How to Side Hustle for Freedom & Fun (And Launch New Ideas)

“Do we not pay you enough?”

I still remember the mild horror in the voice of my kind boss years ago when he asked me this after finding out that I was tutoring in the evenings to make a few extra bucks for my wedding. I was serving as the (very) full-time program director of a fast-growing youth development organization. Years later, I also remember the puzzled look on my husband’s face when I began rummaging through my closet to sell clothes on eBay while home for my first maternity leave. The term, “side hustle” did not really exist then. 

I have noticed over the last couple of years that many of my coaching clients have been experimenting with a money-making side project or two in search of security and sense of fulfillment that can come from additional income and using their many talents. 

So when I saw that Gretchen Rubin, the author of Four Tendencies, recommended Chris Guillebeau's book, Side Hustle: From Idea to Income in 27 Days, I read it right away. It is an approachable book without any gimmicks. It offers thoughtfulness, simple planning and a take-charge, positive spirit. I have been telling everyone about it, including folks happily settled into a full-time job, and here is why.

Even though I do not believe in filling up all our free time with something “productive,” I love Guillebeau’s philosophy of side hustling as a way of giving oneself more freedom. Whether the goal is to pay off credit card debt, build savings or make a career transition, side hustling gives an additional sense of financial security. Side hustling lets you keep your main source of income while pursuing different interests. It is a great way to infuse more fun and color into your life without quitting your day job or committing yourself to a dramatic change.

Guillebeau’s thoughts reminded me of what Susan Cain, author of Quiet: The Power of Introverts in A World That Can’t Stop Talking and Soman Chainani, author of the popular young adult series, The School For Good And Evil, said about their side hustles. Susan Cain taught negotiation skills on the side as she wrote her first book, while Soman Chainani tutored and helped high school students prepare their college applications. In fact, Chainani still does this side gig! These side hustles allowed them both to feel secure and not rush their creative work. Cain put it this way: “If art is your only source of income, it drains your creative energy. This way, your creative soul feels lighter.” You can listen to them talk about this in the “Lessons and Warnings From Successful Risk Takers” episode of The Tim Ferris Show. 

These are some other takeaways that resonated with me:

1. Brainstorm and borrow as many ideas as you can by paying attention to your current talents and interests, and what is happening around you.
2. Then use the “Tinder for Side Hustle” approach to pick one or more ideas that work for you right now, and save the other good ideas for later. Like swiping left and right to pick potential dates, select the ideas that work based on the criteria of feasibility, marketability and profitability. And fun! Be honest and disciplined about the amount of time and money you want to – and are able to - devote to the side hustle. 
3. Launch your idea before you feel it is ready. Continue to work on improving the side hustle and try to elevate the ideas that do work to the next level of quality, efficiency and profitability.
4. Side hustle without income is just a hobby. Get paid.
5. Monitor and evaluate success based on few simple metrics. At any point, you should be able to assess your progress and answer the question, “How is it going?” with a thumbs up or thumbs down.

If you do not want to buy the book, listen to Guillebeau’s free podcast, Side Hustle School. Each daily episode features a short case study of a side hustle and takeaway lessons.

Here are a few fun episodes to try. Each one is under 10 minutes long. 

1. Electrical Engineer Becomes Romance Novel Cover Model
2. Government Employee Becomes Flash Mob Marriage Proposal Consultant 
3. Golfer Takes a Swing and Scores $5,000/Month Hustle 
4. Freelance Writer Starts School To Help Writers Start Side Hustles  

I really appreciate how these short podcast episodes are designed to spark and generate business ideas for the listeners, but the book wonderfully synthesizes the lessons from the podcast and provides a cohesive framework for getting a side hustle started. I think it could be a great model to help you get any ideas off the ground, including new programs or products within already existing organizations or businesses. I am not looking to start my own side hustle anytime soon, but I will be using the concepts to support my aspiring side hustler clients, and to implement new ideas for my coaching and consulting practice.  

Have you tried a side hustle? What have you gained from the experience? What didn't work for you?