DJ Scruggs

Destiny awaits us all

I’m not a fan of affirmations.

I tried them for a while several years ago. I would write down 5-7 affirmations every morning first thing, but I never really felt like I was getting anything out of the exercise. On the other hand, I have had a hit of financial success since then so maybe I’m wrong. Scott Addams, who I think is one of the most interesting thinkers alive today, is a believer and obviously has had truckloads of success.

Recently I’ve been reading The Antidote: Happiness for People Who Can’t Stand Positive Thinking by Oliver Burkeman (I found it via this excellent review from Ben Casnocha). It’s an easy read that nonetheless delves deeply into fundamental ideas about human nature. If I had to boil it down, I’d describe it as stoicism meets Buddhism. These two philosophies have always resonated with me. Buddhism I’ve been vaguely aware of since I was a child. I first became interested in stoicism  while reading Tom Wolf’s exquisite A Man in Full.

The Antidote has a chapter about the role of death in happiness. Counterintuitive, I know. Burkeman suggests that we should all contemplate death on a daily basis. By doing so, we are less likely to fall into the trap of not seeing the happiness that is right in front of us. Much of what he writes in this chapter is based onThe Denial of Death, which I also happen to be reading. (Six-word review: very good, but also very dense.)

This is not a new idea. “Live every day as if it is your last” is a common inspirational message. Steve Jobs’ famous commencement address is often cited. The speech is indeed inspirational, but I think it misdirects somewhat.

Why? Because the meta-message of Jobs’ speech, even if he didn’t intend it, is that you too can become one of the most successful businessmen in history if you adopt his philosophy. You can change the world!

But what if you don’t change the world? What if you are just another insignificant blip? Is that failure? Should your happiness dim?

No.

“Live every day as if it is your last” leaves out the most important word: death. You will die. Oblivion awaits. Someday in the not-distant future there will no longer be a “you” to experience reality.

The point of thinking about death, I believe, is not to think about  “success.” Rather, it’s to think about fear. Fear of losing your job. Fear of starting a company. Fear of introducing yourself to someone you’re attracted to. Fear of telling the truth in your relationships. Fear of ending a relationship that’s not working. Fear of failure. Fear of being alone.

In other words, fear of revealing your true self, your true desires. Fear of vulnerability.

The human mind is excellent at denial. We believe that we are immortal, and anything that challenges that belief is either avoided or transformed into a story of immortality (i.e. the afterlife). We use icons like Jobs, the Buddha and Jesus – who all appear quasi-immortal to us – to wish away reality. These people are all dead, and they will remain so for eternity.

(Apologies to any Christians who believe Jesus will return. My intention is not to start an argument. Suffice it to say that I personally believe he was just a very wise man who is now dead like all the others.)

It’s not just people. We use institutions, too. Monuments, culture, nationalism, patriotism, sacred books, the Constitution, presidential libraries: all of these reinforce the illusion of immortality.

Perhaps we could all learn from Woody Allen, who once said “I don’t want to achieve immortality through my work… I want to achieve it through not dying.”

So that’s all a prelude to my new daily affirmation, which I put as a recurring task on my calendar to pop up every day at 8:45 am:

via Altucher Confidential.

One time Barry Diller was visiting Sergey Brin and Larry Page. The topic of the meeting was to see how the greatest media mogul could work with the greatest Internet moguls.

It was like two galaxies colliding to create something beautiful when seen from light years away.

Larry Page was texting or doing something on his phone.

Barry Diller was disgusted: “Either choose me or the phone”.

Larry Page, without even lifting his head from his phone, said to the biggest media mogul in history, “I choose this”. Referring to his phone.

So Diller spent the rest of the meeting talking to Sergey Brin.

I love James Altucher, but I’m going to call bullshit on this story. This is just a little too just-so. If it happened at all, it was probably done in jest and they all got a laugh out of it.

This story sets up a myth: Great Man meets Great Man and Great Man wins.

The meta-story is: great men are not like you and me.

While that’s true on some level (I’m sure Sergey’s deep understanding of indexing lends an interesting perspective on the world), the reality is that most people, even very successful people, fail most of the time. Most of their ideas aren’t very good. But if you can execute well on one good idea, then it becomes an almost unstoppable train that overruns the bad ideas.

This is a very good thing: Powerful ideas can have powerful consequences, while most bad ideas have almost none.

This is a bad myth: It takes a Great Man to spawn great ideas.

We need less myth-making in the world.

I recently attended a workshop by David Deida, author of Way of the Superior Man. If you have not read this book, drop everything and read it now. I am not joking. The workshop was transformative to me and affects me every single moment of every day. I have made subtle changes in the way I move through the world, and the results are amazing to me.

Here is a very basic summary of what I think are some of the most important concepts.

Purpose

Purpose is what drives men to succeed, and it is what attracts women. Period. All the other PUA, dark triad bullshit is just an attempt to act like you have purpose. Once you have actual purpose, you don’t need tricks.

What is purpose? It’s not your job, it’s not money, it’s not something huge like “solve world hunger” — though all of these things can indicate that you have purpose. Purpose is simply the thing that you feel compelled to give yourself over too, and the denial of which will slowly and inevitably destroy your capacity for happiness.

For example, if your purpose is to create music, but instead you are a lawyer and just stare wistfully at the guitar every now and then, you do not have purpose. You have money but no passion. You become resentful and depressed, wondering why having the “right” job doesn’t make you happy. Nothing will make you happy until you fully commit to your purpose.

(As an aside, purpose does not have to be lifelong. You can fully commit to a purpose for a few years or less, then find a new purpose. So don’t feel like you have to find the One Great Thing that defines your legacy. Rather, you’re looking for the thing you can commit to fully right now. Also, if you don’t know your purpose, just make it the search for your purpose. Commit fully to finding your purpose and you will embody it.)

Presence

If purpose is attractive to women, what keeps them interested is presence. When a woman says she wants connection, she’s talking about presence. Presence merely means that, when a man interacts with a woman and his environment, he gives himself 100% to that interaction. That doesn’t me he supplicates or puts her on a pedestal. Merely that he says exactly what he’s thinking and is not ashamed of it or scared to tell the truth. He treats everyone he meets — be it a homeless man or powerful leader — as a distinct individual worthy of his complete attention.

Ego

Ego is very important. It’s what keeps us alive in the face of danger, and can provide emotional rewards when validated.

However, ego has a way of fucking up your presence. It can lead you to deny your emotions, or say hurtful things, or act in a passive-agressive manner. You must constantly monitor your ego. Forever. This never goes away. Ever. Get used to it.

How to monitor your ego? Here’s a good trick. When you say something to someone in a conversation, ask yourself “Did I say that because it’s true or because I’m trying to impress (or hurt) the person I’m speaking to?” If the latter, take the time to process the emotions that provoked that behavior.

This takes a lot of practice. Things like meditation, exercise and yoga (my personal choice) can help with it. Over time you will find that life becomes so much easier when you learn to recognize the ego. It’s like living in High Def after a lifetime of shitty TV.

A Winning Combination

When a man has purpose and presence, he is powerfully attractive. That doesn’t mean every woman he meets will sleep with him, but a whole lot of them will want to, and he will not have to use a single canned PUA routine. He will find himself in the position of being the chooser instead of the chosen.

Also, by bringing purpose and presence to everything he does, he naturally stops worrying about what other people think. This is a powerful, energizing feeling. The world becomes something you explore, not something to fear. Relationships become something you embody and witness, not something you cling to or hide from.

But How Do I Apply This?

Start saying and doing what you feel, not what you think you should do. If you like her scarf, say so. If he’s wearing cool shoes, say so. If she says something funny, laugh. If it’s not funny, don’t laugh.

If you think she’s beautiful and it makes you weak in the knees, say that too. I’m serious.

Your ego will tell you not to do these things, but by letting your ego “win,” you diminish the experience of life. You live in the world of “what if?” instead of right now.

This takes bravery. But guess what? Women want brave men. In fact, they crave a brave man who will protect them in the same way men crave sex. It’s fundamental to their experience. Pre-conscious, even.

A brave man is not without fear. In fact, some things may terrify him. But a brave man knows that fear does not define him. Only purpose can do that.

Quick sanity check.  A few of my friends have reacted to my last few posts with something like, “wow, I see your point of view, but I could never have the balls to post that.”

I get why people might think I’m a little nuts, but there is a method to my madness.

First, some background. In the last few years I’ve traveled a path that allows me to take a lot of social risks. Obviously as an entrepreneur, risk is part of my DNA. But as a single man with no family to embarrass and no employer to fire me, it’s not really much of a risk at all. Rest assured, if I were married with children I would not post these kinds of things.

More specifically, if I were in a committed relationship I obviously would not be asking bloggers out on dates. Ergo the experiences that inspired those posts would not even been occurring.

Second, last weekend’s date is a super-specific case. It was with a woman who trades on her fame. She’s not just a blogger, but a lifecaster. Her life experiences are “content,” and she emphasizes that she will not see someone unless she can also write about them. While she was here, I asked her if the reverse was true, and she said yes. So, there was no violation of trust.

To reiterate: normally there is no way in hell I would write about my intimate relationships. This is an extremely specific exception that proves the rule. A unicorn.

Third, I do believe we are entering an era of more authenticity, and I just happen to be ahead of the curve (especially for men). Think of it this this way:

• 30 years ago you couldn’t get on the Supreme Court if you smoked marijuana in college
• 20 years ago you had to pretend you didn’t inhale
• 10 years ago a guy who everyone knew was a recovering alcoholic who had used cocaine got elected President
• 4 years ago we elected a guy who casually admitted to snorting coke in his autobiography
• A few weeks ago marijuana was legalized in two states; many more are sure to follow that lead

So a pot-smoker in 1980 was a criminal. Soon she’ll just be a normal person. The person didn’t change, of course; the culture did.

Likewise, we have gone from a world where entrepreneurs, venture capitalists and celebrities were these mystical, magically successful people who we only read about in magazines; to a more authentic, warts-and-all view. Knowing that, for example, Ted Turner is manic depressive in my mind makes him more human, and reminds us that regardless of our achievements or lack thereof, the only thing that really matters is whether we can live with ourselves.

Or as Tyler Durden put it: You’re not your fucking khakis.

So I have a few more posts like this I want to get off my chest. Not because I’m especially insightful or an attention whore, but because they reflect who I am and what I think about.

Some people doubtless think I really am nuts. That’s fine, because I don’t need to be liked by everyone. If someone doesn’t like the real, authentic me, then I surely will not want to hang out with them either. Coming to that realization has been a turning point in my life.

Please read this disclaimer before reading this post.

Note: this post is I-swear-to-$DEITY the last post about the date I had with the batshit crazy girl known as Jen Friel. If you’re sick of hearing about her, just skip this post altogether. But if you’re game for one final round, here goes...

I once asked my therapist if I’m a narcissist. She laughed and said, “the proof you’re not a narcissist is that you’re self-aware enough to even ask the question.”

A few years ago I dated someone who I now know has borderline personality disorder (she cops to this diagnosis on her blog, but I won’t link to it out of respect for her privacy). She did not start getting therapy for it until long after we split up. Not because of anything I did, but because she’s finally mature enough realize that only she is the common denominator in all her problems.

And I now realize that Jen Friel is a narcissist.

What’s interesting to me is how much I’ve changed in the few years between those encounters.

First, a little background. Narcissists have a way of dragging others into their problems, then making them feel responsible. For a good example of this, read the biography of Steve Jobs. One of his early girlfriends talks about his unique ability to make her feel like his bad behavior was her fault.

So the first time I ran into this, I did what Jobs’ girlfriend did: I blamed myself. Why can’t I make this person happy? It was only through lots of therapy that I realized it was pointless even to try. Which is not to say I don’t have my own issues to deal with, but the path to longterm happiness is this: focus on what you control and ignore the rest. I’ve slowly adopted that attitude in all my decisions over the past few years and I feel at peace and empowered in a way that I once thought was impossible.

So when Jen wrote about my scary eye contact, and suggested that I flew her to Colorado to get business advice, my reaction was to just laugh.

And that’s probably where this post should end, but because I’m an INTJ, I did some more introspection. INTJ’s are good at pattern matching, so I looked back on the weekend, compared it to my previous experiences and tried to figure this out like an engineering problem.

Finally, it hit me: she really does think she’s the center of the universe!

She will even admit this, in a way. She refers to this trait as “confidence.” Which it is, though magnified well out of proportion, and perhaps explains why so many movie stars are narcissists. In a business full of rejection, it’s very helpful to have a personal reality distortion field. Numerous times Jen referred to the truckloads of confidence she’s had since childhood.

But the true sign of narcissism rather than confidence is the story she tells herself about what actually happened. It consists of three proposition:  1) that I am attracted to her, 2) that I want her advice and especially 3) that this is anything approaching a conventional date.

Let’s deal with the attraction part first. (I was advised by a friend to leave this out, but I’m a guy and looks matter to us, so here goes.)

Physically Jen did not do it for me. She’s reasonably cute, but no more so than anyone else I’ve dated, and definitely not the kind of person that makes me think “Wow!” when I look at her. That’s okay, though, because I look at the total package, not just whether she’s pretty. I only wanted to share this for all you guys for whom this unspoken question is top of mind. (That is, every single one of you. 😉

Intellectually, she’s reasonably intelligent but speaks in cliches. To give an example, she responds to a lot of comments with “Absolutely,” which I find grating. Not because I hate the word, but because people who use that are typically on autopilot mode. They aren’t listening and considering what you actually say. They’re just acting out rituals.

Now, regarding business advice.

I’ll start with the obvious: On what planet could she possibly think someone would fly her across the country for advice?!

She seems to think I was pitching a startup to her, which is emphatically not the case. I have my hands full with my current startup. I am pursuing a side project about the entertainment industry, and it may have career ramifications down the road, but at this point I’m just curious to learn more about the industry.

This is what is commonly known as an interest. I also have other interests: salsa dancing, entrepreneurship, fitness, politics, psychology (yes, including depression), economics, education reform and lately marijuana legalization.

We talked to some degree about all these interests because, you know, they are interesting to me. As with any date, I probed her interests as well and calibrated my conversation based on her verbal and nonverbal feedback. For her to zoom in just on the startup part and make it the centerpiece of our “date” suggests a highly inflated sense of her own importance. Sound familiar?

Bluntly, we did not have an actual conversation. Rather, she established an internal model of what the conversation should be about — her amazing business genius, natch — and processed the entire experience from that distorted viewpoint. It was confirmation bias to a shocking degree. Not just about a particular topic, but of the entire framework of our interactions. “I am a business genius. This guy is talking about business. Ergo, he’s a loser who desperately needs my brilliant insight.”

Finally, about the “date” part.

I suggested a date as a cute little framing device. A pretext for two adventurous people to take a risk. It worked out great for me in New York, which is why I linked to it in my original email to her.

An actual romantic connection, however, was extremely unlikely. Why? Well, let’s look at it logically by asking, “what is the most likely outcome of a first date from someone you’ve never met and who lives a thousand miles away?”

In the best-case, romantic comedy view of the world, we meet in person, are instantly smitten and next thing you know we’re making serious compromises in order to sustain a long distance relationship. While it can happen, I’ve been on enough dates and in enough relationships to know that this is a really stupid thing to even fantasize about. Odds of it happening: 0.000001 %

The most likely case: we get together, don’t really feel any attraction, but because of certain similarities (cultural tastes, career interests, we move in common circles) we develop a friendship. It could be shallow Facebook friends, or something more meaningful. I have a lot of friends in both categories. Odds of Facebook friends: 50%. Odds of something meaningful: 10%

Another case: we are both delighted to discover that there is mutual attraction, we have fun together, maybe there’s a romantic spark. But we are mature adults with our own lives that do not intersect very often, so we friend each other on Facebook, occasionally notice each other in our respective feeds and smile to ourselves. I have several friends who fit this definition. Odds: 5%

And the final case, the one I least expected, the worst case scenario: we repel each other. Not attraction, but loathing. I’m not the kind of person who has enemies, so this is really an edge case for me. Odds: 1%

Congratulations, Jen! You’re part of the 1%!

(Aside: It turns out Jen has compiled these statistics herself and they are about what I estimated.)

I’ve been on at least 150 dates over the last 3-4 years. Most of them didn’t get to a second date, some did, and a few blossomed into relationships. I got rejected quite a few times and did plenty of my own rejecting. Such is life in the dating market.

And we now know those dates included two narcissists.

The math: 2 narcissists/150 dates = 1.3%, roughly matching the incident rate of narcissism in the general population.

The first narcissist nearly drove me insane. The second one made me thankful for my own sanity.

Quick comment inspired by this post about StartupSchool.

Recently I’ve come to the conclusion that every single college student should be required to do internships as a condition of graduation.

I speak as someone who has hired recent graduates, mentored interns and perhaps most importantly flailed around for five years after college trying to figure out what the hell I was doing.

Most engineering schools already require this via a co-op program. But I think that every major — poli sci, gender studies, even fine arts — should offer a yearlong internship program that allows the student to spend time working in business, non-profit and government to figure out where they fit in. And they should come away from it with these measurable skills:

• How to run a meeting
• How to create and present a slide show
• How to persuade
• How to understand the incentives and economics that drive organizational decisions
• How to say “no”
• How to write a short, actionable email
• How to read a simple p&l statement and balance sheet
• How to have a difficult conversation with a co-worker or boss
• How to manage your to-do list (I’m partial to the Getting Things Done approach but there are other methods that may click better with different personality types)

These are all things I happen to be quite good at, but it took me years of floundering around to develop them. And I didn’t learn a single one of them during my crazily overpriced, elite-private-school education.

There may be other skills I haven’t thought of and perhaps even suck at. Please add your own in the comments.

(Now that I think about it, self awareness is a critical skill for every employee as well, but it’s hard to measure without going to therapy. Maybe in a mock interview where you ask people to describe their weaknesses?)

Please read this disclaimer before reading this post.

After the Jen Friel shit show, I asked a couple friends of mine to give me their honest feedback on that post. One of them, a close friend for over 25 years, is currently going back to school for a master’s in psychology. His overall opinion was that, when looking at my side of the story, I did nothing blatantly wrong.

Then we talked about my longtime attraction to writers (which I very clearly stated in that post). He said something very interesting:

My shrinky message to you would be, if you acknowledge that these female writers have seemed unstable and self-justifying in ways you probably don’t like or respect, maybe you should examine what is fueling your desire to pursue them.

I did some thinking about this and will continue to do so, but something bubbled up that makes me think this is definitely not a neurosis.

What is it?

The fact that I am attracted to male writers too!

Off the top of my head, here are some of the male writers I’ve enjoyed and corresponded with over the years:

• James Fallows – I’ve been a fan of his for almost 20 years, going back to this article about Japan. I’ve sent him numerous emails over the years (he usually responds) and met him in person a couple years ago at the Aspen Ideas Festival.
• Andrew Sullivan – I’ve followed him since — oh, 2001? — and also sent him many emails. He once ran a photo I submitted to his “View From Your Window” series.
• Christopher Hitchens – Never corresponded with him, but he was one those rare writers who can say things you vehemently disagree with but make you feel smarter for having read it.
• Mark Manson – Originally known as a PUA blogger, he’s evolved into something closer to Tim Ferriss (though I believe Mark is a better writer)
• Neil Strauss – Extremely talented writer who I first encountered in his autobiography of Jenna Jameson and later The Game (about which I have another post in the queue)
• David Brooks – I thought The Social Animal was brilliant, and I sent him a fan email saying exactly that
• James Altucher – his willingness to be vulnerable is a role model for my recent attempts.  Also, we are the same age and have had similar careers, so it’s very much a fellow-traveler kind of thing for me.
• Dave Eggers – also about the same age as me. Borderline too-hip in his style, but I can’t help but like it. I have a theory that people who like Eggers generally don’t like Tom Robbins, and vice versa. (I’m not a fan of Robbins.)
• Ben Casnocha – a very clear writer who thinks deeply about creating a life well-lived. I envy him having figured out so much at such a young age.
• Eric Ries – the guy has almost single-handedly changed the way we think about startups and has an extremely engaging writing style (he’s also an inspiration for my film production blog)
• Paul Graham – a legend in startup circles who exemplifies how writing == thinking
• Tyler Cowen –  he is first and foremost an economist (a field I love to read about), but he has an extremely dry wit that creeps up on you when you least expect it

Aside: the tagline for this blog is “Could you please be quiet?” This is an homage to Raymond Carver

I could go on and on, but you get the picture. Now compare this with the female writers I admire:

• Penelope Trunk – the poster child for vulnerability as a path to self-understanding
• Moxie – she’s super judgmental and we often butt heads — she thinks I’m a narcissist — but her views on dating have evolved over the years and that’s been interesting to watch
• Amy Alkon – she writes like a man. Super clever turns of phrase and a libertarian to boot.
• Dana Spiotta – Stone Arabia was brilliant and I sent her a fan email thanking her for writing it. The main character really struck a chord with me, reminding me of a close friend from high school
• Susanna Breslin – a recent discovery, though her blog is not her primary outlet

I belive the above demonstrates that I simply love great writing, regardless of gender, and it’s only natural that I would be attracted to women writers. But is that enough to say I’m not overly fixated on them?

Put another way, am I only attracted to writers?

No, and here’s the evidence.

• My ex-wife was neither a writer nor much of a reader. She has many other great qualities that I fell in love with.
• I also like dancers. I myself love both to dance and to watch dance performance. I even used to perform in a really cool dance group in Chicago. I frequently try styles outside my comfort zone. Just in the last few months I’ve taken lessons in capoeira, a yet-to-be-named style that combines dance and rock climbing, and salsa (at which I think I’m pretty damn good).
• I like musicians, though I don’t seem to meet them as often. I studied music in college and still noodle around on drums and guitar. A couple years ago I hosted a house performance by The Autumn Film. (They played on my back patio. It was like a miniature Red Rocks.) The downside of dating musicians is they tend to have a tough lifestyle. They usually work nights and frequently don’t come home until very late.
• And I’ve been attracted to people in other professions. In the past few years I’ve dated a chef, a Rolfer, a leadership consultant and a phsycial therapist skilled in the art of dry needling. Oh and an acupuncturist, too. (These disciplines are similar in appearance but very different in terms of the underlying theories – West vs. East)

I’m not crazy. QED.

Update: I’d be remiss not to plug my film production blog here. I have dated a screenwriter in the past, so obviously I’m attracted to people in that world too. So much so that I created a web site of interviews with them.

Please read this disclaimer before reading this post.

So… this just happened. The guy in Colorado she’s talking about is me. I’m not defensive about it, just reflective. But first the backstory.

I contacted lifecaster Jen Friel a few weeks ago and asked for a date. Go read that post. Correct me if I’m wrong, but I believe there are a couple of key data points you can glean from it:

• I have asked out two other bloggers in the past. One of them was right after my divorce and was my rebound relationship. (It’s not clear from the email, but I didn’t ask her out online. I met her at South by Southwest and we hit it off.)
• I have gotten rejected by those bloggers and am obviously okay with it. It’s even a comedic device.

What is not obvious from that post:

• I’ve asked lots and lots and lots of people out on dates in the last few years. Jen makes a big deal about going on 100+ dates in a year. Good for her. I’ve gone on at least 50 dates a year for the past three plus.
• Of that number, a grand total of three are bloggers. Scratch that. Just two. One initially said yes, then said no. That last one was totally a lark. She had written a post about how to ask a girl out, I thought it was funny and jokingly sent her an email asking her out. I was surprised when she replied back immediately saying yes. So I treated it like the potential adventure it was and bought tickets to New York. She ultimately backed out, but I still had a great time in NYC and don’t regret anything about that interaction.
• Most of my dates come from online. To me there’s not much difference between messaging a blogger and messaging someone whose profile I like.
• I am attracted to writers. I read shitloads and really appreciate good writing. So whether a women has a blog or not, if she has a well-written profile and looks reasonably attractive in her photos, I will ask her out. Double bonus points if she has good taste in literature.
• That said, I’m not a big fan of Jen’s writing. She’s real and vulnerable, and I like that in a person, but between all the “OMGs” and “totes mcgotes” I have a hard time getting through her posts. Which is not to say that she’s a bad writer, just that I’m not her demographic.
• On the other hand, I admire her and anyone else who manages to make a living online. So I was interested in learning more about what makes her tick. As I said in the initial email to her, “even at the end if nothing happens because we’re not feeling the chemistry, you’ll still feel like you had a great night.” No expectations.

Here’s what I thought happened

I met Jen at the airport late Sunday morning. My 30 second impression was, kind of cute, but not my ideal physically. Nonetheless I was inexplicably a bit nervous, which rarely happens to me on dates. However, I generally have a philosophy of saying what I feel instead of trying to hide it. So I told her I was nervous. She laughed a bit and said no worries.

From there I immediately got the vibe that she was not interested in me romantically. Which was fine because I wasn’t really feeling it with her either. However, I looked forward to giving her the full Front Range experience, and since she works in media I thought it appropos to mention that I’m thinking of making a career shift into film.

Here’s where I think I might have said the wrong thing: I introduced this topic as  “I do have an ulterior motive in case things don’t connect romantically, which is to learn more about the entertainment business.” She said sure thing, and for most of the ride back to my place we talked about it.

Note the words “ulterior motive.” This seems to be the words that set her off.  When I initially asked her out I wasn’t really thinking about the media stuff, but literally in the last couple weeks I’ve made a big shift in my thinking about it and gotten obsessed with learning more. Which is why I launched MakingFlix.com just two weeks ago.

So I guess from her perspective this was my angle all along. It wasn’t. I was just sharing my newly discovered passion.

In multiple places on her site, Jen makes a big deal about three things: authenticity, vulnerability and having no filter (i.e. she says what she thinks, hang the consequences). Though I probably have more of a filter than she purports to, I’m a also big, big, big believer in telling the truth. Further, I also am big about checking in with whomever I’m talking to to see whether we’re on the same wavelength. (I learned a lot about this in a sales training program I took years ago, probably about the time Jen was starting to dink around with MySpace.)

So I assumed that if there ever were some area of disagreement or phoniness between us, Jen would, you know, say something about it. Not having a filter and all that. She never did. Since I wasn’t feeling a connection with her, I figured it was mutual and that she wasn’t judging me (which is something she also claims about herself).

I love conversation. Not small talk, but deeper stuff that gets at our motivations. As I told Jen not longer after she arrived, I intentionally did not read much of her blog because I wanted to get her perspective and not create an image in my head of what she must be like. To that end, I asked her questions about her childhood, what motivates her, her personal and business goals, philosophies. We seemed to have a shared interest in learning how to be present and authentic. (Ironically, I believe I was the only one who committed to do this. She clearly held back and spent a lot of time on her phone.)

I did notice that she was quieter than I expected (she said “everyone always says that”) and that she did not ask me a lot of questions. I took this as a lack of interest. Fine, she’s not into me, I’m not into her, but let’s have fun. She says she’s all about adventure and so am I.

Here’s what we did

• Lunch at Dushanbe Tea House
• Walked the Pearl Street Mall, including an encounter with Zip Code Guy
• Dinner at The Kitchen Next Door (she loved the kale chips)
• Breakfast at Lucille’s
• A quick detour up Canyon Road to Boulder Falls, just to get a sense of being in the mountains
• Tour of Celestial Seasonings (I geeked out on the robots and thought she did too)
• Thai massage in Denver (about which she went on and on how relaxed it made her feel)
• I cooked a mighty fine dinner from scratch (at least, she said she liked it, but can I really believe her?)
• Breakfast at Snooze
• She mentioned that some of her fans in the area wanted to meet her. Numerous times I offered to take her to a coffee shop or wherever to facilitate that, but she waved it off.

 Here’s what I did not do

• Escalate physically – didn’t even try to hold hands
• Lie
• Judge her

Here’s what she didn’t do

• Give me any hint that she was having a bad time
• Tell me I in any way that I made her uncomfortable
• Say anything negative about anything at all. She gushed about how beautiful Colorado was. The only less-than-positive thing she said is that she doesn’t like cold weather and so would never live here.

Things that in retrospect I can only guess must have set her off

• I told her about a weird email exchange I had with that other blogger that left me feeling frustrated. I very pointedly did not let it devolve into trolling, ad hominem attacks, or judgement, and I listened to and validated Jen’s counter-viewpoint as someone who has been stalked and is thus cautious about dealing with “civilians.”
• On the way to the airport I told her I had made a list of people that I would email her about and would appreciate intros to them, but only if she felt it was relevant and she felt comfortable doing so. This list consisted of people in and around the film industry as well as an investor I’ve been wanting to connect with. For some reason she jumped to the conclusion that I wanted her to introduce me to other bloggers. What?! Where was that no-filter sensibility when it would’ve been useful? She should’ve just asked me! But instead she did what too many people do: made it all about them! She evidently believes that I have some kind of blogger fetish and woe is her for having to put up with crazy stalker fans like me.

How I feel about this

• Reflective. As soon as I dropped her at the airport, she posted on Twitter that she was glad to get away from my negative energy. This surprised me. I’ve been told I come across as (pick one) confident, intimidating and/or a bit intense, but negative?! Never. I asked a couple people to give me honest feedback about this and they expressed surprise. Of course, they could’ve been lying, too. I’ll just live with it.
• But not in any way “wrong.” There are a couple of things I might have said or done differently, but only if I could read her mind. I cannot do that and so I don’t regret anything I did. I believe that practically any other guest would have said I gave them a great introduction to the Front Range, and that was my #1 goal. Romance and/or career advancement were just gravy.

Final Thoughts

Jen slagged me on Facebook as a crazy person without hinting beforehand that she was in any way dissatisfied with me. I’m not really angry about that, just surprised. In the last few years I’ve become more adventurous and redefined my understanding of what “adventure” means. Fundamentally (as I told Jen, and she agreed), it’s about taking a risk. Sometimes risks backfire. If you’re scared of that happening, then you should not seek out adventure. (Note: she blocked me on Facebook after I made a not-nasty comment suggesting a countervailing viewpoint. So I have no idea what’s going on there. I assume she’ll have an epic post on her site shortly, which I’ll link to when it’s up.)

I took a risk and it blew up. But guess what? I’m still here. All that remains is for me to process the emotions, which is why I wrote this post. (Stoicism has a lot to say about this.)

Here’s me empathizing: it may be that she kept her mouth shut and felt trapped because, if I really were a crazy person (and she has met her share), she might have reason to fear for her life. So there’s an argument for keeping her real thoughts to herself. See? I just made it for her.

Now for the counter-argument: I am insanely Google-able and she saw exactly where I lived, has my phone number etc. We even have some mutual acquaintances. In the worst case scenario, she could very easily have contacted the many Colorado fans she has on Twitter and quietly asked one to come pick her up.

But given how much well-documented risk she’s taken in her personal life, it’s hard to believe she was truly fearful.

The biggest surprise to me is she seems to lacks even the most basic social toolset for tactfully seeking out proof of her nefarious hypothesis. On the “hidden agenda” thing, for example, she could have teasingly asked me “hey, I thought you said no agenda!” and smiled. Smiles and teasing are powerful social tools. She should know this because she helps teach social dynamics workshops. And yet it never occurred to her to try to validate her hypothesis? Nope, Derek is just Crazy Guy, end of story.

I do not believe in good and evil. I believe that binary formulations of just about any issue have the effect of lowering your IQ. Jen and I even talked about this. Jen claims to be a smart girl who sees shades of gray instead of black & white. But her habit of jumping to conclusions without seeking more evidence proves that, though she may have a decently high IQ, she still has a long way to go on the maturity. Perhaps some day she’ll change, but that’s not my concern.

I wish her well.

Next!

Epilogue

Last night a recruiter contacted me about a job in part because she loved my post about asking Jen out. I’m not looking for a position, but it’s nice to see that adventure can pay off in unexpected ways.

Risk, you are my friend. Is it yours?

Postscript

A friend commented on Facebook that this post made him worry about whether our conversations are confidential. Here’s my response:

That’s a fair question. I’m not in the habit of talking about other people on my blog except to quote things they’ve said publicly, but Jen is a public figure who trades on her fame. She also insists on the right to write about anyone she meets. I’m comfortable with my behavior and don’t feel the need to hide anything. I only wrote that post as a preemptive measure. (Normally I would not have written anything except perhaps a puff piece about the places we visited while here.) She had already slagged me on Facebook and I assume a similar blog post is coming.

And besides, as a public figure I’m sure Jen subscribes to the notion that there is no such thing as bad PR. She probably welcomes any and all commentary that doesn’t include the words “sex tape.” If not, she’s in the wrong business.

Please read this disclaimer before reading this post.

A few weeks ago I sent the note below to Jen Friel.

Subject: I know  how this turns out

Hi Jen,

I have a knack for getting rejected in really unique ways. Like, just a couple weeks ago I emailed and asked this hot mess of girl out on a date. She said “yes” within 10 minutes. So the next thing I know I’m buying non-refundable tix to New York. (Yes, I ended up being stuck there for the  hurricane.)

And then she backed out of it!

Why? Because of my Twitter feed. Something similar happened to me a few years ago. (I really oughta stop using Twitter. Definition of insanity and all that.)

But here I go again…

I want to take you on a date.

We’ll go to a nice restaurant, flirt a little, talk about cool stuff, take a walk afterward, stare into each other’s eyes and it will be so romantic and not-awkward. And you’ll think “wow, this guy is cool because he talks to me like a real person, not an idealized Internet fantasy.”

And even at the end if nothing happens because we’re not feeling the chemistry, you’ll still feel like you had a great night. Which is really all you can ask for most evenings, right?

We can do it in LA or Colorado, your choice.

Here’s what happens next. You’ll say “yes” because how can you say no to such a charming request? I mean, life is about experiences and I’m offering one. (To be fair, I know you’ve had a lot of them and don’t pretend be The One True Experience.)

Then you’ll, I dunno, Google me and wonder what kind of ulterior motive I must have, or assume my Twitter feed is an accurate representation of who I am.

So you’ll come up with some reason to be busy washing your hair that tonight. That’s okay, though, because I always have a plan B.

How about it?

And what do you know? She said yes!