Archive | life RSS feed for this section

The Fat Doctor Problem

2 Mar

A few weeks ago, I took an Uber from my apartment to a friend’s place in the Mission. On the way I was making small-talk with my driver. We started talking about his recent divorce and how it’s impacting his finances and his mental health. I felt bad for the guy.

He started giving me advice. It was pretty much what you’d expect – women can’t be trusted, never get married, not worth the risk, etc. It nicely illustrated something I’ve learned over the last few years:
Pay attention to the person behind any advice.

If you’re doing anything at all, you’ll likely be inundated with advice. Well-meaning friends, family members, co-workers and mentors will al chime in with their thoughts about things you should do. A lot of this advice will come from people smarter, richer, and more successful than you. How do you weed out the good advice from the bad?

My best heuristic for taking advice is simple: look at who it’s coming from. If that person is someone you’d like to emulate – if you want to be in their shoes when you reach their age – listen to their counsel. If not, ignore it.

This can be a bit more nuanced, but the general principle is useful. My taxi driver for example: I’ll listen to his input on anything he tells me about getting around the city, cool neighborhoods or restaurants worth checking out. He knows that stuff, and I’d love to have the same knowledge of San Francisco that he does.

His track record with women though? Not even close. I don’t want to be a 40 year old, twice-divorced father of two. Forget that. Why listen to someone who’s mental model of the world has gotten them to a place you don’t want to be?

Yes, this means you miss out on some good advice. You ignore the thoughts of some very smart people, especially those your age. It doesn’t matter. There are enough smart, successful people out there living the life you want to live. Find them, and take their advice to heart.

I call this the “fat doctor” heuristic. If my doctor is fat, I’ll ignore anything he or she has to say about eating habits. I’ll take that advice from someone who’s healthy, thank you.

Apply this rule of thumb everywhere. You’ll soon find yourself seeking better advice, and ignoring bad advice you previously considered.

Why Feeling Like a Failure is a Good Thing

21 Jan

Have you ever tried doing something you aren’t good at? Worse, have you ever really really wanted to be good at something, and yet when you tried you just couldn’t get it? Say you wanted to learn a dance, or tried to hit that high note from “I Believe in a Thing Called Love.” And yet, you just… couldn’t. Then comes the confusion, the weight of failure.

This is how I feel every week.

I think this is a good thing. If you want to learn rapidly, you have to get comfortable with failing. You need to get used to feelings of confusion, anxiety, even a little fear. This feeling of unease is natural when you’re doing something you haven’t yet mastered.

This is an opportunity. Whenever you feel inadequate, you can reframe this feeling and understand that it’s a necessary condition of learning something. It’s part of rapid learning and improvement, and is a positive sign of growth. If you feel like things are coming easily, you’re probably not stretching yourself enough.

What does all of this mean? That feeling incompetent is a necessary condition of learning quickly. 

Ira Glass, host and producer of This American Life, alludes to this in one of my all-time favorite quotes:

Nobody tells this to people who are beginners, I wish someone told me. All of us who do creative work, we get into it because we have good taste. But there is this gap. For the first couple years you make stuff, it’s just not that good. It’s trying to be good, it has potential, but it’s not. But your taste, the thing that got you into the game, is still killer. And your taste is why your work disappoints you. A lot of people never get past this phase, they quit.

Most people I know who do interesting, creative work went through years of this. We know our work doesn’t have this special thing that we want it to have. We all go through this. And if you are just starting out or you are still in this phase, you gotta know its normal and the most important thing you can do is do a lot of work. Put yourself on a deadline so that every week you will finish one story. It is only by going through a volume of work that you will close that gap, and your work will be as good as your ambitions. And I took longer to figure out how to do this than anyone I’ve ever met. It’s gonna take awhile. It’s normal to take awhile. You’ve just gotta fight your way through.

Keep fighting. Don’t quit. Learn faster than you could have ever imagined.


Munger, Money and Achieving Your Goals

11 Jan

From this transcription of a talk by Charlie Munger:

And the one thing that all those winning betters in the whole history of people who’ve beaten the pari-mutuel system have is quite simple. They bet very seldom.

It’s not given to human beings to have such talent that they can just know everything about everything all the time. But it is given to human beings who work hard at it—who look and sift the world for a mispriced bet—that they can occasionally find one.

And the wise ones bet heavily when the world offers them that opportunity. They bet big when they have the odds. And the rest of the time, they don’t. It’s just that simple.

That is a very simple concept. And to me it’s obviously right—based on experience not only from the pari-mutuel system, but everywhere else.

And yet, in investment management, practically nobody operates that way. We operate that way—I’m talking about Buffett and Munger. And we’re not alone in the world. But a huge majority of people have some other crazy construct in their heads. And instead of waiting for a near cinch and loading up, they apparently ascribe to the theory that if they work a little harder or hire more business school students, they’ll come to know everything about everything all the time.

To me, that’s totally insane. The way to win is to work, work, work, work and hope to have a few insights.

How many insights do you need? Well, I’d argue: that you don’t need many in a lifetime. If you look at Berkshire Hathaway and all of its accumulated billions, the top ten insights account for most of it. And that’s with a very brilliant man—Warren’s a lot more able than I am and very disciplined—devoting his lifetime to it. I don’t mean to say that he’s only had ten insights. I’m just saying, that most of the money came from ten insights.

So you can get very remarkable investment results if you think more like a winning pari-mutuel player. Just think of it as a heavy odds against game full of craziness with an occasional mispriced something or other. And you’re probably not going to be smart enough to find thousands in a lifetime. And when you get a few, you really load up. It’s just that simple.

When Warren lectures at business schools, he says, “I could improve your ultimate financial welfare by giving you a ticket with only 20 slots in it so that you had 20 punches—representing all the investments that you got to make in a lifetime. And once you’d punched through the card, you couldn’t make any more investments at all.”

He says, “Under those rules, you’d really think carefully about what you did and you’d be forced to load up on what you’d really thought about. So you’d do so much better.”

I’ve been thinking about this a lot lately. If you take a look at my 2013 goals, I essentially did the exact opposite. I planned on doing multiple, unrelated things in areas where I didn’t have any sort of insight or advantage (starting a charity, a TV show, start another company, 5x traffic and subscribers to this blog). That was stupid.

I’m changing my goals drastically this year. I have 1 major goal I’m focusing on, and 3 habits I want to build in the areas of health, fitness and sociability. Charlie Munger’s words of wisdom were one of the main reasons I decided to take this approach in 2014. We’ll see how it pans out.

What are some of your goals for 2014? Do they cluster around 1-2 themes or areas in which you’re excited to focus? Or are they a bit all over the place (like mine were last year)? Would love to hear your thoughts via email or in the comments.

2013 Goals – How Did I Do?

25 Dec

Sometime in February of 2013, I decided (inspired by my buddy Scott Britton) to write down and publish my goals for 2013. Though it was a great year in a lot of ways, I didn’t accomplish much of what I thought I wanted at the start of 2013 (original list of 2013 goals here).

Goals Completed:

  • Paid off my student loans (yay!)
  • Charged $100/hr for consulting work. Ended up doing more than 20 hours of it (20 was the goal) and made this a solid income stream in 2013.
  • Took improv classes. They were a lot of fun, though didn’t have the social impact I thought they might. However, totally worth it – it’s like adult playtime. And a few of the people in my group were hysterical.
  • Read 75 books on the year. Currently sitting at 72, but within finishing distance of 3 books right now. Will definitely complete this by December 31.
  • Wrote a blog post that got 10,000 views. That would be this one – Why Real Businesses Don’t Charge $5 a month.
  • Completely eliminate sugar from my diet. I did a great job with that, only eating sugar at Thanksgiving. Otherwise, I never ate or drank sugar.
  • Started and ran 1-2 social groups in SF. I started a growth group for people running growth at different startups in SF, and have a good friend that I’ve been co-hosting dinners with. Will continue with both in 2014.
  • Go to a music festival. This was actually one of the highlights of 2013, as I went to a bunch of awesome shows – Tiesto, Muse, Kendrick Lamar, Kaskade, Avicii, Zedd, Skream, Blink182, Porter Robinson, Goldroom and a few others. I realized that I really enjoy seeing live music, and will do more of this in 2014.
  • Got a mentor in the publishing/writing space. Made a lot of progress in this area in 2013, and feel pretty well positioned to launch Traction Book (finally) in 2014.

Came Close:

  • Go camping with friends. Instead of camping, I ended up doing a bunch of awesome weekend and road trips, but no camping.
  • See Louis C.K. live. He never toured any of the cities I was living in, but I did see a bunch of other comedians live – Daniel Tosh and Jim Gaffigan to name a few. I’ll see him next time he’s on tour.
  • Create an event at least 20 people attend. I’ve co-hosted an intimate, invite-only event for 15 people. I also realized this year I function better in smaller settings, so won’t have this goal next year.

Complete Failures:

  • Sell 10k copies of Traction Book. This was just naive from the start. I had no idea how long it takes to write a book – f’ing forever. If I write a book again, I’ll definitely have a different way of approaching it (which I’ll write about in the future).
  • Travel outside the country. Another year gone by and I still haven’t done this. I am planning a trip in February that should allow me to cross this off.
  • Go electronics-free once per quarter. I didn’t do this, and it’s really kind of stupid that I wasn’t able to get it done. Will be doing this in January 2014.
  • Be able to bench 1.5 body weight, squat 2x body weight, and deadlift 2x body weight. I worked out very sporadically during 2013 and didn’t stick with the Stronglifts program I started the year with. Not sure that I’ll ever make lifting a priority – I’ve started doing some other workout routines that I enjoy more.
  • Spend $500 materially improving someone’s life. Still time to do this, but it was one of those things I never made a priority.
  • Meet David Sacks. This was never a priority, and kind of a stupid one. I’ll meet him when I have something more to offer.
  • Give one talk to at least 200 people. Didn’t follow up on opportunities where this could have happened. Applied to speak at the Lean Startup Conference, but wasn’t accepted.
  • Try Brazilian Jiu-jitsu for a month. This one was easy to do and I blew it. Signed up for classes in January.
  • Volunteer 1x/month at least. Another relatively easy one, though I have signed up as a mentor in a program starting March 2014.

Goals I Put on the Backburner:

  • Reach 1000 blog subscribers. With the year I had, my priorities shifted away from blogging and more towards finishing the book, networking and working on Airbrake for much of the year. From what I’ve seen, bloggers with large audiences do a few things: blog a lot, or do worthwhile things outside of blogging that helps them build an audience. I definitely want to fall in the second camp, as writing a blog post takes me a long time. I’m confident I’ll accomplish this at some point, but it just wasn’t a focus in 2013.
  • Write 3 guest posts for reputable blogs. This is in the same vein as above, blogging just wasn’t a focus in 2013.
  • Create a TV show. One of my major realizations in 2013 was that my time is limited, and I want to focus my limited time and energy on really crushing 1-2 things. I still want to make a TV show, but not until I get a few other things off my plate.
  • Start a charitable organization as a side project. Same as above – I worked on focusing on a few things in 2013 and really trying to nail them.
  • Start a company or organization focused on improving education in some small way. Same as above.
  • Create an interview series on mental models. Again, same as above.

Cool Things that Happened:

Though it may seem like a failure of a year given how many goals I failed, it was a really excellent year in so many ways. It’s been by far the most productive, financially rewarding and educational year of my life. Some awesome stuff that happened:

  • I moved 3 times, from Pittsburgh to Vegas to San Francisco (where I live now). Didn’t expect this going into 2013.
  • Met and built close relationships with some incredibly smart and successful people that have vastly accelerated my learning trajectory.
  • Lived in Vegas. It was every bit as crazy as people imagine. One memorable night, I ended up on stage with Tiesto.
  • Grew a lot in terms of being honest and vulnerable in my communications and interactions with people. This has been incredibly freeing and life-changing in a positive way.
  • Ran growth at Airbrake until acquisition by Rackspace.
  • Had the experience of building my own sales team and going through the hiring/firing/managing cycle for the first time.
  • Feel like I’m on solid financial ground for the first time in my life, which is mentally very freeing.
  • Got really into art and learned a lot about painting and art history.
  • Started learning how to make my own music and have been playing around with remixing songs in the chillstep genre.

Major Realizations

This year was incredible. I learned so much about what it actually takes to run and grow a company, became a much better marketer, and went through the hiring/management experience for the first time. Looking back, the theme of the year (unintentionally) was one of learning. I learned what it takes to run and grow a startup, and learned a lot about my own skills and limitations in a professional sense.

On a personal level, I became much more  honest and vulnerable in my conversations and relationships. I also learned a lot about energy and how it works in terms of attracting others to you, and have become a much happier and more engaging person in 2013. I’ll continue to work on this in 2014, along with some other goals I’ll detail in my next post.

Replaceability vs. Impact, or Deciding What To Do With Your Life

17 Dec

For anyone,  choosing what to do with your life is a stressful guessing game. With hard work and some luck comes no shortage of great opportunities. And, with opportunity, many tough choices.

By way of example, let’s take a standard tough decision: what to do after graduating college. Let’s say you have two job offers, Job A and Job B. Job A is for a position at a large firm where you’ll be doing work that doesn’t interest you, but will pay 30% more than Job B. The second job is at a smaller company where you’ll be paid less, but it will expose you to greater learning opportunities and responsibility. What do you choose?

This answer will depend on the mental models you use to weigh different factors. Whether you realize it or not, your mental models determine how you think about the world. One set of people will be optimizing for money over just about anything else – maybe they want to save up for a special purchase, or have a lot of debt to pay off. Others will focus on learning and hope that it pays off in the future.

These types of “which job” questions are relatively straightforward. The really tough questions come when choosing your work. You only have one life, and where you choose to focus your energy will determine a lot about your future – your happiness, well-being and long-term impact on the world.

The most useful framework I’ve found for making such decisions was introduced to me 2 years ago by the brilliant Nick Pinkston. Essentially, if you’re aiming for impact as opposed to personal happiness, your approach will be far different than someone who’s optimizing for personal freedom.

Nick’s framework is essentially this. If you care about moving humanity forward, focus on areas where you can have a large impact and be irreplaceable. Take a look at the matrix below for an idea of how this breaks out:

impact vs replaceability impact vs replaceability

Let’s take doctors as an example. Doctors clearly have a large impact in that they help people achieve a much higher quality of life than they would otherwise. They help the sick recover and generally keep people healthy. They do a lot of good.

However, as an individual focusing on making an impact, becoming a doctor probably isn’t the best path. Though relatively high on the impact scale, doctors are also highly replaceable. There are hundreds of thousands of them in the US, and 25,000 new doctors enter the market every year. If you choose not to become a doctor, someone will easily fill your stethoscope.

A similar dynamic exists among teachers. Hundreds of thousands of new teachers flood the market each year, leading to a glut of teachers. Though replaceable, they clearly have a tremendous impact on their students. Thus their position in the bottom right of the above matrix.

Contrast this with someone like a cancer researcher or entrepreneur like Elon Musk. Each of these people, if they succeed, will have an enormous impact on humanity. Additionally, few people are cut out for highly technical research or starting futuristic companies – each of these individuals is extremely difficult to replace. Without Elon Musk, we don’t have Tesla, SpaceX and the Hyperloop. We have a void.

On the other side are those who are difficult to replace (athletes, actors and the like) but who have a relatively low impact on humanity. Though famous and hard to replace, the existence of someone like Cameron Diaz doesn’t add to human progress. Then, you have those who’s work is both low-impact and easily replaceable. No matter what your values, you probably don’t want to be in this quadrant.

Now, I want to be clear – doing things that are not high impact and hard to replace is not wrong. Those who work in low-impact and highly replaceable jobs are not doing anything wrong – every option in the matrix is totally valid for individuals with different goals. This is just a framework I’ve found useful in giving me clarity around some major life decisions.

Choosing a career path based on the above framework can lead to a lot of misunderstandings. In college, I dated a girl who’s mental models and values were traditional – “do well in school and then get the best job you can.” Mine was a little different: I was optimizing more for learning and being around smart people as much as possible. This led to quite a few arguments: I saw skipping some class to take a meeting with someone as the correct decision. I was getting to know smart people and learning faster! She saw the opposite: to her, I was hurting my chances of getting a good job after college and jeopardizing a good career in finance (my college major).

Thinking through your mental models can be extremely useful as you think about careers and what you want to do with your life. In the end, it’s a highly personal thing – deciding what you care about and how best to get there is a process that only you can begin.

This reflection also allows you to contextualize the many things you’ll read about life choices. It changes how you react to someone espousing how they’ve quit their job to travel the world. Instead of feeling like you’re missing out, you can pause, reflect and realize that they’re operating under a different set of values. They’re optimizing for something else (variety of experiences?) than you are, and consequently have a very different path to achieve their goals.

My Experience in a Sensory Deprivation Tank

4 Jun

Over Memorial Day weekend I crossed off a bucket list item and spent an hour in a sensory deprivation tank. Minus the saltwater (still) stuck in my ears, it was a really cool experience.

Way nicer version of the isolation tank I used

It’s a weird experience, and definitely different than anything I’ve ever done. You’re weightless (or as near to it as I’ve ever felt) and can’t see or hear anything.

The first 10 minutes were tough to get used to. My mind was racing, still caught up in the email/friends/work loop that it too often cycles through. Once I settled in, it was an amazing experience – peaceful, meditative, and just a good chance to chill out and think. Afterwards, I felt more relaxed than I have in months, like the post-shower calm you feel after an intense workout.

It was also a little depressing watching my thoughts during this process. I try to stay grounded and think about impact (as opposed to money), but find it challenging. Regardless of intent, too many of my thoughts revolved around money or success in some way.

My buddy Scott wrote a great post about money last week that I’d encourage you to read. Along with my co-author’s post about money (and how his perception of it changed after becoming a multi-millionaire at 26), I’ve realized the problem with my thinking is that I haven’t defined how I measure success. And with no personal definition of success, our culture kindly defines it for me as money, power, fame.

This is really easy to fall into, and is only really fought against by choosing different scales by which to measure yourself. The stoics suggest always choosing internal rather than external goals. Instead of  ”I will make a million dollars by age 30″, they’d choose a goal you can measure internally. Something like “I will start 2 businesses and spend 40 hours/month on each of them by age 30.” This is measurable, and most importantly allows you to feel accomplished because you put in the effort. It’s a process you have complete control over, and will get you closer to that external  goal. Taking the time to reflect on my principles and how I’m applying them was really helpful in this case.

The rest of my experience in the isolation tank was really cool: deep calm punctuated with small hallucinations. It’s an experience I’d definitely recommend again to anyone, especially if you’re feeling stressed or like you want some time to reflect.


Restaurant Math

5 Mar

Think about the last time you were at a restaurant. Great meal, enjoyable conversation, a few drinks and a fun night out. You’re enjoying the company, the time away from work, the background noise and the conversation.

Then the check comes. Confusion ensues.

Even though we can print organs, fly to space, create self-driving cars and eradicate smallpox, for some reason splitting a check among 3 or more people still remains nearly impossible.

Plenty of times I’ve wondered why this is. Splitting a check should be relatively straightforward – each person takes what they ordered, adds a 20-25% tip and pays that.

The act of splitting a check is so complex because it involves other people. When emotions get involved in otherwise rational decisions, they quickly make a simple situation more complex. They force new decisions on you. Do I want to be a nice guy and pick up the check? Can I get away with having the bill split evenly, even though I ordered the most expensive item on the menu? Can I under-tip and hope nobody notices?

These internal questions add layers of emotional complexity to what is otherwise a basic equation. Your answers to these questions can depend on how you’re feeling at the time, whether or not you recently got paid, how your relationship with your girlfriend is, and so on.

Emotional complexity is everywhere: hiring, firing, working with others… The ability to successfully navigate this complexity can literally make or break your career. Rationally, you hire someone to do a certain job. You set goals, benchmarks and metrics to help judge whether or not someone is meeting expectations and doing a good job. Again, rationally, if they aren’t hitting the goals you’ve established, you should part ways. No hard feelings.

We all know this isn’t how it actually works. I’ve been fired, seen others fired, and recently been the one actually doing the firing. For those that haven’t done it yet: it sucks.

I’ve been laid off once and fired twice. Once because the company was going through some hard times, another time because I took off 18 days in a row (sorry LA Fitness), and another because I underestimated how much work 20 hours a week was when you’re trying to get a company off the ground.

Being fired was not fun, to say the least. As the one being fired, I didn’t think rationally about how I was late on a few projects, or how my last project wasn’t exactly my best work. My immediate thought was that it was personal – they didn’t like me, I had somehow offended the wrong person, I would never be successful in a career, etc. My emotions got involved and made the firing more painful and personal than it should have been. It removed the possibility of treating it as a learning experience, and instead made the event a blow to my self-confidence.

As hard as they can be, such situations can also be an advantage. In the case of getting fired, I was able to get some clarity (once I got over the emotional aspect) about what I wanted to learn and what I wanted to do with my life.

This can apply to other situations, like finding a job. Rationally, a hiring manager *should* go with the most qualified candidate, but will often hire someone they know and like. What this means for the “unqualified” candidate – someone without the perfect resume or the right connections – is that you can get a job by introducing emotion to what would otherwise be a purely rational choice. Take them to coffee, do informational interviews, keep in touch via email, etc. Build a relationship instead of a resume to turn a rational decision into one based largely on emotion.

There’s nothing incredibly insightful here that others far smarter haven’t talked about. I guess my main point is that I’m constantly surprised at how many decisions in the world are driven by emotions and relationships instead of the intelligent, rational adult mind that I thought dictated most things. Envy, greed, fear of missing out, kindness and reciprocity are all very human emotions that have a real impact on how the world works. And I didn’t realize that until I started thinking about how to split a check.

Social Skills as Exercise

4 Feb

I was sitting there at lunch, sweating, staring at the stranger across from me. I had no idea what to say, no interesting topics to bring up. The lone thought racing through my mind, other than wishing this would end, was the disappointment I felt in my inability to make simple conversation for even 10 minutes.

That was the first day of my social workout.

Two years ago, I made a conscious effort to work on improving my social skills. Around the time I started Roommatefit (while still in college), I realized my mediocre interpersonal skills weren’t going to help me succeed. I needed to get a lot of help from others smarter than me, and talking to people via email and Twitter wasn’t going to cut it.

Beginning my junior year, I made it a habit to grab coffee with at least 1 new person each week. The summer I was in San Francisco, I got coffee or lunch with a new person 3x per week, and went to a startup event once a week with the goal to initiate at least 5 conversations. At the beginning it was horrible. I would jump from awkward conversation to awkward conversation, have one good one, and follow it with a painfully strained exchange of sentences that some would characterize as talking. But I practiced, and I improved.

I know since I consciously started working on this I’ve been a lot happier. Today, for example. I went to a lunch with a friend, an acquaintance and a few other people I didn’t know. Two years ago, such a situation would have made me nervous – I would have been unsure of myself, forced conversation and had a horrible time. Now, it’s not a big deal. I had a great time, met some cool people and am grabbing coffee with one of them later this week.

Being a pretty awkward guy has also helped me relate to others who may not have spent as much time practicing their social skills. I understand how others are feeling when meeting someone for the first time, and it’s easier for me to lead conversations to a place where both parties are comfortable. Even a slight improvement in my social skills meant a big leap in my ability to connect with people, which has led to new and better relationships.

Now, although my social fears are (mostly) gone, I’m still working on them. Telling better stories, using more pauses, and adding verbal inflection (I’m a pretty monotone speaker), are all things I need to work on. I’ve learned that your social skills are like a muscle – you can let them wither, or you can work on making them stronger. Improving them followed the same pattern as lifting: you suck, you suck, you see some improvements, you suck more.You don’t have to be that quiet guy forever. After working on this for 2 years I have met more than 300 new people, many who have become friends.

The point of this isn’t that I’m some amazing socialite. I’m not. The point is that I’m better socially than I was, and happier for it. Working on my social skills have had a larger impact on my life than anything else I’ve tried to improve.


Thanks to Nate Speller and Dan Shipper for reading drafts of this. And to all my lunch and coffee partners for their patience over the past two years.

Being Mentally Healthy

16 Jan

For two years now I’ve been drawn to starting companies. From my perspective it looks like there are few better ways you can have an impact on the world. Success (seemingly) requires hard work and smarts, less so connections and political savvy (though they help). Media, politics, large corporations all have billions of dollars of entrenched interests to keep the top dogs where they are. Startups less so.

Though there are good reasons to do do them, I’ve come to appreciate just how difficult the mental side of startups is. The experience of starting a company is the hardest thing I’ve done so far. There’s not much that can compare with the ups and downs, the emotional attachment you have to doing something that hasn’t been done before. And I’m not even tackling a problem like sending rockets into space, or changing payments on the web.

After meeting a lot of people in the space, I think that it is almost more important from a career standpoint than anything else. You can’t do well if you’re constantly focusing on negatives, if you have difficulty finding happiness in your day-to-day, and if you’re not in a good place emotionally. This stuff is hard, and being miserable throughout the process is a sure way to get out of startups altogether. I know too many talented, ambitious people who don’t have the mental makeup to stay involved in the game.

Gabe talks about this a bit with his Startup Career Path post, but I hear a lot of people talking about startups as if they are a one-shot deal. As if their current thing doesn’t work, they leave the game. Even if you don’t get out altogether, being miserable while being in startups is hard. It sucks, and it makes people less effective and productive, to posts like this.

The more people who can be happy and start companies, the better. If humanity is going to advance more quickly, we want more smart people starting companies to solve real problems. This means we need more people who can mentally cope with the ups and downs of striking out on their own. This is valuable even for those that fail, as starting a company leads to drastically accelerated learning.

There’s still a lot for me to figure out, but I’m starting to believe that personal development and growth should be a focus before (and during) the process of starting a company. Getting your head right should be as important as anything else. After all, if you succeed at the cost of being a happy, healthy, real human, I’m not sure that’s a positive. This is why I’m working hard to do things like the Daily Practice. To focus on the good things in life and try to take a long-term view of things.

There are so many things I want to improve: my writing, strategic thinking, productivity, health… things most people struggle with. What I don’t want to deal with is a life of work that makes me miserable and unhappy. And too many times I worry that’s where I’m headed.


Thanks to Nate Speller for reading drafts of this. I’d love to hear what you think of this type of post vs more marketing-related posts. Thoughts?

Working for the Long Term

6 Jan

To start the new year, I’ve been thinking a lot about playing for the long term. About applying strategic thinking to both my life, projects and my blog for the first time ever.

I’ve learned a lot over the past year. One of the biggest lessons I’ve learned (that I touched on in Reification) is just how much stuff is fluff, and is guided by poor, short-term thinking. I’m talking about media’s reaction to startup launches, “new” SEO/marketing tactics that read like the newest flavor of the month, anyone calling themselves an entrepreneur, and the hundreds of people starting a blog working towards passive income.

I finished the book Mastery last week. In the book, Robert Greene examines the lives of some of the greatest individuals in human history: thinkers and doers like Ben Franklin, Charles Darwin and Leonardo DaVinci. One of the biggest takeaways from the book was realizing just how long their accomplishments took, and how much work it took for them to achieve any level of success. For example, Paul Graham was bouncing around, painting and doing consulting until he was 30, and didn’t start YC until he was 41! That means for 10+ after college years he was hacking, painting and developing his creative skills. Then, for 11 more years he was applying that creativity towards his own startup and thinking about them in general. Only after all of this did he have his breakthrough idea about how startups worked and started YC – a full 7 years after he sold Viaweb. 20 years after he graduated college.

20 years. That’s a timeframe I can’t begin to comprehend right now. 10 years ago I didn’t even know what a startup was, much less how one worked. Unfortunately, I think a lot of startup thinking is focused on the short-term. People forgo their health, friendships, relationships and happiness chasing a short-term financial payoff. I’ve felt myself falling into this before. It’s easy to do: every time you see a story about a 26 year-old worth $x million, it’s easy to think “that guy has it all”. This type of thinking seems too common in the Hacker News/TechCrunch driven startup culture of funding, disruption potential and acquisitions. This type of news can even make it seem smart to play for the short-term: raise a big round, hire celebrities, etc.

What Robert talks about in Mastery is different. His big point is that to succeed, you must subsume your ego to strategy. Let your goals dictate your actions, rather than the latest emotion you’re reacting to. This is the difference between copying a competitor’s latest feature, dropping other priorities in the process, and focusing solely on executing your company strategy. This is playing for the long term.

I’ve thought about it in the context of this blog lately. I could probably focus on writing better headlines, blogging more often and covering prominent topics to boost readership. I’ve decided I don’t want to go that route. I figure no matter what happens, if I keep writing 20-30 posts a year for the next 10 years of my life, my audience will grow no matter what I do. I’ll become a better writer and hopefully have things to say that others will respond to.

This approach brings with it a sense of calm. I don’t have to worry about traffic stats, subscribers or tweets. It allows me to let go and focus on the hard work of improvement, less on the shallow results. I can let go of the short-term, the daily worries about success, the ups-and-downs of vanity metrics, and focus on the long-term hard work. At the very least, I can try.