2019 & 2020 post & pre mortems

For the past 6 years, I was scared to openly share my writing because I feared it might somehow “matter,” ie. negatively affect my company or be misconstrued. But in 2019, my company got acquired! Now, I’m a cat of leisure so I can post whatever, starting with these notes on my 2019 and 2020 goals.

I had 3 big goals in 2019: 

  1. exit Apptimize (done)
  2. finish writing my YA sci-fi novel (not done)
  3. go on a date with 1 person monthly with P score of 70%+ (done, although currently single)

Let’s drill in on each goal!

Apptimize learnings: 
I ran Apptimize for 6 years, constantly hero-ing before I became aware that there was another way to operate. After all, who else could possibly be held responsible for anything? Not only was I the founder and CEO, I’d always been the one responsible for everything I wanted my whole life, never viewing my teachers or parents as authority figures, always questioning directives. It wasn’t until the final version of my executive team that I was able to recognize I was working with people who were smarter than me about everything. Then I felt I could stop hero-ing and risk learning what happens when I stop (big thanks to my CEO group).

I wrote a post mortem of my experiences running Apptimize when we hired a new CEO in 2018. I was still technically at the company while he was selling it, but I was figureheading and not part of the acquisition. LMK if you want to see the post mortem bc publicly sharing my failures scares me. That was one of my learnings— I can talk myself into a lot of stuff that I don’t actually want for the sake of wanting to view myself as “successful,” but I don’t want to operate like that anymore. 

My new rule of thumb is to only do stuff that I’d do even if I knew it was likely to fail and if no one knew I was doing it. That eliminates me doing stuff out of ego/ fear/ status. This way I’m only doing stuff for the joy of doing it and not ascribing meaning to whether I achieve my preferred outcome. I’m always going to be an ambitious, driven person, so I don’t need to solve for that part of the equation as long as I’m focused on something I enjoy the process of doing, which brings me to my writing. 

Writing my book: 
Although my 2nd major at MIT was writing, I’ve never written a book and I almost gave up wondering, “Why am I doing this?” Writing a novel is easier than running a company (or possibly any job) in almost every way because it has no grounding in reality. Except writing’s harder in 1 way, which is staying motivated. I miss having a team I love. Writing is isolating and I’ve enjoyed partnering with Eva on our writing project and taking writing workshops at Stanford. After my 5 why’s on how I’ve missed my goal of finishing my book last year, I’m going to be at Stanford 3 or 4 days a week for the next 9 weeks because I have so many workshops. I feel like I’m back in school, except Stanford is so relaxing and resort-like compared to the Spartan halls of MIT. But to be clear, both schools are way easier than running a company.

I’ve learned life lessons from writing fiction. For example, you can increase drama in a story by amping up the subtext. The more desire, emotion, and expectation that’s unsaid, the more tension and conflict you can generate in a scene. There’s a gap between an external conflict and an internal conflict that drives all the action. Eg. the more the hero views climbing the mountain as somehow equivalent to gaining his dad’s approval, or the more the lovers are uncertain how they each feel while they’re competing against each other for the same trophy, the more emotionally turbulent the story. Drama entertains me in fiction, but is not fun for me in reality. Thus, even as I’m amplifying the subtext in my stories, I’m minimizing the subtext in real life. You know I’m already really direct, but now I’m even more direct about what I want. 

I realized that I had been in denial about some of my more “needy” needs, which was creating unnecessary drama in my life. My goal has been to delete the gap between my internal and external goals, between what I feel and what I communicate to myself and others. I’ve told people, “I’m afraid you’re going to think I’m weak if I admit to wanting to impress you.” Up until last year, I never would’ve admitted even to myself to caring what others thought of me except as a vague preference. I view myself as strong, independent, iconoclast who authentically does whatever she wants without considering outside approval, but I now recognize the part of myself that does very much care about being liked, being seen as successful, etc. Recognizing and embracing these internal drivers by bringing them out into the external realm has minimized the subtext in my relationships and drama in my life.

Other than drama, I’ve learned that the quality of my hero depends on the quality of my villain, and that this is analogous to real life. 2D villains are a missed opportunity for building a better hero, and that’s why my favorite villains (and corresponding heroes) are complex anti-heroes like the Joker and Batman, Magneto and the Professor. In life, whenever I’ve viewed a VC or competitor as an obstacle or antagonist, they’ve turned out to be my greatest ally in growth. It’s the challenge that defines the hero and gives you the opportunity to change and affect change. The villain in my book is my favorite character, and he’s taught me to appreciate the “villains” in my life too.

I’ve “dated” dated 4 people in the last 15 years. I started 2019 resenting dating. Dating was a waste of my time, not fun. I had a scarcity mindset about the candidate pool— the single guys my age were defective, hot guys tend to be idiots, etc, etc. I had a spreadsheet that estimated the probability with error bars that a particular candidate might be a match for me based on previous data points, eliminating candidates as soon as they became “known defective.” Although I’d update the weightings as new data came in, this scoring system proved faulty. Since I wasn’t running a company anymore, my executive coach refocused on my dating life. “How many dates do you need to go on this month to hit your goal? Your coaching worksheet says you went on a date with this high scoring guy but you’re not attracted. How will you adjust your process and scorecard as a result?”

Adjustments I made to my dating process: 

  • Asking for playful interactions. I don’t find judgment fun. I also find talking about the past boring— I don’t care to hear a rehearsed spiel about the dude’s past and he can google me if he wants to know my resume.
  • Guaranteeing 2 dates because I hate everyone on the first date.
  • No longer using dating apps because I’m shallow and random when on apps— I don’t find judging fun. Now I’m back to dating people in my network after we’re friends, which is how my best relationships have started.
  • Recognizing when I’m lonely so I can avoid dating in that state, because when lonely I throw the scorecard out the window and choose whoever’s most obsessed with me. Instead, when lonely, I should be snuggling cats, reading and writing, and hanging with friends.

I’ve also learned that my scarcity beliefs were false, which was a relief to discover. One of my board members caused me to realize one of my scarcity fears had to do with fearing being a single mom like my mom was after my parents divorced. I lived with my mom while she was dating and I was a teenager, and I had this narrative that it was tough for her because of me, and I was afraid of enduring something similar one day. I’m nowhere near being a single mom, so I wasn’t aware I had this fear, but it was great to identify it and realize it was irrational. This crazy unconscious fear had been making dating not fun for me, but now dating is fun. I also rediscovered this book while on the Southern Startup road trip and now aim to run all relationships with this type of integrity.

Going into 2020, this is the first time in maybe 7 years that I haven’t had a company or relationship goal. Company and dating goals were my top 2 goals in previous years, so this is a big change! I do get depressed when I’m not intensely working on something, and I miss working with a team I love, and I still want to build a fulfilling relationship with a man who inspires and loves me, but somehow I trust that those things will work themselves out without having a plan or goals. 
My goals for 2020 more have to do with all my writing projects, plus I want to make a short film (survey says the “dates with Nancy” short film sounds most fun. Sign up to see it when it comes out because whatever I make will have a limited, non-public release). At Apptimize we did pre-mortems in engineering. I like doing that for my goals: checking in on how shocked I’d feel if I didn’t accomplish a particular goal and then asking how I can make a plan and block out time to make myself more shocked to fail. If you want to share goals, let me know! I am a collaborative planning nerd. Happy 2020!