you can too!

All content © copyright Vangelis Bibakis.