How To Overcome Your Fear Of Starting A New Side Hustle

Is fear stopping you from starting a new business or side hustle? Almost every day, I receive an email that goes something like this: “I am afraid to start my side hustle and put myself out there. How do I get over this fear?” This is a common fear for anyone starting something new. Today,…

Michelle Schroeder-Gardner

Last Updated: July 10, 2024

Disclosure: This post may contain affiliate links, meaning if you decide to make a purchase via my links, I may earn a commission at no additional cost to you. See my disclosure for more info.

Is fear stopping you from starting a new business or side hustle?

Almost every day, I receive an email that goes something like this: “I am afraid to start my side hustle and put myself out there. How do I get over this fear?”Woman sitting at table reading a book

This is a common fear for anyone starting something new.

Today, I am interviewing my friend Christine on ways to overcome your fears when starting a new side hustle or business. Plus, I ask her other mindset and productivity questions I often hear.

Christine is a former full-time blogger turned certified life coach, freelance writer, and online marketer. She has tried a variety of side hustles and online businesses, and she is here today to share helpful advice to get you started with your business or side hustle. Christine is also the creator of The Harbor, a life coaching monthly membership specifically for online entrepreneurs.

Some of the questions I ask her include:

  • How can a person decide if a side hustle or business is for them?
  • How can someone get over their fears of starting a business and actually begin?
  • What’s the best planning method for productivity?
  • How can entrepreneurs create better work-life balance?
  • How can someone stop being overwhelmed when starting a new business?
  • What do you think a person should do if they are feeling burnout from their side hustle or business?

And more!

Starting a new business or side hustle can lead to many questions and fears, which can prevent people from pursuing their dreams and finding ways to make money.

With today’s article, you will learn how to overcome your fears and take the necessary steps towards starting a successful business or side hustle.

Please enjoy this interview.

Mindset and Productivity Tips For Starting A New Business

Please give us a little background on yourself and what led you to become a coach.

After college, I was stuck in jobs that paid barely above minimum wage. I didn’t have any valuable work experience or skills. And shockingly, my arts degree was not a money maker 😅.

Eventually, I started blogging on the weekends as a creative outlet from my soul-sucking full-time job. I eventually was able to replace my full-time job income (Thanks in part to your Making Sense of Affiliate Marketing course! I enrolled when you first launched it). 

I spent four years as a full-time blogger and as my blog and I each grew and evolved, I started to feel ready for a change. My blog provided a lot of step-by-step, actionable advice. I saw over and over again that my readers weren’t creating lasting change in their lives because there wasn’t a deeper mindset shift. 

This is what led me to pursue coaching. I wanted to learn how to help people use their minds to create lasting change in their lives. 

Instead of keeping my blog and transitioning it to this new niche, I decided to sell it, give myself time to immerse myself in an amazing coach certification program, and start fresh with a brand new coaching business. 

What side hustles and online businesses have you tried in the past?

I often feel like there’s not much I haven’t done! 

I tried my hand at proofreading but realized it wasn’t for me. I’ve created low-content journals for Amazon KDP (super fun!). I’ve just barely scratched the surface of selling Canva templates on Etsy.

With my blog I pursued many forms of income:

Because of my blogging experience, I’ve been able to do some amazing side hustles. 

I’ve done a good amount of freelance writing. This has been a good income source for me. However, I find it quite mentally taxing, so I can’t do a large amount of it. 

I still have a few very part-time virtual assistant clients. I enjoy the variety of virtual assistant work and getting a peek into how other people run their online businesses. Plus, the pay is good! 

I also do marketing work for a mid-sized literary company. 

Because I was a one-woman show and did everything myself as I built my successful blog, I’ve found that I have a lot of valuable skills! My successful side hustles have come because of my blogging background. 

What do your thoughts and emotions have to do with making money?

Everything! If you want to make money, learning to manage your thoughts and emotions is extremely important. Especially for side hustlers and entrepreneurs. 

Here’s how our lives basically work:

Our thoughts create our emotions. Based on our emotions, we take action (or don’t). Our actions create the results we have in our lives. In this case, the result would be making money (or not). 

Thought ➡️ Emotion ➡️ Actions ➡️ Result

When we talk about making money, we’re usually focused on our actions and results, right? But our actions are created based on our thoughts and emotions. 

So! An example: 

You want to send a series of three sales emails to your list to make money. Making money is the result that you want. 

If your thoughts are things like: I don’t want to bother people, people will think I’m pushy, or tons of people will unsubscribe, you’ll probably feel timid.

When you feel timid, what actions do you think you’ll take? You might procrastinate, send one email instead of three, and come across as apologetic instead of confident.

The result of your actions is likely going to be that you don’t make much money from your email list. 

So just to sum it up, here’s what happened:

Thought: I don’t want to bother people.


Emotion: Timid.


Actions: Procrastination, sending fewer emails than planned, apologetic vibe.


Likely Result: I don’t earn much money. 

But what if you had a different thought? Maybe you intentionally choose to think: What I’m sharing has the potential to help my readers immensely. That is going to lead to very different emotions, actions, and results. 

Thought: What I’m sharing has the potential to help my readers immensely.


Emotion: Excited.


Actions: Write emails with confidence from a place of wanting to help people, send all three planned emails because I don’t want anyone to miss this valuable information.  


Result: I follow through with my plan, serve my audience, and (probably) earn money.

Our thoughts and emotions completely change how we show up for our businesses. This massively influences the amount of money we make as well as our daily experience of being an entrepreneur. 

How can a person decide if a side hustle or business is for them?

I think that alignment is the key. There are endless ways to make money and everyone will tell you that their way is the best and for good reason–it worked for them! But it worked for them because it felt in alignment for them.

I am extremely introverted and have tried to follow methods from extroverted entrepreneurs for gaining clients. While I had a bit of success, I hated every second of it because it was so darn draining for me! 

To decide if a side hustle or business is right for you, it’s important to think about the actual day-to-day work you will be doing, not just the result you’d like of making lots of money. 

If you enjoy the daily tasks, you will be more likely to succeed. You’ll make more money AND enjoy the process. 

How can someone get over their fears of starting a business and actually begin?

I love this question because I’ve seen it come up since the day I started blogging.

I’d see new bloggers spend months trying to make their website look just right and get every single little element in place and then get super panicked about making their website public. 

Side note: Making your website live does not mean 10,000 people are instantly going to find you (if only!). Your website can be live the entire time you’re working on it. Almost no one is ever going to see it until you start really marketing it. 

So much fear comes from perfectionism. This is not about wanting everything to be perfect because we have high standards. It’s wanting things to be perfect so that we can protect ourselves from all possible criticism. 

There are two things that most experienced entrepreneurs know:

  1. Nothing will ever be “done” or “perfect”. Your business will always be growing and changing. So press publish, share it on Facebook, and tell the world about it. Striving for perfection stops you from making money and helping people. 
  2. What you do is not for everybody. Criticism can actually be a good thing. It means that what you’re doing is not bland, safe, and boring. It is memorable and will likely help you gain raving fans! 

Yes, it can feel vulnerable to start a side hustle or business. This is another reason why learning how to manage your thoughts and emotions is a powerful skill. 

If you have the desire to try something, I hope you will honor that desire and do it! Nothing is ever wasted. No matter what happens with your venture, the skills you learn along the way will be valuable and may lead to bigger and better things later on. 

What’s the best planning method for productivity?

I get this question a lot and the answer is: whatever works best for you in this phase of your life as long as you use the 4 keys I’ll share below. 

I spent years getting epic amounts of stuff done by using time blocking to schedule my weeks. However, a year and a half ago, my husband became unable to work due to chronic illness and I became his caregiver. 

Suddenly, time blocking did not work for me at all because I never knew how much assistance my husband would need each day. I needed a planning method that offered more flexibility. 

Some weeks, I use a good old-fashioned to-do list. I also have developed a planning method called the Check-Boxes Method that I use quite often. And sometimes I use a more simplified version of time-blocking. 

Any planning method can work, but it needs to incorporate these 4 keys:

  • Strategy: having an end goal for every single task on your schedule.
  • Prioritization: decluttering your schedule so that you’re doing the few things that make the most impact. 
  • Working distraction-free: everyone knows they should do this, but hardly anyone does.
  • Daily power hours: scheduling a chunk of time each day to do all the little stuff so that you free up more time for focused work. 

If you feel like you can’t find the right planning method for you, it’s probably because you’re missing one or more of these keys. The method matters much less than the execution. 

How can entrepreneurs create better work-life balance? 

The #1 most important thing to do if you want to create better work-life balance is to define what that means for you. 

The term work-life balance is really vague! It conjures up images of one of those banker’s scales where you have to have exactly the same amount of weight on each side for it to be balanced. But work-life balance is more about intentional imbalance than 50/50 balance. 

There are weeks when we spend tons of hours working and times when our personal lives take higher priority. The key is to have this happen on purpose

So what does ideal work-life balance look like for you? 

  • Is it working 35 hours per week? 
  • Is it never working at all on the weekend? 
  • Is it working 60 hours this week so that you can fully unplug for an upcoming vacation?

Work-life balance can be about where your thoughts are. 

For me, work-life balance is mostly about my mindset and being intentional. I want to be “all in” on whatever I’m doing. 

  • If I’m watching TV in the evening, I want to be all in. Single-tasking. Not also scrolling on Facebook or checking emails. 
  • When I’m working, I want to fully focus on one task at a time with as many distractions eliminated as possible. 

Here’s a journaling exercise for you: What do you imagine your life would look like if you had perfect work-life balance? Out of your answer, what can you do today (even if it’s little) to start incorporating better balance into your life? 

This exercise is worth repeating regularly. Maybe ideal balance this month looks very different than it did last month because of the life changes you have going on. 

How can someone stop being overwhelmed when starting a new business?

Learn one new skill at a time and ignore 99% of the advice out there. 

It’s sooo easy to get overwhelmed when you’re starting out. There can be a lot of new skills to learn and every piece of advice will tell you 21 more things you need to do to be successful. 

When I started out as a blogger, I focused completely on creating a regular posting rhythm. I just wrote and posted blog posts weekly. That’s it. 

Once I felt comfortable with that, I learned Pinterest marketing and incorporated that into my schedule. So I was writing blog posts and marketing them on Pinterest. That’s it. 

Each time I got comfortable with a skill, I learned something new: Creating an email list, adding affiliate links to my posts, creating digital products to sell, etc. (Not the order I would recommend doing these things in anymore, BTW.)

Whatever business you want to create, you don’t have to come out of the gate with every ideal element up and running. This is a marathon, y’all. You’ve got to be in it for the long haul.

Also, if you want to buy a course to learn a new skill, buy one course and incorporate everything you learn from that course BEFORE buying another course. One thing at a time! 

What do you think a person should do if they are feeling burnout from their side hustle or business? 

Oh man, this is such a big important topic for entrepreneurs! I’ll just dive into one aspect of it that I see most often in my clients. 

Someone experiencing burnout should work on improving the quality of their rest and downtime. Us entrepreneurs and side hustlers have a tendency to always be half-working. 

We work while we’re watching TV, check our email throughout the weekend, and respond to social media comments as we’re getting into bed. 

This means that we’re never fully “off the clock” and we have a really crappy quality of rest and downtime. 

Surprisingly, rest can be super uncomfortable! Our brains often tell us that it isn’t safe for us to rest. You might have thoughts like:

  • I should do more.
  • I could be doing…
  • I haven’t gotten enough done yet.

When you’re thinking about all of the things you could or should be doing, resting brings up underlying fear and anxiety. That’s OK! This is an opportunity to feel your emotions, allow them to be there, and then redirect your thoughts to ones that will serve you better. 

Some ideas of intentional thoughts for your downtime are:

  • It is safe for me to relax.
  • I am allowed to rest. 
  • Rest is good for me even when it doesn’t feel amazing. 

Creating more separation between work and downtime helps us recharge and recover from burnout. You need time to be fully off the clock–even if it’s just for two hours before bed. The quality sometimes matters more than the quantity. 

Side note: Your best business ideas will probably come to you when you’re fully disconnected from work. I get amazing ideas in the shower. When your mind is free to wander, it comes up with fabulously creative plans. 

What other tips do you have for someone who wants to start side hustling or start their own business?

Just do it! 😂

Honestly, my tip is to stop looking for tips and start taking messy action. Do it wrong. Do it badly. Consider every part of it an experiment and a learning process. 

You can’t research your way to success. 

Picture of Christine on a hike

What can a person learn from your coaching membership? How would this benefit someone looking to start a business or side hustle? Can you tell us about some of the people who have successfully taken this?

The Harbor is for online entrepreneurs who want to step into mindful productivity. I show my clients how to earn more while doing less by zeroing in on the tasks that will truly move the needle in their businesses and then making those happen. 

A huge part of this process is learning how to process your emotions and choose thoughts that serve you. It’s this deeper work that most people don’t want to do. But it leads to success that is anti-burnout and anti-busyness. 

If you’re just starting your business or side hustle, you will learn so many foundational skills that will help you set up a sustainable business: reducing overwhelming, creating a doable action plan, time and energy management, taking action from an empowered mindset, and more.

Some client-favorite topics that I coach on include:

  • Creating Your 1-Hour Growth Plan
  • Quality Rest and Downtime
  • Setting and Sticking to Boundaries
  • Overcoming Procrastination
  • Accountability
  • Time Management Methods

Workbooks are included in the membership so that everyone can apply the lessons to their unique situation. Plus clients can always get one-on-one help through weekly group coaching calls and unlimited written coaching. 

I work with online entrepreneurs and side hustlers just starting out as well as established entrepreneurs that are working on expanding their teams. Bloggers, virtual assistants, life coaches, writers, and more. 

I’ll share a few results directly from my clients:

“In just a few months I have gone from burnt out and overwhelmed to excited about my business and working on the things that are really going to move me forward in the direction of my goals. The Harbor has really helped me to get clearer on how to balance my business and personal life.” ~ Kayla, Virtual Assistant

“Each week I left with systems to implement that freed up more of my time. With the time that I was able to reclaim, I was able to work towards getting ideal clients. Not only was I able to get two new ideal clients, but they were booked at my highest fee pricing yet.” ~ Cassie, Pinterest Manager

“I realized during our sessions that I wasn’t working strategically, and even though I was busy, I wasn’t doing the things I needed to in order to get results… My biggest wins were getting new clients and seeing that I had everything I needed to keep making that happen.” ~ Shayna, Life Coach

“I was struggling with putting too many tasks on my weekly to-do list and feeling bad about not getting more done. Now, I have a streamlined weekly schedule that makes me focus on only the most important tasks with less guilt over what I’m not getting done.” ~ Jessica, Blogger

“I struggled with figuring out how to scale my business. I was mentally exhausted and so stressed at the end of each workday, and couldn’t see how I could take on any more work or clients. I enjoy my work far more with the new systems and am scaling my business to levels I never thought possible.” ~ Erin, Email Marketing Specialist

Most entrepreneurs and side hustlers think that they need to learn a new strategy to earn more money. What they actually need is to learn skills like mindful productivity, how to overcome procrastination and overwhelm, and how to do fewer, high-impact tasks. 

I often tell people that you don’t need to learn a new strategy. You know enough. You need to fully apply and incorporate what you already know. That’s what The Harbor is all about. 

You can learn more about The Harbor by clicking here.

What’s holding you back? What questions do you have for Christine?

Filed under:

Michelle Schroeder-Gardner

Author: Michelle Schroeder-Gardner

Hey! I’m Michelle Schroeder-Gardner and I am the founder of Making Sense of Cents. I’m passionate about all things personal finance, side hustles, making extra money, and online businesses. I have been featured in major publications such as Forbes, CNBC, Time, and Business Insider. Learn more here.

Like this article?

Join the Conversation

Leave a Reply

Your email address will not be published. Required fields are marked *

  1. Sasha

    Hey Michelle, just wanted to first say thank you for writing a post about this topic. It’s always been a struggle for me to come out of my comfort zone and do something for myself that could potentially help me financially. I’ve thought about doing side hustles with my mom like making things and selling them on Etsy, but I always doubt myself thinking nobody would ever purchase it! This was very inspiring, hopefully this is the push I needed to get me started on making extra money!

  2. I’m so glad you were inspired by my interview Sasha! I have had those exact same doubts, so I know that you can do this!

  3. Side hustles online are today’s new new for changing the way you think and earning healthy streams of passive income that NEVER LOSE WEIGHT, as long as you do the transformation business work out of inspiration or desperation! ๐Ÿ™‚