Wednesday, December 31, 2014

2014 Life Olympics

The 2014 Life Olympics is my pursuit of stubborn gladness.

Career - Silver Star

The beginning of this year feels like 10 years ago. This time last year, I was still the sole full-time employee of Allovue, which seems totally impossible. I feel like I've been working with my team my whole life. I can't believe how much the company has grown and evolved during the past year. Hiring my team is the best thing I did this year, maybe in my life. They continue to delight and astound me. I can't wait to see what we do together in 2015.

So why silver star this year? I think I've let my work overrun my life too much. I can hardly hold a conversation that isn't about work, and if I do, it's half-assed, because I'm still thinking about work (sincere apologies to everyone with whom I've tried to hold a conversation this year). I've abruptly ended relationships and slowly abandoned almost all other personal interests in the name of work. Mark Suster claims that he seeks out this sort of founder obsession, but I'm not at all convinced that it's healthy. Intellectually, I know that I should not derive all of my joy, purpose, and energy from work, but it's easier said than done. In the coming year, I need to learn how to "turn it off" at times. I'll probably always be someone who is defined by her work, but I can't be totally consumed by it.

Home - Gold Star

I will just say this: I finally swallowed my pride and hired a cleaning service and it was one of the best decisions of my life. Even my mother remarked how clean my house looks.

Lesson Learned: achieving wellness in your life doesn't mean you have to do everything yourself. Ask for help. Pay for help. Don't add unnecessary stress to your life.

Relationships - No Star Awarded

I feel like I have developed a nice bond with my cat this year - does that count? No? Well, then.

I sucked at relationships all around this year - with friends, romantic partners, family. I have selfishly and ruthlessly prioritized work. I made a half-hearted attempt at dating for a few months, but after dismissing one nice guy after another, I asked myself, "What exactly are you looking for here, Jess? And what are you willing to give?" The answers were, "I have no idea" and "Nothing that requires any sort of emotional commitment or vulnerability because I don't have room for that right now." So. I decided that is not really a fair attitude to bring to the table, and maybe it was time for a little break from the dating world - or, as my grandmother calls it, "a sabbatical." And I have to say, I feel a lot better now that I have removed the (mostly) self-imposed stress of dating. I am clearly in no place to be in a serious relationship right now, and I have finally given myself permission to be single. Since I am a hopeless romantic at heart, I am sure that in time I will be ready to let the right person into my life in a real way. But for now, I'm on sabbatical.

Health - Bronze Star

I think I have been more consistently devoted to my Bikram practice this year than ever before. I feel stronger and more resilient as a result - physically and mentally. Bikram definitely overlaps with the spiritual wellness category for me, too. There is such a wonderful community of support at the BYB studio, and the solace I find in the hot room is unparalleled.

I have gotten off the bandwagon in terms of healthy eating. Again, here, I have prioritized work to taking the time to prepare and eat healthful meals. There were more than a few nights that I succumbed to the total cliche of just heating up some ramen. I have also had a few meals consisting solely of peppermint patties and wine. A sugar detox may be due in short order...

Wellness - Silver Star

This personal/spiritual wellness category is always my albatross. It seems a bit like cheating to count my Bikram practice in two categories, but it really does a lot for me beyond the physical effects. I have maintained my singing lesson every other week, which is a wonderful Monday evening delight. I've also rededicated myself to reading in a big way recently - especially works of fiction. Reading has been such an integral part of my life, and after months of feeling like a didn't have time to read, I just decided to make some time.  I started getting off the computer earlier at night and working in a good chunk of reading time before bed. My surge in reading coincided with my "dating sabbatical," so I guess you could say I traded men for books. Not mad at it.

Maybe some day, striving for personal wellness won't feel like such a burden. Maybe it will finally achieve its rightful place in the equilibrium of my life.

And 2015?
My friend Stephanie has a great philosophy about New Year's Resolutions that I'm adopting. Instead of making a specific resolution like quitting smoking or losing weight, she chooses a theme for the year to apply in all areas of life.

I want 2015 to be the antidote to my outrage fatigue of 2014. And how to combat fatigue?

Invigorate: give strength or energy to. 

Invigorate. It just sounds healthy. It's fresh and tangy and zesty and clean. Just the thing for 2015.

Sunday, November 30, 2014

If You Can't Do Anything Else

Every theatre kid has a moment (or many moments) when they consider pursuing a career in acting.

I had my moments. Every few months or so for the decade between middle school and college graduation (the heyday of my theatre career, as life would have it), I would threaten my parents with pursuing acting. I even declared a second major in Theatre second semester of freshman year (which I later demoted to a minor).

I remember the popular maxim that often accompanied these ambitions: "You should pursue a career in acting if you can't do anything else." It wasn't until several years post-college that I learned there were actually two interpretations of this adage.

I had always interpreted the phrase to mean that you should pursue acting if you couldn't breathe without it; if you felt as though you would truly perish from asphyxiation, choked by your own unfulfilled potential on the screens and stages of the world. (I was a little bit of a drama queen, and perhaps prone to hyperbole.)

Another friend interpreted it more literally: you should pursue your thespian ambitions if you simply have no other skills with which to barter in the game of Life. If that is your one talent, then you may as well play your hand. If you can do something - really, anything else - definitely do that instead.

I still like my version better. It has poetic conviction: give me the Backstage listings or give me death!

In any case, my theatrical ambitions didn't pass muster by either definition - I loved (and still love) theatre, but felt I could be happy leaving it as a hobby. In fact, I feared the opposite: that I would rely too heavily on the art as a meal ticket, take parts I didn't love in shows I didn't believe it, and slowly start to resent it altogether, the way people spoke of being sickened at the sight of ice cream after a summer scooping sticky globs of the stuff. And supposedly, after four years of a good college education, I had other marketable skills to lean on. (Time will tell, I guess.)

I spoke to a young(er) entrepreneur-in-waiting last week, and he told me he had a list of about a dozen business ideas he was thinking about pursuing. Without seeing the list, I told him none of them was the right one. He asked how I knew, and I said that when he found the right problem to solve, he would unquestionably know it to be the one to pursue. He wouldn't be able to do anything else.

Two years ago, that is how I felt about a problem that I later started Allovue to solve. I couldn't sleep. I couldn't stop thinking about it. I felt certain of my impending death, crushed by the weight of regret (there's that hyperbole again!) It's a feeling not so unlike lovesickness. I couldn't do anything else.

I think founding a business is a pursuit worthy of hyperbole. There's plenty of rejection, the odds are not ever in your favor - it's really not so different from a career in acting, when you think about it. For every break-out celebrity, there are thousands of people getting typed-out all day. For every Uber, there are thousands of wantrepreneurs honing their "Uber for X" pitches. Unless you're Richard Branson or Elon Musk, you probably can't just pick an idea off a list.

You should only pursue your business idea if you can't do anything else.

Saturday, August 2, 2014

The Last 5 Years in Baltimore

I never believed I was in Baltimore by accident. I woke up one morning in my senior year of college with the sort of impulsive conviction to move here that can only be attributed to fate. When I met a guy a matter of weeks after moving here, I was sure he was the reason I was here. When it fell apart the following year, I questioned all of my instincts and shook my fists at the fates and desperately wanted to run very far away and never look back.

And yet, here I am.

In the winter of 2011 I had been living here discontentedly for a year and a half and gave myself 6 months to find my people or pick up and go. Of all places, I started to find my people on Twitter in the technology community. I have to credit Kate Bladow for being a connector extraordinaire. It was on Twitter that I learned about Create Baltimore, and having declared to Crystal that I was going to Do Things and Go Places and Meet People, I went. Something clicked that day - I found a community of people that inspired me. I decided to stay. Relying on instinct again, I put an offer on a house the very next week.

I found myself in a dark place a year later, feeling completely at odds with my career, which was essentially my whole adult identity. We'll call this a quarter life crisis. I made a sharp turn into the world of venture capital, which didn't quite fit me, either. There were a lot of restless nights in the fall of 2012 as I wrestled with the spark of an idea that would not leave me alone. I saw it, but I didn't know how to build it. I didn't even know where to start. It was an utterly absurd, terrifying notion. I considered the worst case scenario and imagined abject failure, humiliation, bankruptcy. In this case, I supposed I would book a one way ticket someplace far away and open a waffle stand on the beach. That sounded pretty ok, actually. For a third time, I trusted my instincts.

And so, here I am.

Since I'm a big nerd, here's a little infographic of some Life Olympics highlights from my last 5 years in Baltimore.

Cheers, hon.

Thursday, April 10, 2014

Remembering Michael

In the pre-Facebook days, Penn had a separate online portal for newly admitted students to gossip about dorms and classes and clubs, and other pre-college chatter. Michael and I were both admitted early decision and we quickly progressed our friendship from Penn portal to AIM to the regular old telephone. We were 17 and it seemed impossible to wait 9 months to become in-real-life friends, so we decided to rendezvous at his house, just about 45 minutes north of mine. I met his lovely parents and then we made our way to the Wendy's drive-thru and took our cheeseburgers to a nearby park to listen to all our favorite music. Ok, Michael's favorite music, which became my favorite, too. It was the most ordinary thing for a bunch of high schoolers to do, but it was a memory made extraordinary by virtue of being with Michael.

Photo by Raymond Colon
I was shocked when Michael told me before winter break freshman year that he wouldn't be returning to Penn in the spring: he was joining the Navy. I balked at the idea. You? The Navy? The same guy who fiercely debates the merits of the Oxford comma at 4am? Michael made the case that he didn't really know what he wanted to do, and couldn't see the sense in spending all that tuition money figuring it out. Well. That may sound like a well-reasoned response, but Michael had gone to the same kind of parochial high school as I had, so we both knew he was supposed to graduate from an ivy league school with honors and settle into something suitably professional. He was deviating from The Plan. 8 years later, I found myself in the same situation, and I found myself channeling Michael's courage to carve out a different path. He was one of the first people besides my parents that I told about leaving my job to start the company, because Michael had a way of making you feel like you were destined to make all the big decisions you were making, and he'd just been patiently waiting for you to figure them out.

For the 7 years that Michael served in the Navy, he was mostly based in far-away places. Somehow, we knew our friendship was special, and diligently kept in touch with letters, emails, phone calls, Facebook, and a visit whenever he was on the east coast. He came to speak to my class during my first year teaching in Baltimore, which I think was an enlightening experience for all parties involved.

Getting older and moving around makes staying in touch with old friends harder. There's an illusion of intimacy since we're all constantly aware of each other on Facebook. It's easy enough to say, "We should totally get together the next time I'm in your city!" But Michael really meant it. If we were within 200 miles of each other, we would find a way to see each other.

We said we loved each other a lot. As a society, I think we're bashful about loving too much. We get wrapped up in the implications and insinuations and we treat each other so casually. Michael did nothing casually and we were unabashed in our mutual expressions of love and affection. Imagine if we were all so unapologetic about loving our friends? Just big, bold, audacious love. If anyone is afraid that too much love would make it any less special or intimate, trust me that Michael's whole existence was evidence to the contrary.

A strong theme has emerged in the dedications to Michael over the past few days: It didn't matter if he knew you for 10 minutes or 10 years, he made you feel special. Michael had some sort of super power in that he could immediately pinpoint all of your insecurities, gently make you face them, and just dissolve them, leaving only the beautiful parts. This gift for seeing the beauty in every person he met made him a remarkable photography, and a truly extraordinary human.

“You know when you've found it, that's something I've learned, cause you feel it when they take it away.”

Love you, Michael.

Monday, March 10, 2014

Don't Ban Bossy, Rebrand It

As someone who has been called aggressive, overbearing, loud, bitchy, smartypants, smart ass, intimidating, and, yes, bossy, since age 2, I do not approve the Ban Bossy campaign. I earned that title and I own it.

Being bossy is about as fundamental to my sense of self as being female, and I am not relinquishing the trait. I was on board with Lean In - that was a calling to step up, to take ownership, to stake claim. But banning bossy is about taking away - and that rarely ends well. Instead, let's reclaim it.

I have been bossy since the day I learned to talk. Being bossy has helped me to become captain, editor, president, teacher, director, CEO and founder of the various activities of my life. I was so bossy when I was a kid that my aunt wrote a book series called Smartypants that was loosely based on my antics. As recently as last year, I earned an award for my Bossiness (fittingly, the Tony Danza Who's the Boss and Tina Fey Bossypants award), courtesy of the Emerging Technology Center Accelerate Baltimore. I know bossy. I am bossy. And I own bossy.

I was bossy in the classroom, on the playground, on and off stage, at home, on the soccer field, on the pitching mound, and now, in my office. I suspect I will continue to be bossy until I take my last dying breath, with zero apologies.

Bossy is not the problem. Bossy has a branding problem.

Yes, women are called bossy more than men are. Men are also called assholes, jerks, and dicks more than women are. Yet, in the business world, being an asshole has a culture of idolatry around it, because that's how it's marketed these days. If you're a male CEO, being an asshole is a pretty high order compliment, because you know who else are framed as assholes? Steve Jobs and Jeff Bezos. I have great disdain for this particular reframing, because I don't think the world needs any more dickhead bosses running around with a god complex, but it's a great example of reclaiming a word.

So rather than banning bossy (which is bound to backfire, because nothing invites ridicule like prohibition), let's reframe it, reclaim it, rebrand it, and run with it.

Bossy steps up.
Bossy knocks it out of the park.
Bossy knows what she wants.
Bossy asks the right questions.
Bossy owns it.
Bossy runs the show.
Bossy gets shit done.
Bossy is efficient.
Bossy takes the lead.
Bossy doesn't whine.
Bossy makes no excuses.
Bossy takes risks.
Bossy doesn't take no for an answer.
Bossy finds a way.
Bossy wins the day.

Who's bossy, now?

Monday, December 30, 2013

The Year in Review

2013. I don't want to tempt (or limit) the fates by awarding this year any premature superlatives, but I have a suspicion that I will always look back on 2013 as a pivotal year in my life.

It's a little surreal to think that so much of what brings me daily joy and fulfillment didn't even exist a year ago.

For the past few years, I have come think of adulthood as the Life Olympics: the constant striving for balance between Career, Home, Relationships, Health, and Wellness.

The results are in for 2013:

Career - Gold Star
Founding and growing Allovue has been a thrilling and fulfilling journey, and I can't wait to see what next year brings. Despite the popular myths about startup founders failing to sleep, eat, or do anything unrelated to business orders, I think I succeeded in striking a pretty fair balance with the other 4 realms of my life, but there's still plenty of room for improvement.

I resigned from my job the first day back after the New Year holiday. I had come across this quote on Pinterest from We Bought a Zoo, and just kept repeating it to myself:

20 seconds of insane courage. Emphasis on insane. I had no plan, no funding, and no experience - just some gnawing intuition that I had to go bring this idea in my head to life, or feel the churning discontent of regret forever. So, into the abyss. 

I woke up on Monday February 4 - my first day as an untethered, fun-employed entrepreneur - feeling an odd mix of liberation and terror. For the first time in my adult life, (maybe my entire life?) I felt solely responsible for myself. There was no one to tell me what to do or how to do, but then, there was no one to tell me what to do or how to do it. I was a bit paralyzed by the weight of my newfound freedom at first, and then at 9:49am, I remembered: "To begin, begin," and so I began. I'm not sure what I did that first day, but I must have felt some vague sense of accomplishment, because I had this to say at the end of the day: 
I know it won't always be this fun...But isn't it ok to bask in the sheer exuberance of it - just for a little while? Just for today, I'll relish in the joy that accompanies the audacity to live the very life I imagined. Just for a moment, I'll play in that narrow intersection of pleasure and purpose, feeling infinite and electric.
Fortunately, that feeling lasted more than a day. The chaos of "startup life" feels oddly natural to me in a way that the routine of other jobs never had before. I think I worked on 8 different jobs this year to make it work, but I did it on my own terms, so I can finally read this speech without the nagging feeling of being slightly off center:
The only way to do great work is to love what you do. If you haven't found it yet, keep looking. Don't settle. As with all matters of the heart, you'll know when you find it. 
- Steve Jobs
Relationships - Gold Star
Speaking of matters of the heart, two weeks before I started Allovue, I decided I was tired of eating dinner alone and revamped my online dating profile for what I promised would be the last damn time. I agreed to exactly one date the day after I activated my profile. On the way there, I reminded myself (aloud) that I was officially done compromising on my non-negotiables in relationships. Maybe the universe just wanted to hear me say it out loud, because I went into Brewer's Art that night to meet the actual man of my dreams in real life. I don't know if there's ever a good time to start a new relationship, but I'm pretty sure it is not two weeks before you leave your job to start a company. I've heard it said that you find love when you find yourself - I just wasn't expecting it all to happen, like, immediately, all at once, very fast.

Home - Silver
In the Home category, I include basic home maintenance, cleaning, and keeping personal finances in order. My home was probably cleaner than usual this year, because I was constantly hosting new AirBNB guests. Talk about an incentive to keep the house in order when people are literally rating your house on its cleanliness! Of course, part of my strategy was to just relegate the mess to my room, but even that's had to change with the addition of our new kitty, Darwin, who likes to scratch, sniff, claw, and eat anything in reach. I'm running out of room to stash junk and mess, so it looks like I will finally have to be a grown-up and either purge excess or keep things tidy! #likeanadult

Health - Bronze
As it turned out, it was a good year to start dating a doctor/lawyer. At the end of January, I found myself engaged in a class-action lawsuit after it was discovered that my doctor had been allegedly secretly photographing patients with a camera pen and subsequently committed suicide. Feeling anxious about the care I had been receiving for the past 4 years, I quickly sought a new doctor and was diagnosed with endocervical adenocarcinoma in situ - stage 0 of a fairly rare form of glandular cervical cancer. My doctor said it was usually difficult to catch this type of cancer so early, but since we did, I was able to have a minor surgery to remove the cancerous cells. I just had my 6 month check-up, and my tests came back normal!

So this whole litigation/investigation process turned out to be a bizarre, potentially life-saving blessing. Unchecked, the cancer would have very likely progressed and I would have been facing far more invasive treatment options. This made me think about all of the men and women who put off visiting a doctor for routine check-ups because they lack basic insurance. If my father hadn't harangued me about securing private insurance before I left my job-with-benefits, a health crisis would have been a financial catastrophe, too. Even my small surgery would have cost over $10,000 without insurance. This whole ordeal gave me a deeply personal lens with which to view the Affordable Care Act debate this year. I'm thankful our country is finally making an attempt to fix what I can attest to be a very broken system.

Despite attending more Bikram yoga classes this year than either of the past 2 years I've been practicing, I still didn't get to as many as I had aimed for. This is an area of my life that I really to need to work on making it a permanent habit. It's (sadly) looking like the best way to do that is to just get up at 5:30am to make the 6am class. I've gotten better at it, but it's still going to take some practice to make it less of a struggle-fest in the morning.

Wellness - Honorable Mention
No surprises here. Personal wellness falls to the bottom of my priority list, year after year. I define personal wellness to include the things that feed my brain, creativity, and soul - probably not where I should be slacking off. This realm looks different for everyone, but for me it includes reading, writing, singing, cooking, taking pictures, and going to yoga. I fell woefully short of my book-a-week reading goal this year and abandoned my photo-a-week project in February. I did maintain my singing lessons every other week, which is a small victory, and I've started to carve out time for cooking delicious things on Sunday afternoons. This area definitely needs more work in 2014, and I think it needs to start with a shift in value judgment. In my gut, I know most of the inspiration for my "real" work comes from this personal creative time, but it's so indirect and quiet that it's easy to write-off these activities as less essential. No more! Wellness is essential.

You'll Figure It Out.
In 2012 I wrote a lot about gender politics in the tech world. One day, I stopped and took a hard look at my own life. Technology, specifically as it related to solutions for education, was clearly a big passion of mine. Why wasn't I doing work in that field? Why wasn't I taking a leadership role in the very area that I was lamenting a lack of female leadership? The answers were all rooted in blinding fear. I was afraid I wasn't appropriately "certified" to do what I wanted to do. I was afraid I didn't know how to do what I wanted to do. I was afraid of what people would think, or say. Then, I realized that none of these were particularly good reasons to not do a thing that I wanted to do. So, I decided to just muster up that 20 seconds of courage, and force myself to figure it out. I surrounded myself with smart, helpful people, and asked a LOT of questions along the way. "Leap and the net will appear," says an old Zen proverb. Sometimes, you just have to build your own net.

Monday, November 4, 2013

Scenes from an Indian Restaurant

SETTING: An Indian restaurant in California.

JESS sits down and scans the menu, which is unusually lengthy - a booklet of perhaps 15 pages.

MAN: You eat Indian food a lot? You know a lot about it?

JESS: I... eat it pretty frequently.

MAN: We don't really eat like that in India, you know. I mean, who could possibly eat like that every day? That would be ridiculous. It's much too rich. It's not real Indian food.

JESS: I think that's probably true of most ethnic food restaurants...

JESS, now self-conscious about what she is ordering, goes to the other side of the restaurant to submit her order. Upon return:

MAN: Do you work for Cisco?

JESS: No. My father and brother do, though.

MAN: What department?

JESS: My father works in the optics division and--

MAN: Oh, I don't know about that. Do you work in the software industry?

JESS: Yep. My company builds financial insight software for school districts. 

MAN: No... that's... public education is not very good. You should sell to private schools. There's no money in public education.

JESS: Well, about $600 billion is spent annually on K-12 public education - the private education market is only a small fraction of that.

MAN: Really? I guess you would know. So what do you do? Like marketing or something?

JESS: A little bit of everything, these days! I founded the company.

MAN: You can code?

JESS: I can, a bit. But I don't do development for the company. We have a great team of engineers, and I primarily drive the business development.

MAN: What made you do this? Just start a company?

JESS: Well, I used to be a teacher, and I thought there was a better way to think about resource allocation for public ed, so I started the company to build those solutions.

MAN: You just saw this problem... and started a company? You sound like a very aggressive woman.

JESS smiles politely.

MAN: Hm. Starting a company to solve a problem. Beat. You don't hear that very much. 

JESS nods.

MAN: A lot of people out here start companies. Beat. They have different motivations, though.

JESS: Like what?

MAN: Um... financial, mostly. 

Food arrives and JESS and MAN arise to leave.

MAN: Well, good luck. It sounds like it would be very difficult to do what you're doing. 

JESS: Thanks, enjoy your dinner.