Chapter 4. Career and Work

11 min readApr 1, 2017


Work is one of the things people worry about most. In this chapter, I focus on management and motivation. I think that understanding these topics benefit people the most. Better management and teamwork skills leads to better accomplishments and happier people. I also try to give some career advice.

Good Managers

Some managers are great, some are OK, and some are bad. Great managers are extremely valuable to the success of the company and to the success of their employees. It wasn’t until I got more experienced that I realized how much of a difference great managers can make.

A better manager will get the most out of the employees that he or she is leading. Unfortunately, many managers don’t know how to do this. Bad managers will actually cause their employees to be less productive. I’m hoping that as time goes on people will get better at management. It will make work less stressful for their employees. It will also allow better work to get done.

I’ve had great managers, OK managers, and bad managers. It made a huge difference in how much I enjoyed my job and how motivated I was to do good work.

How to motivate people

There are many books on how to be a good manager. But it seems like many managers don’t read them or adhere to their advice.

One book I read and enjoyed was called Drive: The Surprising Truth About What Motivates Us by Daniel H. Pink. It’s about what causes employees to be motivated to do good work. According to the author, the three keys to motivation at a job are autonomy, mastery, and purpose. Autonomy means having control over what you do. Mastery means the work allows you to grow. Purpose means working on something that you feel is a good use of your time.

It is important to delegate responsibilities rather than “micro-manage”. Not only does it free up more time for you, you’re giving the other person more autonomy, which is very motivating.

On the other hand, there are some things that are ineffective motivational tools. Rewards and punishments intuitively seem like a great way to motivate people. But in some cases, they are actually very demotivating to employees. It depends on the task. Doing a task just to receive a reward or avoid a punishment may make the task less enjoyable. Money is not always enough to motivate people to do great work.

Employees work best if they think their work is important

Employees and management sometimes disagree about which projects are best for the company. This can be very demotivating for the employees.

Imagine being me and being told to work on a project that I think is unimportant. I resented being assigned that project. I could think of dozens of things I could be doing that was more valuable to the company and the customers. I was frustrated because, in my mind, the company was not using my time very well. This example demonstrates why autonomy is important. I would be more motivated if I was working on what I think is best.

If an employee is not doing great work, it may be because that employee thinks the project is not important enough. Management can try to explain the importance of the project. Management can also try to explain why the project is higher priority than other possible projects. But management should also listen to their employees. Great management will understand what employees think is most important.

I’ve experienced this at work. Some projects I did great on because I really wanted to work on those projects. They were projects that I believed were really important. On the other hand, the projects that I thought were a waste of time were very demotivating. I did not put forth much effort on them.

Communication and empathy can improve teamwork

Good teammates empathize with each other. However, this can be very hard to do. Each person has different ideas and values. Each person might also have a different stake in the project’s success. Teammates can have very different backgrounds and previous experiences.

The best way to empathize with teammates is to talk to them. Ask what they think is important and why they are passionate about those things. Don’t make assumptions about why they do something a certain way. Instead, ask them why they do things that way. Ask them to explain their ideas. Their answers often surprise me. You might learn a lot about them. If you don’t understand your teammates, you can’t work with them very well.

There have been times at work when I felt like my teammates didn’t empathize with me. This made it very demotivating to work with them.

Really listen to your employees and teammates

Employees don’t always share their good ideas. They might not have the courage or opportunity to speak up. Great communication is difficult but very valuable. Companies can suffer if the good ideas aren’t being heard by the right people. Management does best when it really listens and responds to employee suggestions. Listening to your own employees can be much more valuable than trying to imitate what other companies are doing.

It’s very frustrating to the employee if their feedback is ignored. The employee will be demotivated and not do their best work. Ignoring feedback also makes people less willing to share important ideas again in the future. If you notice someone’s work change dramatically, it could be because they don’t feel heard.

My least favorite times at work were when I felt like I had good ideas but those ideas were being ignored.

Feedback is only useful if it is understood

If you’re a manager, you should try to constantly give feedback about an employee’s performance. Make the feedback clear so that the employee understands it. If you’re an employee, frequently ask your manager for feedback.

Sometimes feedback and expectations are misinterpreted. One time my work was criticized by my manager but this feedback was given to me in a way I didn’t understand. I think I was told to be more like [this other guy working there]. But I didn’t know what that meant. And while the other person was someone I had a lot of respect for, it wasn’t someone that I looked up to or knew how to use as a role model. The message wasn’t conveyed to me clearly. This meant I didn’t realize how my manager wanted my work to change.

Try to think of what you can do better before blaming others

It’s easy to blame others when things go wrong, but it’s not helpful. Imagine someone on your team is awful and makes work miserable for you. You might feel that it’s a valid excuse to blame them for your team’s poor performance. That’s what I did once, unfortunately. But if you really want to be successful, you are going to have to overcome obstacles.

Thinking about how other people made things harder for you will only make you angry. Instead, think about how you can ensure your success in spite of all the challenges.

Maybe you have a manager that is extremely demotivating, like I’ve had at times. On one hand, your manager is making it harder for you to be motivated. On the other hand, you need to step it up and get motivated anyway.

You have to be responsible for your own motivation. If you blame your manager for a poor performance, no one will take pity on you.

In fact, reading about good management vs. bad management had a demotivating effect on me because I became more conscious of what management could have been doing differently. I should have focused on what I could be doing differently. (I would’ve been better off reading a book about how to be a good employee instead!)

Make it clear when someone is at risk of losing their job

Losing your job might be a complete surprise. I think this is even worse. If you’re a manager and you’ve started thinking of firing someone, you should let them know.

Once I lost a job completely unexpectedly! If I had known that I was at risk of being fired or laid off, my work performance would’ve been a lot better.

Don’t feel bad if you get fired from a job

You might get fired or laid off. This might make you feel terrible about yourself and your career. You might feel that it is an injustice. Maybe your employer is undervaluing you and making a huge mistake.

Some people can move on quickly from losing a job, even if they are angry. Other people will feel really bad about it and not be able to move on quickly. I probably let losing a job slow me down more than it should have.

Try not to feel too bad when you lose your job. Instead, keep moving and keep doing great things. You might learn and grow a lot more from being fired. People don’t talk about it a lot, but losing a job is pretty common.

Don’t be afraid to quit a job

Quitting a job can be really scary. It can be even more stressful than getting fired. You started the job hoping it would be amazing but it turned out to be terrible.

I had to quit a job once. It was very difficult because I didn’t completely want to leave the company. But leaving allowed me to move forward.

You might feel stuck. Your job might be a big part of your identity and confidence. You might have family, friends, and co-workers telling you not to quit yet. You might feel bad about not staying long at a job.

Don’t be afraid to quit your job. If you hate your job, your life will be so much better off without it. Being miserable at work means you will be constantly worried about your job outside of work. If a job is bad, it is unlikely to get better! You don’t owe that company anything. You owe it to yourself be courageous enough to find a job you love. When I quit a job, my biggest regret was that I didn’t leave sooner!

Don’t be afraid to fire someone

Some managers don’t fire a bad employee soon enough. The manager might be afraid of the awkwardness. Maybe the manager is afraid of being short-handed.

A bad employee can create as many problems as they solve. It’s better to have one less employee than one really terrible employee. A bad employee makes other teammates uncomfortable, frustrated, or very demotivated. They get in the way of other employees by making work more stressful.

Some bad employees are fixable. You just have to figure out what motivates them to do good work. But other employees are not fixable and will just continue to bring your team down.

One time I had to work with a terrible teammate as my partner. This was very stressful and demotivating. At the time, I didn’t even know how to deal with it. I wish I had done more to try to improve the situation, either by talking to him or talking to management.

Meaningful Work

You’ll work harder if you think your job is meaningful. Work is meaningful if there are motivations besides money. For example, you might genuinely enjoy helping your customers through your work. Your work might feel like it is fulfilling your purpose or your calling.

Different people care about different things. If you understand what your teammates care about, you can help them be much more productive.

The Invisible Hand of Meaningful Work

Generally, people want to both make money and do good for the world. In economics, the “invisible hand” is what creates wealth for a society when individuals are working to create wealth for themselves. There is a similar effect with meaningful work. Imagine that, on average, every person’s work makes the world a tiny bit better. The sum of everyone’s contributions will be a huge benefit to society.

Value yourself

It’s important to value yourself. Some people underestimate the worth of their own time and energy. If you think your worth is very low, you can be taken advantage of.

For example, imagine you are working as an unpaid employee. You might think it is worthwhile because you’ll gain valuable experience. But you are already undervaluing yourself. If the work you are doing is very helpful, it is worth a lot to your employer. Your employer may undervalue the work you do because it is not costing them much. (You might think that no one is foolish enough to work for free… but I’ve seen it happen!)

You are responsible for making sure you are getting a fair return on your time, energy, and resources. Try to make good investments in yourself so that you can become more valuable or become valuable for new reasons. Most people can be very valuable in the right situation.

Look for jobs everywhere

There are many ways to get a job. The first is to look through a list of job openings. There are lots of places that list job openings: job fairs, job search websites, LinkedIn, Craigslist, etc. There are many resources to help you find job openings.

The second is to “network” and ask people you know about job openings.

The third way is to take risks and find jobs in unexpected ways. For example, I once got a job as a programmer because my dad talked to a stranger in the neighborhood who happened to own a software company. It was very serendipitous but it led to a successful job interview and a job.

Another bit of luck was when I was applying to my first programming job. I didn’t have much programming experience at that point in my career so my resume still included that I had successfully published comic strips. To most programming jobs that would be completely irrelevant. But it helped me stand out to someone who was looking at my resume and building a software project for artists and designers. So you never know what will lead to your next career opportunity.

Show off your passion during an interview

Obviously, job interviews are designed to test your knowledge, skills, and qualifications. When I started interviewing candidates for a programming job, I realized how important it is for candidates to also demonstrate passion. I was much more likely to score a candidate well if he or she displayed knowledge of and enthusiasm for our product.

Don’t be afraid to start doing something new

The hardest part of any accomplishment is usually getting started. This is something that I’ve struggled with. There are many cool things that I wish I had tried sooner.

You don’t need anyone’s permission to do something cool. You don’t need a perfect opportunity. You don’t need the perfect teachers, mentors, or education. You don’t need the support of your friends and family. Really all you need is to go for it. You can learn as you go.

The worst that can happen is you fail spectacularly… but is that really that bad? In that case, just move on. It’s unlikely that the failure will have a negative effect on your life. Instead, you probably learned a lot from trying.

The rewards for trying something without fear can be great. You might learn a lot. You might make new friends. You might gain new skills and create new opportunities.

Stay in touch with former co-workers

Staying in touch with former co-workers is very difficult. You will be busy, the other people will be busy. You might be afraid because you don’t know them that well outside of work. You might have a lot of assumptions about them.

The rewards are huge. They can help you with your career and your life. You can help them too. You might learn a lot from them. You might become closer friends with them.