Book review – Side Hustle: From Idea to Income in 27 Days

Product: Side Hustle: From Idea to Income in 27 Daysside-hustle-cover

Author: Chris Guillebeau

Hardcover: 272 pages

Publisher: The Crown Publishing Group

ISBN: 978-1524758844

Price: $17.00 (retail)

Cheapest Place to Buy: Amazon.com

Product Dimensions: 5.8 x 0.9 x 8.5 inches

Shipping Weight: 13.4 ounces

My Rating: 8.5 out of 10

Side Hustle: From Idea to Income in 27 Days, Product Overview

This book by Chris Guillebeau, author of the New York Times bestseller The $100 Startup, provides a step by step approach to identifying and operating a profitable side hustle. It defines a side hustle as “a moneymaking project you start on the side, usually while still working a day job”. That is to say, a way to earn some extra money without having to give up the security of your current employment.

The book is divided into five sections, roughly equivalent to one week each. However, some weeks have five days and some have seven, resulting in a total of 27 days as described in the book title. The sections are:

  • Week 1: Build an Arsenal of Ideas
  • Week 2: Select Your Best Idea
  • Week 3: Prepare for Liftoff
  • Week 4: Launch Your Idea to the Right People
  • Week 5: Regroup and Refine

There is also an additional section at the end of the book called Kitchen Sink. It is a list of resources to further your learning, including:

  • Side Hustle Starter Kit
  • How to Validate an Idea with $10 and a Facebook Account
  • Write a Letter to your Ideal Customer
  • Buy a Rental Property with a $1,575 Down Payment
  • Resources and Free Stuff

So, let’s go through and review each section of the book. Much of the content is anecdotal, relating stories of people who have acted on that section of the book to develop their own successful side hustles. I will not review the merits (or otherwise) of these side hustles but will look at the steps required to make your side hustle happen.

Week 1: Build an Arsenal of Ideas

The objective of the first week is to learn to generate ideas. It consists of 5 daily tasks that will teach you how to generate great side hustle ideas that can create additional streams of income.

The first day is an exercise in framing how your mindset will change as you work through the 27 steps.

The second day looks at the 3 qualities of a great idea:

  • is your idea feasible?,
  • is your idea profitable? and
  • is your idea persuasive?

On the third day, your task is to use what you have learned about high-potential ideas to brainstorm three potential side hustles.

The fourth day is an exercise to understand the pros and cons of each these ideas.

Finally, on the fifth day, you are shown how to estimate the profit of your side hustle on the back of a paper napkin.

By the end of the first week, you should have several potential side hustles in mind. You should have weighed up the pros and cons and the profitability of each one.

You are now ready to decide which one you will turn into action in Week 2.

Week 2: Select Your Best Idea

The objective of the second week is to select your best idea, as not all ideas are created equal. The week again consists of 5 daily tasks, this week focusing on how to rank and compare ideas to maximize your chance of success.

The sixth day is an exercise in ranking your three potential side hustles, based on the qualities of a great idea. An additional 2 qualities are presented:

  • how quickly can your idea be executed?
  • how excited are you about this idea?

On the seventh day, your task is to become a detective and see how other people are using this idea. How can you do it better or differently?

The task for the eighth day is to determine the profile of your ideal customer and what you can learn from them.

Your task on Day 9 is to transform your idea into an offer. An offer consists of a promise, a pitch and a price.

On the final day of Week 2, you need to create a great origins’ story; “a compelling and inspiring narrative of the why” behind your side hustle.

So, by the end of the second week, you should have a firm side hustle idea that you have transformed into a full-fledged offer. You are now ready to dive in and get your offer up and running in Week 3.

Week 3: Prepare for Liftoff

The objective of the third week is to prepare to share your best idea with the right group of people. Week 3 consists of 5 daily tasks and an additional bonus task. It focuses on how you will get your ideal customer understand why they can’t live without your offer.

Day 11 looks at the resources you will need to make your side hustle work.

On the twelfth day, you will determine the price of your offer. You will use a cost-plus model and follow 2 simple guidelines to assist you.

On the thirteenth day, you will learn that your side hustle requires some specific tools, resources and deliverables and where to get them.

Day 14 is a lesson on setting up a way to get paid for your offer.

Your task for Day 15 is to list out an orderly workflow for the launch of your side hustle.

Finally, there is an additional bonus task on Day 16 which relates to time management and concentrating on just two things; changing your customer’s life and making more money.

Now that you have a solid offer to present to your customer, it is time to move on to your launch in Week 4!

Week 4: Launch Your Idea to the Right People

The objective of the fourth week is to launch your best idea (probably before you are ready) and track your results. Again, the week consists of 5 daily tasks and an additional bonus task.

It is now Day 17 and time to take your offer into the world.

Even with a great offer, money or customers won’t automatically fall from the sky! Your lesson on the eighteenth day is to channel your inner Girl Scout.

On the nineteenth day, you will learn that as you begin hustling, it is OK to call on friends and supporters to get the word out.

Day 20 is a lesson on testing your side hustle. To find the most effective approach, try different things and keep a record of the results.

Day 21 looks at the benefits of deals, discounts and special offers to drive more sales.

Your bonus task on Day 22 is to take time to celebrate your initial achievements. Stop and smell the roses!

Week 5: Regroup and Refine

The objective of the final week is to refine the process and see what can be done to raise the game. Success is now within your grasp and you have 5 final daily tasks.

On day 23, you will learn to track your progress through several key metrics and then to take action based on them.

Day 24 is a lesson on identifying what is working and what is not, and then focusing on the winners.

Day 25 considers adding another expanded version of your side hustle to better serve your customers, if the offer is going well.

Every side hustle has key systems which you probably keep in your head. Day 26 looks at making your business work a lot better by using a system-based, process-driven approach.

It is now finally Day 27 and the finishing line is in sight………or is it just the beginning of something much bigger? Side hustles create the opportunity and freedom to do whatever you wish with your future and the options are unlimited. You can stop at one and say you are finished or you can move on to the next one and start from Day 1. It is your choice!

Have I read the book? What do I personally think of it?

Every time I need to re-energize my brain and it’s quest for new knowledge, I read this book. So, I have read it many, many times!! Not so much for the steps, but to admire the successful side hustles achieved by other every-day people. People just like you and me.

What do I think of the book?

Side Hustle: From Idea to Income in 27 Days is a great read if you are just starting out or still considering a side hustle. There is not much detail in any of the steps and you will still have to look elsewhere to fill in the gaps. I plan to post additional articles covering these gaps over the coming weeks.

I would not consider this a 27-day plan by any stretch of the imagination; it is a stepped approach to taking an idea through to a successful side hustle in a time frame only you can choose (as it will depend on your experience and the amount of time you can dedicate to it).

Do not feel pressured to do all this in 27 days. Creating a side hustle is supposed to be fun. Stress is NOT fun!

I have read a number of reviews on Amazon that complain there is too much fluff in the book. While I assume they are referring to the anecdotal tales which make up a large part of the book, I actually think these will help a less experienced person understand how the steps work together to bring the finished offer together.

They are also a great source of ideas for generating you own side hustle ideas. After all, if they already work for one person, you may be able to create a side hustle to do it better or differently.

Overall, the book’s concept of taking an idea and monetizing it into a solid offer to present to your customer is sound. If you follow the steps in the book, you can create a side hustle that will generate additional income for you.

Take action. Buy the book and start your own side hustle.
Update 19-Jan-2019

If anybody would like to listen to the Side Hustle School podcasts for a bit of inspiration, you can go to the website here.

Was this helpful? Share it with your friends. After all, they also deserve the fine things that life has to offer.



  1. I think his would be such a helpful read for me as I have 2 side hustles going on at the moment. It would especially be helpful for me to read the bit about picking the right audience, as I think thats quite difficult to know who you are targeting with your work. 

    • Hi Jayde and thank you for your comments.

      I agree that many times we forget the basics and start writing the article or pitching the offer at ourselves, rather than the actual person who will buy our product or service.

      By focusing on your ideal customer and writing directly to that person, you build a stronger bond. This bond is what makes a person buy from you.

      Wishing you all the best with your 2 side hustles in 2019 and beyond,


  2. When I started reading this book review I was thinking i was going to get tired of reading it but it turns out this book is going  to help a lot of people set their record straight, this book is surely recommended for anyone who want to be successful in whatever he or she has got to do, I like the fact it comes with an inspiration of his own. Thanks for tis review once more

    • Hi Seun,

      Thank you for your comments.

      Although the book is quite basic, it does have a lot of useful information on the steps needed to set up a side hustle. The examples are great if you are having trouble figuring out an idea for your hustle.

      I would recommend the book to anybody just starting out or to somebody that needs inspiring to take action.


  3. Everybody should have a side hustle, it keeps things interesting and exciting, also some side hustles earn good money and could become your full-time business.

    I have begun so many side hustles, mostly I break even and don’t really earn much. but you never know which side hustle is going to take off and make you a successful businessman or even better retired.

    This looks like a pretty cool book, all these kinds of books are worth reading, they help inspire us, get our imaginations working and can teach us some really practical steps to success.  You will be amazed by the books you read and the inspiration you can take from these.  

    You never know what will spark your next idea or side hustle.  One thing I know you won’t find it if you don’t go looking. I will continue searching for my perfect side hustle.  Thanks for sharing this book with me.

    I might go and grab a copy! Cheers.

    • Hi Kris,

      Thank you for your comments on my post.

      The great thing about side hustles is they usually don’t cost you much more than your time. So, if something doesn’t work out, put it down to experience and try something else. In terms of money, you probably haven’t lost too much.

      As you say, you may go through a few or a lot of hustles before you find the one that is right for you. That is one of the reasons why I like this book. It provides so many examples of what you can do or do differently or do better. Go through the checklist to determine if it is an idea worth following up or if there is something better.

      I recommend reading it if you get the chance. It may not have a lot of informational content on the individual steps, but it will point you in the right direction.

      Best wishes on finding your perfect side hustle,


  4. Hi Gary,

    Thanks for providing this review of Side Hustle, it sounds like it sets out easy to follow steps for getting the foundations of a new business in place. I like the fact that they use real life examples, it helps you visualise how you can do it for your own business. The author is obviously American, would you say this book will related to other global territories?


    • Hi Nate,

      Thanks for your comments.

      The book is quite easy to follow due to the step approach (days and weeks) that is used to set out the learning. A number of reviews have been critical of the lack of information within each step and I agree that you will have to search further than the book to fill in all the blanks. Some reviewers have called the real-life examples “fluff” but I agree with you. They do help in generating ideas for your own business.

      Chris Guillebeau is an American but the method he teaches will work in any country. For example, people in Somalia have mobile phones and phone payment systems, so there is no reason for you not to promote an e-commerce product to them (or for someone there to promote to you!). Delivery may be an issue but they will find a way! Or a student in China that would love to subscribe to your English tutoring website. So many options.

      Thanks to globalization and the huge audience provided by the internet, there will always be a side hustle that will work for you, no matter where you are. (I am currently replying to you from northern Myanmar)

      Make the decision to start a side hustle and take action based on the steps in the book. You will not regret it.

      Best wishes,


  5. This is a brilliant review of what appears to be a fantastic book! I think that  I like the fact that the process is broken down into manageable pieces that are carried out every day and every week. This is a great way to make sure that you succeed and actually follow the steps rather than just quitting.

    I think this a  great plan for a great reason. A side hustle is great for expressing your creativity and individuality as you bring your perspective and ideas together. It is great that you can help someone by providing a good or a service but can also make money at the same time. It is a win-win scenario.

    Thanks for sharing this great book!

    • Hi Renton and thank your for the comments on my article.

      I am glad that you liked my review.

      By breaking the process down into daily(?) steps, it makes it easier to take small actions regularly, rather than having a huge task to complete which may turn people off from the idea of starting.

      Having one (or several) side hustle is a great way to grow your money tree. By having more than one source of income, you are not totally dependant on your boss. But, it still gives you the security of having full-time employment. It also provides you the option of ramping up the efforts on your side hustle and making this your full-time job and getting out of the 9-to-5 grind.

      If you are interested in setting up your own side hustle, I would recommend you read this book.


  6. Hey Gary,

    Thank you for reviewing this great book – Side Hustle

    I love the real-life stories in this book about people making money with their side hustle, breaking out of ruts, and improving lives. It’s so doable. 

    Chris sets out very precise and clear steps to follow day by day. I’ve had an idea for more than 6 months, no follow-through. I’ve made more progress in the last 2 days than I did in all 6 months. I also listen to Side Hustle Podcast.

    This book is an excellent investment for anyone with even a glimmer of an idea. Or if you don’t have an idea, but you’re dissatisfied with the status quo. Or you’ve got a yearning to expand beyond the 9-5 rut–without giving up the security of your day job.

    Best wishes

    • Hi Zeyn,

      Thanks for your comments.

      I couldn’t have said it better myself. The real-life examples help me relate to the method behind the steps, even though other reviews have called this “fluff”. I disagree. I think it is very helpful in generating ideas for your own side hustle.

      The Side Hustle podcasts are another great inspiration for ideas. Some, though, are way out there but if they can make them work, congrats to them!

      I am currently contemplating setting up an e-commerce shop and have run my idea through Chris’ criteria for a good idea and it ticks all the boxes. I will get back to you all with a new article on this soon.

      Best wishes for 2019,


Leave a Reply

Your email address will not be published. Required fields are marked *