Archives For Hope


One thing I have learned is that for the most part, people express the same idea but they express it in many different ways and with many different words. It is the details in the expression, the words, and combination of words used, that give a story its colour, its texture, and brings it–and its lessons–to life.

We are unique combinations of our beliefs, values and life experiences. Differences notwithstanding, we, and our experiences, are important. Therefore, there is value in compiling and sharing these stories and the multitude of ways in which ideas are expressed. Combined, these stories weave a wonderful tapestry that exemplifies just how rich and beautiful life can be.

And who knows? An inadvertent remark or detail in the retelling of a story can stand to attention and have an impact in the world of a reader. And with that exciting possibility, perhaps the most valuable thing I can do is create the space where the stories of those whom I admire and respect can be shared.

Below are people that I have come across on my own life journey whom I deeply admire and respect. Whether it be their tenacity or courage, or relentless drive or passion, each individual generously reveals a different lens in response to the questions I regularly pepper them with.

As we continue on our sharing over this anthology, I will share tidbits and anecdotes as to why I hold them in such high esteem, and what I love most about them. In turn, I hope that you do too.

Is entrepreneurship a lonely journey?

“Is this person willing to make sacrifices for me, and am I willing to make sacrifices for this person?”

Alex Louey. Founder and Managing Director at Appscore. Melbourne, Australia.

Entrepreneurship can be lonely, but it doesn’t have to be! I have been blessed with having a great co-founder that is both supportive, and strong where I am weak, and weak where I am strong.

Finding a good co-founder that you can trust, has high moral standards, and is ethical. The question I asked myself was, “Is this person willing to make sacrifices for me, and am I willing to make sacrifices for this person?” This question is important because a business partner should be there for both the good and the bad.

There are things you can do to make sure you’re not alone

Andrea Grisdale, Founder and CEO at IC Bellagio, Board Member at Entrepreneurs’ Organization. Bellagio, Lake Como.

Becoming part of the Entrepreneurs’ Organization (EO) was one of the best decisions that I have ever made to make sure that I wasn’t alone.

The opportunity to meet personally (or virtually in 2020) with a group of trusted entrepreneurs who run a variety of businesses, to be able to share experiences, and to be able to learn from each other in a safe and trusted environment is second-to-none.

EO has given me so many educational opportunities that have been: (1) worth their weight in gold; and (2) perfect for spending time with people who are “in the same boat”.

The entrepreneurial journey doesn’t need to be lonely

Emma Welsh. Founder at Emma & Tom’s. Melbourne, Australia.

I don’t believe the entrepreneurial journey needs to be lonely. In fact, I believe it to be the opposite.

One of my core aims in business is to build a fantastic team of players that I am constantly surrounded by, and that team needs a captain and a coach.

I find that the fulfillment of both captain and coach roles provides a level of connectedness with my business, and the people in my business.

There is a unique, solitary, and undeniable burden that comes with being an entrepreneur

Jamie Skella. Chief Operating and Product Officer at Mogul, Former Chief Product Officer at Horizon State. Melbourne, Australia.

Entrepreneurship has been a complex journey for me. Although a profound sense of togetherness, support, and connectedness have been part of my journey, there is also a unique, solitary, and undeniable burden that comes with being an entrepreneur; a certain “loneliness”.

Psychologically you will experience pressures that very few others fully grasp, while practically speaking you will have less time for you to spend with your closest friends. That is the choice you make when embarking on such a journey, yet, I posit that it is a sacrifice worth making; a price worth paying, to pursue bold ideas that have the power to create positive change in our world.

“The price of being a sheep is boredom. The price of being a wolf is loneliness. Choose one or the other with great care.” – Hugh MacLeod

The stress amplified to the point that I could no longer laugh

Keith Roberts. Founder, Author and Speaker at OAKJournal, Board Member at Entrepreneurs’ Organization, President at Entrepreneur’s Organization, Founder and Creative Director at Zenman. Denver, Colorado.

The answer depends on the individual, their unique personality, and their approach to business.

Most of my closest friends are people that I met as clients, peers, or through my entrepreneurial journey.

The first 15 years was incredibly isolating. Not only did the struggles of entrepreneurship take away almost all of my free time, the stress I felt amplified to the point that I could no longer laugh.

Finding Entrepreneurs’ Organization (EO), my Forum, a global village of other entrepreneurs changed my life, and having intentionality has to the type of life I want to experience has changed my path from one of loneliness, to one of connection and joy.

If life is lived not by accident but with intention, one can experience a life that is more profound, more intense, more rich, and one can experience a life that is deeply joyous and fulfilling

Kym Huynh. Founder at WeTeachMe, President at Entrepreneurs’ Organization. Melbourne, Australia.

Business, in and of itself, is hard. In a study of 28 million businesses in the US, 96% fail before they reach the $1M/year revenue turnover. Out of the 28 million businesses, 99.6% will fail before they reach the $10M/year revenue turnover. That stark statistic illustrates the tide the entrepreneur wades against in their efforts to create a viable business.

Now let’s layer on the stresses and pressures that come with starting and scaling a business, and the time, relationship, and life sacrifices that is required. At one point in my journey, I had locked myself away in an upstairs bedroom whilst my friends celebrated a birthday downstairs. I recall thinking, “I need to finish onboarding this new customer,” and the feeling of wanting to isolate myself and being alone. When I reflect on this experience, I am not surprised that a common phrase I hear is “entrepreneurship is a lonely journey”.

Now let’s layer on the incredibly steep learning curve that an entrepreneur must endure. For example, every entrepreneur must learn the four key decisions that all high-growth companies have mastered: (1) how do I make sure that there is enough cash in my business? [cash]; (2) how do I make sure that I can drive top-line revenue growth? [strategy]; (3) how do I make sure that I have the right people in the right seats performing the right functions in my “bus”? [people]; and (4) how do I make sure I convert top-line revenue efficiently into bottom-line profit? [execution]

Now let’s layer on the “divergent paths” or “growth divergence” dilemma entrepreneurs experience with friends and family who haven’t lived and breathed what it feels like to be an entrepreneur, and who often give unsolicited advice that is, albeit with good intentions, bad. The emotional energy required to navigate this dilemma is incredibly taxing, and difficult to navigate, for the entrepreneur.

Now let’s layer on the discovery that as the entrepreneur’s life path and experience has diverged from the norm, the entrepreneur starts discovering that conversation and points of interest increasingly diverge. And suddenly there is less to connect with, less in common, and conversations different.

The life of an entrepreneur brings with it multiple demands: (1) physical; (2) mental; (3) psychological; and (4) emotional. All these demands need to be juggled evenly, and at all times. Is it therefore surprising that many find the path of entrepreneurship lonely?

In spite of this, I also believe that we have agency and that if life is lived not by accident but with intention, one can experience a life that is more profound, more intense, more rich, and one can experience a life that is deeply joyous and fulfilling. The entrepreneurial journey was initially lonely for me, but is now filled with deep connections, life-changing friendships, once-in-a-lifetime experiences, lots of laughter, and lots of joy, and of most importance to me, endless opportunity to live a life that is aligned with my life goal of making a lasting and positive contribution to this world.

Lee Munro. CEO at Munro Footwear Group.
Melbourne, Australia.

Like almost everything in life, it doesn’t have to be this way

Many people I talk to find entrepreneurship isolating and lonely. There are constant pressures that an entrepreneur feels: (1) sales; (2) marketing; (3) branding; (4) hiring; (5) firing; (6) culture; (7) values; (8) compliance; (9) finance; and (10) cash flow etc. Ultimately, the success of the business is the responsibility of the entrepreneur.

Some people internalise the myriad of pressures and that alone can make one feel lonely. But like almost everything in life, it doesn’t have to be this way.

Entrepreneurs have options and choice. This road has been well-traveled, and filled with people who are generously willing to share their learnings and experiences.

Some options of note:

  1. Find a mentor who is generously willing to share their learnings and experiences.
  2. Find a networking group of like-minded entrepreneurs.
  3. Share inside one’s own organisation and use the team as support. Brene Brown is a pioneer in the field of “vulnerable leadership” and her research suggests that this leadership methodology is great for both the entrepreneur and the business.

Entrepreneurship can be a lonely journey, but it doesn’t need to be

Namgyal Sherpa. Managing Director at Thamserku. Kathmandu, Nepal.

When I first started my entrepreneurial journey, I was obsessed with the idea of success, and I had a hunger to get things done at any cost even if it meant I had to do the heavy lifting myself. I didn’t trust and didn’t have the confidence to delegate, which consequently left me micromanaging most of the work.

This unhealthy approach lead to burnout, and as I had ignored other aspects of my life that are important to me such as family and care of self, this unhealthy approach also lead to loneliness. Relationships were one of the most important things in life, and it starts with the relationship we have with ourselves.

I started meditating, reflecting, and learning from other like-minded people, and discovered that by having an understanding of who I am, and accepting who I am, I was able to understand and appreciate others. This alone has had a transformative effect in both my personal and professional life.

I now feel more connected to myself, my purpose, my family, and my team.

Entrepreneurship can be a lonely journey, but it doesn’t need to be. We can always learn, improve, grow, and move forward.

95% of the population will never understand why we do it

Raymond Chou. Founder and CEO at Infront Consulting APAC. Kuala Lumpur, Malaysia.

Entrepreneurship can be both lonely and depressing; sometimes at the same time. It comprises of constant dark clouds and filled with daily heartbreak, and it is lonely because 95% of the population will never understand why we do it given all the pressures and stress that comes with it.

It can feels especially awful after you have had a particularly difficult day, and you come home and try your best to describe it to your loved ones only to be met with “stop doing it and get a job so you don’t have to suffer”.

Entrepreneurs are different to others; they do what they do for a purpose and for a higher vision, and any quest to realise the vision is filled with an army of challenges and sometimes well-intentioned people who try and stop them.

I had a great group of people, and new friends, with me but none of my old friends where there

Ron Lovett. Founder and Chief Alignment Officer at Connolly Owens, Founder and Chief Community Officer at Vida Living, Author at Outrageous Empowerment. Halifax, Nova Scotia.

The first time I heard the idea that “entrepreneurship is a lonely journey” was in my late twenties. I was running my security company and I had an Advisory Board. One of my Board Members–after our meeting–said, “Ron, I think you are going to do exceptionally well in business, but you will find that it can be very lonely journey.”

It wasn’t until my 30th birthday–when I organized a trip to Montreal, Canada–that this statement came to life for me. I had approximately 15 friends meet me, none of which were the friends that I had grown up with; most of the latter unfortunately could not afford the trip. Of course, I had a great group of people, and new friends, with me but I was sad that none of my old friends were there.

The feeling of loneliness has appeared multiple times during the journey, especially during very stressful times in business where I felt I had no one to lean on.

In 2007 I came across Entrepreneurs’ Organization (EO). Immediately after joining, I felt a sense of belonging. To be immersed, locally and internationally, with other business owners from different businesses, cultures, races, beliefs and experiences provided me with the support and push to learn and grow. I haven’t felt lonely since!

How wonderful is it that one’s mind can jump from idea to idea without disturbance from others?

Tony Falkenstein. Founder and CEO at Just Life Group Limited, Founder and CEO at Just Water, President at Entrepreneurs’ Organization. Auckland, New Zealand.

There are times on the entrepreneurial journey when the entrepreneur may feel lonely, but if a person feels entrepreneurship is a lonely journey overall, perhaps they are better off working for someone else.

In my experience, entrepreneurship is the most sociable and engaging activity that an entrepreneur can ever undertake. Sometimes the entrepreneurship game is played alone, but how wonderful is it that one’s mind can jump from idea to idea without disturbance from others, and that at other times you get to play the game of business with a whole team against a lively opposition?

What do you think?

Do you agree or violently disagree with anything shared in this article? Or do you have any of your own stories that you want to share? Pop them in the comments and I will personally reply.

Call to action 

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“I need to create space in my life for self-actualisation, to: (1) reflect; (2) define my core values; and (3) define the boundaries where I play.” – Ben Trinh

“Your values are what you believe about the world. Your values are the boundaries and the ethical convictions that you consider true in your world. They are not going to be true for everyone and don’t expect them to be as such; they are just true for you. These are the lines you won’t cross no matter how big your business gets.” – Ben Trinh

“What are the relationships immediately around you? Who do you bounce off and get energy from? Who do you share your problems with and do they deeply listen? These people are good first employees. They’re good for your first five employees because these people are the early doctors in your business. Our bookkeeper is a great example. When she came in through our doors she had never been a bookkeeper; she was a restaurant manager. But she said to me that she connected with our values, and wanted to be our bookkeeper. She was so clear in her vision that we hired her because you can train competencies but you cannot train character. Well.. you can.. it’s just a lot harder.” – Ben Trinh

“You will need hope and vision because you will need both resilience and grit when things get tough. It will give meaning to those moments when you feel like giving up and so I’d encourage you to piece together and deeply understand your vision, your passion, and your strengths. Have a tangible, descriptive picture of what the world looks like when the problem you’re solving is solved. It should be inspiring. It should be something that gets you out of bed every day. This is what will get you through the tough times.” – Ben Trinh

“Your business is your team; your clients; the people you surround with. A person by themselves do not make a business. Create a team around you that is based on your values and principles. When you say thank-you to the members of your team, anchor it in your values.” – Demi Markogiannaki

“Listen. Always listen. Identify what are the actual problems are that people have. Draw on their feedback and create a solution that will solve their issue. When we did that at WeTeachMe, I knew we were on the right path because people were willing to give money for the solution that I created.” – Demi Markogiannaki

“It’s never a good time and it’s never the right time. A lot of people approach me and tell me that they have an idea. Everyone has an idea. However, the person that wins is the person that executes the idea. In contrast, the person who over analyzes will one day turn 50 and they will still be analysing.” – Demi Markogiannaki

“It doesn’t matter how many books you read, or how much you think, or how many notebooks you fill with bullet points about the things you plan to do. The important thing is that you actually do something.” – Demi Markogiannaki

“In business, suffering is actually good. It’s what brings out the gems, it’s what builds character, it’s where you get your learnings, and it’s the way you humble yourself. So, I’d say in addition to hope, it’s about reframing our thinking around suffering.” – Ben Trinh

“I love what Demi said about listening and being an active listener. How can I listen better so that I draw out the key insights? And how do I fail and get through this as fast as I can, so that I can get the learning gems?” – Ben Trinh

“Jess and I were new graduates when we started the business and as new graduates, you know nothing. You have no shame asking for help because you come from a university environment where everyone needs to help each other so we had no shame asking for help and really latching on to feedback. We spent a lot of time reflecting and deepening our sense of self-awareness. You need the humility to be open-minded to other things and you also need to be an action person. It’s all great to be a philosopher and sit there and learn about the world, and how you’re terrible person or how you can be better, but if you don’t make your reflections a a tangibility in your life, then you’re not going be on that journey towards self-actualization.”  – Ben Trinh

With thanks to

Ben Trinh is the founder of Life Ready Physio & Pilates. Fresh out of university, Ben realised there was a fundamental problem in the physiotherapist’s business model. His solution has grown to 30 locations and over 300 employees in less than a decade.

Demi Markogiannaki is one of the founders of WeTeachMe. Demi worked with her co-founders to create a solution to help teachers find their students – but that wasn’t the solution they were looking for. After listening to their customers, WeTeachMe grew to become the go-to marketplace offering hundreds of classes to thousands of students.

About Masters Series by WeTeachMe

Masters Series is a show about inspiring entrepreneurs, creative thinkers, and visionary dreamers, and the stories behind how they built their companies.

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Question of the day

What was your favourite quote or lesson from this episode? Please let me know in the comments.