Thinking Big Means planning for success, not failure


Last month I talked about our Evergreen Fund and how we hope to see our applicants dreaming bigger and asking for more money.

But let’s step back. We know how hard this is. Dreaming big and making big asks both run completely counter to the cultural training we have received as women. And it takes hard work to break out of that training.

And it takes guts, confidence, and a level of risk tolerance far beyond most people’s comfort zone.

I don’t know many women who would openly say, “If someone would just give me $250,000, do you know how much I could actually do?”

Most women aren’t even thinking about the impact a major investment could have on their business. Instead, they’re thinking about how to stretch every dollar as far as it can go — a skill they’ve learned from growing up with fewer resources than the average men around them. And it’s scary to put out a statement like that, because someone might actually step up with a check. What happens then?


Thinking big means planning for success, not failure. Women are excellent at planning for every type of failure — and through that planning we often manage to avoid rock bottom — but we often forget to plan for success, and we limit our growth potential.

Many of our members currently run what is sometimes called a lifestyle business. And as we pointed out in the last post, a lifestyle business — a business you run by yourself with no real plan for expansion — isn’t the kind of business that’s typically eligible for outside funding (whether from Doyenne or any other source).

But just because your business falls into the lifestyle category right now does not mean you can’t begin thinking bigger and planning for growth.

Look at Madison-based Breathe for Change, for example. When I first met Ilana Nankin, she was finishing her PhD and starting to explore what it would look like to set up a yoga instructor training for teachers in Wisconsin. Did she ever think she’d train facilitators and take this program nationwide? At that point, she never mentioned that possibility to me. But as she developed the concept, she created a vision and made her business bigger than herself.

Or Amber Swenor, owner of Strategic Partners Marketing, and a Doyenne member. She says thinking big has taken her on an amazing personal growth journey, and led her to expand from a one-woman operation to a team of seven employees and still growing.

“From early on in my business, I decided to walk the walk and have consistently invested in my own training and marketing because I believe in dreaming big, thinking big and investing big,” she says. “I’m proud to have joined the 2% and growing number of women-owned businesses in the United States who have hit the million dollar revenue mark.”

The transition from a solo operation to a growth business requires a vision and the ability to delegate and to give someone else control of your baby.

Letting go of that control and taking the plunge is hard. We experience that even as we work to expand Doyenne into other cities beyond Madison.

But at the heart, it requires that you plan for success. You’re planning for a time when your service will be in such high demand that you must hire more people and expand to new cities.

And your “asks” need to reflect that. But too often, the asks we see are so conservative, that it’s obvious you’re planning for failure, because you’re not willing to take on any risk.

We provide pitch coaching to a lot of women through our 5x5x5 event (coming up August 22nd at Forward Fest) and our twice-a-year Showcase events. We ask the women to prepare for a 5-minute presentation of their business, ending with an ask of investors or their fellow entrepreneurs.


We see conservative growth models — much more conservative than the projections of their male peers. Women respond to the cultural pressure to keep their vision realistic, so they avoid dreaming big.

But beyond offering modest growth models, the women we coach struggle the most with two other parts: talking about their successes so far, and their ask.

They focus way too much on why they are the right person to solve this problem, instead of talking about the success of their product or service so far. At the last Showcase, when our women entrepreneurs first practiced their 5-minute pitch, three of them devoted more than 3 minutes to talking about themselves and how they were qualified to run their business. In a pitch setting, you don’t need to provide that extensive of a background, just focus on what skills you and your team bring to the business. But, likely because of the doubts and the resistance they have faced in developing their businesses sofar, these women felt the need to establish their credibility by talking about themselves more than they talked about the problem they were solving and their solution.

And, secondly, they all struggle with making an ask. They have a hard time standing up and saying, “I need $25K.” But any type of ask is really hard, whether it’s financial or just asking for people to like you on Facebook.

The kind of asks we see are women already planning for the worst case scenario — which is really planning for failure. They’re never planning for success. They may drop in some hype language to try to win the pitch contest, but then there’s no planning for what they would do if they were actually successful. You plan for every worst case scenario, but you’re not planning how you would fill 100 orders in the first week, or what to do if on your opening day if there’s a line around the block.  

That’s exactly what happened to Alex Lindenmeyer, co-owner of Short Stack Eatery (and a Doyenne member).

Everything about the concept and plan for Short Stack Eatery was a product of big thinking:  serving only breakfast, operating as a counter-service brunch spot, offering a small, focused menu with local and organic ingredients, providing benefits for employees, creating opportunities for community collaborations and outreach, and sponsoring social justice initiatives. Not to mention, the founders were two women in their mid-20s.

This vision required significant funding to open — the kind of funding we know many of our members would shudder to imagine requesting. Alex says committing to big thinking required her and co-owner Sinead McHugh to face down dozens of fears: fear of failure; not doing right by their employees, not being taken seriously because they were too young or too female. In the end, on opening day, Short Stack had a line of people out the door and they ran out of food. Alex says they forgot to plan for success. Luckily, they were able to scramble to meet the demand and have become an enduring staple of Madison and State Street, as well a strong provider of employment and a supporter of culinary workforce development in Madison.

Sure, maybe in the final days of preparing for their opening, realism got the best of Alex and Sinead and they stopped thinking as big as they should have, but every step they had taken up to that point was evidence of the huge, audacious vision for a business that could be so much more than a restaurant. And that vision still guides them today, almost five years later.

It’s time to start thinking bigger. And we’ll be here to support you and push you in that journey.