Day Jobs vs Side Projects


Somehow I feel the expression, “Don’t quit your day job,” may be truer than people realize. Not in the disparaging sense, but in an optimistic one.

Optimistic because, I believe, side projects have many strong advantages over having a “real job” and that being a person who regularly tackles side projects is a likely heuristic for success.

The Underrated Power of Side Projects

The most obvious trait of side projects is their biggest shortcoming: you don’t have time for one.

Being unable to devote your whole day to a side project is practically the definition. Otherwise it would be your day job. I know a lot of part-time entrepreneurs, writers and programmers that focus on this limitation. If only they had more time, just imagine what they could accomplish!

However, there are hidden benefits to focusing on side projects. Indeed, I think being the kind of person who regularly invests a chunk of their free time in side projects will tend to come out ahead over people that simply work more hours at the office.

Side Projects Have Low Failure Stigma

I ran this business as a side project for nearly five years. As a university student finishing in a few months, I suppose it still is.

Of those five years, only the last one was enough to be a full-time income. As far as businesses go, four years without “success” is a long wait. If this had been my full-time occupation, I would almost certainly have quit a year or two into it.

However, while the first four years might have been “failures” as a full-time business, they were definitely successful as a side project. For the first four years, I made a decent part-time income doing what I love: writing.

Someone could argue that the long wait was due to my lack of total commitment to the project. I won’t completely disagree. Had I invested myself full-time I may have reached my goal earlier. But it almost certainly would have made the process a lot more stressful, not to mention it would have precluded me from experiencing university.

Low failure stigma means that projects can be bolder, less commercial and more creative than your day-job. Many of these projects will fail, but of the few that succeed, they often do spectacularly. Remember that Facebook was a side project.

Put this way, the psychology of vocation/avocation means that side projects have a lower median outcome but a higher variance. In your day job you want to make sure you can pay the bills and be responsible. In your side projects, you want to create something interesting.

I believe this trend holds even if you’re self-employed. We’re all familiar with bosses who want conformity over genius, but I think that trend holds even when we’re the ones calling the shots. As I shift into working for myself full-time I feel both amazing freedom, but also the sense of risk. Suddenly my reputation and livelihood are staked on continuing success. That pressure does make one work harder, but it also encourages avoiding long-shot projects that aren’t guaranteed to pay the bills.

Side Projects Force Productivity

I’ve also noticed I’m far more productive on side projects than on anything I consider my “day job”. I’m measuring here work done per hour of time spent working or thinking about the project.

When work is your day job, it is always there. It looms in the back of your mind, filling you with guilt whenever you take a break and demanding to be finished. You can mediate these effects, but they’re still there.

A side project, by contrast, is the fun part. It’s the recess from your regular work where you get to do something fun instead of something responsible. I can remember working on side projects where the moment I sat down I would be completely engaged until I was dragged away. Such moments are rarer when you have the entire day to contemplate a task.

While the overall time is limited to a side project, the productivity per unit of time goes up.

Side Projects are More Interesting

Side projects are more interesting, and not simply in being more interesting to work on, but in being more interesting in terms of results. If I’m doing a project for my day job, it may be boring at times, but it always feels necessary.

Because your after-hours work is pursued because it’s fun, the criteria shift for working. Instead of doing things that need to be done, you do them because they are challenging and interesting. While this can occasionally produce frivolous items, it rarely produces anything boring.

Perhaps the secret to truly interesting work can be to never put yourself in a position where working on it becomes a necessity (so that interestingness itself must drive you).

Side Projects Impose a Creative Constraint

Because time and resources are limited, side projects have more constraints than your day job. But in some ways, this can be a good thing.

One of my secret passions are indie games. Cool kids like indie rock bands, I like indie computer games, go figure.

While there are a lot of terrible indie titles, the best ones are often better than mainstream titles. The reason is that the author’s time and resource constraints force the game to take shapes it wouldn’t have taken with an abundance of money and staff. Games like Knytt Stories, Braid or Gish may lack the gloss of mainstream titles, but they are more innovative.

The constraints on a side project encourage minimalism and simplicity. While feature bloat is a common flaw of anything mass produced, it’s impossible on side projects. Either you keep it simple or you fail—there isn’t an alternative.

Side Projects Encourage Mastery

The road to mastery is often imagined as an agonizing path of endless hours of repetitive practice. That may be true for skills which require perfection of technique, such as playing the violin or shooting a layup in basketball.

However, for creative skills, I believe fun is essential to mastery. The most enjoyable creative tasks tend to also be the ones which teach you the most. While there is a tendency to stay within your comfort zone, creative tasks quickly become boring when you don’t take on new heights.

Because the ultimate criteria for side projects is fun, not profit, you’ll spend a lot more time actively improving the state of your craft.

Consider the freelance writer. By day he has to cover generic magazine stories given to him by his editor. By night, he can work on his novel, or start compiling research for a topic that deeply interests him. I’d guess he’ll be a lot better writer because of his nights than his day job.

Side Projects Evolve into Day Jobs

I should know, in a little over four months, my side project will become my day job. I’ve also known many other people who have taken a hobby and turned it into a profession. While this is certainly more feasible with some hobbies than others, the power of a side project is that it can eventually replace the day job entirely.

The character of the side project does change when it becomes your day job. Suddenly there is the pressure to pay the bills instead of just have fun. Your reputation becomes staked in its continuation so you avoid failure. Instead of being a bonus, it becomes a necessity.

However, overall, having an evolved side-project-turned-day-job is a lot better than a day job which was nobody’s side project to begin with. Even if the character does change somewhat, you still get to support yourself doing what you love to do.

Even if your side project never becomes your job, it can shift the nature of your work. As you gain mastery in a discipline through side projects, you may be able to shift your job or work more towards that area in your actual career.

Designing Life with Side Projects

I think it’s important to rethink work entirely if you want to make use of side projects. Companies like Google are already taking this approach by mandating employees spend 20% of their time on side projects.

Creative professionals have often seen their work in a dichotomy: the stuff that pays and the stuff they actually want to work on. The recognition here is that there will always be a tension in the distinction between your day-job and what you do on the side. Perhaps we can extend that mindset to beyond just the narrow realm of dissatisfied artists and writers, and onto work more generally?

Carving Out Time for the Side Project

I’m not entirely sure that if you aren’t the kind of person who likes side projects, that there is any way to become one. I feel the need to build things in one’s spare time is very likely a personality trait that some either have or they don’t.

That being said, if you are the kind of person who likes taking on longer side projects or missions, I think there is a lot you can do to become more effective at it.

The first is by acknowledging the importance of side projects. Too often, people shy away from side projects because they believe they are a waste of time. Unless you’re making money, it’s a hobby, and for many busy people, a hobby seems unjustifiable when there is actual work to be done.

However, as I’ve tried to outline in this post, side projects—particularly of the variety that are related to your chosen field—do have a lot of value. While the programmer who spends her spare time on carpentry might not find a lot of productive benefits, she might benefit a lot from creating a fun application that isn’t for her work.

Side Projects are Important and Fun

It’s my belief that we tend to spend pretty much all our time doing things that are either: necessary, important or fun. If you have a demanding day job, that means most of your time is spent doing things that are necessary. Some of that leftover time will be on things that feel important, and the rest will be spent on things that are fun.

The best way to carve out side projects, which cannot be necessary (or they would be a day job), is to make sure they are both important to you and fun. Important in the sense that you truly believe that working on them is just as important for you as exercise, sleep, eating right, etc.

Important isn’t enough, obviously, or we would never skip a day at the gym. Fun being the second criteria means that whatever project you choose has to be the kind of thing that you really enjoy working on.

Always Have Something on the Side

The suggestion I would like to adopt is to always have something going on the side. By maintaining the distinction between your day job and side projects, you don’t have to achieve the difficult task of having one type of work completely contain your identity. By splitting it into stability and innovation, you get to have both.

Image courtesy of recursion_see_recursion

  • Santi

    Great post Scott. I am a huge believer of side projects!

  • Armen Shirvanian

    Hi Scott.

    Side projects certainly have a huge added bonuses to them as you describe here. Their main reason for these bonuses is that we are not required to maintain them, so there is no pressure or worry to keep them going. They are a big bundle of potential.

    Side projects lend themselves to careers, while what folks refer to as “day jobs” often do not.

    I always like the stuff you talk about, and how you talk about it, and points that you add that I didn’t think of or elaborate on in my mind.

  • ah

    if daytime company is good and let staff off on time, it is good to have side projects……

    these days many of us worked till very late as mandated by boss, esp small co

  • Amanda

    Some really interesting perspectives on ‘day jobs’ vs ‘side projects,’ however, the implication seems to be that a day job isn’t likely to be creative and fun. I believe that it is possible, and desirable to craft a ‘day job’ out of our passions, even if it takes a while to be able to get our passions to pay the bills. I would be tempted to call the bill-paying work that we may do while developing ways of making sustainable income from our life’s work the ‘side project.’ Why make what we love less than the focal point of our lives?

  • Scott Young


    I agree your job matters. However my argument in this post is that working tons of hours at a job versus working fewer hours and taking on side projects is a better recipe for success. Not all jobs enable this, certainly, but a lot of chronic overwork comes from trying to keep up with expectations.


    Not at all. Day jobs can be wonderful, I thoroughly enjoy running my business and it lets me use my creative energies.

    The distinction is purely psychological. Once something becomes the anchor for your professional identity, your relationship to it changes. It becomes serious, instead of a frivolous pasttime. This has advantages (for one, it becomes a necessity that you work on it) but it also changes your relationship to your work.


  • Life Exceptional

    I completely agree with what you are saying. Day jobs are supposed to provide you with a stable, secure income, and so they should be something you can do well. On the otherhand, side projects can be more experimental, more fun and you don’t have the worry of paying your bills. Plus if they pay off the benefits are great while if they fail the loss is not so big as failing at your day job.

  • Jonathan G

    I think you nailed every point perfectly. Side projects give balance to life by allowing you to invest your time of things that are interesting, purposeful, or long-term projects with high pay-off.

    A lot of people are shocked by dissipating passion when a side project becomes a full time career and the pressure starts to build. By anticipating this shift, you can mentally prepare for the challenge, which generally helps with coping. Another blogger, Cal Newport, recommend not making the shift from side project to full time job until you can genuinely feel confident that the shift will go smoothly. This can come from a result of being well connected in the field you want to go into, have a large potential client/customer base, and/or have credentials that will take you far. You can read that article here:

    Until then, keep it a side project. You will feel less pressure, be more innovative, and have time to build yourself up and develop what you need to make the jump successfully.

    That’s my 2 cents 🙂

  • Scott Young


    I agree with Cal, but my ponderings about transitioning to full-time aren’t because of risk. Compared with most of my graduating class I’m in a rather enviable position–I have over a year’s worth of expenses in liquid assets and a business model that is surprisingly stable.

    Worst case, if everything went south, I could always get a job. 😉

    My arguments here are less about *whether* I will transition to full-time, but more the lifestyle I want to create when I do. I’ve seen numerous people go 100% into their businesses, but I see myself continuing part-time projects.


  • Positive Brother

    Thanks for sharing your thoughts on this Scott. I think this post will definitely apply to those of us who like to dabble in various interests. Like Rosey Grier (… the professional football player who had a huge interest in needlepoint, recorded songs, and took part in tv shows!

  • Alice Hive

    Hey Scott,

    I believe the whole concept of the “day job” that your income depends on pretty much sucks.

    Let me explain:

    I did have a phase (about one and a half years) where I treated one of my work projects as a day job but in the end it made me enjoy it a lot less, I became some sort of workaholic, and although I worked very hard I didn’t have to anything to show for it after two years.

    So, when I realized that treating one of my projects as my day job only made me compromise my needs, I just changed priorities alltogether: My new day job became “enjoying my life” and all work projects became optional side-projects.

    Indeed, that does mean that I don’t rely psychologically on any of my projects for my livelihood (even if I earn money with them!)- instead I rely on my own power and the universe.

    Since I’ve changed my priorities like that and see work as less important, ironically, my financial situation has changed in a lot more positive direction!

    As long as you give your work so much power over you, the “work part” will never end, and the “play part” will never begin.

    If there’s one thing in your life that you’re so passionate about that you want to do it all day, then please do it! But don’t stop to do things you enjoy because of the “seriousness” of work. Don’t stop to enjoy your life .

    I see that it’s a bit harder to adopt a perspective like this if you don’t believe in the Law Of Attraction, still it’s possible to prioritize your life differently and don’t feed your powers into something that doesn’t benefit you (the fear and of “not being able to pay your bills”).

    BTW, from the practical matters of starting a business, I do recommend to start them as side-projects: Start Your Business Today
    Not because I love day jobs so much 😉 but because I believe that it’s an advantage to start as early with your business as possible.


  • Jeannetta Burneisen

    “Don’t be afraid of the space between your dreams and reality. If you can dream it, you can make it so.” – Belva Davis

  • Alex

    I do believe that every developer/programmer should have side projects. It should not be about making them rich either! If you do something you love, it should not be a problem. Because the programmer is employed, there will be a need to hire a virtual assistant to assist with the administrative tasks of the side project. Some VAs are very knowledgeable in software and programming technology. One website that software developers can hire VAs is It is one of best that I know has certified, skilled VAs.

  • Bruce Harpham


    I like the “low risk” approach to the side project idea. Does “side project” always mean a business venture? Or does it include non-business activities as well?

    I have the day job and growing side project – the Project Management Hacks website – but sometimes I wonder that I don’t put enough time into leisure type projects.