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5 Keys to Developing Self-Confidence in Your Online Business

From the outside, becoming an entrepreneur and being your own boss sounds glamorous.

Work from anywhere!

Make more money!

Be in control of your own destiny!

Ha. Ha. Ha.

The truth is, becoming an entrepreneur will bring up alllll your stuff. All your fears, all your self-doubt, all your worst I’m-going-be-a-bag-lady money fears, all your doomsday catastrophizing. When YOU are your own safety net, and you don’t have the benefits and vacation days and regular paycheck from an employer, you better believe shit is going to get real, fast.

So while other corners of the internet are singing the praises of entrepreneurship and selling you a bill of goods on how amazing it’s going to be, I’m here to tell you: it’s amazing, and it’s ALSO hard and scary.

If you’re thinking about making the leap – or if you’re on the other side and you’re wondering if you just totally screwed yourself over, here are 5 keys to developing self-confidence in business…and in life.

#1 – Distinguish self-confidence from plain ole confidence.

Confidence can be limited to the confidence you have in a particular skill or talent. You’re confident in your ability to balance your check book, do paperwork, navigate office politics, pass a math test without studying, talk about Shakespeare, or pour a glass of water.

Confidence can also be limited to your past. You’re confident in your ability to do something you’ve already done.

Self-confidence, on the other hand, is an overall mindset. It’s your belief in your own ability to learn new skills — to create new results in the future, even though you’ve never created those results before.

Carol Dweck calls this growth mindset. You believe that your intelligence isn’t fixed but can grow and adapt. You’re confident that you can learn the skills you need to learn to do something you’ve never done before.

To be a successful entrepreneur, you need to cultivate self-confidence. The next couple points will tell you how.

#2 – Redefine failure.

Do you see failure as a catastrophe, a referendum on your uselessness as a human being, or proof that you’re never going to make it?

Or do you see failure simply as an opportunity to learn?

Ramit Sethi says that if he hasn’t accumulated four BIG fails in a given month, he’s not stretching himself far enough in his business. Ramit is super successful and he’s talking about failure? Say what?

Our culture is OBSESSED with success. Lysa TerKeurst was called an overnight sensation – when her fifth book debuted as a bestseller and she’d been writing more than ten years. We don’t always hear the back story of how long it took someone to get to a point where they achieved what they set out to do. Most overnight success stories are years in the making.

When you see failure as a chance to learn what did and didn’t work, you’ll seek out failure. You’ll fail more … and you’ll succeed more.

If you’re not okay with experiencing failure, you should probably stay in your 9-5.

#3 – Have your own back.

When things go wrong (and they will), do you freak out, berate yourself, and call yourself an idiot who will never amount to anything in life?

When you have a slow month or a launch doesn’t go as planned, do you make it mean that you shouldn’t be in business?

You need to have your own back.

In the same way that you’d fiercely protect your team if you were back at your old job, you need to protect yourself from your mean-boss tendencies.

If you knew that you could make any mistake, fail big, and still love yourself and be kind to yourself, there’s nothing you’d be afraid to try.

So be your own fiercest cheerleader, and don’t make a setback mean anything more than what it is…a setback.

#4 – Be willing to feel any emotion.

If you are truly willing to experience any emotion – grief, anger, resentment, fear, embarrassment, shame – there’s nothing you can’t do. And if that’s not the definition of self-confidence, I don’t know what is.

Because the only thing that EVER holds you back from taking any action is fear of feeling an emotion.

When you take care of your mental health on a daily basis, you can experience any emotion that life throws at you and keep going. When you know what causes your emotions (your thoughts), you can do anything – because you and you alone are in control of your thoughts and feelings and actions.

#5 – Challenge: Dares of the Day

In Brooke Castillo’s monthly program, Self-Coaching Scholars, June is all about self-confidence. And instead of a daily writing assignment, where you reflect on your thinking and your emotions, this month the daily assignment is a Dare of the Day.

Every single day in June, my homework is to do something that scares me.

The idea is that when we trust ourselves to do things that scare us, there’s NOTHING we can’t do. And when we know that there’s nothing we can’t do, our self-confidence grows exponentially.

I pretty much hate this.

Here are some dares I’ve completed to date:

  • Called an old friend I hadn’t talked to in ten years
  • Pitched myself to speak at an event (public speaking terrifies me)
  • Asked for an employee discount at Target (where I’m not an employee)
  • Asked for my purchase to be free at Home Depot
  • Called the parents of my close friend from growing up, on the birthday of her sister who was recently murdered

Here’s what I’ve learned about self-confidence: it feels really shitty while you’re building it. Every day it’s the same for me: the dread of the dare…the discomfort while actually doing the dare…and in most cases, the shame and embarrassment after doing the dare that I then have to do thought work on. I’m working on having my own back, even when I don’t get the result I want, even when people look at me weird, even when I’m afraid I’ve asked for too much or stepped over the line.

I challenge YOU to try doing Dares of the Day for a week. Believe that it’s going to feel shitty while you’re doing it. But believe that you’re going to feel powerful when you’re done.

Go ahead. I dare you.

Tell me a dare you’ve completed in the comments!


June 17, 2018

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