Matching Personality to Entrepreneurial Choice: Part II

dreamstime_357982So Which Type Are You?

If you took The Self Directed Search, as I recommended from Part I of this post, while you may have had a strong hunch which personality traits were most dominant for you, I bet you were also surprised by what the tool revealed to you about your second and third strongest skills. Developing this self-awareness in itself  often can dramatically influence and change your goals and career pursuits immediately.

In order to help you see into how important the position is of each of the three letters the SDS produces, explore these stories:

The Realistic (R) Personality

Sheri had always loved the theater. She was fascinated with how it worked behind the scenes and enjoyed working with her hands. So when the opportunity came to work as an assistant for a New York set designer for Broadway theaters, she jumped at the chance to quit her full time job as a Pilates, and Yoga instructor.

As a child Sheri had been obsessed with miniatures, and had designed and constructed from scratch a row of dollhouses. Sheri also had learned how to make many of the pieces of furniture inside her dollhouse and showed quite an eye for interior decorating. She did a lot of research in her teens to find the best sources for materials, fabrics and the occasional store bought miniature lamp or accessory.

After Sheri worked for five years on Broadway doing set design, she launched her own business selling miniature set designs of well-known scenes from theater, movies, and television. She now sells them now in Hollywood to the stars as original artwork.

Sheri’s SDS code is ARE–Artistic, Realistic, and Enterprising. It was the “R” in Sheri’s personality that directed her to the right artistic (A) endeavor to produce a financially successfully turn it into an entrepreneurial activity (E).

The important point of Sheri’s story is that frequently the second letter of the three-letter code offers the most opportunity to combine skills to identify your unique possibilities to entrepreneur the arts.

Realistic individuals are active, stable, and enjoy hands-on or manual activities such as building, mechanics, machinery operation, and athletics. They prefer to work with things rather than ideas and people. They enjoy engaging in physical activity and often like being outdoors and working with plants and animals.

People who fall into this category generally prefer to “learn by doing” in a practical, task-oriented setting, as opposed to spending extended periods of time in a classroom. Realistic types tend to communicate in a frank, direct manner and value material things. They perceive themselves as skilled in mechanical and physical activities, but may be uncomfortable or less adept with human relations.

Realistic types prefer work environments that foster technical competencies and work that allows them to produce tangible results.

The INVESTIGATIVE (I) Personality

Jacob was always interested in photography and mostly in color and light, but his Dad wanted him to go to engineering school.  While Jacob dutifully studied engineering, his obsession was with color and light. An amateur photograph, he often captured photographs that were nothing but streaks of light.

One day, a stranger who was viewing some of these photographs asked Jason if he had ever worked with neon.  That was all it took for Jacob began to explore the process of creating neon.

With his engineering background, neon became the perfect art form for Jacob. He opened his studio Light Writers (  in 1982 and was very successful. But that’s not the end of the story.

In the eighties, neon designs were not as common as they are today. One day Bruce Neuman, one of the most famous neon artists in the entire world, walked into Jacob’s studio and asked if Jacob could execute a design he had made.

Jacob, who had no idea who Neuman was, said “sure” and proceeded to follow Bruce’s instructions to construct an exceptional piece of art. The forces of coincidence and irony were clearly working for Jacob Fishman in that moment, as that experiment has blossomed into a 20-plus year working relationship. Today Jacob Fishman creates and designs all of Bruce Neuman’s neon sculptures and helps install then in museums around the world to this day.

Jacob’s chose of neon was the perfect and pivotal use of his investigative personality type. His SDS code is AEI- Artistic, Enterprising and Investigative. It was by aligning the “I” properly in his work and combining it with his art and entrepreneurial capacity that made Jacob who he is today.

Investigative individuals are analytical, intellectual, and observant, and enjoy research, mathematical, or scientific activities. They are drawn to ambiguous challenges and may feel stifled in highly structured environments. People who fall into this category enjoy using logic and solving highly complex, abstract problems. They are introspective and focused on creative problem solving; therefore investigative types often work autonomously and do not seek leadership roles.

The investigative personality places a high value on science and learning, and perceives itself as scholarly and having scientific or mathematical ability but lacking leadership and persuasive skills. The preferred work environment of the investigative type encourages scientific competencies, allows independent work, and focuses on solving abstract, complex problems in original ways.

The SOCIAL (S) Personality

Joanne majored in bassoon in college. She managed to make a living, but just barely, teaching private lessons and taking whatever gigs came her way. But as time marched on Joanne felt unhappy with her situation and with my encouragement decided to take the SDS test and explore her options.

Joanne’s three-letter code is SAC—Social, Artistic and Conventional. Until she took the SDS it never even occurred to Joanne that the lack of social interaction inside her day was causing her to be so miserable.  After compiling a series of potential jobs from the occupational finder list for each letter of her code, with my help, Joanne realized she would be very happy working for an arts organization, preferably an orchestra, as their personnel manager. While Joanne loved to play music and teach, her main desire was social interaction and having more of that in her day would make her the happiest. Within six months of taking the test Joanne found a position working for a major symphony orchestra and continues to flourish in her new found working environment both personally and professionally.

Social individuals are humanistic, idealistic, responsible, and concerned with the welfare of others. They enjoy participating in-group activities and helping, training, caring for, counseling, or developing others. They are generally focused on human relationships and enjoy social activities and solving interpersonal problems. Social types seek opportunities to work as part of a team, solve problems through discussions, and utilize interpersonal skills, but may avoid activities that involve systematic use of equipment or machines.

The social personality genuinely enjoys working with people; therefore they communicate a warm and tactful manner and can be persuasive. They view themselves as understanding, helpful, cheerful, and skilled in teaching, but lacking mechanical ability. The preferred work environment of the social type encourages teamwork and allows for significant interaction with others.

The ENTERPRISING (E) Personality

Michael Buegg was working on his MBA at Kellogg School of Management at Northwestern University in Evanston, IL when, as a student myself, I first met him. He was a quirky, highly intelligent entrepreneurial spirit and was always willing to try new things and take risks.

I was highly amused when he decided to take an acting class because he was not at all someone who was emotive. He was a thinker and a strategist and good with facts and figures. Yet Mike continued to study acting as he earned his MBA.

Upon graduation, Mike combined his love of acting with his passion for business to become an executive producer in the film industry. His credits include Little Miss Sunshine, starring Greg Kinnear, Alan Arkin and Steve Carell; Thank You for Smoking; Beerfest, and Chumscrubber. Little Miss Sunshine received a nomination for Best Picture as well as individual nominations in the Best Supporting Actor, Best Supporting Actress and Best Original Screenplay categories.

Mike’s three-letter code is unusual, with multiple letters in the first position, offering him many more options to choose from because of the uniformity and strength of so many different skills. His first letter is RIAEC—Realistic, Investigative, Artistic, Enterprising, and Conventional—indicating that Mike’s strengths are equal in these areas. In his second position is S–Social.

Entrepreneurs need to wear lots of different hats in developing an economic creative venture. Having many skills in a position of equal strength makes his career choice and excellent use of his talents, and as a result, he is being handsomely rewarded.

Enterprising individuals are energetic, ambitious, adventurous, sociable, and self-confident. They enjoy activities that require them to persuade others, such as sales and seek out leadership roles. They are invigorated by using their interpersonal, leadership, and persuasive abilities to obtain organizational goals or economic gain but may avoid routine or systematic activities. They are often effective public speakers and are generally sociable but may be viewed as domineering.

Enterprising individuals view themselves as assertive, self-confident and skilled in leadership and speaking, but lacking in scientific abilities. The preferred work environment encourages them to engage in activities such as leadership, management, and selling and rewards them through the attainment of money, power, and, status.

The CONVENTIONAL (C) Personality

James wanted to be in a rock and roll band more than he wanted to go to college. His father told him to go into accounting because he was good with numbers and being an accountant was a sure way to earn a decent living. James took his father’s advice, entered college, and majored in accounting.

He also continued to play his bass guitar and started a series of rock and roll bands with his friends. While none of his groups became really successfully, several of them continued to play in bars and venues long after James moved on to form the next group.

Eventually James realized that his dreams of making it as a rock artist (his creative label) were never be a real part of his life. When James graduated from college and passed the CPA exam he decided to use his accounting degree and combine it with his love of rock and roll. He sent his resume to recording labels around the country and because of his artistic background, and pursuit of music, despite his lack of great success with his bands, The Zomba Label Group hired him as an accountant and he has been there ever since.

I spoke to James recently and he told me that while he still plays guitar for fun, his real joy is doing accounting work for a number of big names that are on the Jive Record Label under Zomba. As James put it, “It may not be my money, but it sure is fun playing with these artists on paper.”

James’s SDS code is CIA—Conventional, Investigative and Artistic. His use of accounting to help Jive Records, the artists, and himself make money is a perfect combination of his talent and love of rock and roll music.

Conventional individuals are efficient, careful, conforming, organized, and conscientious. They are comfortable working within an established chain of command and prefer carrying out well-defined instructions to assuming leadership roles. They prefer organized, systematic activities and have an aversion to ambiguity. They are skilled in and often enjoy maintaining and manipulating data, organizing schedules, and operating office equipment.

While a conventional personality rarely seeks leadership or “spotlight” roles, they are thorough, persistent and reliable in carrying out tasks. Conventional types view themselves as responsible, orderly, efficient, and possessing clerical, organizational, and numerical abilities, but may also see themselves as unimaginative or lacking in creativity. The preferred work environment that fosters organizational competencies, such as record keeping and data management in a structured operation, and places high value on conformity and dependability.

The ARTISTIC (A) Personality

Whenever Jeff’s dad was looking for Jeff, all he had to do was go out in the garage. “Jeff picked up a guitar when he was 4 and I swear never put it down”, his dad often said.  If it wasn’t for Jeff’s love of music and devotion to learning the guitar it’s likely that Jeff’s life, in the conventional world, might not have amounted to much.

He far preferred to be playing music than studying for a test in school. He barely made it through high school, not because he was not capable but because he simply was bored. Jeff spent most of his time writing music and had enough written to fill 2 bound books full with original music and poems. At the age of 18, Jeff was the leader of his 7th band.

If you ever had a chance to talk to Jeff you can see how intelligent he is and how vibrantly and passionately he expresses his music through his own playing; and the discipline he devotes to building his music in his band.

Jeff started a performing degree at Illinois State University but landed a record contract in the middle of his sophomore year with Jive Records and has never looked back since.

Clearly Jeff is an artistic personality. Jeff’s SDS code is AES- Artistic, Enterprising and Social. Capitalizing on his enterprising ability and social nature are key elements to his success as an artist and allow him to find economic viability with his artistry.

Artistic individuals are original, intuitive, and imaginative, and enjoy creative activities such as composing or playing music, writing, drawing or painting, and acting in or directing stage productions. They seek opportunities for self-expression through artistic creation. People who fall into this category prefer flexibility and ambiguity and have an aversion to convention and conformity.

Artistic types are generally impulsive and emotional and tend to communicate in a very expressive and open manner. They value aesthetics and view themselves as creative, non-conforming, and as appreciating or possessing musical, dramatic, artistic, or writing abilities while lacking clerical or organizational skills. Their preferred work environment uses their creative competencies and encourages originality and use of the imagination in a flexible, unstructured setting.

Activities, Values, and Habits of the Personality Types

As creative individuals and artists, you know what the artistic personality is like, but what you must learn is that regardless of whether the A is first, second, or last in your three letter code, it is only ONE component of what you need to make your art vibrant, sustainable and economically viable as your life’s work.

What Kinds of Activities Do You Engage In?

  • Realistic types like activities that involve the use of machines, tools, and things.
  • Investigative types prefer activities exploring and understanding things and events.
  • Artistic types enjoy reading, writing, and all musical and artistic activity.
  • Social types prefer their activities to be organized around helping, teaching, counseling, or serving others.
  • Enterprising types enjoy persuading or directing others.
  • Conventional types prefer to follow orderly routines and meet clearly defined standards.

What Kind of Values Do You Have?

  • Realistic types value monetary rewards for observable accomplishments, honesty, and common sense.
  • Investigative types value knowledge, learning, achievement, and independence.
  • Artistic types value creative ideas, self-expression, and beauty.
  • Social types value servicing society, fairness, and understanding of others.
  • Enterprising type value financial and social success, loyalty, risk taking, and responsibility.
  • Conventional types value accuracy, making money, thrift, power in business, or social affairs.

How Do You See Yourself?

  • Realistic types see themselves as practical, conservative, and having better manual and mechanical skills than social skills.
  • Investigative types see themselves as analytical, intelligent, skeptical, and having better academic skills then social skills.
  • Artistic types see themselves as open to experiences, imaginative, intellectual and having better creative skills then clerical or office skills.
  • Social types see themselves as empathetic, patient, and having more social skills than mechanical ability.
  • Enterprising types see themselves as confident, sociable, and having more sales and persuasive ability then scientific ability.
  • Conventional types see themselves as having better technical skills in business or production than artistic abilities and feel they are conscientious and practical.

How Do Others See You?

  • Realistic types are described by others as humble, frank, self-reliant, and persistent.
  • Investigative types are described by others as intelligent, introverted, scholarly, and independent.
  • Artistic types are described by others as unusual, disorderly, creative, and sensitive.
  • Social types are described by others as helpful, agreeable, outgoing, and patient.
  • Enterprising types are described by others as energetic, extroverted, shrewd and ambitious.
  • Conventional types are described as careful, rule-oriented, efficient, and orderly.

What Do You Avoid?

  • Realistic types avoid interaction with other people.
  • Investigative types avoid having to persuade others or sell them things.
  • Artistic types avoid routines and rules.
  • Social types avoid mechanical and technical activity.
  • Enterprising types avoid scientific, intellectual, or complicated topics.
  • Conventional types avoid work that does not have clear direction.

Entrepreneurial Work and Creative Individuals

If you are an artist and reading this post, it is quite likely that an A likely appears somewhere in your personality code. However you need to focus most on the letters that come before or after the A.

One of the interesting aspects of entrepreneurial individuals, who are also artistic types, is that they often discover that they have three, four, or even five equally dominant personality traits, just like I do.

I find many who have taken this test to at least 2 equally dominant traits and often 2 secondary dominant traits and sometimes more. This often comes as a huge surprise and can often explain the “tug of war” that can occur inside of us with which of our interests should lead and which should be in supporting roles.

All too often or ability to discern this struggle is further masked by, as artists, our own labeling as ARTIST but nothing more. Hopefully you are beginning to understand how very limiting this kind of silo thinking can be. In fact, having multiple dominant traits is an indication that many creative types have more strengths and a more diverse range of talents to draw on than they ever imagined.

An Exercise to Uncover Where Your Personality and Career Interest Align to Form an Original Entrepreneurial Idea.

Start by writing down your SDS 3 letter code:

My SDS 3 letter code is: ___ ___  ___

Take the first letter of your code and look up in the occupational finder the jobs using exclusively the first letter of your code.  Write down five of these that interest you.  Select items that you think might be fun or interesting or challenging, not jobs you necessarily would ever choose. Any key aspect to the job that is compelling for you is enough to put it on the list.






Now do the same thing for the second letter in your code.






The third letter in your code is likely to be less important in the overall direction of your career but more important when it comes to your surroundings and environment. Use that third letter to again identify five jobs that appeal to you in some way.






Finally, look at each of these 3 lists and put stars by the ones that really interest you and you could seriously consider doing. If you can think of jobs that you might enjoy but aren’t on the list, add them here:

My other creative possibilities include:




Now take a moment and reflect on who you are and describe why your favorite potential opportunities are inline with the core personality traits of your score.

Finally feel free to be creative, and string the occupations you are most interested in together. String as many different combination’s together as possible and write beneath the string which dominant letter you are putting first, second, and third as you do.  Once you have done this,  see if any one string can be sewn together to create a brand new shape to hold your artistry and fuel economic viability.


Is there one particular string you have assembled that truly equals something new you can call your own creation? What makes all of this so challenging is the myriad of options that are available to you that you already have as part of your skill set. This is another reason why you must be careful to match your dominant personality traits to the shape of your entrepreneurial effort until it fits you just right.

The SDS tool and this exercise have served many of my emerging entrepreneurial students well in their entrepreneurial idea discovery process. I hope it serves you in finding an entrepreneurial idea that you are willing to invest your heart and efforts into to build an entrepreneurial life of your very own.

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  • Hi,
    Interesting, I`ll quote it on my site later.

  • Chelsea

    I really appreciated the stories you told to help explain the letters. Great extension and application, too – I’m excited to do the exercises at the end of the post.
    Have you heard of or looked at a book entitled The Career Guide for Creative and Unconventional People by Carol Eikleberry? It is written specifically for the SDS “artistic” types (anyone with an “A” in their three-letter code). It would probably fit quite well with the work you are currently doing.

  • Chelsea,
    I AM familiar with that book and it is very helpful. The tricky part, of course, is learning how to apply what you have learned from both Carol’s book and the SDS. What were your letter codes and are you attending a school with a program that can help you apply it? Doing work you love requires Independence and while it is a choice that you are obviously strong enough to consider, getting there requires experimentation, education and support. Have you considered Every good wish to you!! Thanks for your comment and stay in touch.

  • Heena Virani

    very useful and knowledgeable thank you

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