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



  1. Everyone should have a side hustle (income diversity gives you more options)
  2. It's not hard to start a side hustle
  3. To be successful, you need to be able to generate profitable ideas and pick the best one
  4. Side hustles are all about action!

What you need:

  • The right frame of mind
  • The willingness to act

What you don't need:

  • A lot of money
  • A lot of time
  • A business degree or other specialized education
  • Employees
  • Experience starting a business

Week 1: Get Ideas

Day 1: Predict the Future

What is the goal that drives your desire for a side hustle?

Day 2: Learn how money grows on trees

Your idea must:

  • Be Feasible
  • Be Profitable
  • Be Persuasive

Day 3: Brainstorm, borrow, or steal ideas

Brainstorm ideas from these basic categories:

  • Sell a product
  • Offer a service
  • Be a middleman

Starter ideas: finite and not scalable (sell your stuff: eventually you'll run out of stuff to sell)
Next Level Ideas (NLI): scalable (buy other people's stuff and sell for profit)

Day 4: Weight the obstacles and opportunities of each idea

Identify constraints and oppurtunities

Day Forecast your profit on the back of a napkin

Use a simple forecast: Profit = Revenue - Expenses

Sensitivity: choose a best, worst, and expected case

Week 2: Select Your Best Idea

Day 6: Use the side hustle selector to compare ideas

Rank your ideas on these qualities:

  • Feasibility
  • Profitability
  • Persuasiion
  • Efficiency (how quickly can it be executed)
  • Motivation (how excited are you?)

Day 7: Become a detective

Look at what other people are doing and do it better or differently

Day 8: Have imaginary coffee with your ideal customer

Create a specific avatar of your imaginary ideal customer and think about how you serve them

Day 9: Transform your idea into an offer

An offer has a promise (benefit they will receive), a pitch (everything they need to know and nothing more), and a price (and call to action)

Day 10: Create your origins story

Don't just give facts, tell them a story. "I've always been frustrated with and I knew there was a better say. I made." or "I've always been interested in so I decided to try ".

Week 3: Prepare for Launch

Day 11: Assemble the nuts and bolts

Resourcefulness is your most valuable skill as a side hustler.

  1. Get a separate bank account for your side hustle
  2. Get a separate credit card for expenses for your side hustle
  3. Pay for everything up front
  4. Set aside 25% of your income for taxes
  5. Be fast with invoicing: get paid quickly
  6. Insist on written agreement for service work
  7. Legal structure: go to LegalZoom...
  8. Set up a simple accounting system. Look for cheap or free, you just need to track income and expenses
  9. Set up a separate hustle workspace
  10. Pay yourself first

Day 12: Decide how to price your offer

  1. Design with recurring revenue if possible
  2. Consider pricing tiers
  3. Don't stray from market prices

Day 13: Create a side hustle shopping list

  1. What will people expereince after purchasing your product?
  2. What needs to happen for your to deliver that experience to them?

Day 14: Set up a way to get paid

PayPal, Shopify, Stripe, etc.

Day 15: Design your first workflow

Create the processes needed to make your idea work:

  1. How will prospective customers learn about your idea?
  2. What will happen after someone purchases your product?
  3. What else needs to happen in order for your customer to pay for and recieve your product?

Day 16: Spend 10 percent more time on the most important tasks

Only focus on two things:

  1. Change your customer's life
  2. Make more money

Week 4: Launch

Day 17: Publish your offer

  • Create a Facebook page before a website
  • Launch in Beta first

Day 18: Sell like a Girl Scout

Remember, the people who need your product want to hear from you

Day 19: Ask ten people for help

Ask your contacts for a single actionable thing they can do to help

Day 20: Test, test, and test again

You don't know what will be most effective so try different things and record the results (basic A/B testing)

Day 21: Burn down the furniture store

Use promotions to help! Use the psychology of scarcity and urgency to your advantage.

  1. Announce in advance
  2. Don't make them jump through a bunch of hoops
  3. You must provide substantial perceived savings
  4. Provide an offer they can get excited about
  5. Test your systems to make sure they work
  6. When it ends, it ends

Day 22: Frame your first dollar

Celebrate your accomplishments

Week 5: Regroup and Refine

Day 23: Track your progress and decide on next steps

Track what matters and ignore what doesn't. What matters:

  • Profit
  • Growth
  • Time (your time spent on the project)

Day 24: Grow what works, let go of what doesn't

Audit your side hustle occasionally:

  • What working and how can I develop that further?
  • What could I automate or outsource
  • What could I do to make more money without spending more time?
  • Could I increase prices?

Day 25: Look for money lying under a rock

An easy way to grow is horizontal expansion

Day 26: Get is out of your head

Systemetize where you can, write down workflows and processes

Day 27: Back to the future