Career Habits: How To Control Your Destiny at Work and Life

Recently, I spoke to three different students from my alma mater. 

They wanted advice on getting started in filmmaking, developing online courses, and marketing, respectively. 

They asked good questions, and most of it centered around a central theme: “what skills should I focus on?” 

Skill development is crucial, no doubt. You must have the chops. However, looking back at my career thus far, in the 3-4 industries where I’ve done well, I focused a lot less on skills and more on habits. 

I like to think this served me well, despite a scattered career trajectory, for a few reasons: 

1. Skill sets change but the ingredients to build skills -- your habits -- remain the same. 
2. Habits are always under your control. Control your habits, control your destiny.

There are habits I honed throughout my career, and I found they: 

• Increase your visibility within the company 
• Help you build allies internally
• Accomplish more (without necessarily being the most skilled) 
• Move you into roles or companies that will challenge you 
• Make you a more valuable asset, therefore increasing your compensation 

I want to start codifying these habits and periodically clarifying my thinking about them. Many were inspired by greater thinkers/doers, and I’ll do my best to give proper attribution. 

Here are the habits that shaped my career (no, none of them are about a morning routine): 

• Habit 1 Consistency over intensity 
• Habit 2: Be likable
• Habit 3: Work for free
• Habit 4: Keep a “help” list 
• Habit 5: Ask for help 
• Habit 6: Change the time horizon 
• Habit 7: Make optimism the reasonable bet 
• Habit 8: Make your own adventure
• Habit 9: Everyone has to go home 
• Habit 10: One kick, 1,000 times
• Habit 11: Read fat
• Habit 12: Read trash 
• Habit 13: Play offense, not defense
• Habit 14: Optimize for stage, not strengths
• Habit 15: Be good with being bad
• Habit 16: Make your resume irrelevant
• Habit 17: Entrepreneurial ≠ entrepreneur (and that’s ok)
• Habit 18: Being great > being passionate
• Habit 19: Working hard > working smart
• Habit 20: Make time to make
• Habit 21: Productivity is an incremental practice
• Habit 22: Great opportunities come from your weak ties
• Habit 23: Attack the work 
• Habit 24: Health first
• Habit 25: Relationships second
• Habit 26: Strong finances, strong career

I’ll dig into each habit below. 

Habit 1: Consistency over intensity 

Inspiration: Firas Zahabi, Head Coach at TriStar Gym

Meaning: When learning new skills, you’re better served working at 70-80% effort and doing it everyday, than going 100% and burning yourself out. 

Take working out. Train at 70%, and you’ll have fun and want to train the next day. However, if you go balls to the wall everytime, you’ll be sore and miserable, and you’ll hate training, so you’ll never build consistency.

Skill development is a volume game. 

Career application: Writing is the bedrock of my career, but I used to struggle stringing two sentences together. So I set a goal for myself: write 500 words a day. They didn’t need to be good words. They just needed to exist. 

For help, I bought a Dana Alphasmart. It couldn’t access the internet and had almost no onboard memory, but it had a full size keyboard, so typing on it was a dream. 

My rule was “no fun” until those words were done. I was a summer camp counselor when I came up with this rule. During break, the other counselors slept, played sports, or hooked up. I wrote 500 words. Some days it took an hour. Other days, it took 5. 

I didn’t write a publishable paragraph that summer. 

Instead, I built a habit I’ve maintained for the last 11 years that has led to my every career opportunity. 

Habit 2: Be likable

Inspiration: Ed Latimore, the Boxer Philosopher  

Meaning: In an interview, Ed Latimore made a passing comment: 

“There is no downside to being likable.” 

This one-off remark stuck with me, and I think he’s right. It doesn’t cost you anything to be likable, and most people want people they like to succeed. 

It’s minimal downside with infinite upside.

Career application: I’ve worked in three industries where I had none of the prerequisites (e.g. skills, experience, network, etc). Being likable is how I got my foot in the door.

(Of course once you’re through the door, you have to perform. Absolves incompetence, charm does not.)

Which begs the question, how do you become likable? 

Likability is rooted in authentic displays of kindness and respect. We consciously and subconsciously express these qualities in hundreds of ways every day. Examples that come to mind:   

• Smile and say “hi” at coffee shops, restaurants, and bars
• Be the first person in a conversation to ask a genuine question
• Call people by their name 
• Find what interests the other person and talk about that 
• Be present 
• Only offer advice in two situations: when someone explicitly asks, and never
• Look them in the eye
• Open and hold doors
• Give authentic compliments
• Accept compliments graciously 

Corollary: It’s a razor’s edge between likable and needy. 

The difference? Likable people anchor these behaviors to an internal compass (what psychologists call an inner locus of control). They behave a certain way because they believe it’s the right way, not because it endears them to others. Needy people require validation from others.

Habit 3: Work for free

Inspiration: Many, but I have to give Charlie Hoehn credit for the inspiration. 

Meaning: Many people get confused about “free work” because they’re fixated on the “free” part. Here’s the detail they’re missing: 

Free work is an acquisition strategy, not a monetization strategy. 

You’re trying to bring in qualified leads for interesting opportunities and mutually beneficial relationships later on… not eke out an existence running someone’s social media campaign for $10/hour.

Career application: I worked for free about 10 times in my career. 

80% of the time, it led to nothing. I invested hundreds of hours and ended up poorer than when I started. 

The other 20% led to discontinuous jumps in my career trajectory and made it all worth it.

Habit 4: Keep a “help” list

Inspiration: Ashley Kruythoff

Meaning: Ashley was the first person I knew who did this. At the time she was an assistant at Fox. 

We were drinking at Smith House in West LA, and she asked:

“What can I do to help you?”

We haven’t spoken much since, but I was surprised and remember the moment vividly. 

I started asking others and keeping a list of what they said. This unlocked my ability to help others at scale, because “how can I help them?” was figuratively running in the background the entire time. 

Career application: Have a short list (3-5) of people you’re trying to help. Review it every day for 5 minutes. Ask yourself, “What can I do right now that will help one of these people?” If you think of something, do it. 

Update your “help” list on a weekly basis.

Think about it: you probably come across 100 different opportunities to help someone else a day. For example:

1. A job opening someone sent you via email, that’s perfect for a friend
2. Two interesting people who really should meet
3. Someone on Twitter is raising money on Kickstarter who could use a push

You help as many people as you can. A small percentage might even help you back. More importantly, you start seeing the world as abundant with opportunities.

Habit 5: Ask for help 

Inspiration: Josh Ontell

Meaning: I used to hate asking for help or advice, but my friend Josh did it all the time. He'd say:

"I'm asking a bunch of people for advice. I really respect your opinion, what do you think about this situation...?"

What I noticed: I liked it. It made me feel good -- whether he took my advice or not was irrelevant. It’s like prom: even if you’re not going, it’s nice to be asked. 

Plus, crowdsourcing advice is the fastest way to get many different angles of looking at the same problem. 

Career application: There are so many things I couldn't have done without asking for help. A few examples: 

• Negotiate salary
• Navigate Hollywood politics 
• Write a bestselling book 

Habit 6: Change the time horizon

Inspiration: Jeff Bezos, CEO of Amazon 

Meaning: Here’s an example of how Mr. Bezos thinks about time: 

“When somebody congratulates Amazon on a good quarter, I say 'thank you.' But what I'm thinking to myself is, those quarterly results were fully baked about 3 years ago. Today I'm working on a quarter that is going to happen in 2020, not next quarter. Next quarter for all practical purposes, is done already and it has probably been done for a couple of years."

Career application: Like many of us, I love the narrative of Young Success: the obsessed individual who accomplishes their destiny by the age of 23 (or earlier). 

For example: Max Landis, Flynn McGarry, or Mark Zuckerberg. 

However, this infatuation prevents us from learning to love the process. Instead, we resent the fact it takes so long, and start to think: “if I can’t have it fast, I don’t want it at all.” 

Change the time horizon, and everything gets easier. 

What does success look like to you when you’re 65, not 35?

Habit 7: Make optimism the reasonable bet 

Inspiration: Morgan Housel, Partner of Collaborative Fund 

Meaning: Here’s what Mr. Housel said: 

“Optimism is a belief that the odds of a good outcome are in your favor over time, even when there will be setbacks along the way.  The simple idea that most people wake up in the morning trying to make things a little better and more productive than wake up looking to cause trouble is the foundation of optimism. It’s not complicated. It’s not guaranteed, either. It’s just the most reasonable bet for most people.”

Career application: In your career strategy, optimism breeds resilience. How I handle every situation trickles down from optimism. 

More than a year ago, my boss and I had a sit-down. He told me, in so many words, that I needed to become a better writer. 

This crushed me. I’d been writing everyday since 2007 (see Habit 1), and for someone you respect to say, “Meh,” that fucking hurts. 

But optimism is the mechanism that allowed me to disconnect from my fragile ego and ask: 

“If I take this to heart, how much better could I be?” 

So I worked at it. Got daily feedback. Participated in workshops. 

Six months later, I was tapped to help write a book with my boss. We delivered ahead of schedule, and the book became a #1 Wall Street Journal best seller. 

Assume the best. If someone says or does something asshole-y, assume it started with good intentions. You won’t always be right, but it’s always the reasonable bet.

Habit 8: Make your own adventure

Inspiration: Eben Pagan of Double Your Dating, Get Altitude

Meaning: Eben had this dating concept he called, “make everything an adventure.” To paraphrase, any mundane experience can become an exciting experience. 

A trip to the grocery store can be fun… if you make it so. A conversation with boring Uncle Kevin at the weekend barbeque can be thrilling… if you pick the right topic. Make it your responsibility, not theirs. You are responsible for making your own adventure.

Career application: When my father opened our first restaurant, it was deadly slow. We opened at 11am, and sometimes no one walked in until dinner time. 

So in the downtime I taught myself to bartend. I learned everything I could about the fish coming in every few days: how to get the bones out of the salmon, what to look for in a piece of tuna. I make sushi. 

When I worked at a Hollywood literary agency, I read scripts during my downtime. When I did enough of that, I studied every literary contract that hit my desk, which helped me get my job with Dennis Lehane. 

If your current role is a total dead-end and you know it, make your own adventure and get out. That’s what Nat Eliason did when he was a consultant: he’d get a full day’s work done in the first couple hours, then read whatever he wanted to for the rest of the day.

Habit 9: Everyone has to go home 

Inspiration: Every restaurant job I’ve ever had  

Meaning: I started waiting tables at 14 years old, at my uncle’s restaurant. Waiters bussed their own tables and ran their food. There was no computer system, so you called your own orders and added up checks with your own pocket calculator. 

If you drew the “bad” station, you were responsible for 10 tables. It got busy. When it comes to their food, people are pretty bougie.

No matter how badly you got slammed though, whether you got seated with three 6-tops in a row or you forgot to fire the mains or you lost a check, at the end of the night, everyone had to go home.

Career application: Some moments are just about how tough you are.

When it’s hard or mundane and there’s no glory waiting for you at the end, it’s just something you need to get through. In those moments, it becomes a game of pushing through the suffering and getting to the end of the night.

No hacks. Just the grind.

It might be a last minute presentation, back-to-back red eyes, or 17 iterations on a sales page, because that’s what it takes.

In those moments, remember that it passes. After a certain point, everyone has to go home. 

Habit 10: One kick, 10,000 times

Inspiration: Bruce Lee

Meaning: Mr. Lee famously said, 

“I fear not the man who has practiced 10,000 kicks once, but I fear the man who had practiced one kick 10,000 times.”

Muscle memory is a powerful force, but there’s no shortcut. You don’t develop the power of 10,000 kicks without kicking 10,000 times. 

Career application: A lot of Hollywood assistants start as a floater -- that means you cover the desk for other assistants who are on holiday or sick. It’s a big deal, your first chance to prove you can do the assistant thing. It means that if a desk opens up, it’s likely that desk will go to you. 

I remember my first. I floated for Racheline Benveniste (Warner Bros, Netflix), who covered Larry Becsey’s desk. 

I didn’t want a bumbled call to ruin my opportunity, so the night before, I practiced answering Larry’s phone dozens of times. 

As in: 

• I picked up the phone
• I said, “Larry Becsey’s office”
• Put the phone back down
• Repeat 

...over and over again, until the words stopped sounding ridiculous to my own ears. 

Then I practiced dialing his cell phone number, like I had never used a telephone before. Then I practiced conferencing and merging calls. 

At the end of my first day, Larry said, “Good job. Have you covered a desk before?”  

“A thousand times,” I said. 

Habit 11: Read fat

Inspiration: Twyla Tharp, author of The Creative Habit: Learn It and Use It for Life

Meaning: Don’t just read the book or the article. Read the related text surrounding it. Read the author’s contemporaries or commentary on their work. 

Knowledge doesn’t exist in a vacuum. To really understand something, you have to learn the context of the world at that time. 

Career application: In Hollywood, I read scripts in addition to my jobs, anywhere from 3-7 scripts a week. After the first year, my reading expanded to the trades (Variety, The Hollywood Reporter, Deadline), every morning. When I didn’t recognize the name of a producer or a prod co, I looked them up on IMDB Pro and TV Tracker. 

My third year, I read all the books. The screenwriting books (Story, Adventures in the Screen Trade, Save the Cat, etc.) the how-to’s on film (The Complete Film Production Handbook, In the Blink of an Eye, etc.) and Hollywood history (The Mailroom, Hello He Lied, Sleepless in Hollywood, Death of the Moguls, etc.) 

After that, I focused on contracts. 

Four years into my Hollywood career, I thought I was finally starting to get a grasp on the machinations of the entertainment industry. That’s how much work it takes.

Habit 12: Read trash 

Inspiration: Ramit Sethi, I Will Teach You to be Rich

Meaning: Ramit told his product developers to subscribe to magazines: US Weekly, People, Cosmo, etc. When we were skeptical, he warned us about treating these magazines as “trash.”

“The people who write those headlines are masters at getting people’s attention and understanding human psychology. They’ve been doing it for years!”

His point: You don’t need to read Cosmo for 7 sex tips to drive him wild! You read Cosmo to understand why others read Cosmo. You read it to understand what it takes for a magazine to remain part of the cultural zeitgeist for 132 years.

Career application: Whether you’re building a business or writing an article, you have to understand what captures someone’s attention. What are their hopes, fears, and dreams? 

Your college literature professor might look down at those trashy magazines lining the grocery store checkout lane, but those writers have mastered the ability to tap into what people really want. 

• People want flat, toned tummies, not a healthy diet. 
• They want a safe car, not dual passenger-side air bags. 
• They want a stable job, not a Bachelor’s degree.  

Reading trash is one of the best ways to look at the world through other people’s eyes. 

Habit 13: Play offense, not defense

Inspiration: Gary Vaynerchuk, CEO Vayner Media 

Meaning: The landscape of business, culture, and technology shifts everyday. Overnight, industries can be killed or born. Millions of dollars, won or lost. 

How we react sits on a spectrum of offense vs. defense. 

Offense is accepting the change, sharing ideas freely, and exploring new opportunities before their strategic advantage becomes clear. 

Defense is resisting change, clinging to the tried and true, and dwelling in the past. 

Whether we know it or not, we ALL operate somewhere in this spectrum. 

Winners play offense. 

Career application: Personally, the more ideas I freely share, the more opportunities come back to me. 

The sooner I’ve embraced change -- whether it’s a new career opportunity, a new app, or even life changes like moving, marriage, and starting a family, the happier I am. 

The other benefit of offense is that it forces you to focus on your strengths. You make others react to you. You’re moving so fast, you no longer have time to worry about what people think about you.

Corollary: Nate Green put it a different way, he said “focus on strengths at work, weaknesses at home.”  

Habit 14: Optimize for stage not strengths. 

Meaning: Too much career advice focuses on “locating your strengths” or “discovering your passion.” The result is mental masturbation disguised as self-reflection. Focusing on your strengths is important… 

But how can you have clarity on your strengths until you’ve tried many things? And your opportunity to try things is correlated to your career stage. 

Therefore, you should make choices that optimize for your career stage: early in your career, experiment with lots of things and make mistakes while you have time to change your trajectory. The deeper you get into your career, the greater the opportunity cost when you stray from your top one or two high leverage activities. 

Habit 15: Be good with being bad. 

Meaning: Most people shy away from their weaknesses. It sucks to realize you’re below average at something, whether or not it’s related to your job (I hate being reminded I don’t have a musical bone in my body and I’ve known that for 20 years). But the faster you’re able to detach your ego from your work, the faster you’ll improve at a particular task, ability, or skill. 

Habit 16: Make your resume irrelevant. 

Meaning: At a certain stage, if you’re pouring hours into “polishing” your resume, you’ve missed the point. You’re not trying to craft the perfect resume. You’re trying to make your resume irrelevant. 

This means you need to become a brand. All that means is that your reputation and body of work should speak for itself. Nike doesn’t need to write “Quality” or “Performance” on their shoeboxes.

No, it does not mean you need to become an influencer or a social media maestro. 

Habit 17: Entrepreneurial ≠ entrepreneur (and that’s ok).

Inspiration: Gary Vaynerchuk 

Meaning: This is more of a mindset than a habit, but it’s important.

Most people are entrepreneurial in many ways: they are proactive and creative and ambitious. 

This is not the same as being an entrepreneur. 

There’s a lot of hype around being an entrepreneur. Being your own boss is an incredibly sexy idea (there’s a Fukienese expression for this that roughly translates to:

“Better to be in front of the chicken than behind the horse.”

In other words, it’s better to own something small than work for the scraps somewhere big).

If you’re a true entrepreneur, the fate of your company is completely in your hands. You are, as Gary Vaynerchuk likes to say, the last line of defense. All the responsibility is on your shoulders. 

Most people are not built to handle these swings, but we’re ignoring this for all sorts of reasons: hype, the surplus of venture capital, lack of friction in the marketplace. 

Be honest with yourself. If those stakes excite you, great. But if you don’t want the responsibility, that’s okay, too. Your happiness is more important than putting CEO on your LinkedIn profile. 

Habit 18: Being great > being passionate. 

Meaning: A deadline looms ahead of you, like a horror movie monster. You need help with this final push. 

Do you ask the person who’s super duper passionate about their job? 

Or do you ask the person who is great at what they do? 

Passion is terrific, and in an ideal world, everyone would be great and passionate. But when it’s crunch time, we want to work with people who are great at what they do. So focus on becoming great. 

Habit 19: Working hard > working smart. 

Meaning: When possible do both. 

But I think we underestimate the value of hard work and overestimate the value of working smart. Hard work (i.e. intensity x time) is always under our direct influence. We control how hard we want to work, all the time.

To be very clear: I don’t think hard work is the only lever, nor the lever you pull all the time. But it’s a lever that’s available 24-7, and most of us don’t pull it enough. 

Career application: At IWT, we had all sorts of processes to “work smart.” We had hundreds of automated systems. But people worked hard, and Ramit (the CEO) set the pace. During your downtime, he’s writing emails, articles, and guest posts. While you’re at the gym or eating dinner, he’s posting a new article on Slack you should read, or replying to every single comment in a blog post, or checking in with you to see if there’s anything you need…

I’m not saying this is the “right” culture. Happiness and productivity experts will give you a hundred reasons why you should focus on just working smart. It’s not for everyone.

You don’t make it very far without a rigorous work ethic. 

Habit 20: Make time to make.  

Meaning: If you are in the business of producing, whether you produce blog posts, podcasts, or pictures on Instagram, then you need to actively schedule time to make that content. 

It will not happen if you don’t carve it into your schedule, and then defend that time like your life depends on it. 

A good way to never make is leaving time to make to serendipity. 

Put in as much effort into the making of time as you do the actual making. 

Habit 21: Productivity is an incremental practice. 

Meaning: There is no one hack. 

You will never implement a Pomodoro technique or perfect Evernote or master your Screen Time and realize you’ve cracked the code on your productivity. 

You figure out your productivity practice one experiment at a time. Michael Alexis put it best this way: 

“I am constantly blown away by how little I know. If you roll back to any ‘six months ago,’ I thought I knew a lot, but in hindsight, I’m surprised I was even functional. I expect this cycle to continue indefinitely into the future.”

(In many ways this is a corollary to Habit 1: Consistency over intensity. Productivity is put on such a pedestal, including this as its own habit felt warranted.) 

Habit 22: Great opportunities come from your weak ties.

Inspiration: Meg Jay via Mark Granovetter 

Meaning: Your next great opportunity won’t come from the people in your immediate circle, e.g. your friends and family. They will come from friends of friends, from acquaintances of family. 

How Meg Jay put it in her Ted Talk: 

“Best friends are great for giving rides to the airport, but twenty-somethings who huddle together with like-minded peers limit who they know, what they know, how they think, how they speak, and where they work. That new piece of capital, that new person to date almost always comes from outside the inner circle. New things come from what are called our weak ties, our friends of friends of friends.”

Fostering and developing your weak ties is a crucial career habit. Chinese people have a specific word for this type of relationship building, guanxi, and it’s a fundamental part of doing business.  

Habit 23: Attack the work. 

Inspiration: Gary Lucchessi, from The Mailroom 

Meaning: When a challenge seems insurmountable, sometimes the only way is straight through it. You have to attack the work. 

Break down the work into small chunks. If you’re still not sure how to approach the problem, break it down further. Show your work and get feedback. If you’re not sure you’re doing it right, do multiple versions.

Habit 24: Health first.

Meaning: When your body and mind are in peak condition, everything else gets easier. There are an infinite number of sub-habits related to health, yet nothing is new under this particular sun: get your nutrition, fitness, and sleep in order. 

Without your health, career success is meaningless. 

Habit 25: Relationships second.

Meaning: Find the alignment between your relationships at home and your career success. This is not easy. It takes an incredible amount of work and constant checking in with your partner, your family, or that circle of 3-5 important people in your life. 

The work is worth it. A successful career is an empty one unless you’ve balanced it with happy and strong relationships. 

Habit 26: Strong finances, strong career. 

Meaning: If your financial house is in order, you have the ability to change the time horizon (Habit 6). Instead of focusing on first-order consequences (e.g. “I need money right now to cover this car payment”) you can play for second- and third-order consequences (e.g. “This job may not pay as much now, but I’m going to learn a lot in the next 2 years.”)

Of course, all else being equal, mo’ money is mo’ helpful, but it’s certainly not a cure-all. 

Conclusion 

The skill sets most valuable for your career will continue to shift. 

Knowing how to operate the tractor was useful until it wasn’t. The same can be said for Excel, or Photoshop, or Ruby. Habits, on the other hand, are timeless. 

Master your habits, master your future. 

A version of this article was first published on my blog.

###

Photo Credit: Alfred Aloushy, Bruno Nascimento, Dylan Nolte, Glenn Carstens-Peters, Fabrizio Magoni, Jason Briscoe, Charisse Kenion