Managing yourself
Chapter 1

Managing yourself

Take radical responsibility for your life and happiness through time management, mental health, and a commitment to grow.

As they say on planes, you should affix your own mask before helping others. The same goes for management. You need to be healthy, present, and emotionally stable before you can support others.

In Chapter 1, we’ll delve into how best to manage your time (your most precious resource), how to create work-life harmony to ensure that you are mentally and physically fit, and how to take radical responsibility for your own life and happiness.

Manage your time & calendar

The first rule in time management is to ruthlessly protect your time. In a world of abundance, your time is the most limited resource. Do not let anyone else create events on your calendar. It should be jealously guarded.

Whenever someone asks for your time, instead of accepting a meeting, ask whether their issue could be resolved with a Slack message, Google Doc, or email instead. If a meeting is inevitable, keep it as short as possible. Ensure that everyone is prepared for the meeting in order to make the most out of the time, and stack your meetings on specific days to ensure long periods of uninterrupted time outside those days where you can get focused work done.

The second rule is to proactively design your calendar.

This chapter was inspired by (and some parts lifted with permission from) some of the lessons in a talk by Keith Rabois.

Calendar audits

The first step to proactive calendar design is to understand where your time is already going. This is why Keith Rabois recommends doing a calendar audit and a regular review of your activities and meetings.

The calendar interfaces we use today actually exacerbate the problem of not optimizing your time. Most executives are entirely reactive to requests for their time and typically let anyone in the organization put meetings wherever they want on the calendar. You should instead view your calendar as something you proactively manage and design. Each Sunday afternoon, write down your top 3 priorities for the week and design your calendar to spend 80%+ of your time on those priorities. You can leave some “leftover” time on your calendar to fill with the reactive requests.

Almost every CEO that we meet with lists recruiting as one of their top 3 priorities. But if we pull up their calendar, most of them have two 45-min coffees and a single 1:1 with their head of talent. If you’re only spending 2 hours on recruiting, is it really in your top 3 priorities?

Managing your time proactively is very counterintuitive and not how most people operate. You need to constantly check back in every week to not let yourself slip into a reactive mode and perform calendar audits on a regular cadence. That means sitting down and going through your calendar for the past month and categorizing each event into your various priorities, as well as identifying how much of your time was spent on high leverage activities.

Lessons from Keith Rabois Essay 3: How to be an Effective Executive by Delian Asparouhov

To learn how to identify your priorities and then categorize your recent activities accordingly, see Getting things done.

Top Goal

A simple way of ensuring that you get your week's top three priorities accomplished is to block off a Top Goal event in your calendar for an hour every day. You can dedicate this to your most important tasks. Turn your phone on silent, turn off all notifications, and don't check email during this time. See Getting things done for more information.

Spend your time on high-leverage activities

In order to maximize your team’s output, you need to spend time on the activities that will influence that output the most. For example, at Square, Keith Rabois would spend at least five hours every week preparing for his presentations at the all-hands meeting on Fridays. That might seem like an inordinate amount of time to spend on a weekly presentation; however, if he was able to communicate a single idea that affected how everyone at the company made decisions, then it was absolutely worth it.

Color coding your time

We recommend using a color coding system when creating calendar events to group activities. For example, use different colors for activities related to recruiting, one-on-ones, recurring sync meetings, customer meetings and time blocks.

This system helps you be more cognizant of where you spend your time, and alter that if needs be. It also helps with energy audits.

Proactively scheduling in recreation

The small joys in life, say lunch with a friend or taking a long walk, tend to get squeezed out of calendars to make way for other people's priorities. It is important to proactively schedule these, otherwise they will never happen.

This is especially critical for exercise. If you are planning to go the gym on Tuesdays and Thursdays, make sure that's in your calendar (and public to your team), otherwise meetings will replace that time. Make sure travel time is scheduled too.

As an introvert, back to back days of meetings are very draining — I avoid them like the plague. Instead, I proactively block off time in my calendar and have meeting-less days to design my calendar to suit my needs. — Alex MacCaw, CEO at Clearbit

Energy audits

If you're starting to feel yourself getting burned out at work, it's time for an energy audit (as well as a vacation!). An energy audit is simply looking through your calendar and reflecting on which meetings give you energy, and which take energy from you. Then try to eliminate the latter category by hiring, delegating, and redistributing work.

It is useful to look at energy and leverage at once. Map out activities with leverage on one axis (low to high) and energy on the other (draining vs energizing). High energy, low leverage activities are traps: you really like them, but they should be delegated. High leverage, low energy activities are chores: if you can't automate them, group them with higher-energy activities.

This is also a great exercise to do with your direct reports during their one-on-ones.

On time & present

Matt Mochary, in The Great CEO Within, writes about being on time and present. We couldn't say it better ourselves, so here is Matt's chapter verbatim.

It is critical to be on time for every appointment that you have made, or to let the others involved in the meeting know that you will be late as soon as you realize it. This is common decency, yes, but it has a greater importance.

There is someone else on the other side of your agreement to start the meeting at a certain time. They have stopped what they are working on to attend the meeting on time. If you do not show up on time, they cannot start the meeting, but they also cannot leave, because they don’t know if you’ll show up the next minute or not.

Each minute that they are away from their work is a minute of productivity that you have stolen from them. This is not only disrespectful but also counterproductive. If they are a customer, investor, or recruit, they will not engage with your company. If they report to you, they will keep quiet but resent you. There is no winning scenario when you waste someone’s time.

But life happens. A previous call or meeting may run late. Traffic doesn’t always cooperate. Even with careful planning, it’s not possible to be on time for every meeting. The good news is that you don’t need to be.

It is only critical to let the other members of the meeting know that you will be late as soon as you realize that you will be. And you must come to this realization (and let the other attendees know) before the meeting starts, through whatever channel will get to them the fastest. Ideally, you’d let them know about the delay before they have to break away from whatever they are doing before the meeting.

In addition to being on time, you must also be present. Being present means that you are composed, prepared, and focused on the subject matter. It can take a few minutes to “get present”—prepare for the meeting, research the topic and the attendees, go to the bathroom between back-to-back meetings, get a drink or a snack, and so on.

Therefore, I recommend that you plan to arrive to an outside meeting fifteen minutes before it is scheduled to begin. For a meeting in your office, wrap up your current project or previous meeting five to ten minutes prior to the scheduled time for the next meeting.

To make this easy, I recommend scheduling 25 and 50 minute meetings only (Google Calendar even has an automated setting for this). This will give you 5 minutes for each half-hour and 10 minutes for each hour to maintain yourself.

When in the meeting, I often see leaders making the mistake of constantly checking their messages. They cannot get away from being “on,” if even for a second. This is not only disrespectful, but it defeats the purpose of the meeting, which is collaboration with the attendees present. It sends a message that the meeting’s content is relatively unimportant. Furthermore, it also breeds a bad habit for the entire company—one that will be hard, if not impossible, to break down the line.

During every meeting, leave your phone in your pocket or face-down. Sticking with the strategies of GTD will help you to focus on your meetings and make the most out of your assembled—and expensive—talent. And if the meeting is not efficient, then make it so.

Getting things done

Getting things done, or GTD, is a simple framework for organizing your life and prioritizing effectively. There are many such systems, but they all share two key insights.

  1. Your mind is made for having ideas, not for holding ideas. It's a crappy office, and your brain did not evolve to remember, remind, prioritize, or manage relationships with more than four things. Any attempt to do so will cause anxiety.
  2. Creative work takes long periods of uninterrupted time. It is disrupted by context switching.

GTD provides space. Invariably, if you capture, clarify, organize, and reflect on all the things that have your attention, it will give you more room. What you do with that room is unique to you. Some people use it to be more creative. Some people use it to be more strategic. Some people use it to be more innovative. Some people simply use it to be present with whatever they’re doing.

But I don't need a system

People who don't use such a system have a false sense of control. They will proclaim that their mind is "all they need" to track their commitments, but ultimately they're driven by a deep fear that if they write down every commitment in their lives, they would not only feel overwhelmed by everything, but also feel grief about the amount of commitments they've broken with themselves or others.

You may well feel these feelings, but I assure you that once your system is set up, a sense of relief will wash over you. Have you ever woken up in the middle of the night with anxiety about all the things you have to do? That's a sign that you need to take these tasks out of your mind by writing them down. Your mind can then rest safe in the knowledge that you have a system. You can only feel good about what you’re doing when you know what you’re not doing.

How GTD works

The principles of GTD are very simple. The actual application of GTD is specific to you and your preferred workflow. That said, we've also included some suggestions on which task managers have worked well for us.

These are the steps.


First, capture 100% of everything that has your attention. Little, big, personal, and professional. Your to-dos, your ideas, your recurring tasks, everything. You want to capture everything so you don't have to think about it again until it's time to do it.

An example of this might be:

  • Organize lunch with Patrick
  • Prepare a talk for all-hands
  • Book sailing-school course


For everything you capture, decide if it is actionable. If not, trash it, incubate it, or file it. If it is actionable, and it will take less than two minutes, do it now. Otherwise, delegate or defer it.


Organize those actionable tasks by category and priority. File them under either Today, a list of your tasks for the current day, Someday, a list of things that you one day want to do but don’t need to get done now (e.g. read a book), or Defer to a particular date.

At this point, you may also decide to break up the tasks into various categories (see the six horizons below). The key thing to remember is not to go overboard; keep things simple. You should be able to understand your priorities for the day in one glance.


Look over your lists frequently to determine what to do next. Do a weekly review to bring yourself current, update your lists, and clear your mind.


Get to work. Choose your next action and get to it. Your system is, at this point, set up to make it easy to figure that out. Your to-dos are organized by priority and placed in categories. Ensure that you have long periods of uninterrupted time for any creative work. Do not get distracted by other tasks, or by incoming tasks (emails, slack msgs, etc.); these can be captured asynchronously.

Using a task manager

We highly recommend using the modern and lightweight Things to record all of this. While the whole company uses Asana to track commitments between people, we find that this is often too heavyweight for commitments with yourself.

Things has the following advantages:

  1. Search. Find all your tasks, attach text files, documents, etc.
  2. Scheduled tasks. Push your task out a few days, or to the weekend.
  3. Syncing to mobile. Access and capture tasks anywhere. reminders

Task managers are so critical that you should feel free to expense any task manager you want to use.

Responding asynchronously

Inefficient people waste a lot of time reaching out about, or responding to, one-off issues in real-time. This wastes everyone's time and introduces a lot of context switching. A much more efficient method is to batch process incoming and outgoing issues.

Throughout the day you will most likely come up with things you want to discuss with your team and others. If someone reports to you, rather than bugging them immediately, consider whether the topic can wait until your next one-on-one. If so, add it to their one-on-one agenda (we use Asana for this). Prompt them to do the same rather than interrupting you throughout the day.

How email fits into GTD

As with any kind of synchronous interaction, email can not only be a huge time sink, but it can also cause you to switch context continuously.

The good news is that you can apply GTD to email fairly simply. The key is to asynchronously batch process your email. Turn off all push notifications and only look at your email twice a day.

Then apply the same principles as above. The capturing step is already done (someone sent you an email), so run through your unread messages and if the response will take less than two minutes, respond right there and then. Otherwise star the message, and potentially use Gmail's delay feature to kick it out to a better time. Then triage your starred messages and get back to an empty inbox.

Email as a stream

The best way I've found to manage email is to treat your inbox as an activity stream, like Twitter, rather than try to read every message. This may not be possible depending on your role (i.e., if it's customer facing), but otherwise I recommend it.

How does this work? Well, you don't need to read every email. Gmail already has a good idea of which emails are relevant to you with its algorithmic importance filter. Here are the steps:

  1. Email will flow in. Gmail will automatically tag some of it as important and float it to the top.
  2. At periodic intervals during the day (do not enable notifications or respond to email synchronously) check the unread emails tagged important.
  3. Star the messages you want to keep around, and let the irrelevant ones flow into the stream of emails below. This will train Gmail's importance filter and improve future results.

These are the settings you will see inside Gmail:

Gmail settings

Top Goal

In companies, there is a never-ending set of burning fires to attend to, and you can often find that weeks go by and you've achieved nothing. This is the result of getting bogged down with the small immediate things and losing track of the important long-term ones.

The Top Goal framework will help you fix this. Greg McKeown, who wrote a phenomenal book on productivity called Essentialism, boils this down to one key concept: Schedule an hour each day (that is, put an Event in your calendar) to work on your Top Goal only.

During this Top Goal time, do not respond to emails, texts, calls, and messages. Only work on your top priority during these two hours. If you follow this pattern each workday, you will achieve amazing things.

You should decide on your top three goals for the week during your one-on-one with your manager. By scheduling time to work on your top goal every day, you can make absolutely sure that it will get done.

I'm still procrastinating...

There is no need to feel shame about procrastinating. Services like Twitter, Facebook, and Reddit were literally designed to be addictive and distract you. They're a tax on human attention.

If you find yourself procrastinating, there are two steps we recommend:

  1. Build awareness. Install RescueTime and track your usage of social media, news sites, etc. Use Screen Time to do the same on iOS.
  2. Run an energy audit. Procrastination is a signal that something isn't quite right. Is it skill? motivation? ambition? Understand which one it is, and address that. It may even be that you like the pressure of a deadline, and you can address that by setting shorter deadlines.
  3. Put up barriers between you and distractions. We recommend Go Fucking Work, a Chrome extension that prevents you from browsing social media and other distractions during set hours.


Every world-class athlete has a coach: every tennis player at Wimbledon, every golfer in the PGA, and every batter in the MLB. An athlete without a coach is incomplete.

The sports world figured out long ago that athletes with coaches win. The business world is just catching up.

Great coaches hold up a mirror so you understand yourself better. They provide feedback and hold you accountable. They're a sounding board to debate ideas with, and a shoulder to lean on in hard times.

Coaching for everyone

At Clearbit, we allow any senior manager to expense coaching. If coaching is so useful, why doesn't everyone at the company have an external coach? Well, unfortunately it comes down to cost. At the current size of our business, it's just not viable.

That said, there is an excellent back-up option, and that is your direct manager. Part of great management is coaching, and one of the reasons we've written this book is to turn our managers into great coaches.

Finding a coach

The best way to find a coach that works for you is the same way you find anyone good: ask your network. Failing that, we keep a list of recommended coaches. And finally, we recommend using Torch, a coaching service.

Advisory board

As the company grows, it is only natural that issues crop up outside of your experience. The worst way to deal with this is to blunder forward, pretending to know what you're talking about. A better approach is to ask for help—and who better to ask for help than a board of advisors.

An advisory board is a set of three to five people who have experience in your domain and have committed to helping you. They are there to answer the odd question over email, pop on the phone with you, and if needed, come by the office. Their networks are also incredibly useful.

An advisory board is a requirement for anyone on Clearbit's leadership team.

When I think of how critical advisory boards can be, one example stands out. Clearbit was going through the process of raising venture debt and had been given some conflicting information around the kind of debt we should raise.

I reached out to Patrick Grady, a member of my advisory board, for help. Patrick is an ex-CEO and has raised hundreds of millions in both equity and venture debt rounds, he's seen it all and has a wealth of experience. Patrick not only came by the office to take us through the whole process, but introduced us to an ex-banker who had been on both sides of the table negotiating venture debt. They aided us with the process, reviewed the debt term sheets, and helped us avoid making any mistakes.

- Alex MacCaw, CEO at Clearbit

A common objection

Advisory boards sound great in principle, but a common objection I hear to them is: "Why would anyone help me? Won't they require compensation?"

Perhaps they will ask for some kind of compensation, but we have found that the vast majority of people are willing to set aside time for you as a way of paying it forward. Every successful person has been helped by other people, and most of them are willing to give back to the community. And a lot of advisors simply enjoy the feeling of creating value. In fact, who doesn't?!

That is one of the very special things about the tech community. Indeed, one day it might just so happen that you too will help some less experienced leader with their own questions.

Setting up your advisory board

Pick three to six people in your network who are either a few years ahead of you in their careers or are semi-retired. Reach out to them, perhaps buy them coffee or dinner, and broach the subject.

We don't recommend opening with any talk about compensation; it changes the tenor of the conversation. It turns out that people feel a lot more satisfaction when they help others out of the kindness of their hearts.

Contacting your advisory board

We recommend making the barriers to contacting your board as low as possible. One such way is by putting your board into a CRM like Streak, so that you can easily reach out and customize the email with a mail merge.

Managing takes an emotional toll. It is important that you have someone to speak to, listen to you, and help feelings flow through you. The alternative is bottling up anger, sadness, or fear until you and your relationships self-destruct.

If you can, build a support group comprised of your peers. Learn to be vulnerable in front of the company and practice Consciousness. Get therapy. Even if you think you don’t need it, you will invariably find it useful.

You are not that voice in your head

Have you ever taken a long shower and had a fictional argument in your head with someone? Or fumed about some situation, letting yourself spiral into a depressed hole? On the surface of it, this is quite silly. You are letting that voice in your head run wild, concocting stories that have little basis in reality.

This voice in your head, the one that tells you that you're not good enough, that you have embarrassed yourself, that someone is out to get you — that voice is just not helpful. Do not dwell on it or let it run your life.

Realize you are not that voice. How could you be? That voice is paranoid, jealous, and irrational; that's not you. The very fact that you can observe it means it's not you.

Learning to quiet that voice, and realizing the stories it comes up with are just that—stories—is a key part of mental health. There are a number of tools you can use to quiet it, like meditation and The Work.

Michael Singer delves into this subject in The Untethered Soul, a book we strongly recommend.


Evidence suggests that meditation is a very good thing for your mind. Meditation helps to quiet that little voice in your head, calm your mind, and improve your focus. Studies show that meditation reduces anxiety, lowers your blood pressure, and improves your outlook on life.

The beauty and simplicity of meditation is that you don't need any equipment. All that's required is a quiet space and a few minutes each day. Start with ten minutes at the same time each day and you will begin to form a habit. Within two weeks, you will experience a noticeable improvement in your mood and stress levels.

There are many forms of meditation, and you should explore them to find one that works for you. We find that, at least initially, a guided meditation app is a great way to get started. We have a team account with Calm. Stick an event in your calendar every day to remind you to meditate, and make it public to the company to lead by example.


There's a common fallacy that therapy is only for unhappy people; this is not the case. A good therapist will hold a mirror up to you and help you understand why you feel what you feel—a critical aspect to emotional maturity.

We are strong believers in therapy, having personally experienced its many positive outcomes. Think of your therapist as a personal trainer for your emotions rather than a doctor for your sickness. Understanding yourself, your emotions, and your mental habits turns you into a better communicator, a better teammate, and ultimately a better human.

At Clearbit, we offer everyone ten free visits annually with a coach or therapist through Modern Health. If you prefer to work with a different therapist, that's fine too—chat with your manager and we'll figure something out.

Therapy for leadership

It's vitally important that anyone with a leadership role is emotionally stable and strong. They are responsible for a lot of people's well-being and growth. That's why we require everyone on our leadership team to have some kind of therapy.

I'm fine, I don't need it

There is a common misconception that therapy is only for ill and/or depressed people. That is just not the case, in our experience. Therapy is a tool for self-discovery, discovering why you feel what you feel, what is behind your behaviors and underlying your actions. Therapists are experts at holding a mirror up to you and prompting you to face your fears.

For the longest time I wanted nothing to do with therapy. I was happy, and felt that therapy was only something you should seek if you were sad. On top of that, when I was growing up, talking about feelings or showing emotion was not something encouraged in the household. But I felt like I had a good handle on who I was, and there was not much more to learn.

Oh what hubris! It was only after a series of events completely changed my outlook on life that I decided that, given how wrong I was before about 'knowing myself,' that there was probably more to learn. I found an incredible therapist who has helped immensely with my emotional maturity. Her insights into why I'm feeling what I'm feeling have been crucial to becoming a good leader.

- Matt Sornson, CMO Clearbit

Sorry, I just don't have enough time

We all have the same number of hours in the day, so a time issue is actually a prioritization issue. Like meditation, therapy is time well spent. You will actually save time if you are less stressed, emotionally stable, and understand yourself deeply.

Physical Health

Building a company takes a physical toll too. All the hard work you put in will be for nothing if the process costs you your health. It is incredibly important that you focus on your physical, emotional, and nutritional health by taking active measures to improve them.

Rather than think in terms of work-life balance, think in terms of work-life harmony. Integrate health into your lifestyle. Go to the gym during the day, if that suits your schedule better, dial in to all-hands if you need to drop your kids off at school, and use our untracked vacation to unwind.

Developing good habits

Developing good habits is the key to health. Getting into habits of regular exercise, meditation, and therapy, to name a few, will give you daily incremental improvements that over time will result in complete transformations.

On the flip side, bad habits will slowly chip away at you. For example, consuming more calories than your body uses won't be noticeable day-to-day, but after a few years you'll look in the mirror and ask yourself: "However did I get so out of shape?"

How are habits formed? It turns out that every habit starts with a psychological pattern called a "habit loop," which is a three-part process. First, there's a cue, or trigger, that tells your brain to go into automatic mode and let a behavior unfold. Then there's the routine, which is the behavior itself. Lastly, there is the reward: something that your brain likes that helps it remember the "habit loop" in the future.

We often forget about the first and last part of habit loops. Make sure you have cues and rewards. For example, the cue to going to a Barry's Bootcamp workout is the event in your calendar, and the reward is the delicious shake at the end. Going consistently on the same days each week helps form a habit better than one-off workouts.

The key to maintaining habits is maintaining a good environment. Make sure you have healthy defaults in your life. This means healthy food options, regularly scheduled exercise, etc.


All the evidence shows that exercising is one of the best things you can do for your physical and mental health. From longevity to happiness, exercise is the key.

You should ideally take some form of movement or exercise every day, but at least ensure that you’re working out multiple days a week. Experiment with what type of movement and exercise works for you, be that weight training, dancing, running, or yoga. Make sure to have a regular cadence by scheduling this ahead of time in your calendar.

If you find your self-motivation is slipping, get a buddy to train with, sign up for group activities (e.g. Barry's Bootcamp), or get a trainer.

Nutritional health

Nutrition is not about dieting or losing weight. Nutrition is about giving your own unique body everything it needs to perform optimally. What you do or don’t eat can affect your mood, ability to focus, quality of sleep, and the amount of energy you have to get through the day. Some people are more sensitive to eating processed foods than others. For some, a vegan diet is what works for them, whereas another person would become very sick without having meat in their diet.

You must develop the ability to notice how foods interact with your unique body chemistry, become aware of which foods make you feel heavy and which foods give you energy. You may begin to notice that you’re drawn to certain foods when you feel a particular emotion or that you seem to be crashing every day at 3 p.m. Most of us have inherited unconscious eating habits from our families and fall into eating patterns based on the pressures around us.

If you suspect that your diet is not serving you, consider working with a nutritionist who is knowledgeable about the way food interacts with the body and can introduce you to better eating habits. You might also choose to consult a naturopath who can offer testing to find out if there are any foods that are causing problems for you.

At Clearbit, we take healthy food so seriously that we have three full-time chefs. Make sure they're aware of any dietary requirements or preferences you have.


Many of us go through life sleep deprived. This has huge knock-on effects on our health and happiness. We make excuses to ourselves and we put off investing in sleep, but imagine how great you would feel if you woke up rested and ready for each and every day. Now imagine that incremental improvement over your entire life — it might change its course dramatically!

Do not stop iterating on your sleep until you have perfected it.

Track it

The first step, as with all things, is awareness. How can you work toward a goal if you don't know what your current status is?

There are some great sleep tracking tools out there, like the Oura ring, Emfit (which goes under your mattress), Gyroscope, and Sleep ++. Everyone in the company has access to our team account on Gyroscope.

Most of these apps will give you a score so you can start to get an idea of what, say, a late night of drinking does to your sleep.

Use a sleeping mask

This is a simple one, but works for almost everyone: use a sleep mask. It'll help filter out light and, once you're used to it, it will give you an almost Pavlovian response once you put it on by indicating to your body that it's time to sleep.

Make sure you get a contoured one that doesn't put pressure on your eyes. We recommend the Alaska Bear mask.

Calming your mind

We live so much in our heads that it can be hard to quiet the chatter of our thoughts and drift off to sleep. Indeed, the harder we try, the worse it gets. If you related to this experience, then we have a simple solution.

The key is to distract your “left brain” and lull it off to sleep. We find that listening to podcasts, or Calm's sleep stories, is a really effective way to do this.

No screens

This is a given, but try and reduce the screen time in your bedroom. Leave your phone and your laptop outside of the room. Ensure that you are using f.lux, or Apple's built-in Night Shift mode, to shift the colors of your display to the warmer end of the color spectrum after dark.

Lower the temperature

Temperature can have a dramatic impact on the quality of our sleep. It's a key part of what regulates the circadian rhythm that determines when your body is ready to go to sleep and when it’s ready to wake up. Your core body temperature needs to drop a few degrees in order to fall asleep, and then stay at a consistent temperature for deep REM sleep.

It doesn't help that we have mostly switched to using foam mattresses, which absorb heat and then radiate that heat during the night, causing us to wake up in a hot sweat.

If you suffer from this, then the solution is a bed cooler. The best one on the market is called a chiliPAD , and although pricey, it will pay itself back in time. If you really want to go all out, we recommend a bed called 8 Sleep, which both self-cools and tracks your sleep quality.

Note: Men especially are often best suited to a colder bedroom.

Facing fear

Fear is caused by a perceived threat to our survival, whether that be a threat to our physical body or an imagined threat to our ego or identity. Fear of physical death prompts you to look both ways as you cross the street. Fear of ego death stops you from asking that attractive guy/girl out because you might get rejected.

While the two threats are logically different things, we can have a difficult time telling the difference between a threat to the body's physical survival and an imagined threat to the ego. Both provoke the same fight-or-flight response.

This is because fear is experienced in an ancient part of our brains called the amygdala (colloquially known as the lizard brain). This part of the brain is responsible for processing all fear, both real and imaginary, and doesn't necessarily "talk" to the thinking areas of the brain that provide rational thought.

To be fair to our brains, historically, threats to our ego were sometimes shortly followed by threats to our survival. Up until a few hundred years ago, an argument with another human could have easily resulted in them killing you. Or perhaps banished from the campfire to the mercy of wolves. There were some very real consequences!

The truth is, though, these days a piece of feedback from your boss is unlikely to result in your immediate demise, and giving a humiliatingly bad speech at a company party won't result in you being hunted down by a pack of wolves.

Our minds, however, are still in this ancient place; we over-index fear.

Is fear useful?

Fear is useful in the sense of "hey, there's this thing over here that probably needs my attention." However, when we start acting on that fear, and making decisions driven by that fear, that's when we start running into problems.

For example, suppose you have an executive, let's call her Anne, who isn't scaling with the company. You know deep down that you will need to replace Anne with someone more experienced. However, you also want to keep Anne in some kind of role at the company, and you're afraid that if you bring the subject up with her, she'll immediately quit, throwing everything into chaos. So what do you do?

A fear-based decision would be to kick the can down the road by telling yourself that Anne could improve. Don't be ruled by your fear; you are not being rational. By delaying the decision, you're doing everyone a disservice. A better approach would be to lean into that fear, be vulnerable, and sit down with Anne. Explain the position you're in, including your fear that she'll quit. You might be surprised—people really appreciate vulnerability.

Fear is a very base-level emotion. It's programmed into us at the machine-code level. When you are in a state of fear, adrenaline starts pumping and your higher brain functions shut down. Fear prepares us to take action, not to think. It prepares us to escape, or even to fight, and in some unfortunate circumstances, to freeze. Notice that there is no mention of complex problem solving, weighing pros and cons, or taking time to process before action. Clearly it's not a great place to be making complex logical decisions from.

Fear as a motivational tool

It's undeniable, though, that fear is a great motivator, or at least in the short term. Throughout history fear has been a weapon in the authoritarian's arsenal to bend people to their will. Even today, fear of "being fired" is the stick most companies use to get things done.

Fear is the path to the dark side. Fear leads to anger. Anger leads to hate. Hate leads to suffering.

- Yoda, Jedi Master

However, these days, using fear to motivate fails for two reasons. The first is that it leaves a toxic waste that builds up over time and leads to distrust, anger, and hate. The second is that the world is increasingly favoring creativity in the workplace, which you simply cannot instill via fear. Fear is an extrinsic motivation; creativity comes intrinsically. Fear doesn't create a learning environment; in fact, it disables learning.

Facing fear

The first step in facing your fears is to acknowledge them. At Clearbit, you'll sometimes hear the phrase "this is a fear-based motivation, but…". Naming your fears and shining light on them is the first step to approaching them.

Step 1: Realize you are feeling fear

Your body will tell you when it's in a state of fear. The key is to build awareness to this.

Let's try an experiment: think back to a situation where you were really scared, perhaps a car accident, or a public speech to a massive crowd. Think about where in your body you felt that fear. Was it a tightening of the chest? Or perhaps a pit in your stomach? This is how your body manifests fear.

Learning to recognize this feeling will give you a chance to pause and dig in before it rules you.

Step 2: Identifying your fears

Named must be your fear before banish it you can.

- Yoda, Jedi Master

Really dig into the underlying motivations behind the fear. For example, does it stem from a fear of a lack of control tracing back to a traumatic childhood experience? Or perhaps your fear of a lack of recognition is ultimately rooted in an indifferent father whose attention you were trying to seek?

For some, even realizing that what they are feeling is fear can be difficult. Here, slow down the process. Notice whether there are times you are seemingly overreacting or have a strong desire to leave a situation. Once fear has been identified as the emotion, ask specific questions about the situation to figure out what the underlying worry is. Ask yourself some questions. What does this mean about me? About others? About the workplace? About the world?

Cognitive therapists use a system called the Downward Arrow Technique to identify the root of negative thoughts and unhealthy beliefs.

Step 3: Leaning in

Once you are more self-aware of your fears and your fear-based motivations, the next step is to lean into them. This is painful, but know that doing otherwise only leads to even more suffering.

Really ask yourself whether the fear is rational. Is it a fact, or is it a story in your head? If it's the former, is there anything I can do about it today? Is it really that bad in the bigger scheme of things? Writing your fears down often helps to rationalize them. Dwelling on your fears in your head only serves to stir them up into a toxic paranoia.

Some techniques

Negative visualization

Stoics used a visualization exercise they referred to as negative visualization to train themselves to stay calm and free from emotional suffering in the face of adversity.

Contemplate what you have, and then visualize your life without those things. Imagine life without your significant other, or without your job, or without your health, and so on and so forth. Don't just think about it logically, really feel it deep down to your core.

Negative visualization is a stoic technique of mentally visualizing that you’ve lost things you value from your life. In my case, it is not having the company and the ability to learn as much as I have at all. I makes me realize that our total progress on Atrium in many ways exceeds where I thought we would be at the outset. If you had told me in the beginning that we would have made this much progress on revenue and team so quickly, I would have been ecstatic. So the smaller, daily bumps are much more palatable.

- Justin Kan, CEO Atrium

First and foremost, this technique makes you quickly appreciate what you have in life: your health, your family, your opportunities, and more. Realizing how blessed you are can put things into perspective.

Second is the ability to set expectations up front and be far more honest with yourself. What could go wrong? How would you handle such scenarios? Can you overcome or plan for them?

This practice is called a pre-mortem in the business world, but the idea is the same. When you prepare for the worst, you are in a better place to deal with disaster if and when it does arise.

Finally, this practice can help you realize that the things that you are afraid of are not as bad as you made them out to be. What if you lost your job? What if you had to move to a much smaller apartment? What if your work turns out to be a failure?

We build up our fears to the point that they are larger than life. Confronting them, and even temporarily experiencing them, can help you overcome such barriers.

This is a great way of putting your life in perspective, realizing how irrational some of your fears are, and also understanding that it wouldn't be that bad if some of them were realized.

Accepting your own mortality

You'll notice that some of the most successful people in this world, like Elon Musk, tend to have a particularly fearless attitude—why is that?

One answer is that it's nature; in the same way that some people have a higher pain tolerance, some people have a higher fear tolerance.

However, it also can be a learned trait, the key part being coming to grips with your own mortality. Now, you might be thinking to yourself, this is a book on management—why dwell on such a morbid topic? Well, that's exactly the point; we just don't like thinking about it. Most of us go through our lives in denial, pretending that we're going to live forever.

The earlier you can come to grips with the realities of your own mortality, the more likely you are to put your life in perspective, care about the things you really should care about, and focus on achieving the things you want to achieve.

Steve Jobs said it best:

Remembering that I'll be dead soon is the most important tool I've ever encountered to help me make the big choices in life.

Almost everything--all external expectations, all pride, all fear of embarrassment or failure--these things just fall away in the face of death, leaving only what is truly important.

Remembering that you are going to die is the best way I know to avoid the trap of thinking you have something to lose. You are already naked. There is no reason not to follow your heart.

No one wants to die. Even people who want to go to heaven don't want to die to get there. And yet, death is the destination we all share. No one has ever escaped it, and that is how it should be, because death is very likely the single best invention of life. It's life's change agent. It clears out the old to make way for the new.

- Steve Jobs

A parting thought

Viagra, valium, and penicillin all have something in common: they were discovered by accident. Fear (in the workplace) is often the fear of making a mistake. Yet mistakes are often where the magic happens.

Realize there is no right or wrong in your choices; perfectionism slows you down. As we accept that we will make mistakes, that they will not ruin us, that we will be ok, we can then take more risks.

Radical responsibility

We all like to think we're emotionally mature, but we also all like to think we're good drivers. It's hubris to suggest there isn't some growth to do.

The crux of emotional maturity is to take full responsibility for one’s circumstances (physically, emotionally, mentally, and spiritually). This is the foundation of true personal and relational transformation.

Now, most people are willing to say, "Sure, I take responsibility for my circumstances. I understand my actions and their consequences." However, taking full responsibility goes far beyond that. It means taking full responsibility for your emotions as well.

The truth is that nobody can make you feel anything. Emotions are generated internally. When someone is yelling at you, all they are doing is vibrating air molecules toward your ears. You choose to feel what you feel, be that anger, sadness, fear, etc. The choice is yours.

That is a hard concept to grasp, and an even harder one to live! In today's world, people are "outraged" at all sorts of things. So the idea that you are outraged because you want to be outraged can be a controversial one. That’s not to belittle the source of the outrage; just know that all the emotions you have associated with any given outrage are your choice.

When you don't take radical responsibility, you rely on blame, shame, and guilt to rationalize your circumstances and feelings and keep the ego intact. Blame, shame, and guilt all come from toxic fear. Radical responsibility means locating the cause and control of our lives in ourselves, not in external events.

Instead of asking “Who’s to blame?” ask, “What can we learn and how can we grow from this? What is my responsibility in this?” We should be open to the possibility that instead of controlling and changing the world, perhaps the world is just right the way it is. This creates huge growth opportunities on a personal and organizational level.

The villain, victim, hero triangle

When we are not taking responsibility and we are blaming others (or ourselves), we fall into what we call the Drama Triangle, where we play the villain, victim, or hero—and sometimes multiple roles at once.


The stance of the villain is “It’s all your fault!” Villains criticize, blame the victim, and set strict limits. They can be controlling, rigid, authoritative, angry, and unpleasant. They keep the victim feeling oppressed through threats and bullying.

In terms of resilience, villains can’t bend, can’t be flexible, can’t be vulnerable, can’t be human; they fear the risk of being a victim themselves. Villains yell and criticize, but they don’t actually solve any problems or help anyone else solve the problems.


The stance of the victim is “Poor me!” Victims see themselves as victimized, oppressed, powerless, helpless, hopeless, dejected, and ashamed, and they come across as “super-sensitive.” They can deny any responsibility for their negative circumstances and deny possession of the power to change those circumstances.

In terms of derailing resilience, victims have real difficulties making decisions, solving problems, finding much pleasure in life, or understanding their self-perpetuating behaviors.


The stance of the hero is “Let me help you!” Heroes work hard to help and take care of other people, and they even need to help other people to feel good about themselves, while neglecting their own needs or not taking responsibility for meeting their own needs.

Heroes are classically codependent and enablers. They need victims to help and often can’t allow the victim to succeed or get better.

In terms of derailing resilience, heroes are frequently harried, overworked, tired, or caught in martyrdom while resentment festers underneath.


The descriptions above are the most extreme versions of these roles, but often they play out as milder versions of these. Often, people stuck in the Drama Triangle will play out a couple of these roles, flipping between them, and have familiar patterns for doing so. Playing in the Drama Triangle for too long can lead you to spiral and even pigeonhole yourself into some global archetype (such as "I am a failure").

The key is realizing when you're stuck in the Drama Triangle: pause, take a deep breath, and try to approach the problem with curiosity.

Side note: Is it ok to hero?

There are often times inside a startup, which by definition has limited resources, that require a hero; for example, when a manager needs to step in to help an individual contributor who's struggling. This is normal—the key thing is to both acknowledge that you're heroing, and understand it's a short-term solution that does not lead to a lot of self-growth.

We are all creators

One of the most profound realizations you can come to in life is the idea that you are a creator. There are two main ways of looking at the world: things happen 'to me', or 'by me'.

To me

If I am in the to me state, I see myself “at the effect of,” meaning that the cause of my condition is outside me. It is happening to me. Whether I see the cause as another person, circumstance, or condition, I believe I’m being acted upon by external forces.

People in to me are “at the effect of” the markets, competitors, team members who “don’t get it,” suppliers, the weather, their own mood, their spouse, their children, their bank account, and their health, to name a few.

They believe that these external realities are responsible for their unhappiness (if only my spouse weren’t mean, I’d be happy); for their failures (if only my sales team would work harder, our top line would go up); and for their insecurities (if I had more validation from my boss, I would feel more secure at my job).

People in a to me mindset do not take responsibility for themselves, and instead blame others, or external factors. This is because it's far less effort to play the victim than to take responsibility.

People consistently stuck in a to me mindset are often playing into a wider archetype they have about themselves, such as 'I failed because I'm a failure'. Ultimately, beneath this lies an urge to elicit sympathy from others, and again requires less effort than taking responsibility.

By me

When people shift from below the line to above it, they move from the to me to the by me state—from living in victim consciousness to living in creator consciousness and from being “at the effect of” to “consciously creating with.” Instead of believing that the cause of their experience is outside themselves, they believe that they are the cause of their experience.

People in a by me state choose to see that everything in the world is unfolding perfectly for their learning and development. Nothing has to be different. They see that what is happening is for them.

Instead of asking “Why is this happening to me?” the by me leader asks questions like, “What can I learn from this?” “How is this situation ‘for me’?” “How am I creating this and keeping this going?”


To shift out of a to me mindset, we first need to realize we’re in one—and take a deep breath. Then we choose to to take radical responsibility for whatever is happening in our lives, to let go of blaming anyone, and to approach problems with curiosity.

Long-term shifting

The most successful people in life manage to approach most of their problems with a by me mindset. They realize they are creative forces in their lives, and they can have a massive impact on how their lives play out.

The only way we've seen to fundamentally shift to a long-term creator mindset is via goal setting. Set small goals, achieve them, and then set larger ones. Prove to yourself that you can achieve things you set your mind to. This builds up the personal confidence needed to feel comfortable in the by me mindset.


There are three ways you can grow in self-awareness. One is to become more self-reflective. Actually pause and point the lens of attention back at yourself, as though there was something outside of you looking back at you.

The second way to grow in self-awareness is to create an incredibly feedback-rich environment where the people around you are giving you feedback -- the most direct form of it.

And the third way is to use some kind of personality instrument. You could use a technical instrument like the Myers-Briggs or another personality instrument. We love a tool called the Enneagram because it’s like a CAT scan in terms of self-awareness.

What are Enneagram types?

The Enneagram helps you see things about yourself you cannot otherwise see, such as your core motivations, blind spots, communication patterns, listening filters, style of relating to others, and path to maturity.

It is not an exact science. It is not there to pigeonhole people or to be an excuse for bad behavior. It is just a useful framework for understanding yourself and others a little better. And the better you understand someone, the better you can work together.

Typing yourself

  1. First take the test. This will take about 15 minutes and will reveal your base and wing type enneagrams. Add the result to your profile page in our wiki so others can discover it.
  2. Then read the description of your type on These descriptions are more modern and comprehensive than the descriptions listed on

The nine types

There are nine Enneagram types. People tend to have one dominant type and one minor (wing) type. No type is inherently better or worse than any other; all have assets and liabilities.

These type descriptions come from The Enneagram Institute.

1 The Reformer

The Rational, Idealistic Type: Principled, Purposeful, Self-Controlled, and Perfectionistic

2 The Helper

The Caring, Interpersonal Type: Demonstrative, Generous, People-Pleasing, and Possessive

3 The Achiever

The Success-Oriented, Pragmatic Type: Adaptive, Excelling, Driven, and Image-Conscious

4 The Individualist

The Sensitive, Withdrawn Type: Expressive, Dramatic, Self-Absorbed, and Temperamental

5 The Investigator

The Intense, Cerebral Type: Perceptive, Innovative, Secretive, and Isolated

6 The Loyalist

The Committed, Security-Oriented Type: Engaging, Responsible, Anxious, and Suspicious

7 The Enthusiast

The Busy, Fun-Loving Type: Spontaneous, Versatile, Distractible, and Scattered

8 The Challenger

The Powerful, Dominating Type: Self-Confident, Decisive, Willful, and Confrontational

9 The Peacemaker

The Easygoing, Self-Effacing Type: Receptive, Reassuring, Agreeable, and Complacent

Enneagrams in practice

Reading the description of your type is a good start, but where Enneagrams really start to shine is using them practically day to day.

Healthy and unhealthy traits

Every Enneagram has a light side and a dark side. It's worth digging into the unhealthy traits associated with your type to see whether you can identify any patterns you've fallen into. You can then start to catch yourself in the future when you see yourself reverting back to these negative patterns.

Interactions between types

We've found the description of each type's interactions to be a fascinating way of looking at two people in relationship. We suggest looking up your manager’s and close colleagues’ Enneagram types in our wiki and reading about the relationship between your two types.


Different types like to give and receive feedback in different ways. The Enneagram Group has put together a useful worksheet as a guide on how to give feedback to the different types.

Next steps

Listen to a description about your type. Ryan O'Neal has created a beautiful song and discussion around each type.

Exploring the opposite

The Wright brothers often took two different sides of an argument, debated the subject, then switched sides and debated the opposing argument. As Orville Wright put it, “Often, after an hour or so of heated argument, we would discover that we were as far from agreement as when we started, but that each had changed to the other’s original position.”

Our stories can lead to suffering

As we go about our day, we all are constantly interpreting the world around us to give our stories meaning. Often we can witness exactly the same events as someone else and yet arrive at completely different conclusions. How is that?

The stories in our head are a concoction of biases, childhood experiences, misinterpreted facts, and much more. A lot of suffering can result if we hold onto these stories too tightly and are committed to being right.

Almost all the challenges we experience arise from us believing we are right about the way we perceive situations, one another, or ourselves. To understand this, pick an issue that you are wrestling with in your life. When you look underneath, can you see your desire to be right about that issue?

The Work

In 1986, Byron Katie was coming out of the depths of a debilitating ten-year-long depression with a life-changing realization:

I discovered that when I believed my thoughts, I suffered, but that when I didn’t believe them, I didn’t suffer, and that this is true for every human being. Freedom is as simple as that. I found that suffering is optional. I found a joy within me that has never disappeared, not for a single moment. That joy is in everyone, always.

- Byron Katie

In other words, what was causing her depression was not the world around her, but what she believed about the world around her. Katie went on to create The Work, a simple framework for turning around beliefs in order to alleviate suffering.

Instead of hopelessly trying to change the world to match our thoughts about how it “should” be, we can question these thoughts and, by meeting reality as it is, experience unimaginable freedom and joy.

The four questions

There are four questions you can ask yourself to help turn thoughts around:

  1. Is it true? (Yes or no. If no, move to question 3.)
  2. Can you absolutely know that it’s true? (Yes or no.)
  3. How do you react, what happens, when you believe that thought?
  4. Who would you be without the thought?

The four questions in practice

For example, let's take the belief that "John doesn't appreciate my input" and go through the four questions.

  1. Is it true?

    "Sure, I remember he interrupted me mid-sentence last Tuesday."

  2. Can you absolutely know that it’s true?

    "I guess there's no way for me to know his true feelings."

  3. How do you react, what happens, when you believe that thought?

    "I feel angry. My chest tightens. It ruins any meeting that I'm in with John. I've been fuming about this all afternoon."

  4. Who would you be without the thought?

    "My mood would be lifted. I'd be a lot happier. I'd be able to collaborate with John again and appreciate some of the qualities I love about him."

So you see, instead of hopelessly trying to change the world to match our thoughts about how it “should be,” we can question these thoughts and, by meeting reality as it is, experience freedom and joy.

The turnaround

The next step is the turnaround. The idea here is to see that the opposite of your story is at least as true as, if not truer than, your original thought.

For example:

  1. John doesn't appreciate my input.
  2. Turn it around to the opposite: John appreciates my input.
  3. Turn it around to the other person: I don't appreciate John's input.
  4. Turn it around to yourself: I don't appreciate my own input.

Often we find that deep-seated anger with others is rooted in things we hate about ourselves; it's a projection. Regardless of the cause, these beliefs are causing us suffering. Realizing that you can turn that around will set you free and create lasting shifts in your thinking and your perception of yourself and the world around you.

But doesn't this lead to apathy?

Beliefs are very powerful, and negative ones can lead to a lot of suffering. By turning them around, you can alleviate your own suffering and then problem-solve from a place of playful curiosity.

Treat The Work as a meditation. It’s about awareness; it’s not about trying to change your mind. Would you rather be right or be free?

A full example of the practice

A great way of seeing the power in these simple questions is to take some real-world examples. Byron Katie has recorded a set of YouTube videos with her taking her guests through each question.

One such example is “my wife wastes her days.” A husband takes issue with the way his wife spends her time with the kids; he feels like he slaves away at work all day, and when he gets back home, he finds that his wife has wasted her day.

Byron: Is it true? Husband: Yes, from my perspective it is.

Byron: Can you absolutely know that it’s true? Husband: No.

Byron: How do you react, what happens, when you believe that thought? Husband: I resent her. I feel like I'm working my tail off and I feel like she's a child; I'm picking up after her.

Byron: Who would you be without the thought? Husband: She's beautiful. I'm excited to see her. She's probably been doing cool, creative stuff with our boys. I'd be honoring all the things she does for our world during the day. She does things for us all day.

Byron: So with the thought, you're angry and resentful. Without the thought, you're connected, grateful, appreciative. So how does your wife's day have anything to do with your problem? What you're believing in the moment is the obstacle you're holding between you and your connection with your wife. Beliefs are very powerful. You think the thought, it keeps you blind to your love with her, your connection with her, and everything she does give for your two children in your life.

Byron: So that thought, turn that around. Husband: She maximizes her days. I waste my day.

Byron: As far as I'm concerned, a day spent in resentment is a day wasted.

The purpose of The Work

The purpose of The Work is to become curious about all the possibilities of life. We find that this is done most effectively if you remain unattached to any outcome. This is not about valuing one thought above another, but it is about staying truly open to the exploration.

Gratitude & appreciation

Have you ever saved up for something, bought it, and then felt empty inside? Or perhaps you worked hard to achieve a goal, but realized the journey was more fulfilling than the achievement? This phenomenon is called hedonic adaptation: the idea that people return to a set level of happiness regardless of what happens to them.

In other words, as you earn more, acquire additional things, and achieve higher goals, your expectations also rise in tandem. Ergo, these things result in no permanent gain in happiness. The opposite is also true. When we get used to having less, it takes less to please us.

So naturally, after expecting happiness, but instead feeling emptiness, we start doubting it all. We start focusing on the negative so we continually see the negative. This leads to objectively very successful people being not fully satisfied with their lives.

So are we destined to feelings of emptiness and inadequacy? It's a fairly depressing prospect, and for many years I was resigned to this case. However, there is a simple tool we found that can transform your outlook: gratitude.

Practicing gratitude

In positive psychology research, gratitude is strongly and consistently associated with greater happiness. Gratitude helps people feel more positive emotions, relish good experiences, improve their health, deal with adversity, and build strong relationships.

Practicing it is so simple that it seems there must be a catch. First, you need a prompt to remind you to practice in the morning. We suggest having a Post-it note attached to your bathroom mirror that simply says "gratitude." Every morning when you notice it, repeat the statement "I am grateful for _" five times, and try to keep whatever it is you are grateful for as specific and timely as possible (names of people, specific actions they did, etc.).

For example, "I'm grateful to John for encouraging me when our revenue modeling was inaccurate." Or "I'm grateful to Jane; her presence has such a positive impact on my life."

That's all there is to it! We have seen that a regular practice of gratitude has a marked change on people's outlook, helping them focus on the important things in their life, the things they truly value.

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