One of the highlights of my mentoring work with entrepreneurs is the day they decide they don’t want to be entrepreneurs anymore. That might seem counterproductive, of course, but it’s a decision that can enrich the rest of their lives.
Social media sites, especially sites like LinkedIn, are filled with odes to entrepreneurs who tirelessly battle the naysayers and emerge victorious in their crusade for success. Start-up founders are exhorted repeatedly: Never give up, never lose your drive, never accept that it can’t be done, never surrender your dream. Never never never. Ever.
You can, um, pivot, 500 times, but pivoting is for pioneers and exiting is for losers. If you take a different path, you’re a quitter, doomed to be a drone in a corporate world, a follower, a lackey. You’ll be thinking inside the box, wrapped in a corporate cocoon, a drone, a minion, tortured by un-shifted paradigms and un-pushed envelopes. Simply stated, you’re a failure.
Entrepreneurship has become a religion in the business world, with all the zealotry that drives true believers. The entrepreneur is Erik the Red, Chuck Yeager, Davy Crockett (before that Alamo unpleasantness), Thomas Edison and Louis Pasteur…the superhero who will lead us into the future. Or maybe entrepreneurship isn't a real religion; perhaps it's more of a cult.
Entrepreneurship, like bungee jumping and fourth marriages, is an irrational act. The hours are intolerable, the odds for success are abysmal, financial strains are constant, and social/family ties atrophy. Most people who take this path are unbalanced. That doesn’t mean they’re mentally ill, although I do have my suspicions about several, but they often live outside the norms for factors like risk tolerance and ego.
Frequently, I’ll meet a younger person who is swept up in the mania surrounding entrepreneurship. She wants to be a part of the creative process, the disruption, the new frontier for business. She has an idea, usually an app, and she’s ready to change the world.
When it’s a person I’m mentoring, we examine the full range of issues connected to the adventure—and to the adventurer. What will it take to make this a viable business? How can the process be systematized or accelerated? How can cash be charred instead of burned? What are the options for timing and structure of an exit?
The most critical conversation in all of this is about the trade-offs inherent in starting a business. The owner will be foregoing the opportunity to advance in a traditional career in order to roll the dice at an all-or-nothing table. Often, the owner will be taking on loans to finance the first steps of the venture, delaying by years or decades their opportunities for financial security. Almost always, their bucket lists grow dramatically with everyday goals like travel, family, home ownership or binge watching.
Sometimes, the owners make a rational assessment of the situation and decide to move forward. Sometimes, they make a rational assessment of the situation and decide to end the venture.
Maybe they determine that the business won’t be profitable enough to justify the investment or that they will have too low an equity stake by the time they get to the finish line. Maybe they look at their own parents’ relationships, or availability to them as children, and decide that’s where they will make their biggest investment of blood and toil.
Whatever path they choose, they’ll have a solid foundation for their decision and an improved likelihood of success. They won’t quit. They’ll make a decision about the value to be received for the value invested, and then they’ll choose their next steps.
Meanwhile, online, there’s a bro culture surrounding entrepreneurship. Guys post about how hard they work or how little sleep they get or the trails they are blazing, and I can’t help but wonder if they are trying to convince themselves that they deserve a seat with the cool kids. It’s reminiscent of high school, at times, and I hope they grow out of it.
There are many paths to success, many ways to change the world, and many ways to have a fulfilling life. When someone I am mentoring makes an informed choice about the right path, it’s a glorious day.
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Thank you for contacting our customer support center, although we wish you would have followed our suggestions—27 times in the 40 minutes you were on hold—that you visit our website instead. Frankly, we’re impressed by people like you who stay on the line while we bombard you with reminders that you could hang up the phone and get all the information you need online. If we ever get into a staring contest, we want you on our team.
Let us remind you, yet again, that you could go to the Frequently Asked Questions tab on our website to obtain information about how to get to our website, the products we sell, and how to make us your home page. We cannot imagine that there was any reason for you to call our support center, if only you had scoured all 2,788 pages of our newly revised, more user-friendly online presence.
But you didn’t do that, did you? No, you called customer support and spoke with Agnes, so now we need to follow up and find out how well she met your needs, which are very important to us and certainly could have been met if you had gone to our website.
Please note that Agnes might have pleaded with you to give her a 10 rating in every category, if we should happen to ask. She might have wept a bit, as well, suggesting to you that she would be fired on the spot if you gave her anything less than a 10 on anything.
You might have thought she was exaggerating. She wasn’t. We demand perfection in our organization and we expect people like Agnes to deliver that perfection 120% of the time.
Agnes is the sole support of her mother, aunt, and three children, and she needs to work three jobs to make ends meet, because we contracted for her through an outsourced staffing firm that provides no benefits. But don’t let that sway you in your assessment of her performance when you called (instead of visiting our website). Please answer the following questions to let us know what you think of Agnes:
Thanks for your responses to our survey. We appreciate your business and look forward to engaging with you in the future.
But only contact us on our website, not by phone. Agnes’s replacement can’t handle the pressure.
When I told my nephew that Jill and I were looking into leasing an Acura, he commented:
“That’s a good car. It’s a Honda.”
When I told the Audi dealer we were also looking at Acuras, he commented:
“That’s a good car. It’s a Honda.”
It might not be clear from reading these identical quotes that the two comments meant very different things. From my nephew, it was an affirmation. From the car dealer, it was a putdown.
On the screen or on a sheet of paper, you could read those quotes a hundred times and never see the difference. Unless you were physically present, listening to the tone of voice and watching the face of the speaker, it would not be obvious that these statements were different at all.
Herein lies the challenge of communication in a digital age. We see text, a thought registers, and we never wonder if that thought was framed accurately. We hear what we hear, we understand it the way we understand it, and we move on. It simply doesn't occur to us that we should/could/might interpret it differently. Even without translation, much gets lost.
I know this has never happened to anyone else in the world, but I have tried to make a joke once or twice in an email or text, only to have my humor misunderstood, misconstrued, misinterpreted, and misapprehended. And they missed the joke, as well. Suddenly, we’re into a string of emails about how I was trying to be clever and every explanation makes it worse until I have to pick up the phone and actually speak with the person who is now furious with me.
Of course, that’s exactly what I should have done in the first place. If I had simply called, the other person would have understood my tone or inflection or that place our voices go when we transform a statement into a question. It turns out that you can tell a person, “I know this is really too difficult for you to understand,” in a way that makes it clear you don’t think they are stupid. But when you write it, it’s absolutely clear to them that, yes, you do think they’re stupid.
No matter how many emojis we add to an email—and I never understand any of them except the smiley face and the poop—the written word is incomplete. Face to face, we have tone, body language, pauses, volume, eye contact and other organically integrated cues for what we mean, how adamant we are, what we want, and whether we are finished with the conversation.
On the screen, all we have are letters and punctuation. And those inscrutable emojis.
It’s a safe bet that every one of us has offended somebody, possibly at some cost to ourselves or an important relationship, through a misinterpreted email or text. We might not be aware of who or when or how, but that’s really the point. We dash off 100 notes a day of one sort or another, almost invariably without re-reading them before we hit send…and voila. Strained and pained relationships ensue.
We see the damage from all of this when there’s some investigation or leak and we get to read someone else’s emails. “I will kill you,” or “I’ll do whatever it takes,” or “Of course, I’m guilty as charged,” shows up in text format and we know all we need to know about the writer.
By the time the author gets out the standard, “that-doesn’t-mean-what-it-looks-like-it-means,” disclaimer, pretty much everyone in the world has concluded that it absolutely means what it looks like and all that’s left is the sentencing.
Most of us can assume our emails won’t become social media fodder, either because we aren’t violating any rules or because we aren’t very important. You can never be sure, though, so it’s generally a good idea to adopt some protective rules for electronic communication.
First, never put anything negative, demeaning, incriminating or snarky into an email or text. This is impossible to guarantee in real life, but we can absolutely minimize the stuff that will be very embarrassing in hindsight. Even when discussing politics or a performance review or a disastrous date, the right wording can limit the need for future denials.
Second, if a conversation is going back and forth without a resolution, pick up the phone and call. Continuing an email string that isn’t coming to a conclusion reminds me of people who go to a foreign country and yell loudly and slowly in English to people who DON’T SPEAK ENGLISH. If no resolution is reached via email, the problem might be email itself.
I know this is an unexpected argument from a guy who earned his living putting words on paper, but facts are facts. The written word is a powerful tool, but it's not a complete workshop. As with any tool, it's important to know how it can be used and when it's a third-rate substitute for something else.
Remember that old saying that the medium IS the message? Finally, I think I am getting the idea.
Welcome, graduating class of 2018, including all seven of you who are with us in the stadium and the 22,000 who are streaming this ceremony in your parents’ basements.
It is an honor to share my thoughts with you on this historic day, and quite an unexpected honor, at that. After all the prominent speakers were disinvited due to protests, death threats, sex scandals and indictments, your university searched for a person with no meaningful opinions, no public engagement, and no gravitas whatsoever. I am proud to say I am that man. Or we are those human. I can never quite remember.
You are graduating into a fascinating and exciting world today. Unlike your parents’ generation, you are entering an economy with more jobs available than people to fill them. This is a powerful benefit for you, as you will need to hold down at least two jobs to make ends meet, or three jobs if your parents decide to charge rent.
Your choice of jobs, or “gigs,” is practically limitless. You can deliver groceries, deliver restaurant meals, deliver e-commerce packages, deliver passengers…just about anything or anyone you want. You can mix and match your gigs according to your interests and work whenever you choose, or whenever you decide it would be a good idea to eat.
The gig economy offers so much more than your parents could have dreamed possible. Your parents were forced to show up at work when the “Boss” wanted the office to open, and they were forced to wear shirts and shoes. Your parents were doomed to trade their lives away in exchange for status and financial security and health insurance and sick days and paid vacation. Today, you are free of those shackles.
No longer are you bound by the limitations of an office or a cubicle. No longer are you restricted by scheduled work hours or the constraints of employers who demand that you accept the health insurance THEY choose to subsidize for you or the 401(k) THEY think best to match. No longer are you required to let anyone know when you are taking a sick day, since you aren’t on anyone’s schedule and nobody is paying for your time.
At long last, you are free to pursue your own dreams, select your own health insurance, choose your own retirement plan, and pay for these benefits with your own money. You are free to choose: Lyft or Uber, Grub Hub or Door Dash, Instacart or Peapod…or all of the above. You are free like no generation before you to select your hours and your screen name and which decals you’ll be slapping on your windshield. Or your bicycle.
Of course, the greatest among you will make your marks by changing the world forever and for the better. You will achieve nothing less than a quantum leap in quality of life for billions of people. And by that, of course, I mean an app. I have no doubt that yours will be the greatest, most downloaded, most influential app in internet history, and your name will be synonymous with genius for generations to come.
A few of you will take a more traditional route by seeking out a “job” with assigned hours, along with benefits forced upon you by “The Man.” Friends might mock you for this retro path, but be strong, as going old school can be very smart.
Since you are a college graduate AND an internet native, you will have unique insights to bestow upon your colleagues. Your wisdom will be prized by everyone whose vision has been limited by actually working inside the company, or within the industry. Your fresh perspective will make it possible to understand the business fully and identify all its flaws within two weeks. After about three weeks, you’ll be ready to present the reorganization plan that will lead to an immediate promotion to CEO, or higher.
Because your talents are so important—and absolutely not the result of that class action suit about graduate job placement—we have added a job fair to today’s ceremony. Within minutes after you receive your diplomas, you can be pursuing your dreams and repaying your student loans, while the university complies with the terms of its consent decree.
The university’s attorneys want you to know this isn’t technically a “jobs” fair, since you will be signing up as “independent contractors” and not “employees.” However, you can sign up for as many “independent contractorships” as you want, with no restrictions on whose product you deliver or when you drive.
And so, graduating class of 2018, congratulations on your milestone achievement and on the contributions you will make to our world. We know you will succeed and that you will make a powerful impact on the lives of millions.
Just as soon as you can afford a car.