Working alone sucks

I am the CEO of a small healthcare tech company. My biggest source of job-related dissatisfaction is the fact that I work alone most of the time. I’ve always disliked the “It’s lonely at the top” arrogant cliche but now I must say I am feeling it.

My team of about 20 is distributed around the world. We have sales reps in the US and in Europe, all working from home to be closer to their markets and travel to see their clients. Due to legacy reasons, we have engineers working out of one European facility and a clinical team working from another European facility. I am sitting in an office in Montreal with two colleagues. I don’t have a CFO, COO or other peers with the same overall picture of the company and incentive structure that I have. I send progress reports to my Board of Directors once a quarter who nicely acknowledge receipt and ask some questions but don’t challenge me in a meaningful way.

Because my team is mostly remote and we don’t have any local customers yet, I spend the vast majority of my time dealing with emails and talking on the phone. Just thinking about my daily office routine reminds me of a Hemingway quote:

There is nothing to writing. All you do is sit down at a typewriter and bleed.

Anyone who knows me will tell you that I am (hyper?)active, extraverted and social. Sitting in front of the computer alone all day is as sub-optimal as it gets for my character.

In the first company I started, I had 2 co-founders who were also best-friends. We all sat in close proximity and had a weekly “Partners’ Dinner”. These dinners were a great time to share the ups and downs of the week and jointly steer the vision of the company. Later, when I worked in a management consulting firm, I mostly sat with my team around a large table in the client’s office. We traveled together, worked together, ate together and went out together. We also had frequent client interactions during the day. Overall, the sometimes annoying loss of privacy from Monday to Thursday were outweighed by the friendship, camaraderie and strong professional ties that we formed during that time.

I have only started realizing the negative effects of working alone on my mood and performance. As a result, I started getting involved in many activities outside of work to try to solve this problem. Some activities were helpful, while others further exacerbated my feeling of aloneness.

As example of a not so helpful activity, I went yesterday to a lunch event were I was told we would discuss the main issues affecting Canada/US trade for SMB’s. As about 50% of our business is with the US, I figured that would be an event worth attending. As it happens, we were probably only 3 entrepreneurs (out of 50) participants . Everyone else there was from some kind of government organization pushing their “program” or a service provider who was there to network. The lunch lasted 2.5 hrs and was filled with non-practical macro generalities (US exports represent 67% of Quebec foreign trade) and needless ceremony (“we are so honoured to have with us today Mr X, he is Honorary Chairman of Y committee”). It is impossible thatanyone gained something practical and valuable from the lunch. Driving back to my office, I felt even more isolated. I felt like I wasted time without any benefit whatsoever.

Of course this is only one failed example in a series of more successful attempts to find a solution to my situation. This post is getting longer than I intended it to be so I will stop here and write again soon about some of the things I am doing to improve my solitary working environment.

Update: This post has generated an interesting discussion on HN ( I should emphasize that it is not physically being alone (i.e., not enough contact with other people) that bothers me, it is the lack of peer-level teamwork towards a common goal that I lack.