You’ve heard of resting bitch face, right? Well, apparently, I have resting chill face. Everyone assumes that I’m calm, collected, and never stressed about anything. ‘Denise, you’re so relaxed!’ they say. ‘What’s your secret?’
Maybe it’s because I’m Australian: as a nation, we’re notoriously laid-back, and our unofficial motto is: ‘She’ll be right, mate.’ But the truth is, I wasn’t born with a happy-go-lucky personality: I’ve consciously learned how to cultivate that attitude. Remember the book Don’t Sweat the Small Stuff… and It’s All Small Stuff? Well, I used to sweat everything. Literally. Anxiety often made me a sweaty, stinky mess. And then I’d get worried about that too.
In my early days as an employee and a fledgling entrepreneur, I was riddled with insecurity. I worried about everything, but especially about making mistakes. I second-guessed every word I spoke or wrote, and constantly thought:
I was terrified of opening my email inbox because I was sure I’d find bad news, like a complaint, a refund request, or hate mail. In snail mail, I just expected bills, parking fines, or speeding tickets. I was afraid of getting things wrong, like which system to use, which book to write first (I’ve always had a million ideas floating around my head), or whether a specific coach was right for me. I was in analysis paralysis because I second-guessed myself at every turn, and the consequences of making the wrong decision seemed catastrophic.
I even worried about what would happen if I did become wildly successful. I had a recurring nightmare about being a regular on Oprah’s show and having to wake up at 4:30 a.m. every day for hair and makeup. I’d lie awake and stress: ‘But I like my sleep! How do I say no to Oprah?’ I barely had a business, but I had tons of worries about it!
Personal development helped a lot. Through it all, I had an underlying belief that, one day, I would be successful, even though I was so often anxious. I always had big dreams and just knew I’d be a millionaire one day.
I always wanted to run my own business. Even as a kid, I was the ‘go-to’ girl for others. I had a knack for breaking down people’s problems and helping them, even if all I did was reassure them that, somehow, we’d figure it out together. When my friends’ parents thought I was dealing drugs to their teenagers, I was just selling self-help! ‘Don’t worry, let’s journal it out,’ I’d tell my friends. Or I’d parrot Oprah advice I’d heard on TV.
My academic advisor at university laughed at my A+ grades in marketing and my Fs in economics, statistics, and accounting. ‘Denise, you’re so creative, but your assignments are full of BS,’ he said. ‘In 10 years’ time, you’ll either be a millionaire or in jail for fraud.’ Well, here I am, free as a bird, a self-made millionaire using my powers for good! Rather than learning to be a better statistician or economist, I doubled down on my creativity and became an entrepreneur!
When I started teaching my first personal development workshops (at age 19), I was surprised that people listened to what I had to say. Even though I was just regurgitating the words of the male self-help gurus of the time, people believed in the borrowed confidence that helped me believe in myself.
Slowly, slowly, I got more traction in my business, until I became one of those 20-years-in-the-making ‘overnight successes’ and could legitimately call myself a millionaire. Along the way, I got more chill about making mistakes (I still make them all the time), and I stopped caring (as much) about whether everyone liked me. I finally learned not to sweat the proverbial small stuff.
The idea of being a Type A personality never quite resonated with me – although I’m hardworking and ambitious, I’ve never been about winning for the sake of winning. I’m not really competitive, even though I have high standards for myself; Type B seemed more my style. But I realized there’s a third category that’s even more my style: Type C – a chilled, ambitious-but-lazy, wants-to-change-the-world-but-also-thinks-there’s-an-easier-way person.
That’s what this book is about. I’m not going to teach you how to hustle or tell you to get up earlier (the older I get, the more I realize how important sleep is). I’m actually going to teach you the opposite – business really doesn’t have to be that hard! You can get to a place where your business supports your dreams but doesn’t burn you out. Where you feel ‘enoughness’ at the end of the day, but you’re excited to achieve your next big goal.
There’s never been a better time to be a woman in business, and the opportunities before us are mind-blowing. Freedom and independence can be yours with just a little bit of upfront work. I don’t understand, technically, how the internet works, but the tools we have available to us are magical and life-changing.
When I count my blessings and write my gratitude list, you’d better believe that techy geeks are on it, because they helped me change my life, and in turn, the lives of thousands of other women. All hail those Silicon Valley dudes (let’s face it, most of them are men). They might not be the most feminist people, but they’ve created opportunities for women like us to gain an unprecedented level of economic independence, and for that, I’m grateful.
Being an entrepreneur once required a lot of upfront capital for machines and stock, or techy know-how. It felt official and serious, like a title that was bestowed upon you (maybe even by a business school). An entrepreneur was either a crazy inventor or a door-to-door salesman. You were restricted by where you lived, so too bad if that was some crappy little town in the middle of nowhere.
Hey, but not now! Today, anyone can start a business, good or bad. As long as you have internet access, you can sell glitter penis-grams from your tiny house in Nebraska. You can design websites from the beach in Tulum, Mexico. Or you can run a global coaching business from a small town in Australia (even with crappy internet), which is exactly how I got started.
There’s no limit to what you can do. Not everyone will succeed the first (or 40th) time, but while failure used to mean bankruptcy or piles of unwanted stuff in your garage, now you can just close up your (Etsy) shop and try something else. No big deal: there are plenty more ideas in the sea! Women are succeeding more than ever and are finally seeing entrepreneurship as a viable vehicle for supporting their families, for creating wealth for themselves and others, and for changing the world.
But it’s not all sunshine and roses. Even though women (especially women of color) are the fastest-growing group of entrepreneurs, we come with a lot of built-in obstacles. Being an entrepreneur used to mean men in suits, and now it’s bro-dudes in hoodies. Women’s businesses aren’t always considered ‘real enterprises’ or respected by mainstream entrepreneurial publications. There’s a very real wage gap in the entrepreneurial world, too. But nobody can work harder than a woman with a dream, and most women I meet are more than smart and creative enough. The biggest problem is that we’re still trying to fit our businesses into an old, masculine model. And that’s exhausting!
I love business books, but at some point, I noticed the usual ones stopped resonating with me. So much so that one day, I briefly considered throwing the book I was reading across the room. I may even have sworn at it.
It was a bestselling title about how world-class performers live and work, and the case study I’d just read featured a ‘successful’ entrepreneur who got up every day at 4:30 a.m. to work on his blog, went to the gym at 8 a.m., then headed to the office, where he worked until 6:30 p.m. After that, he went home, had dinner, and spent an hour with his wife and child; he then worked again from 9 p.m. until 1 a.m., slept on the couch, and woke the next morning to do it all again – on three hours’ sleep.
I actually wrote ‘WTF!’ in the margin. My first thought was, He has a kid? And a wife? My second thought was, Wait. This is success? These business books were full of talk about ‘crushing your goals’ and ‘killing your competition.’ It was the old, patriarchal nonsense that still permeates entrepreneurial culture.
‘I am endlessly fascinated that playing
football is considered a training ground for
leadership, but raising children isn’t.’
DEE DEE MYERS
But at the beginning of my business, I didn’t know any better. I regularly woke at 4:30 a.m. to work with international clients. I worked day and night. I dreamed about clients and spreadsheets in my sleep. I never had time for friends, let alone decent meals. I was obsessed with ‘making it’ at all costs, and it wasn’t healthy.
Everyone’s version of success is different, but most of the women I talk with these days have lost a certain amount of richness in their lives. They feel like they’re working harder than ever for diminishing returns, both in a financial sense and in satisfaction with their work. They are missing the joy.
Hustling for cash is exhausting. Most of us are juggling our business dreams with partners, kids, family obligations, school, waxing appointments, and just life. You don’t want to work all day and night. You want time to go to the beach, get to that yoga class, see your friends and family, and be a more present partner, mother, sister, and friend. And you can. But it’s really common to get sucked into the trap of: ‘If I want more money, I have to work harder.’ Most of the methods we use in our work, and the books we read, have been created and governed by masculine models of success. I never questioned that until I burned myself out.
‘Entrepreneurs are the only people who will
work 80 hours a week to avoid working
40 hours a week for someone else.’
LORI GREINER
Why was I waking up at 4:30 a.m. when I started my business? Well, I had clients on the other side of the world, and I felt bad about asking them to work with me outside their normal hours. (Oh boy, we’re going to have an honest conversation about boundaries later in this book.) Why did I often pull all-nighters? I once worked on a sales page all night, followed by three straight hours of coaching calls, and then delivered a live webinar – all on no sleep. I did this because I felt terrible about the idea of hiring someone and asking for help. If you suck at this, too, don’t worry: I have some tips for you later.
Back then, my friend James Wedmore told me, ‘Denise, you can’t get to six figures by doing it all yourself.’ My answer? ‘Watch me.’ Yeah, that’s stupid. But when I did hit six figures, I felt a massive wave of discouragement instead of celebration. I was a ‘success story,’ but not really. My success didn’t feel sustainable (in truth, it felt like a massive fluke), and there was no obvious way to increase my income without working harder. I was already stressed and tired.
In my early days in business, I met a fellow coach who told me she saw 100 clients a week. My first thought was, When do you pee? My second was, Oh my God – I energetically max out at 15 clients a week. I probably made the same amount of money as she did, and I instantly felt guilty for working fewer hours than I ‘should.’ Maybe I should see 100 clients? I thought. What’s wrong with me?
I honestly believed that taking any shortcut was lazy, instead of smart. But the truth is that we’ve all started our business for the freedom and flexibility it gives us, not to replicate our old jobs, and definitely not to do more work for less lifestyle. I wanted a business that helped others, was wildly profitable, but didn’t suck all my energy and time or leave me a husk of a person attached to my computer screen. It was time for a new breed of entrepreneur. It was time for the Chillpreneur.
I know, I know. Everyone is some type of ‘-preneur’ these days; it’s beyond cheesy. But most of the heart-centered women I know don’t want to hustle anymore. We don’t want to ‘crush’ anything, especially not the competition. We want to collaborate with other women, not kill them! We want everyone to succeed. And we’d also love to have the time to create a garden, have a hobby, or get our hair and nails done occasionally.
Is that too much to ask? No.
As you’ll discover in this book, being a Chillpreneur isn’t about swinging around in a hammock all day long (I’ve been in a hammock twice in my life, and I fell out of it the first time) or living in Bali (though you can be a Chillpreneur there, too). It’s about finding a new way of doing business: one that works for your bank account and supports your wellbeing; one that works for you and the planet; and one that follows the path of least resistance.
Hear this from a recovering perfectionist workaholic who is now a pretty chilled-out millionaire with young kids: it’s possible, and this book will show you how.