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I’m not sure if there’s a term yet coined for those who start companies in their spare time, so henceforth I propose those with full-time jobs and startups on the side shall be known as “side-project entrepreneurs.” It’s time people like us identify with each other.

At this point, I’d consider myself a “serial side project entrepreneur.” On top of my full time job at UP Global, I’m a co-founder of a startup called Red Ride as well as a startup called On average I work between 70 and 80 hours per week, in addition to being a newly married socially active 25 year old.

Balancing everything is painfully hard, and impossible at times, but I think taking on side projects is one of the smartest decisions I’ve made. It’s also made me far more valuable to the organization I work for. I’ve come up with four reasons that highlight why the experience has been and is so fruitful, although I’m sure there are many more.

1. Epiphanies Come From Practice

One of the most important things you’ll learn if you go to a Startup Weekend event is that the purpose isn’t just to network or to build companies worth millions of dollars in a weekend. The core of the experience is around this idea of experiential learning, or learning by doing. You might not have a designer, or even a developer for that matter, so what do you do? You download the free trial of Illustrator and you learn how to use it, or you pull an all-nighter to take as many free programming courses as you can so in the morning you’re able to hack something together. In your day job, you might not have the opportunity to dip your feet into all of these different buckets, and with that you’re missing out on the opportunity to try out new things. Get out there and do it.

2. Learn Your Limits

As mentioned above, I currently work full time as a regional manager at UP Global. I’m also the co-founder of Red Ride as well In addition to that, I’m a newlywed with a community of family and friends that like me enough to care if they don’t see or hear from me for weeks at a time. At this point, I may be crossing the forbidden “shiny object chaser” line, but I’m learning my limits, and to me, that’s invaluable. How far am I willing to go? Do I have what it takes to be a real-deal entrepreneur? You won’t know, you can’t know, until you prove it not only to co-founders or investors, but to yourself. If you want to learn your limits, pushing yourself, although sometimes painful, will prove immensely effective.

3. Build Your Autonomy

At UP Global, we’re fortunate enough to be about as autonomous as one can be at a global organization. We do an amazing job at trying to remain non-hierarchical during the high-growth stage that we’re in, but inevitably there’s a chain of command and big decisions have to go through some sort of process before being acted on.

Personally, I think this is how it should be, and it will be how I run my company someday, but it means that you, the entrepreneur looking to change the world, are missing out on the opportunity to really make the big decisions. What’s the most important thing that we should be working on right now? What’s our mission statement? What’s our big hairy audacious goal? Do we need to pivot and change direction as a company? These are the big decisions, and the tough decisions, and ones that you’re going to want to learn to make. Create something and all of the decisions will be yours. You might be surprised by how refreshing and rewarding this is.

4. Get Creative

You might love your job and you might have all the freedom and autonomy in your role that you could possibly want. (If you’re in a startup, you should. If you don’t, get out now.) But when you’re working on the same thing day in and day out you might find that you lose your creative edge. This isn’t a bash on your company or the culture there, it’s just something that happens to some of us, especially those of us that have the entrepreneurial bug. A side project can be the perfect remedy to this situation.

Being able to unplug from your day job for an hour or two at night to jam on something completely different opens up your mind to new possibilities. This is beneficial for you personally, but also immensely important to your company. Why? Because every single day you’re bringing a fresh perspective to the table, and one that’s been stretched creatively. (If they don’t see that, again get out now.)

Moral of the story? Get out there and do something! Your goal doesn’t have to be to build a billion dollar business, you don’t have to raise millions of dollars and you don’t have to be full-time.

Of course, none of those things are bad, but if you’re happy with your day job and you still want to dip your feet into the entrepreneurial world, embrace the life of the “side-project entrepreneur.” You won’t regret it.

Chet Kittleson is a regional manager at UP Global, co-founder of Red Ride and also co-founder of Seattle. You can find him tweeting about the Seattle startup scene at @chetkittleson.

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  • aaronbrethorst

    You might also want to consider checking your employment agreement and making sure this is a) allowed, and b) that anything you produce belongs to you.

    • ChetCrunch

      A good caveat, and probably something I should have added in fine print. I’d say if you identify with this notion of ‘Side-Project Entrepreneurship’ and find yourself at a company that doesn’t promote intrapreneurship, you’ve got a bigger problem. :)

      • Slaggggg

        Not sure what that means. If I’m paying a guy $150,000 plus a ton of options, I want his 80 hours a week going to my company. I don’t want to get half his brain, while he builds his real future elsewhere.
        I think side projects are fine … but don’t get upset when the company paying you its hard earned money actually wants your full attenion.

        • T

          Sorry, because you work for a company doesn’t mean they own you. What you do in your free time is your business and your business only. What your “brain” does in your free time is NO business of anybody else.

          • ChetCrunch

            Agreed T, and Slaggggg raises some good points as well. The keyword here is “side project.” If the side project ends up interfering with your day job, which is definitely a possibility, that’s definitely a problem and one your company won’t be happy with. At that time, it might be time to take the leap. :)

            Also important to note that many of the big corporations out there have programs specifically to encourage entrepreneurship and intrapreneurship. Microsoft has the Garage, Google has the 20% rule, Coca-Cola has an internal incubator and also has internal Startup Weekend events, and the list goes on and on. This isn’t a new idea, and is being embraced by companies large and small.

          • balls187

            I agree with you that a company doesn’t own you.

            On the flip side, I would expect you to give it your all while you are at the office, doing everything you can to build a great company.

            The same way if you were a founder of a start-up, you would expect all your employees to behave.

          • C

            Where did anybody, anywhere say “don’t give it your all while you are at the office”?

          • balls187

            Bro, do you even lift?

    • balls187


      I’m fairly confident that laws in WA limit this by: Anything you do on company time, or with company property, or with company technology, is fair game for your employers to go after. There may be additional non-compete clauses that limit you to not pursuing competitive areas (this maybe a grey area when dealing with mega-hyper-conglomerates like MSFT).

      • aaronbrethorst

        When I joined Microsoft in 2003 I was given a moonlighting agreement and enumeration form to fill out that detailed everything I was working on in my own time that Microsoft did not own. AFAIK, they still do this today.

        • balls187

          I’ve had to fill out the invention disclosure agreement in the past with things I’ve invented (which have totally disrupted the disruptors), such as a time-traveling potato peeler, wasabi flavored chewing gum, and a wi-fi enabled jello shots.

  • Slaggggg

    BTW, do this when you are 25. When you are 40, you can’t do it anymore. You just can’t, no energy to get home from work at 7pm and start fresh on your side startup project…

    • T

      Speak for yourself.

      • balls187

        Right, because there is a large number of 40 somethings here in Seattle that are going all out at the office killing it, then coming home and creating the next Tableau, INRIX, or Avalara in their spare time.

        • C

          Actually, research shows the average age of a successful entrepreneur in high-growth industries such as computers, health care, and aerospace is 40.

          • balls187

            “Studies” have shown that it takes 5 years for a company to deliver value. So if the average age is 40, the average age for a startup entrepreneur is 35.

    • ChetCrunch

      Remind me to send an email to everyone that cares about me letting them know that if this is my mentality when I’m 40 to gut punch me. Drab. Not to mention all of my mentors, who are well into their 40’s, are still out there tearing it up making most of us 20-something year-olds look like old men. Tut tut.

    • balls187

      cool story bro

  • Jmartens

    Side projects are great, but its a far cry from full-time entrepreneurship. In order to give your employer everything you can, or give your side-project everything you can, you’ll eventually have to go one way or the other.

    I cut my teeth on side-projects, but looking back I gave them and my day job a half-hearted effort, each. At the time I thought I was managing both fine, but hindsight is 20/20 and I lied to myself then.

    So yes, do a side-project but plan from the start to either do your side-project full time within 12-24 months, or end it. Otherwise, you are more of a hobbyist than an entrepreneur.

  • balls187

    This title is misleading.

    You’re not trying a “side-project startup.” You’re just working on projects on the side (“You” being the general you…)

    Speaking as an engineer, I’m all for working on side projects, for fun, for profit, or just for the fucking taste of it.

    But building relationship with customers, investors, hiring, raising capital, are all important aspects to startups, which “working on the side” doesn’t account for.

    • ChetCrunch

      I totally agree with this, but it looks like the headline did a good job at capturing eyeballs. :) ( The original title was actually just “Side-Project Entrepreneurship”)

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