Leadership Toolkit: Is entrepreneurship a lonely journey?

Camille Monce —  October 19, 2020 — 2 Comments


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.

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My goal is to help 1,000,000 people. My wish is to have these articles shared 1,000,000 times through the various social networks. For this reason, I provide this collection online for free and all I ask of you is this: If any of these articles have helped you in any way, please take a moment to share on social media, email to someone you think will find benefit, or print and leave it on the desk of someone whom you believe has the motivation, but lacks the tools to take themselves to the next level.

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2 responses to Leadership Toolkit: Is entrepreneurship a lonely journey?

  1. I would never regret my Entrepreneurial journey,,, the freedom, the excitement is all worth the journey!

    • I 100% agree with you Ai-Ling. The opportunity to experience the journey with others, to create something infused with one’s values and how one sees the world, to build deep bonds with those one admire and respect… there are a lot of silver linings. Of course, there is a flipside; the sacrifices, the late nights, the pressure!

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