1 Own your career

Many of us see the word success and think of a big salary or an important job title. Instead, success should be seen as a set of criteria that you define and that represent a career capable of supporting the personal life you want. A career plan is a plan to achieve that kind of career.

1.1 Job, career, success, and self

Let’s begin by quickly defining some terms so that you and I can be on the same page. I define job as a set of tasks that form a role you’re paid to do: a software developer, a data analyst, a systems administrator, a network engineer, a security specialist, and so on. A job is an arrangement in which the employer offers compensation to someone and that someone performs the requested job tasks. If you weren’t doing the job, someone else would be. In other words, your employer owns the job. That means your employer bears a lot of responsibility for the job: they have to provide you the tools you need, they have to tell you which tasks need to be performed, and they get to define the standards that you have to adhere to when performing those tasks.

Your career, on the other hand, belongs to you. Your career encompasses all the skills it takes to obtain, keep, and perform the jobs of your choice, and you may have several different types of jobs over the course of your career. You are responsible for your career: you get to decide where it is headed, and you have to pay for any of its upkeep that falls outside the scope of your current job.

So, your employer owns your job; you own your career. Suppose that you’re a software developer working on in-house applications written in C++. You’ve been doing this for a while, and you’re eager for a change. You’re also a little concerned that being great in C++ doesn’t offer many job opportunities in the world, and you’re—wisely—worried about getting stuck in a rut by working in a language that’s not too common.

You decide that you’re really interested in web development, and you’d like to take a class in advanced JavaScript programming. You also want to attend a conference on web development so that you can get a handle on all the various technologies that come together in web applications. But your employer refuses to pay for either the class or the conference. Should you be upset?

I would argue that no, you should not. The class and the conference aren’t connected to your job, meaning that neither the class nor the conference will do anything to make you a better C++ programmer, which is what your employer pays you for. Instead, the class is something you want for your own career. You want to expand the set of skills contained in your career, both to satisfy your own interest and to expand the job opportunities available to you. Therefore, you should be the one paying for the class and the conference, not your employer. But as you’ll see in chapter 5, expanding your hard skills is an important aspect of maintaining your career. So don’t cancel your class or conference just because you’ll have to pay for them.

There’s a downside to “owning” a technology career, in that it can be expensive. But there’s a definite upside to owning a technology career too: you can make it serve your bidding. Your technology career can be a powerful means of achieving . . . well, just about anything you might want it to!

But what should you ask your career to do for you?

1.2 Start at the beginning: With yourself

Too many of us graduate from school, get into our first real job as an adult, and immediately start trying to do the best job we can. We manage to impress our employer, and in time, we’re offered a promotion. Or perhaps we gain enough experience to land a better job elsewhere—one that pays more, offers a better job title, or has other upgrades.

Without really thinking about it, we start to equate success with salary, job title, the size of the team we lead, and other criteria. But we rarely stop to think, “What’s it all for?” That’s what I’d like you to do right now: stop and think, “What’s it all for?”

What kind of life do you want to live? How do you want to spend your time, both on and off the job? What contributions do you want to make to the world? What passions and experiences do you want to pursue?

I want you not only to stop and think about these questions, but also write down your thoughts. Writing things on paper with a pen or pencil helps you take the thinking seriously—and helps you remember your conclusions.

Your answers to these questions clarify and define the life you desire, so I call this piece of writing your life definition. Unlike other definitions, your life definition may change as you enter new phases of life and discover new goals and values. My current life definition is not the same one I’ve always had. As I’ve grown older, formed a family, and changed interests, my definition has changed. That’s fine; that’s what being alive is all about! But I’m careful to document, in writing, what I want from my life. I revisit this definition annually, and I treat it a bit like punching in a destination into a GPS app, in that this life definition is my destination. When I get there, I want to stay there, unless something happens that prompts me to rethink what I want from life.

One more thing before you start thinking and writing: I want you to write this life definition as though you were on the outside of your life looking in. Not to be depressing, but treat this definition as though it were a kind of extended obituary. It should represent what you want your life to look like when you’re looking back on it. Writing it this way can help you distill your most important dreams, goals, and desires. To show you what I mean, I’ll share my current life definition.


This is what I want my life to look like when it’s all over. I want you to take note of a few specific bits in this life definition:

  • Money is implied in my definition because I’ve listed some things that will clearly require money to achieve. At this stage, however, I’m more interested in describing what I want than worrying about how much it will cost.

  • I’ve described the types of jobs I want to take. Work is, after all, a big part of life: most of us spend a third of our lives working. It’s important to me to have a job that I find satisfying and that provides the income I need.

  • I’ve listed things that I haven’t yet achieved, even though I’m pushing 50 years old. I may not ever achieve all my goals, but I’m pointing myself toward them.

  • I’ve included some things about my personal life that will require time, which in turn creates certain implications for my work life. I need a job that will give me free time to work on writing novels, for example, which means that I probably won’t be working for hard-charging startup companies that need 20-hour workdays.

My life definition is the destination that goes into my “GPS of life” app. Everything I do is meant to drive toward that destination. My life definition is what it’s all for. It’s why I get out of bed in the morning; it’s why I work; it’s why I live.

Please write it down . . . on paper

Human cognition—the way we think and learn—depends largely on our senses. The more senses are engaged in a given experience, the more lasting and powerful the resulting memories are inside our brains. That’s why we can have such strong memories from our childhoods. The smells, the sounds, the sights, even the taste of the churro add up to that memorable moment at Disneyland.

Typing on a computer doesn’t engage many of our senses. Our sense of touch and even our sense of sight barely register what we’re doing: the words simply flow onto the screen, as they’re meant to do.

But when you write down your definition of your life, you want your brain to be deeply and deliberately engaged. You want to be thoughtful, and you want the words you write to be branded into your mind. That way, those words will always be more present for you, helping you remember what it’s all for.

That’s why I’ve always written my life definitions over the years, using a sharp pencil and a quality notebook. Even sitting here typing this book’s manuscript into a computer I can smell the leather of the notebook cover, feel and hear the scritch of the pencil

against the page, and feel my hand traveling across the page. Those sense memories instantly bring the key elements of my life definition to mind. I didn’t even need to go get my journal to offer you the example I did, because my definition statements are indelibly carved into my consciousness. They’re always top of mind—as they should be.

With my life definition—my GPS destination—firmly in front of me, I need to figure out what it’s going to take to get there.

1.3 What does success look like for you?

For me, success is simple: it’s whatever it will take to get the life I want. Success is literally a bulleted list of things I need to achieve that life I’ve envisioned and defined. If my life definition is what goes into the “GPS of life” app, my success is whatever parts I need to build a vehicle that will take me there.

Consequently, success is not something I pursue endlessly, but a specific set of measurable goals that I can slowly work toward. I will know when I reach those goals, and at that point, all I need to do is maintain that success rather than try to continue growing it. I never feel that I’m in a rat race, endlessly pursuing the next-bigger piece of cheese. Instead, I’m pursuing specific, achievable goals that will help me live the life I want.

When I write down my life definition, I also write down my success definition. To create my success definition, I usually start with the life definition and then add bullet points that describe what it will take to achieve my outcomes—aka my life definition. As much as possible, I try to keep the success bullets objective and measurable, so that anyone could look at my life and decide whether I’d met a given goal. That’s not always possible; some things, especially more qualitative things, are always going to be a little subjective. That’s fine; try to be as objective as reasonably possible. My idea of a great vacation, for example, isn’t something that I can easily quantify; it even shifts a bit from year to year. I might be able to think only about ranges or guidelines, and that’s fine. Here are some examples of my success definition, using a portion of my goals from my life definition:


This example is pared down, but I wanted to highlight some sections that are a little bit subjective, as well as some (such as the salary calculation, which is a made-up number for this book) that are objective and easily measured. Some items are definitely aspirational, as they’re things that I hadn’t yet achieved when I wrote them down.

It’s important to note that I don’t change the success bullets unless I’m changing the life definition or unless life itself has changed around me. I don’t plug in a larger salary number for no reason, for example. Instead, if I’m feeling that I need more money from work, I look at why. Has the cost of living gone up? Did we decide to adopt a kid? Have we been visiting more-expensive places than I anticipated? Whatever the reason, I need to decide what has to change in my life definition to justify the need for a larger salary. Have we been eating out more than we should and spending more on food as a result? Maybe we should decide to stop that. Or if eating out is something that we love and want to continue, I need to modify my life definition accordingly.

The point is that my success is there to support my life. Nothing goes into my success definition unless I know why it’s there, which ensures that I’m not randomly chasing a larger salary or pointlessly pursuing a job title for the glory of it. Whatever I’m doing with my career, I’m doing it because my life needs it. With those success bullets in mind, I can start crafting a career plan.

1.4 Creating a career plan for right now

If your life definition is the destination you plug into your GPS, and if your success targets are the parts of the vehicle that will get you there, your career plan is the route that the GPS spits out. Follow that route, and you’ll get there.

With a good career plan, however, you don’t need to know the entire route at the outset. Instead, you can think about the next few steps on the journey and plot them out for yourself. So long as you’re always pointing to your ultimate destination—your life definition—you’ll get there eventually.

To create my career plan, I start by looking at the success bullets that support the components of my life definition. Some of the success targets might be too hard for me to imagine reaching. Become a company vice president at 25 years of age? Hah! Instead, I focus on the bullets I can achieve or at least see a path to. Rewinding my mind over two decades (and consulting the notebooks I wrote everything in), I see things like this:


Okay, at 30 years old, I definitely lacked the experience to get a role as senior director or vice president. But by then, I’d led a small team, and I’d started to understand what running a business was all about. So I made a point to land a director role, specifically with a company that would be interested in investing in making me a better business leader. With that as a job-hunt focus, I was able to find a role within my current company at the time. The pay wasn’t as much of an increase as I’d wanted, but I was more focused on getting the experience I needed to move toward my goals.

And that’s what a career plan is: a way to move toward your goals, to slowly tick off all those success bullets. Focus on the ones you can achieve now, and for the others, start researching what it would take to achieve them. I spent quite some time on job boards, for example, looking at what was being asked of candidates for vice president jobs. I knew that I’d need credentials such as these:

  • 10 or more years managing teams of however many people

  • More than five years in a position with financial accountability or outcome accountability

  • Ability to manage teams with more than four layers of people

  • Experience managing up into the executive suite

I didn’t have those qualifications, but I could start to see the path toward them: start with a small team, ask my boss to share accountability with me, ask to give an occasional presentation to the company executives. Again, meeting all these goals required working for someone who was willing to make those investments in me, and my job hunting was aimed sharply in that direction.

Scouring job postings is a wonderful way to build a career plan. At one stage of my life, I realized that my next move needed to be an increase in salary—not a huge one, but I was pretty much maxed out in terms of where my current job would take me. In fact, I came to realize that the field I was in was unlikely to offer more money, so I needed to change fields, moving from systems administration to software development. Boy, was that scary. I needed to pay for the necessary education myself because my then-current employer had no reason to pay for it. But I did it. I eventually got a job as lead web developer and wound up in charge of a small team, which also put me on track toward my leadership goals.

Obviously, the process took a while. Life can be a long journey. But at age 46, I finally did land my vice president role. Career plans work.

1.5 Action items

In each chapter of this book, I offer you an exercise. I strongly recommend that you do these exercises, because each one will help you start mastering the soft skill covered in that chapter.

For this chapter, as you can probably expect, I’m going to ask you to get a paper notebook and a pencil (unless you love pens, which is fine), and write down your definitions of life and success, as well as make a first pass at a career plan. Work with your family and friends on this task; they’re stakeholders in your life, and they need to be represented in your life definition:

  • Start by writing your life definition as you see it. Given who you are and where you are in your life right now, what can you imagine doing? If you find it difficult to to think about this definition as a set of end-of-life retrospectives, then instead, focus on what you, at this point, find valuable about your life and what you want in that life for the foreseeable future. If you have clear goals, write them down as well.

  • Go on to your success bullets. What will it take, from your career, to meet your life goals? Get serious about the math in the appropriate spots; know how much money you’ll need to make to get what you want. If the number seems to be unattainable, go back to your life definition and decide what you can live without, but try to make the life/money equation balance. In other words, for whatever you’ve said you want from life, make sure that you provide a good estimate of how much money that will take.

  • Finally, start thinking about the single next step in your career plan. What one, two, or few things could you change about your career to achieve one or two of those success bullets, such as a better-paying job? Do some research, figure out how to take the next step, and then start executing that step.

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