How to Build Self-Confidence to Start a Business or Side Hustle

Failure. Humiliation. These are the anxious feelings that creep up the spine of many of us when considering starting a business.

Triumph. Pride. These are the feelings we need to focus on instead!

It’s easy to say just flip the switch from fear to courage. So let’s turn those words into practical actions! 

As someone who has started businesses that have resulted in “learning moments” as well as successes, I’ll give you the exact keys to unlock your self-confidence to get started!

True Confidence Comes From Prior Success

No “fake it ‘til you make it” mumbo-jumbo here. Think of what you’re actually confident in. It’s in the activities where you have experienced success!

Ideally, your business or side hustle will incorporate some aspect where you feel truly confident in your abilities.

As a wise person once proclaimed, “skills pay the bills.” Where are you skilled?

If you wanted to open your own restaurant, I’d recommend you feel confident in some aspect of the restaurant industry. You might be a terrific chef, always getting compliments on your vegan lasagna and gluten-free sugar-free fat-free key lime pie. Or perhaps you’re outstanding in marketing, or at interior design, or managing teams.

You want to know that one aspect of your business is going to shine!

For instance, I’ve known writers who went from making the website owners who employed them rich to opening their own site as a business! 

Sure they had to learn along the way, but they always knew their writing would be excellent.

So think about where you are special. That thing you currently do as a hobby that generates lots of positive feedback could be your new business! 

For me, it’s making candles that smell like food. My pepperoni pizza candle will be coming to a store near you! 

Start Slowly

Confidence is built up over time as you reach milestones. 

There’s rarely a need to jump into your new business with both feet. Sure you’ll make a big splash, but that​’s also how you drown. Dip your toe in. 

If your little toe isn’t bitten off by a shark in a snazzy business suit, you’ll feel confident enough to put one foot in.

Did you know that many successful businesses start out as a side hustle? I worked for a married couple who started a travel website while they both had full-time jobs as accountants. 

It wasn’t until it was clear that their fun travel site was generating good money that they felt confident enough to quit their jobs to completely focus on their new business.

Proper Perspective Is Essential

Don’t put so much pressure on yourself! It’s OK to “fail.” It’s OK to make mistakes. This is how you learn. 

In fact, you want to fail faster! That means you’re going outside your comfort zone, being brave, and learning. You’ll pick yourself up and march on, this time armed with more knowledge.

I learned that people don’t want a candle that smells like boiled asparagus. They want a bacon-scented candle. 

What’s failure anyway? Imagine your best friend or a loved one. Her or his dream is to make romantic guitar music. This is your loved one’s true passion. 

Would you be disappointed if they gave it their best effort and it just didn’t work out? Or would you be proud that they gave it their best shot? And along the way they did fun shows, were smiling all the time, and lived their best life!

Or would you really be disappointed if your best friend or loved one constantly talked about following their dream but never did? There was always an excuse. There was always a “reason” to procrastinate. 

Be your own best friend. Treat yourself as well as you treat your loved ones. 

Surround Yourself With Positivity

Let’s be real. Starting a business is tough! So make sure to start and end your day with positive talk. 

And talk with the most supportive people in your life. You need optimists to help you focus on the good stuff. 

You should absolutely be aware of the reality of your business, even when it’s struggling. But that doesn’t mean negativity will help you. 

You nee​​d cheerleaders. 

Your friends and family should be your trampoline. You fall down; they bounce you back up. And when you make a strained metaphor, they say, “Hey that trampoline visual wasn’t great but I really liked the pizza candle.”

Celebrate Small Successes

I admit it. I used to feel silly or even ashamed to celebrate the “little” wins along the way. I was like, “I have a big goal. Big deal if I accomplished step 1 out of 10.”

But that was wrong! There’s a reason baseball players get a high-five and clap when they get a single. Sure, it’s not a home run. But it sets up the next play. It’s positive momentum!

Again, would you diminish your best friend’s milestones? If your best friend had a goal to lose 20 pounds and he lost his first 2 pounds I’m sure you wouldn’t say, “Whatever, tubby. You’ve got a long way to go. Maybe you’d be slimmer if your house wasn’t decorated with bacon-scented candles!” 

No! You’d say great job! You can do it!

Your Words Matter

Speak to yourself like you’d speak to your good friend. Never belittle yourself. Don’t be your own worst enemy! 

Stand tall and focus on two things when you speak: your REASON for starting the business and your customers.

“Today I will get another step closer to the freedom to work on something I’m passionate about. Today I will delight my customers who are counting on me!”

Learn From the Best

A shortcut to feeling confident is to get someone who has had success on your side. This could be a mentor, a business coach, or even reading or watching content from a person with a track record you admire.

When I was a kid learning how to ride a bike, I felt better knowing my dad knew how to ride a bicycle and was there to teach me and encourage me. 

When I wanted to learn how to hit a baseball, my dad wasn’t as skilled but he pointed me to books and videos from the best hitters. I felt more confident knowing I was modeling the masters rather than making it all up myself.


The people I’ve been around who do NOT have confidence tend to do the following:

  • They lack skills and do not learn new skills or apply the new skills
  • They have very negative self-talk
  • They don’t seek out mentors or study the masters
  • They lack the courage to try and fail; they prefer to wallow in self-pity

If you want to build the self-confidence to start a business, do the exact opposite! 

  • Select a business or side hustle that utilizes a skill where you’ve had success
  • Talk to yourself like you’d speak to your loved ones
  • Study the best people in your business – they’ve likely written books and done interviews on video
  • Start your business slowly and build up your confidence
  • Know that the only failure is failing to start!

Now go kick butt and build your business!

Scott Lieberman is an online business expert. He teaches entrepreneurs how to make money online. Scott reviews business tools from the best web hosting services to email marketing software. Scott has worked with multi-billion dollar corporations, as well as with small businesses to double their profits to millions of dollars.


Erin shows overscheduled, overwhelmed women how to do less so that they can achieve more. Traditional productivity books—written by men—barely touch the tangle of cultural pressures that women feel when facing down a to-do list. How to Get Sh*t Done will teach you how to zero in on the three areas of your life where you want to excel, and then it will show you how to off-load, outsource, or just stop giving a damn about the rest.

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