Rick, this comprehensive, humorous, insightful, sobering warning of an essay should be required reading for ANYONE contemplating a life as an entrepreneur. (Are you listening, Wharton School of Business?) Ultimately, based on your own words and those of folks in the comments section here, you never really had any choice in the matter. Despite all the disadvantages, the entrepreneurial spirit is in your blood, and, as you say, the very idea of working as a staffer would lead you to the loony bin ... pronto.
So I admire that you plug ahead – very successfully, it's worth noting – despite the clear knowledge that ... it could always be easier. But who wants to play "pretend entrepreneur" by cracking open a Monopoly board or dancing in a veggie garden? Though the sacrifices are significant, and you spell these out with eloquence, you're still your own boss. And that rocks.
Thanks Larry. There are many times I've dreamed of a steady paycheck, but all time I spend working with corporations as a speaker has cured me of any fantasy that that would be a preferable way to spend my days.
I wish everyone was this honest when it comes to this topic. While there are certainly many benefits to being self-employed, I find the perpetual glamourisation of entrepreneurism and its corresponding hustle culture in (social) media wakes unrealistic expectations and desires in many...
Yet, I applaud and admire those who go for it and are successful while/after doing so!
Thanks Stephanie. I think deep down most people want to rise to their best and many intuit that they won't get there without being challenged/tested. The sad part is when it gets turned into a pain-fest, as though suffering in one's work is the goal, usually with cash as the reward, vs pursuing something you love and the suffering being almost incidental as we move past whatever obstacles are between us and the vision.
Nice reflection on the compulsive drive to blaze your own path while at the same time acknowledging that it may be your only choice. It’s great to understand where you are coming from and what drives you. I suspect that the only thing this knowledge changes is acceptance and perhaps quieting a potential inner war with the ‘shoulds’ and just accepting what is. I appreciate that your article gives permission to acknowledge the lunacy of being an entrepreneur.
At the same time as a being a lunatic myself, afflicted the crazy bright ball of possibility, which I can confirm is akin to madness there is not much that I’ve done which I could consider as rewarding. Nor can I think of anything else where the cliches are more true, it is a lot more difficult than anyone tells you, and if you can get away with doing something else, do it.
My acting teacher was the only other professional who ever told me that if there was anything else I could happy doing that I should run from acting as fast as I could. I eventually took her advice on that one, and became a birthday party clown in my early 20's, which led me right into the lifetime jaws of entrepreneurship, which I never could walk away from.
He he, I had the same thought as I hit the publish button Chao. There is so much I LOVE about entrepreneurship, but to your question, I don't think those who are born to be entrepreneurs are easily dissuaded, and yes, it seems to be some sort of hardwiring. What are your thoughts on that question?
Yeah, I think you've nailed it - there are lots that I can learn about entrepreneurship, but it requires a certain personality to actually at some level view all the shit you describe above as fun, and that is more likely to be hardwired.
Self-deprecation works every time. But you've turned it into an art form, Rick. I wish to hell I could be half the loser you are. Something divine about it.
Ha ha, this made me laugh PJ. I keep hearing people say you shouldn't be self-deprecating in your own writing but I find it such a joy and relief to admit out loud what's really going on, for myself, and then glad that others find it relatable. Truth is indeed a heavenly soma.
For years people have tried to convince my husband to start his own publishing company and he instinctively knew all that you are saying. I run (a very small, financially) business that gives me grief in the admin department.
I cannot image doing what you do, Rick. Literally and figuratively, you have so many balls to juggle. What happens when you sneeze???? Fantastic article and as Larry has said, one for the business schools/books!
I think there is a fair amount of delusion that has to be present to pursue running your own business. You have to convince yourself that something so amazing and wonderful is possible that the work involved feels like a reasonable trade-off for the chance of it happening.
"The holy grail of autonomy—that coveted prize of being one’s own boss—gave me complete freedom to decide which 20 hours of each day I’d be working." Brilliant... and that phrase says it all.
OMG... laughing with tears throughout all of this. It's been a wild ride of a life though... one I wouldn't trade in for anything. Still, it feels a tad sad that I too often negate what all it took to keep my boat afloat with 3-4 "part time gigs" while I struggled to call myself an artist. I'm finally ready to share some of those journeys in my writing with pride rather than feeling like I failed somehow. Thanks for this piece Rick.
…what do you see as the main attributes/stories that have tied you to the value system that maintains your “entrepeneuer” mindset?…who or what influenced you to be this way or is nature the maker?…
That's a great set of questions. I watched my dad grade thousands of papers as an academic, heard his stories of the inane posturing in the university that filled every meeting, and watched his talent as an athlete and a closet performer take a backseat. I think I felt determined to do something different with those same interests and make better money in the process and not be handcuffed by a sense of scarcity that my dad had as a teacher. But I was also very scared of visibility and success, and I think pursuing entrepreneurship was a place I felt like I might be able to prove myself, verify I could make it, be successful, or look confident, when my inner experience was anything but. I guess entrepreneurship gave me a sense of control since I was in charge of my own challenges.
I'd ask, "Did you ever try to sell anything to anybody for actual money before the age of eight?" If the answer is yes, you'll probably never escape the entrepreneurial path and you might as well make the best of it.
Wow. Too much truth for one essay! Do you have a license to provide so much dangerous insight? We need an "Unemployable Union" but none of us could agree with each other.
This is the niche of the world of associations, many of them filling this need for entrepreneurs to connect with others like them. As a speaker I've seen just how many of them there are in the world, and it's mind-blowing. There's an association for everything!
This is so hilarious and so accurate. I’m always thinking everything about being an entrepreneur is harder and its own rollercoaster. At yet somehow I have no desire yet to return to the corporate world, even though occasionally I’ll dream about it. There’s something that is pulling me in this direction. So much respect to you for doing it for so long!
Thank you Michelle. It's sort of like parenting. Once you have kids you're in a secret club that nobody without kids really understands what you go through. Once you have your own business you cross a similar threshold and speak a language that others can't really understand, and included in that language is a measure of pride, agency, self-determination, and excitement that's hard to convey.
You said you have been an entrepreneur for 50 years and gave a lot of good reasons not to start. So what prevented you from stopping 10, 20 or 30 years into your journey?
That's a great question Mak. My first gut response is, "Having something to prove." I could make up other answers, but my feeling about it is just that. And I suspect that urge to prove has both a light side and shadow side to it, meaning there's a pure motive around fully becoming who I am meant to be and neurotic drive to try be something in the eyes of others that I won't ever be able to get through the opinion of others.
Rick, this is the most honest description of self-employment that I've ever read. (The freedom to choose which 20 hours a day you want to work ◡̈ ). Becoming an entrepreneur seems to be glorified in our culture right now, but I imagine people would be much more cautious diving in if they knew what it actually entailed. Thank you for presenting such a balanced view.
Also, as a Mom, this was my favorite part ◡̈
"I had packed just one change of clothes for a three-year old on a two-day trip. That was the sort of dad-math my wife would roll her eyes at and correct when we traveled as a family"
Rick you once commented on one of my essays being an origin story. That’s what this feels like down to the bones.
I would however say, you’re pretty darn smart, especially for recognizing this:
“Let me just say that I deeply wish I could not be an entrepreneur but, after 50 years, to sign up to be somebody’s employee would be an act of rapid and gruesome unraveling that no one would benefit from witnessing. I’d be staging a hostile makeover of the organization in my own mind before my first lunch break, cuz that’s what enterprising brains like to do.”
A great question to ask in life is not “what can I do?” It’s what can I not, not do?” I can’t imagine you NOT being an entrepreneur. That you recognize the same thing, says a lot about who you are. 😊
Thank you James. I like the idea of this as an origin story in many ways. The project itself and the book very much encapsulates where I've come from as well as where I intend to be going with this life. But the story of its creation and my resistance to releasing it is a fundamental reminder of what I (and I think many of us) are always up against when it comes to being visible in our essence in the world. "What can I not, not do?" is awesome and gets us to the heart of what's essential real quick. And you're right, doing my own thing for work is truly non-optional. Are you in the same category?
Rick, excellent distinction about creation and resistance. You strike me as one who has maybe known your whole like that the boundaries of a company and the narrowness of a job are too small for you and your essence. I discovered that by my late 30s. And I also discovered I wanted to serve people directly. My journey into entrepreneurship and staring my own business was an outcropping of that discovery.
It’s also funny (or not) that I posed the question of not, not doing. I’m discovering that at almost age 60, and now that I’ve build a firm of heartfelt and caring people that can care for our clients after I’m gone, it’s closing in on my time to not do this vocation any longer. I’m feeling a calling to serve myself with downtown and express myself into the word, to touch hearts in new ways. I cannot, not discover what those new ways are. 🙏❤️
This is the definition of being an honest human. I’m blown away by this essay. Thanks for sharing these poignant thoughts, Rick.
Internal, external, nocturnal. That covers it.
Thanks Kathy. Keep that wonderful day job!
God willing and the creek don’t rise as my rancher fam says.
Well . . . if that happens, you definitely have a paddle.
Rick, this comprehensive, humorous, insightful, sobering warning of an essay should be required reading for ANYONE contemplating a life as an entrepreneur. (Are you listening, Wharton School of Business?) Ultimately, based on your own words and those of folks in the comments section here, you never really had any choice in the matter. Despite all the disadvantages, the entrepreneurial spirit is in your blood, and, as you say, the very idea of working as a staffer would lead you to the loony bin ... pronto.
So I admire that you plug ahead – very successfully, it's worth noting – despite the clear knowledge that ... it could always be easier. But who wants to play "pretend entrepreneur" by cracking open a Monopoly board or dancing in a veggie garden? Though the sacrifices are significant, and you spell these out with eloquence, you're still your own boss. And that rocks.
Well done, as always!
Thanks Larry. There are many times I've dreamed of a steady paycheck, but all time I spend working with corporations as a speaker has cured me of any fantasy that that would be a preferable way to spend my days.
I wish everyone was this honest when it comes to this topic. While there are certainly many benefits to being self-employed, I find the perpetual glamourisation of entrepreneurism and its corresponding hustle culture in (social) media wakes unrealistic expectations and desires in many...
Yet, I applaud and admire those who go for it and are successful while/after doing so!
Thanks Stephanie. I think deep down most people want to rise to their best and many intuit that they won't get there without being challenged/tested. The sad part is when it gets turned into a pain-fest, as though suffering in one's work is the goal, usually with cash as the reward, vs pursuing something you love and the suffering being almost incidental as we move past whatever obstacles are between us and the vision.
Nice reflection on the compulsive drive to blaze your own path while at the same time acknowledging that it may be your only choice. It’s great to understand where you are coming from and what drives you. I suspect that the only thing this knowledge changes is acceptance and perhaps quieting a potential inner war with the ‘shoulds’ and just accepting what is. I appreciate that your article gives permission to acknowledge the lunacy of being an entrepreneur.
At the same time as a being a lunatic myself, afflicted the crazy bright ball of possibility, which I can confirm is akin to madness there is not much that I’ve done which I could consider as rewarding. Nor can I think of anything else where the cliches are more true, it is a lot more difficult than anyone tells you, and if you can get away with doing something else, do it.
My acting teacher was the only other professional who ever told me that if there was anything else I could happy doing that I should run from acting as fast as I could. I eventually took her advice on that one, and became a birthday party clown in my early 20's, which led me right into the lifetime jaws of entrepreneurship, which I never could walk away from.
A strange ode to entrepreneurship! Do you think entrepreneurs are born and not made?
He he, I had the same thought as I hit the publish button Chao. There is so much I LOVE about entrepreneurship, but to your question, I don't think those who are born to be entrepreneurs are easily dissuaded, and yes, it seems to be some sort of hardwiring. What are your thoughts on that question?
Yeah, I think you've nailed it - there are lots that I can learn about entrepreneurship, but it requires a certain personality to actually at some level view all the shit you describe above as fun, and that is more likely to be hardwired.
Yes. It sounds really unpleasant, but even as I was writing it the feeling I have is, I love these difficulties. I guess we're weird.
"... all the shit that [Rick] describes as FUN."
That, right there, Chao, nails the entrepreneurial spirit!!
Self-deprecation works every time. But you've turned it into an art form, Rick. I wish to hell I could be half the loser you are. Something divine about it.
Ha ha, this made me laugh PJ. I keep hearing people say you shouldn't be self-deprecating in your own writing but I find it such a joy and relief to admit out loud what's really going on, for myself, and then glad that others find it relatable. Truth is indeed a heavenly soma.
"I wish to hell I could be half the loser you are."
PJ, that, right there, is a million dollar bumper sticker!
Not sure if it wouldn't get you rear-ended by someone who read it without the context, but I agree, it's a heck of a line.
I'll second Kathy Ayers' sentiments for sure. Honest and human and humorous, let's add. Oh, and skillful, artistic, just right.
Thank you very much Bob.
For years people have tried to convince my husband to start his own publishing company and he instinctively knew all that you are saying. I run (a very small, financially) business that gives me grief in the admin department.
I cannot image doing what you do, Rick. Literally and figuratively, you have so many balls to juggle. What happens when you sneeze???? Fantastic article and as Larry has said, one for the business schools/books!
I think there is a fair amount of delusion that has to be present to pursue running your own business. You have to convince yourself that something so amazing and wonderful is possible that the work involved feels like a reasonable trade-off for the chance of it happening.
Indeed.
"The holy grail of autonomy—that coveted prize of being one’s own boss—gave me complete freedom to decide which 20 hours of each day I’d be working." Brilliant... and that phrase says it all.
ha ha, you'd certainly know Chris.
OMG... laughing with tears throughout all of this. It's been a wild ride of a life though... one I wouldn't trade in for anything. Still, it feels a tad sad that I too often negate what all it took to keep my boat afloat with 3-4 "part time gigs" while I struggled to call myself an artist. I'm finally ready to share some of those journeys in my writing with pride rather than feeling like I failed somehow. Thanks for this piece Rick.
Yay Linda! I'll toast to that! Share the journey!
…what do you see as the main attributes/stories that have tied you to the value system that maintains your “entrepeneuer” mindset?…who or what influenced you to be this way or is nature the maker?…
That's a great set of questions. I watched my dad grade thousands of papers as an academic, heard his stories of the inane posturing in the university that filled every meeting, and watched his talent as an athlete and a closet performer take a backseat. I think I felt determined to do something different with those same interests and make better money in the process and not be handcuffed by a sense of scarcity that my dad had as a teacher. But I was also very scared of visibility and success, and I think pursuing entrepreneurship was a place I felt like I might be able to prove myself, verify I could make it, be successful, or look confident, when my inner experience was anything but. I guess entrepreneurship gave me a sense of control since I was in charge of my own challenges.
…if you were to coach someone to determine their mindset type, what indicators might you point to as “attempt entrepreneurship”?…elsewise?…
How about you? What's the first thing you sold?
…would you be surprised to know my first dozen or so sales were trades?…
No, but I guess it also depends. Trades of what? Are we talking baseball cards, or something more off the beaten path?
…rocks, comics, art, bracelets, books…i might always be lost in limbo…
I'd ask, "Did you ever try to sell anything to anybody for actual money before the age of eight?" If the answer is yes, you'll probably never escape the entrepreneurial path and you might as well make the best of it.
Wow. Too much truth for one essay! Do you have a license to provide so much dangerous insight? We need an "Unemployable Union" but none of us could agree with each other.
This is the niche of the world of associations, many of them filling this need for entrepreneurs to connect with others like them. As a speaker I've seen just how many of them there are in the world, and it's mind-blowing. There's an association for everything!
This is so hilarious and so accurate. I’m always thinking everything about being an entrepreneur is harder and its own rollercoaster. At yet somehow I have no desire yet to return to the corporate world, even though occasionally I’ll dream about it. There’s something that is pulling me in this direction. So much respect to you for doing it for so long!
Thank you Michelle. It's sort of like parenting. Once you have kids you're in a secret club that nobody without kids really understands what you go through. Once you have your own business you cross a similar threshold and speak a language that others can't really understand, and included in that language is a measure of pride, agency, self-determination, and excitement that's hard to convey.
You said you have been an entrepreneur for 50 years and gave a lot of good reasons not to start. So what prevented you from stopping 10, 20 or 30 years into your journey?
That's a great question Mak. My first gut response is, "Having something to prove." I could make up other answers, but my feeling about it is just that. And I suspect that urge to prove has both a light side and shadow side to it, meaning there's a pure motive around fully becoming who I am meant to be and neurotic drive to try be something in the eyes of others that I won't ever be able to get through the opinion of others.
Rick, this is the most honest description of self-employment that I've ever read. (The freedom to choose which 20 hours a day you want to work ◡̈ ). Becoming an entrepreneur seems to be glorified in our culture right now, but I imagine people would be much more cautious diving in if they knew what it actually entailed. Thank you for presenting such a balanced view.
Also, as a Mom, this was my favorite part ◡̈
"I had packed just one change of clothes for a three-year old on a two-day trip. That was the sort of dad-math my wife would roll her eyes at and correct when we traveled as a family"
Rick you once commented on one of my essays being an origin story. That’s what this feels like down to the bones.
I would however say, you’re pretty darn smart, especially for recognizing this:
“Let me just say that I deeply wish I could not be an entrepreneur but, after 50 years, to sign up to be somebody’s employee would be an act of rapid and gruesome unraveling that no one would benefit from witnessing. I’d be staging a hostile makeover of the organization in my own mind before my first lunch break, cuz that’s what enterprising brains like to do.”
A great question to ask in life is not “what can I do?” It’s what can I not, not do?” I can’t imagine you NOT being an entrepreneur. That you recognize the same thing, says a lot about who you are. 😊
Thank you James. I like the idea of this as an origin story in many ways. The project itself and the book very much encapsulates where I've come from as well as where I intend to be going with this life. But the story of its creation and my resistance to releasing it is a fundamental reminder of what I (and I think many of us) are always up against when it comes to being visible in our essence in the world. "What can I not, not do?" is awesome and gets us to the heart of what's essential real quick. And you're right, doing my own thing for work is truly non-optional. Are you in the same category?
Rick, excellent distinction about creation and resistance. You strike me as one who has maybe known your whole like that the boundaries of a company and the narrowness of a job are too small for you and your essence. I discovered that by my late 30s. And I also discovered I wanted to serve people directly. My journey into entrepreneurship and staring my own business was an outcropping of that discovery.
It’s also funny (or not) that I posed the question of not, not doing. I’m discovering that at almost age 60, and now that I’ve build a firm of heartfelt and caring people that can care for our clients after I’m gone, it’s closing in on my time to not do this vocation any longer. I’m feeling a calling to serve myself with downtown and express myself into the word, to touch hearts in new ways. I cannot, not discover what those new ways are. 🙏❤️
I'm very excited that I get to stand right here and watch that discovery process unfold for you James.