Megan Hess is one of the world’s most well-known fashion illustrators, having illustrated portraits for the New York Times, Italian Vogue, Vanity Fair, Prada, Cartier, Dior and FENDI. Not only is Megan a talented artist, but she has also written and illustrated seven best-selling books, is a mum, an artist in residence to multiple international venues and has built a global business. She is a leader who inspires!

Megan was kind enough to share her experiences in starting a business and her reflections on being a leader.

Megan Hess Drawing

How did you land your first client? Were they in fashion?

I studied Graphic Design because it felt like a ‘real’ job in the art world, but I really always wanted to be an illustrator. I just never knew that it was a possible career choice! After working as an Art Director in Ad agencies for several years, I packed everything up and moved to London. It was in London that I worked in a million different creative jobs and my final job there realised that I had a burning desire to be an artist.

At this time, I was the Art Director for Liberty Department Store. While I loved art-directing fashion, I loved illustrating it more. I started to do very small illustrations for Liberty and from this other art directors saw my work and little commissions began to follow. After about a year I found myself with non-stop work. I wasn’t earning a fortune, but I’d never been happier, and I knew I was going to do this forever.

As my clients got bigger and better, I was able to be a little more selective, and just work on briefs that I knew had a great creative opportunity. Then in 2006, I got a call in the middle of the night from Candace Bushnell’s publisher asking if I would illustrate her next novel ‘One Fifth Avenue’. This was when things took off at rapid speed for me. Her book became a New York Times bestseller, and I met with Candace, and she asked me to illustrate all her previous books including the cover of ‘Sex and The City’. Once ‘Sex and the City’ was released I was contacted by TIME magazine in New York to create portraits for them.

Following this, I began illustrating for Tiffany & Co, Chanel, Dior, Cartier, Vanity Fair, Italian Vogue, Bergdorf Goodman and Ladure. Ironically, at the same time as my work finally took off, I had my first baby!! It’s funny, I always tell people that I haven’t really slept since 2006!!


What was it like to go from working on your own to hiring staff and having to be the leader in your team?

At first, I was terrified of hiring staff because I had worked on my own for so long. But as soon as I had my first employee, I realised I should have hired someone years ago! My business dramatically grew, and I was suddenly able to get back to focusing on creating. It was the best business decision I ever made.


What do you look for in an employee about to join the Megan Hess team?

I always start with personality. I believe if someone has a great personality and is intelligent, they have the capability to do anything. My team is small, so it’s important that everyone gets along and respects one another.

It’s very important to me that everyone feels safe and loved. Even though it’s work, we all spend a lot of time together so everyone feeling good is so important. I’m so proud to say I work within a group of women that feel like family. I’m very lucky.


What achievement are you most proud of?

Getting paid to do what I love for a living and being a Mother. I see that as a huge luxury to be able to do both, and it’s something that I’m very grateful for every day. I’ve also been able to donate many pieces of my work for charities and causes all over the world, and in some small way, I feel proud that one of my drawings may have helped someone where.

As Creative Patron of Ovarian Cancer, I’ve also had the privilege of working with the most inspiring team of people trying to raise awareness and funds for the development of an early detection test for Ovarian Cancer.

Megan Hess Book

As your career has grown, you’ve worked with some incredible brands. How did you first initiate these client relationships?

I am very grateful to all the amazing brands that I have worked with. For me, it’s been years of building those relationships. Each new project attracts a new client, and I have been fortunate to have been commissioned by such diverse and creative companies all over the world.


What areas of leadership are you most confident in and are there aspects of it that you struggle with?

I’m a big picture person. I don’t like to micromanage. I’ve always believed in the theory that it is best to work with people who are faster, smarter and much better at certain things than me. I know my strengths, and I love to let my team manage and take ownership of their roles. I’ve learnt that autonomy is very important for people to grow and for a company to grow.

Megan Hess Desk

How do you find owning your own business and being a mum? Does your home, office etc always look as good as on Instagram?

Ha! Well, sadly no although I wish it did. Actually, my studio always looks pretty good because we all make an effort to keep it ready for both chic clients who drop by and last-minute photoshoots. My home is sometimes completely tidy and lovely, and other weeks I have piles of washing, dishes and school projects everywhere!! It’s a normal household full of lovely chaos!


You have such a diverse business including prints, commissions, books, homewares/styling and more. Can you describe your creative process?

I hand draw all my line work with a custom Montblanc pen and ink, then I either leave it black and white or add colour with gouache, watercolour and digital means. Some of my illustrations are very fast. I usually post a quick sketch on my Instagram account each morning (@meganhess_official) and I only ever give myself 10 minutes for that – because I have so many deadlines to get through! Most of my work can take anywhere from an hour to several days. It just depends on the complexity of the illustration.

If it’s for a client, it starts with a brief, and I always give myself a good amount of initial time to dream and get inspired about what I’m going to draw. Sometimes I’ll do initial sketches or create a mood board of concepts and ideas. Then I’ll discuss with my clients where my direction is heading. Then it’s to the physical drawing phase, and I’m usually in absolute joy creating the final image.

See the magical work of Megan Hess.


Anastasia BenvenisteAbout the author
Anastasia Benveniste loves anything digital or creative and is passionate about human rights. She gets enormous amounts of personal satisfaction through her work in digital communications, as it allows her to share people’s stories. She has a Masters in Design Communication, and her favourite academic experience was spending a semester studying at Yale University. Outside of work, she loves art history, painting and anything monogrammed!

While the media has recently focused on groundbreaking women like Hillary Clinton and Sheryl Sandberg, and their efforts to promote feminism in modern society, they actually follow in the footsteps of a long line of influential women. While there are numerous women throughout history that have challenged norms and stood up to societal pressure, we can’t possibly cover them all. Here are 8 women who broke the mold decades—sometimes even centuries—before their time.

Maria Theresa of Austria (1717-1780)

Maria Theresa

In 1740, Maria Theresa inherited the rule of a country that was penniless and poorly governed. Though her father had ensured her succession, he had not educated her on matters of the state. She eventually chose her own advisors and deftly delegated responsibilities. She turned around the economy, revitalized the military, and instituted mandatory public education for both boys and girls in the country. She held onto her rule amidst 2 wars, and managed all this while still giving birth to 16 children.

Mary Wollstonecraft (1759-1797)

Mary Wollstonecraft

Perhaps best known for her work, A Vindication of the Rights of Woman (1792), Mary Wollstonecraft was anything but a traditional young English woman. She became an intellectual and a writer, and believed strongly that women should be educated as men. She took lovers and had a child out of wedlock when such things were scandalous, and her reputation was tarnished for decades. However, it is believed that her works strongly influenced writers like Jane Austin, and during the women’s suffrage movement of the late 1800’s her writings, particularly her ideas about educating women, became the backbone of the feminist movement.

Queen Victoria (1819-1901)

Queen Victoria

Queen Victoria inherited the throne at the age of 18, and was the longest ruling monarch in British history, until her granddaughter surpassed her record in 2015. She presided over one of the largest empires the world has ever known, and was beloved both in England and in many of the British Colonies. She managed to maintain her rule and continue to build the modern constitutional monarchy while remaining largely independent of party politics.

Coco Chanel (1883-1971)

Coco Chanel

While a fashion icon may seem to be a trivial representation of a great female leader, Coco Chanel was remarkable in her forward thinking and indifference to societal expectations. Choosing to wear trousers and “men’s” clothing, she released women from corsets and other encumbering clothing, focusing on casual comfort instead, and revolutionizing women’ She challenged society on social level as well, choosing never to marry or have children, while publicly embracing intimate relationships with men on her own terms.

Eleanor Roosevelt (1884-1962)

Eleanor Roosevelt

Eleanor Roosevelt began her influential career when she was in her teens, becoming active in social work, before meeting her future husband. She was an early advocate of civil rights, and as First Lady of the United States, was independent and outspoken on the rights of women and African-American’s, long before the onset of the Civil Rights movement. She wrote a daily newspaper column that reached vast people, in which she defended women’s rights and other humanitarian causes. After her husband’s death, she continued working as a delegate to the UN, where she advocated for people, taking a non-partisan stance on most issues. She fought all her struggles, whether personal or political, with honesty and straightforwardness.

Indira Ghandi (1917-1984)

Indira Ghandi

Though she is a controversial figure, Indira Ghandi is a stunning example of a woman who managed to gain power in a time and place where women were generally treated badly. Groomed for the position by her father, she became the first, and only, female prime minister of India. She took a very troubled country in dire straits and turned around the government and the economy. She was also a strong advocate for women’s rights, and helped to advance India on the international stage. Unfortunately, she was assassinated by two of her own bodyguards in 1984, in response to an attack on a Sikh temple by Indian forces while trying to remove a political opponent.

Ruth Bader Ginsberg (1933-)

Ruth Bader Ginsberg

Still going strong, Ruth Bader Ginsberg remains one of the most influential women in modern history. Being one of the first women ever to enroll at Harvard Law School, she had a prestigious academic career before she went on to argue cases for women’s rights that have helped to try and level the playing field for women. She has fought against gender discrimination every step of the way, and continues to do so from her esteemed seat on the United States Supreme Court.

Oprah Winfrey (1954-)

Oprah Winfrey

With the longest running daytime talk show on television, broadcast in 145 countries around the world, it’s easy to recount the leadership of this incredible woman. Beginning her life in poverty, she went on to become the single wealthiest African-American, and has in turn dedicated herself to trying to lift others out of poverty as well. She established the Oprah Winfrey Leadership Academy for Girls, and invested over $40 million of her own money in the project.

These great women paved the way for the modern feminist movement, and the changes that they managed to bring about have altered the course of history for all women. The one thing they all seem to have in common is refusing to stay in a box that society tried to put them in. Take a lesson from them and learn not to take “no” for an answer.


Corinne Ledling is a businesswoman who’s very passionate about her job. She’s a Content Manager at and loves to share career tips and tricks.

For too long, self-care has been a boys’ club. While golf time, “bro” time, and man-cave hours are considered perfectly acceptable ways for men to relax after a hard day, women are sometimes left in the dark.

We don’t necessarily receive the same sort of automatically assumed “time away” to relax, refuel, and care for ourselves. Come 5 p.m., many women make dinner, take care of the household, or keep working ’til they drop in order to prove themselves.

Let’s face it, ladies: It’s time we think more seriously about how we love ourselves. Taking care of ourselves first will help us not only feel better, but — excitingly — nurture our highest potential as well. Here’s how I found my self-grateful groove:

The Power of Self-Love

My journey to taking better care of myself came during my college days, and it’s since proven to be one of the most powerful propellants of my career. As a young woman who started a company while studying to be an engineer, I knew my path wouldn’t be easy.

And after long days of taking classes, seeking internships, responding to requests for proposals, and trying to talk friends into joining my company, I was worn out. But I refused to let myself pause; I kept pushing myself to be more, do better, and sleep less. It was a vicious cycle, and at 26, I had developed a nodule on my vocal cords and various painful health issues.

After years of desperately trying to take my business to the next level, I knew something had to change. I was running my body into the ground, and I was stumped on how to escape the dark place in which I had found myself.

Self-Care Gets a Bad Rap

Self-love is often looked down upon in the business world as unnecessary at best and lazy at worst, but my medical problems made me realize I needed to practice it to get my life back. Unfortunately, the problem is deeply institutionalised, and many women are hesitant to prioritise themselves, just as I was. With women still making only 74 cents to the dollar, we’re well behind men, and we feel the need to take on more work for less pay to prove ourselves.

In the month after I realized I needed to work less and take care of myself more, I began making changes. I hired a life and leadership coach, and I started reconnecting with the friends I’d lost while driving myself into the ground. I started eating healthy again, forgoing the fast food I’d become dependent on because I didn’t make time for meal prep. I affirmed myself in writing, forcing myself to reflect on the person I wanted to be and the person I had become.

Slowly, over the course of the next four years, I created a new me: I went from being depleted, tired, overwhelmed, anxious, and stressed to overflowing with gratitude, joy, and love.

The Three Tenets of Self-Care

The bottom line is that you must first take care of yourself before you can care for others. Here’s how I learned to put myself first and care for my body and mind:

  1. Treat yourself like your most beloved partner.

A scene in The Mindy Project, in which Mindy is struggling to appreciate her pregnant body perfectly exemplifies this. Feeling downtrodden and desperate to make peace with herself, she hires a stylist, who asks Mindy to look in the mirror and describe what she sees. Mindy is ruthless, self-deprecating, and eager to point out her flaws, but the stylist interrupts her and says, “What if this were your best friend? Would you say those harsh things about your best friend?” Mindy’s stylist brashly tells her to look back in the mirror and speak to herself as she would to her own best friend.

Unfortunately, this is how too many of us think about ourselves. We might not say it out loud, but we constantly pick on our own flaws and imperfections. It’s not healthy, and it’s not the road to self-care.

Instead, look yourself the mirror and describe five things you like about yourself. Try this each morning, thinking about how you’d talk to the person you love most. How would you help her feel ready to face the day? How would you help her feel confident, loved, and cared for? Use that same language with yourself, you’ll be astonished at how you begin making time for your needs and your own happiness.

  1. Listen to your body.

My father was a big believer in the value of listening to your body. When I was young, he reminded me time and time again, “Your body knows what it needs, and your body will tell you when it needs it.”

This concept is foreign in our society, and I’d never heard it from anyone else until I visited India and realised it’s a common way of speaking where my father grew up. Here in the U.S., we are taught to listen to magazines, celebrities, calorie counters, fitness trackers; we are told to ignore our bodies and look elsewhere.

Start listening to your body: Feel the sensations in your gut, your heart, and your head. Let your natural signals guide your diet, sleep, and daily habits. When you listen to your body, you eat more healthily, sleep better, take time to relax each night, and create a more fulfilling life for yourself.

  1. Don’t live your life based on others’ expectations.

Many of us feel the pressure to partake in certain activities because we’re told we should. For example, I’ve been told to practice yoga to calm and center the mind. There’s just one problem: I don’t enjoy yoga, and my body doesn’t call out for it.

Instead, I participate in an Olympic weightlifting club through my gym. Maybe some don’t consider it a “woman’s exercise,” but that doesn’t matter to me: The charge I get through my central nervous system refuels my tanks and centers my mind more than yoga ever has. Enjoy whatever activity feels good to you — not whatever the latest trend in self-care happens to be.

The key is to make ‘you-first activities’ a high priority. As a leader, you don’t have the luxury of putting yourself on the back burner. It’s vital to the success of your company that you are on top of your game at all times. My gym time, meditation practice, my phone calls with my grandma — these activities are the first tasks on my calendar, and they don’t budge for any reason.

As a female business leader, you’re already extraordinary and deserve your own best care. Women might be 50 percent of the population, but we hold just 14.2 percent of the top leadership positions in S&P 500 companies.

Love yourself like the strong, successful woman you are: You deserve it.


Sumi Krishnan is a serial entrepreneur, singer/songwriter, barbell enthusiast, and founder of She is passionate about helping other badass leaders on a mission live lives of holistic success while embracing their most meaningful impact.

A Leader in Heels is a self-starter. Someone who dares to dream, and creates her own opportunities.

Jessica Wilson, founder of the fashion app Stashd, is a true example of a Leader in Heels. After being told by a careers counselor that she couldn’t make it in the cutthroat fashion industry, Jessica did more than prove her doubters wrong.

After a successful stint in fashion working in Australia and New York, Jessica was drawn to Silicon Valley to learn more about the tech industry. With her trademark determination, she wanted to learn how she could use her fashion industry knowledge to create her own space in an entirely different (and competitive!) industry.

Stashd is a “fashion discovery app”, which helps you discover and buy your next favourite piece. The app presents a single item at a time: if you love it simply swipe right to “Stash” it into your virtual wardrobe, or if its not for you, swipe left to “Trash” it. Your virtual wardrobe can be shared with friends, and also helps you purchase your favourite pieces directly from the store!

So how did this Gen Y leader go from a career in fashion to being a tech co-founder? Jessica chatted with Leaders in Heels to share her five tips on creating your dream company from scratch.

1. Look for ways to make your own experience

Jessica’s entrepreneurial drive was evident in her teens. After being told that her high school wasn’t having a formal after-party, at the age of 16 Jessica learned that “when someone says you can’t do something, it doesn’t actually mean that you can’t do it”.

Jessica took matters into her own hands and negotiated with her parents to have the party on their farm. This experience, from learning how to negotiate with her parents, DJs and suppliers, through to running events attended by more than 400 people, gave Jessica important leadership skills and the understanding that you can make your own opportunities out of nothing.

2. Take set-backs in your stride and always follow your gut

After her success in running events, Jessica was more than ready to take the next step into fashion. After researching a lot of schools, she found what she thought was “the best of the best”. However, things didn’t turn out as planned when she was told that she didn’t have what it takes to have a career in fashion.

There’s no doubt that this was a really difficult time for Jessica. After a period of self-reflection, she knew that it was time to leave.

“I decided to not take their perception of me to heart. They didn’t know me, and they had only met me for a few minutes. It was a matter of backing myself, trusting myself and hoping it would all turn out. They weren’t supporting me and what I wanted to do, so I had to leave.”

For Jessica, this was another important lesson early in her journey: trust your gut and never settle for second best.

3. Throw yourself outside your comfort zone

After the early set back, Jessica’s determination landed her a job doing seating charts for well-known designers such as Akira Isogawa and Bettina Liano. This was a huge learning curve, and it wasn’t long before Jessica was off to New York, producing shows for Australian designers before working with industry heavy weight Kelly Cutrone at People’s Revolution.

At this time, Jessica noticed “dots in the industry that started to connect”. After deciding she wanted to learn more about the tech industry, she immediately headed to Silicon Valley. At 21 years old, Jessica threw herself out of her comfort zone and spent a week heading to different events, meeting people from Google and Yahoo, who heard about her journey and took her around tech giants such as Google, Facebook, Yahoo and Apple. After learning everything she could in a week, Jessica knew that fashion technology is exactly where she wanted to be.

4. Look for people with skills that compliment yours

One of Jessica’s greatest skills is throwing herself into meeting and learning from people with the complimentary skills to her own. After returning from Silicon Valley, Jessica went straight to a tech co-working space, and surrounded herself with the people that had the skills she needed to create Stashd.

“If you have a genuine connection with someone, it will open more doors. You need to just put yourself out there”

5. Beware of “founders’ bipolar”

Jessica admits that life as a founder is not just the perks you see in the media. After living and breathing Stashd, she recognised the importance of looking after herself to ensure that she can make it through the good and bad times.

“You need to learn how to manage your state, how you are going to take on all of these challenges and how you will cope mentally.”

These days Jessica uses meditation to help stay grounded, and get her through the busy days and often long hours involved creating a game-changing app.


Thank you to Jessica for taking the time to chat and share her advice with Leaders in Heels. After a huge few months, which have included being the youngest Australian woman ever invited to attend the Forbes Under 30 Summit, and heading to Antarctica with a group of fellow entrepreneurs, we can’t wait to see what’s next for Jessica and her tech dream.

At Leaders in Heels, we love nothing more than interviewing inspiring women who are willing to share their passion, knowledge and expertise with our readers. With two businesses, a degree, a national franchise network and two children under her belt by the age of 30, we can all agree that Tina Tower has plenty to share!

Tina credits her achievements to a massive desire to achieve and live a life less ordinary. After seeing her father sick with cancer at a young age, Tina is acutely aware that life is short, and strongly urges everyone to make it count and do something great with their life.

Feeling inspired? So are we!

After working a few jobs to pay her way through Uni, Tina opened her first business, Reach Education Centre in November 2004 when she was 24 years old. She admits wondering: how hard can it be?! Two years later, Tina graduated and threw herself into the business. Tina admits that the business was big, laborious and badly leveraged!

With her trademark grit and determination, Tina preserved with the business – selling toys, tutoring and running birthday parties and arts and craft sessions. It wasn’t until a large toyshop opened down the street that everything turned sour. The owner of the toyshop called Tina prior to opening, telling her to close her doors now, before they put her out of business. Reach lasted two years after this before closing down.

Luckily for Tina, bigger and better things were in store. At the Centre, she had developed Begin Bright, a program to help build children’s reading ability and confidence. She had the idea to do school readiness courses, something that hadn’t previously been done in Australia. Soon the course licensed at 50 locations across Australia.

Like many businesses, growth presented a range of challenges for Tina. Under the license, Tina wasn’t able to give business advice – which was a challenge with her experience in the tutoring industry. Licensees also couldn’t use the Begin Bright name.

We looked at either accepting that people would do what they want, and we would have to bite our tongues… or we would have to franchise.

Tina admits that franchising is tough! But with her goal to have thousands of students around Australia completing the program, it was the only way to build the business properly.

I was really close to walking away. I was doing everything by myself for the first two years; it is only in the last 18 months where I started to get help.

Thinking of franchising? Tina recommends:

  • Filling the gaps in your own knowledge with a board of advisers: Whilst Tina likes to think that what she lacks in experience she makes up for in general enthusiasm, she strongly recommends building a board of trusted advisers. Tina’s board members have all been in franchising for around 20 years and she admits: there is no replacement for knowledge that comes over time!
  • Using a business planner to help break down your goals. Begin Bright has five-year plans, right down to weekly action items. “It is not so much a pie in the sky dream these days – we are taking tangible action steps which will actually get us to where we want to be.”
  • Surrounding yourself with the right people. Starting a business can be lonely; people always see the glamorous parts but often miss the hard work and challenges. Make sure you have people around you to build you back up.

What about Tina’s advice for other women who are starting a family and a business?

Tina admits that she has never known any other way, having only ever been self-employed! After having her two boys, Tina strapped them in the sling and took them back to work!

When it is your own business, you are in the drivers seat. You are in charge of your own life. Gone are the days where you have to choose family or work; I have my dog next to me at the office, my kids have a desk at the office for their important work, whenever there is a school assembly or play I’m there. I know you can’t always do this in a conventional job, but with your own business you are building something for your family.

Tina’s final piece of advice? “Go and do it!”

In 2012, Leaders in Heels interviewed Kate Morris, the founder of Adore Beauty, who shared what she had learned starting her own business.

Two and a half years later, Adore Beauty has tripled its revenue to a turnover of more than $7 million. Now the leading Australian beauty website, Kate has the big international beauty retailers firmly in her sight.

A true cosmetics junkie, Kate’s passion for growing Adore Beauty is immediately apparent. After seeing Adore Beauty’s growth in the last three years, the next question for Kate is: if we can do this, what else can we do?

Are you embarking on the next stage of your business? Kate has shared her tips with Leaders in Heels to help you take your business to the next level:

Keep innovating

For Kate, it’s critical that Adore Beauty is at the cutting edge of retail innovation – which means accepting that the team has to have the courage to fail.

“You see this with a lot of new companies, they try a new thing once and when it doesn’t work they just stop. Of course, you can’t stop”

When something doesn’t go right or doesn’t work the way you had planned, ask yourself: what have I learned from this? Re-engineer the experiment to see how you can give it another go. Do you chuck it out, change it, or try again? The one key lesson that Kate has learned is to just keep going!

Focus on your culture

Working out your company’s values is key to guiding your strategy and decision-making. In Kate’s experience, life as a business owner will often present you with two paths that both seem okay. Resolve these challenges by having a clear picture in your mind about where you want the business to be in 10 years time. Kate recommends taking time out of the business to work out what values are important to you. What will make the business better? What will make it a place where your staff wants to work? What will make it a place that you want to work? What will make your customers come back?

Don’t be distracted by your competitors

While it is great to keep an eye on the landscape and reviewing the environment that you are doing business in, don’t fall into the trap of focusing on everyone else. Keep focused on how your business relates to your customers and your goals. What value are you driving?

Make sure everything is scalable

Can you get your goods out the door and maintain your customer experience? Make sure you plan to grow at a speed that grows and maintains your customer base.

Focus on your transition from founder to CEO

Be strict with yourself! You need to set up systems and start delegating to take your business forward.

You have to get past the stage where you think ‘oh, this is easy, I’ll just do it!’ – there comes a point where this attitude holds the business back”

Kate has seen her role change over the last couple of years, and now looks to the key areas of her business where she can add significant value. As a CEO, she recommends hiring, supporting and trusting your staff to do their job, to help you focus on achieving your business goals. Kate also notes that there is a temptation to shy away from critically reviewing yourself and your performance: it is okay not to be good at everything! What is important is identifying your strengths and weaknesses, and considering training or mentoring if you need extra support.

Invest in your systems

Don’t shy away from difficulties updating your systems to the required level to support your growth. While Kate admits that replacing Adore Beauty’s entire ERP system while the business was moving presented a big challenge, it’s critical that your systems can support your growth.

So what’s next for Kate? From a rapidly expanding brand portfolio to spreading the word on Adore Beauty, we can’t wait to see what is in store for this inspiring entrepreneur.

Kate’s final piece of advice for Leaders in Heels readers: While growth is an exciting time for any business, don’t lose your head!