Fear and Freelance: How to Be Confident & Brave In Your Business: 24 tips!

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Abbey Ashley

Overcome the fear of starting your own business.

“How do I get over the fear of starting my own business?”

“What if I fail?”

“What if no one hires me?”

Are any of these hitting home for you?

Listen…I. Get. You.

There have been times in my own business where I was plain SCARED. I had to stare my fears in the face and decide I was not going to let them stop me.

I want the same for you, and that’s why I’m sharing 24 ways you can overcome fear right now, and experience more confidence and boldness in your VA business.

Your Mindset Matters

Before I share my hacks with you (and these really do help), I want to start out by saying that your mindset DOES matter. 

How you think about yourself and your business is going to impact the decisions you make and how others view you. 

I’m not trying to freak you out here—my whole point is to show you how making a few adjustments in your mindset can actually have a positive impact on your business. 

So here it is…these are my top hacks for overcoming fear and insecurity!

Learn more about overcoming the fear of failure in your business here.

1. Journal Your Fears…Then Debunk Them

This is one of my favorite ways to overcome fear, so I HAD to put it first. If you’re on my email list, you may have heard me talk about it already. 

One of the things I LOVE to do when I’m struggling with fear is to write out my fears on a piece of paper, and then on the other side of the paper write a truth that COUNTERS the fear. 

Sometimes all it takes is a cold hard look at the TRUTH to realize that our fears were not as real as we thought.

2. Remember Your Accomplishments (Make A List If Needed)

If you’re feeling a little down on yourself, it may be time to remember all the things you’ve accomplished in your business. Hey, maybe you just started and you feel like you don’t have much to celebrate–but that’s not true. 

The fact that you are even reading this blog post shows that you’re taking ACTION.

So any little thing you’ve accomplished–from simply finishing your brand logo to announcing your business–CELEBRATE IT! Every step you take is an accomplishment. 

3. Ask A Friend

Your friends can be your biggest cheerleaders. Just when you think you “can’t do this” or you’re “afraid to fail” your friend will come in and remind you that it’s NOT  true! 

They know you (and sometimes better than you know yourself, right?), so they recognize your strengths and probably can see a little bit more clearly than you can. They’ll keep you in check if you’re getting in your head too much. 

4. Find A Community

A great way to become confident in your business is to have a supportive community to back you up! Find like-minded people in your niche who can help encourage and support you through your business journey. 

You can do this by looking for Facebook groups or attending networking events. 

A great place to start is my free VA Savvies Community. With over 70K professionals, you’re bound to find some good people to connect with and hold you accountable.

5. Remember Where You Started

One of the things that can get you really low in spirit is thinking about how far you have to go, or the goals you haven’t reached yet. I can’t say how important it is that you take time to actually remember where you started from! Even if you just started yesterday…each day and each step you take is PROGRESS. 

Maybe within the last couple of weeks, you learned a new skill or you made a new connection. Maybe you took a course or read a book that helped you grow your knowledge on a particular topic. Any steps you’ve taken have already put you ahead of where you used to be!

6. Don’t Compare Yourself

I’ll be honest with you, the quickest way to shatter your confidence is to start comparing yourself to other people.


I know it’s tempting. I know all the online experts might make you feel like you know absolutely ZERO…but it’s just not true.

And honestly, everyone is at a different point in their business journey. We all started at level 1 (no one is born a successful entrepreneur, right?)

So breathe easy, enjoy the journey, and put your blinders on! Focus on YOUR path!

7. Improve Your Skills

Taking time to develop your skills can be a HUGE confidence booster. When you KNOW you’re good at what you do, how can you not be confident, right?

If you feel like you’ve been struggling to be bold in your business, sharpening those skills can help you step out boldly and feel sure of yourself. 

8. Don’t Go By Your Feelings

Here’s the truth, you might not “feel” bold…but that doesn’t mean you won’t be successful.

Can I tell you how many times I did something in spite of my “feelings,” and actually got a good result? Your feelings will change from one day to another, so don’t let them be the driving force in your business!

9. Do Something “Scary” 

Doing something outside of your comfort zone can boost your confidence a lot more than you might think.

See, there’s probably a list of things you just don’t do because you think you can’t. But what would happen if you started actually doing what you thought you couldn’t…and succeeded? 

You’d probably feel a little better about yourself! Now, I’m not talking about doing something life-threatening or something that can be a huge risk for you financially…

I’m talking about BASIC things that you could be doing in your business but you don’t because of fear.

Maybe that means reaching out to a potential business owner and cold pitching your services. Or introducing yourself to someone in your industry you look up to. Or…just TELLING your friends and family that you’ve started a business. 

(Do me a favor…I want you to TRY THIS, and then post about it here in this group)

10. Find Hobbies OUTSIDE Of Work

As a business owner, I think it’s REALLY important to have hobbies outside of your work. Here’s why–if your self-worth is tied to what’s going on in your business, your confidence will get shaken anytime something doesn’t go as planned. 

Business can be unpredictable, and success is a journey, not a one-stop destination. Some seasons might be better than others, so please, please, please don’t feel bad about yourself just because you’re not where you think you should be yet.

11. Remember How Your Services Are Improving Your Client’s Lives

Maybe you think the work you do isn’t important, but I’m pretty sure your client feels differently. Could they even do what you’re doing right now without going stir-crazy? 

Because of your services, your client has a lighter plate and can actually have a life outside of their business. Your services matter and you’re making a difference! 

12. Practice Your Pitch

Actually telling people about what you do is such a good way to become more confident in your business. The more you talk about what you do, you’re going to start feeling more comfortable by default. 

If you’re only pitching yourself “here and there” it’s going to feel a little uncomfortable at first, but the more you do it, it will become second nature to you.

Learn more about discovery calls here!

One way to practice your pitch is getting on discovery calls with potential clients. Another way is to actually get in front of people–be it at a networking event or going from business to business. 

You’re not only limited to professional settings though–maybe you’ll meet a client in other unlikely places like the gym or the grocery store. I heard of a freelance writer who made a business connection while taking his kid to the pool! You just never know where your next client might be waiting. 

13. Get Dressed Every Morning

I know we like to talk about getting to work from home in our pajamas, but actually getting properly “dressed” for the day can make you feel better about the work you’re doing.

Think about it, if you’re already feeling a little iffy about entrepreneurship and you’re sitting on the couch in pajama pants trying to work on your business, you might have a hard time taking yourself seriously. But if you treat it like a real job, get dressed, find a table to work at, and designate specific working hours…you’re definitely going to take yourself more seriously. 

14. Stay Active

You might be thinking–OK Abbey, how on earth is exercising going to help me feel better about my business?

Hear me out.

As an online business owner, you’re likely glued to your computer ALL day. Going outside for some light exercise and vitamin D is going to significantly improve your mood, and in turn, I REALLY believe it will help you feel better about your business. 

If you’re overtired, have been slouching over your computer all day, and not getting some movement…you might feel a little grumpy. How do you think you’re going to feel about the work you’re doing?

It’s ok to take breaks!

15. Speak Up

If you’re usually the one sitting back and taking everything in, it’s time to SPEAK UP! The next time you find yourself in a group setting, put yourself out there and saying something! Whether it’s introducing yourself, contributing some expertise, or just sharing your opinion on a matter…putting yourself out there will help you to become more confident over time. 

16. Be Transparent

Being transparent about what you’re experiencing can actually help you overcome fear. Go ahead…expose those lies in your head. And you never know–maybe there’s someone out there who is feeling just like YOU, and hearing your story might set them free.

17. Don’t Say Anything Negative About Yourself

This is a BIG one that I can’t stress enough.

Please don’t say anything negative about yourself! I know at times we can say things as a joke or to hide our insecurities, but we have to realize that our words DO have power. The way we speak about ourselves is going to get in our hearts and eventually we’ll find ourselves believing what we say…whether we meant it or not. 

18. Mentor Someone In Your Industry

Sometimes the BEST way to boost your own confidence is simply taking the focus off of yourself!

Is there someone you can find who maybe is where you were a year ago? Or maybe even a few months ago? Life is not all about what we can gain, but also what we can GIVE. (And let me tell you, giving is SO rewarding!)

Giving a little bit of your time to help someone navigate their business journey can also help you realize that you have something valuable to offer. 

19. Share Your Expertise On Blogs Or In Facebook Groups

Have you thought about sharing what you know with others? Whether it’s in a Facebook group, a social media post, or a blog post, sharing the expertise you have won’t only benefit your business but your confidence level too!

How good would it feel to see that your knowledge can actually help someone?


FREE TRAINING: Learn more about becoming a booked out virtual assistant!


20. Listen To The Stories Of Other Successful People 

I love listening to inspirational stories about people who overcame adversity to get to where they are today. It can be such a refreshing reminder that even if you don’t have all the privileges someone else has, you can STILL make it. Even if you don’t start out knowing everything, you CAN learn it.

I’ll say it again, success is a journey, not a destination!

21. Have A Plan 

I’m going to go ahead and just say it–maybe you don’t feel confident about your business because you don’t really have a plan for it. 

Here’s the thing…

If you’re just flying by the seat of your pants and you don’t have measurable goals set that you can realistically achieve in the next quarter…you will feel like you’re not getting anything accomplished.

Imagine what it would do for you to have a list of quarterly goals, check them off, and be able to look back and see that you actually did accomplish something?

Your goals can be as simple as book 5 discovery calls in 30 days or reach your first $1,000 in your business. 

22. Show Yourself Grace

It’s great that you want to succeed, but you have to cut yourself some slack too! If you’re always hard on yourself, it can easily feed insecurity because you might feel like you’re not doing anything right.

Give yourself the room to say, I’m getting there. I’m learning. Every day I’m making forward strides.

Learn more about overcoming impostor syndrome here!

23. Stop Overthinking

Let’s have a truth moment here…could it be one of the reasons you’re not feeling brave in your business is that you’re simply overthinking everything? Maybe you’re thinking about all the things that could go wrong or all the people that are so much further along than you. 

Just stop that!!!!

If you’re going to do any more thinking, think about some things that could go right. Think about all the lives you could change (your family included) once you succeed.

24. Encourage Others

I said it already, but I’ll just say it again…

If you’re struggling with confidence, it might be time to take some of the focus off of yourself and see who YOU can help. Helping someone doesn’t always mean mentorship–it can be as simple as finding someone to encourage.

There are SO many people feeling discouraged or alone, but what if taking 5 minutes out of your day to share a kind could be life-changing for someone?


I’ve shared a LOT of tips with you here about how to overcome fear and be brave as an entrepreneur. I REALLY want to hear from YOU…Go ahead and tell me in the comments which of my tips you’ve already tried or would like to put into action.

Read More: Free Virtual Assistant Business Start-Up Plan



Meet Abbey

Abbey Ashley is the Founder of The Virtual Savvy. She helps aspiring virtual assistants launch and grow their own at-home business from scratch. She's since gone on to grow a multi-six figure business and retire her husband ALL from her at-home business. It's now her passion to help others start their own VA business so they can taste the freedom and flexibility of entrepreneurship as well.


This free one-hour training combines thousands of hours of research, years of experience in growing a virtual assistant business!

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  1. Adam S on July 31, 2021 at 8:14 am

    Thanks a lot for your wonderful words here. I can relate myself to many of the issues you have mentioned in this article, moreover it surely going to help me get out with a working solution.

    Keep going and keep inspiring us 🙂

    • Abbey Ashley on August 17, 2021 at 1:57 pm

      No problem Adam, I’m here to help!!!

      • Abdul Rahman Koroma on October 12, 2022 at 6:15 am

        Hi Abbey!
        Thanks for sharing those vital tips. To be honest I overthink a lot and that’s the major reason why I have a junk of stuff half done. I’m on the verge of quitting my job by the end of this year to start something on my own but what ifs are clouding my mind and this is the time for me to be bold enough and embrace what I love to do.

        • Abbey Ashley on October 12, 2022 at 10:46 am

          Hi there! It’s totally normal to overthink or feel nervous about something new! At The Virtual Savvy, we believe in action over perfection! You got this!

  2. Jengleth Baldazo on August 9, 2021 at 3:31 am

    Thank you for sharing this. Stumbled upon this article really timely as I’m just starting out in building my own website and boosting my online presence.

    • Abbey Ashley on August 17, 2021 at 1:59 pm

      Congrats!!! You can totally do this!

  3. Amy on October 11, 2021 at 2:23 pm

    There is a lot of tips here! The ‘dont go by feelings’ was good for me and ‘dont compare’. Thank you for this list!

    • Abbey Ashley on October 13, 2021 at 2:32 pm

      You are SO welcome, Amy! I’m glad this helped you!

  4. Andrea Etheridge on October 11, 2022 at 10:08 am

    I love your tips! 😄On some tips I’ve come out on the other side. On others I’m working thru them. Giving up for me in not an option.

    • Abbey Ashley on October 11, 2022 at 10:49 am

      Thank you so much! I’m glad you enjoyed it! You got this!!!

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