5 secrets I learned from successful women CEOs

Huda Idrees —  Photo by Chris Chan

Huda Idrees — Photo by Chris Chan

*Originally on Medium*

Around summer of last year, I gained a lot of weight. Very quickly.

Turns out, the security/fear of settling in a ‘home’ + unhappiness at your well-paid, full of benefits job = 40lbs worth of stress.

Some dreams aren’t all they’re cracked up to be — and some jobs aren’t either.

I’m not 100% sure how I convinced myself that I was eager, willing, and ready to take on the entrepreneurial world, but I think the inconsistent expectations, office politics, and moral turpitude of my 9–5 played a part.

Oh, and the extra 40lbs were a hint. Even though I was hitting all the stereotypical 20s “goals”: not all was well.

With the support of those closest to me, I decided to buck up, build my own business & take hold of my own stress.

Building my business is what helped me change the “I CAN’T BELIEVE THIS OVERWHELM” stress into positive “I’M BUILDING SOMETHING AND IT’S SCARILY FULFILLING” stress.

So, I handed in my resignation to start Wild Geese Creative Co. — a conversion copywriting company that blends the research, data, and analytics I’d started to obsess over, with my love of persuasive copywriting. A company that I could care about, would be proud to talk about, and invested in the business ideas that I wanted to use my words to lift up.

Through my research + startup process, I listened to ALL the podcasts, read ALL the business blogs, and invested in AT LEAST 2 courses to get my mind right. And this is what I learned along the way: these are the things that helped me overcome my fears, sleep sounder at night, and get my g’ddamn shite together.

These 5 lessons are what solidified my path to entrepreneurship, and, if this is your path? Hopefully, yours too:

#1: Be a human first, business second

REALITY: The traditional workplace wasn’t designed for women.

And even “modern” workplaces still all-too-often result in women feeling ostracized, fearful, and unnecessarily competitive.


Instead of leaning into the idea that we can all prosper, we’re forced into competition as productivity.

Whitney Wolfe — who I feel like is everywhere lately — is a champion for readjusting the power balance at work and is unashamed of her femininity with her company, Bumble:

“Because women make the first move on Bumble Bizz, I think we’ll be able to combat the power imbalance in the workplace and the often unnecessary gray area that emerges when people abuse networking with ulterior motives… And there’s no question that what I’ve gone through has informed who I am as a business person today. As for the space, it’s really all about reflecting the themes of our brand: kindness, self-respect, fun, and a celebration of female empowerment.” — Whitney Wolfe, CEO, Bumble

In March, I was grateful to be half of the team that organized the Inspired 2 Action Conference in Toronto. It was a half-day workshop for budding women entrepreneurs who wanted guidance on where to start, and how to validate their business ideas.

MOMENT OF CLARITY: Women doing it their way.

Tammy Price, Medical Intuitive, was one of the speakers, and one of the things that struck me as she was speaking about deconstructing the relationship between mind, body and spirit and finding wholeness as a person and then as a leader, was that traditional workplaces still don’t value emotion, vulnerability, or wholeness.

How many bosses have you had that are friendly, cordial, and yet, so so distant?

Sometimes it really does take a room full of women nodding along to the idea that you’re allowed to bring your whole self to work for it to clickthat you haven’t been doing that, at all. And a room of men would rarely be discussing that so wholeheartedly and openly — which is an issue in itself.

When you operate from the (entrepreneurial feminist) belief that there are enough opportunities, jobs, and places for all of us at the table, you feel comfortable bringing your whole self to work. This is part of what didn’t suit me in the traditional workplace, but I still find myself censoring myself with clients and colleagues.

WHAT I LEARNED: When I operate from a place of wholeness and empathy, I connect with the best people: in business, in friendship, and in love.

Because I’m looking at people as humans instead of transactions or companies. I’m allowed to care about them, inquire about them, and have their best interests in mind.

I’m allowed to function like a human first. And so are you.

#2: Your curiosity + grit is your differentiator

REALITY: Too many entrepreneurs give up when we’re told “NO”.

I obsessively listen to How I Built This — and the episode about Spanx with Sara Blakely is a perfect example of how curiosity, grit, and determination (and seeing a gap in the market for something that doesn’t exist yet) is plenty to base a business on.

Sara spent years selling fax machines door-to-door with her underwear lines showing through her pants. Nobody liked it, but nobody did anything about it, either. (Hint: the people making tights were all men.) So, she just cut the feet off her tights and wore them under her cream-colored pants. And then (several years and hundreds of hours later) BAM! Spanx.

It was her creativity and courage that got her national distribution at Neiman Marcus. She asked one of the female buyers to come with her to the bathroom during her pitch to see how her product really worked — and that little experiential touch got her the leg in the door (pun fully intended) that she needed.

MOMENT OF CLARITY: Her curiosity unveiled an opportunity for her, and she kept going until she got a “YES”.

She cold called retailers asking for meetings. She found producers. She wrote her own patent and got her mom to illustrate it. She showed up. Even when everyone told her over and over again, “no,” and “that’s ridiculous” and “that’s never been done”.

She got creative with new ways to get her product out to the world. On the shopping channel. By physically moving it around the department stores. By getting her friends to buy them (to show demand.) And, by sending a pair to Oprah (who then named it the product of the year).

So don’t squash your ideas before you test them. If you believe they fit the market, you have to be curious and open to exploring how to launch and familiarize people with your brand.

Starting a business requires courage — because you know it could fail, but you believe that it won’t.

“I believe that what we regret most are our failures of courage, whether it’s the courage to be kinder, to show up, to say how we feel, to set boundaries, to be good to ourselves. For that reason, regret can be the birthplace of empathy.

― Brené Brown, Rising Strong

WHAT I LEARNED: You have to be ready to be the only person that really believes in this thing that you’re building.

#3: Your gut > other people’s ‘knowledge’

REALITY: Business is always a calculated risk you take or leave.

And, if you’re an entrepreneur or small business, you are the CEO, CFO, CMO, and COO. And most times during the beginning?

You don’t know what end is up.

When you go searching for advice, you cry a little. Because it is everywhere. In all languages. From all angles. Except the expert, custom insight you need at this exact moment in time.

MOMENT OF CLARITY: You are the only person who’s going to have to live with your decisions.

You can hire professionals. You can involve partners and agencies. But after learning what you can, you have to make the decision, and trust it enough to see it through.

This is where “not being the smartest person in the room” helps, and so does swallowing a big pill-o-humility. Because even though you are all the things?Doesn’t mean you know all the things.

And honestly, you shouldn’t.

There’s a certain time where you can go without professional bookkeeping or design, but there’s also a time to suck it up and pay the g’ddamn professionals.

My friend and inspiration, “brand therapist” Ange Friesen of On Wonder once told me to “trust the universe” but also my gut. Because there’s only a certain amount of reading. Only a certain amount of prep. Only a certain amount of information that’ll fit inside that gorgeous, capable head of yours.

Until you have to trust your gut and make the leap, one way or the other!

WHAT I LEARNED: Trust the universe (and sometimes, the universe is you.)

#4: You’re allowed to charge $ for fixing problems

REALITY: Businesses fix problems. It’s not a “favor.” They do it for money. And it’s ok.

I attended a SheEO and City of Toronto Women’s Business Conference in March 2018 (there were 500 women in the City Council Chambers… it was an exciting day), and I heard Huda Idrees of Dot Health talk about how she came up with the idea for her company.

She was a product engineer and designer at Wattpad, Wave, and Wealthsimple, and therefore a veteran in the Toronto startup community. So what gave her the idea for Dot Health — an app that syncs, keeps, and allows you to carry all your health records with you, without depending on faxing them to every doctor’s office you visit?

The fact that it simply didn’t exist, and… that was dumb. That in 2018, we hadn’t solved the problem of having to fax or carry huge binders of crucial, handwritten health information with you to every doctor’s appointment.

She wanted to give control to the consumer over their own health information, with security, with confidence, and without faxing. Seriously — who faxes anymore? How is that still a thing in 2018?

MOMENT OF CLARITY: Your ideas about money could be preventing you from solving people’s real problems.

Another event gave me a chance to listen to Julie Cole of Mabel’s Labels, who said “We didn’t come up with something revolutionary [with Mabel’s Labels]. We just didn’t see something in the market that we, as moms, needed. So we created it.

She continues, “All you really need to make a business is to either a) make something that doesn’t exist, which is the harder of two options, or b) improve or make prettier/more functional something that already does”.

Seems pretty simple when she puts it that way, doesn’t it?

WHAT I LEARNED: Don’t bring your passed-down money ideas into your business or let anyone shame you for making a living by creating something that didn’t exist (or doing it better).

#5: You never have more time than you do right now

REALITY: “I’ll do it later,” means never.

Joanna Wiebe, the creator of CopyHackers and the guiding light for the THING I WAS ALWAYS MISSING in the in-house marketing departments, created the term “conversion copywriting” because it literally did not exist.

Who does that?

Oh yes. People who aren’t scared to make a change and influence an industry.

People who believe in what they’re creating.

And people who put in the hella hard work that is required in order to birth something strange and beautiful into the world. (Shout-out to my mom.)

In one of my courses with Joanna, she said “You’ll never have more time than you do right now.”

Which is a rephrase of a saying my basic self should probably tattoo on a calf or something…

MOMENT OF CLARITY: “You have the same 24 hours in a day as Beyoncé.”

Sure, Beyoncé has a horde of employees, fairies, and goddesses surrounding her at all hours of the day and night. BUT.

You won’t have more time “later”. You won’t be more ready “later”. You won’t really be more prepared “later”.

If you’re not preparing now, you’re not preparing at all.

WHAT I LEARNED: Just f*cking do it. On the weekends. In the evening. If you have an idea — go for it.

So I did.