I know you have a dream.

Whether you started your side hustle to make some extra cash or eventually leave your 9-5, I’m willing to bet that you have a strong desire that motivates you to hustle everyday.

However, the more I connect with fellow side hustlers and wantapreneurs who want to start the side hustle life,  there is always a common thread that gets the most of us sometimes – Doubt

No matter how strong your focus is or the time management hacks you master, there will be days when self-doubt and fear can get the best of us. This fact was definitely very clear for me after reading the results of a survey I recently launched for our community which asked folks to share some of their greatest challenges as a side hustler. Even though the results are still coming in so far mastering your mindset is emerging as a clear leader.

Trust me I get it. Side hustle life isn’t easy.

On most days it’s easy to find your flow and balance and on others it can feel overwhelming and confusing.

First, realize that no one is immune to negative self-talk. Even seasoned entrepreneurs still experience moments of fear, doubt or even depression.

But, if you find yourself being excessively critical, it’s time to start challenging your inner critic.


The secret to being successful as a side hustler won’t be found in trying to do more each day. Rather, you’ll experience your biggest wins by having badass mindset that serves as your biggest cheerleader through your journey.

No matter if you’re just starting out or if you’re a veteran side hustler ready to take your biz to the next level, here are 4 mindset makeovers needed to make as a side hustler:

Mindset Shift #1: You are a real entrepreneur.

Just because you’re working on your biz part-time doesn’t minimize your journey. Imagine if MailChimp and Freshbooks, two businesses that were jumpstarted as side hustles didn’t believe that they were ‘legit’ as they were building their operations from the ground up?

Side hustling is emerging as a growing trend in entrepreneurship and a recent study by the Academy of Management Journal revealed that side hustles are one third less likely to fail compared to businesses that are begun as full-time enterprises. So take comfort in knowing that you’re working at your own pace and creating something that has a great chance of succeeding.

RESOURCE: Need an extra boost to kick your impostor complex to the curb? Check out the amazing interview we did with Tanya Geisler


Mindset Shift #2: Stop telling yourself you need No Days Off and No sleep

Contrary to what rap songs, memes or your own inner voice says: hustlers do need to sleep. I recently hosted an event cheekily titled ‘Hustlers Don’t Sleep? to raise awareness of the importance of making wellness a priority in your business.

Whether you hold down 50 hour weeks or you’re chasing the mythical 4 hour one, prioritize the creation of routines and practices that will help you perform at your best. It’s one thing to not sleep on opportunities and remain focused on meeting your goals and a completely different scenario of working your body to point of exhaustion.

Here’s this for some extra food for thought: If you find yourself in constant hustle mode, yet nothing ever gets done, it might be is an indicator to stop and re-evaluate.

From one recovering overachiever to the next I totally understand. Sometimes you want to keep pushing when yourself, but remember, you have permission to rest. Get in the habit of blocking off time for yourself on your calendar and regularly check in to ensure that working on your business doesn’t feel like you’re hustling backwards.

Mindset Shift #3: You don’t need to be everywhere online

Is social media important in business? Absolutely but don’t fall into the trap of thinking that you have to be everywhere and connected to every new platform that pops up.

As much as social media breaks down the barriers of connection there are times when it can feel a little stressful as you try to keep up or even make you feel like you’re not measuring up to the perfect curated profiles of others.

Even if you’re craving connection, is participating in 20 Facebook groups, trying to take perfect photos for instagram, tweeting and snapchatting everyday really helping you feel more engaged and make more money? Sure you’ll be visible but doing more of something doesn’t necessarily mean you’re in a better position.

Reframe your approach to focusing on creating quality content, making genuine connections and remembering that your life cannot be reduced to a single status update. Behind every perfect instagram feed is a person who is also just trying to figure things out so don’t spend your time comparing yourself to their journey or photoshop edited pics.

If you find yourself getting a twinge of envy as you scroll through someone’s feed, don’t beat yourself up because it may be a sign that you need to take a timeout or mini social media break.

Remember that you don’t have to be everywhere and it’s possible to start and grow your biz without spreading yourself everywhere online.

RESOURCE: Need some more convincing? Here’s a great post from Content Strategist Jules Taggart on ‘Why we hang on to marketing strategies too long’. She shares her story of why she ditched her business Facebook page and how to figure out how to ditch the tools that don’t add value for you.

Mindset Shift #4: You define your timeline and goal

As sexy as the “fire your boss” narrative sounds, the end goal of side-hustling is not always full time entrepreneurship and that’s ok. Whether your goal is to transform your side hustle into your full time gig or just explore an untapped passion don’t get caught up on what you think you should be doing.

There is a lot of chatter online and stories of folks who have built six figure businesses or leapt from their jobs in a matter of months.

Kudos to them but focus on yourself.

Remember, you can’t hit a target that you cannot see so clearly identify what your goals are as a side hustler.

Do you want to pay off debt? Leave your day job or just keep it as an occasional side project? The answer to these questions will help you figure out how much or little you need to hustle to meet your goals. Behind every success story is a journey that we often don’t see.

Focus on watering your own grass and remember the best blueprint of entrepreneurship is the one that you have a hand in creating.

Over to You

What mindset shifts resonated with you the most and what would you add to this list? Share your thoughts in the comments!

P.S. There is still time to share your thoughts in our Side Hustler Community Survey! If you have 2 minutes we’d love to hear your feedback on what you need support with and how we can support you. You can access it << here >>


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