Why Do So Many Entrepreneurs Hate Their Lives?

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You finally started your own business or private practice. And, now, you’re in hell.


It’s three years in, and things aren’t going as planned.

Growth is slow, you’re spending so much time doing the grunt work and servicing customers, you have no time to focus on the big picture. Growth has stalled. Even if you’re growing, the grind is killing you. Your health and waistline, bahahahahaha. Gave that up long ago. Relationships, oy vey. Joy, done.

You secretly yearn for regular hours and a reliable paycheck, even if it means dealing with an idiot for a boss and purposeless existence.

So, you sit around, looking for a sign from God. And you’re not sure if you want her to tell you to continue, or to walk away. It’s not that you don’t believe there’s still great potential, it’s just that you have no idea how to right the ship and you feel like a prisoner.

I’ve had this conversation with so many entrepreneurs, and shared the cautionary tale with so many aspiring entrepreneurs.

Being your own boss, doesn’t automatically put you on the “yay train.”

So many entrepreneurs unwittingly build their own stress-addled, cash-poor cages, rather than engines of freedom, expression and connection. Not because they’re stupid or incapable, but because they learned how to serve others, but not themselves.

The Cult of the Customer.

The world of entrepreneurship is maniacally customer oriented these days. Identify and develop the customer, we’re told. It’s important, you don’t have a business without a customer. But, guess what…

Without a business that serves as a simultaneous engine not just of revenue and service, but of personal expression, connection, freedom and purpose, you don’t have a life!

Doesn’t matter how much money you make, or how many people you’re serving, every day you go to work will suck. Which means every day will suck, because you will always be working. Never having understood what you really wanted, or how to build something that not only gives the customer what he wants, but also gives you what you need.

While this phenomenon is rampant and growing in the world of startups and bootstrapped entrepreneurs, it’s also rampant in the world of private-practice professionals, creative pros, and even employees.


Entrepreneurship is not about building a great business, it’s about building a great life.

But, you will never get what you want from the way you contribute to the world until you learn how to align your actions with your essence. And you cannot do that until you know who you are.

If your work lights you up, lets you express yourself, tap fiercely into your potential, play with people you love and earn enough to live well in the world, rock on. If not…

Do NOT pass go.

Do NOT suffer onward.

Do NOT keep welding the bars of your cage thicker and thicker.

Hit pause.

Ask yourself:

1. What do I care about?

2. What do I hold sacred, both in business and life?

3. What lights me up, what would I work hard to do for free?

4. What empties me out, emotionally, psychologically and physically?

5. Who do I want to serve?

6. Do I care more about serving or building?

7. What do I value on a non-negotiable level?

8.What am I great at?

9. What am I terrible at?

10. How do I want to spend each day?

11. How do I want to live my life?

This is just the beginning of the inquiry, but if you start with these 11 prompts, you’ll have done vastly more than the average entrepreneur or aspiring entrepreneur or, frankly, even the average human to start to understanding who you are and what you need.

And, you’ll start to cultivate the level of self-knowledge needed to build something that not only makes money and serves a need, but also serves you and the life you seek to create.

Entrepreneurial failure to thrive isn’t just about a lack of money, knowledge or skill, it runs far deeper. With rare exception, it’s deeply rooted in self-ignorance.

Know yourself. Express yourself. Master yourself.

Then, build around that.


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33 responses

33 responses to “Why Do So Many Entrepreneurs Hate Their Lives?”

  1. Giancarlo says:

    I remember reading the Good Life Project Creed. And I was blown away by what really matters most. Oftentimes, we get trapped by the desire of just ticking off things in our list that we forget to enjoy the journey of building a business. I keep looking back at the Creed and started making my own Creed for my travel business. I want to make sure that the business I build is the business is something I can proudly leave as a legacy. 🙂

  2. Darin says:

    startupsanonymous.com has been my go-to when I have to vent frustrations

    it’s also a great resoruce for more depth about the depression and suffrage

  3. Miranda says:

    This is a great post, Jonathan. I think this is one of the stickiest, most dangerous swamps we trek through in life, and completely agree that it’s important to spend the time to get really clear on who you are and let your business/career reflect that. My personal experience, is that I spent almost a decade building a career that I thought was my dream – a creative, fun career that has given me a wealth of wonderful experiences. Because it was a career in the arts, I thought I was following my dreams, but when I found myself less and less happy the more successful I became, I finally realized that my heart didn’t just want to “be an artist”, it had very specific stories to tell. It was not at all interested in my mind’s fear of failure, and it was not going to allow me to waste any more time. When the heart speaks up, it is a demanding force, so it’s better to get clear enough to hear it from the start. Otherwise that transition period when you finally become a good listener can be a real kick in the goose 🙂

  4. Laura Neff says:

    Well, Jonathan, you just summed up my Immersion 2014 experience in such a nice, tidy package! Thank you!

    No, really…THANK YOU. 🙂

    If I’m attempting to succinctly share with someone what I learned in the 2014 Immersion, it often comes out this way: “I learned that it’s not only WHAT you do, but it’s HOW and WITH WHOM you do it. All three have got to be deeply aligned with who you are and what brings you most alive in this life.”

    I know that someday, when I look back, there will be a few shining years that are clear pivot points. 2014 will be one, and it will be because of Immersion and the choices I made because of it and the community of amazing humans it’s brought me to. H*LL. YEAH. Bring on 2015 and all that’s to come!

  5. […] Why Do So Many Entrepreneurs Hate Their Lives? from Jonathan […]

  6. AJ Walton says:

    Hi Jonathan,
    I’ve been here. Entreprising, hustling, only to realize that at the end I’d built myself a job. Only it’s harder, because my paycheck relies solely on me.

    I wouldn’t trade entrepreneurship up for just aboout anything, because as you said, it’s not just about money, but about the creativity and expression and realization of who we are that goes into the process too.

    I’m absolutely horrible at defining my ideal customer. I’ve done all the exercises by this guru and that. Can’t find what fits. But I keep getting better and better at realizing what turns my crank. That’s the path I’m going to be following for now. Long ago learned that if something isn’t working, it’s better to try something new than struggle in futility.

  7. Great stuff here Jonathan and spot on – thanks man! “Entrepreneurship isn’t about building a great business, it’s about building a great life.” I love that I myself have been guilty of not focusing on building that great life in conjunction with a great business in the past. A must needed reminder and wake up call. Thanks again, cheers!

  8. I’m thinking this is a great list of questions to ask ourselves every New Year, Jonathan. That would be pretty revealing… Hey, it’s still January right now. I’m going to take myself through the list today! Thanks for this characteristically succinct little packet of wisdom. Wow, it’s really good.

  9. Sharo Babcock says:

    I’m paying attention to the prompt here “Do you want to serve or build?” What do you see as the implication of making that distinction?

    • Pete Austin says:

      Great question. I struggled with that one also. My instincts are to serve more-so than to build (for selfish reasons). However I ended up realizing that what I really want is to build an entity that serves beyond my personal capacity to serve.

      This (concept) if/when successful, fulfills both desires and also fulfills a desire to do something significant for others beyond personally volunteering.

      What I’m saying is that it doesn’t have to be (strictly) one or the other as long as you find out where your heart is.

      I hope that’s helpful.

  10. Stephen Reed says:

    Hi Jonathan

    Thanks for a great post, it’s very cool when things come along just at the right time, as if they were meant to happen. This post is one of those times.

    I’ve spent so much time in the past, and even now to some extent, trying to find the perfect ‘thing’ for me, to build a business on, to find the ‘thing’ that lights me up. for some people, there are many ‘things’ which kind of makes deciding a whole lost trickier.

    But do you NEED to decide. Be interested in your take on it. Is someone who struggles to pinpoint a passion to give the world a procrastinator, someone who lacks clarity and needs to spend some more time trying to find purpose. Or are they a polymath, someone with perhaps expertise in many areas, who should play on that strength and not try to niche down too hard?

    It’s a dilemma that has plagued me for many many years, and I still get caught up in it, flitting from one thing to another, with all manner of ideas.

    How did you find clarity, after being a lawyer, running a yoga business, to where you are now?

    I love your insights, your podcasts and videos, so inspirational, you are doing something incredible in the world. Thank you


  11. nicholas says:

    thank you JF for bringing some of the less flowery truth about entrepreneurship.

    I come from an entire family of self-employed people who understand very clearly the benefits of receiving a company paycheck. And after 37 years of family gatherings, I don’t think I’ve ever heard any one of the dozen plus self-employed people in this group use the word entrepreneur (they are admittedly all over the age of 55 at this point).

    I have heard them all talk ad nauseam about the big joke of self-employment leading one to believe they are free from bosses and managers when the reality is that self-employed people simply make their work AND their customer their boss (in this case, the one who writes the check usually based on the quality of the work).

    So…the conventional wisdom applies…you best like your bosses (i.e. customers) or you ain’t gonna like your life.

  12. Noga says:

    This is a well written post on a, clearly, well thought out issue. Thank you jonathan

  13. Keena says:

    I thank you so much for this, Jonathan.
    It honestly couldn’t have come at a better time. I am on the verge of either making a go of a new business or sticking with my day job. I had been fretting that my day job doesn’t pay enough and is boring. But now am considering that entrepreneurship may be more than I bargained for, having consumed the purple koolaid of entrepreneurial freedom and glory for so long!
    I know myself well, but I will take the time to answer these questions before I go further.
    Thank you again! You rock! 😀

    • Jonathan Fields says:

      Hey Keena

      I’m a huge fan of entrepreneurship, it’s just really important to go into it with eyes open and with a clear understanding of what you want to give to it and get back from it. 🙂

  14. Rosemary says:

    Very interesting and a brave post. So much is written about the glamour of start up and the dawn of success but is little written about the middle years , when the strain of providing a quality service to a growing customer base begins to tell . So many flounder at this point due to exhaustion and lack of resources to fund growth. I think it’s the hardest part of the business journey when you have responsibilities to staff and customers and the tax man . My business is seven years old successful and very demanding now we have a loyal fan base. When you start up you just have a big dream to inspire you and not so many responsibilities….and of course a growing business requires a very different skill set to start ups . Thanks for your support for those of us no longer basking in the energy of start up joy but treading the steep and rugged pathway of a middle aged business!

  15. […] restoration – to be an engine of “expression, connection, freedom and purpose” as Jonathan Fields puts […]

  16. Gail Gaspar says:

    #6 Do you want to build or serve? Thanks for asking. Resonant for me. I agree that a great business is most meaningful when it integrates the perception of living a great life. Clients are often surprised that these two go together like hand and glove and they don’t need to choose one or the other.

  17. Jack Schur says:

    Great post, Jonathan. Super insightful and right on point. I think I learned a lot this the hard way. Wish I had this knowledge a few years ago! I believe more and more that authenticity is a necessary component of true success — however one may wish to define success.

  18. Ashley says:

    Love. This is exactly what I am taking the time to do right now. I am so grateful I stumbled across this blog in the last year. 🙂

  19. Piper says:

    Great post! Quick thing, “You’re health and waistline” has a typo. “Your health and waistline”, right? I was confused reading it so I thought I’d let you know. 🙂

  20. […] “Why do so many entrepreneurs hate their lives?” is a fantastic article. It’s real, honest, and Jonathan Fields offers great tips at the end of the essay. […]

  21. […] Why do entrepreneurs hate their lives? […]

  22. […] you have the entrepreneurial mindset, read this article by Jonathan Fields, a former practicing lawyer who’s now an author, entrepreneur, and producer of […]

  23. Roger says:

    Jonathan your words resonate on so many levels. It seems so many are jumping on the entrepreneurial galactic ship to launch out into the Boldly Go Where No One Has gone before thinking they will find the excitement, joy, success or whatever new experience civilization ect. and wind up in a self imprisoned cell as you described tormented by aliens that they never new existed, that such the very life out of them leaving them to choke on the dust of their own regret. Have been there and done that. In my experience the journey seems so much more rewarding if we would embrace the right philosophy from the beginning and let the quest be about finding ourselves through the process instead of making the quest about money or achievement. Yes? Would love to have you as a guest on our growing blog. upward & Onward and keep doing the great work you are doing.

  24. Leslie says:

    Just listened to this on your new short format talks which I love btw. This, as often is the case, spoke directly to me so thank you, thank you. One question, could you clarify what you mean by “serving or building”? I’m pretty clear on the serving piece but unsure what you mean by building.

  25. […] started writing this post as I was listening to this short bit by Jonathan Fields . It’s all about the trap mentioned above, asking yourself difficult questions, then moving with […]

  26. Jane Cui says:

    I feel really sad because I yelled at my mom for telling me to “stop working” today.

    I’m stressed out a lot because of the new startup. Sometimes I just want to sleep and not wake up.

    Thanks Jonathan for writing this because I always see entrepreneurs being successful (in interviews and videos that I watch all day) and no one ever talks about the emotional pressures.