The art of the Side Hustle by Jonathan Lai

BY Tremis Skeete ON JUNE 4, 2018

A full-time job pays the bills. You work with a team of people, customers, and clients, and you do it because you have to, and not necessarily because you want to. A side hustle on the other hand, is a job you do before or after your regular job.

Product manager Jonathan Lai understands the distinction between his full-time job and his side hustle. When it comes to side hustles, he says, you most likely are not making any money at it, and you’re doing it alone. Your main hustle focuses on daily life consumption, your side hustle allows you to be more creative.

The Power of a Side Hustle

Jonathan has noticed that a side hustle can make your main hustle better, which then in turn makes your side hustle better.

Jonathan works for Compass, a fast-growing real-estate technology startup, and he creates products for Compass agents to guide their buyers and sellers. Jonathan’s side hustle is Tribe of Five, a business aimed at helping people to achieve their goals. When someone signs up to meet a goal with Tribe of Five, they are paired up with four other people who are working towards the same goal. Then, the five of you are presented with a 30-day challenge. Each day you complete a small task related to your main goal, and you can hold the rest of your group accountable for following through.

Jonathan discusses three benefits of a side hustle that stick out to him.

  1. It helps you connect the dots. A side hustle can help to renew those basics that are keys to success.
  2. It inspires you. Product managers are always looking for inspiration, and side hustles will widen that lens.
  3. It helps you meet new people. Side hustles will give you a reason to have deeper conversations.

Start a Side Hustle

You can either work on it alone, or form a group.

Working alone gives you a lot of freedom. It requires daily action, even as little as five or 10 minutes a day, and commitment. If you work on your side hustle every day for at least 30 days, it will become a habit. However, many people will fail because of the unknown that comes with working alone.

Jonathan believes the better strategy is to work with others. Working alongside others generates greater inspiration, collaboration and accountability.

Tremis Skeete


Tremis Skeete

Tremis is Director of Product at NexTier Innovations, a management consultancy specializing in Multi-Dimensional Analytics and Project Portfolio Intelligence. He helps product leaders and teams shape design strategies and prototypes to build quality software. Tremis is also Senior Product Analyst at Paralect, a product engineering organization devoted to working with clients all over the world to create, launch and support complex custom software.