Side Hustle: From Idea to Income in 27 Days

Side Hustle

Summary of “Side Hustle: From Idea to Income in 27 Days“ : Turn your passions into income streams without the need to leave your main job: all this is made possible thanks to this system that will help guide you step by step in your new life as a Side Hustler!

By Chris Guillebeau, 2017, 272 pages

Original title: Side Hustle – From Idea to Income in 27 Days

Note: This is a guest column written by Dimitri Carlet from the site Side Hustle France

Chronicle and summary of the book Side Hustle”

If you prefer video to print, I have prepared an illustrated review of the book How to make full use of your potential on video🙂:


A bit more work than a “part-time job” and less than a start-up, a Side Hustle means that you develop a sideline activity alongside your paid job, your studies or your main business:

  • Either to help pay for stuff at the end of the month but retain the security of a paid job,
  • Or to try out a business idea but not have to spend too much, nor take too many risks.


Chris Guillebeau was born in 1978 in the United States. A traveller, entrepreneur, author of several best-sellers on the subject of personal development and entrepreneurship, he is the founder of the Side Hustle School and hosts a daily podcast about the success of entrepreneurs and how they transform their ideas and passions into a source of extra income.

Notably, he is the author of the book “The $100 Startup” released in 2012 in which he initially presented the concept of the Side Hustle based on successful entrepreneurs he met on his travels (he visited every one of the 193 countries around the world).

Chris Guillebeau didn’t come up with the concept of Side Hustle, but he’s certainly one of the writers who made the term so well-known in the USA. In his book Side Hustle, Chris Guillebeau takes the reader by the hand and gives them a step-by-step, risk-free method to turn an idea into additional income.

The book is laid out in the form of a 27-day challenge and the same number of chapters spread over 5 weeks / sections:

  • 1st Week: generate as many ideas as possible,
  • 2nd Week: choose the best ideas,
  • 3rd Week: prepare for your launch,
  • 4th Week: launch and promote,
  • 5th Week: assess results and make final decisions.

Each day of the 27-day challenge provides the reader with a step-by-step explanation of how to develop a Side Hustle type activity (a concept explained in the first chapter). As usual, each chapter begins with an example of an entrepreneur and focuses on a particular point in their success story.

Day 1: Plan for the future

This gives you an introduction to the concept of Side Hustle. The primary purpose of a Side Hustle is to build up additional income. For some, the goal will be to supplement their income to increase their standard of living; for others, the goal will be to change their current paid job so that they can devote their time to what they are really passionate about. A Side Hustle can also be used to help fund your retirement, for a personal project, or to help support a charity.

Side Hustle passion

Chris Guillebeau’s vision is that with the creation of a Side Hustle, you give yourself a great opportunity to improve your skills, increase your motivation and become more independent.

Day 2: Work out the basic outline of a good idea for a Side Hustle

The first step is to choose the ideas that show the most promise and ask yourself three questions:

Is your idea easily achievable? It must generate a quick and manageable return on investment in addition to your core business. You must be able to quickly put your plans into action, consider the necessary steps and what needs to be done next. If you fail to see a straightforward way to get paid or if you need three years to get it off the ground, scrap the idea. You need to be able to get your idea off the ground with the skills, time and resources available to you.

Is it profitable?

It might look great on paper, but your idea has to be profitable. If you can’t articulate the main benefit to the client within a sentence or two, it may indicate it’s a bad idea from which you won’t make any money.

Is it relevant?

It’s not just that the idea is a good one, even if it is potentially very profitable. Your idea needs to be available at the right time and be so persuasive that it is difficult for customers to say “no”. Concentrate on the ideas that are most relevant now and leave the others for later.

Below are what C. Guillebeau thinks are the hallmarks of “typically bad” ideas:

  • A great vision that is hard to turn into reality,
  • You have no idea how to start and progress from the idea to the plan of action,
  • Your idea involves skills you don’t possess,
  • You have no idea who the potential customers are,
  • Too much work and complexity to manage on a daily basis,
  • Your idea would need several months to build up and launch.

On the other hand, the qualities below might indicate that your idea has all the characteristics needed for a successful Side Hustle:

  • There is a quick and easy way for you to earn the initial additional income,
  • Your idea solves a problem or makes a potential customer’s life easier,
  • You can easily envisage the next steps required to move ahead quickly,
  • You possess all the necessary skills or know a quick way to learn them,
  • You’re passionate about the subject,
  • You don’t need a lot of time or other resources to launch it and monitor it daily,
  • It’s straightforward to manage this activity on top of your core business,
  • You are able to clearly explain the main benefit to potential customers in a sentence or two,
  • You can generate regular and reliable additional income from this idea.

Day 3: How to come up with ideas

The ideas for Side Hustle are everywhere: to work them out, whenever you are with groups of people ask yourself what they want and need.

There are three main categories of Side Hustle: to sell a product, to provide a service or to act as a broker.

Chris Guillebeau introduces the concept of the Higher-Level Idea. Often, the first idea of Side Hustle works but what you earn from it is proportional to the amount of time you spend on it. It’s good to get started, but from there you can take it to a higher level to overcome that limitation.

Side Hustle passion

To demonstrate this point he gives the example of a “Hustler” who began as an Uber driver, then moved up to the next level and taught other Uber drivers and started to blog on the subject:

  • Start-up idea: Driver for Uber,
  • Higher level idea: Coach other Uber drivers and then earn money through a blog on the subject.

If, after the first three days, you have no thoughts on a Side Hustle, Chris Guillebeau suggests a few ideas for you:

  • Sell your works of art, or any craft on
  • Offer online courses in the field of your expertise,
  • Create and sell a tourist guide of your city, financed by advertisers,
  • Publish a blog with a new lesson on a specific topic every day,
  • Start a podcast and get clients to advertise on it to earn money,
  • Visit sales depots and buy items which you can then resell,
  • Become a management coach (personal, office or life coach),
  • Offer small businesses the opportunity to manage their social networks,
  • Offer your services as a freelance writer,
  • Create a website with a fee-based member’s area to access useful information on a specific topic,
  • Write and publish a book.

Day 4, 5 and 6: Choose your idea

It is important to weigh up the pros and cons of each idea before you launch yourself into the project. Chris Guillebeau provides these questions to help you do this:

  • What are the business opportunities linked to your idea (e.g. exists overseas and not in the US, a skill unique to you, etc.)?
  • How much will it cost you?
  • What are the major challenges to overcome? What obstacles may be in your way?
  • How easy will it be to make your first sale?
  • What are the key steps required to launch your idea?
  • Does anybody already offer a similar product or service?
  • If all goes as planned, what will the ideal scenario be?
  • If things don’t go as planned, what is the worst-case scenario?
  • Best potential profit (income – expenses) optimistically?
  • Most pessimistic profit forecast?

Once you have addressed the above questions, all that needs to be done is to assign a Low, Medium, or High rating to each of your Side Hustle ideas based on the criteria below:

  • Feasibility (how quickly the idea can be turned into practice): Low / Medium / High
  • Profitability (potential for quick, repeatable and passive gains): Low / Medium / High
  • Conviction (the right idea at the right time): Low / Medium / High
  • Efficiency (speed of execution and follow-up): Low / Medium / High
  • Motivation (how passionate you are about this idea): Low / Medium / High

Choose the idea that seems like it will produce the best results and act on it!

If there are a few ideas and you are still undecided, go with the one that could produce the most extra revenue: A Side Hustle is not just a hobby!

Day 7: Online comparison

So, you have chosen your idea for a Side Hustle, perfect! Now take a look at what other people offer within the same category and collect as much information as possible that will be useful for your project:

  • Visit their website and look at what they publish on their social media networks,
  • Read what their customers have to say,
  • Test their product or service to see if you need to change your approach.

What are the strengths and weaknesses of competitive products and services? What can you improve or how can you distinguish yourself from others?

Your product or service doesn’t have to be better from every single angle, just one or two changes could suffice for now.

Days 8, 9 and 10: Identify your ideal customer, draft your proposal and create your story

On days 8, 9 and 10 you can turn your idea into reality. To develop it, Chris Guillebeau proposes that you have coffee with a potential target client (or avatar) and then send them a proposal.

Picture your ideal customer as someone who desperately needs what you will have to offer, and define their profile:

  • Who are they?
  • What do they need?
  • What problems do they currently have?

Write down what you imagine their daily routine to be and the problems they face, in detail. Send them a direct message to clarify how you can help to solve the problems they have. You can use this detail to develop your proposal and business description when you launch your product.

Now is the time to turn your idea into a product. The different components of a product are as follows:

  • The Promise: how your Hustle will change the life of the ideal customer. A brief and bold statement that highlights the instant benefit to your customer.
  • The Pitch: the reason why your customer should buy or sign up and why they should do it now.
  • The Price: the cost to buy or sign up (and how to). The details of your product or service, and, finally, a very clear call to action: click on this button, register here, …

Draft your proposal:

You know that your proposal will make people’s lives better. Enthusiasm is contagious, so make it obvious and use these rules:

  • Write to a specific person, not a group, use dynamic phrases and word it in a style that is fun, energetic and enthusiastic,
  • Get to the point and eliminate unnecessary words,
  • Use numbers as much as possible,
  • Put forward positive sentiments: joy, amazement, reassurance,
  • Use testimonials (social evidence).

Lastly, create your narrative and write a story that addresses these questions:

  • Why did you decide to start this Side Hustle?
  • What was your inspiration/motivation?
  • Why this idea and not something else?

This will help you to introduce yourself and should ideally be included on the “About” page of your website.

Day 11: Some logistical points for your Side Hustle

The author believes that everything is “Figureoutable”: Side Hustlers see hurdles to be cleared whereas other people just see obstacles. They concentrate more on relevance and profitability than on the technical or the financial details…

Despite this, Chris Guillebeau offers some tips to make it easier in terms of these “logistical” issues:

  • Use a separate bank account and credit card, use cash and invoice quickly,
  • Set aside at least 25% of your extra income for taxes and fees,
  • Put any offer of service on paper,
  • Choose the simplest possible legal structure to get started,
  • Track your additional income and expenses as you go,
  • Use a dedicated workspace,
  • Transfer a certain percentage of your profits to your personal account on a fixed monthly basis.

Day 12: Decide on the cost of your product

Set a price that is low so that you attract customers but also high enough so that you can make a profit. Then it’s down to the nature of the product or service and the volume of sales you think you can generate:

  • Products sold in large quantities: you can charge a price slightly higher than the production costs and still make a good profit,
  • Lower volume products: your margin will have to be much higher,
  • Service: your hourly income needs to, as a minimum, match your normal salary and you need to include the preparation time.

What are the best books for a sideline business?

Day 13 and 14: A TO-DO List for your Hustle

Side Hustle passion

Keep your ideas as simple as possible and divide them into clear and specific steps. The clearer your idea is at the start, the more likely it is that you will put it into practice. You will be able to extend and improve your product as you progress. This is a list of things to allow for:

  • You will usually need a website. You should be able to find one for less than €5/month, which includes the domain name registration,
  • Social networks: optimise your presence on a couple of the networks and register your Hustle on other popular networks, even if you don’t use them,
  • Shared planning tools and calendars: very useful for trainers, coaches and consultants. Ex:
  • Choose a payment solution: for online payment there are various options to suit your needs, such as Paypal, Shopify, Stripe,
  • Invoices: decide how and when you wish to invoice: payment in advance, partial payment or payment on delivery. Keep it simple so that it fits in with standard practice within your sector,
  • From the start set up a maximum number of days for payments and a debt collection system for late payers,
  • For all products, have these details in your terms and conditions: what your product provides, the related cost and terms of payment.

Day 15 and 16: Define, test and improve your Hustle sales process

You are almost ready to release your product and officially launch your Hustle. Before anything else, check every step and pretend that you are the customer.

Have contingency plans for these situations:

  • What to do if users do not receive the registration confirmation email?
  • What happens if the delivery address is incorrect or if an item is lost?
  • For coaching sessions: Does your timetable accommodate different time zones?

Review your business idea one last time and see if there is anything that you can improve. A good tactic is to under-promise and then over-deliver to your customers and give them something extra or unexpected.

Consider other things that your customers would like, which you can easily provide, in order to offer them an even better product.

Ensure that you highlight the benefits and make your customers aware of how they can profit from them and make their lives easier.

And finally, put a plan into place for:

  • A regular increase in prices,
  • Some time each day to grow your Hustle: give your customer more value for their money and/or increase in your turnover.

Day 17, 18: Advertise and market your offer

Start up even if you don’t feel ready. Release in draft or Beta and continue to work on your offer, get your first customer reviews and possibly some sales.

Create a Facebook page before you make a website: once you’ve reached a certain number of subscribers, it will give you some valuable statistical information to help fine-tune your offer.

Now that your product is available, the next step is to promote it. To do this you will need a sales strategy that is attractive and not too pushy. Remember that the people who need your product just need to be made aware of it: you need to figure out a way for them to discover what it is that you have to offer.

Highlight the benefits: how will your product help people, amuse them, make their lives easier and more enjoyable? The benefits will be the results that are achieved via the use of your product or service.

The introduction letter that you send to your potential customers needs to cover what you propose to offer them and to describe the nature of your business: tell a story, illustrate it with photos or videos, emphasise how useful and valuable it will be to them.

Always consider what people really want and why they want it.

Day 19 and 20: Ask for some help to promote your product and try it out.

Contact a few reliable friends as soon as possible to get their help:

  • Suppliers who will help you promote and explain your product,
  • Mentors/experts to advise you on business and technical issues,
  • Established experts in the field to help promotion with their connections and potential customers
  • Test it with customers who can give you an objective opinion and help you to fine-tune your product with a Q & A session.

Once your product has been launched, carry out a series of tests to assess its performance:

  • Your product or service: 10% discount or free delivery?
  • How do you define your product: long or short version? Word order, calls to action, expert testimonials or happy customer feedback?
  • Your price: free trial, discounted price, no trial?

Day 21: Promotional offers

Promotional offers are one of the best methods to increase your revenue stream. There are lots of different options:

  • Discounts and flash sales,
  • Discount on the next order,
  • Loyalty schemes, referrals,
  • Free samples, trial offers, prizes, etc.

Mention limited supply and expiry dates: limited quantities, offer expires soon, etc.

Build up anticipation and announce your promotional offer in advance and run a test to check that everything is set up correctly.

Finally, when the time comes for the promotion to end, you must stick to it. Hard luck for those who miss out.

Days 22, 23 and 24: Set up the framework that seems right, develop what works and discard the rest.

Enjoy your first taste of extra cash. It’s the start of more to come and will drive you to be even more ambitious.

Next you need to assess the results:

  • It seems to work. Great, carry on,
  • It doesn’t work. Cut your losses and move on,
  • It works fairly well: you can try to modify your product in order to improve sales or increase your margins.

Develop the things that work, discard the rest. Move forward and set new goals based on the answers to these questions:

  • What works and how can you make it even better?
  • What can you automate / outsource?
  • How can you increase revenue without the need to invest a lot more time on it?
  • Can you increase the price?

Days 25, 26 and 27: Boost your sales, automate and perfect your Hustle

Side Hustle passion

Often, it’s easier to sell more to current customers than it is to find new ones. For instance, you can modify your product and present it to current customers: premium version, update, new edition…

Try to come up with additions to your product or upgrades, which can be achieved through enquiries to your customers about what else they might find useful.

Last but not least, is the step to make yourself into a true Side Hustler: automation. Document and automate your Hustle as much as you can with the use of the most appropriate products and software, if you have the money: emailing software, contact management, collaboration and project management tools, accounting software, etc.

A Hustle is different from a traditional business or a startup: ignore the experts who will tell you it’s time to move to the next level. You don’t have to expand or hire anyone. It’s your decision whether you want to grow the idea and scale it up, or whether you want to start a new project, once it is underway and fully automated!

There is no “right way” to manage your Side Hustle, just your way, which allows you to create more opportunities for yourself and gives you more freedom, as well as more additional means of extra income.

Book critique of Side Hustle”:

Side Hustle is a gold mine for the micro-entrepreneur. It’s “The $100 Startup” but a better, up-to-date, clearer and more detailed step-by-step version. This book is packed with entrepreneurial tales and success stories, just like “The $100 Startup”.

Particularly the first part, which provides a fool proof method on how to find ideas and select the best one for a quick start. This comprehensive and practical section addresses one of the main failings of the previous book. And if you lack an idea or two, Chris Guillebeau even offers you some ready-to-go ones.

Side Hustle is designed for beginners, who have never created a business, as well as more experienced entrepreneurs, who would like to establish another business as a “Side Hustle”, i.e. quickly, without risk and no need for a major financial investment. To achieve this is very easy: simply, take on the 27-day challenge and implement the suggested measures step by step.

To some experienced entrepreneurs though, the concepts and tools presented aren’t new, but this book in my opinion, is a very powerful practical guide that shows us the quickest route from the idea to the first euro. It provides the tools and the method to get things done in the right order and then allows the entrepreneur to focus on what is important: increased value for their customers and an increase in revenue for themselves.

As for myself, the book Side Hustle is a huge help for the development of my projects. I suffer from chronic ” analysis paralysis” and have a natural inclination to fragment my thoughts and projects. As I took on the 27-day challenge, I felt as if I had a coach by my side and I was able to choose an idea and to totally focus my energy to make it come true. There is no doubt that Side Hustle will accompany me every step of the way as I create my future Side Hustles!

Strong Points:

  • Written in a way that motivates you and a 27-day challenge that inspires you to take action,
  • Numerous tools, ideas, tips and real examples make it a complete practical guide,
  • A method to help you quickly select the best Side Hustle idea and fight “Analysis Paralysis” and indecision,
  • Success stories that illustrate the different concepts and that have a real educational value.

Weak Points:

  • The narrative, which is still a bit over-the-top for me, but much less so and more relevant than “The $100 Startup”.

My rating : Side Hustle passion Side Hustle passion Side Hustle passionSide Hustle passionSide Hustle passionSide Hustle passionSide Hustle passionSide Hustle passionSide Hustle passion

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