Category: Emotional Work

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Emotional Work Startups

Day 153 and Startup Families

I’ve worked my entire career in startups. I love it. But the work barely compares to being a member of a startup family. My entire life has been lived, literally from the day I was born, in the ecosystem of families that make startups come to life.

I was “in it” from conception and all my success and traumas are in some way tied back to that luck. And I became a startup founder and eventually a startup wife. This post is about what it’s like to live in perpetual uncertainty of creation with the occasional bout of life changing money.

For everyone that has a payday that changed their lives forever, chances are they have spent decades in the shadow of that system of building, scaling, and selling companies. The paydays are sporadic, completely dependent on luck and often extremely unfair. Most of the time the early team sees nothing. I’ve personally had an exit where I got nothing. I’ve had an exit where I couldn’t afford to exercise my options so when the company that bought mine exited I didn’t see a dime. So I know how fundamentally random startup life can be. How unfair it can feel. Because today it is our turn to be the beneficiary of the unwarranted success.

My husband Alex’s long time home Stack Overflow, sold for 1.8B dollars today. And yes we are one of the 61 families that will see more than a million dollars from it. But it’s not all joyful excitement in our house. Because it’s not about not just about money. It never has been. In my family it’s always been about belief. And it’s really hard to reconcile the many competing emotions that come with a liquidity event. It’s the culmination of much work and time from everyone.

My father proudly reminds me that when I was born, he didn’t have a job as he was pitching an education startup. What a blessing to have the energy of one’s life be aligned with risk from the start. And also what a curse. My family had incredible boom years where money wasn’t a concern coupled with devastating financial and emotional ruin as companies went to zero and markets crashed. My father sacrificed so much for his dreams. He saw the value of software and took his wife and children to the promised land of Silicon Valley. And oh it was glorious. And oh how it hurt.

I have fond memories of Comdex, elaborate company cruises and board meetings during “take your daughter to work day.” I also remember my father not being there for birthdays, for dinner, for milestones because he was busy building the future. I don’t remember my parents getting divorced, because I suppressed the memories. Family trauma can be like that. The good and the bad exist at the same time. When my father went bankrupt in the Web 1 crash, I was so angry at him for not being more careful, I didn’t speak to him for years. And then I made the choice to become a founder myself. Despite my fury and sadness and hurt I too decided to live my father’s path. And then I married a man who walks it too. I guess the Bojack Horseman joke got it right.

You inherit your parents’ trauma but will never fully understand it. Haha the cop is a cat.

The day you get news you made life changing money is bittersweet because all the trauma of being a startup family member catch’s you to you. You remember the sacrifice of your whole family going back years. The long nights and missed time together. The choices to prioritize the company over your family. In our case 10 years but of course for me it’s been my entire life.

The entirety of my marriage with Alex and my entire relationship with him before was spent at Stack Overflow. I’ve seen the hard work and the pride. I’ve also seen the exhaustion and the agony when something went badly wrong. The hurt when teammates left and the fear of leaving yourself eventually. People grow up together at startups. Other more practical logistics show that not everyone wins. The hard decisions you make when it’s time to leave and you cannot afford to exercise your options are a unique pain. We just three weeks ago sold something in secondaries to afford the taxes to exercise ours. That’s timing and dumb luck. Almost absurdly so. We could easily not be in the position we are. Exits are the end goal and yet not everyone gets to make it despite equal sacrifices. It’s all random and no one deserves any of it. But it changes your life if it does happen.

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Emotional Work

Day 148 and Ted Lasso

As I’ve written about before, I like shibboleths and secret codes. And Ted Lasso is my go to show for the language of emotional empathy.

It’s touched a nerve for a certain corner of the internet. The folks yearning for positivity. It shouldn’t have worked. And yet the show’s curiosity opens up your heart. It was a tonic for a tough year. So much of its magic is about learning to accept others as they are and love yourself for you.

Jamie Tartt: “Coach, I’m me. Why would I want to be anything else?”
Ted Lasso: “I’m not sure you realize how psychologically that is

I’ve written about the concept of psychological safety in building partnerships, most recently in venture capital. If you have a desire to improve your bonds with others try Ted Lasso. It will teach you much about feelings you never knew you had.

Whenever someone special is going through something in their life or if I just really love them I’ll rewatch Ted Lasso. I’m having an afternoon off and doing just that.

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Chronic Disease Emotional Work

Day 147 and Over My Skis

For a Colorado native (let’s ignore that I was born in Silicon Valley) a number of our most cherished pastimes are kinda “meh” for me. Skiing is a sport that I can take or leave. That apres ski life is much more appealing than cutting it up on the slopes. But one key metaphor from ski culture gets used lot. “I’m over my skis.”

To be over one’s skis is to risk crashing. Being over ones skis happens out of enthusiasm. An inexperienced or unfocused skier lets their center of gravity tilt forward over their knees. Best case scenario, you are simply going too fast and you better “pizza” your skis to slow down. It’s a endearing but slightly awkward experience which is what makes the metaphor so appealing. It’s never a bad faith metaphor merely a goofy oops.

I got over my skis this week. I’ve been so excited for my workload (new investments, new startups to advise) and some new structures forming in my life (chaotic.capital is coming into focus) that I’m leaning in and finding myself going too fast. A friend of mine, who is my favorite person to “over do it” with, was on the phone with me a lot. I was excited to talk to her. But all this added up.

I realized oh shit I need to slow down. I haven’t crashed yet but I’m french frying. There is still time for me to “pizza” or in the immortal words of South Park’s ski instructor Thumper

If you french fry when you should pizza, you’re gonna have a bad time

I love french frying, the food, the ski position and the metaphor for speed. I want get over my skis. But if I don’t pizza “I’m going to have a bad time.” So with true Colorado wisdom it is time to kick back, get some THC and pizza. May this edition of Rocky Mountain wisdom aid you in finding balance on the slopes and off.

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Emotional Work

Day 137 and Feeling Invaded

The line between feeling abandonment and invaded is thin for me. Being a child that often felt abandoned by my successful but distant father ingrained in me a fascinating pattern as an adult. I fear that I won’t be chosen, but when someone does choose me I easily tip right over into feeling invaded. I suspect this is a pattern many others will recognize.

There is a deep yearning to be the priority. My desire to be the one that gets picked is so strong. Such is the lingering fear of abandonment on the inner child. But because I have more comfort and recognition in the feeling of abandonment, when someone shows up for me it’s a swift inversion to the feeling of being invaded.

How dare this person who I so desperately wished would choose me then actually choose me! I will then become shy, distant, evasive and cold as the feeling that someone has overstepped their boundaries (which they haven’t) makes me retreat. For anyone who has ever been so sure that someone gave them all the signals of desire only to have it feel as if it was yanked away, this is the pattern your desired may be reenacting.

Because the consequence of being wanted is, well, being wanted. They desire something of me. I don’t even just mean this of friends or sexual partners. I can be thrilled that someone has chosen to work or collaborate with me and then when they approach me as if I have committed to them I will seize up with anxiety. The agony I feel at someone wanting something from me even when I gave them every indication that I want to give that thing to them is intense. My chronic fear of calendars is a deeply comical manifestation of this fear. I’ll spend an entire day agonizing over one short phone call in an otherwise empty day.

I doubt I’m special in this pattern of yearning and retreat. One of the most quoted lines from Star Trek is Spock noting “After a time, you may find that ‘having’ is not so pleasing a thing after all as ‘wanting. ‘ It is not logical, but it is often true.” For me it is often true and it is a pattern I wish to break. For when I reach out and offer my time and emotions to others I do mean it. The fear of invasion and patterns of retreat are simply a reactive pattern from my childhood. It is protective, and even in the mind of a child, logical. But children’s logic can only take you so far in life. As an adult I take responsibility for my emotions and through mindfulness can move beyond it.

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Aesthetics Emotional Work Internet Culture Politics

Day 134 and A Short Guide to Being An Edgelord

As my friend Seyi wisely said; sometimes your life gets chosen for you and sometimes you choose your own life. So try to chose your own life as often and as soon possible before someone else does. This challenge seems especially relevant as the culture wars rage on and regular peons like you and I can become collateral damage.

I’ve known for a while that I wasn’t going to be a fit for institutional settings like big tech corporations or civil service. I struggle to to be anything but myself. I mouth off too much. I’m not very good at kissing the ring. It’s not that I can’t engage in behaviors or manners you’d expect, I merely find it tiring. I’m also saddled with some physical limits. I’ve got the kind of medical conditions that gets a lot of virtue signaling from corporate communications types but isn’t really all that appealing except as a token. So unless I wanted to be miserable in middle management I knew I needed to opt out of the game. And that meant winning on my own terms.

Here is a harsh truth that the panic mongers in the cancel culture debate don’t want to say out loud. You cannot expect to survive a system and certainly not a culture war unless you take sides. Humans are riddled with bias and institutional self preservation is strong. The only side you should take is your own.

But you must accept that choosing your own life has consequences. Living out loud as the full uncensored you may cut off certain opportunities just as it opens new ones. Be aware of this reality and do not complain that you are a victim of circumstances when you have more choice than you realize. I’m not suggesting all areas are open to everyone nor that we shouldn’t fight for legal rights and protections. Merely that we are limited as individuals by the cultures and institutions of our time. Social mores move slowly even when pressed by revolutionaries.

My best advice? If want to be an edgelord. Be a real one. Go full crypto. Middle finger to the law. Fuck the police. Start a newsletter with monetization. Find your tribe. Learn some practical homestead skills.

You want to play corporate ladder? Play by those rules. There are dress codes and “ways things are done” and hierarchical structures you must obey. Get their credentials and be excellent at the values the organization wants.

You cannot straddle both worlds. This didn’t used to be a controversial statement. It wasn’t an affront that you had to put on a suit and say “yes sir” until pretty recently. Sometimes you just have to play the game. Go read the 48 laws of power and get back to me.

Trying to express who you are publicly if it’s not within bounds of the institutional norms might get you fired. Or maybe you take a stand that gets you promoted if you judge what norms can be pushed. Depends on the institution. So know that if you set onto the path of “choosing your own life” the consequences might be a lack of access and options. Or it might open you up to an entirely new world where you work and live with people who like you. But straddling the middle is recipe for emotional misery.

If I were you I’d begin to do the work to walk the path of the life you want now. Before someone else chooses for you.

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Emotional Work

Day 133 and Emotional Shibboleths

When I was a kid I was terrified of drinking. A family member went to daily Alcoholics Anonymous meetings and my reaction to it was “I hope I never become an addict because this seems like a huge time commitment.” Little did I know that it’s one of the best possible uses of one’s time! As a kid I had not yet been initiated into the secret code words of emotional work.

AA and Al-Anon are filled with shibboleths. So many phrases (don’t “should” on yourself) or or even a single word (triggered) that I heard in daily life turned out to be passwords for the initiates into emotional work.

It’s not just AA that uses a these types of passwords to show that you too have committed to to either program work or some other system of working on yourself. Inner child shows that you’ve done family systems or trauma work. Speaking of mindfulness generally means you have committed to a meditation practice.

Once you commit to therapy, performance coaching or program work (which isn’t just for alcoholics Al-Anon is for anyone) you will find yourself noticing the little hints that someone else is also on a path to working though their self limiting beliefs. Wait that was another shibboleth! Entire television shows like Bojack Horsemen and Ted Lasso light up the minds of folks on this path. My favorite quote from Ted Lasso is a classic framing of self love work

Coach, I’m me. Why would I want to be anything else?” Jaime

“I’m not sure you know how psychologically healthy that actually is”. Ted Lasso

If you ever find me using phrasing you don’t recognize it’s quite likely it’s because much to the chagrin of my teenage self I now know that this is the best possible use of an hour a day to work on oneself.