#Firstthirtyjobs

I have always been obsessed with working. My very first job was “Mother’s Helper” for my neighbor at age 9 and I just started collecting hustles from there. Unlike most young entrepreneurs, I wasn’t really in it for the money. I liked making money, but I viewed it as buying my independence to shop and travel where I pleased. I mostly liked collecting experiences, though, and I racked up quite a few:

  1. Mother’s helper/Babysitter (through most of middle school and high school)
  2. Face-painting/Nail painting at children’s birthday parties
  3. Cat-sitter
  4. Referee for Lincroft Soccer
  5. Umpire for Lincroft Little League
  6. Closet cleaner (for a hoarder – my job was literally never done)
  7. Secretary at a law office
  8. Marketing & box office sales for a local theatre
  9. Hype girl for a DJ – basically, got paid to do the electric slide at Bar Mitzvahs
  10. Salesgirl at Victoria’s Secret
  11. Bank Teller
  12. English teacher in Thailand
  13. Caterer (roommate and I catered campus events from our dorm room kitchen)
  14. Admin/coffee maker at Penn English Language Center
  15. Research assistant in South Africa
  16. Research subject in South Africa
  17. Kaplan SAT-prep teacher
  18. House cleaner/cook for a Penn professor
  19. Freedom School kindergarten teacher
  20. Netter Center assistant for Academically Based Community Service program
  21. Baltimore City middle school teacher
  22. Ann Taylor Loft salesgirl
  23. Adjunct professor at Towson
  24. ABS Capital Marketing coordinator
  25. Photographer
  26. AirBNB host
  27. Grant writer
  28. Director of education at Betamore
  29. Entrepreneurship bootcamp teacher at Towson
  30. CEO of Allovue

In support of the Maryland Angel Investor Tax Credit Program

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Last year, the Greater Baltimore Committee worked with Delegate Brooke Lierman and Senator Catherine Pugh on a bill that would have created an Angel Investor Tax Credit. The credit would function similarly to the very popular Biotechnology Investment Tax Credit but would be available to a much wider range of industries and companies. Despite two very good hearings, they did not get a vote on the bill last year.

Delegate Lierman has reintroduced the bill this year (Senator Pugh will be reintroducing, as well). Although I was unable to attend the hearing in person, I sent a written testimony in support of the bill, which is reproduced below.

TESTIMONY PRESENTED TO THE
HOUSE WAYS AND MEANS COMMITTEE
HOUSE BILL 471 –
Angel Investor Tax Credit Program
FEBRUARY 16, 2016

My name is Jessica Gartner and I am the CEO and Founder of Allovue, an education finance technology startup based in Baltimore City. I moved to Baltimore in the summer of 2009 as a Teach for America Corps Member. I taught middle school humanities in Baltimore City and completed my Master’s degree at the Johns Hopkins School of Education. In 2011, inspired by the energy and potential of Baltimore, I bought a house in the Hollins Market neighborhood, thanks to homebuyer grants from the Live Baltimore program.

In February of 2013, I quit my job to start Allovue. I was haunted by the inefficiencies of school financial management, as I had observed first-hand the direct impact that resource allocation has on teaching and learning. I believed that innovation in education finance technology could drastically improve access to timely financial data and help education leaders make better resource allocation decisions by connecting spending to student achievement data.

By all accounts, this was a completely insane idea. I had no previous experience in business, technology, or finance, but I was intensely driven by a vision for an education system that allocated dollars effectively to meet the needs of our students. I believed that I could rally a team of brilliant software engineers, data scientists, education finance experts, and designers to build a product that met the uniquely complex needs of education leaders everywhere.

Three years ago, I was a 26-year-old girl with a bold idea, a few PowerPoint slides, and an incredible passion for improving educational outcomes. The Emerging Technology Center in Baltimore took a big bet on me. I was accepted to the Accelerate Baltimore cohort in 2013, which provided our first investment of $25,000 from the Abell Foundation.

During the next two years, I raised two rounds of seed capital for a total of $1.8 million. 42 percent of that seed capital came from Baltimore angel investors. I used this capital to hire our founding team and build a product that was ready to go to market in school districts across the country. In December [2015], we raised an additional $5.1 million in Series A funding, led by Rethink Education, which will catapult our growth to a new level in 2016.

Today, I hired our 22nd employee, representing nearly 300% team growth over the past 90 days. Of those 22 people, we are in the process of relocating 7 of them to new homes in Baltimore City. We have just begun offering Live Baltimore matching grants up to $5000 to all employees who choose to buy homes in Baltimore. I sincerely hope they all take advantage of this.

Our sales are up 1000% since this time last year. In 2016, we are projecting 4000% growth over 2015 revenues. We are now working with school districts and state departments in 10 states across the country, helping education leaders manage and analyze over $3 billion in funding. And we’re just getting started.

None of this would have been possible without the early capital from angel investors. Angels make the riskiest investments in innovation – they bet on crazy, unproven ideas from inexperienced and unlikely founders, yet this is origin story of nearly every major technological breakthrough in America. Let’s make sure that more of them come from Maryland.

We should offer every incentive for betting on innovation and economic growth that starts and stays in Maryland. I hope you will vote to support the Angel Tax Credit, ensuring that all Maryland entrepreneurs with crazy ideas will have the best opportunities to access the capital necessary to build the next big thing.

For these reasons, I urge you to support House Bill 471.

Screenshot 2016-01-01 09.50.16

2014-2015 Goodreads Challenge

Towards the end of 2013, I rededicated myself to reading for fun. As a kid, I devoured books. We would go to the library bi-weekly and check-out stacks of books. I killed those Book-It Challenges (even though my mother rarely let us actually redeem those personal pizzas) In one summer alone, I read over 10,000 pages.

In high school, I had a lot more reading to do for school and stopped reading as much for fun. Same for college – especially as a liberal arts student. Each year, I read fewer books just for fun. After college, I wasn’t exactly swimming in free time as a full-time teacher and Master’s student. I read between 5-15 books per year – a far cry from my childhood records. I missed it, wistfully roaming the aisles of bookstores.

I’m not sure what course of events reignited my passion for reading, but I recommitted to it, and my reading has happily and steadily increased over the past few years:

Screenshot 2016-01-01 09.50.16

Since the past two years were great reading years for me, I thought I’d summarize my reading lists and highlight my favorites. For my full list, check out my bookshelf or follow me on Goodreads.

Top 5 books of 2015 (out of 31):

  • All the Light We Cannot See by Anthony DoerrScreenshot 2016-01-01 09.58.52
  • The Goldfinch by Donna Tartt
  • Between the World and Me by Ta-Nehisi Coates
  • Modern Romance by Aziz Ansari
  • The Empathy Exams by Leslie Jamison

Top 5 books of 2014 (out of 25):

  • Americanah by Chimamanda Ngozi AdichieScreenshot 2016-01-01 09.58.32
  • Zero to One by Peter Thiel
  • Dataclysm by Christian Rudder
  • The Hard Thing About Hard Things by Ben Horowitz
  • The Signature of All Things by Elizabeth Gilbert

 

 

 

rose

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:

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…

Challenge: A Month of Gratitude

Last month, I was stumped on Spirit goals for June, so I crowdsourced some ideas. Justin Kownacki suggested the exercise of writing down three things I felt grateful for at the end of every day. This fit nicely with my goal to journal daily in DayOne, so I accepted the challenge.

gratitude

I had low expectations. I had heard that this type of ritual can help increase your general happiness and blah blah blah. I was mostly looking for a way to document small memories of this important time in my life… to remember “how it felt to me,” as Joan Didion perfectly describes the benefit of writing things down in one of my all time favorite essays, On Keeping a Notebook (emphasis mine):

So the point of my keeping a notebook has never been, nor is it now, to have an accurate factual record of what I have been doing or thinking. That would be a different impulse entirely, an instinct for reality which I sometimes envy but do not possess. At no point have I ever been able successfully to keep a diary; my approach to daily life ranges from the grossly negligent to the merely absent, and on those few occasions when I have tried dutifully to record a day’s events, boredom has so overcome me that the results are mysterious at best.

I accepted Justin’s challenge, and I must say, I am rather shocked by the results. As the month went on, I found that my habits of mind noticeably shifted: I became aware of my gratitude in the moment. I started thinking, “I’m feeling so grateful to have this right now – this will be one of my three things today!” This was a revelation. I am not a live-in-the-moment kind of person. I am a futurist to the core, and usually thinking, mulling, planning for the hours, days, months, years to come. Feeling grateful in the moment was new to me, and at the risk of being redundant, I’m grateful for it.

I also noticed that most of the things that immediately came to mind at the end of each day were rather, well, small: a bite of fresh food, a chat with a friend, a good laugh – hardly none of the seemingly epic milestones that constantly stress me out made the list. Another seismic mental shift: The small things are the big things. 

I’m so pleased with this challenge that I’ve decided to continue it, logging at least one moment of gratitude each day. And, I had so much fun with it, that I welcome NEW Life Olympics challenges for July!

My 90 moments of gratitude from June:

I’m grateful for…

  1. Lunch with Ted
  2. My new standing desk
  3. My new bag
  4. Small problems
  5. The Sangria Series
  6. Nerd lunch with Robbie
  7. Jen
  8. Knowing so many insanely talented and creative people
  9. Under-promising and over-delivering
  10. Girlfriends
  11. Cream puffs
  12. My health
  13. Friends who take me to the theatre
  14. Aguachile
  15. Celia
  16. New office chairs
  17. Summer naps
  18. Having Mom back home
  19. The farmers market
  20. Ripe blackberries
  21. A new lamp
  22. My grill
  23. My amazing team
  24. Form D filing done!
  25. People who get it
  26. Katie
  27. Paige
  28. Great press headlines
  29. Investors who believe in me
  30. Privacy options on Facebook
  31. Bossy ladies
  32. New friends who skip the small talk
  33. Ignite talks
  34. Strategic partners
  35. Inbound sales
  36. Custom Slack icons
  37. Being able to afford a new roof
  38. Friends who inspire me to get in better shape
  39. Bikram Yoga Baltimore
  40. In season cherries
  41. Mango sticky rice
  42. Sore muscles
  43. Bourbon
  44. Honesty
  45. Good neighbors
  46. Bursts of creativity that feel like magic
  47. Moments of silliness
  48. Froyo on a hot humid day
  49. Kelly
  50. True professionals
  51. Cadbury caramellos
  52. Visits from faraway friends
  53. Women who support other women
  54. Productive meetings
  55. Dinner with Dad
  56. Memories of Pop
  57. Long drives with good views
  58. Picnics
  59. Crystal
  60. Family traditions
  61. My relationship with my father
  62. Poolside yoga
  63. Small favors
  64. Perspective
  65. Welcome home cuddles
  66. Fast friends
  67. A fresh notebook
  68. Erlinda
  69. The sleepy feeling after a full day
  70. Dunkin Donuts iced coffee
  71. A successful first webinar
  72. Laughs that make me cry
  73. A team that always raises the bar
  74. Working with people I love
  75. Scott’s questions
  76. Whiteboard sessions
  77. Team happy hours
  78. Friday night sleeps
  79. Finding new music I love
  80. Lazy Saturdays
  81. Food Delivery
  82. Berry season
  83. Fresh tomatoes
  84. Shopping trips with Mom
  85. Opportunities to help friends
  86. Partners who fill in the blanks
  87. Serendipity
  88. Work session with Steve
  89. Rendezvous and hugs at the train station
  90. A sense of humor

Magically Redefine Your Team Roles and Responsibilities

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Last quarter, a few things happened at once with our team at Allovue. 1) We were at a major inflection point, shifting my focus as CEO from mostly on product development to mostly on sales & marketing 2) Our CTO’s wife was 7 months pregnant, so we wanted to free up some of his time to spend at home once the baby arrived 3) One of our senior developers expressed interest in more autonomy and more responsibility. Here’s how we redefined our roles & responsibilities in a process that we completely pulled out of thin air and resulted in everyone on our leadership team being happier and more productive in their jobs. I’m telling you: magic.

I gathered the leadership team into the conference room and started by writing our names on the whiteboard. One at a time, we went around the room and each person named every process or category over which he or she currently felt ownership and responsibility.

After everyone listed responsibilities, we made a list called “No Man’s Land” for processes that we felt someone needed to own, but no one had named. (Note: We also put things on this list that people forgot to name earlier, because we figured this was an indicator of a responsibility that was not high priority or top of mind.)

This next step is the most critical ingredient of the magic. DO NOT SKIP THIS STEP. I went around to each person again and asked them to tell me “Yes” for things on their list that they felt were the right fit for them, and “No” for anything on their list that they wished for any reason was NOT on their list – you don’t like it, you don’t think you’re good at it, you think it’s stupid… whatever. “Yes” items got a check and “No” items got an X and were moved to No Man’s Land.

At this point in the process, everyone had a list of responsibilities that they loved and felt were appropriate for them to own. Now we had to contend with No Man’s Land: all the things we felt were important for somebody to own, but either no one did, or the person who owned it until now didn’t want to own it.

For the final step of this process, we went through each item on the list and decided to either 1) assign it to someone else on the team 2) find a way to make it suck less for the person who crossed it off their list 3) hire someone to do it.

And that’s when the magic happened.

As we went through the list, my team’s secret interests, skills, and talents emerged as, one by one, people volunteered to snap up items from No Man’s Land and take ownership of them. Rosalyn admitted to secretly enjoying close-reading of legal contracts, whereas I hated it and had been slogging through them. Jason volunteered to take on Sprint Planning, a process that was a total drain for Ted, but a natural fit for Jason. Jake took ownership of all front-end and design processes, which had been awkwardly and inefficiently split between me and the dev team. Ted reclaimed some technical processes, once we realized that a week of time could set up playbooks to automate all the stuff that was wasting his time.

At the end of this exercise, there were only four items in No Man’s Land, and they exactly mirrored the job description I had just written up for our new Venture for America hire. MAGIC. We went around once more to confirm that everyone felt comfortable with their new roles. Ted said, “Wait – that list is my job now?” “Yes…” I said hesitantly. A huge grin spread across his face. It’s a really good day when your CTO is happy.

This entire process took 45 minutes.

A few months in, here are some things that have resulted:

  • Our dev team velocity is higher than it has ever been. I attribute this to a combination of the fact that Jason enjoys Sprint Planning, and Ted has more time freed up to write code.
  • We have fewer errors in legal documents, because Rosalyn is a true Eagle Eyes and catches every. single. thing.
  • Rosalyn has also taken major ownership over customer on-boarding and project planning, demonstrating her unique strengths as a leader in this area
  • Jake has streamlined design processes, which has further contributed to increased velocity
  • My time has been freed up to focus on sales and marketing

Here are some of my key takeaways from this exercise:

  • Don’t let corporate dogma dictate the roles and responsibilities of your team.
  • Making people do something because “they’re supposed to” will drain your employees and slow down your team’s velocity. Sure, everybody has to do some things once in awhile that they don’t love… but make sure it’s really “once in awhile” and not “most of the time.”
  • Take a strengths-based approach. Hopefully, you hired people who are uniquely qualified to contribute to your team. Play to their strengths. They will thrive, and the whole team and company will thrive right along with them.
  • Listen when people ask for more responsibility. Don’t let talent and leadership sit dormant in the organization. This doesn’t mean promoting everyone to an executive position, but find ways to give people opportunities for leadership when they crave it. This might mean giving someone a leadership role over a single project or feature in the short term, and it might unleash new skills and talents you never saw before.
  • Just because someone “can” doesn’t mean they “should.” Founding team members tend to be multi-skilled individuals. It’s easy to assume that because someone is capable of doing something, it makes sense for them to keep doing it. Take inventory of these things regularly – can someone else on the team do it faster, with more joy? This goes back to the strengths-based approach: are people spending their time in the most efficient way, given the skills and talents of the team as a whole? Make sure that people who are uniquely qualified at high-value, mission-critical tasks are spending as much time as possible on those tasks.

I expect that we will return to this process as we grow, consistently reevaluating how team members are spending their time, and ensuring that we’re leveraging leadership capacity across the organization – because a happy, healthy, productive team is nothing short of magic.

If you try this magic process, or have done something similar, I’d love to hear about it!

How to Rock the Life Olympics

In the year after I graduated college, I was completely overwhelmed by all of the new challenges of adulthood that were rapidly hurled at me without so much as a syllabus to guide the way. I felt like every time I gained control of one area of my life (paid the bills! bought groceries!) other areas of my life lapsed into disarray and neglect (what? I have to go to the gym every month now?) It seemed like a very high stakes game with lots of rules and no playbook. I identified five different areas that I considered critical to a happy and healthy adulthood and started calling it the Life Olympics – partly inspired by the five Olympic rings, partly inspired by the seemingly Herculean effort involved in mastering any one of these areas day-in and day-out, let alone all five of them.

responsibility10

From one of my all time favorite blogs: Hyperbole and a Half: This is Why I’ll Never Be An Adult. http://hyperboleandahalf.blogspot.com/2010/06/this-is-why-ill-never-be-adult.html

The Life Olympics started out as a way for me to get my head around the different parts of who I am, but it has evolved during the past six years into a system for reflection and a framework for goal-setting and self-improvement. Below, I outline my Life Olympics categories and what they mean to me, but I encourage you to modify the categories based on who you are and what’s important to you.

Career

This is a big one for me, and usually dominates my time and energy. This category is pretty self-explanatory: this is your professional/work-life. What are my professional goals? How do I perform as a member of my team or company? Am I fulfilled by the work I do? If not, what am I doing about it? Also: has work been consuming my life in an unhealthy way?

Health

In this category, I include everything related to my physical health: exercise, nutrition, weight control, sleep patterns, and general health maintenance like going to the doctor and dentist for annual check-ups. This is a weird one for me. I’m a generally healthy person. I don’t smoke. I’m active. I eat pretty healthful food. I regularly go to yoga. I’m also lucky enough to have good genes that help me maintain a decent weight and good teeth. I could be healthier, but I’m also learning to come to peace with the fact that I’m never going to be super skinny, because I love pizza too much. And ice cream. And butter. And pasta. And wine. And just generally rich, delicious, food-as-entertainment dining experiences. Sometimes, the Life Olympics is about accepting yourself as you actually are, rather than constantly striving for some idealized version.

Relationships

Family, friends, and romantic partners. Am I making time for loved ones in my life? Do I call my parents regularly and keep in touch with friends from college? Am I making a genuine effort to not die alone? Do I generally make time to spend with people so that I don’t fall into an all-consuming abyss of work?

House & Home

Bills paid? Fresh sheets? Clean underwear? Taxes filed? Basics. This one used to really be a bare minimum for me (will Mom have a stroke if she visits?) but I’m starting to take this category to the next level now. I hired a cleaning lady this year with extra rental income from my house, so now I have more time to focus on decorating my house and making it a warm and inviting place to live and visit, surrounding myself with pieces of furniture and art that I love. Next year, I might try to keep a plant alive. Baby steps. As you reach an income threshold somewhere above hand-to-mouth, this can also be an area where you start thinking about savings, investment, and general financial planning.

Spirit

This is my most-neglected category, so this year I’m being especially thoughtful about this area of my life. This category is different for everyone, but it’s basically anything that makes you smile on the inside – things that feed your soul and help you find peace in the most chaotic corners of your mind. For me, this category is about indulging my creativity and insatiable wanderlust, as well as making time for quiet and meditation. My love of theatre, music, reading, writing, travel, and yoga fall into this category: all the things that make me the fullest version of myself, yet the same things that I ruthlessly abandon as soon as (work) life gets hectic. This year, I’m working to observe the impact that nurturing this part of me has on other areas of my life, to prove its importance to myself.

Reflection and Goal-Setting

For the past few years, I’ve reflected on these categories and assigned a medal award for each: gold, silver, bronze, or “did not place” if it was a super rough year in that area of my life. Consistently, Career has trumped everything else in my life, which did not make me happy. I love running Allovue, and I love my team, and I’m obsessed with our product, mission, and customers. But it can’t be my whole life. It can’t be all of me. This year, I decided to try something different to fix this.

This year, I started treating the goal-setting process in the other four categories of my life with as much time and thoughtfulness as I do for work. At the beginning of the year, I created five annual goals for each category – 25 goals in all. Some of them are things I could do in one weekend, and some of them are more long-term builds. Every quarter, I revisit my annual goals and set quarterly goals, and each month, I revisit my quarterly goals to set monthly goals.

This may sound like a lot of goal-setting, but it can be done over a quiet cup of coffee or tea on a weekend, and it helps keep me mindful of what I’m working towards. I also find that chunking things out by quarters and months make bigger goals much more manageable. For example, one of my Spirit goals this year is to read 30 books. That’s about 2.5 books each month, which is totally manageable, but if I don’t keep track, all of a sudden it’s December and I have 12 more books to read (which is what happened last year, and I did nothing but devour eight books over Christmas vacation). This year, I’m exactly on track, and I can think about which books I want to enjoy each month.

And that is pretty much how to rock the Life Olympics.

There are no winners and losers in the Life Olympics – it’s all about how you play the game. Of course, I’m going for gold.