12 Lessons from Small Business Rule Breakers

no rulesOver the past 2 years, I’ve interviewed almost 200 women about how they manage running their businesses, their families, their health and their sanity. Each woman I’ve come across has taught me so much about doing things THEIR way, regardless of how things are “supposed” to be done. I’m consistently surprised at how sometimes, what’s good for everyone else ends up to be the opposite of successful for one individual. But what it comes down to is this: running your business, YOUR way, is really the only way that is the right way.

Lesson 1: Being Yourself, At All Costs

So many small business owners are advised to be conservative and appeal to everyone when naming or marketing their businesses.. But it wasn’t until they gave in to those parts of themselves that their businesses really took off. “When I first started out people warned me of alienating people if I mentioned God on my website, blog or about me page,” says Rachel Luna, owner of The Tailor Made Life. “I said forget that to all those people and my business started growing exponentially once I started honoring my values and message.” Denise Duffield-Thomas, author of Lucky Bitch and Get Rich, Lucky Bitch, agreed. “ When I called my company “Lucky Bitch”, I had a few pearl clutching messages telling me how unprofessional it was, but I knew I wanted something bold and memorable. I’ve never regretted it and attract women who love identifying as a Lucky Bitch.” Both of those are extreme cases, for sure! But it shows that no matter who you are, being true to yourself is the most important thing.

Lesson 2: You Don’t NEED a Niche

Marketing and branding experts will tell you that you won’t be successful until you really drill down either WHO or WHAT you do, very specifically. But many small business owners are able to ignore this one with great success. As Nicole Longstreath of The Wardrobe Code asks, “ Why shouldn’t my message be spread far and wide, instead of just to one small ‘niche’?” Her audience ranges from small business owners to company execs and her business has grown like crazy this year.


Lesson 3: You can break your own industry rules.

Are you a copywriter who doesn’t follow the AP Stylebook? Maybe you’re a marketer who doesn’t believe in press releases. Regardless, doing things your way can still work out for the best. “I’m a writer,” explains Nikki Groom, “but sometimes the most powerful writing emerges when you break the rules. Who cares if you start a sentence with ‘and’? The important thing is that you convey what you need to say.”

Lesson 4: Working harder isn’t always working better.

Many successful women thrive with less working hours. How? By outsourcing, creating systems and forcing themselves to take a break. “Focus on smart work time,” says business coach Jenny Shih, “I usually shoot for 20 hours a week… and still made nearly $300k last year.” Leonie Dawson has also never worked full time in her business, and she says she has incredible work/life/family balance.

Lesson 5: You can quit your full time job without a clear plan.

Sometimes, the best thing to do is just jump. Going somewhere, even if you’re not sure where, is better than staying in the wrong career. Maggie Patterson, PR consultant, quit her job 9 years ago and is “still rocking it.” Jenny Shih also quit her job even though she was the primary breadwinner. She saved up money,” took the leap, and did everything I could to make it happen.” Many people would advise against quitting without a plan but when you gotta go, sometimes you gotta go.

Lesson 6: You can, and should, give away your services for free.

This is one of those lessons that perhaps you’re cringing while reading. I know it surprised me! But for some business owners, this leads to massive growth. “Writing pieces for free/trade got my foot in the door and gave me a great working portfolio,” says Laura Viviana, copywriter, “which helped land my first agency gig.” Caroline White also advises to give away almost everything for free, “except the one thing you do the best, and charge a lot for that.” Leonie Dawson has a very generous business model, as well – her programs are often 80% off and she gives everything she creates to that one program. And she’s been enjoying six figure months for quite a while.

Lesson 7: You can market yourself any way you want.

Even though we’re told you HAVE to be on social media, or blog, or email, many business owners do better when they stick to what they LIKE to do and not what they HAVE to do. Leah Manderson, financial consultant, is barely active over social media but does GREAT with email marketing. Leela Somaya doesn’t blog OR email her list consistently but focuses on lead generation and sales instead. Both women have consistently grown their businesses even though they don’t follow the typical “shoulds” when it comes to marketing and outreach.


Lesson 8: You don’t need a business plan.

Business planning is hard. But we have all, at one time or another, been made to feel like if we didn’t have written out our exact profit and goal strategy, we were failing as a business owner. Not so, says Hitha Palepu, author of the popular travel blog Hitha On The Go. “I never wrote a business plan for Hitha On The Go,” she explains, “What started as a personal blog grew to be a lifestyle website and then a travel and packing destination for women travelers. Being flexible to pivot the focus of the website to what it is today.” Lorrie King, founder of 50 Cents. Period. agrees. “Everyone tells you before you start a business or organization you need a business plan, but that’s not what we did. “When I went to India and  saw how something as simple as a lack of sanitary pads kept girls from going to school, I just jumped into solving the problem.”

Lesson 9: Fast and big isn’t always better.

Most business owners want to grow and achieve right off the bat. But some of the women I’ve spoken to have found when they take things slow, business goes better. Jamie DuBose of Zenplicity says she’s better able to focus on client needs when she’s going at a slower pace, and her business grew organically as a result. Sylvia Hall, life coach, agrees and says one conversation and client at a time is best even though it’s a foreign pace for most.

Lesson 10: Charge what people can afford, not just what you think you’re worth.

Depending on your services and your customers, your prices may not match what you’re able to get in your market. Many business owners struggle because they’re often told to charge more, even though their customers don’t have the investment to make. “You have to factor in what people are willing to pay,” says Laura Belgray, copywriter at Talking Shrimp. “Even the big spenders.” Victoria Prozan agrees. “Price according to your heart, not what you’re ‘worth.’”

Lesson 11: Make your OWN rules, as you go along.

Many of the women I interview often tell me that they don’t even KNOW the business rules I’m referring to. They work off of intuition, even if they’ve “stepped in a few cow piles,” says Dr. Kelly Edmonds. When you start, you don’t always know what you don’t know, so you just do your best until you can figure out what works for you. Tena Pettis, owner of tena.cious states that because was winging it, “I broke every friggin’ rule there was.” But when you know better, you do better.

Lesson 12: Follow your intuition.

If something doesn’t feel right to you, no matter how good the advice is, you can’t do it. I have so many individual examples of this, I couldn’t possibly list them all. Lori Cheek, Founder of Cheek’d, says she was advised over and over not to take meetings and phone calls with everyone who asks. People told her to set boundaries so she didn’t waste her time. “The reality is that my networking and real-life connections I’ve made all over the world have lead to the ultimate state of my business. I will keep saying ‘YES, YES, YES!’” Christie Halmick, owner of Jewels Branch Creative, completely halted her business and stopped taking clients so she could focus on creating an online design course. Many women I’ve interviewed started luxury businesses at a time when the economy dictated their businesses would fail – but they didn’t.

The bottom line is that your business can succeed no matter what “rules” you break – as long as you’re doing business well. Making money is only part of what makes a business successful – being customer focused and fitting your business into a life you create is equally as important. As small business owners, we are advised and often ridiculed for not doing things the traditional way, or not planning as well as we should. Even worse, we tend to worry and obsess over the things we haven’t done, even though we “should” – when the truth is that when we smartly decide what’s right for ourselves and our customers, we end up being way further on top that we expected.

What business rules have YOU broken or feel are hogwash? What rules have you followed against your better judgement? I’d love to hear your experiences with rule breaking below!

Jessica Kupferman is the Gordon Ramsay to your online business Kitchen Nightmare. Woman entrepreneurs hire her to bang out brilliant brands, create products and services that fly off the shelves, and find ridiculous business success while making their own rules. You can also find her interviewing fascinating lady-preneurs for her podcast, Lady Business Radio and teaching NEW Lady podcasters in her course, Podcasting School for Women. She also co-hosts the only podcast BY women, FOR women, called She Podcasts with Elsie Escobar, social community manager of Libsyn. To check out more about Jess, visit LadyBusiness.biz for recent episodes as well as freebies, featured articles and more.

Image courtesy Môsieur J.

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1 Comment

  1. Most companies, whether big or small, direct their marketing to select niche audiences. Even the country’s largest manufacturers target carefully pinpointed market segments to maximize the effectiveness of their programs and often tackle different niches for each product group.

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