Tag: Emotions

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Startups

Day 155 and Momentum

Startups don’t really operate on logic, plans or “objectives and key results” to name and shame. Founders and executive teams get really good at planning and strategies only to have it all blow up in their faces. Generating momentum in spite of startups being incredibly resistant to planning is part of the trick.

I’ve been thinking a lot about the emotions that go into that “no plan survives contact with the enemy” reality of startup life. The past two days Alex and I have been enjoying a victory lap after the 1.8B acquisition of his former startup Stack Overflow. It’s a process of mixed emotions and shared experiences with other families that lived it with us.

But one central theme is that nothing changed in our skills, planning, insight or capabilities after we got the market validation. We didn’t suddenly get better and got rewarded overnight. Our plans got exploded like everyone else in startup land, over and over and over again. Till one day it was worth a bunch of money. Now everyone involved looks like a genius. But the reality is that the momentum of startups live a life and logic unto themselves. No one set an OKR for “billions” nor did they plan out a straight line from day 1 on acquiring customers consistently. No one planned out a ten year roadmap for creating enough value or revenue for a substantial exit. No one micromanaged shit for a decade. The momentum just worked itself out eventually.

And yes I’m using the Royal We here but mostly to make a point. Startups and their teams and the entire ecosystem around them are team efforts. Together we turn nebulously ideas into sketchy plans and eventually great things. Don’t get so wrapped up into the need to manage everything so closely.

A graph showing a bell curve distribution. The two outlier “make stuff”

The momentum of making stuff can and should eventually pull you into your goals. So don’t kid yourself all your numbers or plans do shit. Be the Jedi.

Categories
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.

Categories
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.

Categories
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.

Categories
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.

Categories
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.

Categories
Chronicle

Day 131 and Doing Less with More

I’m a lot busier recently. Maybe it’s a function of the ebullience that is gripping a vaccinated America but I’m finding more obligations in my calendar than I can recall in years. It’s still not quite to the place I was when I was a full time founder but I’m noticing fewer long blocks of time to myself.

I benefit from unstructured unencumbered time at rest. It’s not that I need it to be alone time or quiet time as much I need full on rest. I thrive when I have no reason to get out of bed. I do best reading and synthesizing when my mind is free to wander without any obligation to anything but that space.

Even otherwise pleasurable but not explicitly rest activities like going for a hike or painting my toenails doesn’t register as rest to me I’ll feel a kind of indignation when I’ve had an otherwise amazing day (filled with leisure activities) but didn’t get enough rest. I’ll think “sure it was fun” but also “now I’m tired and that wasn’t restful at all” goes through my head. For me the most restorative thing is not to do anything at all.

In fact the further away my activity is from boundaries like being constructive the more constructive I am afterwards. I try not to set myself up with the expectation that I am rewarded by productivity when I am at rest. That would set in motion the same circle of doing activities and not feeling rested because it wasn’t explicitly rest. That would become a kind of self limiting belief that leads to workaholism which I’ve pledged to avoid.

I hope that as the enthusiasm of exciting work and better help take more of my time I don’t feel tempted to indulge in activities that don’t feel restorative to me. None of this year would have been worth it if I went back to old unfulfilling ways of living.

Categories
Chronicle

Day 130 and Smiling When Sad

If you asked me my dominant emotion when I was younger I probably should have said anger. I was a fired up young woman. But as the years have gone by and the social benefits of seeming happy have piled up I’m finding it easier to spend more energy on smiling. This isn’t the same thing as being happy.

We like when people are friendly (even if we actually prefer they be kind) and I seem to have bought into it as a moral virtue over the years. I thought it was a gender thing but now I’m much more convinced it’s part of a family trauma cycle set in motion by my father who is exceptionally good at being liked. Cue Bojack Horseman joke.

You inherit your parents’ trauma but will ever fully understand it. Haha the cop is a cat.

Naturally I rebelled against perception of happiness and likability thing with a lot of anger as teenager. Cue lots of screaming stuff like “why do you care more if other people like you more than family” and you’ve got a pretty good idea of what I repeat to my therapist now as an adult.

And because intergenerational trauma and family systems work actually isn’t bullshit I’m starting to realize I stopped being angry and started smiling at some point not because I’m happy but because it’s a learned behavior from my childhood. And the smiling is papering over a lot.

What used to be passion, intensity and anger is fermenting into sadness over the years. Not because I’m actually sad inherently but because it makes me sad to lie about how I feel all the time. But I’m not entirely comfortable expressing any emotion. So now I smile when I’m sad. I’ve absolutely smiled when crying from sadness and grief.

Thankfully I hasn’t yet started laughing and smiling when I’m angry, but I fear if I don’t resolve this pattern and move on it might not be far off. I’ve still got significant work to actually feel my emotions in any given moment. Anger feels like it’s too reactive. Sadness like it’s a sublimation of something else. And if I actually am happy then I need to feel that. But I can’t force it with a smile.

Categories
Chronic Disease Chronicle

Day 129 and Worried About Wellness

Last week I felt like I was struggling to hold together level emotions and coherent thought. I had a lot of “feels” posts where I spent more time inspecting my interior world than I did analyzing exterior events.

When I feel energetic I can take in more information and engage in synthesis but when I’m feeling tired or otherwise am flaring from autoimmune condition I requires more mindfulness. This mindfulness lends itself to more of an inner focus. Often this brings me a sense of peace and emotional well being. Lately my case has been well controlled to the point of recovery, yet I haven’t felt as emotionally joyful about the development as I thought I would.

Then around Thursday or Friday of this week I found myself turning a bend. I was excited to think about very abstract ideas like the aesthetics of finance and how critical theory and how great works culture is colliding with Gen Z vibes.

I struggle with wanting to lean into enthusiasm though. Too many days in a row of exertion or excitement and I fear I’ll set myself back. That’s a kind of self limiting behavior that I hope I can let go. I want to feel confident in my energy but I do not want to turn myself back into workaholic habits either. This is a fear so persistent I’ve tagged eight posts in the last five months with the topic. So great is the fear that I felt some relief that I felt physically unwell today as I could blame my body instead of making the choice for myself if I wanted to be driven by energy and not recovery.

I can’t put off the mixed emotions on wellness and how I feel about working in the world. My capacity is nearly there. I’m taking on more and more. I have even plotted some of my next moves. But I’m feeling Augustine about the whole affair. Oh make well God but not quite yet!

Categories
Chronicle Internet Culture

Day 123 and Being Liked

I asked if folks cared if other people liked them today on Twitter. The results are surprisingly mixed on the issue.

A Twitter poll asking if folks care if others like them with 4 options: yes, no, yes but I like about it and no but I lie about it.

The four options were Yes, No, Yes But I Lie About It and No But I Lie About It. It is fascinating to see the breakdown in responses even a few hours into the poll. I don’t know what I thought the response would be but I don’t think it was an even split.

Now, of course, I didn’t ask if being likeable is good, or bad, or even helpful. I just asked if people cared. It’s likely people who do care don’t think it’s good that they care. And there are people who don’t care that maybe which wish did as caring about being liked may have benefits. I don’t actually believe that a third of folks don’t care as frankly society would look pretty different if 35% of us just didn’t care about perception. And sure you can argue that you don’t care but you hide the fact, but then your answer would have been the least popular option “no and I lie about it” which is lagging in the results. My guess is that a number of folks are aspirational “no” votes which I can respect. I’m confident I would have voted no in my twenties. I used to be an aspirational no vote

Currently my vote would be “Yes But I Lie About It” but I’m not sure if I’m lying to myself or others with that answer. I don’t generally care what people think of me but I think I lie to myself about needing to care. I think being liked is important and I want to act like I care more. I’ve got some hang ups about not having been a more palatable person when I was younger. Maybe if I had been nicer or better behaved or well…just more likable I’d be richer, more loved, have a better relationship with my family and other fantasies. I’m also not convinced that changing myself for others has the benefits I think. That’s just some 4 year old inner child trauma emotions. How others feel about me has little to do with me and a lot to do with them. That’s true for how I feel about others. My reaction to you says a lot about my emotions, trauma and hang ups than it does about if you are likable.