Over lunch one day, a friend and I were discussing the challenges of leading people to the best decisions. He suggested that one way I am limited in that area is that I am too much a contrarian. In one group that we belong to, people anticipate that I will be the one to rain on their parades with challenging questions or comments. When I meet those expectations, my comments get discounted and my influence disappears.

He’s right about the impact of my actions, and I’ve seen this situation play out more often than I would like to admit. In fact, I know one guy who believes I am always wrong, because he believes I am always opposing the wisdom of the crowd. As a result, he becomes even more certain that he is correct if I say I disagree with his view. In his world, my accuracy is two steps lower than a stopped clock.

What if he’s wrong, though? What if the wisdom of the crowd isn’t always wise? What if the emperor is really a flasher?

Often, when people get together to make a decision, some ideas will gather momentum and others won’t. It’s not necessarily the value of the idea that drives that momentum, though. Sometimes, it’s espoused by a forceful individual, or it’s a view shared by two people in quick succession and the group dynamic flows from there. Once enough attaboys are issued, the idea becomes a truth destined to be chiseled in stone.

That’s where I join the conversation. I’m looking for the missing guest, the thing that should be considered and isn’t on the table. I’m trying to anticipate the unintended consequences of today’s big idea. I’m looking at how the ultimate audience is going to respond when the committee issues its report.
 
In fact, most of the time, I’m trying to figure out how to make the idea work in the real world.  And then, I open my big “contrarian” mouth.

How many customers do we have to acquire in order to make any money on this? What’s to stop Amazon from simply offering the same service and putting us out of business? What if Uncle Ernie decides to invest the money in a boys’ boarding school?

By the time I chime in, however, the train has left the station, that ship has sailed, and the chicken has crossed the road. My question becomes the final evidence that this is the best idea ever. “We all believed it was a great idea and then, even better, Rosenbaum didn’t like it. Pure gold!!!”

Time for some introspection. If I’m trying to help a person reach a better conclusion, but my approach often leads to a suboptimal decision, shouldn’t I change my tactics? Perhaps I should be more active in the chorus of attaboys when someone makes an inane comment like, “let’s break the mold,” or “we dare to be different.” Should I be more manipulative in the pursuit of a greater good, or is that one of those slippery slopes they talk about in law school?

​So, thanks to my friend for giving me something to consider in terms of the way I’m perceived. I’m working on it. Meanwhile, I keep thinking about the guy who has concluded that my disagreement is proof of his brilliance. There’s a great prank in here, somewhere.
 
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You can tell a question is very, very old when it’s based on the idea of mailing a letter. Bear with me, though, because this quiz from the Pleistocene Epoch has an important lesson that you don’t want to miss. (Okay, I don’t want you to miss it, but why quibble?)
 
As this quiz begins, you want to mail a letter. The closest post office is a mile away and you drive there at 30 miles per hour. How fast do you have to drive back in order to average 60 miles per hour?
 
Don’t bother grabbing your calculator, because I’ll give you the answer: You can’t do it. If you drove to the post office at 30 miles an hour, you used up two minutes. And if you wanted to average 60 miles an hour for the whole trip, you would need two minutes. By the time you get there, you’re already too late.
 
Life is like that. Whether we’re saving for retirement, planning a business strategy or leaving the house to meet friends, the clock is ticking. Too often, we start on a journey that we cannot finish, relying on hope or kismet or time travel for our ultimate success. That means we’re just wasting our time on a project that’s doomed to failure, when we could be investing our energies in a more promising direction.
 
Frequently, when I’m working with a start-up company, the management team will dismiss the limits of time, but that can be a fatal error. One company I advised had adopted a strategy that wouldn’t pay off until several quarters after they ran out of money, which meant it wouldn’t pay off at all. In another case, the business founder had started so many initiatives that she needed a 27-hour day to get the job done, but only if she didn’t eat, sleep or shower.
 
We make the same mistake in our personal lives. We don’t start saving for retirement until we need to save 120% of our income to make it work. We plan to travel the world someday, but wait until we lack the stamina to make the journey. We start a hundred hobbies, but we never block out enough time to master any of them.
 
And let’s not forget the little matter of relationships. So often, we are caught up in something that’s toxic, a situation that cannot be fixed without investing more time and energy than we will ever have…if it can be fixed at all. Still, somehow, we pursue a goal we will never achieve, draining our lives of more productive and enjoyable endeavors.
 
Nobody makes their final departure with a clean desk. In fact, nobody should make that kind of exit, because a healthy mess and a large to-do list can be indicators of a life well lived. Still, it’s much better to leave a long to-do list of items we enjoy, not a queue of boulders we’re damned to roll up the hill.
 
Time is the original scarce resource, but we treat it like a bottomless pool. The only way to make more of it, at least in practice, is to cut the non-starters and the never-wills from our to-do lists. Today might be a good day to start.

 
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​Over lunch the other day, a friend related the challenges of adjusting to changes within his own company. He is the boss, the owner, the big cheese, but his biggest job is that of a professional shape shifter, finding ways to adapt in order to remain relevant, and valuable, within the company he founded.

He was once the chief salesman, chief marketing officer, chief financial officer, and the chief everything else. Now, though, he needs to figure out new roles for himself at each step of the company’s development and with each new hire.

Over lunch the other day, a friend related the challenges of adjusting to changes within her own family. She is the mom, the aunt, the grandmother, but her biggest job is that of a shape shifter, finding ways to adapt in order to remain relevant, and valuable, within the family she founded.
 
She was once the mom of children, then college kids, then the mother-in-law and, now, a grandmother. And there’s no stability in sight, because she knows her relationships with her grandchildren will shift again as they grow.

Life, it turns out, is a continuous process of adaptation, a series of transformations into new roles, new responsibilities, new identities. We’re the...
...big-dog eighth grader
...lowly freshman
...big-dog senior
...lowly freshman
...new hire
...old hand
...new hire again
...old hand again
...the girlfriend
...the husband
...the dad
...the grandmother
...the caregiver
...the patient
...the survivor.

The crazy part is that we seem to be surprised when it happens. We change our roles and our positions in each organization continually, whether it’s our family, school, workplace or homestead. Each time, though, we wonder at the experience of needing, once again, to find our place, to make the adjustments, to fit into our new situation. Some people say they avoid change in their lives, but those people aren’t really paying attention, are they?

This could be a great life hack, a terrific lesson we can pass on to our children and grandchildren. Your life will be a continual process of adapting to new roles and new situations, with so many transformations that you probably won’t even notice when some of them are happening. Stay alert, though, because the lessons are largely the same and you’ll be applying them again and again and again.
 
Just as we share 99% of our DNA with chimpanzees, our transitions share 99% of the same factors, as well. New job, new school, new marriage, new friends…all bring the same mix of excitement and trepidation, insecurity and identity. The jargon changes, but the fundamentals are the same.

Unfortunately, our mistakes are often the same, as well. We all have a friend who keeps falling into mismatched relationships or jobs or investments. Sometimes that “friend” is the person who looks back at us in the bathroom mirror each morning. Once we learn to recognize the patterns, though, we can figure out what we’ve done well and poorly in the past, so we can ace the next test and the one after that.

​The specifics will change, but the process is eternal. New situation? No sweat. I’ve done this before.


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​The mysteries of business meetings, thriving on jargon, and the most thankless job in the world are all top of mind this week, among other cautionary tales…

1. If I've spent an hour coming to your meeting, don't burn up another hour on items that I could have read in advance. We don't need to be face to face if all we're doing is reading emails. 
2. And while we’re on the subject of meetings from hell, why is it that the most important person in any meeting is the one who arrives 20 minutes late? How else can we explain the organizer's choice to stop the meeting and review everything that was already covered by the people who showed up on time?
3. I’ve become quite expert at pushing the envelope and thinking outside the box and checking all the boxes and pursuing my passion and shifting my paradigms and giving it 110 percent. Can I take a nap now?
4. Most networking is a hundred people facing each other in a room and pushing cards at whoever is closest. It's a lot like the old commodity trading pits, except nobody makes any money.
5. Every so often, I’ll meet someone who calls himself a “serial entrepreneur,” which usually means he has started several companies, achieved some success with one of them, and is still trying to repeat his big win. In comparison, you have to be successful every time to be called a serial killer. Life is so unfair.
6. The most thankless job in the world is serving on a condo board.
7. Never show anyone how to do anything, ever. Once you demonstrate that you can do it, other people will decide they don’t need to learn it and they’ll want to rely on you the rest of your life.
8. I always envisioned myself as the quarterback of my team, but most days I was really the goalie.

 
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Six Tires, No Plan has a rating of 4.7 out of 5.0 on Amazon, so I shouldn’t be complaining about grade inflation…but it does seem that we’re all getting trophies for showing up these days.

I must admit that I am a true curmudgeon about praise. I don’t clap when some famous actor walks onto the stage, because he hasn’t done anything yet, and I seldom applaud when the fat lady sings, because that what she was paid to do in the first place. And, yes, I am the same guy who wrote that I want applause for finishing my dinner and tying my shoes, but that was about me, not other people. I am special and deserving, but the rest of the world? Not so much.

Like Yoda, I believe that there is no try and coffee is for closers. That doesn’t mean I don’t appreciate effort, but I don’t like participation trophies, either. Maybe it’s okay for toddlers, but we all need to be weaned by the time we’re seven. (This is the point at which readers will begin to feel bad for my daughters.)

I am clearly in the minority, though, because I cannot go to a play without enduring a standing ovation at the end. It doesn’t matter how good or bad it was> Everyone’s on their feet for the close, clapping like seals who just snagged a mackerel.

The same puzzle awaits me every time I take a Lyft ride. I always start with four stars and the driver can work up or down from there, but Lyft assumes that four stars is a mediocre rating and the only acceptable rating is five stars. Give the driver four stars and the caption comes up, “Okay, could be better,” and then they ask what was wrong. 
 
Nothing. Nothing was wrong. It’s a *&#@$% cab ride, not a private jet. I’ve had two or three rides good enough to bump my rating up to five, but really? Five stars for taking me to the dentist?
 
All this grade inflation has made the ubiquitous rating systems meaningless. A 4.5 rating on Yelp! could mean “very good” or “entrails with sriracha.” There’s no way to know. Ratings become meaningless when the top score becomes the starting point. 

Clearly, we need a six-star scale to restore meaning to this quagmire, and we should institute jumping-jack ovations for truly exceptional acting. Grade inflation will creep in, of course, and we’ll need seven or eight stars, and headstand ovations, in another year or two.

​In the meantime, I probably need to lower my standards for pretty much everything. And you need to rate this post 27 stars.

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​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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