9 Confidence Lessons I've Learned From Starting a Business

If you don't believe in you, no one will.

Jun 9

Good day, everyone.

Happy summer. I’ve been popping Brut Rosé like there’s no tomorrow and I will not apologize for it. Summer is cocktail season and I am at peak carefree-ness.

Contrarily, I have recently launched my clothing brand (wee woo!) which is giving my carefree-ness a “serious” tint — someone I don’t get along well with.

This week’s newsletter is for anyone starting a new venture — be it a business, side hustle, or even a new workout routine (hi outdoor jump-roping and squats!) the bottom line is…if you aren’t confident in what you’re doing, no matter what that is, you’re going to struggle.

I’m here today to make you feel less alone in your bravery pursuits, give you some confident lessons, and hopefully make you laugh. Here we go.

What, like it’s hard?

You know what advice is stupid? “Starting a business is going to be hard work.” Um, okay? Care to provide some specifics around that, or?

Starting a business has been like everything else *new* that happens in life. Have challenges come up? Yes. Have people talked to me like I’m an idiot? Yes. Have I been having fun? Yes.

Here are the lessons I’ve learned thus far in starting my biz…

Acting like you know what you’re talking about (when you don’t) is stupid.

Ask the questions that need to be asked without fearing you will look stupid. In the beginning, you probably will. And who cares if you do.

I did this on a phone call yesterday with a “high-end” manufacturer. Side note: High-end = snobbery. She asked about my project needs, and after explaining my vision to her she said, “You’re saying a lot of words that don’t go together. Everyone wants to be luxury but so few people get it.” And then she laughed.

While her bitchy response irked me, she was probably (maybe) right. And while I despise condescendment, I appreciate directness. Like Rebecca Minkoff says, “If you don’t have thick skin in business, you’re not going to get very far.” So thick skin I grew! In that moment anyway.

Comparing yourself to other people who have been in the game for 40+ years makes NO SENSE.

Or 5 years or really any length of time longer than what you have put into it. This is self-help-guru-y, but you should only be comparing yourself to the person you were yesterday. Truly.

Comparison really is the thief of joy. Nothing productive comes from comparing yourself to someone else. Collaboration over competition, guys. It’s so much more enjoyable.

If you are not being 100 percent you, you are setting yourself up for failure.

This can sometimes be a difficult thing to be in business because you’re supposed to be “professional.”

For someone who preaches mantras to BE YOURSELF!! for a living, I really surprised myself as to how not myself I was when discussing my brand with “higher ups.”

While there is a tactful way to finesse your personality in situations that call for more “business speak,” you still have to be you. Your you-ness is what dictates your success.

Going with your gut is always the right answer.

Again, for someone who shouts this concept from the rooftops, I was surprised at the times I leaned into someone else’s advice over my own intuition.

I assume this gets clearer over time, but in the beginning, it’s tricky to decide what’s right for your business when you have so much newness and uncertainty thrown at you.

Reminding yourself of the “Why” of your business is crucial to your success.

I learned this from Ana & Klas Kristiansson, fashion business experts / husband and wife power biz couple.

During a fashion business course I took with them, they hammered the idea into our heads that the “Why” of your business will guide every single decision you make — from the fabric you choose to the manufacturer that’s right for you to the language you use on your website.

Anytime I’m stuck on a design decision or don’t know who I should collaborate with for an event, I ask myself my business “Why” and the answer becomes *crystal* clear.

Finding the right people to work with is key.

I’ve said this once and I will say it again — I would rather be raking leaves with someone who makes me a laugh for a living than having my “dream job” with a boss who is a total brat.

Even if you’re a one-man team (hi!), you work with your customers at the very least. On that note, keep in mind your vibe attracts your tribe.

If you don’t believe in what you’re selling, no one else will.

I DIED when my dressmaker showed me the kimonos she HANDMADE. There is no cooler feeling than seeing something you’ve dreamed up in your mind sit right there in front of you to touch and ogle over.

The kimonos I designed (and my fashion taste in general) are a very specific look. They are not for everyone, which is what makes them so cool and special.

My point is…If you aren’t excited about your products and your business overall, no one else will be.

You MUST find ways to keep yourself motivated every day.

And it has to be more than looking forward to your morning cup of coffee and your evening glass of wine.

For me, it’s listening to business podcasts, humor podcasts, and loud music, taking long walks, forgetting about my phone, perusing pretty places like boutiques, book stores, and organic markets for inspiration, reaching out to people in the industry for advice, and committing to four solid hours of work per day.

Any entrepreneur will tell you that “the highs are sky high and the lows are dirt low,” and they are correct. Both of those extremes are fleeting, so you have to find ways to keep yourself excited about your business in the in-between times.

Doing one thing that makes you uncomfortable every day goes a long way.

Another self-helpery tidbit of advice! It works wonders, though.

For me, this is telling a mom at a park about my line, showing her photos and asking her opinion about the looks.

Instead of thinking, “What if she thinks I’m being self-promote-y?” I think, “What if this is the clothing brand she has been searching for all her life and I am the one giving it to her?!”

Being delusional can really work. At the very least, it’s a true mental health hack.

Takeaway

Your you-ness is what makes you fabulous, even in business. Don’t water it down for someone who thinks you’re too extra. If you believe in yourself and in your business, you will be successful. Whatever successful means to you.

Cheers!

Thank you for reading :)

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Be you.

Xo, Ash

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