How to Choose a Side-Hustle

How to choose a side-hustle
How to Choose a Side-Hustle

How to Choose a Side-Hustle

There’s never been a better time to start a side-hustle. There are more opportunities, more tools, and lower entry costs than any time in history. You don’t have to settle for your current life any more.

With a side-hustle it doesn’t matter where you grew up, or how your parents raised you.

You can literally start (and operate) an entire business from your phone (if you wish) and never have to meet a customer.

I operate an international publishing business in 80 countries and I’ve never met one of my customers. I operate my little side-hustle from my pocket too.

There’s a dark side too.

Not the dark side where people might take advantage of you when you’re new (sure, that exists too), but the dark side where you freeze.

I get emails from hundreds of indie entrepreneurs and many of them write a rendition of the same email.

“I don’t know where to start. I’m totally overwhelmed.”

Instead of searching for the right side-hustle for the person, these folks give up before they start. They’re buried in over-choice. They see an Instagrammed version of entrepreneurship, feel left-out, and wonder what’s wrong with them.

There are fewer choices than you might think.

Once you work your way through the decision criteria, you can uncover your own side-hustle. One that closely-matches the person behind the work.

Instead of focusing on the person you aren’t, we’ll go after your strengths and build a side-hustle around the person you are.

First, We Sort What We Don’t Want

The first step of choosing a side-hustle is to sort what you don’t want. We know what we don’t want. We bump into these annoying tasks and projects daily. Why design a new business doing work you hate?

Uncovering what you don’t want is more important than what you do want. It’s also easier than trying to pick what you want from the air.

Make a list of ten criteria you don’t want in a side-hustle.

  • Maybe you’re an introvert and you don’t want to speak to people in-person
  • Perhaps you can’t imagine sitting at a desk all day. You’d rather get out and move-around
  • Or maybe you don’t want to sell a physical product. You like the idea of location independence

All these criteria are critical to your well-being later.

Remember, most of us choose a side-hustle to escape our current situation, not to make life worse. It’s important we start with the person we are and the person we aren’t.

  • If you’re an introvert and you hate the idea of face-to-face selling, don’t become a consultant or salesperson.
  • If you’re an extrovert and the idea of sitting and writing for long periods of isolation feels like a punishment, maybe it’s not a good idea to become a writer.
  • Perhaps you hate your day job. You can’t imagine spending another day performing a certain task (such as “I despise weekly meetings more than anything”). Add the things that make your skin crawl.

Don’t be a baby, either.

You’ve got a list of ten items. Only add an item to the list if it’s a deal-breaker. Side-hustles require perseverance and hard work, no matter how much you love the work. This list isn’t a place for complaints, only absolute noes.

Now, Sort What You Do Want

I’m sure you’ve got a general direction of an idea for your business. This is a good place to start.

Make a list of the top five things you want in your side-hustle. These can be as specific or general as you’d like.

  • What kind of an environment do you want to work in?
  • What kind of customers do you wish to serve?
  • Is there a particular niche you can’t stop talking about (you really like trains, for example)?

Some people struggle here. They’ve never had the opportunity to design their own lives. For them, I recommend the Ten-Year-Old-Test.

Think of the behaviors you enjoyed when you were ten.

What were you doing that grabbed your focus so much your family practically had to drag you by your feet to get you to the dinner table?

As we age, we don’t change as much as we think. You might not collect rocks or jump in puddles, but there are certain environments and behaviors you enjoyed then, that you’ll probably enjoy them now.

Design your work around these behaviors.

Choose a Proper Side-Hustle for You

I went after the wrong hustles for years before I used this process to uncover the work I love. Now I write every day and get paid well doing something I love. I write every day and it doesn’t feel like work.

When I have to do the less-fun parts of my business I always reflect on how lucky I am to have designed the business I did. I enjoy the majority of the work, because I removed the parts I don’t want to do.

We can’t run from the person we are inside. Yes, you can force yourself into work that isn’t meant for the person you are. Some people are able to do well, despite the inner-conflict.

But you’ll feel there’s something wrong.

If you have the choice, it’s best to match who you are with what you do.

Plus, there are so many choices for side-hustles, this exercise will help you narrow the field. A lot

Now you have a list of what you do want and what you don’t want. I hope you’re at a place where you also know the tribe you wish to serve. These are the people who will eventually love your work.

You’ll design your business to serve these folks. No one else.

Instead of guessing what these folks want, we’ll ask them. Later, we’ll build them what they want and we’ll sell it to them.

There are many ways to ask your tribe what they want. You can do it directly, by build an email list of people in the tribe you wish to serve.

If you don’t have an email list, you can read hundreds of online reviews for products in your niche. Notice their language. Find unmet needs. Look for common themes.

Holes in the marketplace leave clues.

You never want to build a product first, then search for customers to buy it. Yet, most side-hustles are started this way. Your business doesn’t have to be trial-and-error.

By asking what you tribe wants, then giving it to them, you’re more-likely to build a successful business.

Now, you can’t ask your tribe what they want. Not directly. Instead, we ask them what they don’t want in their current situation. I did that with this article. I also use the same method with my publishing business.

By asking people what they don’t want, they will lead you to what they do want.

It’s your job as an entrepreneur to build the solution that gives your tribe the transformation.

What’s a transformation?

The best products transform their audience from the life they have now (the situation they’d like to escape from), to the life they want (the place the customer wants to arrive).

Engineer Your Future Life

When find the sweet-spot, that synergy comprised of what you don’t want, what you do want, and what your tribe wants–you’ll find your side-hustle there.

These little pockets of commerce are everywhere.

New technology brings with it new support businesses.

If you don’t like your current situation, don’t build a new side-hustle with the same components. You can literally build any business you wish. You might as well build one you love.

This is how you create your work–the stuff that makes you smile when you talk about it. Even when the days are hard, when we do our work, they’re a hundred-times better than the good days at a job we hate.

Our job is what we do, but our work is who we are.

Remember that.

You have a chance for your inner life to match your outer life.

How much time do you want to/can you spend on your side-hustle every day?

Maybe you have a busy life. You’ve only got 30 minutes in the morning, or 20 minutes at lunch. Cool. Don’t try and build a car dealership. Develop a digital product instead. Maybe launch a course. Work on one module per day until it’s done.

There are no rules when it comes to side-hustles.

Most of the tools are free, or inexpensive. For a few hundred dollars you can operate an international business from your pocket (just like me).

Uncover what you want and don’t want in your side-hustle. Find a group of people you want to serve. Ask them what they want. Give it to them. We learn from our mistakes. We change-course. We try again.

The hard part is starting.

You won’t get everything right on day one. You can always tweak your product and your process later. Everything is adjustable.

Avoid the side-hustle overwhelm and choose a business that fits the person you are. Maybe you won’t notice the benefits on the good days, but when the struggle comes, you’ll appreciate doing work you’re designed to do.


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August Birch is an author, email expert, and entrepreneur from Michigan, USA. As a self-appointed guardian of writers and creators, August teaches indies how to make more work that sells and sell more work once it’s made. When he’s not writing or teaching, August carries a pocket knife and shaves his head with a safety razor.

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