(written by lawrence krubner, however indented passages are often quotes). You can contact lawrence at: lawrence@krubner.com, or follow me on Twitter.

I’ll share this story. The year was 2006, when I lived in Charlottesville, Virginia. We needed to hire a Flash programmer. I put out a notice, got some responses, and then did some interviews. I eventually found a woman, who I will call Lisa, who was a little less experienced than some of the other candidates, but she seemed highly motivated. She was in her early 20s and just barely out of college. Her ambition was to become a great programmer and that came across in the projects she had done. So I decided I wanted to hire her.

Then I had to justify the hire to my business partner. He had veto power. I arranged a meeting so he could talk with Lisa. We met at the office, out in the forests of Nelson County, 45 minutes outside of Charlottesville.

When the three of us met, my business partner gave a bit of a speech about the difficulties we were facing, but also how ambitious we were to re-invent ecommerce, especially as it related to digital goods such as songs and videos. I thought his speech was a reasonable attempt to lay out the problems we’d expect Lisa to solve.

Lisa then replied: “Yeah, I know, I’m so scared. When Lawrence offered me this job, I was so worried about whether I could do it. I mean it’s all so complicated, and the connections to be made over the network are so uncertain, and then, everything, the timeouts, the servers, lost messages, everything I have to think about it, it’s just really overwhelming and I feel scared, you know?”

I was astounded by this, and not in a good way. I’d been assuming that she was smart enough to know that she should put her best foot forward. And I could see the doubt on the face of my business partner. I felt I had no option except to mimic her tone and make it sound natural.

I said, “Yes, exactly, I am so scared about all of the connections we need to make. The network can time out, the servers could jam up, the client might have a bad connection, their computer might have trouble running our front end code, I’m really scared about how many obstacles we face. Lisa and I talked about this in some detail. But I’m sure we will find a solution for each of these problems.”

And that seemed to get us through. I managed to switch the focus to the technology, which was scary, rather than allowing us to talk about the fact that Lisa was scared. Because that would have been a very bad way to start the relationship between Lisa and my business partner.

We worked with Lisa for 2 years and we produced our biggest successes with her. She gained a lot of skill. She eventually was worth more than we were paying her, but we had decided to move away from Flash, so we knew our relationship with her would come to an end. She got a good paying job with the University of Virginia. So the whole experience was good for us and good for her.

Why did she almost sabotage herself at the beginning?

Back in the 1990s, Deborah Tannen wrote “You Just Don’t Understand: Women and Men in Conversation“. One of the points she makes is that women tend to make themselves vulnerable so as to create closeness. Many female friendships start this way. And Tannen makes the point that men often misread this as a lack of confidence.

I was lucky that I’d read that book, because I was able to understand what Lisa was trying to do. She was trying to turn us into friends. She was doing that by admitting her fears. This probably seemed natural to her. She was young enough that her social skills were still focused on the kinds of friendships she had made in college, rather than the kinds of formal relationships she would eventually make in the world of work.

We were not her friends. We were her employers. I’m sure when she got older she came to understand the difference. But, at that moment, she didn’t understand the difference, and it almost cost her the job. Sometimes employers and employees become friends. But this should never be taken for granted.

I write this in response to Leah Fessler, a young woman who just wrote an article titled “I’m a millennial and I can’t get my older colleagues to be vulnerable. Help!” She has a lot of criticism for her older co-workers, such as this:

Oliver said that in his 20-year career, he’d been taught that any personal details you share could be used against you.

So why is it that the young person doesn’t take this as a lesson to be learned? Why is it that the young person assumes the older person is making some kind of mistake? Why is it simply assumed that the person with less experience has deeper insights than the person with more experience?

I’m writing this essay to offer a different perspective to Leah Fessler. She links to several articles which suggestion that openness and vulnerability can be good things in business. I’m sure that’s true, sometimes, but many times, it is not true, and in this essay I’m going to try to define the limits of openness as a strategy.

Now that Donald Trump is President, it is easy to think of some famous business people who are well known on social media. And there are some professions where it is important to be always in the public eye, especially the arts. If you are a performer, then your career is all about getting attention. And in any profession, a well written essay can enhance your reputation. A lawyer such as Orin Kerr can build their professional reputation via the quality of their writing. But I think we can agree, 99.9999% of what’s posted to social media is less impressive than the kind of essays that Kerr writes. What’s important is that Kerr writes about professional topics, rather than personal ones.

Looking at Donald Trump, some people might conclude that openness is a good strategy. Why not vent your feelings? Look where it got Trump. But this is a man who had a long career as an entertainer. To the extent that he’s been successful, it’s because he’s been strategic about what he reveals, and to the extent that he is heading for disaster, it is because he is often unstrategic about what he reveals.

If one is comfortable at a job where no one will ever care about your opinion then there is no risk in expressing yourself. But for the ambitious, it is worth remembering that for the most part, the old rules still apply. The best paying jobs are reserved for those who can keep their mouths shut.

If you want to be Vice President Of Sales at some company, you would be wise to be careful. One stupid tweet on Twitter might some day cost you your $250,000 salary.

If you are making $500,000 a year as a doctor, you should keep your mouth shut. The more you say in public, the more likely it is that you will slip up and say something that you were legally obligated to keep secret.

There are very few jobs in this world that pay you enough to put you in the top 1% of income and also allow you freedom of expression. Most of the time, high pay requires discretion.

I’m a millennial and I can’t get my older colleagues to be vulnerable makes this sound like a generational thing. Maybe it is, but I suspect this is more related to age and ambition.

Can anyone think of a believable scenario for the future where discretion is not rewarded for top level military officers, or world leaders, or corporate officers? While our manners and customs are forever in transition, I can not imagine a world where discretion loses its value for those at the top.

It is natural to express yourself when you are young, and people forgive you for it if you are young enough. No one expects discretion from a 16 year old, or even a 19 year old. If you commit an indiscretion when you are 23, it will eventually be forgotten. But at some point between the ages of 25 and 30, people begin to expect adult levels of discretion from you, especially if you are on a career track where people expect you to rise (doctor, lawyer, MBA, anyone touching large amounts of money).

Keeping secrets is important. Not just to the CEO of your company. Most of us have romantic relationships when we are young, of which we are willing to share the details rather openly. But at some point, things change. If you are 35 years old and married and have kids, then if you are lucky you will have 1 or 2 friends whom you trust enough to share the details of your experience. But if you broadcast the details of your marriage in public, you will put that relationship under strain. Obviously there are exceptions (especially for those in the entertainment or religious industries), but I’m describing the general rule.

At each age, we don’t know what we will only learn later. When I was young, I underestimated how much older people were acting. I did not understand the extent to which acting was important to economic success. Authenticity is rare, but people performing authenticity is common, and being good at that performance can build a fortune. Not just authenticity, of course. Being able to pretend that you are furious is a trick that all great sales people use. And being able to create the illusion of a sincere vulnerability can trick people into trusting you, which is invaluable. To be explicit about what I hope is obvious, a show like Housewives Of Beverly Hills does not show people being open and vulnerable to the public, it shows people who are performing openness and vulnerability, revealing enough of their lives to make the performance believable. (I am not advocating that you lie, only that you be aware how much other people lie. Don’t mistake a performance of authenticity for real authenticity.)

In How To Destroy A Tech Startup In Three Easy Steps I include a very long scene in which a once great salesperson uses a number of tricks in an attempt to out manuever me. At first he pretended to cry, to be vulnerable, to be sad, hoping I would feel intense guilt. When that didn’t work, he switched to rage, and attacked my masculinity, shouting “You’re just a frightened little boy!” His goal was to intimidate me. When that didn’t work, he suggested that I lacked talent, that all the problems at the company were my fault. I refer to him as a once great salesperson, because apparently he had a long and successful career, before I’d met him. However, when he dealt with me, I felt like he was over-acting. It was too obvious how he switched from one strategy to another. I didn’t get sucked into his act because at some point, as the years went by, he’d forgotten the importance of a believable performance. But he was probably believable when he was at the peak of his career, and you will interact with such people over the years.

My friends and I have sometimes discussed the right-wing television personality Glenn Beck and his tendency to cry on television. Is Beck truly overwhelmed with emotion as frequently as it seems, or is it all just an act? The best explanation I had ever heard, from a friend of mine who is a professional actress, was that a great actor fully experiences the emotions they’re portraying — so it’s possible that Beck is playing a character in one sense yet still genuinely feeling his emotional raptures in another.

To the extent that gender influenced the behavior of Lisa, or Leah Fessler, a possible title for my essay would be “How women sabotage themselves at work”. But that would be incorrect on two levels:

1. I could just as easily go with the title “How men sabotage the companies they work for by not hiring the best women”

2. either title would ignore the issue that workers have rights, and the demand for vulnerability can amount to an attack on those rights

“Break someone down and then rebuild them” is a brainwashing technique used by cults and government agencies that engage in aggressive interrogations of prisoners. Such a technique can demand total vulnerability so that the group can attack of the autonomy of the individual. You break someone down, then you can rebuild them to serve your needs. This is from Fessler:

Corinne Purtill, a Gen-Xer on the team, would later tell me that writing her user manual reduced her to tears. She thought the whole exercise seemed backward: “Insecurities and emotional needs… are not for sharing at work. Those you crush and throw away, like beer cans on the beach. Those you do not enumerate in list form for your supervisor or colleagues or anyone, ideally, if you can help it,” she wrote. I love Corinne—but what? Corinne admits that her philosophy causes problems in her personal life. But they’re “problems that­—and this is the beautiful symmetry of this system—I don’t talk about at work.”

Leah Fessler doesn’t seem to get that she is being forced to do this to serve the interests of capital. She is not doing this with a group of friends. A late night session in a dorm room rewards this kind of openness, but an exploitive economic system seeks this information to gain power over the workers. I agree with Fessler that this can be a powerful bonding experience, and I know sometimes the founders of companies deliberately put themselves through experiences such as this. That makes sense, the founders of a company should have strong bonds, maybe they should hike for a week in the wilderness and have long conversations around a campfire late at night. The leadership has quite a bit more control over their experience than the average employee, so the experience is much less exploitive for the leadership. But Fessler should not recommend this technique for her co-workers, until she has dealt with all the difficult issues of exploitation that come up around this technique.

Fessler thinks her co-workers are making a mistake. She sees them trying to protect themselves at work, and she describes this as “emotional numbing” which she feels is a bad thing. This is Fessler:

If that’s true, then I’m destined for great things at work. But whether we are in leadership roles or not, we all have issues—and hiding our baggage at work, in my eyes, is a massive waste of energy. As vulnerability expert Brené Brown explains in her infamous TED Talk, “you cannot selectively numb emotion. You can’t say, here’s the bad stuff. Here’s vulnerability, here’s grief, here’s shame, here’s fear, here’s disappointment. I don’t want to feel these. I’m going to have a couple of beers and a banana nut muffin.” I feel sad for those who believe emotional numbing is possible (and for those who’d choose banana nut muffins to numb their pain). On occasion, I cry in the office. Or rant to my work friends. Or sulk silently, do the bare minimum, then go home early. I don’t maintain a “work-self” and a “self-self,” and I don’t aspire to. It’s just too much effort (and yet also counterproductive, if you believe the experts). A few months ago, I changed roles at work, going from the youngest member of a millennial-dominated team to the youngest member of a team dominated by Generation X. Most of my new colleagues are at least 10 years my senior. Several of them have children, spouses, and mortgages. They are adults. Comparatively, I am a child. As a sharer, I don’t mind telling you, it was terrifying. It was also a little lonely. Gone was the office banter I was used to, about dating woes or roommates who don’t clean the dishes. The new group was cordial, but relatively formal. We’d ask about one another’s weekends without getting too many details in return. We’d brainstorm together on work ideas, but refrain from extrapolating them to our own lives. Then, at our third team meeting, our editor proposed a group exercise. We would each write the user manual to ourself, with specific guidance about our personalities, professional habits, and preferred communication styles, and we would share them with everyone on the team.

I totally understand feeling “a little lonely” at work. I prefer working with friends. I’ve been lucky enough to launch startups with friends of mine, and that can be a lot of fun. But it is also a very rare experience. What is common is working with strangers, some of whom don’t like us. And if I’m working with someone who doesn’t like me, I’ll want to protect myself. This isn’t “emotional numbing”, it’s just me keeping my guard up because someone really doesn’t like me.

So I would suggest three rules:

1. it’s often rational to be closed and guarded, because we often have co-workers who want to hurt us

2. it’s often rational to be secretly closed and guarded, while performing openness and vulnerability, so as to sell people on our vision, or our product, or our service

3. it’s often rational to be closed and guarded, because if you are ambitious, all of the top jobs are reserved for people who are closed and guarded

Discretion still matters. It always will.

Having said all that, I will add a significant qualifier, which I keep in the back of my mind whenever I discuss this issue. Our modern business culture was developed by men, at a time when it seemed natural that 100% of leadership roles should be held by men. We are slowly becoming a more equitable society, and we can hope that some day soon 50% of all leadership roles will be held by women. As women gain power, they will inevitably bring about changes in business culture. Parts of this essay may seem obsolete, on that day when women have had a chance to reshape business and politics. At that time, someone can write an essay about how all the rules have changed.

Till that day, I would suggest to all of you to remember that discretion still matters.

[ [ UPDATE ] ]

There is a good conversation about this essay happening over at Hacker News

I’ll add this: I am not suggesting that anyone lie to others. I encourage people to act with integrity at work. I think this pays off in the long-run. However, there is a difference between sharing every thought in your head and lying. Regarding Lisa, who I mention at the start, she could have said “I think this project is really ambitious” and we all would have agreed. We could have had an honest, in-depth conversation about the risks we were facing. I fault her for making the conversation about her personal fears and insecurities. She could have talked about her concerns in a less personal way.