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How to Side-Hustle Your Way to Wealth

Discover reasons for getting a side hustle and steps for starting it


There is security in having a job, especially if it pays relatively well. However, John Augustus Shedd once said: “A ship in harbor is safe, but that is not what ships are built for.” Hence, if you have an adventurous or entrepreneurial streak, sitting behind a desk all day is counterintuitive. In fact, the chances are that several years down the line, you will regret the opportunities you did not take.

Understandably, you cannot up and quit your job. However, you can find ways to preserve your job’s security while indulging your creative side. That is done through a side hustle.

In this article, we will show you the tips and tricks of starting a side business. We will be drawing inspiration from Chris Guillebeau’s fantastic book, From Idea to Income in 27 Days. And when you don’t have the time to dig into the book, the Headway app steps in to help. You will find a summary of Guillebeau’s book, as well as thousands of insights on Business&Career and other topics there. What is more, Headway summaries take 15 minutes or less.

And now, let’s dive into the intricacies of side-hustling!

Four reasons for getting a side hustle

No job is so great that you would not need a secondary source of income. There is always an incentive to do something else apart from your primary job. Here are at least four reasons to get a side job:

1. Higher income

Perhaps, the most persuasive incentive for doing something on the side. With a side hustle, you can generate a new source of revenue/income to afford and save more.

“Good things happen to those who hustle.”

Anais Nin

2. It creates an opportunity to put your skills to work

Unfortunately, if you work in some spaces, you may feel stifled. You may not have the room to flex the full extent of your skills and potential. If you have a skill that you want to keep alive, monetizing it is the way to improve it. You have more incentive to put your learning to work when some pay is guaranteed at the end of the day.

3. It mitigates uncertainty

Even though you have job security right now, you cannot always count on that being the case in the future. Due to the COVID pandemic, the world has realized — nothing is certain. Thus, having a second source of income serves you best. Even if something changed and you found yourself without your primary source of income, you could always fall back on your side job. These days, the only job security you can count on is the one you give yourself.

4. It makes it easier to transition

The world is slowly tilting towards entrepreneurship. Paid employment often proves insufficient to satisfy the needs of the average person. In fact, if you look closely, you would realize that most of the wealthiest people on the planet are self-made.

Even if financial success is not your motivation for going solo, you may want to tow this path for other reasons. For instance, you may want the freedom and flexibility of being your own boss. You may be attracted to the idea that your income would totally be up to you. While self-employed, you can scale up your income. You would be unable to do this if you were in paid employment. It is easier to transition from paid employment to full-time self-employment if you had a side job from the start.

Four baby steps to start your side hustle

If this is your first time starting a side job, you may be unsure of where to start. Not to worry, Chris Guillebeau has all the answers. Guillebeau has quite the experience in the industry. He has helped quite many folks successfully kick off their side jobs. In his book, Side Hustle: From Idea to Income in 27 Days, he outlines steps to starting a successful side hustle. The steps are:

✅ Step 1: Build an arsenal of ideas

This is pretty straightforward. You need to create a list of the ideas you can turn into a business. If you think you have no viable skill that you could turn into a side job, you are most likely mistaken. First, write down a list of your interests. Then, see if there is a common thread, and start from there.

Guillebeau suggests that you poach some ideas if you haven’t got one yourself. The chances are that you have a friend who really hasn’t committed to a side hustle they have been talking about for the longest time. Help them actualize their dreams by taking over their plans. If anything, they would be living their dreams vicariously through you.

✅ Step 2: Select your best idea

Now that you have a bunch of ideas to choose from, settle on one. You should know from the start that not all of your beautiful ideas will eventually work out. They may look good on paper but are actually untenable. One way to test your idea is by pitching it to family and friends. Their reaction can help gauge whether you would likely make gains or losses if you eventually ventured out.

✅ Step 3: Prepare for liftoff

This is also another crucial point that Side Hustle elaborates on. Once you’ve decided on a gig, make plans to take off. If you want to start a freelance writing agency, check out how others are doing theirs. If you are looking to drive an Uber on weekends, make arrangements for how that will work. Assess the risks, strengths, and weaknesses of your proposed product or service. When you are confident that you are ready, then launch out. How about if you are never sure you are ready? Well, when you are ready, you will know.

✅ Step 4: Launch your idea to the right people

It is crucial to start as soon as possible. Delaying could be because you are afraid of failing. Hence, plodding in nonetheless would be a great way to deal with the fear. Once you begin, do not pull back. Face the challenges when they arise. Do not give up regardless of how tough the terrain becomes.

__“What would you do if you weren’t afraid?”

Sheryl Sandberg

In the last chapter of Side Hustle, Guillebeau teaches that you ought to pause after working for a while and take stock of how far you’ve gone. During these periodic checks, you can ask for your customer’s opinions and suggestions. However, do understand that the pause is not infinite. As soon as you have re-strategized, move on.

In this volatile world of ours, consciously creating some sort of security should be everyone’s goal. Specifically, security is something a side hustle gives you. In addition, it brings you happiness, fulfillment, and contentment. If you are unsure about how to turn your passion into profit, this article shows you the steps to do so. Do not forget that you can always take a refresher course by running through Chris Guillebeau’s book, From Idea to Income in 27 Days, on the Headway app in 14 minutes.

“The best time to start was last year. Failing that, today will do.”

Chris Guillebeau


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