Is Your Millennial’s Side Hustle a Red Flag?

Source: Bankrate’s Side Hustle Survey, June 22-25, 2017

Millennial side hustle is more than a sexy new name for earning extra cash.

As a professional keynote speaker, I often grab a Lyft or Uber from the airport/hotel. My recent driver was a Millennial college graduate who worked at a medical credentialing agency as a “day job”. When I asked why he was driving his response was, “It’s something different… I enjoy it…and it’s flexible money. I can do it whenever I feel like it.” He wasn’t driving just for extra cash – the side hustle provided things his “pay the rent” job didn’t.

The side hustle is a key indicator of how the workforce is being disrupted. Intellectual stimulation or giving their life more meaning are top reasons for Millennial side hustles (ok, the extra cash doesn’t hurt either).

Driving is just one of the side hustles, but there are four core Millennial red flags that leaders must pay attention to:

    1. Flexibility. I want to work, when I want to work. This is moving from a Millennial hope to a Millennial demand. They want the ability to control their schedule and fit their work around their life, NOT their life around their work. Flexible work schedules, working from home (or the coffee shop), and added PTO (personal time off) are becoming more common practice.

      Red Flag Reflection – What flexible scheduling options do you provide?

    2. Freedom. The side hustler is looking to keep their options open. When they are not fulfilled by their current job a side hustle gives them the freedom to explore and try new options with minimal risk. They can even learn new skills that may build into a new career path. They can put up a profile on Upworks and get clients with no overhead and build an instant portfolio.Red Flag Reflection – How do you discover and develop employees’ untapped talents and passions?
    3.  Strategy. The side hustle is an access point to what they really want. While working their “day job” the Millennial will use the side hustle as a bridge to something bigger and better. Their goals may be making contacts, networking, or training. One of my drivers shared that he used his side hustle drive time to meet executives on the way to the airport. He had closed 6 figures in deals from those relationships.Red Flag Reflection – What systems do you have to help Millennial talent strategically leverage their growth?
    4. Self-Expression. Their “day job” does not feed their spirit or advance their purpose or their cause. Millennials want to be part of a CAUSE that is worth giving their full BEING. They need to know that their (BE)CAUSE™ can be fulfilled with you. A side hustle may not be a paid gig. It may be a volunteer position that enables them to find meaning. Their passion for self-expression shows up everywhere, even in their dress code as I discuss briefly in this recent article from the Seattle Times.Red Flag Reflection – Do you know each team member’s (BE)CAUSE?


If leaders don’t learn to leverage the Millennial side hustle, they will be left behind. Here are 3 tips on how to begin…

Provide Career GPS

Millennials are looking for a roadmap to success and expect their employers to provide it. To keep your Millennial engaged at work, have frequent explicit conversations about their progress on the job plus their opportunities for advancement.

Don’t Confuse the Side Hustle with Disloyalty

As long as the side hustle doesn’t violate a non-compete clause or involve a competitor, it can affect your bottom line in a positive way. Variety and self-fulfillment can help your Millennial be more well-rounded, energized, and even extend the time they stay with you.

Don’t Ignore the Side Hustle – Embrace It

Create a space where it’s safe to talk about their side hustles. Be positive and curious about WHAT they get out of their side hustle and WHY they do it.

The WHAT and the WHY they side hustle is priceless information.

Leaders that are in an open dialogue with their Millennial talent will find they stay engaged, happy and don’t leave you wondering “why did they leave”?

About Anna Liotta
Founder of The Generational Institute and author of the best-selling book Unlocking Generational Codes, Anna Liotta began studying generations first as the youngest of 19 children and later as a college faculty member, keynote speaker and generational consultant. Based in Seattle, Anna is an expert in helping organizations create a generational savvy culture. Contact us to book Anna to speak at your event.

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