The Myth of Freedom and Entrepreneurship

Scroll down ↓

Ask new and aspiring entrepreneurs what draws them to the quest to start their own businesses and you’ll often hear “freedom” in reply. Control over when you work, who you serve, how you decide and what you create.

Ask established business owners what the best thing about the way they earn their living is and freedom rarely every tops the list. Because, they’ve been in it long enough for the illusion to drop away and reality to set it.

Artists who create art for art’s sake devoid of any need for others to exchange money for what they create may well have freedom, provided they have other ways to earn a living or what they create just happens to tap into an existing need, zeitgeist or delight on a level others value enough to pay for.

Entrepreneurs, on the other hand, can and should create art on every level, from culture-building to customer service and product development. But the moment you ask for money in exchange for what you create, you lose a piece of freedom.

Because the market, your customer, decides whether what you’ve created is valuable enough for you to keep doing more of it. Not you. Them. They are your boss. Always have been. Always will be.

The real difference between doing it yourself or working for “the man” is not that you have the freedom to now call all the shots. You don’t. It’s that you get to remove the layers of people, institutions and processes that interfere with your ability to communicate with and more directly serve the one person who’ll always have ultimate control over your freedom. The customer.

Put another way, it’s about whether you get to work directly with the person who holds the reigns or serve under tens, hundreds or thousands who hold their own sets of intervening reigns, each with their own agendas.

There is huge benefit to removing all those layers and speaking directly to the people you serve. But, always remember, the moment you rely on other peoples’ willingness to exchange money for what you create in order to live well in the world, that’s the moment freedom cedes.

You serve.

That’s not a bad thing. But it’s a thing. One most aspiring and new entrepreneurs struggle mightily with.

True entrepreneurs are driven to serve as much as they are called to lead. Click to tweet

If you want to be an entrepreneur, the sooner you own that, the better.

In the comments below, share your thoughts…

Join our Email List for Weekly Updates

And join this amazing community of makers and doers. You know you wanna...

50 responses

50 responses to “The Myth of Freedom and Entrepreneurship”

  1. Amar Rama says:

    Well said and thank you. Truth is often direct and simple. Often times that combination does not sit well with people like me who don’t like the answer ;-).

    Also worth exploring is a simple list of plus and minuses of the two paths. Especially now that entrepreneurship is the new black and romanticized almost exclusively along the get rich young axis. It is a choice and a life style and carries with it all the consequences of a life style/worldview.

    p.s I just started reading my copy of “Uncertainty”. Looking forward to it 🙂

  2. Candice says:

    This truth was something I had the good fortune to see as I grew up. My grandfather owned a store/diner for many years (alongside a full-time job), my mother had her own law practice for a period of time, a couple of uncles had their own big rigs, and several other relatives had (very) small businesses.

    My grandfather made his store central to the community by serving his customers in a way that kept them coming back. It was clear to all of us that without them there would be no store, and we were to treat them accordingly. My books are no different than the cheeseburgers we grilled in the store kitchen.

  3. I’ve worked for myself for nearly 7 years (this time around.) It started because I needed the freedom to work from home and care for my wife, who was recovering from a serious illness.

    It continued because I love the freedom of choosing what I do, when I do it, and who I do it for.

    I still have all that, and freedom is still my greatest reason for self-employment.

    • I agree to a point, and like others who have replied, I still feel a sense of freedom within my responsibility to providing a meaningful service. Working for others, I have not been as free to explore my own gifts to their fullest. Within the context of my business, I can explore my service fully, expand my capabilities, push myself to do more without a feeling of having as much of a glass ceiling.

      Ultimately, the term I use instead of freedom is sovereignty. What appeals most is the ability to have sovereignty over my gifts, my expression, and my service. Yes, the customer ultimately decides if they are willing to pay for the services I offer, and there are some limitations imposed. However, they are drastically reduced in comparison to my employed life.

      And I am lucky enough that the things that I do enjoy, and the ways I prefer to do those things, generally resonate strongly with my clientele. I feel very free and authentic within my own business, and even the act of collaborating the client frees me in new ways. Perhaps it is more the nature of the one on one business I run, with rich client relationships with people who are on my frequency, that gives it this sense of openness.

      But, to your own point, once I did really recognize that freedom was not exactly what I originally thought it to be, and that I did have to learn to get comfortable with being of service and having responsibility (or response-ability… having the ability, the necessary gifts and resources to be able to respond to the needs of others), then I was able to tap more fully into the real strength of my business and understand the true nature of the freedom I possessed. It was not quite as free as I thought, but it was a better sort of freedom in the end. After all, there is great joy in being of service in a soul-fulfilling way, and that is a sort of freedom all its own.

      • Love the distinction between freedom and sovereignty!

      • I’m not sure I understand your disconnect between freedom and being of service.

        I assume we all know that there’s no such thing as absolute freedom. But when I’m doing work I love, in a manner I enjoy, for people I like, and making a decent living, and giving up nothing (except a larger income) then I don’t see any conflict between my freedom and my service to my clientele. Giving to them has zero negative effect on my freedom.

  4. Eva Papp says:

    Wow this is such a layered post. There’s such an inherent tension between serving (thinking of others’ needs) and being free (not having to think about others’ needs). I think those of us who’s work is also our service are always tight-roping this one. Thanks for bringing it up.

  5. Stevie says:

    Right on, Jonathan! Removing the layers to serve and making a profit for your efforts…that has certainly been the initial challenge from my experience. A delicate balancing act to be sure and one of the first mindsets a entrepreneur on the path to success must master.

  6. Lisa Fabrega says:

    Great, Great article Jonathan!
    I think that the balance between serving/leading others
    and having time in our personal lives is an art form in and of itself too!
    Love the focus on serving & leading–as we serve we lead and as we lead we serve!

  7. Paul says:

    A great quote a consulting friend on mine once told me.

    “The difference between working for yourself and working for others is the difference between having the lillusion of freedom and the illusion of security. “

  8. Jen says:

    Funnily enough this was something that hit me as soon as I walked away from the cubicle and tried the business thing.

    Its the Freedom I walked for, and now I accept a level of financial peril and odd-job rather than creating a sustainable business. I’m truly inspired by Chris Guillebeau’s example, creating a means of generating an income that funds doing exactly what he wants to do…

  9. Jonathan, I think you are absolutely right. If new entrepreneurs define “freedom” as doing what they want, when they want. That scenario doesn’t exist. There is accountability to those we serve. We have to come up with things that fill a need, add value to peoples’ lives, deliver what we promise, etc.

    I’ve been an entrepreneur for over 10 years. I’ve always thought that one of the most important skills I’ve learned is to flourish within constraints. Money tight? Learn how to attract clients inexpensively. Time tight? Learn how to build a team and delegate.

    To me, freedom means making the most of my creative options when my back is against the wall. None of us are ever 100% “free” but through entrepreneurship we can see what we are really make of. Nothing in my long corporate experience exposed me to the kind of risk that allows for huge personal growth (because those layers between us and the customers insulates us.)

    Freedom (to me) is more about being in a position where I’m best able to use all my skills and determine my destiny – as opposed to having to spend my time on producing yet another useless report for some layer of management.

    But yeah, any newcomer to self-employment should know that picking our work hours still means we are going to be putting in those hours. And taking a laptop to the beach might be prettier scenery than a cubicle, but it’s still about listening and responding to those we serve.

  10. Sarah Kent says:


    Freedom for me is an inside job like security or confidence. Being able to choose how i value who i serve and how I serve and how far i go in order to reach the point where an equal exchange of value can occur seems to allow me to more easily experience it more often.
    There are alway’s limitations and barriers along the way its being able to choose how to see them or how to deal with them that is the main difference than being in employment.

    I do things, some i get paid for with money some the rewards are more intrinsic.

  11. Everybody starts a business looking for freedom, all kinds of freedom you can imagine. I lost my job during the meltdown, the company I had worked for ten years just folded up. Sometimes fate can play its hand, two months later my grandmother broke her hip and my grandfather who is almost legally blind couldn’t do enough to help.

    Since I was unemployed at that moment, my lease was up in one month and they needed help with daily chores. So I moved in to help them, two years after that I started my own business. It serves two purposes, allows me to help them when needed and keeps me busy the rest of the time.

    I owe them much more than they ever will owe me, sometimes things just fall into place for a reason.

    • Franck says:

      I agree with you. You listened to your guts and your love for your grand parents, and they guided you well. I believe we all have amazing capabilities to find ways to rebound. But it takes courage as fear is always in the way.

  12. Kelly says:

    If your definition of freedom is not having to really work, or only working when you want to, then I agree you’ve got a rude awakening as a new entrepreneur. For me, it’s about the freedom to do things right. The corporate environment is full of hypocrisy, politics, and bad decisions just because someone is on a power trip. I want to build an environment where my customers are valued, employees are rewarded for their actual contributions (not for sitting at a desk) and decisions are thought out, not arbitrarily made because someone “says so”. Will it ever be a panacea? No. There is no one to pass the buck to when things get difficult. But I value that freedom more than I hate the bad parts.

  13. Marilyn Taillon says:

    My friend Robin Donnan put things in perspective for me when I was contracting:
    “The self-employed have the illusion of freedom.
    The employed have the illusion of security.”

  14. Susan says:

    I guess the truth falls somewhere in the middle. There’s no “absolute” freedom in self employment/entrepreneurship. I’ve been a self employed artist for 20 years and I was fortunate enough to find stores who loved what I did (painted furniture) and were willing to buy it outright. I felt “free” to be doing what I loved. I transitioned into painting art for the walls and again found the same success. However, there came a time when I grew as an artist and wanted to paint abstracts and themes other than “roses” which is what I was most known for. The stores weren’t interested. I had outgrown my current market and didn’t have customers for my new art. I was miserable. With no savings, I decided to give up my rented home and for the last 3 years, I’ve moved around living with my Uncle for a few months, house sitting here and there, and caregiving full-time for an elderly woman for the last year. Through all of this I have been painting what I love, and to my delight I’ve picked up an awesome licensing deal which will more than triple my income. This will allow me the freedom to paint what I love…Isn’t that cool? I think so 🙂

    • Debi says:

      Kudos to you for making the transition you have made with your art. Like you I became known for my poppy paintings and tired after much success of what felt like producing poppies…I am just to the point of simplifying my life to deeply align with my values (an ongoing process as I went from lawyer to artist 15 years ago) and am in the space of a job that is really fun, uses my talents and creativity and a break from painting to produce a living.

      As an entrepreneur and someone who has had many years in the business world, the key for me is doing what I love. Freedom is an inside job and there are trade-offs to each side. The key for me is finding balance in life and I am just deeply grateful for the opportunities my life provides for me to grow and express myself being of service to others.

  15. Maris Olsen says:

    Lovely post Jonathan – thank you. Large corporations started by serving their customers, but many have lost the focus along the way. As a single entrepreneur (aka “without layers”) it is much harder to lose that focus, and of course, doing has a more immediate risk/impact to your bottom line.

    I started a business several years ago teaching people to sew, after most of my adult life in hi-tech. Sewing is a lost art form, and I view my role with my students as an onion-peeler. 😉 I help them remove obstacles to creation. I help them remove obstacles to operating a complex piece of equipment. I help them transform the “I can’t” to “I can”. And that is BOTH freeing and serving.

    Thanks again Jonathan – I hope to see you again at WDS 2013!


    • Jonathan Fields says:

      Love the idea of exploring how to move larger corporations back into the mind and value set that got them where they are in the first place. It’s a part of the work I do on a regular basis these days. Possible, but a real challenge for sure.

  16. The page on my bulletin board is titled “A Fool’s Paradise”. I wrote it and the bullet points that follow were written when I was working in HR in a technology company – probably at least 10 years ago. Here they are:

    – sleeping according to being tired
    – eating when hungry
    – creating beauty in the world
    – supporting myself financially doing work I loved
    – setting a schedule that I want to follow – not one dictated for me

    I came across that page about 3 years ago when I was purging stuff from my corporate life. I had been fired by a CEO for challenging him on his callousness and cowardice for the way he managed his team and the employees in general. I was fried, exhausted and disgusted and could not imagine committing myself to another HR leadership role.

    When I found the page it was like getting hit by lightening – I had known for so long that I wanted to create my own path but had denied myself based on fear, comfort, should’s, (false) sense of security.

    The phrasing isn’t perfect and there’s a bit of victim tone in the points that I don’t like to own but in essence it captured what my heart & soul wanted, needed.

    So now I am building a business at the intersection of my talents and my customers desires. I am making mistakes and fighting resistance and celebrating successes.

    How I correlate this to Jonathan’s post is that I understand that it is only in serving my customers that I will be able to create my “Fool’s Paradise” AND I get to design how I do it. When I procrastinate and have to pull a really long shift in the studio then that’s what I do. When I make the judgement that I can take an hour to watch clouds go by that’s what I do.

    Theresa’s distinction above between sovereignty and freedom resonated with me – it’s like I heard a bell going ding-ding-ding, lol.

    Hmm, a bit of a ramble here – thank you for indulging me 🙂

  17. Elle says:

    It totally isn’t freedom that is the draw for me. It IS serving!! Serving is a beautiful way to fulfill a calling. If you are an entrepreneur, you are in it for who you are there to help. What you get out of it (the freedom part) is just a bonus!

  18. This is one of the things they really need to teach during business degrees or in small business associations. New entrepreneurs need to know that we do what we do to serve other people and that freedom is not something attainable through this course of action.

    However, having the freedom to serve is what entrepreneurship is all about. We serve. Plain and simple.

  19. Stanley Lee says:

    I take the difference would be working for the man vs. for the men.

  20. Absolutely loved this Jonathan and you’ve really hit the nail on the head. I’ve been heading down this path of thinking for the last 6-9 months but only really gained clarity on it recently, and reading your post helped solidify that.

    For me it comes down to no more bureaucracy, office politics or working on projects that have no purpose.

    I’m fully content to work for others, just so long as it’s on things that matter to them and me. That truly is where the freedom aspect comes in for me.

    The day that I get paid to travel for doing nothing but travel will be the day I know I’ve hit the jackpot, but that would be very selfish and unhelpful I think to those I’m serving.


  21. BZTAT says:

    “Artists who create art for art’s sake devoid of any need for others to exchange money for what they create may well have freedom, provided they have other ways to earn a living or what they create just happens to tap into an existing need, zeitgeist or delight on a level others value enough to pay for.”

    This seems like an uncharacteristically black and white statement for you, Jonathan. I think there are more shades of gray, and a whole rainbow of colors here.

    Although I agree that artists, and entrapreneurs for that matter, have limits to their freedom, and that money certainly changes the equation, there are more layers of artistic challenge as well.

    Talented artists find ways to tap into “existing needs” and expanding their audience’s vision with innovation. They accept the challenge of “serving” by taking others to a new level. Art for art sake is a fiction, if you ask me. It is for immature people who cannot accept the challenge of taking their work to a new level, or articulate their vision in a way that resonates.

    Monetary exchange for my art pushes me in new directions and challenges my creativity on many more levels. Just like it did Rembrandt, DaVinci, Warhol and Jobs, and most of the other greats throughout history.

    Being an artist and entrapreneur certainly limits some freedoms, but it also opens new avenues of creativity.

    • Jonathan Fields says:

      Hey BZTAT – Great addition. I think we’re actually agreeing, though, when you take that excerpt in the context of the entire post. 🙂

      • BZTAT says:

        Indeed, I think we agree more than disagree. I just felt a bit more illumination was needed. To many artists, it is an either or situation – you either paint with no intent to sell, or you are a sell out. I think that is a foolish way to look at it.

        You cannot ignore that money changes things, but it does not mean your creativity must be subservient to it. It simply means that you need to take a mature and pragmatic approach to things. Acceptance of existing conditions is just dealing with reality. It does not have to curtail creativity.

        Artists are a difficult lot. I can’t tell you how many say they create solely for “art’s sake” then whine about the fact that no one buys it.

        • Jonathan Fields says:

          Yup, completely agree. In fact, I wrote a bunch about exactly that in my last book.

  22. beth says:

    Years ago someone taught me that there is always a customer.

    Whether you are working for a private firm, a government entity, or yourself. Even if you are so far removed from the “end” customer that you can not relate to him or her, there is always a customer. It may be that your customer, if for example, you work for a governmental agency, is the engineer you do environmental evaluations for as well as the general public that agency serves. Even so, you have a customer and your job is to provide them value, meet their needs, and provide quality work.

    I took that lesson to heart and I always try to find my first-in-line customer to make sure they have what they need at a high level of quality. I do this whether I have a “job” or whether I am creating the job.

  23. Jonathan Fields says:

    Great conversation, as always, gang. Fascinating to see how people experience and define the word freedom in very different, nuanced ways.

  24. Great article. Reality. Truth. Freedom in a sense, but not the one a person begins thinking they’ll have.
    Creative freedom. Free to communicate. Freedom to serve whom I choose. Freedom to choose my hours.
    It all comes back to service… I’m blessed.

  25. Brad Fennell says:

    So true and well said. I have have felt this my last 15 years of being self employed. Initially I thought it was all about the freedom, now I know it is all about the service and the reduction in boundaries to get my work out there. Thanks for writing.

  26. Shyaam says:

    Great article as always Jonathan!

    I feel I got this early on – we are there only because of the customers and only if we can provide true value – the business can flourish!

    But now, I get that I am no in a position to provide value to anyone – so I need to wait and be in purpose before I start my entrepreneurship journey!

    Thank You for the articles and Good Life Project 🙂

  27. […] It’s HARD work building businesses from scratch. Don’t let anyone fool you with the lure that working for, or creating a startup of your own is “freedom” and “work-life balance”. It is, depending on your perspective and lifestyle preferences, but not quite so glamorous as it would sound or appear. (For a great post on this subject, check out Jonathan Field’s blog.) […]

  28. I’m an entrepreneur and have been for many years. And I’ve been, and still am, many types: consultant, manufacturer, distributor etc. And I agree, as all of these (and particularly my consulting) the one paying for your services calls the shots.

    So freedom is indeed a myth except in two important ways.

    1. Its about mental freedom. I am serving and being dictated to by the paying customer, but at my discretion. Sure, if I decide not to cater then I lose the income – but there is a mental freedom of choice.

    2. I can serve on my own terms. I can cater only to that segment of a market who wants what I provide (in the way I am prepared to provide it). Just as Tim Ferris does, I can decide to fire clients, buck the norm, and set new trends.

    Its not freedom in that way people embarking on entrepreneurship expect, that is a myth, but its still freedom of a sort and absolutely worth it.

    • “Its not freedom in that way people embarking on entrepreneurship expect”

      I’ve clearly missed something, Richard. You’ve listed the two most important freedoms of self-employment. If that’s not the freedom people expect when they jump in, what *are* they expecting?

  29. I’ve been a business owner since 2000. Being able to *more freely* choose whom and how I serve is liberating. Feels a bit like wearing shoes that fit versus shoes that are too small – every day.

  30. Lori says:

    while i agree about serving, freedom was and still is the main reason i embrace the entrepreneurial lifestyle.

    clients and customers are not the same thing as a boss. do you have to make them happy? some of them, if you want to stay in business. do you have to make *all* of them happy? no. you have the freedom to define what you’re about and what you do.

    did i work 100 hours a week for awhile? yes. but i could still take a break when i wanted to. i wasn’t on anyone’s clock but my own.

    “the moment you rely on other peoples’ willingness to exchange money for what you create in order to live well in the world, that’s the moment freedom cedes.” — i respectfully disagree. it is a negotiated partnership. they want something; you want to offer something. success happens if you find enough people who want what you want to give. but you don’t have to give up your freedom or control.

  31. y0mbo says:

    There is a great difference between serving and slavery.

  32. “Freedom’s just another word for nothing left to lose…”

    I packed up my life and solo-traveled across three continents because I wanted freedom. I quickly found that part of being free from responsibility was being disconnected from what mattered to me, which was lonely and empty and not what I wanted at all. I hadn’t anticipated that…

  33. jill goldman says:

    This is a very timely discussion for me, since I’ve been wondering about freedom versus service lately for my own business, and how I want to handle it. And what I’ve come up with is that you don’t lose freedom when you ask for money from a customer, but it’s about whether what you’re putting out, based on the freedom of what you’re creating, resonates or connects with the customer, and if it does, then they’ll pay you for what you’ve created and there’s no loss of freedom there. Thank you Jonathan, for getting this discussion rolling. I am enjoying everyone’s perspectives.

  34. It’s interesting to see the dichotomies here. The point of this post (which I agree with in a sense) is that freedom and entrepreneurship are mutually exclusive. But what I see really sparked the conversation here are everyone’s subjective opinions about what “freedom” means to them. Some see being of service and freedom as distinct while others see them as indistinguishable.

    I resonate with both perspectives, in the sense that I can see where both sides are coming from.

    Being of service is very freeing, especially when doing work you love for people who love your work. Plus, many entrepreneurs selling certain services can turn down customers who aren’t ideal (ideally, they have enough demand for their service to be able to do so) so I see that as a very freeing and liberating aspect of entrepreneurship.

    But if it’s time freedom that you seek, or the choice of taking huge swaths of time off for vacations, then I agree with your point Jonathan – it’s likely you won’t be working a 40-hour week anytime soon after starting into business on your own. However, location freedom is a perk of any type of online endeavour. Gimme high-speed wifi and a lap top and I’m in business wherever in the world I decide to plant my butt!

    I really enjoyed this post! It shared an insightful point, and got people engaged. Mission accomplished Jonathan 🙂

  35. Michael Max says:

    It always helps when you have skin in the game.

  36. […] But then I saw this post by Jonathon Fields. […]

  37. Great post, and very true. I have been an enterpreneur for six months now, and the work is finally starting to pay off. However: Freedom to choose your worktimes essentially means you work all the time, either on assignments or promoting your business. Nine to five can become nine to nine easily, so its essential to find time for relaxation, social life and sports to balance out.

  38. […] result of their genuine love of serving people. I did a little google search on Fields and found an article he wrote on the topic. We so often get things topsy turvy in life – as dream chasers we want […]

  39. Matthew says:

    As an entrepreneur, I agree that I am driven to serve and as a creator of something, I am a leader. But this is not divorced from freedom. In my experience I have found that when I have created out of my own freedom something that others value enough to exchange money for, then I am serving a particular market and I am completely free in the creative process of bringing something to that market.

    Yes those customers may ask for certain things in order for them to want to exchange money for it. But it’s always our choice what we do and what path our creation takes.

    I have certainly experienced my freedom being impinged upon in the process of creating something, bringing it to market and needing to make a living and I certainly see the potential of living that way.

    But I’ve found creating somthing in complete freedom, and bringing my passion and inspiration to the table, is always about sharing that creation with others (serving a particular market), and there always seems to be people out there who love it. And this isn’t unique to me.

    The moral of this story is; if freedom is what matters to you then don’t compromise it in your creative endeavours. There will be someoine out there who will be touched and moved by what you create, and will be willing to exchange money for it as a measure of their value for what you do. And this is what service and leadership is all about.

  40. […] of their genuine love of serving people. I did a little google search on Fields and found an article he wrote on the topic. We so often get things topsy turvy in life – as dream chasers we want […]