Have you ever wondered why entrepreneurs often state “it is lonely at the top”? Is it a fact of the entrepreneurial life or is it a function of their lifestyle in growing up – the age old nature versus nurture debate. I am sure that there are valid arguments for both sides of the debate. Regardless of where it originates from, many entrepreneurs develop lifestyles or coping mechanisms that offset what may be a debilitating feeling. In my case I think the nurture part of the equation has been more dominant in shaping the “lonely at the top” feeling than the nature aspect of entrepreneurship.

Friendship is Fleeting

Looking back at my childhood I can understand now why I have so few friends. Between the start of kindergarten to my university graduation I went to 19 different schools – sometimes more than a couple per year. This was a result of my parents going through a tumultuous relationship of being together and then apart on numerous occasions and finally resulting in their divorce when I was about to turn 15. The constant movement from school to school precluded developing any lasting relationships, in fact, only one still exists with a friend from the last university I attended, Simon Fraser University in Burnaby, BC, and even that one is sporadic at best! Switching schools just became part of my life and I was always able to quickly fall into a place of acceptance within any school system based on my love for sports and arts. I excelled at baseball, hockey, soccer, basketball, track and field and volleyball – learning each one based on my age, season and geographic location – usually between the Eastern Townships of Quebec and the communities surrounding the mining town of Sudbury. Team-mates quickly became friends and provided me with the socialization I needed during those impressionable youth years. In art I became immersed at different times in abstract pastels or soapstone sculptures and within the drama department in high school with school plays. The artwork allowing for deep passionate focused alone time and the drama allowing socialization with a different set of friends than the jocks.

Salesmanship Starts Young

I also became entrepreneurial at the young age of 9 – selling individual beads on leather strings deconstructed from full bead necklaces I bought, with proceeds from babysitting, during our summer camping trips to Bar Harbor on the coast of Maine. I then sold them the following school year to relatives and friends. My favorite entrepreneurial memory was a school fund-raiser when I was in grade 3 for who could sell the most chocolates bars – with the grand prize being a pair of tickets to a Montreal Canadians game or a pair of tickets to the Ice Capades featuring Toller Cranston. Since we lived outside the town of Cowansville in the Eastern Townships where I went to school, I quickly realized that most homes in Cowansville were already “chocolate-bared” out. So I would convince whoever picked me up after school to drive to a different town before we went home. This was usually my Mom or grand-father, and they would drop me off at one end of a new town and pick me up at the other end in an hour or so. I would make my way through to the other end selling my chocolate bars door to door and as the month of the fund-raiser went on, the towns I got dropped off in became further and further away from Cowansville. This became a great selling feature as a lot of the people who answered the door couldn’t believe that an 8 year old was in their town selling chocolate bars that was from a town 20 or 30 kilometers away. The pitch was irresistible!!! Every day I would sell my two boxes of chocolate bars (12 bars per box, so 24 total) and return to the school for more the next day. By the end of the month I had sold just over 600 chocolate bars, greatly surpassing the next closest kid in grade 7 who sold 250. I loved the Montreal Canadians and that goal drove me every day to keep going – I visualized being in the first row by the glass seeing my heroes like Jean Beliveau out on the ice. But in the end, I realized the sacrifice my Mom made driving me all around and that she loved Toller Cranston, so I made the decision to go to the Ice Capades with her as this was something she would never be able to afford to justify doing for herself – the Canadians game would happen another time for me! It was a sacrifice that I have questioned from time to time – but I have always come to the same conclusion, that it is greater to work towards a goal and be successful than the receipt of any rewards for achieving it. The journey is more important than the fruits of the reward – that is where life is lived. This success also taught me that the hours being put in by myself in the sales process were motivated by the vision of attaining the goal I set.

Success Truly is Lonely

In the tail-end of my university degree, which took me 7 years to complete since I worked full time throughout my studies and could only manage a part-time course load each semester, I embarked on my first truly successful business venture. I became a financial planner and soon bought out all of my partners to control the firm. Although I had a couple of silent partners during this process it really was up to me to develop the strategy and vision of how the firm moved forward. So it was during this process that I got stuck on ego-building (as related in a previous blog: “Entrepreneurial Ego is a Double-Edge Sword!”) and joined the Young Entrepreneurs Organization, now the Entrepreneurs Organization (“EO”), as I craved to be with others that shared similar aspirations but also felt they didn’t have the direct peer group that they could share their success, failures, joys and frustrations with. EO has always been a safe haven for those entrepreneurial leaders that experience “being lonely at the top” to become associated with a similar peer group. The number one program within EO has always been the Forum program where business owners meet on a monthly basis to share their experiences, business and personal, in order to create a close-knit peer group and eliminate that “lonely at the top” feeling. Some Forum members become friends for a lifetime, but in my experience, none of the Forum groups I have been a part of have had the lifetime friendship development for myself that I would have expected and seem to observe in other EO Forums and their member relationships. I have often told my Forum mates that I am not actually looking for friendship; I am looking for shared experiences on a deeper level and in a trusting environment! For me, I again look back to my school years and see the same pattern of friendship development I experienced then, a few friends for a few months or years but not a lifelong experience – the nurture experience, or lack of it, demonstrating itself again.

Serial Entrepreneurism

So not only have I switched schools often, in my business career I have had 5 qualifying EO businesses over the past 20 years – and am currently determining what number 6 will be. It seems that every 2 to 7 years I need to switch it up – new business, new partners, new employees, new supplier relationships, new clients, and new friends. In the last business I sold in July of 2012 it became more evident than ever that after the business sale I was really only known for that business – not for who I am as an individual. This manifests itself in the relationships that I had when I was an owner in the business and the relationships I have now. While owning the business there were always things to do, people to see and places to go – and now that I have sold it I still have some of those three aspects, but now I dictate what they are versus others calling upon me to experience them together. So is that friendship – or just the process of using business contacts to further my own goals. Certainly, I am lonelier when I no longer own a business that created the appearance of friendships. In essence, I think in many people’s mind the business was who I was and so when it is gone then there is no reason to reach out to me to share something and vice versa.

When Lonelier Does Not Mean Lonely

So although I state I am lonelier now without a business I am definitely not lonely! One of the first things I did after selling my previous business was to come up with a set of goals as to what my next business has to create for me. My Top 3 goals, in order of importance, for the next business are:

  1. That the business should be a buy-out target within a 10 year time frame. This means that I am starting with an Exit strategy already in place and will be able to shape and grow the business in order to maximize the value of that liquidity event when it occurs;
  2. That the business accommodates itself as a “lifestyle business”. This means it has to be flexible enough to balance with my personal life, home life, hobbies and interests.
  3. That the business allows me to take advantage of my core strengths which include leadership, organizational structuring, finance and having the ability to figure out solutions when others can’t.

By defining what I am looking for it has allowed me to easily vet opportunities to whether they match up with these goals or not. If they don’t hit all three goals to start with then I do not proceed further in my research on them. This keeps me busy looking at opportunities and spending further due diligence time and effort on the couple that have passed my Top 3 Goal test to start with. This engagement has kept loneliness at bay and my mind sharp on what my next venture will be.

Getting Back What I Put In

The final part of the solution for avoiding “being lonely at the top” for me is to stay actively involved in volunteer work that is meaningful to me and I am passionate about. So for me that means spending time giving back to other entrepreneurs to help them grow their businesses. I do this by being a Mentor to 3 or 4 other businesses at a time through the EO Accelerator program. I also want to support the athlete and artists that are the current or future leaders in their area. So by being a Board member of the Spartan Foundation which is dedicated to building the Complete Athlete and by buying works of art from young aspiring artists like Zoe Pawluck (www.zoepawluck.com) I can stay engaged and help build others.

So although it is often lonely at the top as an entrepreneur, and I am predisposed towards it through my nurture experiences growing up, I have found ways to help mitigate it and hopefully nurture others to learn how to deal with it as opposed to feeling trapped by the nature of it!!!

I’ve been saying it ever since I first tried them. Talking about useful link now. Had many assignments every week, almost full time job, etc. Needed it a lot back then.


Leave a Reply

Your email address will not be published. Required fields are marked *

Looking for something?

Use the form below to search the site:

Still not finding what you're looking for? Drop a comment on a post or contact us so we can take care of it!

Follow Jon on Twitter

Contact Jonathan Mara

Jonathan Mara - Guardian Angel Consultants Ltd.



 Skype: Jonathan.Mara