Plain Plain Casey Jane

Over the past few years it’s become trendy to be anti-New Year’s Resolutions. People seem to genuinely dread the January tradition of reflecting on the previous year and setting new goals for the year ahead, and when the types of goals you’re making for yourself are things like “stop being fat” or “make more money” or “be happier” well, I can see why. 

I, however, am not one of those anti-Resolution people. I love the last week of December when the holidays are over, I’ve spent time with friends and family and away from work, and I’m eager to get back to my routine and yes, map out some new goals for myself. If you’ve been a reader of this blog for some time you’ve seen me iterate on my goal-making process (actually, the very first blog post I wrote here when I was 25 was about goals – and then I wrote about it again here and here, and sprinkled throughout many others) and even abandon it a few times. This year I’m really excited about what I’ve come up with, and I wanted to share it as a framework for anyone looking for inspiration, and also as an accountability tool for when that honeymoon phase inevitably ends and I start looking for excuses to quit on myself. 

I’ll let the others give their reasons agains New Year’s Resolutions (one I actually like, if you’re looking for that side of the argument, is laid out in this post from Tim Ferriss) but here are my top three reasons why I enjoy them: 

1. Setting goals starting January 1st ensures I’m refreshed and rejuvenated before I start tackling new things. Goals are hard. They take work and progress can be slow to see. I find that I’m best set up for success if I set goals for myself that begin after I’ve had time to rest, and the holidays for me are exactly that. If you work in late December or find the end of the year particularly stressful, choose a different time when you can pause the regularly scheduled programming of life, contemplate your next steps, and then come back with a renewed sense of purpose and energy. 
2. Setting goals helps me know what to say yes to, and more importantly, what to say no to. I’m still in my twenties, which I firmly believe should be the decade of “yes” contrary to so much advice out there about the importance of saying no. And yet, I can’t say yes to everything. If you’re like me and tend to get swept along by the tides of all the things you could be doing and maybe want to do, setting goals is a great way to give yourself a defined lane to swim in. If something comes along that helps you with your goals, go for it. If not, think twice about what you’ll be giving up by saying yes to it (because every yes to one thing is a no to something else). 
3. Setting goals helps me get clear on my values. Part of the reason goals can feel overwhelming is because we don’t think carefully about the motivation behind the goals we choose. Are you selecting goals that resonate with you, or are you selecting goals that the world tells you you should want? On top of that, sometimes we select goals that aren’t really in our control. Getting six-pack abs is not ultimately in your control, as it’s the result of too many external factors that you don’t have any say over. Doing fifteen minutes of core work every other day is a much less sexy but ultimately more motivating and attainable goal that might result in six-pack abs but will definitely be something you can track and measure. 

I always start goal-setting by revisiting my core values. If a goal doesn’t fit neatly into a core value, it becomes a hobby, not a mission. I can still pursue it, but only if I enjoy it, and I don’t measure my progress around it. A great example of this is rock climbing. I’ve gotten into bouldering over the past year and while I enjoy it, it doesn’t truly impact me if I stay a pretty mediocre climber for the rest of my life, so there’s no need for me to set a number of times I should be climbing per month or a level of difficulty I should achieve. It’s just for fun. 

I have twenty goals for 2023 (I know, I’m aggressive), four for each of the most important areas in my life, one for each quarter of the year. I won’t go into each of them in detail, but here’s a broad outline of what I’m focusing on and hoping to bring about this year: 

Work – ownership & leadership 

This year I will have been working for my company longer than I have been in any other job combined, which is neat and unexpected. After two years of wandering hopelessly through the virtual world of the pandemic, I finally came into my own in this role last year, so now I’m shifting into high gear to fully establish myself as a leader in my industry. I’ll be in charge of developing strategy for the future of our firm, running a hiring process to expand our team, and I’m also pushing myself to do more external events, especially ones focused on bringing more women into venture capital and the start-up ecosystem more broadly. 

I question daily how I wound up in this position, working in a finance-heavy male-dominated job, but the answer remains that it’s become something I’m deeply passionate about, truly enjoy, and want to be the best at it. 

Writing – consistency in my creativity 

While I always like to have several writing projects going on at once (this blog included), the one I’m most excited about this year is to write a collection of scary short stories. I am OBSESSED with horror movies, but not so much horror books. While I’ve read a few that are excellent, most horror novels feel pretty basic, and I’ve found myself telling Bobby that I could write something better enough times that I think I should actually give it a go. Instead of trying to write fiction daily, which I did last year to get myself back into the habit, I’ve found larger chunks of time on the weekends that I’ll spend focused on fiction, so that my brain isn’t constantly switching between things all day long. 

Also, I think it’s sweet that my husband is so excited to read these stories and watch all the gory horror movies with me (as research, obviously) even though he hates all things scary. He’s a keeper. 

Fitness – feel fitter in my 30’s than I did in my 20’s 

This is really an area I’ve struggled with the past few years and am recommitting to in 2023. When I was 18 I could effortlessly do all the things I wanted to on minimal sleep and subsisting mainly on French fries, but that’s not my reality anymore. The isolation of the pandemic made me much more of a homebody and I got out of the habit of being active consistently throughout the day, leaving me with less energy and some unnecessary weight. 

This year I’m doubling down on my commitment to healthy living (starting with dry January, which I’m successfully halfway through!) and I’m also reaching out for a lot of help. I’m working with a nutritionist, talking to my doctor about different health factors I want to focus on improving, and getting lots of support and accountability from my friends who know that it’s better to ask me to join them for hikes and yoga classes instead of happy hours. 

Relationships – deepening bonds 

Since I moved to DC in 2020 I’ve been dedicated to meeting new people and making new friends. Now that I have a solid group of amazing people here and abroad, I want to spend my year pouring into all the people I love most. For my marriage, that looks like starting a practice of weekly meetings to check in with one another about our relationship, our shared responsibilities, and how we want to incorporate fun into our days since we both tend to get easily mired in working constantly. For my friends, that looks like hosting a quarterly game night and connecting different awesome people to one another around a fun experience. For my family, that looks like engaging fully during the holiday seasons and not letting work or other distractions take over my limited time with them. 

Adventure – all the sunshine 

I was shocked to realize I haven’t been out of the U.S. in almost 8 years. My passport expired and I didn’t even realize! So I’m fixing that problem by using some of my wedding registry funds to plan a trip with Bobby to South America. That’s all the planning that’s been done so far but I’m excited to make it happen.

Also this year I’m officially labeling us a “outside family” and planning to spend way more time exploring the outdoors. I’ve committed to Friday morning walks so I can spend more time outside each week, and have a list of destinations around DC for hiking and camping. 

My honeymoon phase of conquering all the goals is still in full effect, but I’m not worrying about when it will end. I’m soaking up the pleasure of the energy of it, the extra drive it gives me, and I’m celebrating every small win I notice along the way. I know it won’t be like this all year, and I’m ok with that. I know I won’t achieve all twenty of my goals this year, and I’m ok with that too. I like the idea of being ninety years old scrolling my iPad with the font blown up extra-large, reading my old blog posts of all the things I wanted to accomplish in my life, the things I did and the things I dreamed of doing, and all of the unexpected things I never could have imagined in between. I like the feeling of always having something to work towards. 

The Fourplay Social Investment Thesis 

As someone who just celebrated her one-year wedding anniversary, it probably seems strange that my first angel investment was in a social app for singles. But when I met co-founders Julie and Danielle and learned what they were building, what I ultimately decided to invest in was their larger mission to improve the way we connect with one another online and make the internet a kinder place to form relationships. With the ever-increasing hype this year about web3 and living in the metaverse, I want to be part of crafting a world—both virtually and in reality—that is better for our mental health and improves our ability to meaningfully interact with one another in a variety of ways. I believe that Fourplay Social will be a part of what moves us closer to that type of future, and I’m excited to be on that journey with them. 

Fourplay Social (Fourplay) is a app where single friends pair up to match with other duos (kinky, right? Just kidding, it doesn’t have to be.) Founded by two best friends and headquartered in New York, Fourplay is building a healthier and more enjoyable experience for singles where first dates are more social and less stressful. 

I invested in the company via a SAFE (simple agreement for future equity) on Wefunder, an equity crowdfunding platform where anyone (including non-accredited investors) can support startups and get access to equity. Depending on when you read this, their raise might still be open for investment if you want to join in on the deal! 

The Current State of Online Dating 

With an endless number of apps in the market already covering everything from quick hook-ups to dating for farmers (I mean seriously, check some of these out) it’s easy to dismiss the industry as over-saturated and, to be fair, it’s not easy building something new in an already crowded market. But major dating apps have one of the worst net promoter scores (NPS) of any industry, with a ridiculously low likelihood of being recommended to a friend by their users. Dating apps are less popular than airlines, wireless carriers, healthcare plans, and TV services, meaning people are more likely to recommend their phone plan than their dating app, which is just a ridiculously low bar for improvement. Additionally, in a recent survey by NEA, 80% of respondents reported being somewhat or very open to trying a new dating platform, “confirming the opportunity for a new entrant.” 

While I’ve never swiped for a romantic date, I did sign up for Bumble BFF in 2021 to make friends in a new city during the pandemic. I was an active member for only three months before I deleted the app. 

All the friends I met on the site seemed nice, but I didn’t truly hit it off with any of them and we didn’t stay in touch. It became clear that, for me, the effort of scrolling, swiping, small talking, coordinating, and repeating wasn’t actually worth the outcome, so I deleted the app. This was a relatively easy decision since I had enough existing friendships to sustain my need to socialize and I knew it was just a matter of time before I made more friends the “old fashioned way” instead of spending all my time on an app. But I can see how this would feel different if what I was looking for wasn’t a buddy for yoga class, but a life partner. So many people in my age group feel increasingly desperate to find ways to genuinely engage with each other, which keeps them tethered to a dating app or online experience that irritates them at best or damages their own self-image and mental health at worst. 

This is the problem Fourplay is trying to solve, and it’s got a vast market to operate inside of. By 2026 it’s predicted that over 300 million people are expected to be paying for online dating worldwide, and nearly 10 million of those users will be in the United States (Tinder alone currently has 8 million monthly active users). The largest player in online dating is the conglomerate Match Group, born out of Match.com, with a $15B market cap and nearly $3B in annual revenue. Match Group has gobbled up most players in the online dating space, each with a different value proposition but none that match the process Fourplay has created, making the company a solid acquisition option for the future at what would be a lucrative exit if Fourplay can grow and retain enough users (Tinder was acquired in 2021 for $1.7b) to be an attractive option. 

Introducing A New Way to Double Date

A growing percentage of people have swiped their way to success. I know plenty of couples who first met online, although it’s always interesting to me to hear what they tell strangers or distant connections (like coworkers, for example) about how they first met. Many couples who met through a dating app lie, especially if they are talking to older or already married people. The stigma of online dating remains strong even as 3 in 10 Americans say they’ve used online dating apps and 12% of them have married or been in a committed relationship with someone they met online. So much of the online dating experience feels isolating which is an ironic conundrum for an event that by definition is supposed to take place with another person. Instead, it’s more common these days for a single person’s dating life to exist primarily behind the confines of a screen, with hours of alone time racked up before hearing another person’s voice or meeting someone in person. 

Fourplay has built a product where users can team up with a friend, create a shared profile, and match with other pairs of single friends. The product is focused on singles age 18-34 and initially launched in New York City, where 13,000 people are already using it (and the waitlist across the U.S. is another 12,000 long). Over 40,000 matches have been made so far in NYC and that early traction has led to the founders being featured on LIVE with Kelly and Ryan, CNBC, and multiple other sites (see here and here for starters). 

The company was founded by Julie and Danielle, two best friends who have backgrounds in healthcare and were frontline workers during the pandemic, so it really doesn’t get more badass than these ladies. Clearly they understand dedication, commitment, and hard work, which are all characteristics that I believe are critical to becoming a successful founder and can’t be taught overtime the way financial or operating skills can. Neither of them are “traditional” entrepreneurs – they didn’t go to business school or spend time at consulting firms, and while most people see this as increased risk, I know from personal experience how much being an outside can help when building something new. Having spent time with them I also know they are smart and driven enough to quickly learn what they don’t know, and that their unique perspectives will help them build a product that’s more accessible and desirable, not something that any MBA student could cook up. Statistically speaking, underrepresented founders outperform white men over time, so it’s even more practical to support a fully female founding team.

The MVP that first launched in New York gained solid traction and positive reviews on the App Store, even with some clunky UI/UX. The team used their first raise to bring on a technical co-lead to help rebuild the app with a new and improved flow and feel that is currently being tested in beta before being rolled out to new markets. 

Why I Decided to Invest 

As we continue to push more and more of our lives online, dating apps will expand and evolve, offering market share potential that can be captured by creating a community that is safe and less stressful than what’s currently available. 

At a friend’s party in Brooklyn earlier this summer the topic of dating came up in conversation, and every single person in the group had a horror story from their experience with a dating app. Some were amusing in hindsight, like one story about a girl who refused to leave the restaurant because it was raining (even after she was offered an umbrella) so forty-five minutes of drinks turned into nearly four hours of awkward small talk. Some were creepy, like one guy who repeatedly asked for more pictures of my friend and, when she refused, said he was going to find her and kill her cat. Some were mundane, like being ghosted or showing up to see that the person you’d agreed to go bowling with looks nothing like their pictures. Honestly, I’m sure there were stories that went unsaid and were even worse. A Pew Research report shows that 60% of female users ages 18 to 34 have had someone on a dating app continue to contact them after they said they were not interested, while a similar share (57%) report being sent a sexually explicit message or image they didn’t ask for. 

When I mentioned to the group at the party that I’ve never used a dating app, most people were shocked, and more than a little bitter. Not one person had anything positive to say about their online dating experience. 

In the 2022 NEA study cited above, nearly 80% of respondents said they would be “very open” to trying a new dating app, and yet Tinder, Bumble and Hinge continue to grow their user bases. It’s apparent that the time has come for a new way of not just matchmaking online, but actually dating online, because dating shouldn’t be something people dread doing. And Fourplay is not just Bumble for double dates. It’s building a unique interface and system for GenZennials (people 18-34) to be social online. To me, this is a way more exciting way to build the metaverse than through online gaming or social media. Fourplay is designed to foster relationships that can exist within the boundaries of our digital lives or move into the real world if we choose, without the fear of negative interactions or the pain of awkward encounters, because users are going through the journey with their close friends.

The user strategy of dating as a team produces a flywheel that will beat the existing customer acquisition and retention problems plaguing other prominent dating apps. 

One of the hardest parts of building a dating app is the fact that if you’re successful, your customers eventually leave. As Hinge says in its marketing, the app is “designed to be deleted.” This leads to a high level of churn (having to replace users who leave) and can decrease growth. If the goal of a dating app is for users to meet their special someone and stop dating, eventually users will either actually do that and delete the app or will get tired of all the failed dates and switch to a different dating source. 

Fourplay combats this problem with its process of double dating, expanding their user base by requiring each person who joins the app brings a friend. If a double date is successful for one of the friend pair, the other can team up with someone else and keep dating, continuing to bring new people onto the app and building up a defensible moat against other apps that try to copy their style because if people are already double dating on Fourplay, they won’t switch to a different app if they’re friends aren’t there. This is also a great way to save money on paid acquisition channels that most dating apps use to find customers like Facebook and Google ads, for example, which can be extremely pricey. 

Early traction and super-fan feedback validates this idea, and having two diversified revenue streams will help the app reach scale.

Seeing the waitlist for the app continue to grow, as well as the number of connections made in New York, makes me excited to be an investor in this company. The app has received worldwide attention and has over 100 positive reviews on the App Store (4.5 stars) after launching earlier this year. Fourplay Social definitely has what I call “proof of life” data: it has shown that its building something people want, and are willing to pay for. Now they have to put the rest of the pieces in place to scale that idea into a thriving business that can serve more people and continue to iterate based on their users wants and needs. 

The company makes money through a typical SaaS subscription and ad model where users pay a monthly fee to use the app and the app runs ads. Both revenue streams are proven out and sustainable, as long as the app reaches a high enough number of users with a minimal amount of churn to cover expenses and continue to grow. 

The Risks 

Expanding a marketplace from city to city is an action that doesn’t scale and could break early success if it’s not done strategically.

In my opinion this is the biggest unknown of this investment, and the biggest risk I’m taking in making this bet. For a marketplace to work there needs to be buy in on both the supply and demand side. So if I’m a woman looking to date men and there are only 3 men to choose from, I’m not going to have a great experience dating on Fourplay. Similarly, if I live in Ohio and I want to try dating on Fourplay, I won’t have a good experience if there’s only one other person in Ohio for me to match with. Bringing people onto a platform takes time and it takes money, usually in the form of doing things that don’t scale like hosting big events, running marketing campaigns, and paying influencers to be early users and to tell their fan bases about a new product. 

It’s important for founders to do things that don’t scale sometimes. It’s the little details and the extra effort that can make a product really sticky in a new market, but if you have to do it too much you don’t have a business and you’re just wasting money (see: Uber). This is where the network of advisors and advocates that Julie and Danielle are seeking advice and expertise from will be critical, because having mentors who have scaled successful startups and understand the details of customer acquisition and retention will help them launch past the cold start problem and get to their first dedicated users in new markets. I’ve already seen this in action through the team’s decision to launch in the collegiate space next, focusing on universities to reach critical threshold faster than would be possible in city markets more broadly. This strategic shift again reiterates the deep thinking and intelligent support system the founders have engaged to build their company correctly. 

Two non-technical first-time founders building an app will make iteration and future development difficult. 

While initial reviews of the app have been overwhelmingly positive, the main criticisms have to do with the app crashing unexpectedly and some issues with the onboarding flow. These are technical issues that require someone with coding and development capabilities to address. While the founders are not technical, their first hire is a VP of Engineering who has been brought in to address these issues as well as other bugs and continue to build out the platform. 

I’m impressed that despite these glitches most users continued using the app, and that the actual UI/UX has been reviewed positively. Again, I think this shows the level of deep thinking the two founders are capable of and the fact that they will continue to focus on their mission of creating a better online dating experience, which will embed itself into every decision that’s made. And while it’s obviously incredibly important to have the person actually building the thing to understand the nuts and bolts of app development, I don’t think it’s a requirement for founders. This is one of my core theses as an investor – I’m good with investing in excellent non-technical founders, and I think it’s important. Lots of engineers look, think, and act the same, and I don’t want that subset of people to be responsible for shaping every aspect of our future. Also, it takes a lot to run a successful startup, and it’s good to have a diverse set of skills on the team especially early on, which means not everyone needs to be in the code to move the business forward. 

What Will the World Look Like if This Works? 

Relationship building is increasingly becoming an online experience, and that experience right now isn’t a satisfying one. Facebook claims to be the epicenter of human connection and is going all in on its idea of a metaverse, but the problems around Facebook’s monetization strategies and the addictive qualities of social media more broadly are well documented and contradictory to the essence of what it means to connect with someone. Dating apps tote strong user metrics but no one speaks positively in real life about their online dating lives. There is so much room for improvement and I think what Fourplay is building, with its focus on a culture of safety, communication and connection fills a gap in the market. 

It will be critically important for the success of Fourplay that they don’t build a product that is just “Tinder for double dates” or any other incremental change to the existing big picture of online dating. Because the incumbents in the space are so large and well-resourced, it would be too easy for them to catch on to the success of a double dating feature and add it to their existing product, creating an overly competitive environment that a new app won’t be able to thrive within. 

But I believe what Fourplay is building is bigger than that. Everything about how online dating currently operates makes it difficult for anyone who takes it “too seriously,” and instead caters to a feeling of being “just for fun,” which in turn leads to a minimal level of commitment to doing the sometimes difficult work of building a relationship with a stranger. It starts to feel more like a game than a meaningful interaction, which opens the door for bad behavior and an overall sense of apathy. 

Fourplay isn’t an overly serious app, and it’s not just for people looking to meet the person they will spend the rest of their lives with. By using a double dating format, fun is embedded into the concept, as reflected in their marketing of “a night with your best friend is never a night wasted” even if the date itself is a bust. In addition to fun, the entire process is imbued with a sense of safety first (buddy system at its finest) and being a place for actually dating online, not just matchmaking. This gives Fourplay the potential to grow into other areas overtime. 

There are still plenty of logistical questions that the company (which is still in its early stages) will need to think through, and while they don’t have the answers yet, I’ve been extremely impressed with the level of strategic thinking Julie and Danielle have conveyed and am confident they’ll come up with compelling answers to these questions, like how to get enough men to join to sold the gender gap problem and how to provide a space where multiple relationship needs can be met. 

Beyond my support of the company itself, I invested because I want to see a world where more women get the venture backing needed at an early stage to build startups. I want to see more fully female founding teams. I want to see women with backgrounds in healthcare and education and fashion and non-profits moving into the tech ecosystem and being seen as credible and taken seriously. I want more women-run unicorns and more women as serial entrepreneurs. 

That’s why I invested in Fourplay Social. 

I started working in venture capital in 2020, running operations for an early-stage VC firm focused on fintech. In 2021, I started learning about angel investing and now in 2022 I’m excited to have made my first personal investment. 

At VC firms, memo writing is a best practice, forcing each investor to articulate their thoughts about a startup and investment decision that’s tangible and shareable with the rest of the team for discussion and consensus. As I sharpen my skills as an investor, I’ve decided to write memos about each of the companies I personally support and share them to this blog as both a catalogue of my thought process and an investing track record. 

One of my goals in writing these memos is to become a better thinker about the future and the tech that will build it so that I can make better bets over time. If improving is the goal, it also means that at some point if I reach that goal I’ll look back on these initial memos and realize just how much I didn’t know. On one hand, that’s great! It will provide proof that I’ve grown, matured, and learned. But it’s also embarrassing to think of all the investors out there far more advanced in their journey than I am who might happen across this thing that I’ve put my name on and think “this girl has no idea what she’s talking about.” 

And maybe they’re right, and maybe that’s ok. It’s scary, but it’s also reality. While plenty of memos written by venture capitalists have proven true (for example, you can read some of the most legendary ones from Bessemer Venture Partners here), the vast majority of startups ultimately fail. So it’s a bit like setting myself up for failure to post my optimism about them so publicly. But it’s also the most natural and enjoyable way for me to keep doing what I love: thinking deeply about how to make the world a better place, supporting people doing that work, and writing about it. 

If you’re a fellow angel investor or VC (or are otherwise connected to the entrepreneurial ecosystem), I’d love your feedback on how I can improve these memos and my investment thought process more broadly. If you’re a founder building something that fits my thesis (which right now, very broadly, is making the world a better place), leave a comment and let’s connect! 

The first investment memo will drop in August. If you don’t want to miss it, make sure you’re subscribed to the blog. 

*Note: these memos and the investments I describe reflect my personal opinions and are not associated with my day job or company. This is in no way, shape, or form, investment advice. I’m not a professional investment advisor, nor do I play one on the internet. 

I went to my first Crossfit class in 2016. It was an eight-week intro course for women and from the first hour I was hooked. I joined a gym and started going at least five times a week, which I continued to do for the next 4 years. Many of my best friends are from Crossfit; one of them even became my husband (hi Bob!). I also saw a lot of growth over those four years as a “Crossfitter”. I became stronger, fitter, more energized, but I also became more social and developed more grit. 

Still, I’ve always struggled to feel satisfied with my progress in the gym. During those four years my back squat weight increased, but never to the number I wanted it to be. I couldn’t string together pull-ups, let alone attempt a muscle up. My arms and legs grew more muscular but overall my body was still basically a breadstick, and I couldn’t seem to convince myself that I’d made any meaningful progress after years of dedicated work. 

And so, when gyms reopened after being closed at the start of the pandemic, I decided not to go back to Crossfit. I was tired of the sore muscles and torn hands and scaled workouts and watching other people make more progress than I was. So I quit. I started running and doing yoga to stay active (and also spend a lot more time being inactive, but that’s probably best unpacked in a separate blog post…or with my therapist…). 

This year I’ve gone back to Crossfit-style workouts and have been blown away… by how badly I suck. 

I mean wow, I thought I was bad before? I was amazing before! 

In 2019 I was frustrated that I couldn’t string together pull-ups, and now I can barely get my elbows to bend. In 2019 I was mad at myself for how slowly I completed Murph (which includes 2 miles of running, in addition to 100 pull-ups, 200 push ups, and 300 squats), and now if I run for a few minutes my heart starts to feel sort of explosion-y. Of course this has led me to shame spiral a bit because if you’ve met me or read any of this blog you know I’ve got some perfectionist/control freak tendencies (it’s ok, admitting it is the first step). I can’t believe that I’ve let so much of my fitness disappear, and it’s intimidating to think about how much work I’ll need to put in to get it back. 

I think this is a universal problem not just in fitness but in life. I can’t tell you how many friends of mine have refused to take a Crossfit or yoga class with me because they aren’t “enough”; not in shape enough, not flexible enough, not thin enough. The entire time I was doing Crossfit I was comparing myself and my gains to everyone else’s and it blinded me to any progress I was actually making on my own, to the point that I eventually got so fed up with being “stuck” that I gave it up altogether. Only after backsliding for an entire year could I see clearly how much progress I had made in the four years prior, and how much I had lost by stopping. If I had been able to appropriately recognize and celebrate the small wins, I would have been so much better off than letting my self criticism cloud my ability to see the situation clearly. 

My belief that I lack enough-ness has held me back in almost every area of my life. My writing folder is cluttered with abandoned drafts that I convinced myself were terrible. In fact, I wrote the first draft of this exact post several months ago, told myself it was shit, and only just now stumbled back across it and realized it wasn’t as bad as I thought it was. By being hyper focused proving on my own growth I’m constantly sabotaging my own chances of success. 

And yet, I’ve convinced myself time and time again that my overly critical brain is actually a strength and not a weakness because if I didn’t worry about doing great things I’d never get off my butt and do anything. This is a fallacy. If I stopped worrying about the outcome and instead enjoyed the process, I’d save countless hours fretting about my lack of progress, and would be able to get over my fear of producing poor work and actually get shit done in the moment, not months from now. Not only is this a super frustrating realization for someone who wants to have a successful life, but it’s also a super frustrating realization for someone who wants to have a happy life. I don’t want to always have to look back to understand that things weren’t as bad as they seemed at the time. I don’t want to live a good life in retrospect, I want to live it now, in the present moment. 

In Shirzad Chamine’s book Positive Intelligence, he describes this problem as one of many mental saboteur’s that keep us from our potential. All of our negative emotions, Chamine argues, are self-sabotaging. That includes the emotions we think of as overtly negative, like being judgmental or controlling, but also the emotions that we’ve convinced ourselves are helpful, like worrying over something or attaching our self-worth to our achievements. We tell ourselves that without these emotions to drive us forward we’d become lazy, or somehow be worse off. 

But I don’t want to live life through a pessimistic lens, believing that people are only capable of greatness if motivated by a fear of failure or a need to prove themselves. Instead, I’m choosing to believe that human beings are driven to learn and create by an innate sense of curiosity, collaboration, and empathy that I also possess and can harness instead of resorting to worry and anxiety. 

So despite my huffing and puffing and the little gremlin in my brain telling me I’m no good, I’ve started running. I signed up for a 10k race in October and five days a week I open up my Couch-to-10k app on my phone and run for about 30 minutes. And despite my worry that this blog post is trite and therefore I must be a terrible writer who is silly to post things out loud where other people can read them, I’m sharing this article now instead of letting it languish on my laptop for another few weeks/months/years.

I’ve been told that in marathon running there is a common phrase, “pain is inevitable, but suffering is optional.” How true of our everyday lives as well, and what a necessary reminder that suffering only slows us down. 

This week I met an amazing founder who is building a social e-reader called Monocle, where friends can connect with one another to share thoughts on books while they’re reading them, instead of having to wait until after the fact (like in a book club meeting) or disrupting the reading experience and putting the book down to comment (like on Goodreads). The features are similar to the highlighting and note-taking capabilities on Kindle, but shareable with select friends, so you aren’t inundated with notes from strangers but only see thoughts from the people you care about. You can port e-books you currently own to the app or buy through them directly.

The product is currently in beta, but you can sign up now to get free access when they launch! I’m excited to be an early user and would love to read with my readers.

That’s all! Happy Friday.

We live in the information age, where the internet gives us access to virtually all human knowledge (and even knowledge beyond human knowledge), and where anyone can learn about or teach on any subject they have interest in. I’ve learned about creative writing from novelist Margaret Atwood, wine appreciation from wine critic James Suckling, and presidential history from biographer Doris Kearns Goodwin all from Masterclass. I’ve taken knitting classes, yoga classes, and business classes from YouTube. I’ve used virtual learning to get CPR certified, to attend venture capital courses, and as part of my master’s program. 

The ability to learn from our laptops has opened endless possibilities, but as we all know from Peter Parker’s uncle Ben(ish), with great possibilities comes great problems. The rise of misinformation and fake news is certainly the most obvious of these problems, but even reputable news sources struggle to avoid junk information, and we consumers struggle to identify it. This has led to what the World Health Organization has officially titled an infodemic.

Timoni West, the VP of AR at Unity, recently said this in a Fast Company article about the biggest tech trends of 2022: 

“While I think this is the most important thing we need to talk about as a species, it will likely be in nascent or shallow stages in 2022: real understanding of how online communication changes perception and understanding. We live in an era where adults who have been fully vaccinated from measles, mumps, and polio from infancy who are refusing to get one vaccine now. We see people vastly misunderstanding new tech, like what an NFT actually is, or the limitations of augmented reality. We need better ways of communicating complex ideas.” 

Better ways of communicating complex ideas. When I read that statement I wrote it in all caps in my notebook and I’ve been noodling on it ever since because as much as I appreciate what the internet has allowed me to access, I also know first-hand how difficult it can be to learn virtually. 

At the end of 2019 I accepted a job offer to step into the COO role at a venture capital firm as the current COO was transitioning out. I started work in February of 2020, thinking I would have weeks of in-person training before taking over the job solo. Instead, after a few days in the office we decided to work from home until “this whole COVID thing clears up…” and then we never came back. 

When people ask me what my experience was like entering a new industry in 2020 my response is to say that it was interesting. And it’s the truth, because I love my job and all its diverse responsibilities, and I really was learning a lot. But it would also be the truth to say that it was difficult, frustrating, nerve-wracking, and led to plenty of mid-morning breakdowns and glasses (read: bottles) of wine with dinner to de-stress. I felt like it was taking me twice as long, and sometimes even longer, to understand concepts and processes that normally I would have been able to pick up quickly. I’ve always described myself as a quick learner, but when I was trying to learn how to prepare financials and valuations by watching someone screen share on a Zoom call, I felt dumb as rocks. 

Part of this can be attributed to the pandemic itself, but there is evidence behind the statement that online learning isn’t as effective as in person learning. Being in person with teachers and other students creates as social situation with unique interactions and pressures that can help motivate active learning in schools, according to Susanna Loeb, a professor at Brown University who studies education policy. And the gap between success online versus in person becomes even greater for students with weaker academic foundations, so students who struggle in person are even more likely to struggle online. 

The difference between in person and virtual learning, Loeb pinpoints, is that online courses have more distractions and less oversight, which clearly applies to more than K-12 students participating in class online during the pandemic. I certainly felt like it applied to me trying to learn the lingo of venture capital from my living room (I mean, pro rata? EBITDA? Pari passu? Every three words someone spoke I felt like we had accidentally slipped into another language). Building a life online irrefutably changes our perceptions, and is even beginning to change our physical brains.

I don’t want to make excuses or blame the internet for my struggles adapting during the pandemic. Instead, I use this example to highlight that maybe knowledge isn’t as finite as we often believe it to be, that our ability to understand is impacted by our use of the internet, and that our content consumption needs to change in order to accommodate for these shifting paradigms. 

As author and internet theorist David Weinberger says in an interview for the Atlantic, “for the coming generation, knowing looks less like capturing truths in books than engaging in never-settled networks of discussion and argument.” Weinberger describes our current age as one of “networked knowledge” which reflects the way the World Wide Web itself is set up, as an interconnected ecosystem that reflects all of human interest. As a result, the smartest person in the room is no longer a person, but the room itself (meta, right? I mean, not Meta. But, you know, meta). This also means that if the room (meaning the network) is stupid, everyone in that room will be made more stupid, and so they key is “to learn how to build smarter rooms.” 

Building smarter rooms is how we will be able to better communicate complex ideas online. 

How do we do it? Here’s my unsolicited opinion: 

Better knowledge: Update the algorithms 

If you’ve watched The Social Dilemma on Netflix you know that many of the algorithms that dominate our social media feeds (which includes or news feeds as well) operate by sharing similar information to what we’ve consumed in the past in order to keep our attention. There’s been a lot of research presented on the dangers of the internet “echo chamber” so I think it’s fair to start with working against the impulse to cultivate our feeds with viewpoints we already agree with. I also think it’s fair to hold platforms responsible for changing their own algorithms to be less echo-y, but since I doubt that the CEOs of social media companies are reading this blog, I’ll stick with ideas closer to my own realm of control. 

By intentionally searching for and following various perspectives we can make our personal knowledge network smarter. Importantly, I think the right kind of diversity should be considered, meaning it’s not as easy as following both Fox news and MSNBC. It’s more about culling through content to find the right blend of information that’s reliable, easy for you to digest, and on par with what you’re hoping to gain from it. Look for media sources that are both quick bites of information and deep dives. Find writers that are inspiring and uplifting if that’s your vibe, or videos with lots of well-done graphics if you’re a visual learner. 

Better Understanding: Rethink the way we learn

The way we teach learning needs a revamp. Staying mired in memorization, repetition, and contrived testing environments means intentionally holding ourselves back from all that innovation has to offer us. For schools, this might mean moving away from a strict grading and testing system that gives students one chance to complete an assignment and instead moving towards a “mastery method” that allows students multiple attempts until they can show that they’ve mastered concepts. For individuals outside of academics that still want to learn, this might mean learning how to collaborate better online in a variety of formats, including video calls and message boards, without getting dragged into comment wars or “listening” to a lecture in the background while you also do your taxes, clean your kitchen, play Wordle and walk your dog. 

If you’re interested in leveling up your learning, you might start with this video from Jim Kwik about doubling your learning speed. One bit of advice from Kwik that I’ve started using is to ask myself “why must I use this information?” anytime I’m consuming content. This helps me pay attention to the core of what I need from the learning experience, and to avoid useless content that doesn’t actually serve me, because information should serve you. 

Lastly, I’ll caveat all of this by saying that this learning revamp really applies to understanding complicated ideas, but not all learning is complex. Basic math skills, learning a language, or following a recipe are all great examples of learning where the internet can augment and upcycle your educational experience through memorizing, repeating, and testing by trying.  

Better Consumption: Stick to an information diet

Ok, this one isn’t my original opinion, I found it in an article by Angus Hervey on FutureCrunch, and I think it’s awesome. Hervey argues that we need a “slow food movement for the internet.” Basically, that we should cultivate our information habits in the same way we do our nutritional habits, by focusing on maximizing what’s healthy and works best for us and minimizing the what’s not. Hervey lays out his own information diet as an example, which is modeled after the listing books as wholewheat grains, email newsletters as vegetables, podcasts as leafy greens, reddit as beans, specialists publications as fruit, and social media as junk food. 

However you choose to organize your information pyramid, I like Hervey’s advice to begin with mindset, by choosing a “dietary philosophy” for your information the way you would for your eating habits (ex. keto, paleo, vegetarian, etc.). His personal philosophy is this quote from Mr. Rogers: 

“When I was a boy and I would see scary things in the news, my mother would say to me, ‘Look for the helpers. You will always find people who are helping.’” 

Keep Iterating 

Weinberger argues that, try as we might to do anything different, humans are fallible beings that will “basically get everything wrong and then die.” What’s so great is that we keep trying despite that, and as we race to catch up to the progresses in technology and the subsequent changes, we should keep in mind those cheesy motivational posters that remind us that it’s not about the destination, but the journey.But what do you think? Am I on the right track, or way off? What do you have to add to this corner of the internet, my own knowledge network? Let me know and let’s argue. 

I’ve been seeing a therapist through BetterHelp, not because I feel like anything is seriously wrong in my life, but because I feel like things could certainly be better than they are (and because I got a free month thanks to my yoga instructor insurance, so thank you BeYogi).

Growing up I was always creating. I could play pretend for hours, or write stories or plays or make up dances. My best friend in elementary school and I were obsessed with dogs, and we used to spend every weekend making dogs out of clay, giving them names and personalities, and putting on fake dog shows with them that my mom graciously “judged” for us. We even made shoebox dog houses for them to live in. Then at some point, I think I started to see creativity and play as things that kids did. I was ready to be an adult, and what adults did was work hard and set goals and get shit done. So I started to do that too. I think that was the point where I also became anxious, where I let the artist in me fade and the competitor in me flourish. (I’ve written previously about balancing the multiple sides of our personality, and how both of these sides have helped me get to where I am in life). 

I’ve always viewed anxiety as both an undeniable fact of my life and a taboo good luck charm, meaning that I figured I would always be a worrier so there was no point in trying to change it, and that secretly I felt that maybe all my worrying was what made me accomplish so much of what I wanted so far, so I didn’t really want to change it. 

But recently, a few new developments have popped up. First, I got married. And all of a sudden I had this whole list of things to deal with that didn’t just impact me, and that I wasn’t the sole controller of. If I was worried that maybe I wasn’t living in the right city or working at the right job I couldn’t just quit and move and pick up somewhere new and exciting. If I had doubts about my abilities as a wife, a coparent, or a bonus mom to our eight-year-old son, I can’t just convince myself that it’s because I’m no good at those things and decide to go be something else. For the first time in my life I can’t run away, check out from, or exchange my problems. 

So I started talking about my anxieties with my husband Bobby, who has been featured in my blog posts many times before. He’s pretty awesome. And when I told him about my belief that my anxiety was a core part of who I am and how I came to be this way, he asked me to tell him some of the anxious thoughts I have about myself, to pull them from my subconscious and say them out loud. 

As I gave him the list, I started to cry. At first as I said things I thought maybe I was just being dramatic, but as I went on I realized this truly is my internal dialogue, and that it physically hurt to say these things out loud. Things like: 

No matter how hard you work at this you’ll never be good at this. You’ll never even be average.

No one really enjoys spending time with you. They can’t stand you. 

You’re ugly. You’re fat. You shouldn’t be looked at. 

Even writing it now, I want to qualify it with something like “But don’t worry, I’m ok really!” or “Maybe I’m just being a drama queen, it’s not like I think this way all the time.” It fucked me up, having to say out loud the diatribe I’ve been hurling at myself for years now. It fucked me up enough to decide that therapy was probably a really good idea. 

And I’m not sure if it’s acceptable to write publicly about your therapy session for other people to read (Hannah May, best friend and soon-to-be world-renowned therapist, if you’re reading this let me know what the rules are), but I wanted to share that after a few sessions, this shit really does work. It works because talking about it changes the way you start to think about it, whatever “it” is. For me, it’s my anxiety. I’ve started to realize how much I’ve tied my self-worth to my ability to do things, instead of liking me for me. 

So if you’re a people-pleasing lunatic like me and want some advice, here are some of the tips from my therapist that I’ve really been taking to heart: 

1. When I find myself obsessing about negative thoughts, I write them in a journal. Whether it’s reliving a past experience that I wish I could change or stressing over some future event that hasn’t happened yet, writing it out helps me break the cycle of repeating it in my head and helps me feel like I’ve done something about the problem so that I can let it go and move on. 
2. Every week I have a to-do list of 20-50 things that “need” to get done in the week, both personally and professionally. Instead of trying to tackle as many things as possible every single day, now each morning I choose 3 items from the list and just focus on getting those done. Once my “Big 3” to-dos are complete, I can either do more things from the list as a bonus, or I can rest without feeling guilty that nothing is getting accomplished. Now you may be thinking (like I did), 3 things every day for 7 days is only 21 things… what if you have more than 21 things on your to-do list? Then you delegate. Or you delete. And you realize that the world doesn’t end just because your to-do list isn’t empty at the end of the week. 
3. I’ve found things to do just for fun. We all know how important self-care is, but usually what resting looks like for me is sitting on the couch watching a TV show while my mind is racing about all the things I could or should be doing instead, leaving me more exhausted and more anxious. When my therapist asked me what I do for fun, I told her that I like working out, reading books, and spending time with friends and family. She pointed out that all these things are directly tied to my goals or how I identify myself (being fit, being smart/reading things for work, being liked by others). She asked again what I do just for myself, just for fun, and I didn’t have anything to say. To change that, I’ve taken up crocheting, which is great because I have no desire to be known as a knitter or to knit the best blanket in the world, so I can do it just to relax and just when I feel like it. Other things I try to incorporate into my days: taking my dog on long walks without headphones or my Apple watch (because listening to a podcast at 2x speed while trying to get my steps in is NOT fun); coloring in my Jason Momoa coloring book (which is a real thing and is wonderful); making a good cup of tea. 

I have always been hesitant to try therapy because I never felt like anything was “that bad” or that I had any problems I couldn’t handle on my own. And maybe that’s true, but therapy isn’t reserved for bad situations, and it’s not about fixing people. Being married has been the coolest things I’ve ever done and it’s also the thing I discuss most with my therapist. 

If this post has got you curious to explore your options for therapy, here are a few steps you can take: 

1. Explore BetterHelp. They match you with a licensed therapist based on a quick survey and you get unlimited video sessions, phone calls, and messages for $60-$80 a month. 
2. If you have health insurance that will cover some or all of the cost of counseling, try looking on Psychology Today for a therapist in your area that accepts your insurance. Most therapists have an easy online contact option to get in touch, and will schedule a quick phone call with you to see if they would be a good fit for what you’re looking for. 

The beginning of a new year is when we pay renewed attention to our purpose, and we jump into action towards our goals. We feel more hopeful, more focused, and more productive. Remember to put some of that energy towards your mental health as well, whether it’s starting a fun new hobby or talking to someone about what’s worrying you. Here’s to a healthy and happy 2022! 

For years I’ve been looking for a good beginner-level book on investing. I wanted a book that felt approachable, that included frameworks for getting started and taught some of the stock market lingo that I’m not familiar with, a book that wasn’t complete bullshit but also wasn’t impossible for me to comprehend at my current level of understanding. For reference, I started with reading Benjamin Graham’s The Intelligent Investor in 2019. It did not go well.

But I recently finished reading Peter Lynch’s One Up On Wall Street: How to Use What You Already Know to Make Money in the Market, which was that perfect beginner-level book for me (and maybe prepares me for another crack at Graham). Originally published in 1989 the book is definitely dated, and Lynch writes from the perspective of a truly traditional investor, focused solely on maximizing returns without factoring in socially responsible investing principles. Despite that, I enjoyed reading it, and as I read I kept thinking about how many of the principles Lynch outlines for becoming a good investor could also be applied to becoming a good person. 

Here are four pieces of his advice that stuck out to me most, for anyone new to investing or re-thinking their personal development: 

Principle #1: Don’t follow the stock price, follow the company earnings

This is great advice for a new investor, but can also be applied to personal development if you squint at it hard enough. 

In investing, the price of a stock is easy to find and it’s constantly changing, which is why so many people fall into the trap of day trading or panic-selling when they see fluctuations in price. The company’s earnings are a bit harder to find, but are the truest data point you can use to determine whether your investment is a good one or not. If the earnings continue to increase, you should be reassured about your investment, even if the stock price is going down (and if you do a bit more research to see how the company is doing, you can even use that moment as an opportunity to buy more shares while the company is undervalued, which will increase your return overtime. But I’m not here to give investment advice, do your own research). 

If we think of ourselves as companies listed on the stock market, our stock price on a given day may or may not accurately reflect our earning based on any number of factors both in and out of our control. This can lead to some wild shifts in our sense of self-worth and meaning, if we follow it too closely. Instead of basing your value on where you “price” each day, focus instead on your earning potential for the future. Are you still aligned with what you believe in? Are the things you’re doing each day still bringing you joy, helping you find flow, or connecting you more deeply with others? Do you have a sense of purpose and importance? This must be tailored to what’s important to you, but if your earnings continue to increase, you know that you’re headed in the right direction. 

Principle #2: Think like an amateur; don’t overestimate the perceived skill and wisdom of professionals

I hear a lot of people say that they don’t know enough about money or the markets to invest, and as Lynch hammers home in his book, you often know way more about making smart investment decisions than the analysts on Wall Street do, and you can invest without being weighed down by the same regulations and expectations that they have to deal with. 

This is a great reminder outside of investing as well. Being curious, having a beginner mindset, asking questions, staying open minded and doing your own thinking will get you way farther than blindly following the advice of people who position themselves as knowing more about the subject than you do. While this may not apply to all instances (ahem, like in the case of “doing your own research” about a global pandemic), companies that list on the stock market have to provide a ton of information and transparency to consumers and investors, so the information you need is both easy to access and understand.   

Principle #3: Don’t be contrarian just to be different 

Smart investors don’t short the stocks everyone else is buying, they buy the stocks no one else has discovered yet. Being contrarian doesn’t mean avoiding or judging what’s popular. It means contradicting overly patterned and conditioned ways of thinking so that you can discover something new. Buy low sell high is an overly patterned and conditioned way of approaching stocks. Instead, if you have a compelling story as to why you’re making decisions, you can dictate your own portfolio and not be mastered by the market. 

Bringing this back to a real life example, I grew up in the south where people get married and have babies when they are like, eighteen. So for most of my adult life I swore I would never have a wedding or kids. Granted, I’ve only been married a few months, but marriage is DOPE. I love telling people Bobby is my husband, and we are already great parents to his son, so I know one day we will be great parents to our own kids. I think I stuck with the ‘no kids no marriage’ mantra because it made me unique, and it gave me a reason for not being one of those 18-year-old brides, but that’s not a real reason to believe something is it? 

My marriage is something completely unique to me and Bobby, even though millions of other people are also married. We didn’t accept and fall into the typical pattern of what it means to be husband and wife, we built (and are building) a life together that’s catered to us and our needs. I don’t need to undermine people who do it differently, I just need to trust that this is what works best for me. 

Principle #4: You don’t lose anything buy not owning a successful stock 

We are surrounded by the constant pressure to be it all, to do it all, to own it all. But you can have an incredibly successful investment portfolio that misses some of the most successful stocks. Right now I’d be a lot better off financially if I’d bought and held Apple stock when it first appeared on the market (which was in 1980, so 13 years before I was even born), but I’m not any poorer because I didn’t. 

In life, it is ok to let some opportunities pass by, or to realize looking back that a different choice might have been a better one. That doesn’t mean you aren’t creating a successful life for yourself. It just means you aren’t done learning yet.  

Bobby and I live only a few blocks from Gallaudet University in Washington D.C., recently made famous in the Netflix show Deaf U. Several of our neighbors are deaf or hard of hearing, and almost every coffee shop within walking distance hires deaf employees (special shout out to Peregrine, we love you!), so of all the languages to learn we felt this one was the most pertinent for this time in our lives. Also, it’s fun to be able to have a secret method of communication, though after one month of studying I’m still not able to say “Hey I think that guy in the corner is a serial killer” and am pretty limited to saying things like “Hello man do you have a newspaper?” and “I am learning ASL.” 

Learning other languages has always been something Bobby and I have done together. During the pandemic we competed on Duolingo to see who could learn the most Spanish and eventually we hope to learn French, although my French accent is truly the most terrible thing I have ever heard. Being multi-lingual is something I think a lot of people find valuable, but a recent interview on the Tim Ferriss Podcast with Noah Feldman articulated what I think is one of the most important aspects of learning a new language: 

Tim Ferriss: So at 14 you set out to learn Arabic and there are many different flavors of Arabic. But once you were reasonably competent with Arabic, how did that change your universe?

Noah Feldman: It broke it. I mean, it changed my worldview radically and totally. And that’s because when you learn a language, it puts you in the thought world of the people who speak it, and you no longer are seeing them as an outsider, imagining what they might think when they speak to themselves. But you’re actually a participant. You may not be a member of the group, but you can participate because you can speak the language. And since I’d been raised in this milieu that was very Israel focused, very Jewish, there were all kinds of ideas about what Arabic speakers were like, what Arabic was like, what the world of the Arab people was.

And just to see that from the opposite perspective, it blew my mind at a very early age. And I think very few things have had as big an influence on me because I just realized that things just looked different from an alternative perspective. They weren’t necessarily better or worse. They were just really, really fundamentally distinct. And that made me realize that, to put it very bluntly, a lot of what I’d been taught, you could characterize as not having been true from someone else’s perspective.

It’s not that anybody was consciously lying to me. They were just giving me their perspective. And suddenly, I was hearing pretty much 180 degrees, the opposite perspective. And that is the most useful lesson you could possibly give a young teenager trying to make sense of the world. Someone always sees things the opposite way that you see them.

If you want to hear more about the history of ASL, how it relates to Gallaudet University, and how Bobby and I structured our 30 days of learning, check out the podcast on Apple or Spotify, or listen to it online here!  

A mentor of mine recently asked me what the most challenging part of building my career has been so far, and I knew instantly that my answer was the uncertainty of it all. My sister is a surgeon, and I’ve always said that I envy how clear and direct her path has been, that she figured out her purpose in life and had all the steps laid out to pursue it. 

Of course, when I said that to my sister she reminded me that it’s not that simple for anyone, even doctors. She started college as an English major and then switched to Psychology, and it wasn’t until her senior year that she decided she wanted to study medicine. There were extra classes she had to take, a multitude of tests to pass and procedures to go through, potential barriers at every turn where if she failed an exam or wasn’t accepted to the program she wanted, the door to her dreams would be closed. In fact almost everyone I’ve spoken with about their career trajectories, from lawyers to yoga instructors, has reiterated that our futures are never quite as clear as we’d like them to be, and that even the most successful and fulfilled people still aren’t sure what they want to do when they “grow up.” 

Figuring things out as we go requires us to constantly ask ourselves who we want to be and what path we want to take to get there. That’s the question author Ryan Holiday asked himself as he wrote the book Ego is the Enemy. While I’ve read and enjoyed many of Holiday’s books, I always skipped over this one, thinking ego wasn’t really a problem I struggle with. To me, an egotistical person is self-centered, grandiose, and obnoxious, and it’s easy to see when someone is being controlled by their ego. But as Holiday shows in his writing, we all struggle with our egos, and that struggle may not be as obvious as I assumed. 

What I learned from reading Holiday’s book is that ego shows up in me every day, and she can be a real sneaky bitch too, because I’ve only been watchful for her overtly negative qualities. When I feel myself getting boastful, or starting to make excuses or complain, I can quickly recognize it and adjust my attitude. So she switches up her tactics, and masks herself in things I would never recognize as harmful. Now, my ego appears in things I hardly notice, things like: 

• When I spend hours plotting out my “ideal” work schedule, meticulously blocking time off for all kinds of ambitious things: I will wake up by five a.m., I will go on a run and go to the gym, I will write for three hours a day, of course I’ll also work from nine to five and make time to eat, sleep, commute, and maybe even talk with my husband or walk my dog. I organize and then feel incredibly accomplished and proud of myself without having done anything,
• When I tell friends that I’m “working on my novel” even though I’ve barely written a thousand words that week, or when I let myself daydream about all the things I’ll do “one day”, like run a marathon or start my own company, and visualize how amazing it will be: how everyone will love me, and be so impressed with me, and how I’ll be so much happier and better then than I am right now, 
• When I take offense at being asked to do work that I feel is below me, or to participate in a group effort that isn’t connected to what I care about or am interested in, or when I sulk about not receiving credit for my efforts and see everyone around me as competition, striving to prove that I’m better than them even if what they are working on or concerned with has absolutely nothing to do with me,
• When I overperform a task instead of just getting it done and bask in the glory of others admiration or my own pride,
• When I reject compromise and bullishly force my own opinions under the guise of being “passionate” or being “stubborn” because I want it all.

In each of these examples my ego keeps me from achieving my potential without me even realizing it, either because it tricks me into thinking these moments are productive when really they’re just wasted time, or because some of these actions have been reinforced as actually being positive instead of unhelpful. Our society encourages people to micromanage themselves, to create their “brand” and share it with the world constantly, to take your credit where it’s due and that you deserve to have it all. In this way, I can get so wrapped up in the pretend life that exists inside of my color-coded planner and on my social media feed that I’m too busy to look up and realize that I’m not actually doing anything at all. 

Holiday’s solution to ego is simple: work. In the book, he quotes Joseph Conrad who said “I don’t like work—no man does—but I like what is in the work—the chance to find yourself.” There are two types of time in our lives: passive time where we wait and watch and active time where we learn and grow and utilize every second. The more active time we have the more we can find ourselves, and the less our ego can slide into our lives and push us towards laziness or spinning our wheels. 

The solution to ego is to work without need for validation of the work, to be capable of experiencing the uncertainty without letting it drain us.  “What is truly ambitious,” Holiday writes, “is to face life and proceed with quiet confidence in spite of the distractions.” Don’t be attached to the outcome of the work, because that’s what can lead us to a fear of failure so large we don’t even begin. That’s what can lead us to attempt a new PR everyday in the gym so we can post it on Instagram instead of putting our heads down and slogging through those god awful boring reps that actually make us stronger. Let the good work be sufficient. Let it be enough each day to look back and know you’ve met your own standards, not the world’s, that you like that snapshot of yourself, not that someone on the internet does. 

I’ve printed one section of Holiday’s book and posted it at my desk as a daily litmus test for if I’m working in the right direction or letting ego fool me. It says: 

So. Do we sit down, alone, and struggle with our work? Work that may or may not go anywhere, that may be discouraging or painful? Do we love work, making a living to do work and not the other way around? Do we love practice, the way great athletes do? Or do we chase short-term attention and validation—whether that’s indulging in the endless search for ideas or simply the distraction of talk and chatter? 

Fac, si facis. (Do it if you’re going to do it.) 

So. Let’s do it.