How to Execute a Successful Side Project

I’m a big believer in the power of side projects. This blog was once a side project. Same for the business behind it. Nearly every professional milestone I’ve made was from something that happened in my spare time, and I don’t think that’s an accident.

Side projects harness the unexpected. While your regular job and career needs some stability so you can pay the bills, you can take much bigger risks with smaller projects. A few of those risks will really pay off, and may even evolve into new full-time opportunities.

The problem is that side projects are difficult. You don’t have a lot of time to work on them. The motivation to work on side projects can also wane. Nobody will fire you for not showing up on your pet project, so they die more often from neglect than outright failure.

I want to share some practices I’ve found useful for picking side projects, and more importantly, actually finishing them.

Designing the Right Project

A surprisingly big part of finishing a side project is making sure you choose the right one. Most side projects fail before they start because the person didn’t design them properly. I keep an eye on several criteria whenever I take on a new project.

1) Pick a Few Hard Constraints

Contrary to popular opinion, flexibility doesn’t make a project easier to execute. Hard constraints force you to be realistic when making estimates and prevent your project from ballooning in scope.

When I started the MIT Challenge, I made my constraints very clear from the start—pass the final exams. Early on I added programming projects to that criteria, but otherwise the goal was clear and constrained. This omitted a lot—I wouldn’t do presentations and I would only do assignments to help me learn the material. But those omissions also made the project feasible.

A good rule of thumb is that a project should have at least three constraints: scope, content and mission. Scope means you constrain the project to be only a certain amount of time or a very clearly defined size. Content means what you’re actually going to do—I chose exams and programming for my MIT Challenge, but I could have gone with something different (say a research project). Mission means you narrowly pick what your project stands for, which then lets you make cuts more easily when things start to grow.

2) Look for Random Upside Potential

Random upside potential is when a project has the ability to push you into new territory and has the possibility of big rewards if it is successful. These kinds of projects usually leverage some of your expertise, but also include a large random component which means you’ll end up needing to learn a lot to keep up.

I know I’ve found a project with random upside potential if I can get excited about the possibilities of success, but I’m also unsure exactly how to execute the project. Projects which lie entirely within your existing expertise will be more stable, but also lack this random upside potential.

3) Make it as Big as it Needs, But No Bigger

Most projects have a crossing point. Any smaller and they sharply lose their random upside potential, interestingness or impact. The best projects are those picked just past that point.

I’d love to make a blanket statement that the best projects are three months or only require 100 hours, but I’d be lying. The MIT Challenge was a year-long project, and took thousands of hours. Had I done the “do a freshman year of MIT in three months challenge” it would have been significantly less interesting.

However, it’s easy to let projects grow in imagination. Your idea for an app you want to build on the side starts with a few core features, but then balloons into a monster. Monstrous projects are really hard to finish.

Executing the Project

Once you’ve designed the project, you then need to do all the work. This is the hard part and where most projects fail. Fortunately, if you designed your project well, implementation is far easier.

I stress the importance of good project design because fixing design errors is far easier than combatting the difficulties of execution. A few strokes of the pencil on a notepad is much easier than altering the discipline, motivation and sweat that comes later.

1) Be Realistic With Your Time

A common mistake is greatly overestimating your willpower and motivation in the planning phases. It’s one thing to say you’ll wake up at 5am every morning to put in two hours on your project before work. It’s a very different thing to actually avoid pressing that snooze button.

I like to do a test week of a project schedule when I’m still in the design phase to see what’s reasonable. I did a pilot course before I started the MIT Challenge which let me know what trying to do a course in one week would look like for my time.

2) Work Strictest in the Beginning

I started at a class-per-week pace during the first few months of the MIT Challenge. This wasn’t necessary—there were 33 classes and 52 weeks to complete them. However, doing this gave me a cushion for the later classes which could have been more difficult, or if I got burnt out.

You can overdo this. Starting an exercise plan with a 20-mile run is a bad idea. But your motivation will never be higher than the first few weeks, so use that momentum to lay out good habits.

My suggestion is to be the most rigid about your work schedule in the beginning, and let yourself relax more as the project stays on target. The early stringency will mean when your discipline wanes later, you’ll still be on schedule.

3) Set Triggers to Combat Perfectionism

Perfectionism is an easy trap to fall into, particularly for those favorite projects of yours you really want to succeed. It can be hard to say “this is good enough” and move on.

The truth is, the quality you can execute is relative to what you’ve executed in the past. I’ve met almost nobody that has had a spectacular success from a first attempt without an intermediate level of quality from a less successful prior project. This means perfectionism can become a cancer if the quality you’re trying to achieve isn’t possible from a first iteration.

The best way to combat this tendency is to define trigger moments where you’ll be forced to move onto a next stage. Setting hard deadlines for milestones and not allowing yourself to fudge them later allows you to perfect as much as you can but pull the trigger when time runs out.

The Lifelong Project Mentality

If you’re not already doing a side project, I’d recommend starting one. Although they can complicate your schedule and make life busier, they are one of the few consistent keys I’ve observed in almost anyone who has impressive accomplishments.

I try to have the practice of always having a side project. If there is a period without a big side project, I’ll take on smaller ones that let me dabble and reflect for the next one I’ll undertake.

The biggest achievements your life are rarely going to be those someone forced you to do. They’ll be the things you undertook from your own initiative. Execution is a skill and it is cultivated through practice. Side projects are valuable because they instill this habit of making your ideas a reality.

  • Spencer Rowland


    Your timing is perfect as I just entered the execution process of my current side project. Your comments on controlling the scale of the project in the design process particularly resonated with me. I consistently would find myself expanding the features of the project and then would become intimidated with the thought of actually implementing them. After further consideration, I have decided on a design that is just outside my comfort zone but yet, not unfeasible. Thanks for another great post.

  • Day Trip Dreamer

    I really enjoyed this post as I also thrive on side projects (like my latest blog). You’ve inspired me to refocus some of the things i’ve got on the go so thanks for sharing. And of course, it’s exciting to come across a fellow Manitoban!

  • Paulien

    This is a great post, and very inspiring. I have been feeling a bit out of sorts lately, and the lack of a good side project may just help me get back on track. I finished my phd five months ago, and started a new job a few months earlier. Now that I am settled in, the extra free time I have since I no longer have to write my thesis etc. is starting to feel a little empty. However, I have some trouble in getting ideas for a good side project. Do you (or another reader) have some advice on what types of projects are good, or how to brainstorm for ideas?

  • Noel Saniel

    Hey Scott,

    I like how you said to look for, “Random Upside Potential.” See, I’m an undergrad in a university in the Philippines, and I just started a big side project: the creation of an inter-university, student-oriented organization that gives free tutorials for my fellow students. I know that I’m pretty good in the classroom, but tutoring others–and creating a plan and a system where volunteers can help others–now that would push me to new territories! I definitely need to stay on my toes to make this project a reality.

  • Steve Bithell

    Great post. These ideas are good for all projects, particularly using scope/content/mission to get a really clear definition of what the project is not, instead of the (typical?) chuck it all in and then some…

    Also listened to the Degree of Freedom podcasts this week. I used similar methods while studying for a DPhil.

    Keep it up, sir!

  • Armen Shirvanian

    “The biggest achievements your life are rarely going to be those someone forced you to do. They’ll be the things you undertook from your own initiative.”

    That is some gold right there, and I’ve never seen anything against that line of thinking. We only get great at the things we have no desire to cut corners on, and that we want to add the cherry on top to.

    There’s always some cool stuff in your content.

    The hard constraints portion also is very valuable, because lack of limitation or constraints leaves the project too large, and then you end up giving up shortly. Some limitation or constraint keeps things manageable, because our brains will go into un-manageable mode if not prevented beforehand.

  • Jaicidi

    I think I know your next big project, Scott.

    You’ll be trying to learn four new languages within 12 months.

    If not four, then perhaps three.

    amiright or amiright?

  • Nina

    I’m so fun of your organisation and creativity Scott, I’m 34 and so little organized, « big dreams but small engin » but I’m working on to improuve this, your ideas and blog are so usefull to me, a real reference!

    Merci beaucoup!

    PS. Yeah and, if languages are your next step, try, someone who’s been traveling for many years recommended it to me and I have finnally started my forth language after years of waiting


  • Michael Bowen

    Do you keep a log of your side project?
    What data do you track?

  • Scott Young


    Yes–Pimsleur is a great course (with a language like French, however, it’s often a pain that there are no transcripts by default–learning how a word is spelled is a big part of remembering it).


  • Sonny Recio

    This is great! I love your posts it has meaningful content. Regarding on this topic I believe you got that right for all people having sidelines while working in an industry.

  • Ronnie M

    I could not understand the design aspect. It is very sterile and not emotional related. As each person is different. What is the minimum characteristics of a person to be able to use your advice? For a person who is layback and doing just enough is ok, this will not work for this person. Am I right? Thank you.

  • Zaima


    I do belief timing is very crucial but again you never miss different constrains which may me more crucial than the time you scheduled. I have designed and scheduled my side project which is online PHD study on early childhood education. My most difficult challenges was internet connectivity and shortage of reverences that makes me fail in the middle road my credit is now 44% equivalent to 22 credits but I worry to be unable to continue because of internet challenge.

  • Zaima



  • Bemis J

    I tend to take on more projects than I have time for. This is really helpful.

    Thanks for the read.

  • Emmanuel

    Noel Saniel,

    It’s not the same idea, but meaby you can get a better idea of your project looking this page, it resonated in my mind when I read your post since I, in my mind, feel that’s similar to what are you doing.

  • Emmanuel

    Ups, here is the link: