Whitney English’s eyes twinkle behind tortoise-patterned glasses, like she’s up to something mischievous. Whitney’s style is all business– stylish specs, a well-steamed blazer, and perfectly curled, tumbling blonde hair. Yet, despite the bright prints and sorority alum-approved attire, Whitney English has a rebellious air about her.
“I always joke that I was the member in bad standing,” she says, referring to extracurricular activities during her college days. We have the same alma mater– Oklahoma State University – and we were equally bad at group activities.
Entrepreneurs, it seems, go their own way. No one knows that better than Whitney.
She smirks often and is quick to laugh. Whitney carries the quiet confidence of someone who has sat comfortably at the top, landed hard at the bottom, and got back up to try again. After 15 years as an entrepreneur, she has plenty of success – and a few failures – to draw from.
Whitney is the face behind Day Designer, a planner for creative professionals, busy mamas, and girls-on-the-go that debuted in 2012. The signature black-and-white-striped, hardcover planner is recognizable almost everywhere, but this wildly successful business wasn’t her first rodeo. Whitney built her first business years before, only to file bankruptcy and start all over again.
“At age 26, my company was doing seven figures in revenue and I was walking through the airport in Prada heels feeling like I was on top of the world,” Whitney says. “At age 33, I was eating rice and beans every night for dinner because my husband and I could hardly make ends meet.”
Today, Whitney is sharing her knowledge with other creative in her #BizDesigners ecourse – a crash course in crash-and-burn business mistakes, bootstrapping a dream job, and how to make products and services that spread like wildfire.
She sat down with Spitfiremom Society to talk about the importance on entrepreneurship, how to create a dream job, and the best mom advice she ever received.
Tell us about the Day Designer journey:
There wasn’t a planner on the market to fit my needs. I’d always wanted to design a planner, but never had what I call “the white space.” I think people create best from a void – from nothing. I had that space after the first company closed.
That’s where Day Designer came from.
Tell us about the first business:
On the outside, the business looks like it was going gangbusters. But, it went under for so many reasons: we were in an economy shift and some massive, disruptive changes in technology were happening in the printing, online invitation space.
You learn twice as much on the way down as you do on the way up. I’ve had so many down moments, and now I strive to help other people experiencing similar struggles in business.
In the middle of all that chaos of a business closing I had to regroup and reframe what was important and what I was going to prioritize. That’s where this story starts to get good.
What’s different about how you run a business this time around?
One of the things I think I’ve had to understand is that I can design a business around the kind of life I want. I can design a life and business that I want to live. It does mean being slightly unconditional about stuff at times. But, it works, right?
How did your business change after becoming a mom?
It changed drastically with kids. It just never dawned on me that just because there are more people in my life – i.e. husband, child 1, 2, and 3, that that meant there are fewer hours in the day to get stuff done. I completely underestimated that and found myself overwhelmed at times.
What are some of your non-negotiable conditions?
I’ve always been told from other moms that it’s really important to pick your kids up from school. That time in the car is when they really talk to you. Then that’s it, they get home and on the computer or start homework. Other moms have told me: whatever you do, get off at 3 o’clock and go pick your kids up from school. I’m trying to make that commitment.
I also don’t do business phone calls when they’re around. Other professionals – men, – still expect you to have a professional conversation. And even some women are hardcore, asking “Where is your babysitter?” So I try to be professional in those settings. Every now and then, you’re lucky enough to work with another creative who gets it.
What has been your best investment, in business or in your personal life?
I have a sitter at home, a lock on my door, and noise cancelling headphones. I work from home with my kids, so childcare at home as been a huge investment.
How has your creativity changed after being a mom?
My creativity is a lot more scheduled. It’s less design-when-the-mood-strikes and more scheduling. Steven Pressfeild said “ I do have a creative muse. She strikes at 9 am every morning.”
The writers I know call it B.I.C – butt in chair. Its not “oh, I’ll write when I feel like it.” It’s putting it in the calendar. You wont feel like you perform better that way at first. Just put something on paper even if you don’t feel like it.
Do your kids know what you do for a living?
I went to Alt Summit one year and came back with piles of swag. I gave it to my son who was really young at the time. He found these stickers with black and white stripes, and he said “Look mama, it’s yo stuff!” [Laughs] It was a compliment to the brand.
You have a super impressive social media following, especially on Instagram. What advice do you have for moms who want to grow their following?
As a creative entrepreneur, if I’m being honest, I spent a lot of time on my phone.
It takes a lot of time. I’ve hung out with moms with three kids who post on Instagram 3,4,5 times a day. I’m with them when that happens, and they are not with their kids.
I tell people: you’re not going to become a successful entrepreneur by sitting around on Instagram all day. Go to conferences, apply for workshops, and don’t be ashamed about saying “I’m just getting started. I’m on a mission.” It’s really about how long you can stay in the game, not who gets there first.
What’s the hardest part of being a mom and an entrepreneur?
I just have to remind myself, and I want to remind other moms, that kids are only this young once. My son is starting to read. Teaching a kid to read is a full-time job. Its tough, but I have to do the best that I can and know that’s enough.
How do you handle critics – of your business or parenting style?
I’ve had naysayers. I love good criticism if someone says it in a constructive way. Critics who criticize just for the sake of being heard, or even connection? Ain’t nobody got time for that.
I don’t do mommy wars. There are people concerned about that their stroller looks like. I’m not that person. I have to shrug it off, realize I’m different, and find other people who are different, too.
What advice do you have for a new mom?
I would say is “It’s not going to be that bad.” You do have to find childcare, on a basic level. Being pregnant and working is not hard, at all. Maternity leave – the first three months you’re trying to figure out how all this stuff works, like feeding and diapering and schedules. That’s tough. I would caution new moms to not overschedule themselves at that point. With my first, I did. I thought, “I can work when he naps!”
Two kids is a game-changer. Three kids, especially if they’re as close together as mine are, brace yourself. It’s brutal. [Laughs]
What do you love most about being an entrepreneur?
Society says grow up, graduate from high school, go to college, get a job. Get a nice, stable job with benefits that you can work at for forty years. And then retire, and then when you’re old and don’t feel like doing anything, do some stuff.
I believe the world would be a better place if people thought more like entrepreneurs.
You don’t have to sit at a desk if you don’t want to. As an entrepreneur, you start with less but you end up with more – in dollars and in experiences. Both of the businesses were successful – we made money more years than we didn’t. We started with nothing – it was bootstrapped: a little bit of babysitting money and a lot of leaning on friends and family, taking leaps, and figuring out how to get there.
Do you imagine your kids growing up to be entrepreneurs?
I worked for a lot of entrepreneurs growing up. I hope my kids, growing up, get that same influence. I did have a lot of entrepreneurial influences that put me on that course.
What is next for Day Designer?
I don’t think this is my forever thing. You’ll reinvent yourself multiple times as an adult.
Thanks so much for sharing, Whitney. We are in love with what you’re doing, especially in encouraging other entrepreneurs. We are inspired!
Jess, Heidi & Jenn
Know a fabulous, creative mompreneur? We want to hear about her (or YOU)!