4 Business Mistakes I'll Never Make Again

This is your marathon ― not sprint ― moment.

It goes without saying that the first time ― for anything ― rarely ever reaches perfection. I am the classic ride-the-train-for-as-long-as-possible “first” kind of person. In college, when a professor spoke about anything beyond the syllabus on the first day of school, it was like I’d been wronged. Did they not get the memo? It’s the FIRST day of school!

So when I embarked on my first year of business, I went in giving myself a little bit of grace, knowing perfection wouldn’t be in the cards anytime soon (or ever, for that matter). I’m a creature of having to make the mistakes to actually learn from them.

And boy, learn from them, I did.

1. Thoughtfully decide when to “go big.”

Making your business stand out is what will make you thrive. But test before you invest. If your ideal customer is someone like you, or people you might know, or people in a specific market, ask them their real thoughts on what you’re planning to offer.

I’m not saying spend money on focus groups or even hours reading industry books (which, side note, can’t hurt). I’m talking walk out your front door and ask people what they like. What they need. What will they actually spend money on.

This winter, our store made a holiday doormat, the first product that we solely created, and it was downright exciting. After convincing myself this was the best thing ever, I immediately jumped to, “How many should we make? 500? 350? 200?” This was going to be BIG.

After chatting with friends, friends of friends, and my husband (who was crossing his fingers this silly doormat would work), I quickly went from 500 in production to 70, ensuring all factors were met in order to make it sellable. The design had to be right, the product had to be quality, and the price had to be fair.

Had I jumped the gun at first glance and placed an order for 500, this post may have been titled, “Why You Should Buy A Holiday Doormat In February.” But really, while our costs to produce 70 were higher than what they would have been to produce 500, the experience allowed us to test a new product and see its selling potential. This in turn will allow us to leap a little farther on our next go around.

Whatever your business may be, find a way to test your market ahead of time and thoughtfully decide when the “go big” time strikes. It may take longer in the beginning, but whatever you’re offering will benefit in the end. This is your marathon ― not sprint ― moment.

2. Do it for the “loves” and not the “likes.”

Starting an online business, I knew social media would be something I’d rely heavily upon to grow the company. Yet in a world so dependent on what each of us are individually doing on Instagram, Facebook, and Snapchat, it can be hard to carve out space to get customer attention. I typically pride myself on a positive outlook, but for some reason seeing other companies do social media well ― flawlessly, even ― used to be an instant intimidation factor.

When I started to create content of my own, my outlook for our business was based on the amount of engagement my most recent post had received. If a post did well, we were thriving. If a post did terribly, I wasn’t meant for this life, and I must not be able to hack it. It sounds a little crazy to say that. Whether I deemed myself successful in my own business or not was based on the amount of “likes” I got from total strangers!

Social media can and should be used to grow your business, but it shouldn’t be used to define what you do well. You could be a phenomenal stylist, designer, photographer, event planner or, heck, accountant. Creating a big following takes time and investment, just like any other aspect of your business. You might need to work on finding your target market, making more connections with your customers or participating in more (gasp!) in-person events to really make am impact on your followers online. But remember: Getting all the engagement in the world doesn’t do much if it’s not turning into sales.

At the end of the day, you’ve opened a business to generate revenue doing something you’re passionate about. Take your favorite online influencer, for instance. They are a model, a stylist, a chef, a fitness guru, a foodie, or maybe all the things. That is their craft that defines them. And while they’ve become amazing at showcasing their talents through brightly colored images and beautiful words, their business started at the root of the same thing yours and mine did: that one thing they were passionate about.

Social media can and should be used to grow your business, but it shouldn’t be used to define what you do well.

In your business, make sure whatever you’re doing is the absolutely best it can be instead of focusing so much on how it appears online. Marketing is incredibly important, but the needle doesn’t move without a quality product or offering behind it. In a world where quantity is king, be the business that knows the value of quality customers. The customers who are excited to watch you grow. The ones who dig what you do so much, they can’t help but tell their friends. The girl who loves you, which means she’ll come back to “like” you.

3. Build a brand that’s bigger than you.

When asked who Alice & Wonder was and what we do, my initial reaction was to say, “Alice & Wonder is for girls like me, and we sell things girls like me would like.”

Convincing, catchy, draws you in ― right?


My tone on social media was predicated by what I felt that day. The items I chose to carry were more about what my eye was drawn to than what we, as a brand, should carry. The more I moved forward, the more I figured our brand would formalize itself and customers would just “get it.” I knew who we were. The world would catch on.

It’s these thoughts that make me want to go back and say to myself, “Oh, girl. Stop right there. Do not pass go. Do not collect $200 (or any, because you may not have customers).” Being a brand doesn’t just “happen.” It’s established and built upon. I, the PR girl, knew this was true for my big clients but somehow had forgotten my Marketing 101 when it came to building my own small brand.

Being a brand doesn’t just 'happen.' It’s established and built upon.

Establishing the foundation of your brand doesn’t have to be as hard as it seems. Figure out a way to eloquently say who you, as a brand, are in one sentence. Then, define brand characteristics ― e.g., smart, quirky, elegant, passionate. These will give your brand a personality. And finally, give one sentence to who your customer is. Even if it’s someone like you, describe that person. Who is she? What does she value? Where does she spend her time? Create a voice that embodies that tone and those characteristics.

I had a hilarious manager back in my agency days who always told me our projects should be so buttoned up at all times that I could be hit by a bus the next day and another team member could step in and execute seamlessly.

Morbid? Yes. But the point being, there may come a day that you aren’t executing every move your company makes. A day where you will, dare I say, grow, and your company will become so much more than you. So when that day comes, make sure you’ve built a foundation that tells the world who you are, instead of just hoping the world catches on. 

Friday frills (our favorite kind 😍) #prettyfunthings //💁🏻: @mksportsanista 📸: @ironandhoney

A post shared by Alice & Wonder (@aliceandwonder) on

4. Have absolutely no shame in your game.

I sat with girlfriends the other day, chatting about what makes an entrepreneur successful, and we came to this stunning, yet extremely obvious, conclusion: The people who will go far in business have literally no shame. They see an opportunity? They go for it. There’s a chance an idea could work? They take it. They get shot down 10 times? They ask 10 more. Something fails? They move on. Zero shames given (PG version of that phrase, I know).

I, on the other hand, have always landed myself somewhere between the area of “no shames” and “shame city.” I rarely walk into a networking event solo. I’m into talking about my business, but only quickly, for fear of being too self-promoting. After gathering the courage the ask someone for help, I’ve been known to quickly follow up with word vomit ― something like, “But it’s totally not a big deal if you don’t want to. I shouldn’t have asked. I mean, if you want to, that would be great, but seriously, NBD.”

Giving off that Monica vibe is my specialty. Breezy.

Over the last year, though, it’s been made clear to me that as a business owner, you’ll hear “no” a whole lot more than you’ll hear “yes.” And short of locking the office door and dwelling on all the rejection, a thick skin has to become second nature in order to survive.

When you start a new business, you’re constantly in the realm of asking people for things, which has always been an uneasy spot for me. When you start from scratch, it’s easy to feel like you’re always asking for things and rarely have something to offer back.

The trick I’ve discovered is an easy one: Give them a reason ― a good reason, in fact ― to say “yes.” Can you provide a service for free? Give them an experience they may not otherwise get? Allocate just a little budget to not pay them directly but pay for something they may need? Bring someone else into the offer that they might be interested in working with? The more creative the request, the more I find people appreciate the offer.

As aforementioned, I still receive my fair share of “no,” or worse, no response at all. But as a whole, I’ve been pleasantly surprised by the amount of people I’ve been fortunate enough to work with, learn from, and even create friendships with ― all because I didn’t give them a reason to say “no.” Maybe you land in the realm of 10 requests sent and only one offer accepted. But as along as you end up with zero shames given, you’ll be just fine.

Ali Reff is the owner of Chicago-based apparel and gifts shop Alice & Wonder. Nicknamed “Alice” by her family, Ali started Alice & Wonder in 2015 after leaving her job managing influencer relations and real-time engagement for McDonald’s. The inspiration to start a small business began after Ali moved to Chicago and quickly discovered the city lifestyle can come with a price tag, and budget-friendly style shouldn’t be so hard to find. Since the company’s inception, Ali began writing pieces on her small business journey in hopes of inspiring other strong female leaders to pursue their passions and share her learnings along the way. Ali lives with her husband in the Lincoln Park neighborhood of Chicago and can best be found over on Instagram @aliceandwonder or via email: ali@aliceandwonder.com.