Entrepreneurship is a spectrum: Find out where you are

The world of entrepreneurship is typically one of black and white. Magazine covers are full of people who have given up their lives to grow a billion dollar tech company. And the phalanx around those people are the entrepreneurs who want to sell a big company themselves. Which means long hours, huge tradeoffs, and participation in a hard-core boys club.

In that view, entrepreneurship is only for an intrepid few. They are young with no responsibility, or they are rich, with a huge paid or unpaid support system. But I think there is a much more broad way to think about entrepreneurship.

Here are four models for entrepreneurship that no one talks about. See if you find something that’s a good fit for you.

1. Professional sports.
When you think about entrepreneurship it’s important to include ideas beyond the office. Professional athletes run the gamut from loving to be told what to do to loving to work for themselves.

A good example is April Ross, a silver medal winner in Olympic beach volleyball. She was a star on indoor volleyball teams in high school and college. She could have gone on to play indoor volleyball in Europe and then play on the indoor Olympic team for the US. But she said she turned to beach volleyball because she couldn’t stand the highly structured life of indoor volleyball.

Indoor volleyball has six players on the court, and you have to practice constantly together to know where everyone is going to be at every moment. You workout together, you practice together, and you travel together. It’s a regimented life. With beach volleyball, you can workout by yourself and you only have to coordinate with one other person. In beach doubles each team has a coach, but unlike indoor volleyball, the team, rather than the coach, runs the show.

What Ross was really saying is that she chose to be an entrepreneurial professional athlete. There will be no exit. No big sale of the company. But she works for herself, and she makes her own schedule.

2. Freelance work.
Some freelancers run their lives as if they are working for a company. At the other end of the spectrum, some freelancers blend the line between freelancing and entrepreneurship.

For most people, freelancing is a way to get more control over your life. For a wide range of reasons, people don’t want to go into an office every day. If you are booking gig after gig to pay the bills, you are, in effect, running your own business. It’s a lifestyle business that has the goal of creating a stable life. This is the opposite of a tech startup which creates a very unstable life that allows you to play a lottery game with a potentially big exit.

In the freelance world, you could aim for low-paying steady jobs, or you could aim to collect high-budget clients that allow you to hire other people to do the work.

Further down the spectrum would be a freelancer who creates a brand identity for the freelance business and collects high-paying clients. It’s a higher risk game: you need a pool of big clients and they have to be consistent with your brand. But the exit potential emerges if you take that risk: Sapient, for example, is an agency that grew from freelance gigs to a branded company and then to an exit.

3. Outsourcing  your own job.
Cassie works at my new company, Quistic. Her job is sales and she’s a typical sales person in that she’s got a million ideas for how to get people to buy, and she has a million ways she wants me to tweak the product so she can sell it, but she hates doing the detailed, repetitive task of sending email inquiries.

So I check up on her. I say, “Cassie, send me your sales pipeline at the end of the day,” and she says “Okay, yeah,” which I have learned means, “I hate that so much.”

But then one day she said, “Oh. Sure, great. I’ll get that to you right now.”

I got scared.

It turns out that Cassie hired someone to do that part of her job. And all the other parts she hates.

Alex, who works with us, said, “That’s crazy! Aren’t you upset?”

I am not. Cassie is totally entrepreneurial. Before she was working with me, she was taking my course about launching your own business, but she doesn’t have the risk profile to do it on her own. I love that she started a little business inside of our business. She hired someone to do work that held her back from making bigger sales, which is exactly what entrepreneurship is—finding a way to make money that other people are missing.

4. Creative obstinance.
There is a type of person who insists on making movies, writing novels, playing music, or some other of those annoyingly impossible and low-paying dream-boat lives, all of them starving artists. But that’s out of fashion. It’s not fun to starve, and most parents will let you live at home anyway. But maybe most important is that it’s difficult to do good art if you are can’t meet your basic living requirements.

This means that most artists today are also entrepreneurs. Some people are more entrepreneur than artists—Andy Warhol set the standard for this. Today’s version is more like Damien Hirst (pictured up top), who hires forty people to produce paintings of lots of dots that sell for millions of dollars. A good movie about the entrepreneurial nature of art is Exit Through the Gift Shop. It’s breathtaking, actually. You must see this movie if you want to be an art-world entrepreneur.

If you book yourself on music tours you are running your own business. It’s focused on the music, and you probably hate the drudgery of calling people and booking gigs. But you know what? Tech startup founders just want to run with their idea and hate that they have to spend their time calling investors and pitching them.

Writers also are entrepreneurs. It’s unlikely that they will find a publisher that is competent at marketing a book online. So it’s up to writers to figure out how to sell their book. And even if you do sell your book, you’ll probably have to sell something else to support a family.

Ramit Sethi is a great example of how a book author became an entrepreneur. Ramit has built such a robust business that he could probably exit it at some point—that is, it could run just fine without him because he has built such a trusted brand for his information products under the name Iwillteachyoutoberich.

Miranda July is at the other end of the spectrum. Her advertising for her book is phenomenal. This is so fun to watch that that I loved her before I read the book. And I bought the book.  Miranda July is not committed to building a Ramit Sethi type brand. She just wants to write books. But both are entrepreneurs.

So instead of beating yourself up that you are not starting your own company, think about where you fit on the spectrum. Landing on the cover of Fast Company is not the only model. We each have our own capacity for starting something up. And each of us will succeed if we get to our right spot in the spectrum.

29 replies
  1. Tracy
    Tracy says:

    Entrepreneurship as a spectrum – love it – I wish I had high functioning entrepreneurship (like Miranda July so clever and witty!) but will have. to accept my freelancer diagnosis.

  2. Carrie Gallagher
    Carrie Gallagher says:

    This post arrived at just the right moment, so thank you. I started a freelance effort recently that I hope to turn into something sustainable (and quit my day job), but the fear and self-loathing voices are in full force today. Looking forward to the Quistic coaching seminar next week.

  3. Tamara
    Tamara says:

    I love everything about this post! It’s so refreshing to think about being an entrepreneur on a small scale. I struggle with feeling like I should be striving to build a bigger more lucrative business but what I really want to do is work less, love my work more and share with others. Looking at the world a bit differently after reading this!

    • Penelope Trunk
      Penelope Trunk says:

      It actually takes incredible self-discipline for someone who has tons of big ideas to act on a smaller idea in order to preserve their personal live. I don’t think people realize how much easier it is to go as big as you possibly can vs. going to the size that’s right for your life.


  4. Ann Eichenberger
    Ann Eichenberger says:

    Perhaps I am making this up, but it seems that creating your own job has always been looked down upon by the entrepreneurial community; i.e. creating your own job seems to be a second rate activity in their eyes,
    Yet, it would be impossible for me to find a corporate job at my age of 64 and I am also an INTJ. My attitude is so what if I create my own job and part-time jobs for 4-5 people. I can work at my company until I am in my 70’s and do something worthwhile and get paid fairly well for doing it. I would rather being doing this than collecting Social Security as some of my high school friends are.
    No one can ever force me to retire from what I am doing!!!

    • Penelope Trunk
      Penelope Trunk says:

      I agree about the snobbery over creating your own job.

      In the venture capital world, where I find myself pitching a lot, the worst response you can get is “that seems like a lifestyle business to me.”

      I realize now, though, that what that response really means is “that idea will create a good life for you, but it’s not going to make the venture capital firm a lot of money.”

      I need to train myself to focus on hearing the part about “that will be a good life for you”


    • karelys
      karelys says:

      I am not sure I understand what you mean “creating your own job.” Do you mean, working for a company but essentially creating the need in that company for you and get paid for it while you create jobs for other people?

      If that is it, I agree with you.

      Something this blog helped me change my focus on was this sort of thinking. Before I thought that any “job” was like jail and freelancing was, well, freedom. But now I think that both scenarios can be both jail and freedom.

      If you create a job for yourself with flexibility and good pay and they really need you then it can be a lot of freedom. But if you freelance for lots of annoying clients you have a lot of bosses. And LOTS of work that doesn’t necessarily increase pay.

  5. Victoria
    Victoria says:

    Great models for entrepreneurship.Thanks for sharing.Out of these all the “Outsourcing your own job” is the best one for me because it’s a creative way to overcome from the overload.

  6. Anca
    Anca says:

    I just signed up for a (very expensive) course that is geared toward people who want to start a business but haven’t the slightest idea what or how or anything. Being particularly intrepid not required.

  7. Lucy Chen
    Lucy Chen says:

    Now I’m the 4th type, Penelope, having launched my art business in July this year, and after founding a bootstrap with my husband 3.5 years ago :)

  8. Noa
    Noa says:

    Love this.

    Most everything else in the world lies on a continuum (personality characteristics, intelligence, talent, political views, mild-spicy indian food), so why not entrepreneurship?

    • Penelope Trunk
      Penelope Trunk says:

      Now you make me think like I’m playing a game — how to deconstruct my vision of myself by thinking of everything as a continuum. Like, I am not good or bad at time management, not good or bad at social skills. The first thing that happens when I think of everything as a continuum is that I think I can make slight improvements on stuff to move myself toward where I want to be: visual encouragement instead of black-and-white thinking which is visually damning.


      • Noa
        Noa says:

        Oh, that’s totally it. Great performers tend to be focused less on whether they’re good/bad (because if you’re good, then you stop working – and when you’re bad, what’s the point?), and more on how they can get better and move further along whatever continuum they have their eye on.

        I’m sure you remember this from your volleyball days – elite athletes tend to be keenly aware that there’s no standing still, right? You’re either improving your skills in the offseason and getting better, or essentially you’re getting worse, because there are always other younger, hungrier players working hard rising up in the ranks waiting to take your place…

  9. Ali Davies
    Ali Davies says:

    I think the bottom line is that each of us have to decide what sort of life and work best fits our values, our own definition of success and what fits us best. That way we will always be living and working on our own terms.

  10. Tara Sayers Dillard
    Tara Sayers Dillard says:

    Didn’t realize, 30 years ago, I was starting my own business.

    Needed a paycheck, had to design gardens or shrivel & die.

    Wise? Hardly. Family ridicule has remained constant. DNA finds it hard to ignore a parent’s insults.

    Most of my career money was never at the level of my peers.

    Since 2008? Fabulous.

    A garden designer will do well in a bad economy. Who knew?

    Another reason for my success? Infertility. Time to work weekends, do lectures any evening of the week, blah-blah. Friends close to me tease about my quirkiness. They know it has been a hard, but happy, road.

    And my work creates jobs for a team of men. Most with young children. All because my soul will shrivel if I can’t design gardens.

    Thanks for the direct answers during the webinar Penelope. And honesty.

    Garden & Be Well, XO Tara

  11. Cathy Goodwin
    Cathy Goodwin says:

    One of the best posts I’ve seen on this blog. These days, self-employment of some kind is the best job insurance, and there’s no rulebook about how you do it.

    Re outsourcing your job, you’d have to check on your company’s policies, but an awful lot of senior executives do this on the QT. I know lots of top guys whose wives edit their reports, so why not pay someone to do it?

    Re artists – I know a ceramic sculpture artist – very talented recent grad of a BFA program – who made a decision she would do her art and earn a good living. She combines teaching with marketing aggressively (but politely) to galleries, writes proposals for commissions and volunteers for community responsibility. She also seeks out successful artists and asks their advice. She’s already getting a national reputation and a savings account. It can be done!

    • Penelope Trunk
      Penelope Trunk says:

      You’re right about executives. It’s such an easy way to make it look like you are capable of more than anyone else: hire someone to do part of your job. If you don’t tell anyone you look like a superhero. The first time I met someone who did this it was someone making mid-six figures at Dell.


  12. Michael Feeley
    Michael Feeley says:

    Good article.

    I especially like the person who hired someone to help her do the things she hates. So smart!

    Why waste your time doing things you don’t like when you can barter with someone or simply hire someone so you can do what you love, what you are really good and successful and creative at.

    Don’t get pain go after success and be being happy instead of bogged down and held back.

  13. Larry Hochman
    Larry Hochman says:

    How magnificent is this! Giving ourselves the emotional permission to be the kind of entrepreneur we are, and not having to feel badly for the kind we aren’t! In the home business and Internet marketing worlds, where much of my background is, there is such a pecking order based on performance of tasks and achievement. It knocks a lot of people out of the ballgame because they don’t want to feel incompetent. In reality…it’s our lives. As you said, that’s one of the major draws of entrepreneurship. Terrific post, Penelope!

  14. Gary Sarratt
    Gary Sarratt says:

    I’m no entrepreneur, but it seems to me, in order to be successful at it, a great approach would be to use Maslow’s Hierarchy of Needs.

    To sell a good or service to someone, you must convince a given demographic that it fulfills a need (real or imagined; fleeting, silly desires often fill the bill, even if self-destructive). The needs on Maslow’s pyramid never change, but the answers to them are ever-evolving.

    It makes sense, then, to try to spot a way to scratch tomorrow’s itch before the other guy does. Cardiac and renal diets, for example, are skyrocketing, but low sodium food products are in short supply. Salt substitutes are off limits because they are loaded with potassium, at levels dangerous to cardiac or renal disorder sufferers. Find and market a salt substitute without that baggage, and you’ll have it made.

    That is just one example; there are many demographics out there, each with its own particular set of future needs. Learn Maslow and be happy, in any pursuit of life.

  15. Coach Oz
    Coach Oz says:

    Point 3 scares me a bit. First companies outsources all their jobs to India and soon employees start outsourcing all their assignments that they don’t want to do to India as well.

    Coach Oz

  16. Jeanine
    Jeanine says:

    With so much to do for any small entrepreneurial business today, I find that the only way to survive is to outsource…especially the things I’m not particularly good at.

  17. L'Tisha Walker
    L'Tisha Walker says:

    I’m so glad a friend turned me on to your blog! I’ve had a blog of my own for about a year and I started it intending to generate income from home, but I’ve really had trouble convincing myself that this is my BUSINESS and not just a hobby. My intentions and my actions just weren’t lining up. This post really helps me understand the mental jump I need to make to get to work for real. I’ll definitely be back to read more!

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