Chris Guillebeau: Side Hustle Book Summary



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Side Hustle: From Idea to Income in 27 Days by Chris Guillebeau


  • The way of the side hustle: defined as a moneymaking project you start on the side, usually while still working a day job. In other words, it’s a way to create additional income without taking on the risks of going full throttle into the world of working for yourself.
  • But a side hustle isn’t just about putting extra cash in your pocket. In today’s environment, where the idea of a business having any sense of loyalty to its workers has all but disappeared, the side hustle is the new job security. It affords you the ability to decide.
  • When you receive multiple paychecks from different sources, you are no longer dependent on the whims of a single employer. More income means more options. More options mean more freedom.
  • Money does grow on trees – you just have to plant the right seeds, in the right soil.


  • There are very few prerequisites to side hustling. To be successful in using this model, mostly you need.
  • The right frame of mind.
  • The willingness to act.
  • You don’t need much money.
  • You don’t need much time.
  • You don’t need a business degree, or any kind of specialized education.
  • You don’t need employees, assistants, or business partners.
  • You don’t need experience starting a business.
  • Side hustle skills are not taught in school.
  • The only way to master side hustle skills is by doing.


  • A side hustle has many benefits, but it all starts with an idea. This first week of hustling will teach you how to generate business ideas that actually work.

Day 1: Predict the Future

  • A side hustle isn’t just about money in the bank, as helpful as that can be. A side hustle really can change your life. When you build something for yourself, even as you continue to work your day job, you become empowered. You gain confidence. You create security, both in the form of that extra cash and also in the fact that you’re opening up future opportunities for yourself.
  • A side hustle is like a hobby, with one big difference: most hobbies cost money. A side hustle makes money.

Day 2: Learn How Money Grows on Tress

  • Once you understand that money really does grow on trees, the next step is to learn to plant the right seeds. The seeds for a money tree consist of moneymaking ideas. For your tree to bear fruit, you’ll need to put in the work to turn those ideas into action.
  • Almost every hustle idea that’s worth pursuing shares three qualities. You want your idea to be feasible, profitable, and persuasive.
  • A side hustle is something that makes you money, not costs you money. If you don’t see how you could make money from the idea, preferably in a short amount of time, it’s probably not a good idea.

Day 3: Brainstorm, Borrow, or Steal Ideas

  • Everywhere you look, hustle ideas are all around you. Many of these ideas can be exchanged for money. In creating your side hustle, the goal is to turn your idea into an asset, something that has real value and produces income for you over time.

Day 4: Weigh the Obstacles and Opportunities of Each Idea

Day 5: Forecast Your Profit on the Back of a Napkin

  • The secret to turning a profit for any business or venture, boils down to one basic principle: don’t spend more money than you take in. With this principle in mind, the projected profit for just about any hustle can be calculated by the following simple equation:
  • There’s an old joke about a bar in Silicon Valley, the original hub of the startup scene. A bar opens and is wildly popular – sort of. A million people walk into it, but don’t buy anything. The bar then declares massive success, and the founders “exit” by selling their company to a group of investors. It’s a good joke that reflects a very bad business experience. It doesn’t matter how many people walk into your bar; what matters is how many people buy something.
  • Your side hustle absolutely must have a clear plan to make money. Don’t set aside this requirement and decide that you’ll “figure it out later.” That’s fine for a hobby, but not for a hustle.


  • Day 6: Use the Side Hustle Selector to Compare Ideas
  • FEASIBILITY: The ability to begin turning the idea into action in a short period of time
  • PROFITABILITY: The potential to make money from this idea, also in a short period of time.
  • PERSUASION: Not only is this a good idea, it’s a good idea now.
  • To narrow our list even further, let’s add two more qualities to the mix:
  • EFFICIENCY: How quickly can this be executed?
  • MOTIVATION: How excited are you about this idea?

Day 7: Become a Detective

  • As you move forward with an idea, take a look at what other people are doing. Then, do it better – or at least differently.
  • Your reconnaissance mission doesn’t need to be complicated. You just want to learn two things:
  • Who else is offering the same thing or something similar
  • How your idea will be better or different.

Day 8: Have Imaginary Coffee with Your Ideal Customer

  • There’s one person out there who fits the profile of your target customer. What can you learn from them?
  • Every side hustle has a target customer, a specific type of person that its product or service is designed for. Sometimes these target customers are called “avatars,” but you can also just think of them as your people. And the better you can understand those people – who they are, what they need, and where their pains points are – the better equipped you’ll be to serve them.

Day 9: Transform Your Idea into an Offer

  • Once you have a great idea and an ideal customer you need to transform the idea into an offer. An offer has a promise, a pitch, and a price.
  • To have a real-world side hustle, you need to transform your idea into an offer. At a bare minimum, an offer tells people exactly what they will get for their money – and it also usually makes clear how much money is required to get it.
  • THE PROMISE: how your hustle will change someone’s life
  • THE PITCH: why they should purchase or sign up now
  • THE PRICE: what it costs to purchase or sign up (and how to do it)
  • See if you can shift your idea into a simple (yet specific) offer.
  • Your Idea, Your Promise, Your Pitch, Your Call to Action
  • Now put it all together in a couple of brief and catchy lines. Your Offer

Day 10: Create Your Origins Story

  • Like a comic book superhero, your side hustle needs a history. Don’t just tell ‘em the facts; tell them a story.



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Day 11: Assemble the Nuts and Bolts

  • Resourcefulness is your most valuable skill as a side hustler. Get a head start on sourcing everything you’ll need to launch your project sooner rather than later.
  • Get a bank account that’s just for your side hustle.
  • Similarly, get a separate credit or debit card you use only for expenses associated with your hustle.
  • Pay for everything you can up front.
  • Set aside at least 25 percent of your hustle income for taxes.
  • Be fast with invoicing.
  • Whenever possible, insist on a written agreement for service work.
  • Legal structure.
  • Right from the beginning, set up a very simple accounting system.
  • If at all possible, set aside a dedicated hustle workspace.
  • Once you’re making money, pay yourself first.

Day 12: Decide How to Price Your Offer

  • Pricing can be challenger even for experienced hustlers. Use to cost-plus model and follow two simple guidelines to be way ahead of the curve.
  • The first thing to know is there’s usually a range of possible prices you could successfully charge. You want it to be low enough that you don’t turn away or lose customers, but high enough that you can still make money. Assuming you want to maximize profit, your long-term goal is to find a sweet spot at the higher end of what people are willing to pay.
  • Selling a Product
  • With cost-plus pricing applied to a product, you first figure out how much it will cost to provide the product, and then you simply add on a markup (a dollar amount or a percentage) that serves as your profit
  • Selling a Service
  • If you’re providing a service, there aren’t many hard expenses associated with the work. Naturally, this doesn’t mean that she should a charge a low price. Clients pay for skill and expertise, as well as the time you spend on all the tasks.
  • To set an introductory price for a new service, start by deciding on your minimum acceptable hourly income.
  • One good rule of thumb is that your minimum accepted hourly income should be at least what you make per hour in your day job, and probably more. Since you’ll be working on the project in your spare time, the income you earn needs to be worth the leisure time you’ll be giving up.
  • PRODUCT: Minimum acceptable profit per item or per sale.
  • SERVICE: Minimum acceptable hourly income or flat rate.

Day 13: Create a Side Hustle Shopping List

  • Your hustle will probably require specific tools, resources, and deliverables. Learn to find, gather, or create everything on your shopping list.
  • Every side hustle requires some setup work: a list of things you need to either source, acquire, or prepare to bring your offers into the world.
  • Successful side hustlers create or obtain a recipe to take their hustle from idea to implementation. For each step of that process, there will be “ingredients” – the tasks you need to tackle, the resources you need to acquire, or the deliverables you need to produce – in order to complete your recipe for success. The more you can simplify your idea and break down the creation process into clear, specific steps, the easier it will be to get up and running quickly.


  • Just as no two recipes are exactly the same, the recipe for every side hustle is different. Your ingredients may vary from those in these three plans, but here are some common ones.
  • Website, Social Media Profiles, Scheduling Tool, Workflow, Payment System.

Day 14: Set Up a Way to Get Paid

  • You’ve got a lot more than just an idea now-you’re well underway to a real-life side hustle. Before proceeding, make sure you’ve also got a real-life way to get paid real money for it.
  • If you don’t have a way to get paid, you don’t have a hustle.
  • Simple Payment Systems, Paypal and Shopify

Day 15: Design Your First Workflow

  • First create a list of everything that needs to happen along the way. This list is called a workflow. A workflow is simply a series of activities or processes that must occur to complete a project. In the case of hustles, it’s everything that needs to happen for customers to make a purchase and receive whatever they’ve paid for.
  • Create your master list of tasks, actions, and next steps. The more detailed, the better.

Day 16: Spend 10 Percent More Time on the Most Important Tasks

  • Do more of what’s important, and less of what’s not.
  • Two general areas, providing more value and making more money, should be your primary focus as you prepare to launch your hustle.
  • Focus Area #1: Change Your Customer’s Life
  • Focus Area #2: Make More Money
  • Spend 25 minutes a day doing one thing to grow your hustle
  • You need to work smart, not just hard.
  • Doing this first thing in the morning.


Day 17: Publish Your Offer!

  • When’s the best time to get your offer out and see what happens? Usually before you’re ready.
  • By now, you’ve heard me say it more than once: start your hustle before you feel completely ready. Why start sooner rather than later? Well, there are several reasons. The first is proof of concept, the validation that you’re on to something. Even when you feel confident, you never know for sure if your idea is going to work until it comes to life. Therefore, the sooner you can begin to learn how customers respond to it, even if the data is incomplete, the better.
  • Done is better than perfect.
  • Create a Facebook page before making a website.
  • Launch in Beta

Day 18: Sell Like a Girl Scout

  • Even with a great product or service, and a great offer to make your pitch, magic money doesn’t usually fall from the sky. Channel your inner Girl Scout and make some sales!
  • If you’re resistant to sales or marketing in general, remember two things:
  • You’ve put in a lot of work on your hustle. You’re proud and excited of what you’ve made. You owe it to yourself to take the next step to set yourself up for success.
  • The people who need your hustle want to be marketed to! They are waiting to hear about it. If you don’t make it through the noise and reach them, they’ll never have the chance to find out what you’ve made.
  • Lead with benefits, back them up with features.
  • Even the best salespeople sometimes get benefits and features mixed up. Here’s a good rule of thumb: benefits are the ways in which a product will improve someone’s life; features are the details that demonstrate how, Both are important, but if a customer doesn’t believe that your offer will make their lives better, a long list of features won’t help. Always lead with benefits!
  • You don’t want a drill, you want a hole.
  • The drill is just the means to that end.
  • Always think about what people really want and why they want it. With that information in hand, it’s much easier to figure out how to offer them the tools that will help them get it.

Day 19: Ask Ten People for Help

  • Don’t be an army of one.
  • Even though a side hustle can be a solo undertaking, you’re not alone out there, or at least you shouldn’t be. As you launch your new hustle, you’ll want to reach out to a few key people for help.
  • Don’t “spray and pray.” Instead, be specific
  • Just as you’ll be much more successful when focusing on a specific customer group, you’ll also likely see far better results from asking specific people to help you reach those customers.

Day 20: Test, Test, and Test Again

  • When you’re beginning a new hustle, you don’t usually know which approach will be the most effective. To find out, try different things and keep a record of results.
  • You don’t need to test everything. You just need to test the things that matter most. Start with the big stuff! Here are the big three:
  • Your product or service (what you offer)
  • Your offer (how you present it)
  • Your price (how much it costs)

Day 21: Burn Down the Furniture Store

  • Deals, discounts, and special offers are your not-so-secret weapon to encourage customers to purchase. There’s a very good reason that so many stores “go out of business” every three months.
  • Human beings are conditioned to respond to deals. Everyone loves getting something for less. Offering some kind of sale or special offer is perhaps the most effective not-so-secret weapon you have in your side hustle arsenal.

Day 22: Frame Your First Dollar

  • Always celebrate your early achievements. There’s more work to be done, but small victories can be disproportionately satisfying.



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Day 23: Track Your Progress and Decide on Next Steps

  • As you learn more about how customers respond to your hustle, take note of the most crucial metrics – then take action on what you learn.
  • Track what matters, ignore what doesn’t
  • Think about how you track other things in your life, including your health and personal finance. At any given time, do you have an approximate idea of how much money is in your checking account? (Most people do.) What about your health – how do you feel right now? (It’s another easy question.) For each of these areas you could collect all sorts of other data, but by answering these two simple questions the big picture is easy to discern. That’s how it should be with your hustle: at any given time, you should know its general health and well-being. This isn’t hard when you keep up with your metrics in three key areas:
  • Profit (income minus expenses)
  • Growth (number of new prospects, customers, or clients)
  • Time (how many hours per week you spend starting and operating the project)
  • At the end of the day, you’re really just looking to answer one simple question: Is your hustle profitable? Yes, there’s more than one way to measure success, but your side hustle should make money.

Day 24: Grow What Works, Let Go of What Doesn’t

  • As your hustle grows, there are countless options to expand. Don’t get distracted – identify what’s working and do more of that.


  • Regrouping and refining are the superhero skills of side hustle success. Consider this quote from Bill gates: “Headlines are misleading. Bad news is a headline, and gradual improvement is not.” Tracking, testing, and refining are all about achieving gradual improvement. You might not make a lot of fanfare when you gradually improve an existing hustle, but you’ll probably make more money.
  • Iteration means “the act of repeating a process.” Usually with the goal of improving each step along the way. As you continue to develop and improve your hustle, follow these two basic rules of iteration:
  • If it works, do more of it.
  • If it doesn’t work, abandon it and move on.

Day 25: Look for Money Lying Under a Rock

  • One of the easiest ways to grow a hustle is by horizontal expansion. If everything’s going well, consider adding another version of it to better serve your customers.

Day 26: Get It Out of Your Head

  • Every business has key systems. As a side hustler, yours are probably stored in your head-and that’s not always wise. To make significant improvements (and save more time) as you expand your hustle, systemize wherever you can.
  • The two most important workflows for most hustles are sales and service. Basically, you want to document how you sell to people and how they receive what they purchase.

Day 27: Back to the Future

  • You’ve come to the end of the road…or is it the beginning? Side hustles create opportunity and freedom. Once you’re up and running, your options are unlimited.
  • Here’s the thing about a good side hustle. It can help support your life, but it doesn’t have to be your whole life. In fact, thanks to the project they’ve built, most side hustlers are able to enjoy more of their life.
  • Always remember that a hustle is different from other startup ventures or businesses. You don’t have to listen to the advice of experts or follow conventional wisdom. You don’t have to “scale.” You don’t have to hire employees or assistants, virtual or otherwise. There is no single “right way.” There’s only the right way for you.
  • The side hustle economy is here to stay. It’s a social revolution that can improve out collective well-being and broaden our cultural approach to work. From security to extra income to confidence to fun, there are many benefits to a hustle. And when you start quickly and keep costs low, there’s very little risk. What will your story be?




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