3102 6:14 Weekend Workshop

Weekend Workshop: Back to the Future

This new segment is all about helping you learn the key steps to a new side hustle in 2025, one step or concept per week. It includes activities, examples, and more—and of course it’s all free. Today’s topic: what to do once your hustle is up and working well.

6:14

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Episode 3102

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This transcript was generated from the episode audio and may contain minor errors.

[Music]

Let's go back to the future today. Welcome to the Weekend Workshop. This is a segment we've been running all year. We're now midpoint through the year. It's all about learning the key steps to a new side hustle, one step or concept per week.

This segment is built on the book "Side Hustle from Idea to Income in 27 Days." It just so happens today's episode comes from day 27. So next week, I'll explain a little bit more about how the segment will look for the rest of the year. But for now, we have come to the point of considering what to do once your hustle is up and working well. So this segment includes activities, examples, and so on. Of course, it's all free, just like everything we do here at Side Hustle School.

So if you're not at the place where your side hustle is up and working well, well, that's okay. Let's help you get there. You can go back and listen to days one through 26, also free, always on the website. But for those who have made it thus far and have a side hustle that's bringing in income, what do you do next? How do you evaluate your progress and make strategic decisions about the future?

And this is a great place to be, of course, because you're like, okay, I've been working on this thing for a while, I had an idea, and I pursued my idea. I didn't just think about it, I took action on it. And I set up my product or my service, and I created an offer, and I learned how to identify my target customers, my ideal customers, in fact, and reach those folks. And now I'm actually bringing in income. So you've launched the hustle, you've made your first sales, you've learned some lessons, no doubt, along the way.

What now? And here's a key point. Unlike traditional businesses that might follow a standard growth trajectory, side hustles offer a ton of flexibility. You don't have to do it the same way everybody else does. You don't necessarily have to say, oh, I have to scale this business, and now I need to think about employees and so on.

I mean, some people do that, but it's also okay not to. The example I used in the book, Bob and Barb Bence, baseball fans who created a business called Ballpark Sweaters. They're custom white sweaters with red stitching that resembles baseballs. Got started totally organically. Barb wore her prototype to a Phillies game, and other fans walked up to her and asked where they could buy one.

So that seemed like a pretty good idea for a side hustle, right? They recognized the opportunity. They ordered 200 sweaters from a manufacturer, from one to 200, so that took some boldness, but then their first order sold out in just 45 days. Well, the business now brings in consistent income. They don't do a ton to market it, but the financial reward is not the only benefit.

It's also given the couple a shared project that they enjoy working on it together. And they've just decided, here's how we want to run our business. We're not gonna necessarily run it the way a consultant would tell us to, or anybody who's intent on growing it, going on Shark Tank, whatever. Again, they have financial reward from it. It's working, it's profitable, but it also kind of works according to their schedule and to their needs.

I always say that your side hustle should serve you, not the other way around. People tend to get stressed out when they think they have to do things the way somebody else expects them. In fact, my whole mission in life is to communicate the message. You don't have to live your life the way others expect. That's how I started sharing online with a blog called The Art of Nonconformity many, many years ago.

So again, the beauty of a side hustle, it doesn't have to follow someone else's rules. You can decide what role it plays in your life. Your journey doesn't have to end with a launch. It's just beginning. And unlike that traditional career path, you get to choose the destination.

All right, that's the big picture. That's the philosophy. Let's take a quick ad break. When we return, charting your course. Gonna give you three paths to choose from, and you might end up making your own path, but three options when we come back from the break.

[Music]

All right, charting your course. As you consider the future of your hustle, you typically have three paths to choose from. All right, path number one is to scale up. And we've certainly seen some stories of people doing that, making millions of dollars a year sometimes from their project. If your hustle is doing well and you enjoy it, you might choose to invest more time and resources to grow it further.

So that could mean expanding your product line, reaching new markets, or eventually transitioning to full time. Nothing wrong with that. Path number two, maintain. Just keep doing what you like to do. That's what Bob and Barb did with their baseball sweaters.

So a lot of successful side hustlers find the sweet spot, or it's kind of a lifestyle business. And there's nothing wrong with that. It's actually a good thing. Sometimes people in the startup world look down on lifestyle businesses, which I think is just crazy because isn't the whole point of life to be able to do what you want, right? But the sweet spot is where your business generates some meaningful income without consuming too much time.

And so people who choose this path tend to focus on efficiency and sustainability rather than growth. So you've got scale up, maintain, and you've also got path number three, which is automate or sell. Like there are some side hustles can be systematized to run with minimal involvement or even sold to someone else once they're established and profitable. This doesn't work for every project. If you want to build your project, your business intentionally with the goal of selling it, there are some different things you need to do than just running it as a lifestyle business.

You really need to focus on systems and creating a process that anyone else can follow, kind of separating the business from yourself. So that's a very different path if you choose to go down that road. Sometimes people have a lifestyle business and then the lifestyle business gets really successful and they think, well, maybe I should sell it, but it's hard to sell because it's so closely tied to themselves. And that would be the case for me. Like pretty much every business I've ever built is closely tied to me.

It would be hard to sell it. I've just kind of accepted that. But if your goal is to sell, then you probably need to be intentional about that from the beginning. So path one, scale up, path two, maintain, path three, automate or sell. It is your choice, right?

It's up to you. Your action exercise for the week, pretty simple. Let's reflect on your experience so far. What parts have you enjoyed the most about your business, your side hustle? Which aspects have been challenging?

How does it fit with your broader life goals? Like what do you want to do in life? Again, I think that's a super important question for all of us to ask and answer. And maybe here's a specific one. What would success look like one year from now?

One year from now, what does success look like? The true value of a good side hustle goes beyond money. It gives you options, builds confidence, it creates security. So whatever path you choose, you've gained some valuable skills and experience that no one can take away. And you should be proud of that.

And hey, whatever stage of the journey you're in, I hope you feel proud because you're already investing in yourself. You're investing in yourself by educating yourself. You're listening to this podcast, just 10 minutes a day. Hopefully it gives you a point of inspiration and some knowledge, maybe some ideas to move forward positively. Last but not least, it's always better to have a simple idea.

You can start right away than a brilliant idea that never launches. Thanks for joining me today and for this series. As I said, next week, I'll give you an update on what we'll do next, but I'm always grateful to keep making a podcast for you. Day after day, seven days a week. This was episode 3102 3102.

Always completely free on the website or follow or subscribe wherever you get your podcasts. My name is Chris Guillebeau. You're listening to "Side Hustle School." [Music]

From the "Onward Project."

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