Did you know that a 2014 study from Deloitte revealed that 70% of millenials want to start a business instead of working in a traditional environment?

With more folks including notable entrepreneurs such bestselling author and Publisher of Success Magazine Darren Hardy speaking up in favor of launching while working, side hustling is a growing movement in the entrepreneur playing field and viable way to generate extra income or start a flourishing business.

But just because you have the security and cash flow of a day job doesn’t mean that your journey to grow a business will be an easy climb. Having a strong desire is important but it takes more gusto to make sh*t happen in your hustle. So whether your goal is to leap from the ladder or permanently create a sustainable income stream here are some tried and true ways to make it happen.


1. Stop trying to do too much

In a recent #sidehustlechat focused on the importance of scheduling practices, many of our participants admitted that overcommitting or underestimating the amount of time to complete a task was their achilles heel.

No matter how motivated and inspired you feel, a to-do list with 20 things on it is never a good idea.

TIP: Don’t forget that when you work full-time, a big portion of your time is already accounted for. Keep track of what’s on your plate by scheduling when you will complete tasks and include a realistic time estimate.

To help you figure out the estimates for your projects, think of tasks that you do regularly and use a time tracking app such as toggl to determine how long it takes you to complete it from start to finish. Before committing to projects, review what you already have on your plate and identify if your to-do list can handle another line item. Aim to create a schedule that sets you up for success instead of stress and disappointment.

2. Start making healthy habits a priority

Side Hustling isn’t easy but don’t buy into the myth that you have to push yourself to exhaustion to be successful.

Taking breaks doesn’t make you less dedicated, it makes you more productive by allowing you to re-charge and stay focused. Everything that you want to make happen needs one important thing to be possible: YOU

You can’t make anything happen if you’re too tired, too stressed or too burned out to do the work.


TIP: Start treating self-care as a non-negotiable priority. Contrary to popular belief, self-care isn’t just about spa days or elaborate getaways. It can be as simple as creating a morning and nightly routine, disconnecting from your digital devices for an hour a day or finding 20 minutes of time read a great book.

Find a practice that helps you feel refreshed and is manageable enough that you can commit to doing it daily.

3. Stop Procrastinating

Although there are times when procrastination can work in your favor, if your strategy to get things done includes waiting for a deadline to push you forward or for everything to be perfect, your hustle is in trouble…

TIP: Procrastination is rarely a sign that you’re lazy and more of an indicator that something deeper may be the cause. Although the reasons for procrastination vary the result of repeatedly doing it is always the same – a burdensome cycle of stress, anxiety and feelings of shame.

Get the bottom of your avoidance and take action to put it to an end. If tasks have you feeling overwhelmed, break your day down into manageable chunks or start your day with easier ‘quick wins’ to help you build momentum to finish the rest of your day. If you need an extra push or advisor to keep you on track, enlist the help of an accountability partner.

4. Start using envy as motivation

Confession: When you’re a side hustler with a desire to work for yourself full-time, sometimes  a little FOMO (Fear of Missing Out) or envy will creep up when you see folks doing what you aspire to do in business.

Comparison can be an icky feeling but only if you choose to focus on what you lack instead of recognizing the subtle lessons that you can use to improve your own hustle.

TIP: Don’t let comparison stop you in your tracks. Transform those feelings of envy to motivation and action by:

  • Identifying what you envy about this person (No shame in speaking your truth)
  • Identify the underlying qualities that this person has which contributes to their success
  • State 1-2 things that you can start doing to embody (NOT COPY) this trait in your work ethic.

Remember that the fact that someone is doing it now, means that what you desire IS POSSIBLE and should serve as a sign to keep going.

Need more convincing that envy can be a good thing? PR Pro and blogger Kayla Hollatz has a great post about this by sharing how to deal with blog jealously and 99u shares how you can use the success of others as a mirror for your own journey.

Challenge for you: Think of your favourite side hustler, full-time entrepreneur or someone killing it in your niche and use the questions above to help you. For some extra motivation, I’ll share the responses to this exercise for my side hustle crush Rosetta Thurman of Happy Black Woman.

What do I envy: Her ability to work full-time in a job she created and travel across the US to teach her programs.

What qualities or traits does this person have to be successful:

  • Consistency – Through her regular blog and social media engagement
  • Community focused – By hosting regular webinars and teleconferences which solve specific problems that her audience may be experiencing
  • Helpful – By creating several how-to posts and and events that inspire her audience to take action

How will this inspire me?

  • Create more content that solves specific problems
  • Don’t be afraid to reach my audience through different mediums such as webinars
  • Stay the course and remember that what I aspire to do is possible because someone else has done it.

5. Stop being afraid to fail or change direction

Don’t let the safety net of a job be the bubble that prevents you from taking risks. One of the biggest benefits of having a day job is that you have the security of your paycheque. Use your time as an employee to test the waters and identify if you have a viable business idea and most of all, if you even like it!

Did you know that Biz Strategist Amber McCue had a boudoir photography side hustle before starting her successful business strategy consulting firm Nice Ops? Side hustling brought her entrepreneurial spark to life but also helped her realize that her love of photographer wasn’t meant to be a full-time gig.

My friend Gwen Elliot juggles multiple hustles as a mediapreneur, TV producer and Money Maven and up until recently was a Start Strategist until she realized that her true calling was helping entrepreneurs learn the ins and outs of getting media coverage. She knows her stuff and you can check her out here.

Lastly, my first side hustle was fitness modeling, freelance writing and personal training. (I even have the bikini clad website to prove it) But I’ve evolved through the years to become known as Mental Health and Wellness Advocate, Speaker, Consultant and Business Strategist (with a passion for working with my fellow side hustlers).


TIP: Don’t be afraid to pivot or change your mind. It doesn’t matter if you launch something to crickets or if the original idea you thought you’d love actually bores you to tears now. It’s ok to start over, try something new and embrace that you may not always know what lies ahead.

Over to You:

What rules do you live by to make sh*t happen in your side hustle? Share your secrets below in the comments!


Founder + CEO at Secrets of a Side Hustler
Chivon John wants to live in a world where individuals feel empowered to create their own opportunities instead of waiting for them. In 2014 she founded the Secrets of a Side Hustler community to inspire, educate and connect individuals who have or want to start a business in addition to their full time employment. You can connect with her at @chivonjohn