What May Samali’s journey can teach you about building your dream life through courage, hard work and introspection

February 14, 2022
May Samali
May Samali


If you google ‘May Samali’, you’ll be instantly blown away by what is the picture of a highly accomplished woman. A lawyer by training, a Harvard University alumna, a venture capitalist and the Founder and CEO of Coaching by May, she is a role model to thousands of people across the globe. 

It is easy to look at all of May’s professional achievements and attribute them to talent, luck or a great life plan. However, what is not immediately obvious is the years of consistent hard work, effort in the face of  fear, failure and honest introspection that has helped May get to where she is today.

If you’re curious about what it takes to create a fulfilling and purposeful life that aligns with your values, read on. 


Following your fascinations 

As a child, May felt a sense of social responsibility to make the most of the opportunities afforded to her in Australia. As a Persian Baha’i, she was acutely aware of the privileges she had access to growing up in Australia as compared to her parent’s homeland of Iran. 

“When I was 12 I decided that I wanted to be an international human rights lawyer. I was deeply passionate about solving big issues, such as genocide and the refugee crisis, and the way I wanted to do so was by giving people a voice. I wanted to ensure individuals and groups could access justice in order to live their best lives,” she tells me. 

When she finished high school, May ventured to law school. She felt that becoming a lawyer would allow her to empower the most marginalised and disadvantaged members of the community. Her studies took her to New York, the hub of international law, where she was serendipitously exposed to the world of social entrepreneurship and innovation, and the idea that we can solve big, hairy problems using business models and technology. She was instantly fascinated. Hooked, even. 

“As a junior lawyer, I had the privilege of working with incredibly inspiring leaders including Her Excellency the Honourable Margaret Beazley AC QC. But I still had days in the courtroom where I would look around and realise that I didn’t want this,” she says. 

“I was longing for more creativity and felt a calling towards the world of startups and entrepreneurship. This is where I felt most alive. 

“This realisation was a pivotal point that led me to graduate school, where I focused on how I could best support entrepreneurs to build solutions to the most pressing challenges of our time.” 


May with her parents at the John Monash Scholarship Presentation ceremony in Melbourne.

Making courageous pivots 

After graduate school, and during her days as a venture capitalist and startup entrepreneur, May constantly found herself gravitating towards helping her founders and team members grow their personal and professional leadership skills. She felt most fulfilled when she was creating space for these individuals to explore their values and drivers and gain a deeper awareness of their vision for their careers and lives.  

“I noticed it doesn't matter how well your startup is doing if you don’t understand why you’re there and what your broader purpose is,” May says.

“I found that I really loved helping people know themselves, build their mental fitness, and achieve their full potential. I believe my purpose is to inspire a world where we can each live our purpose with courage, confidence and conviction.”

Making these pivots meant uphauling a lot of her life — moving cities and countries, ending relationships and quitting various jobs she had worked in for years. However, May found that the more she pivoted, the easier it became to be open to the next shifts that came her way.  

“I now trust that it is okay to not know exactly what is next. I have historical evidence that the most important factor is to be attuned to what feels right in this moment. If it feels right, it is right, for now,” she reflects.   

Looking back at her journey, May feels that the thread that connects each of the professional hats she has worn — lawyer, advisor, investor, facilitator, coach — is working with people to unleash their power, purpose and potential. Her journey has been focused on getting closer and closer to the centre of her ikigai, the force that gives her life meaning. 

May explains: “Often we conflate our various roles with our identity. But they are not the same thing. Once I understood that I was not my title, my job, my relationship, or my achievements, I was free to try new things. I realised that if I tried something new and it didn’t work out, it wasn’t because I was a ‘failure’. It just meant that the thing didn’t work out.” 

May acknowledges that she still has her moments of feeling doubt and fear when considering a pivot. The way she now deals with these challenges is by asking herself why a pivot feels hard. 

“You have to ask yourself if something is the ‘right’ kind of hard. Moving across the world to study your dream program is the right kind of hard if it brings you closer to your personal or professional purpose. But if something feels hard because you’re doing it to please people, meet social expectations or gain familial approval, then that’s probably the wrong kind of hard,” she explains. 

“Once you identify things that are the right kind of hard, it is easier to feel the fear and make the pivot. To quote Susan David, ‘courage is not the absence of fear, but fear walking’.” 

May teaching and coaching student entrepreneurs at the Nalukai Summer Startup Camp in Hawaii. 

Leading with values and curious introspection

May describes her values as anchors that help her determine if a decision is right or wrong. They empower her to lead with certainty while keeping her grounded through chaos. 

“My three core values are authenticity, connection and growth,” May says. 

James Clear said: ‘You don’t rise to the level of your goals. You fall to the level of your systems.’ Putting this wisdom into action for me means reflecting every week on whether I honoured my values through my actions. Every quarter or so I take time out for introspection and ask myself if these specific values are still serving me. 

“It is fun to see them change, because watching myself grow and transform reminds me that the individuals I work with are constantly growing and transforming too,” May elaborates. 

As a certified coach and facilitator, May has helped dozens of individuals and teams identify their core values and build businesses, careers and lives that align closely with these values. 

As part of the Spring ’21 Startmate Women’s Fellowship, I attended a ‘Design Your Life’ session led by May and left feeling more aligned and clear-headed than I had in a long time. Many of my co-Fellows felt the same way and we were converted into May Stans. 

What stands out about May is that she is deeply human. She accepts that she will never be done learning or growing. Practising habit 7 from Stephen Covey’s 7 Habits of Highly Effective People, she ‘sharpens the saw’ by receiving coaching, training and therapy herself. This is but another example of her integrity: she practices what she preaches.

May’s values also determine how she shows up in her daily interactions and in her business. They’re the ‘non-negotiables’ that help her live a purposeful life. 

“My values help me bring an integrated, whole version of myself to every conversation and interaction. What I do and how I show up is an extension of who I am,” she explains.

“For example, authenticity means that I speak my truths, share my experiences, and live as my true messy self. Whether I am talking to a client or to my family, you will only see one version of May. This can feel terrifying but also deeply empowering. My values also influence who I work with because only when I am true to my values can I help other people stay true to theirs and be their authentic selves with me.” 


May leading a ‘Design your Life’ workshop for Startmate's Women Fellows.


Living with purpose

When asked what advice she had for people looking to live their dream lives and with purpose, May shares three gems that I want to include in their entirety. 

“The first is to start within. You get to decide what you define as your ‘dream’ or what ‘success’ means to you. Work from the inside-out. In defining what you want for your life, realise that all parts of life are interconnected. Focus on integration across the various aspects of your life, rather than setting up the various parts of your life to be in competition with each other.  

“The second is to be okay with living in the ‘in-between’. You don’t have to define yourself as either ‘this or that’. Instead, embrace the paradoxes of life — embrace opposing perspectives and seeming contradictions. When you feel you have to choose between black and white, consider what it might feel like to choose grey. You can be ‘this AND that’. 

“The third is to prioritise. You need to say ‘no’ to some things to be able to say ‘yes’ to what matters most. Decide what your highest priorities are and have the courage to say no to everything else. If it is not a ‘hell yes!’ it is probably a ‘no’.”

May’s journey is a bold reminder of something that we tend to forget: building your dream life is not a matter of luck or external-validation-focused life plans. If you desire greater fulfilment, or want to truly create an impact, the work must first start from within. 

Only when we have the courage to understand, accept and trust ourselves fully and deeply, can we start to make pivots that transform our lives for the better.  

I hope you find inspiration in May’s courageous, incredible and messy journey. I know I did. 

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