Unconventional, Entrepreneurial Lives and the Challenge of Loneliness


I think about entrepreneurship in broad terms — as more a life idea than a business one. Jim Collins has said that people who lead entrepreneurial lives — in my book I call them “life entrepreneurs” — reject the paint-by-numbers approach, take out their own blank white canvas, and try to paint a masterpiece. He says, “Try to create a life so idiosyncratically you that it fits you like a glove.”

Chris Guillbeau, on his excellent blog The Art of Non-Conventional Living, casts entrepreneurship in a similar light. He defines “non-conformity” as “a lack of orthodoxy in thoughts or beliefs” or “the refusal to accept established customs, attitudes, or ideas.” Tim Ferriss is another champion of rejecting the 9-to-5 grind and finding work that is fun, meaningful and maximizes freedom to travel and accumulate new experiences.

These philosophies have much to recommend it, even beyond the obvious. For example, as I’ve written, one way to reduce jealousness of other people — one way to stave off the kind of envy that can consume high achievers — is to create a life so unique to you that it destroys reasonable comparisons. Conventional life paths are crowded with others, and there will always be someone of equal age or background walking ahead of you. Walk alone on your own path, and direct comparisons become harder. Envy goes down, genuine happiness for others’ achievements goes up, and success and progress becomes more about achieving individually defined goals and less about keeping up with the Joneses.

But for all the rah-rah-rah, there are serious, under-discussed challenges with an idiosyncratic, comparison-destroying life. The first has to do with motivation. If the will to advance your situation comes only from the guy who’s a few inches in front of you, you’re screwed, since there will be fewer obvious peers who can directly push you to be all you can be. (Anyone in law or medical school, by contrast, has a million peers with whom he can relate and feel challenged.) So you gotta be a self-starter or otherwise intrinsically driven.

The second more serious challenge relates to emotional relationships. Walking on your own path means…you are walking alone. It’s hard to become close to people, primarily because shared experiences are the lifeblood of relationships, and if you’re leading a non-conventional, non 9-5 life you’re probably accumulating unique experiences. Fewer people can understand why you do the things you do. You feel misunderstood, which is problematic because as social creatures we seem to spend most of our time trying to be understood — trying to express what’s inside our head. Many late night ice-cream binge sessions start with the feeling that nobody “gets us.” You feel lonely.

In his book Loneliness: Human Nature and the Need for Social Connection, John Cacioppo says, “Loneliness reflects how you feel about your relationships. Depression reflects how you feel, period.” People living entrepreneurial, high-achieving lives struggle to find common ground with others and so struggle with intimate personal relationships and so struggle with loneliness more than most.

I am not a lonely person. But I do have my moments. Everyone does. Regardless of the conventionality of one’s life or strength of relationships, occasional bouts of loneliness might fit under the David Foster Wallace header of “What It’s Like to Be a Fucking Human Being.” Which is to say, it’s universal. Perhaps even timely. Record numbers of Americans say they have no confidante, and record numbers are living alone.

So no shame in talking about it. Here’s how I think about the loneliness challenge at a “strategic” level.

First, in my relationships, I emphasize strong ties over weak ones. There’s not a question in my mind that people with three intimate friends are less lonely than people with eight medium-strength friends. Of course, being young and uncertain, I’m still meeting plenty of new people, planting new seeds, maintaining an infinite-number of (surprisingly rewarding and useful) email-only relationships, and letting some strong-ties fade to make room for new relationships better suited to my evolving self.

Second, I work on becoming a better communicator so I can express myself and what I’m feeling to others, so as to help the process of feeling understood.

Third, just as loneliness and depression differ, so does loneliness and solitude. There is a difference between being alone and feeling alone. I love batches of solitude. I hate loneliness. But I need to remember that much as I love being alone, too much solitude — too much away time from my relationships — can induce loneliness. As A.C. Grayling put it, “Life is all about relationships. By all means sit cross-legged on top of a mountain occasionally. But don’t do it for very long.”

There are also some useful “tactics.” Most basically, I try to stay in touch with people I know. Simple, but without it your relationships will go nowhere. I also talk about the topic with other people to hear how they think about it. Seth Roberts, for example, has a tip he calls “faces in the morning, voices in the afternoon.” When you wake up, try to look at human faces (in-person, on TV, on the computer, or even yourself in the mirror). In the afternoon, listen to the radio or podcasts of humans talking. Listen to voices.

Bottom Line: Unconventional, entrepreneurial lives are not all peaches and cream. Accumulating lots of unique experiences necessarily means you’ll have less overlap with others, making it harder to form intimate bonds, making the challenge of loneliness more acute.

Below the fold are my favorite sentences (direct quotes) from the book Loneliness by John Cacioppo:

    • Their distinctive quality is not the ability to give a great party or to sway the masses, but an element of warmth, openness, and generosity that draws others in.


  • In the United States in 2000 there were more than twenty-seven million people living entirely alone, thirty-six percent of them over the age of sixty-five. According to projections by the U.S. Census Bureau, by 2010 the number of people living alone will reach almost twenty-nine million.



  • For the self, the essential dimensions are personal, relational, and collective, onto which we can map the three corresponding categories of social connection: intimate connectedness, relational connectedness, and collective connectedness. When events knock one of the three legs of the stool out from under you-intimate, relational, or collective-the safe and comforting feeling of stability falls away, and even someone who has always felt intensely connected can begin to feel lonely.



  • In 1988 an article in Science reviewed subsequent research, and that meta-analysis indicated that social isolation is on a par with high blood pressure, obesity, lack of exercise, or smoking as a risk factor for illness and early death.



  • one factor within the Type A cluster-hostility-was the best variable for distinguishing those who would develop heart disease from those who would not.” This was a powerful finding for our own work, because, like loneliness, hostility is an attribute that can persist over time. Like loneliness, it is characterized by mistrust, cynicism, and feelings of anger that lead to antagonistic or aggressive behavior.



  • Most behaviors are not randomly distributed but are socially patterned, meaning that they tend to occur in clusters. Many people who drink heavily also smoke. Those who eat a healthful diet also tend to exercise.



  • when people feel lonely, they are far less likely to see any given stressor as an invigorating challenge. Instead of responding with realistic optimism and active engagement, they tend to respond with pessimism and avoidance. They are more likely to cope passively, which means enduring without attempting to change the situation. This pattern of “grin and bear it” (while boiling inside) carries its own specific costs.



  • Cuteness was part of what made primeval mothers long to be with their babies. It also made fathers, grandparents-and today even passersby in grocery stores-want to interact with these miniature humans, amuse them, and protect them. There is now even a science of cuteness, as engineers in robotics try to make computerized companions that will have the same huggable appeal as a human baby.



  • Physical manifestations of connection such as hugs and back rubs increase oxytocin levels in the areas being touched.



  • The Germans have a word for closely attuned perception of another’s emotional state. They call it Einfiihlung, meaning “feeling into.”



  • Feeling lonely increases a person’s attentiveness to social cues just as being hungry increases a person’s attentiveness to food cues.



  • Studies show that truly enjoying these positives and making the most of them is even more important to the health of a marriage or other intimate relationship than being supportive during hard times.



  • Female jurors are actually more likely than their male counterparts to believe that a rape victim somehow contributed to her fate. “After all,” the juror thinks, “if this happened to her without her behaving badly or taking stupid risks, then it could happen to me! She has to be somewhat responsible for what happened; otherwise, I can never feel safe.”



  • the young are often so desperate to connect with peers that they sacrifice their own identity as well as their good judgment.



  • when people feel lonely they are actually far less accepting of potential new friends than when they feel socially contented.



  • love and kinship mingle with resentment and competition at every juncture.
  • As cultures encompass more variety in their mores, the absence of narrowly defined and rigidly enforced standards places even more of a burden on the brain’s executive function, not only to guide self-regulation, but to calibrate, discern, and fine-tune appropriate responses.



  • Anyone who has ever been in the military or played a team sport knows that punishing the whole group for the screw-ups of one individual is the best way to apply pressure to get the slacker to improve.



  • “The bottom line … is that when you have people with shared standards, and some who have the moral courage to sanction others, informally, then this kind of society manages very successfully.”



  • human children will almost always help others complete a simple task, spontaneously and without reward, by the age of fifteen months.



  • Other research confirms what spurned lovers know — that when people feel rejected or excluded they tend to become more aggressive, more self-defeating or self-destructive, less cooperative and helpful, and less prone simply to do the hard work of thinking clearly.



  • Perhaps it should not be surprising that so many more Americans today than twenty years ago have no confidants. To whom can you speak in confidence when your most agonizing personal issues might have to do with your spouse?


22 comments on “Unconventional, Entrepreneurial Lives and the Challenge of Loneliness
  • Great post (and Chris G’s Art of Unconventional Living one of my favorite blogs also). As a fiction writer who felt wildly out of place when she was living in Silicon Valley with her then-husband, the last thing I ever considered myself was “entrepreneurial” to the point where I even wondered why I feel drawn to your blog (& your book, & some of the books you recommend). But “life entrepreneur” is a concept probably any writer can relate to, as is the problem of staying social and connected when your ‘job’ requires deep solitude, an independent spirit and a healthy dose of rebellion (or at least the unflagging willingness to go against the societal grain). Thanks for it.

  • “Painting the canvas” has become a running joke around the office. Whenever our CTO has to deal with a server crash, I’ll ask “how’s that canvas painting going for you?”

  • I’m cynical of “unconventionality”. I’ve lived in Los Angeles for over a year and a half now and I’m really starting to think that “conventional people” make up maybe 40% of the non-immigrant population and the majority is “unconventional”. It’s like the old long tail thing and we only think of it as “unconventional” because it’s not much of a bloc beyond some basic platitudes about rejecting the middle class life of fine china and pretending to know something about wine.

  • Are you sure you can be less jealosy prone if you are off-beat? People will still envy your freedom and stick it upon inherited wealth or family support. Then you have the institutional due diligence needing a regular weekly remittances into your bank to grant you an insurance/mortgage(post crisis :-). Try telling them you live on occasional windfalls, many times the possible annual wage, it’s a clear no go. So off-beat lives don’t just influence your present moment, you also will have to find an off-beat way to manage your future as well.

  • Great post. Could you kindly write one on hostility or disdain sometime? My healthiest relationships come out of the typical virtues–love, acceptance, etc.–but often my most unusual ones come out of my cruelty or exclusivity. Exclusivity is a big part of friendships. I am always puzzled by figures like Jesus Christ or Mahatma Gandhi. Would you like to be friends with someone who was open to everyone?

  • No, I think you have to discriminate at some point. Total, unconditional
    love and acceptance of everyone seems nigh impossible, and someone holding
    this philosophy is not someone I would probably befriend….

  • One of the best posts I’ve read for long. Just realized that “the young are often so desperate to connect with peers that they sacrifice their own identity as well as their good judgment” so applies to me. Thanks for the insightful read 🙂

  • Ben
    such a bountifully perceptive post on the up and down sides of become one-of-a-kind in ones work and, relatedly on ensuing loneliness, depression, solitude + the universality of that experience.

    Re strong ties and weak – and what happens to “us” when we become part of group – we gravitate towards taking extreme stands on the edge of the group to, counter-intuitively conform to the group, secure acceptance: Read 2 books on that theme
    Going to Extremes
    The Big Sort

    This phenom, as Cass Sunstein points out, affect decisions in juries, politics, terrorist groups, religious orgs and more

  • Great article. Thanks for bringing up this book. I’m putting it on my “to read” list.

    I have always struggled with lonliness and I’m not even living an “entrepreneurial life”… not yet anyway. Part of it has to do with my hearing loss, part of it has to do with the fact that I think/act differently than most of my peers. I enjoy having periods of solitude, like you, but I frequently battle with being okay with it and wondering if I’m doing something wrong. There’s a lot I could say about lonliness, but for your sake, I’ll keep it short. Thanks for writing this, I feel like someone ‘gets’ it.

  • Hi-

    The quote would make more sense to me if I knew what the “positives” that it’s referring to are. 🙂 Could you please tell me what they are?


    “Studies show that truly enjoying these positives and making the most of them is even more important to the health of a marriage or other intimate relationship than being supportive during hard times.”

  • I would encourage you read a book with a focus on solitude instead of loneliness. Both have common physical manifestations (the lack of others), but are approached and experienced in very different ways.

    I went on a streak a year ago on the subject and greatly enjoyed “Solitude: A Return to the Self” by Anthony Storr. My preference for solitude has always been a difficult topic for me and this book (and others) have helped me better understand that part of me and how I [don’t] fit the rest of society.

  • Well – we all set our own limitations. If you believe unconditional/universal love and or acceptance is impossible – it will remain so.

    What I have found is this – upon gaining self-acceptance – compassion arises – non-acceptance of all others then becomes the impossible.


  • this one’s a real tear jerker, ben. in the spirit of finding a connection with your post, let’s build a snowman together in our cold, lonely world before we part ways again 😉 til the next time, i hope all is well with you.


    your fellow friend in loneliness

  • Awesome post, Ben. We are always told in youth that you can’t please everyone, but not until we break away and truly embark on our own do we realize the truth of this statement. I am and have been a big fan of Tim’s and Chris’s blogs for a while. I’m going to read your post on “weak ties”…Greg said you had great insights on that topic.


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  • Our Swedish author August Strindberg wrote at the age around 60: I need company but I must live alone, to an acquaintance inviting him to live in his house, or something to that effect. Strindberg was very challenging and productive and – no doubt – had a lot of lonely moments in his life.

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