the art of career storytelling (for better resumes, interviews, and self-awareness)

As you know, most people don’t like working on their resume content. The endless tinkering can feel asinine.

If that’s how you feel though, you’re in the right place. Because refining resume content ought to increase, rather than decrease which is often the case, self-understanding and confidence.

I think we’ve all had the experience of tinkering with content and, in the process, felt like doing so took you further and further away from what you wanted to write as your fears and other people’s opinions were incorporated.

So where do you begin to finish with the feeling of satisfied completeness?

You start with the original content. The unedited stuff that you first plop down needs to be completely reflective of you.

If you don’t like what you’re starting with, the task of developing resume content is going to feel at best annoying and at worst uninspiring and endless.

So how do you get better raw and original content to work with? Does getting better content take longer? And, is this going to be harder than it already is?

(If you’re not wondering, I would be if I were you. So I thought I’d put it out there first.)

What I’m proposing is a step that doesn’t make things take less time, but that doesn’t take any more time than absolutely necessary.

I’m not looking to waste your time, I’m looking to get you what you want.

This step is asking you to do something different and it’s probably something new even though it’s something very familiar. And doing this step that you’re going to take right here is what makes the rest of your resume making so much easier.

The success behind a great resume – one that you feel pleased to represent and that gets you the job you’re happier and more at peace with – happens when you take ownership of your story. And your own career storytelling is what this step is all about.

You are about to “mine” where the hidden gems are. You’re unearthing them. This way there’s nothing to “make up”, there’s just stuff to “dig up.” And since there are gems, not zombies, it’s good stuff you’re digging up.

To prepare for what’s next, here are the three preparatory suggestions:

1. Have your current resume printed and ready for viewing;

2. Open up a fresh clean electronic document or find yourself a nice notebook and pen that you want to write with.

This document or notebook is purely devoted to career storytelling. This is NOT your resume. It’s your mental, emotional, and psychic creating space.

It’s going to look like a mess, but if you judged a gem by how you found it in a mine, you would think you’re looking at a worthless rock. After you find the gem in rock form, the step that follows is about polishing and cutting the gem to whatever level of perfection appeals to you.

For now, just be prepared to make a glorious mess.

3. Set aside 20-90 minutes per writing session OR only write about one previous job per session.

It’s better to have shorter and more frequent sessions than a whole uninterrupted day of resume writing. How many sessions you need is completely up to you.

When I work with a client, we tend to end up spending around 20 – 60 minutes per job that appears on the resume and we take 20 – 30 minute, whole day, or two-day breaks depending on how we’re feeling. Always check in with yourself to know what you can do and how much of a break you need.

In terms of a mindset as you approach this step, consider that you’re not sprinting nor running a marathon to the finish – you’re learning how to run. So the last thing you want or need right now is to sustain an injury by making this anything but fun. This is why you create this resume long before you ever need it. And when you need it, you’ll be beyond grateful that you have it. It will practically point to what job is next, which is pretty darn cool (and I know I’m not very cool for saying that).

Perhaps it goes without saying, but I’m going to say it anyway because I know how we humans get when we work on something like this:

Keep your mind open and curious about yourself. That’s the real magic in this process because anytime you block off or try to corral yourself, you won’t recognize gems when you come across them. Gems can’t be polished and still embedded in a rock at the same time.

What else is useful to know?

You don’t have to begin working on the content in a particular order. In fact, I encourage you to look at your resume and start with the job that you have the most affection for. If you find yourself agitated, angry, annoyed (or any other negative feeling) thinking about any of your past jobs put a star beside them for now.

Because you run a very high risk of viewing this task as unpleasant and don’t trust the process yet, I strongly suggest that you start with the job that you are going to have the easiest time with. Once you begin to experience the process, the jobs themselves become irrelevant because you’re applying a process to them regardless of how you feel about them. You will start to have new perspective on yourself in the jobs that you’ve had.

And if you can’t seem to approach career storytelling with ease for a particular job once you have the process down, then there’s something here isn’t there? Something that needs to be looked at. Preferably with help and gently. And that’s okay.

This is when it’s a good time to contact someone in a profession who can help you because now you know what you’re struggling to talk about. Or you can visit with a really good friend who is willing to help you honor the experience that you’re struggling to make sense of.

Whether we want to admit it or not (or can admit it or not), the jobs we’ve had are as significant as our romantic relationships. And often when you think you’ve walked away unscathed, that’s a sign of how much you’ve disassociated from your pain. Numbness doesn’t make you unscathed. Part of you thinks, “what’s one more dissapointment?” Well. Lots actually. Until you start to emotionally digest your experiences so that you can change something about how you’re experiencing your life.

True, you might be thrilled to move on physically from a job, but experiences do stay with us and ask to be processed at the first sign of perceived safety.

Most of the time what happens is that your resistance or pain from past work experience shows up right when you need to work on your resume. And instead of realizing that there is something that wants resolving from within, you take what you’re experiencing to mean that you hate or can’t write your resume successfully.

Grieving is a very real part of joining and leaving the work families that we do. And this career storytelling process will certainly help you learn how to let go in the cleanest and most reverent way possible. Otherwise, it’s all too human to try to correct the past without knowing it wherever we go.

So, if you notice that anything unresolved comes up, it just makes sense to recognize it for what it is, rather than trying to push or do away with what is seeking recognition and healing.

I wanted there to be some understanding for the existence of a grieving process in the context of resume writing because it’s part of the deal of being human. We think that grief can’t or shouldn’t show up in certain places, or at certain times, and work tends to be the place where we have the least amount of understanding for grief. If I didn’t address this in preparation for what you’re about to do, your inclination, when you potentially come upon grief, would be to abandon the process (and hence abandon yourself). And you’ll think (again) that creating content as your real self is totally impossible.

Throughout this resume renovation process, you’re going to need to remember why you went to the trouble of starting to renovate your resume in the first place: Namely that its results weren’t making you happy and that you didn’t have the clarity on yourself that you would like. Go slow if you want, but always keep moving.

The career storytelling part begins:

There are several techniques to help you learn how to career story tell. I don’t make the assumption, nor should you, that you ought to know how to tell your stories just because you’ve lived through your life. Storytelling is a skill that comes from paying attention to what you draw your and other people’s attention to.

It also helps you to see where your attention is drawn so that you can understand how your existing career storytelling abilities are motivated. Meaning you’d be amazed at how much blame we each carry around either toward ourselves or others that make career storytelling something we’d rather avoid. And then we wonder why we end up with resumes that make us go WTF.

Career storytelling is a practice of self-awareness.

I used to begin this process by asking people to tell me about what they did at work, but the “storytelling” quickly deteriorated. So don’t do that.

Then I started asking people about why they chose a particular job, line of work, or employer, and it quickly became apparent that no one knew what had guided them to where they were with any reliability. So don’t do that either.

The “in” into the storytelling really matters.

With some experimenting, I determined that it was best to start with leading questions and “starters” or “prompts.” For yourself, it may take a couple of tries to determine which combination is best for you – it could be a bit of this or a bit of that or all of this and none of that.

Here are the instructions + some considerations as you lead into your own career storytelling:

Step 1: To begin, look at your resume and pick one job to start with. Put the job title, the timeframe you worked there, the company you worked for, and location at the top of the page.

Next consider what will help you write more rather than writing less:

As a personal preference, it seems to work well if I start with prompts and then questions that help to fill in any missing details.

To help you write more rather than less right now, write conversationally (you’ll translate things to bullets as a last step later). You want to be as detailed as you can be at this stage.

Don’t worry about what you were hired to do (the job title) vs. what you end up writing here. And don’t try to make yourself into a box or to fit into a box. We’re researching you – not the job.

Step 2: With a single job in mind, complete the following prompts (and make up some of your own if you’d like):

Consider with the writing prompts:

You don’t need a different example for each sentence starter (there’s no need to and it’s just more work UNLESS you want to and UNLESS that’s what feels right). Trust the “one” example that comes to you and develop the detail by bringing all the fuzzy memories into crystal clear focus.

The prompts:

One day at work that I really enjoyed was …


The thing I was most proud of in this job was …


I’ll never forget this one (good, fun, engaging) time that …


The best day in this job was the time …


My boss thanked me for …


My colleague thanked me for …

If no one was there to do this job (what would happen if this function wasn’t performed) …

Step 3: Next, conversationally answer any or all of the following questions still with the same job in mind. Imagine, for example, that you and I decided to meet at a quiet coffee shop and we’re sitting in two comfy chairs in the corner. Tell me in as much detail as you can:

What did you like or enjoy most about this job? What happened as a result of this?

What was your favorite thing to do in this role? What happened as a result of this?

What did you take charge or ownership of effortlessly and/or joyfully?

What one task, project or day in that job stands out for you? Why is this meaningful to you personally? And why is this important to others? What happened as a result of this?

What did people thank you for in this job? What did you like being appreciated for in this job? What did someone specifically say? And what did you take that to mean exactly?

Who did your work matter to? Who needed your results? Service? Time? Attention? And why?

What did you like about particular people in this example that you served in your work?

Remember: What you’ve written down will look, read, or feel like an organized or messy tornado of sentences, quotes, facts, details, feelings. It’s perfect.

Step 4:

Skim over what you’ve written and imagine that for each answer I’ve asked you:

a) Is there anything else about that?
b) Is there more here?
c) Can you tell me anything else to help me understand the context you worked in or what you were doing?

Consider: These three little questions are really important because you don’t realize how much of your context (the conditions) of your work you take for granted. As an example:

I once worked with someone who’s resume made it sound like she worked in an office but in reality, she was doing administrative work in or very near to active combat zones.

When she wrote “organizing classrooms” it actually meant that she was sending shipping containers to be used as classrooms near still active and recovering war zones. She also mapped routes to keep teachers safe from gun or bomb attacks on their way to those classrooms.

If a prospective employer asks her if she can handle stress I’d say she has that covered, but it’s her context that shows that without her needing to reiterate that in any way. But it would have been difficult for anyone to deduce that without the context of her job in the career storytelling part. So details, details, details about your context! Don’t take your environment for granted.

Step 5: Now go back to what you’ve written and try to quote quantities where you can that you might have overlooked (e.g. volume, the number of people, what $ you were responsible for, who specifically said what). Doing this helps you discern a few things:

a) A truer picture of your capacity,
b) Whether you liked working at that capacity or not; and
c) What capacities you would like to work with in the future so that you can include or exclude this detail as appropriate.

One of the things that makes career storytelling in person or in resume bullets compelling is numbers and quantities. This is because these specifics lend to the credibility of who you are without the need to be “fluffy” in your resume or without fearing that you should “fluff up” your content. Specifically think about:

:: Quantities of anything that you cared for (people, paper, reports, grants, profit, guests, etc.)

:: Quantities of anything you saved (money, time, heartache, headache, fees, lives, etc.)

You might think this is hard if you didn’t have access to the exact budget and/or the specifics have faded from holding the job over a decade ago. But I know that you remember more than you think you do and that you can truthfully present something.

As an example, when I worked with Tracey on her resume she told me about how a charitable healthcare organization brought her on board to do “office stuff” for them.

Once she was settled in the job, she learned that they did mail campaigns once a year. The campaigns cost $20,000 to outsource and garnered about $70,000 in donations. What the company didn’t know when they hired Tracey was that she knew a little bit of graphic design and it was something that she wanted to learn more about.

When she saw what was mailed out, she thought for sure that she could do a better job than that and asked her boss if she could try. Her boss said, “Okay, design something.”

Well, her boss was very happy with the results and Tracey ended up bringing the design and mail out production in-house. She knew what her time cost, she knew how long it took her to design the mail out campaign; she knew what the postage cost, she knew what it cost to get the printing done. The total was close to $9,000.

She knew that they still got $70,000 whether they spent $20K or $9K on the mail out. And she knew that that any savings went directly to the services they could offer. Should could confidently say that she saved the company $9,000 for each of the five years she worked there, which is $45,000.

I “walked” her through the numbers that she knew in order for her to be able to write something that she could proudly and confidently stand behind even if it was conservative.

You can do this too.

This is all the raw data you need to create your bullets.

Step 6: Do Steps 1 – 5 for each job on your resume.

Look at you! You’re career storytelling!

Articles that are upcoming in the Resume Project:

– How to write resume content when you haven’t been “in the workforce” for a while; and

– The process of (nicely) extracting bullets from career storytelling.

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