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.


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


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.


From one of my all time favorite blogs: Hyperbole and a Half: This is Why I’ll Never Be An Adult.

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.


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?


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.


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.


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.

Everything I know about being a CEO, I learned being a teacher


“How can you be a CEO when you were just a teacher?”

This is one of the most common questions I have fielded as the CEO and founder of Allovue, an early-stage financial analytics company. Initially the question offended me; I prickled at the insinuation of all the worst teacher stereotypes: teachers aren’t as smart or shrewd as other professionals, teachers are lazy, teachers are fluffy.

Now, I’m amused by the question. After all, teachers are the unsung CEOs of the world. Teachers manage hundreds of people every day (who are not paid to show up!) Teachers prepare and present 4–6 hours of unique content every day, and are evaluated based on those hundreds of students’ ability to process and retain this new content. Teachers make all their own agendas, PowerPoints, and reading materials. They often buy their own presentation tools and office supplies — for over a hundred people. Sorry, no T&E reimbursements! They make their own photocopies of materials they created or purchased themselves. They give individualized feedback to over a hundred people on a regular basis. Hey, CEOs — when was the last time you reviewed and evaluated the daily work of +100 employees after doing all your own work and meetings for the day? And don’t forget to call all of your employees’ parents at least once a week to let them know how they’re doing at work! Great teachers are virtually superhuman masters of management and logistics.

I’ve come to realize that most of my favorite management strategies were fire-tested in the classroom, not a boardroom. Having taught students from kindergarten age up to the graduate level, I’ll let you in a little secret: managing adults is not all that different from managing children.

Public praise, private punishment

This is a staple of classroom management. Can you remember a time that you were called out in front of your peers for doing or saying something wrong? Can you feel your cheeks getting warm just thinking about it? Now, think about a time that someone praised you for a job well-done in front of all your colleagues. I bet your chest is still swelling with pride. This is a pretty basic tenet of human psychology: most people appreciate public recognition for good work, but feel humiliated by screwing up in front of their pals. Publicly chastising people for mistakes might create results in the short term, but it’s no way to build a strong culture in the long term.

As often as possible, we make an effort to let our team know about all the awesome things their teammates are doing — we also share a weekly newsletter with team shout-outs and appreciations, ranging from small helps (“Thanks for giving me a ride home”) to big wins (“Great job closing that sale! Coffee for everyone!”)

On the contrary, if something is going awry with process or performance, we address these issues privately with team members, and we focus on figuring out why something isn’t working and what steps need to be taken to fix the problem. It is difficult to consistently do this without egos and finger-pointing. We are not perfect at it, but couching these discussions in terms of finding solutions instead of allocating blame goes a long way.

Give credit, take blame

As a general rule, when something good happens, my team did it. When something goes wrong, it’s my fault. As the CEO, you have little to lose by accepting blame. It takes pressure off the team and frees up their mental space to focus on solving the problem. Are you sensing a theme here? People don’t function well when they’re embarrassed or scared.

As for giving credit, let’s harken back to Obama’s “you didn’t build that” decree. No matter how much of a 10x-programmer-visionary-wünderkind you are, it’s extremely unlikely that you built something great alone. Give credit where credit is due — and then some. Elevating others does not diminish you. Take every opportunity to credit your team, investors, advisors, and customers because this is an all-ships-rise-win-win situation.

Bring cupcakes

I don’t care if you are 5 or 50 — people love cupcakes. I have studied this extensively, and the effects of cupcakes on a classroom or office are the same: good cheer and a burst of productivity. We are lucky enough to have the gourmet cupcake shop La Cakerie down the street from our office and we are frequent patrons. Birthday? Cupcakes! Engagement? Cupcakes! Good press? Cupcakes! Thursday? Cupcakes! Celebrate each other. Celebrate wins, big or small. Celebrate just because you are all in this together, doing the hard things, fighting the good fight, and goddamit, you deserve a cupcake.

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.

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.

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.

The Last 5 Years in Baltimore (1)