3 Steps to start a Rewarding Side Hustle

It was 7 am on a foggy Monday morning in June 2013. The sun was not up yet. I could make out the faint outline of the ferry terminal through my hotel window. A mournful foghorn split the silence announcing the arrival of a ferry. Commuters flitted like ghosts between the lights and the fog. I was thinking of my work week when a thought entered my mind. "Is this what I see myself doing for the foreseeable future? Selling more printers and services to customers? There is no challenge in it anymore. Shouldn't I be my own boss?"

I wasn't alone. A quick poll done among my corporate friends showed that this thought had entered everybody's head at some time. Typically, when approaching the 50's. At this point, your career is at its peak. You are on cruise control; your job doesn't use your total brain capacity. It's only going to be downhill from now. You feel the need to do something different and not another job. Be the master of your own destiny. If you haven't felt this need, now would be a good time to stop reading this article. 

Being your own boss has its merits, the main one being that it is more rewarding. You always wanted to experience it. The only question is, "How do I do it?"

At this point, a "Side Hustle" comes in. The traditional definition is a secondary occupation that gives you a supplementary income. I have chosen to augment this definition. 

The side hustle is something you do, alongside your day job, that is more rewarding and fulfilling. It may or may not earn you money. It is also your purpose or passion. 

You may already know what you want to do. Then go ahead and start. 

If you don't know, the thinking tools in the DYL framework will be helpful. It may entail picking up a new skill. Research has shown that learning something new is good for the brain. Better than playing chess or solving a crossword. E.g., Learning to play the piano when you have never picked up a musical instrument in your life. In my case, it was to set up a 3d printing service. 

1. Why think of a Side Hustle? 

It's a low-risk way to try out an idea. Your day job keeps the bank account topped up enough to take care of your family and lifestyle. It's like toe-dipping to test the temperature of the water before diving in. It takes up your spare brain capacity and leaves you feeling fulfilled. For me, the spark was that thought on a foggy Monday morning.

2. How do I develop a Side Hustle? 

This is the tricky bit. One of my clients knew what he was planning to do. He loved playing tennis and decided to volunteer as a tennis coach on weekends. Another one had no idea. Personally, I enjoy building things. It is energizing. The 3d printing idea was built on that passion. The thought of working on it energized me. I am one of the lucky few who knew what energized and excited me. For the unknowing majority, there is a solution.

The DYL framework has a few tools to answer the pesky questions about energy and excitement. I have used these tools to devise a 3-step process. 

Step 1: Discover the activities that energize you and how you view work. 

The ENERGY Map and the Good Time Journal. (GTJ) 

The GTJ is a journal of your activities that help you discover the energy-giving and energy-draining ones. You could record these from memory. You could also note them down before you go to bed every day. You can do this for a week or two. The choice is yours. Plot these activities on the Energy Map. I can assure you the results will be fascinating.

Understand why you work.


These views crystalize your thoughts about what work means to you. Is it for the money or the status, or you love it? This step is crucial because it affects the choice of your side hustle. If your primary motivation for working is money, then maybe your side hustle should give you additional income. If work brings you joy because you love interacting with people (other than the money, of course), then your side hustle should have people interaction. A financial reward is not a necessity.

Step 2. Brainstorm Side Hustle Ideas.

Brainstorm some ideas ONLY around your energy-giving activities.

One client, a tech industry executive, used this technique to develop a side hustle idea. Learn Chinese calligraphy to develop an art practice in the future. She wasn't in it for the money. She loved creating something.

Step 3. Pick the best Side Hustle Idea

By now, you should have a few ideas to assess. If not, please return to step 3 - the brainstorming phase. You can use the following criteria to prioritize your ideas and pick the best one.

1. Coherence 

a. Is the idea based on one of your energy-giving activities? 

b. How do you feel when you think of the idea. "Yay" or "Meh."

2. Confidence

Are you sure you can pull it off? How easy or difficult is it to try?

3. Resources

Do you have the skills, money, time to try? Or, do you need to develop new skills or make more time? 

4. I like it.

How much do you like it? Are you passionate about it? On a scale of 1-10..is it a 5 or a 9?

The best idea will be highly coherent; you will have high confidence in being able to pull it off, you have the resources, and it thrills you to the core. If you are not passionate about the idea, you need to go back to the drawing board. A Side Hustle necessarily has to be something you love doing.

When that pesky thought enters your head, it is time to sit back. Grab a coffee, silence your phone and plot your side hustle. Find out which activities give you positive energy. Discover your passion. Build your side hustle on that. 

 I started my 3d printing side hustle a few months before leaving my day job and have never regretted that decision.

Download the Life Design Guide - 3 Steps to Start a Side Hustle here.


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