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Are You Structured or Free Spirited?

By Feb 03,2017 Follow Me on Google+

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Understanding the environment in which you thrive, be it structured or free-spirited, can greatly influence your success or failure in work and life. Determine whether you are a structured or free-spirited person, and seek out similar people and situations. Like people, companies and organizations are also either structured or free-spirited; success comes from understanding which type of environment suits you.


Around six months ago, I was going to meet with an important investment banker in Los Angeles. It was not an ordinary bank-type office because it was located high in a skyscraper, and was full of wood paneling, dark fabrics, oriental rugs–and there was almost a complete absence of people anywhere. In fact, after entering the front door to the office, it felt like I had to walk a full 10 seconds down a long hall before I encountered an immaculate receptionist, sitting in front of what looked like a painting I had remembered studying in an art history class. The office was impeccable and very intimidating.

When I took a seat in the lobby area, I noticed that the magazines were all arranged perfectly on the table and were up to date. A few men I noticed walking by were all wearing expensive suits with cuff links. The receptionist sitting behind the desk was politely answering the phone, which rang softly every few minutes. I had been sitting there several minutes when an older woman walked up to the receptionist and started talking to her in whispered tones.

“I heard you left your station a few hours ago without asking for a replacement,” the older woman responded. I was around 20 feet away but there was such intimidating silence in this investment banking office that I could hear the entire conversation.

“I just had to run to the bathroom. I was not gone more than two minutes,” the receptionist said.


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“Well, one of the partners saw you away from the station. Why don’t you take the rest of the day off and go home and think about this. If it happens again we cannot have you working here anymore. You need to follow protocol whenever you leave your station, even if it is only for a minute,” the woman said.

The girl then stood up and walked over to the elevator, and the older woman took a seat at the desk.

I could not believe the exchange I had just witnessed. I knew exactly the sort of people I was in for meeting that day, and I knew that my meeting would under no circumstances work out with these people. They were obviously far too into structure, rules, and so forth and these were just not the sort of people I was going to be comfortable dealing with.

A few minutes later (at the exact time our meeting was scheduled to begin) the banker came out. He was standing so upright that I it looked as if he might fall over. I thought to myself that his shoes appeared so polished that they could be used as mirrors. His pants were perfectly creased. When we sat down I immediately noticed that the man had already prepared a detailed agenda, and he spent at least five minutes explaining to me what we would be talking about over the next hour.

I do not need to go into any more detail about this meeting because you probably already know what I am talking about when I describe the kind of people I was meeting that day. This was a structured organization that seemed to be populated (with the exception of the receptionist, who was sent home) with extremely structured people.

Structured people and organizations:

  • Keep their space organized and are very neat and tidy,
  • Have schedules and lists about how things are going to work,
  • Like to make sure there is closure in all situations,
  • Have many rules and regulations about the way things should work,
  • Do not have difficulty making decisions, and they stick to their decisions,
  • Tend to be a little stiff and judgmental,
  • Dislike accommodating changes,
  • Are usually on time (or even early) for their meetings and appointments,
  • Rarely change their minds, unless concrete and verifiable data warrants this.

When you enter any business office, you will generally find an office that is either like this, or alternatively, a more free spirited office, populated by free spirited people. Banks, law offices, and so forth tend to be more structured environments (but not always), and advertising agencies, newspapers and so forth tend to be more free spirited environments (but not always).

In a free spirited office, people will typically wander into work anywhere between 7:00 a.m. and 11:00 a.m. Sometimes they might even arrive later. For certain functions such as answering phones, of course, people will generally be there on time, but this is not always the case in a free spirited environment. Sometimes, people might not show up at all, and when this occurs, coworkers will generally pitch in, even if they have a job completely unrelated to answering the phones–or whatever position has been left unfilled for the day. In a similar manner, once the day is over, around 5:00 p.m., some people will have gone home; however, at 8:00 p.m. there are still likely to be at least a few stragglers working in the office. This is the way things work at a company like Google, for example.

In these types of companies, people might show up late for meetings. In addition, lots of other things occur that you likely would not find in most structured companies. For example, there might be no dress code at the office. People may seem to be having a bit too much fun at work. The company may not hold consistent performance reviews–or may not even hold them at all. Nonperformers might not be fired for not contributing, and instead, they might simply leave on their own after some time. There is somewhat of a “disorganized feel” around these sorts of companies, but the work still gets done. In fact, in a lot of companies like this, the organization may be the best in the world at what it does. I call companies like these free spirited companies.

Free spirited companies and organizations:

  • Do not mind, and may even have a proclivity to work in space that is less organized or tidy,
  • Do not particularly favor closure in situations, and often avoid it,
  • Do not like agendas and lists,
  • Can change their minds suddenly and on a whim,
  • Go with the flow,
  • Do not stick to schedules and have little awareness of the time, therefore they are often running late.
  • Have difficulty making decisions and sticking to decisions,
  • Often do things spontaneously,
  • Accommodate changes readily,
  • Do not like (and even hate) the structure of rules and regulations.

Just as companies are either predominantly free spirited or structured, so too are schools. When parents pick private schools for their children, they often choose a school based on whether or not there is a lot of structure incorporated into the institution. In virtually every major city I have lived in, out of the two best private schools, one can usually be defined as more structured, and the other can usually be defined as being more free spirited.

Schools, companies, and individuals are also generally either structured or free spirited. People perform and are happiest in the organizations that match the way they are.

  • If you join a free spirited organization, and are extremely structured, the chances are very good that you are not going to like your job, and are going to think the people around you are nuts.
  • If you are join a structured organization, and are a free spirited person, the chances are very good that you are not going to like your job, and are going to think the people around you are nuts.

The same thing applies to personal relationships: Free spirited and structured people typically do not get along all that well, since they see the world in two different ways. In fact, I would venture to say that when most marriages or relationships go bad, it is often precisely because the two people are opposites, in terms of being free spirited or structured.

A large part of your success or failure in your career and life will revolve around understanding whether or not you thrive in a structured environment or, instead, a free spirited one. I have found that people generally prefer one way of working and living over the other, and you may find that your success or failure in jobs, relationships, and so forth, often depends upon whether you are structured or free spirited.

You need to determine whether or not you are a free spirited or structured person, and to seek out mates, jobs, friends, and so forth that are like you. If you do not do this, then the odds are pretty good that you will experience consistent problems in your jobs, relationships, and your life.

It is relatively easy to figure out which sort of person you are. Here are some indicators that can help you with this:

  • Is it important to you that your work area is always clean?
  • Do you frequently change your mind about various things after making decisions?
  • Does it make you angry when others are late for appointments or meetings?
  • Do you prefer doing things spontaneously, or planning things out in advance?
  • Are you always punctual?

You should work with organizations that share your outlook. If you have failed in various organizations in your life, it may well have been due to the fact that you were working with an organization that was structured, although you are free spirited. The same applies to relationships and more. This should be one of the most important factors you consider in your decision in choosing the people you work and associate with, because it will determine your success or failure in working with them.


Understanding the environment in which you thrive, be it structured or free-spirited, can greatly influence your success or failure in work and life. Determine whether you are a structured or free-spirited person, and seek out similar people and situations. Like people, companies and organizations are also either structured or free-spirited; success comes from understanding which type of environment suits you.

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