How to Turn Your Side Hustle Dream into Reality

How to Turn Your Side Hustle Dream into Reality

Are you always telling friends and family about how tired you are of the 9-to-5 grind and the brilliant idea you have that could set you free? Then maybe you get busy, forget it again for a few months, and find that the business you've always wanted to start or the book you swear you're going to write is still only a pipe dream. In this post, we'll share some practical tips for turning your side hustle spark into a roaring inferno, so you can stop wondering what might have been and start building.

Get Started Now with What You Have

Sometimes when you’re thinking about something you’ve always wanted to do, the easiest way to let yourself off the hook is to think that it’s too late to do it. But there’s an old saying sometimes attributed to the philosopher Confucius that you use to overcome this self-limiting notion: “The best time to plant a tree was 10 years ago. The second-best time is now.” Sure, you might lament not starting your side hustle when you first thought of it, but you’ll regret it even more if you never get it going or wait for that mythical “perfect time” when everything just falls into place (newsflash: it never will).

Once you’ve committed to finally doing the thing that’s been in the back of your mind for so long, the next falsehood to get past is believing that there’s a long list of prerequisites you have to check off first. A wannabe photographer doesn’t have to buy an expensive camera before building their portfolio, an entrepreneur shouldn’t wait until they’ve created a whole product line to launch their business, and a writer doesn’t need a journalism degree to begin pitching editors. Remember, you are the boss here, so you’re not going to get fired if you don’t have everything figured out right away.

“Start with what you have. The most common thing people think when starting a side hustle is: ‘I must have a website, a logo, etc.’ But I didn’t have any of that,” entrepreneur Arnita Johnson-Hall told Harvard Business Review. “I wasn’t afraid to work with what I had, which was my laptop, paper, a printer, and my knowledge.”

Carve Out Time

If you allow it, busyness will choke the life out of your side hustle and send you right back to the dreaming phase. That’s why it’s essential to figure out when you can realistically work on building your business or practicing your creative craft. The first step in doing this might seem counterintuitive: decide when you cannot do it. There are some essentials in your life that you can’t simply drop to make time for your new venture, whether that’s all your kids’ pick-ups and drop-offs, your main job, or making dinner for your family nightly.

Once you’ve listed all those times when non-negotiables need to stay on your calendar, you should then find the optional activities that you can stop or cut back on. These could include hobbies, that book club that you’ve secretly been wanting to quit for ages, and anything else that makes you wonder “Why am I still doing this?” when you see it pop up on your schedule. Being ruthless in eliminating or at least minimizing such things just bought you time to focus on what’s more important. Now you know when you can pump air into your side hustle, it’s time to put it on the calendar and make sure you protect these sessions fiercely.

In his book Daily Rituals: How Artists Work, Mason Currey commented on the power of consistently putting in effort on a set schedule to build something meaningful. He stated that routines “connate ordinariness and even a lack of thought; to follow a routine is to be on autopilot. But one’s daily routine is also a choice, or a whole series of choices. In the right hands, it can be a finely calibrated mechanism for taking advantage of range of limited resources: time (the most limited resource of all) as well as willpower, self-discipline, optimism. A solid routine fosters a well-worn groove for one’s mental energies and helps stave off the tyranny of moods.” Even if you can only set aside 30 minutes a day or an hour a few times per week, this consistent routine will be far more effective than just picking your passion project back up as and when you can make the time.

Find Your People and Serve Them

While you’re getting your first product, piece of artwork, or service ready, you also need to do what photographer, author, and CreativeLive founder Chase Jarvis calls the “other 50%.” In a video and accompanying blog post, he explained that doing the work itself and sharing it is only half of what you need to do to become successful with your side hustle. The remainder is participating in and contributing to a community, before, during, and after you want to share your own work and try and get customers to buy it.

“If you are just starting, put yourself in a position to win,” Jarvis wrote. “Go to conferences, visit online communities, follow people who are active in the industry and add your voice. The word networking is overrated. It’s just people and relationships. If you strive to build meaningful and valuable relationships – online and offline – you’ll be well on your way. There are no shortcuts.”

In a follow-up video, Jarvis stated that this includes in-person interactions. “You – human – go in real life to where people in your city meet…you’re going to have to participate in some form of actually getting together with like-minded people,” he said. So if you’re a start-up founder, attend local entrepreneur meetups, or if you’re a creator, join the nearest chapter of a professional organization in your industry. The online participation part can become a minefield, as it seems everyone is always promoting their business or making an ask. In his book Creative Calling, Jarvis suggests a better way:

Give, give, and give some more. Your audience isn’t something to leverage. It’s something you cultivate, nourish, and sustain. How do you sustain your audience? Value. Nowadays, people get 100 followers and immediately try to sell them something or become a sponsored influencer. I wrote more than a thousand blog posts and racked up millions of views before I even considered “pushing” or “selling” anything…Every significant creator you know – even those who are maniacally focused on their product or craft – invests disproportionately in cultivating community. None of them just publish and hope for the best.

Look Beyond Launch Day

Once you’ve decided on what your side hustle is going to be, committed to actively working on it, and cultivated a community, there’s going to come a time when you need to put it out there and see what happens. This can be the most daunting step. Maybe you’re worried that nobody will want what you have to offer or struggling with impostor syndrome. Or perhaps you’re concerned that your email list and social media following aren’t big enough. These could be valid concerns, but at a certain point, you have to get beyond them and hit go.

In his book Side Hustle, Chris Guillebeau built on the old adage that “perfect is the enemy of done” and suggested that you iterate on your product after it’s out in the world: “What if you aren’t ready to launch?” he wrote. “Well, you’re hardly ever fully here’s a trick. Go ahead and publish your offer, but add the label ‘beta’ to it. You could also call it ‘early version’ or any other phrase that sounds good. Doing so will allow you to continue working on it while also getting real feedback, and hopefully some sales as well.”

Once you get your side hustle off the launch pad, it’s easy to think of this as an end point. But really, it’s just the beginning. First, keep the conversation going with your customers. In his other book The $100 Startup, Guillebeau suggested that in addition to scheduling an automated “thanks for purchasing” email, you could surprise people with handwritten thank you cards or unexpected bonus content. And don’t consider any launch to be a one-and-done thing, but rather a continual cycle that allows you to solve more problems and build ongoing relationships.

“Start thinking about the next launch,” Guillebeau wrote. “What can you build on from this one? What did you learn that can help you create something even better next time? Remember, many customers will support you for life as long as you keep providing them with great value. It’s much easier to sell to an existing customer than to a new one, so work hard to overdeliver and plan ahead for the next project.”

This doesn’t just apply to products. If you recorded an introduction to wildlife photography course, which additional concepts can you include in a more advanced follow-up? Just published your debut book? Somewhere in it is the big idea for your next one. Once you get to this stage, your side hustle will take on a life of its own and at some point, might even become your main gig.