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The Key to Building a Successful Side Hustle

Living and breathing side hustles since before it was cool, Chris Guillebeau is the host of the daily Side Hustle School podcast and the New York Times bestselling author behind The $100 Startup.

His latest book (which came out this April), The Money Tree shares tips and stories accumulated during a lifetime of self-employment and travel. In addition to 4 years as a volunteer aid in West Africa, Chris visited every country before he turned 35. 

Chris has been hugely influential for me, from building a profitable side hustle to creating communities. And when he sat down with me for an exclusive interview on Process Makes Perfect, Chris walked us through the processes, tools, and philosophy behind his successes.

The Details Are in the Process

“You can’t visit 193 countries without having a process.”

The biggest challenge to starting and scaling any project – whether it’s visiting all the countries or launching a side hustle with only $100 – is figuring out the logistics. That’s where process comes in. 

When it comes to starting a side hustle or launching a business, most advice hinges on following your passion. But Chris recommends taking a more practical and accessible approach and starting with the skills, experience, and resources you already have.

Don’t Get Hung Up on Your Resume

Even as side hustles become more common (and necessary), there is still romanticism around what a side hustle should be. This leads to unrealistic understandings of what skills and resources are needed to get them off the ground. 

Unlike other forms of entrepreneurship – such as launching a startup or scaling an existing business – everyone already has tools and skills that can be leveraged into a side hustle. Or, as Chris puts it, everyone’s an expert at something.

Start by taking inventory of what you already know how to do and are reasonably good at. This is where your formal and informal resumes meet your hobbies. How can you turn these skills and experiences into a product or service that you can offer?

Remember, your side hustle does not have to be your “dream” business or passion – at least, not at first. 

Maybe you took up sewing a few years ago to deal with the stress of the day job you hated. Suddenly, there is an explosive market for cotton face masks and people with the skills to meet the shortage.

Or, maybe you have been managing remote employees for years and have the knowledge that so many managers are scrambling to get on such short notice. Suddenly, an eBook or online course on how to manage remote workers is in high demand. 

While these are just a few examples in today’s ongoing pandemic, they reflect how some of the most successful side hustles start: out of necessity. 

Learn to Love the Process

Some of the most legendary side hustle successes involve an idea that took its founder in a direction they couldn’t possibly have seen coming.

In his book The $100 Startup, Chris tells the story of a former advertising executive who picked up a side hustle delivering mattresses when he was suddenly left unemployed. The business eventually grew and evolved into a 7-figure retail operation. 

But scaling a side hustle up to a multi-million dollar business doesn’t necessarily have to be the goal. For most people, side hustles are a way to make ends meet, supplement the income from another job, or to survive after losing a job.

By definition, side hustles are typically about making money off a small initial investment. But for Chris and so many members of the “side hustle nation,” they are also about realizing a bigger vision or goal. 

For Chris, accomplishing all this started with one question: How can I do what is important to me and contribute meaningfully, without depending on someone else for my security or wellbeing?

And when he found his answer, he discovered that he already had the skills and tools necessary to achieve it. But to get there, he had to learn to love the process. 

This is what sits at the center of what Chris does. Over his years, he has seen that successful side hustle – regardless of what motivated them to start – have one thing in common. 

Whatever your own needs and motivations are, you already have a set of skills and tools that you can transform into a side hustle. But – as Chris has learned and we preach here at Trainual – if you want to achieve audacious goals, you have to learn to love the process.

Learn to Love the Process

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