Category Archives: Reflections

Do, not be

What do you want to be when you grow up? As you got older, your ideal answer might have changed from ‘fireman’ or ‘teacher’ to ‘partner’ or ‘CEO’. That change itself isn’t so troublesome – you’re growing up after all.

But what happens when you actually make it? Maybe you decided to be president in first grade, and forty years later you did it. Or replace president with your dream du jour. And change forty years to the shorter life cycle of your 21st century job. Where do you go from there?

I think we’ve always asked the wrong question. What you want to “be” phrases your goal in terms of achievements and titles. Maybe that’s a natural outgrowth of our networked life, where those factors are so visible. But in truth, “Imma be” is associating your identity with a destination. You’ll either feel disappointed if you don’t make it, or be unmotivated if you arrive.

Moreover, focusing on what you want to be promotes squandering the present. You’ll rationalize doing work that you feel indifferent about (or even despise) in the name of “putting in your time” and taking a step upward.

About a year ago, I found myself doing just that. Wasting the here-and-now on work I felt little passion for. In fact, my last post on “motivating yourself” was actually a more personal reflection on motivating myself — detailing the exact thought process that prompted me to change jobs. Through that exercise I chose new goals in terms of what could make me happy and motivated today.

This Thanksgiving I’m thankful to celebrate my first year at IA Ventures. Here, with this small family, I feel so lucky to have at once defined and done exactly what I love every day. I know now that I’m at my best when I’m around makers. I thrill at the chance to enable, in whatever small way I can, visionary leaders at the earliest stages of bringing their “favorite futures” to life.

Making what you love a part of your work starts with a simple step: refocus on what you want to do rather than what you want to be. The difference in framing will help clarify if you’re over-optimizing today for some title or wealth or fame destination you hope to reach.

Instead, follow people who inspire you. Work for a purpose you believe in. Build skills that you value because you like practicing them, not because others value them on your resume.

Chances are, what you want to do is actually the best way to become what you want to be. You just can’t see the path until after you’ve traveled it.


Motivating yourself

It’s Monday again. How are you feeling? Whether it’s your first job or your fifth, you may find you’ve lost the spark that once made your work feel great. Recently, I’ve been helping several friends think through their next moves.

I’ve been there before, having left my first job early-on. At the time I built a framework that helped me sort through exactly what I was feeling, and clarified the changes I needed to make. Hopefully you might find it equally useful.

(Much of this model is derived from Dan Pink’s book Drive, which explores the psychology of motivation. When I was changing jobs, I drew his three factors as the axes of a graph, and realized they mapped perfectly to three dimensions you can control for in selecting a new role. If you don’t have time to read the book, his ten-minute talk is a great summary.)

Are you working or being worked?

Let’s start by defining what it means to have a great job. It’s easiest to describe by its effects: a great job motivates you to keep pushing yourself. When you do your work, you anticipate a reward, and your body gives you the gift of increased dopamine transmission. The experience is frequently euphoric. A great job means you begrudgingly leave on Friday and can’t wait to get back on Monday (out of raw excitement and not being a ‘workaholic’).

But what kind of reward are you anticipating? It turns out, many bosses get this deeply wrong. In the employee-as-horse theory, one needs only a carrot and a stick. And the more substantial the carrrot, the harder the employee will work to get it.

Of course, treating employees like horses only works when their function is the intellectual equivalent of tilling a field. So pure compensation isn’t enough to motivate people who need to do creative, unstructured jobs. In fact, offering more money for intellectual work demonstrably has the opposite effect. Extrinsic motivation, like LDL cholesterol, is a necessary element in a harmful form.

Take a look at how you’re being compensated and you may get a clue about why your job satisfaction has dried up. Above a minimum level to pay your bills, mo’ money is not mo’ happy. Is there a carrot being dangled in your face? Does it come up in conversation? Do your managers encourage competition to get the biggest, juiciest carrot?

Then you might just be tilling their fields.

A 3-D approach to your job search

To find a great job for yourself, you need to focus on what maximizes your intrinsic motivation. With it, you’ll find yourself capable of all sorts of magic: working harder and longer, yet being happier even after taking a big pay cut.

In Dan Pink’s conception, if you want to be motivated, you just need to be AMPed. A great job is the right combination of autonomy, mastery, and purpose.

1. Autonomy is a measure of how much you craft your own role. When you’re self-directed, you choose what you work on, who you work with, and when and how you make it happen. You pursue tasks at the intersection of interesting and important. You take ownership over your work, are responsible for outcomes, and can see your impact directly.

It turns out, autonomy directly ties to the size and life stage of a company. As the organization grows larger and gets older, it defines roles, responsibilities, and reporting lines more strongly. People carve out territories for themselves. Equity and ownership over outcomes goes down, less excellent employees come along to ‘fill the role’ and politics form when people are more interested in job preservation than doing great work.

There are always trade-offs: a younger, earlier company has fewer experienced people to learn from, and less direction and feedback on whether you’re doing a good job. But on the whole, the more autonomy motivates you, the smaller a company you should seek out.

2. Mastery means to get better at something, which in a work context defines what you’re getting better at, and how much better you can become. Achieving mastery is motivating because it’s challenging, and as ‘gamification’ suggests, we like pushing ourselves to accomplish difficult feats for fun. But raw difficulty isn’t enough to keep pushing yourself. Like playing any game, you have to believe that the outcome is important, and be surrounded by others who you respect, learn from, and like being around.

This correlates strongly with job function, for example: engineering, product, design, operations, marketing, sales, business development, management, or anything in-between. What you do in the organization will define the tasks that you can draw from, how mentally stimulating and challenging they are, and the outcomes you’ll see. This one requires you to reflect deeply about your career direction, the type of person you want to be, and what you really love to do when money isn’t your motivator.

And perhaps more importantly, your function also determines what kind of people you spend your time with every day. How much do you share common values with your superiors? Since you inevitably become the average of the five people you’re around the most, choose wisely.

3. Purpose is the often-neglected reason for why you’re doing your work. It’s not enough to simply make money, or to enable other people to make more money. Just as the carrot wasn’t enough to motivate you, your company shouldn’t act like a horse either. It needs to have some greater, transcendent meaning in the world, producing good products and providing good service that makes people’s lives happier and better. You have to believe.

Your belief in a purpose is an extremely personal thing. You can’t get that belief from other people’s envy, or others’ definitions of what makes a company great. It has to come from within. So your deep, gut emotional reaction to a company is derived from how much you care about it’s vertical and love its products. Ask yourself if you’d be proud to tell everyone you meet that you work for this company, particularly people who don’t understand what it does.

Think about your past

Now that you know the three dimensions, try placing all your past jobs on the axes. How much did you choose your own work? What did you get better at, and how important was that to you? Why did your company, and by extension, your work matter to the world?

This exercise will be immensely clarifying, and you should repeat it often. Put it on your calendar twice a year.

Try lots of them on

You’ll likely think of the three dimensions and already have a strong opinion about one or two of them from your past experiences. Think of that as helping you take a slice out of the cube of possibilities. Every slice still has infinite variations possible along the third dimension.

Give yourself ample time to explore, and try lots of possible jobs on for size. Read a thousand job descriptions (I’m totally serious), disregarding how qualified you are for the positions. Keep reading until you have ten that you identify with and think you’d love. You’ll know them when you see them.

Then, look at the stage, function, and vertical of each job. I bet you’ll find they share more interesting things in common than the prospect of a carrot.

Note: below is an ad, inserted by, that is not part of this post.

8307 days

Today is Mother’s day 2012, and I always take this time each year to more explicitly celebrate ways my mom has influenced my life. But that usually happens in the confines of a card. This day in this year is also special in that it begins the week that I graduated college last year, and thus also the week that I started this blog.

I was planning to write a one year retrospective on blogging for my official blogiversary in a few days. But I got a little excited and started reviewing my posts early. As I did, I realized how much my Mom has directly impacted the topics I chose to write about, and the thoughts I expressed.

Which is odd, because I haven’t gotten around to showing her this blog yet. But today I’ll change that. So sending her this post will mark the first time she’s actually seen my writing in a while. Henceforth I write to her.

Hi Mom!

It’s been 8,307 days since I was born, and the density of lessons in those days can’t possibly be summarized by one post or the 22 Mother’s Days I’ve celebrated with you so far. But I thought I’d write some of them down for posterity. Here I can also fit more text than I can fit in a card (and you can actually read it, as opposed to my handwriting).

In the past I’ve often written to you on two subjects: things you’ve done that I respect you for, and times you’ve helped me find the right direction. The hard facts of your life — raising me on your own while keeping up with a fast paced career — are eclipsed only by the subjective nuances. You start with being uncommonly at peace with yourself, and layer atop that peace a deep compassion and empathy that makes others feel at ease being around you. You’re at once both strong-willed and gentle, accepting and inquisitive. Simultaneously my ideal role model and my north star.

But none of those concepts are new. What’s more surprising is the subtle way you’ve influenced every decision, action, and thought I’ve had. I’m very much my own person, and you and I passionately disagree with each other on many topics… yet at the deepest level my guiding principles and ideals have all converged on lessons from you.

So here are ten of my favorites. Each underlined link is a blog post, and they can all be traced back to you. Something you’ve said or done in the last 8,307 days that I’ve held onto.

1) Beyrouteys never give up. You repeated this to me a thousand million times when I was a kid, and it stuck. Never giving up implicitly means allowing yourself to fail by trying lots of possible solutions. To “fall forward” as Denzel put it at my commencement last year. When I’m in danger of throwing in the towel, somewhere in the back of my mind you always remind me that Beyrouteys never give up.

This has led me to keep trying at things I previously failed to accomplish. Last year I learned to ride a bike because I had given up on it previously. In doing so, I came to understand the importance of having a safe environment where you wouldn’t be judged or berated for failing, but rather encouraged to push the limits of nature, tools, and yourself a little further. You gave me just that environment. And that’s why I learned to love technology — you can fail over and over and just hit the back button if something goes wrong. Tech culture celebrates failure, and so do I.

2) Disconnect. As much as I love tech, you also helped me realize that it’s a two-edged sword. While it can bring people together, it can also make us even more distant from each other. When you reminisce about your childhood, it reminds me to think twice about how I’m spending my time and what I’m prioritizing. (Amusingly, I once asked you if the whole world was actually in black and white when you grew up).

Even though it seems to you like I’m always on the computer, I take your questions about technology to heart. When a lot my peers let distractions from the internet and social media rule their lives and build up an addiction, I keep my phone on silent and prioritize being in the moment. When I’m thinking of someone, I give them a call and avoid empty online interactions. And even in the hustle and bustle of city life, I often disconnect completely and take a walk. Some of my best memories are when I’ve gone radio silent and unplugged for several days at a time, as when I refinished a table last summer.

3) Take risks. You spent a great deal of your life thinking about risk and protecting against it. At times I know you’d love to insure against everything, but your stories (e.g. missing out on Fender) had a huge impact on my own risk reward curve. You’ve always encouraged taking calculated risks, and adding some random variation to my daily life. For example, you pushed me to “get out there” and meet people when I used to be shy and reserved.

In the past year alone, several of the most life-changing moments happened because I opened myself up to the influence of randomness. When people invited me out to events, I strived to always say yes. I met some of my closest friends that way, found jobs that way, and learned about myself in the process. Sometimes it doesn’t work out, but I keep trying until it does. Today I trust my instincts more than ever before.

4) Defer no time, delays have dangerous ends. I may have learned that Shakespeare quote as a freshman in Mask & Wig, but the point that “anything worth doing is worth doing now” was fundamental to my upbringing. Sure, every parent tells their kids not to procrastinate. But your actions spoke volumes: you dealt with problems immediately instead of letting them pile up. Simple habits, like doing the dishes as soon as you’re done eating, or putting things back after you’re done using them, have stuck with me. Those habits are core to accomplishing long-term goals.

I’m admittedly imperfect at this one, and I’ve realized the perils of fake productivity — when you’re doing the easiest thing rather than the most important. Every time it snowed, you’d head straight down to the bottom of the driveway and chip away at the heaviest, iciest section first. I remind myself of your example when I’ve been wasting time, and attack the most difficult thing on my list first.

5) No makeup. I’ve always loved and respected you for your willingness to show your true skin. Literally, in the sense that you don’t use makeup to tweak your image. But also because you’re never afraid of showing who you are. You don’t cover yourself up to fit what everyone wants of you, and you’re comfortable with acting differently from the rest of the world.

I may only be in my twenties and have a lot to learn, but I am unabashedly myself. All of my friends and coworkers would surely agree that I value things differently than most people, and act on those values. I don’t watch TV because I don’t care about it, and I don’t pretend otherwise. I don’t believe in sending meaningless token gifts. Though many favor brevity over the art of communication, I send long emails when I’m passionate about a topic. And I don’t like coffee, so when people think they need an excuse to meet up, I take walks with my friends instead. ‘Be yourself’ is trite advice, but you’ve lived it in a way that I strive to emulate.

6) Don’t take yourself too seriously. I can go to any group you’ve ever been a part of and find people who love you. They’re not all your ‘peers’. Whether at work or at home, you make people of all walks feel comfortable around you — people more junior to you, younger than you, less intelligent or experienced than you. You’re humble, joke about yourself to light of your actions, and give others credit. You find points of commonality.

This makes you more approachable than anyone else I know, and is an example I follow. It’s easy for people to tell you their secrets and feel connected to you. And, perhaps most importantly, they aren’t afraid to give you feedback and be honest with you immediately after meeting. Since I strive to constantly improve myself, I care deeply about being easy to talk to and open in my conversations. I’ll protect those instincts religiously no matter how ‘high up’ I ever get.

7) Find greatness in everyone and everything. Any place you’ve ever taken me has been an exploration, from the first time I joined you for your commute to work. You asked me tons of questions and let me form my own opinions. (And I now know way too much about airplanes and trucks). You were optimistic, and showed me how to keep searching until I found something worth digging deeper for. You made me try new things constantly, even when I protested, even when they were tomatoes. A tomato was not just a tomato, though. Each of them had slight differences, and we talked at length about the varietals. I may not have agreed with you at the time, but I was listening, and developed an insatiable curiosity for everything.

That curiosity has taken me to the corners of knowledge. Early on, I discovered Wikipedia and was absolutely fascinated by even seemingly dull topics. I learned about the minutiae of everything from law and politics to science and psychology. Behind every piece of knowledge, there’s a story of how it got there. And people have similar stories. Just as curious as I was for information, you taught me to be curious about people. Everyone has something beautiful about their history, decisions, and preferences. So I grew to take conversational risks in hopes of finding every delicious nuance, and have friends from all walks of life and backgrounds because of it.

8) Fun can be meaningful. When I look at the artifacts of your life, I find elegant simplicity. You didn’t buy everything under the sun, and never valued possessions or ostentatiousness. You treated yourself to great experiences, on occasion, and acknowledged that the people you’re with are far more important to your memory of the experience than the things you did. I couldn’t agree more. As people spend time on the things that don’t matter, and create artificial dramatics in their lives, I know that the simplest things are usually the best.

9) Be other-oriented. Perhaps the most amazing thing about you is that, in spite of all you do, you put other people above you at every turn. Small lessons from your actions have made waves in the rest of my life. When we went out to somewhere new, you took the time to learn and call people by name to help them see how important they are to you. You were great to everyone around you, even people you don’t know, and step up to help them when you see something wrong.

You’re great to everyone, and though I’m not sure how you do it, I strive to emulate your example. WWMD is the first thought in my mind when an opportunity to help someone presents itself. And as I experience life, I keep other people at the top of my mind so I can show, tell, and send them things that will make them happy. I know that in comparison to you, I’ll always come up short on this dimension, but you make me want to be a better person every time I think of you.

10) Focus. It’s common knowledge that I have a pretty terrible memory. I blame that on genetics to some extent — we’re both pretty forgetful. Yet you always remember the things that count, and forget the rest. I’ve taken the same approach to my life. Last year, I started this blog with a post called “The backpack, the binder, and the basket.” I wrote it as I organized my papers from school and took stock of what memories I’d actually take away from my classes. The ones I’d choose to carry with me every day, in my metaphorical backpack, were very few.

So as I take stock of the last 8,307 days, and the memories and lessons that I’ve learned, one thing sticks out. The ones worth carrying in my backpack all came from you. I love you mom.


Long emails

I have a confession to make: I write long emails. I don’t write them frequently, but when the topic is right, I’ve been known to expound in paragraphs at a time. I compose in stream of consciousness, and go back to edit, restructure, and make cuts. But no matter how much I rewrite and excise the junk, I still end up with hundreds of words.

This is seen as a nuisance by many, and discourse on email best practices often makes me feel guilty for pressing send. Yet in our new tl;dr normal — mobile connectivity, short-form communication, and constant distractions — there’s something deeply refreshing about a long email dialogue. So I will no longer be apologetic about my habit.

How could long email ever be refreshing? Let me count the ways:

The Ladder of Inference

  1. Completeness. You present the whole picture of relevant detail all at once. This encourages consideration of a topic holistically, and systemic thinking before analysis.
  2. Data. You travel down the “ladder of inference” and present not only your conclusions, but the underlying data and assumptions that guided you. Opening up your data allows for reinterpretation, and we can identify differences in perspective on the same observations.
  3. Logic. Writing long-form thoughts activates your reasoning, which helps you to organize complex information, eliminate senseless connections, and achieve greater understanding in the process.
  4. Quality. Taking your time forces you to think deeply, and encourages solitude. Receiving a long email changes expectations around synchronicity, and allows the recipient to sleep on it.
  5. Revision. Stepping away and rereading your email yields edits, reconsideration, and simplification. It also encourages perspective-taking, which in turn helps you better understand your recipient’s point of view.

Even beyond these useful properties, long email reveals something beautiful: your passion. When you have the instinct to write an essay-length message, it’s a direct indication of how deeply you care about the topic. For example, I’ve recently uncovered my intense excitement about disruptive fintech startups by sending long-form thoughts to several founders. I wouldn’t have realized how much I love this area if I had cut my ideas short.

In the process of speeding up our communication, we’ve somehow managed to discourage our passionate thoughtfulness. Brevity and rapid, informal tone is now interpreted as a signal of confidence, rather than of superficiality. Attention span is limited to thirty seconds or less.

Of course, for the majority of email, these heuristics make sense. We focus on getting things done, and use the email inbox as a task list. But this task-orientation makes email glib. For example, the Times recently suggested: “Make one point per e-mail. If you have more than one point, send separate e-mails.” And there’s a whole email charter that asks us to avoid open-ended questions and send only short, actionable messages.

So I propose a more nuanced view: that there is a place for long email in our communication toolbox. Sure, it’s not the hammer or the screwdriver, and shouldn’t be used as frequently. It’s more like that hex key you’ve been saving from your last Ikea trip. Not useful in most situations, but when the right opportunity arises, you’ll be happy you kept it around.