I love a good reset. Birthdays. School years. Fiscal years. Calendar years. New quarters, months, weeks, days. We get a lot of opportunities to pause, reflect, and press the reset button. For all of my post-college adult life, the Life Olympics has helped me take full advantage of these temporal markers, but the annual round-up is still my favorite.

2016 Awards Ceremony:

Career – Bronze

What a weird year for Allovue. We started 2016 fresh off of a Series A raise with big plans and big expectations for the year ahead. 2016 would mark the first full year that our product was in the market. Our team grew from 8 people in November 2015 to 24 by the end of 2016. We moved into a beautiful new office. We expanded to new states, with districts large and small, urban and rural. We hosted our first Future of Education Finance Summit. We launched our blog. We redesigned our product and built a new budget module.

Why the bronze, then? I wish I could tell you I was fully prepared for the nuanced challenges that come with 300% growth in a year, but there’s just no preparing for that. At several points throughout the year, I thought to myself, “So this is why investors don’t like first-time founders, huh?” I reflected a lot on the difference between bad decisions and wrong decisions: with bad decisions, you choose an option that flies in the face of data, advice, and general signs of trouble; with wrong decisions, you choose an option that made a lot of sense at the time, with the information at hand, and it later turned out to be wrong. Wrong decisions tend to be clear in hindsight, and I made a few of those this year. I’m ending the year a little more sobered on the myriad challenges of building something big and transformative, yet just as steadfast on mission and vision. My plan for 2017 is much more concrete and specific. In nearly 4 years of this work, 2016 may have led me up the steepest learning curve yet. In 2017, I’ll need to put those those lessons to good use.

Health – Silver

You know what? Not horrible. This was probably my most consistently healthy year, despite being on the road at least half the year and traveling about 150K miles. I even finally conquered the Whole 30 Challenge and got back down to my college weight before my 30th birthday. Silver because I still get into ruts with exercise and eating well (do you KNOW how hard it is to eat healthy in an airport?), and still prioritize work over health when push comes to shove. I aspire to be the kind person who maintains their diet and exercise regimen no matter what, but I’m not there yet. I’ve done a better job this year of saying, “Hey girl, you can take a 2 hour break for yoga. The spreadsheets will be here when you get back I PROMISE,” but I’m still not very good at keeping health practices sacred. Customer wants me somewhere? Investor calls? Employee has an issue? All those things take precedence. I’m not at all convinced that they shouldn’t. Maybe someday I’ll have a normal job and feel like work can wait, but right now I still prioritize all things Allovue over my personal needs, and I’m kind of ok with that.

Home – Gold

My little house is looking good. I finally fixed a leak that has been plaguing me for years, refinanced my mortgage, installed window treatments throughout the house, and got rid of some nasty overgrown tree branches. I finished redecorating a few rooms, and had a gangbusters year with AirBNB. This year, my AirBNB earnings fully covered the costs of my mortgage, taxes, and internet service. This has afforded me the financial freedom to save, invest, and travel. And ya’ll thought this was a terrible idea. I also hit all my personal finance goals this year by getting myself fully out of “I-floated-the-company-and-my-non-salaried-life-on-my-credit-card-for-a-little-while-debt” and finally prioritized savings.

In college, I made a deal with myself: I could make risk-it-all/you-only-live-once financial choices until I turned 30, and then I had to get serious about saving because I had officially made it out of my twenties alive. I took advantage of this by traveling all over the world with every spare cent, buying a house I couldn’t really afford, and quitting my job and cashing out my pension to chase a dream/vision. I have no regrets about any of this, but I turned 30 in November, so it’s time to hold up my other end of the bargain.

Spirit – Silver

A pretty good year for this old soul. I took trips to Paris, Cancun, Vegas, and back to the Dominican Republic for some good old-fashioned unplugging. I kept up with my singing. I hit my Goodreads goal of 35 books. I went to the symphony a lot. I saw Mike Birbiglia’s live stand-up. I’ve also just started calling bullshit more candidly when I see it, and that’s gotta be good for my soul.

I didn’t write as much as I would have liked to, so that’s a goal for 2017. I also didn’t see as much theatre as I would have liked to. And at this point, I’m really rusty on performing. I miss it, and need to find a way to incorporate it into my life that doesn’t involve 4 hours of rehearsal every night for 3 months.

Relationships – Gold fucking star 

The best thing I did this year on the relationships front was to reconnect with Ali, my best friend from college. She lives in California and we’d mostly fallen out of touch during the past few years. I learned from the Book of Face that she had landed the lead role in a Neil Labute play in Long Beach. I secretly booked a ticket and a flight and surprised her at the stage door. The look on her face (and subsequent mauling) when she realized it was me, is probably one of my top 5 memories. This was in July, and we’ve rendezvoused to Las Vegas, dined in LA, and spent my birthday weekend in Baltimore (her surprise to me) since then.

While I’ll probably never forgive the writers of How I Met Your Mother for their dream-crushing series finale, this Ted Mosby quote sticks with me:

“That’s how it goes kids. The friends, neighbors, drinking buddies, and partners in crime you love so much when you’re young, as the years go by, you just lose touch. You will be shocked, kids, when you discover how easy it is in life to part ways with people forever. That’s why, when you find someone you want to keep around, you do something about it.”

Truth be told, it hasn’t been that hard to meet up with her semi-regularly – it just requires some effort and planning. So, find the people in your life worth the effort, and just make the effort. It’s so worth it.

And my love life? My grandmother is banned from asking about it, and so are you.

In conclusion

So this is interesting: the categories in which I usually suck – not so bad this year! I think I’m doing a better job at being a whole person. I’d still rather be working than doing almost anything else all the time, but so what? My work gives my life meaning and purpose, so it makes sense that I would want to spend as much time as possible on it. I’ve come to accept this, rather than feel bad about it.

I often find myself driving alone across a stretch of America very late at night, on my way to some Residence Inn where I can heat up a frozen Amy’s lasagna from the lobby market before collapsing in a room that looks uncannily similar in every city in the country. I hum a little Taylor Swift, “Midniiiiight, long driiiiives,” headlights piercing the black night.

“There are students in those hills,” I think to myself; and this is my manifest destiny.

 

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…