2015 Life Olympics

December 31. Another year of the Life Olympics comes to a close. It’s been a yin-yang year: dark and light, grief and joy, exhaustion and renewal, despair and relief.

Let’s review:

Career – Gold Fucking Star.

Until July 18, I thought this was going to be a “Did Not Place” year for career (aka Allovue). The first half of 2015 was rather traumatic; fraught with doubt, fear, desperation, sleeplessness. Everything felt stalled: fundraising, product development, sales. Daily, I would turn the key in the company ignition and hear sputtering. Turn the key, turn the key, turn the key, with increasing desperation. Development wasn’t moving fast enough, sales weren’t closing fast enough, money was burning too fast. This is a recipe for founder madness.

Fundraise press releases are so glamorous: money! growth! progress! Fundraising is the farthest thing from glamorous, and I did a lot of it last year. I started raising a second seed round of a million dollars in September 2014. I closed the round in June 2015. 9 months. Friends of mine made entire humans in that time, and I? I kept my baby alive. Joy! Except. When it takes you 9 months to raise money, a good portion has already been spent by the time you are “done.” Despair.

The week we announced the raise, I went to a startup networking event and someone said, “You got your money, why aren’t you smiling?” I nearly screamed.

In February, I was fairly certain I was going to have to ask my executive team to go off salary to buy a few more months. In preparation, I sold my car to put some cash in my own bank account. To preserve cash, I charged every company expense possible to my personal credit cards (KIDS, DO NOT TRY THIS AT HOME). By March, I was personally carrying nearly $20K of company expenses. We would figure it out, we would figure it out.

In March, I took inventory of what other personal assets I could sell off. I had already cashed out my teaching pension. I had already sold my car. I was already pimping out my house on AirBNB. I looked inward. Literally. I started exploring options for selling my eggs. Hey, Ivy-League educated and blue-eyed genes can go for upwards of $50K. I submitted an application and informed my investors and advisors that I was ready to start auctioning off body parts. My inbox flooded with new introductions.

In April, an angel investor committed to $500K, keeping my company and progeny intact with a single check. I was standing alone in the ballroom of the Loews Hotel in DC when I got the call. I fell against the wall in a rush of vertigo. Relief.

I had lunch with my CTO a few weeks later and we made a pact to never again put ourselves in the position of being in such dire need for cash. On May the 4th, I wrote this:

I’ve somehow fallen into this trap of thinking that the goal is fundraising. That’s not who I am, that’s not the company I wanted to build, and that’s not the team I hired. I want to get back to where I started: the goal is to build a great company that serves districts, schools, and students. Fundraising is a means to an end, not an end goal in and of itself. I don’t know when I forgot that. I still want to build the biggest company we possibly can. I still want this to be the biggest opportunity in education. BUT I also don’t want to raise money because our bank account is running on empty. I want to raise when we’re really ready, on the best terms possible. That means we need to optimize for revenue right now and fight like hell to break even.

6 months later, almost to the day, we signed a term sheet for our Series A. We did not need the money.

I wish I could impart some grand lesson from this crazy rollercoaster of a year. I wouldn’t particularly recommend a lot of what I did this year. I only endured it because I knew in the depths of my being that, somehow, we would figure it out. But we survived – in fact, are thriving – and for that, I deserve a gold fucking star in the Career Life Olympics this year.

Health – Bronze Star

I think the very fact that I did not completely let myself go this year warrants a bronze star – especially considering all the traveling I did this year. I was on the road nearly 200 days this year, and somehow kept my yoga practice and weight fairly stable. ClassPass helped a lot – for a monthly fee, I can take fitness classes in nearly ever metropolitan area in the country. I’ve taken classes in dozens of studios across the country, and Bikram Yoga Baltimore is still my favorite.

There were weeks where I subsisted almost entirely on Chipotle, which is perhaps an area for improvement (is it, though??)

How do you measure – measure a year? In tacos, burritos, in salsa, in ques-a-dillas…

In one area that I definitely did let myself go was my self-image. Stress makes you feel old. And I was really fucking stressed out this year. I started to feel old. And then, because we are what we think, I started to act old. Recently, I realized that I hadn’t been to a bar on Saturday night since… I could not remember. And what the hell was I wearing? Flannel?? 19-year-old Jessica would have an aneurysm. I spent a lot of weekend nights in 2015 cuddled up with Darwin (my cat), a cup of tea, and my Kindle. And occasionally, that’s lovely. But not every night of every weekend. I’m in the Dominican Republic right now and I feel about 50 years younger than I have all year. And I should probably start acting my age.

Home – Silver Star

Even my poor house had a yin-yang year. In February, in the midst of that bitterly cold winter, my pipes burst. And since February is a big conference season, and I was already in a pit of despair, I really just did not have the time or energy to deal with it. So my house did not have water for a month. I was like a regular pioneer girl, flushing toilets with gallon jugs of bottled water. Thank goodness for my mother. She, like the rational person she is, believed this to be a serious problem and project-managed plumbers and contractors for a month.

Seven months later an AirBNB guest alerted me to the fact that my stove did not work. This reminded me that I had not attempted to use my stove since at least February.

In tacos, in sushi, in Thai food, in Indian takeout…

Then I needed I new roof. And my washing machine broke. And my bank account was very sad looking.

I realize this is sounding like a “Did Not Place” at this point, but I turned it around! For the past few months, I have put real effort into revitalizing my house and giving it some much needed TLC. I worked with a wonderful interior decorator at Su Casa to help me make better use of my living room space, which I had always felt was suboptimal. I sold my dark couches and replaced them with a light sectional that opened up the room. I added some color with upholstered chairs. I fell in love with a big painting by local artist Mateo Blu. I decorated in earnest for the holidays. I eeked out a silver star here at the very last minute.

Spirit – Silver Star

I did a better job acknowledging and prioritizing my emotional wellbeing this year, which is far more than I can say for the ghosts of Life Olympics past. I took vacations! Plural! I spent a lovely long spring weekend in Portugal, and I am spending the new year holiday sunning in the Caribbean. I also planned on spending a weekend in Paris in November, which very sadly coincided with the recent attacks, so I rescheduled my trip for the spring.

For the second year in a row, I met my Goodreads book challenge – and this time, several days ahead of schedule. I did not spend the week between Christmas and New Year’s frantically reading 7 books! I read a lot of fun books this year, finally freeing myself of the kaizen notion that every book I read must result in some improvement. Laughter and pleasure is plenty self-improvement.

I made some pretty major breakthroughs in my singing lessons this year. Here, too, I managed to let go a little. Perhaps I just reached my stress limit with work and couldn’t bother with stressing about my hobbies. It’s fine. It’s fun. Unclench.

Really and truly – I’m so grateful for yoga. It’s my church and my religion, and I got through some rough times in the cry corner this year. It keeps me focused and calm-ish. It’s almost entirely to credit for the fact that I didn’t have a stage 4 meltdown circa February. Nor March. Nor April. Breathe. Remember to breathe. It’s easy, and it’s fun.

My writing got the short shrift this year. Sorry. Something’s gotta give. I posted a lot on Facebook, and that will have to suffice for micro-blogging 2015. A respectable Silver.

Relationships – Did Not Place

I’ll be the first to admit that my so-called love life is rife with humorous anecdotes. But at some point this year, I started to think that perhaps the joke was on me. There is a barely perceptible difference between being able to laugh at yourself, and turning your (love) life into one running joke. As it turns out, there is some importance in being earnest.

The last two years, I have been a total Rose:


Sorry, boo, this is a life raft for one. Because love and lust and romance have a tendency to throw a girl off balance, and I am on a damned LIFE RAFT just trying to SURVIVE, here. So would-be boos were welcome to just chill in my icy waters. You can hold my hand… maybe… from a safe distance.

But now, I’m feeling a little more… buoyant. I have upgraded to a small dinghy that is suitable for recreation.

And there might be room for two.


2016 Life Olympics: On your mark, get set…

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