How Side Projects Will Change Your Life Forever


As creative professionals, we often overlook the single most effective way of advancing our career and creating change in our lives.

We overlook side projects.

When you start a side project, you are taking control of your life.

Side projects demonstrate passion to future clients or employers.

Side projects give you the ability to showcase new skills or talents.

Side projects are completely under your control.


Tina Roth Eisenberg, founder of Creative Mornings has talked extensively about how she interviews for potential hires. Whenever someone comes to an interview, one of her first questions is, “What are your side projects?”

In this post, I share with you a mindset for how to approach your side projects, as well as example side projects that created unexpected changes in my life.

First, understand your motivations

One of the most important questions to ask yourself before starting any side project is: “What are my motivations for starting this project?”

That is an important question that you really want to think about. Some common motivations are:

• Practicing new skills

• Collaborating with new people

• Networking

• Passion

• Making an impact

• Leaving a legacy

• Creating a portfolio piece

• Generating income

There are a lot of motivations that can drive side projects, but before you dive in you want to figure out what is driving you.

When you know your motivations for a side project, it allows you to more easily measure success or failure. For example, even if a side project never generates a dollar of income, it could be a success if it became a portfolio piece or allowed you to work with new people.

Know your motivations and it will be much easier to evaluate your project’s success.

How my side projects changed my life

A few years ago, I started an ongoing side project that changed my life forever. I started a blog and podcast at

Jake Jorgovan on the Importance of Side Projects in Your Life

My purpose with this site was to make an impact and help others, and it has accomplished that. At times, I have received some of the most incredible letters from readers who talked about how my writing has changed their lives.

But unexpectedly, this site also began generating a significant income for me in a very unexpected way. In early 2014 I wrote a blog post titled How to make $1,000 per week on Upwork. At the time I didn’t think much of this post and just wrote it to help a friend who was trying to get his career started.

Since writing that post, it has hit the top of many Google search rankings and now gets over 14,000 hits per month. Eventually, I made friends with another individual who was successful on Upwork and had put together a course about his methods. I became an affiliate for his course and now generate almost $1,000 per month from this blog post without doing any work.


For a creative professional who lived a large part of my career from project to project, having $1,000 of passive income each month has been life-changing.

This is just one of the many incredible benefits that this blog has brought to my life. I’ve also won countless clients because the client says, “I looked at your blog and you seem like a really smart and trustworthy guy.”

You can’t know where your side projects will take you, but they often pay off in unexpected ways.

How a single blog post created a new business

The daily act of writing for my blog also created many unexpected benefits. As I wrote each post, I was trying to capture some valuable lesson that I had learned.

One post in particular captured the strategies that I had used at my first video production agency. It was called How I used stalking to land Fortune 500 clients. I wrote this post early 2014 and over the next two years found myself sending more and more people to the post to read about the strategy.

Eventually, I realized that the strategies outlined in this post were the single most valuable thing done in my career and these strategies became the foundation of my new business Outbound Creative.

Outbound Creative by Jake Jorgovan on Side Projects for CreativeLive

A blog post became a business, although if I had never been writing about what I was learning, I would have never made this connection.

You can’t know where your side projects will take you, but they often pay off in unexpected ways.

You never know where side projects will take you

When you start working on a side project, you don’t quite know what benefits it will bring.

It could lead to unexpected income.

It could become that portfolio piece that lands you your next job or client.

It could allow you to collaborate with someone who becomes your next business partner.

Or it could be something that you are so passionate about that it reinvigorates your love for life. You can’t possibly know where side projects will take you. But if you don’t have one, just start.

Even if you don’t know how this project will ever make you a dollar, just start.

Start a side project and stick with it.

If you can do this, I guarantee it will change your life in the most unexpected of ways.

For much more on how to launch profitable side projects, check out Money & Business for Creative Entrepreneurs with Ramit Sethi.


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Jake Jorgovan is a freelancer and creative entrepreneur. He founded Outbound Creative to help agencies land their dream clients. Join him on Twitter.