How to write the best resumé of your life, Part 1: What, Why, and How

April 11, 2016

Hello, thanks for joining me! Welcome to the first in my three-part series on how to write the best resumé of your life. Part 1 will cover the pre-work that goes into writing a great resumé, and will lay some foundations for the processes you will follow in Parts 2 and 3.


Part 1 Overview

I’m going to cover three important ideas in this post. First, what a resumé is; second,why you should write a resumé; and third, how to write a resumé. Lastly, in the interest of putting my money where my mouth is, I’ve done something I have seen no other resumé advice writers do: attached my own resumé to the end of this post. This was the most intimidating thing I could imagine, so it seemed like exactly the right thing to do.


What is a resumé?

I most often see resumés described as advertisements. After all, they market a product (you) and have a metric for measuring success (getting an interview). Personally, I don’t like thinking of resumés like this because you’re not a product; you’re a human being. And, while you have certain skills you must market, you also have a personality, beliefs, goals, and dreams—characteristics which are enormously important to your professional career, and which should be hinted at in your resumé, if not directly mentioned.

So I think of resumés a little differently. My thinking is this: Human minds make sense of the world with stories, so for everyone, work is more meaningful when it fits into a larger story. And all stories, of course, need characters. That’s you! So think of your resumé as a description of your professional character: the professional roles that you can play, as it were. If you can make your resumé a compelling character description, then those who read it can quickly evaluate whether or not your character will fit into their company’s story. Both you and the companies you apply to want a good fit, so it’s crucial to think hard about the role that you want to play.

Crafting a compelling professional character goes beyond simple job titles and descriptions. In a story, bad character description tells us what someone looks like, while great character description tells us what kind of person someone is. Similarly, a good resumé should tell us not merely what you’ve done, but what you’re like as a human being.

Let’s look at an example of bad character description: “She was a middle-aged woman with light brown, shoulder-length hair. Her eyes were also light brown. She was tall and thin, and usually wore baggy jeans with a patterned knit top.” None of that insipid visual detail actually tells you anything about the character, and yet that’s what most resumés look like: “Software engineer with 12 years’ experience. Strong skills in C+, SQL, C++, Java, C#, C++++.” Blah, blah, blah. That is dull and forgettable, and fails both as a character description and as marketing (if you must persist in thinking of your resumé that way).

Now look at this fantastic character description, courtesy of Dennis Lehane’s A Drink Before the War: “Sterling Mulkern was a florid, beefy man, the kind who carried weight like a weapon, not a liability. He had a shock of stiff white hair you could land a DC-10 on and a handshake that stopped just short of inducing paralysis.” Look how Lehane uses Mulkern’s appearance to describe what kind of person he is (strong and confident with a hint of violence about him). Your resumé should communicate your strengths with similar clarity; use your work experience to describe who you are. Your goal is a clear and memorable description of your professional self.

Speaking of memorability (memorableness? memorabilia?), I see a lot of talk out there about the amount of eye time that your resumé is likely to get from hiring managers (it ranges from 6 to 20 seconds). The result, they say, is if you can’t grab their attention in that window of time, you’re screwed. Thankfully, that’s nonsense. Anyone who believes that is thinking of resumés like fragile little birds released in the wild to live or die at the whim of mother nature. But not you. Your awesome resumé, which you poured so much time and effort into, is more like your child, right? You’ll follow up with as many emails or phone calls or random drop-ins as it takes to get someone to look at it, right?! And if, after all of that, your bang-up resumé still doesn’t get any love, well, why the hell would you want to work at that company, right!?! They obviously don’t have their shit together.

What is a resume? It’s just a piece of paper, of course. And no piece of paper ever commanded attention on its own. But on that piece of paper is an amazing description of your professional self, and once you make someone look at it, there should be little doubt in their mind about what kind of person you are.


Why write a resumé?

If you have time, I will boldly send you away from my blog post to take a look at Richie Norton’s free (and short) ebook Resumés are Dead and What to Do About it. He makes some excellent points about the modern world and how we communicate our skills to one another, culminating in his conclusion that people should craft their own businesses and work schedules and tell their story with a portfolio of work. I think Mr. Norton misses on a couple of points. First, he presumes that we write resumés solely for the purposes of getting jobs. Second, he assumes that everyone wants to engage in what Tim Ferriss calls “lifestyle design,” where by and large you work for yourself and are beholden only to your customers. Third, he overlooks one of the key benefits of the resumé: brevity. I take issue with each of these.

First, whether you work for the government, a large or small corporation, or for yourself, writing a damn good resumé is at least a wonderful exercise in self-discovery and self-branding. Spending the time rigorously thinking through where you are professionally reaps huge rewards in reorienting yourself toward achieving your professional goals. Maybe you’ve been pigeonholed as a software engineer for so long that you forgot you wanted to try teaching. Or maybe there’s been a lovely idea for a book buried in you for years. We forget these things if we don’t revisit them—if we keep ourselves distracted with the work that we’re doing. Putting your professional self on a piece of paper can bring to the surface long forgotten parts of who you are. Even if no one else ever looks at your amazing resumé, it’s worth it to write one.

Norton’s second assumption is even more misguided than his first. I have met many people who simply aren’t interested in lifestyle design, who much prefer to work their nine-to-five job and take two weeks of vacation a year. There is absolutely nothing wrong with this. But almost without exception those people still want to advance their careers, make more money, and create a space within their worldview to grow themselves professionally. And until all the old-school hiring managers at traditional companies have died off, they’re still going to expect that piece of paper on their desk.

Finally, in contrast to Mr. Norton, I believe that maintaining a resumé is the best and most succinct way to summarize your professional character. By all means, keep a portfolio of your work or make a video introduction as he suggests. But I will always be able to learn more about a person by spending a single minute looking at their badass resumé than I can by watching their five-minute intro video or spending 10 minutes trying to figure out the scale of the work in their portfolio.

Why write a resumé? When it comes to describing your professional self, they are cheap, quick, effective, and familiar.


How do you write a resumé?

By the way, for Part 1 here, I’m going to discuss mostly the principles that underpin stellar resumés. I’ll be speaking in some generalities, but don’t worry; specific examples of what I’m talking about are coming in Parts 2 and 3.


To write a resumé, first get ready to put in some time. A smashing resumé is not a one-and-done sort of document. You need to work on it at least once a month—whether or not you’re planning on applying for jobs anytime soon. Don’t think of your resumé like your great-aunt Bess, whom you see once a year (if that) at Christmas and make 5 minutes’ of small talk with and immediately forget everything she said. Instead, think of it like your sister who lives across the country, whom you’re fairly close to; you chat once or twice a month, and though you aren’t drastically involved in each other’s lives, you know pretty much everything that’s going on. Having a beautiful resumé is a commitment to documenting your professional journey on a regular basis.

Here’s how much work it actually is: I have spent at least 5 hours working on my resumé in the past month—and I work for myself. The lessons that I’ve learned about my professional self have been invaluable, and every time I revisit my resumé, I have a new self-realization or find something to improve. This points back to what I said earlier: The resumé is more than just a tool to get a job; it’s a vehicle for self-discovery.

Do character research

Second, before you even start to write, you need to get your story straight and figure out who you are as a professional. As a starting point, consider your answers to the following questions:

  • What do you do (as in, your job title)?

  • How do you describe what you do to others?

  • Why do you do what you do?

  • What do you like about what you do?

  • What skills do you have that make you good at what you do?

  • What is hardest about what you do?

  • What do you want to do?

  • Why do you want to do that?

  • What are you bad at (don’t judge yourself for it)?
  • What are you good at?
  • What balance do you want to strike between what you’re good at and what you enjoy doing (if they’re different)?

I could go on. There are dozens of questions to consider, and each one takes time. Remember how a scintillating resumé is like a great character description? Well, this reflection process is how you figure out what kind of character you are. You need to know what you’re good at—what you’re truly good at, not what you only wish you were good at. You need to know what you’re bad at—without judging yourself for it. You need to know your professional goals and you need to have actually committed to doing whatever is necessary to pursue them.

If thinking about these things is uncomfortable, good. That means you’re on the right track; self-discovery is uncomfortable at first because it requires honest introspection. The point is that you have to think critically yet nonjudgmentally about yourself in order to describe yourself well. Give yourself permission to be bad at the things you’re bad at so that you can identify the things you’re phenomenal at. Next, discuss those things with someone who won’t judge you: a spouse, friend, or close colleague.

Depending on your natural level of self-awareness, the above process might take an hour or two, or it might take weeks. I never sat down to actively engage in this kind of reflection (I developed the process in hindsight), so it took me about 4 months. Here’s what it looked like from my point of view:

Though I only recently became aware of it, my professional image was strongly influenced by the things I heard about the importance of 21st century skills. I was constantly reading and being told that things like creativity, problem solving, organization, and teamwork will be critical for success in future careers. For years I touted how good I was at those things, not because I actually thought that I was good at them, but because I thought I had to be good at them to be successful. And I never even noticed I was doing this. But after reading some impactful books and working some challenging contracts, I slowly began to realize the truth: I kind of suck at all of them. I had a conversation with my friend Mauricio about this realization. He confirmed what I said with absolutely no judgement, which was a great feeling. When I stopped worrying about not being good at the things I was “supposed” to be good at, some things became very clear. For example, it didn’t make sense for me to work with startups anymore, because I don’t like working on teams. But admitting my weaknesses allowed me to recognize the things that I’m actually good at, like teaching and writing and working with people. I had to find the difficult balance between working with people (strength) and being on a team with them (weakness). These are the kinds of valuable tensions that become evident as you think through your professional personality.

By this point, you will have a few clear strengths and weaknesses in mind or written down, and will have discussed them with a friend. That’s the core of your professional character, and will become the heart of your resumé. Don’t worry if you don’t feel perfectly clear; once you start the writing process, things will evolve and settle into place, and you’ll probably have more realizations about yourself.

Read up on the business story

Now that you have a rough professional character outline for yourself, you can start to investigate the businesses you’re planning to apply to and decide how your character will best fit into their stories.

Most of the advice I’ve seen is that you should tailor your resumé to the job that you are applying for—that is, write your resumé specifically for that job. In fact, on many other sites this is their first step in writing a resumé, as opposed to the self-reflection that I recommend. I disagree with their advice, of course. Remember, your resumé is about you first. It’s about your journey, your story, your professional character. If you start writing your resumé from the perspective of “Acme needs someone to sort widgets. I can sort widgets,” you’re doing yourself a huge disservice. Instead take this position: “I can dream up amazing new widgets better than anyone, and Acme needs ME!” Tailoring your resumé to a job posting is compromising who you are as a professional, an individual, and a human being in order to get a job. And if you start compromising yourself right at the beginning, you’ll be doing it the entire time you have that job. If you’re looking for your dream job, look inside yourself first—not to some company.

But don’t be dumb, either. If a job opportunity comes along that looks interesting, do your research! Find out about the company. Start with their website, then find some of their employees and customers. See if there’s any information out there about what it’s like to work there, what the company culture is like, and whether the mission and vision are genuine or just marketing bullshit. When you do the research to get this information, you will be much better prepared to have an informed conversation with them. You will have the chance to approach them as an equal who knows exactly how exciting this opportunity is to you, instead of being a supplicant who “just needs a job.”

How do you write a resumé? Commit to the process, reflect on your professional self, figure out how you want to fit in at the company you want to apply to (then come back and read Parts 2 and 3 of this blog series)!


That part at the end

If, having read these points, you are currently asking why for the love of god you would ever put that much work into your resumé, I invite you to ask yourself one simple question: What is your professional success worth to you? If you believe (as I do) that success is not measured in money or power, but in personal growth, self-knowledge, and a feeling of purpose, then the hard work of crafting a pristine resumé for yourself will return vast rewards along those lines. And, hell, if you DO measure success in money and power, then putting in the effort to write an overwhelmingresumé will pay off there, too. In fact, the only reason I can think of to not commit to following the guidelines I set forth in these next few blog posts is because deep down you don’t believe you can be successful. And that’s not a problem with your experience, your qualifications, your intelligence, or your work ethic. That’s a problem with your attitude. And no resumé, no matter how mind-blowing, will fix that.

Now that all of that’s out of the way, let’s begin. Decide that you and your professional self are capable of success and worth the effort! Grab a cup of coffee, sit back in a comfy chair, and let’s get to work writing the best resumé of your life. Part 2 is here!

(Oh, and like I said, here’s my resumé if you want to check it out.)

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