Quit Your Day Job (but Start a Side Hustle, First)

If you hate your job, quit. But before you do, get your side hustle going. Here’s How.

Written by Zach Servideo
Published on Dec. 15, 2021
Quit Your Day Job (but Start a Side Hustle, First)
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If you follow economic news, you likely know there’s a labor shortage in America in addition to The Great Resignation. The reasons are numerous and complex, but personally I see one reason among my peers: People are tired of spending their time on unfulfilling jobs that make other people rich.

My advice? If you hate your job, quit. But before you do, get your side hustle going. 

4 Steps to Launching Your Side Hustle

  1. Figure out what you’re passionate about and pick your side hustle accordingly.
  2. Dedicate five to seven hours a week to your side hustle, but no more.
  3. Decide what to charge. We don’t work for free!
  4. Put in your two weeks’ notice ... strategically.


Pick a Side Hustle

If you know you want to get out of your current job, but don’t know where to begin, start with your favorite interest or hobby. What are you passionate about? Do you see others making a living in the field? What types of projects have you worked on before that you enjoyed?

For me, my passion is advising startups, in particular early stage (pre-series A) companies and first-time entrepreneurs. In the back half of the 2010s, I moved away from advising startups. Businesses I worked with were acquired and I suddenly found myself advising massive companies like WarnerMedia, ViacomCBS and Vizio. Even the startups I worked with ballooned from six … to 50 … to 200 employees. I lost my ability to impact multiple areas of the business like I did when advising seed stage and series A startups. 

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I rectified the problem by immersing myself in the Boston startup ecosystem. I launched a podcast, Boston Speaks Up, where I interview inspiring figures in the innovation economy. I developed a relationship with Endicott College where I’m now the Entrepreneur-in-Residence at the business school’s Angle Center for Entrepreneurship. Before I knew it, I began meeting tons of first-time founders who needed my help. It was only a matter of time before I made the leap to become a founder myself and started Value Creation Labs (VCL). 

That’s what worked for me, but there are all sorts of ways you can start your side hustle. Seek out groups, business and people in the community you can connect with — digitally or in-person — to start to learn how to turn your passion into a full-time role. Go to the businesses you admire; see what they're doing well and what they’re not. Talk with friends about your strengths. What skills do you need to improve to be considered a professional? 

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Dedicate Time to Your Side Hustle

I tell people to spend five to seven hours a week on developing their side hustle. It might not sound like much, but you don’t need to run head-first into something right away. Life is for the living and if you still have a full-time job, you’ve got a lot going on already. I’m not one of those rise-and-grind people who will tell you to work 80 hours a week. That’s nonsense.  

Don’t get discouraged. Slow and steady wins the race. Your dream of turning a side hustle into a full-time gig could take a year (or more) to realize.

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Decide How Much to Charge 

I’ve seen a lot of advice telling people to work for free or at a significantly reduced rate when starting a side hustle. Don’t do that. Repeat after me: We don’t work for free.

Unless you’re completely new to a field in every regard, then you probably have a good deal of experience in at least some of the areas you’re looking to pursue as you launch a new career.

Don’t make any risky entrepreneurial bets with your career unless you have $50,000 liquid in your bank account.

If you’re working with a startup, accepting ownership or equity can be a smart way to transition as an advisor. If you go this route, don’t hide your intentions; do it above board and get things in writing. Otherwise, don't be afraid to set a rate that you're worth.


Put in Your Two Weeks

In my experience, once people are paying you on the side for a few months in steady work, it’s time to start thinking seriously about making the switch. Soon people will want to pay you more, but you won’t have the time in your current job. 

I’m not one of those rise-and-grind people who will tell you to work 80 hours a week. That’s nonsense.  

If you have specialized skills, like design or development, you can monetize a number of projects on a fractional basis through a consortium or agency that works with contractors. This can be a great way to grow your background before making the leap into a new career. I have a number of professionals with full-time gigs who are spending no more than five to seven hours a week providing low-touch, high-impact work for VCL clients on a consulting basis. 

You can also leverage this type of side development in your current role. If your job can't offer you more money or better work, you should develop a timeline that makes financial sense to leave.

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Knowing when to leave varies from person to person and I’m no financial advisor, but one of my mentors gave me advice early on: Don’t make any risky entrepreneurial bets with your career unless you have $50,000 liquid in your bank account. Following this advice has served me well. 

I’ve worked on both sides of the side hustle game — starting companies and managing contractors, but also working on my own projects that have developed into new businesses. There’s no one-size-fits-all approach but hopefully these tips will help you build your own road toward working in a more fulfilling role. 

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