Changing career directions doesn’t mean starting from scratch

The Jump #6

Welcome to The Jump: a monthly newsletter for Millennials shifting career directions. When I was shifting career directions myself, I started this newsletter with one question in mind: what is the relationship between career change and personal growth? 

As you’re a reader of The Jump, you want to crush it in your next opportunity. To crush it, you need skills.

Perhaps you’re a software engineer, but feel like there’s not much value in the features you’re building because they aren’t solving an unaddressed strategic problem with the product. You have ideas for how to address it and want to shift into a Product Management role.

Or perhaps you’re an expert at SEO, but you’re tired of implementing strategies you disagree with. You want to shift into a marketing strategy role so you can help shape its direction.

Or perhaps you’re a brand strategist, but enjoy cooking and want to explore how you can do more of it in your career.

As a transitioner, you have some idea of what you want to do next. And you know you need to gain skills to get there. However, because you’ve invested the last three to five years getting a degree or the last one to three years in a specialized role, you don’t want to feel like your hard-earned skills would be used in your next opportunity.

By working towards a new opportunity, are you abandoning the skills you worked so hard to gain?

The problem with “what do you want to be when you grow up?”

Growing up, we’re told to choose one field to devote our entire career to.

“What do you want to be when you grow up?” is what we were asked when we were young. 

“What major are you choosing?” is what we were asked when we were applying to colleges.

“What do you want to do?” is what we’re asked currently.

These questions are reinforced by the idea that we must decide on one thing. One job. One major. One company. 

The problem is that deciding on one thing prevents us from developing our ability to adapt. One survey by the US Bureau of Statistics shared that Baby Boomers have switched jobs an average of twelve times in their lifetime. And this trend remains the same with us Millennials: we switch jobs roughly every three years. If we stuck to one path long-term, we prevent ourselves from becoming adaptive. And when job-switching is as frequent as every three years, it’s more valuable for us to adapt than it is to be certain. We shouldn’t shy away from change—we should welcome it.

What skills would allow me to do needed and fulfilling work?

Though “what do I want to be when I grow up?” isn’t helpful, the intent behind it is. This is the larger question behind it is “what skills would allow me to do needed and fulfilling work?” 

The former is a terrible question because it prescribes an approach that won’t accomplish the outcome it wants (needed and fulfilling work). The latter is a helpful question because it frames the outcome we want and acknowledges our freedom to decide how we accomplish that outcome. 

Scott Adams, the creator of Dilbert, talks about two ways to accomplish a valuable and fulfilling career:

  1. Become the best at one specific thing.

  2. Become very good (top 25%) at two or more things.

He then shares the downsides of the first approach:

“The first strategy is difficult to the point of near impossibility. Few people will ever play in the NBA or make a platinum album. I don’t recommend anyone even try.

The second strategy is fairly easy. Everyone has at least a few areas in which they could be in the top 25% with some effort. 

In my case, I can draw better than most people, but I’m hardly an artist. And I’m not any funnier than the average standup comedian who never makes it big, but I’m funnier than most people. The magic is that few people can draw well and write jokes. It’s the combination of the two that makes what I do so rare. And when you add in my business background, suddenly I had a topic that few cartoonists could hope to understand without living it.”

Both approaches will lead us to a valuable career. It’s just that the second approach—the approach that’s less talked about—is way more practical.

Career changers have a head start at doing valuable work

When it comes to changing career directions, there are a few cases I can think of where approach #1 would be more practical. Approach #1 may be the better approach if you want to go into E-sports.

But for the career changer not going into E-sports, it’ll take less time for us to make the jump if we focused on being very good at ≥2 skills than being the best at one. 

Think about it. We already have skills cultivated from our previous experience, and there’s a high chance we may be decently good at two skills. This means we have a head start at doing work that is rare and valuable, making us a unique fit for our next opportunity. If you’re the software engineer who wants to go into Product Management, you combine your technical understanding with your product instincts, making you a technically-savvy PM. If you’re the marketing strategist interested in cooking, you can combine your marketing skills with your passion for cooking to host private dinners in your apartment.

As you already have experience, you may already be the top 25% at two (or three) skills. This means your only step is to bring to light skill combinations that will aid you in your shift. And if you aren’t in the top quadrant of two skills, you can be with some effort.

Career changes can feel like you’re starting over. But given the skills you already have, you’re actually 70% there. All you have to do is uncover a combination of skills that is unique, interesting, and valuable.

Credits to Ariana Bautista for feedback on earlier versions of this writing.

How to progress when your career path isn’t linear

The Jump #5

Welcome to The Jump: a bi-monthly newsletter for Millenials in the midst of a career transition. The genesis of this newsletter began with a question I had when I was in between jobs: what is the relationship between career change and personal growth?

This issue’s tl;dr:

Your career path will most likely be nonlinear. Nonlinear career paths mean that your progression looks more like mastering your craft and less like climbing the corporate ladder. Let’s recognize this and be less hard on ourselves.

To stay motivated, people need to feel a sense of progress. And because career paths today rarely look like climbing the corporate ladder, we need to be proactive about visualizing our own progress. 

Career progression was easy to conceptualize twenty years ago. You start your first job after graduating from college. You work hard to get a promotion, receiving an increase in salary and “senior” in your title as a result. Your next promotion gives you people to “manage”, a nice P&L, and another increase in salary. Eventually, you earn a spot in the C-suite.

Progression in the old world of work is tangible: more pay, more people under you, the corner office, more budget, sexier title. 

In today’s world of work, progression is less tangible. Smaller companies don’t have a corporate ladder (if they do, it probably should be a red flag to you). And if you work in a large company, you’re likely going to leave in three years. Three years isn’t enough time to reap the tangible outputs of progression.

In conversations I have with my peers* about career goals, I hear two statements consistently:

  1. “I have no idea what I want to do with my life.”

  2. “What do you want to do?”

*this doesn’t include business owners. You all are an unrivaled breed—unconcerned with silly millennial existential crises due to the necessary focus required of you to run a solid business.

This has never made sense to me. We don’t have ten-year plans ourselves, yet we ask our peers what theirs are.

The good news is, no one needs a ten-year plan. 

A friend and mentor of mine, Jordan Husney, once told me something wise that I’m about to paraphrase because my poor memory can’t remember it word for word:

“Instead of a clear ten-year plan, I’d rather be more clear on my purpose and immediate next step and less clear on what my ten-year plan looks like.”

Jordan’s point stuck with me. Unless you’re an aspiring doctor, lawyer, or professor, it’s more practical to be certain of your purpose and next step than to have a certain ten-year plan. Just how we see the danger of a long-term plan for companies, we’re seeing how dangerous a long-term plan is for our own career paths. Believing our plans lead us to fulfillment, they leave us unfulfilled, wondering what to do next.

How do I know if I’m progressing?

A nonlinear career path leaves us a big question: How do I know I’m progressing?

I made the point earlier that people need to feel progress to remain motivated about what they’re doing. So it’s worth answering this question.

I think there are three ways to think about this:

  1. Skills & mastery (getting better at your craft is progress)

  2. Portfolio & outcomes of your work (the work you produce is progress)

  3. Teaching & mentoring (the people who learn from you is progress)

Each point deserves its own newsletter rather than a few hand-wavey paragraphs. For the purposes of (hopefully) giving the point what it deserves, we’ll focus this issue on skills & mastery.

Skills & mastery

To understand mastery, let’s look at two personas: the artisan and the athlete.

The Artisan

The artisan is the shoemaker, the blacksmith, and the chef. The artisan’s work is a craft. The artisan’s main priority is to create something beautiful, delicious, or inspiring. The artisan is not satisfied if their work isn’t beautiful, delicious, or inspiring.

To the artisan, progress is making something even more beautiful, delicious, or inspiring than their previous thing made. 

If we think about career progression in the way an artisan thinks about mastery, I think we’ll benefit. What makes an artisan fulfilled is the craft itself, rather than the number of people who work for them or what their salary is.

The Athlete

The athlete is the person who wakes up in their running clothes and runs along the river just as the sun rises. The person who’s first to be on the court and the last to leave.

The athlete aims to improve the breadth and depth of their skills. How do I improve my three-point percentage? How can I increase the number of miles I’m able to run?

The athlete is obsessed with deliberate practice. The only thing they think about after winning a game is when the next practice is. The practice schedule is constricting to the casual exerciser but freeing to the athlete.

Athletes teach us that today’s career progression can be more about how we improve our craft.

Today’s career progression is mastery

The beautiful irony is that the future of career progression can be found in an age-old idea: mastery. Pursuing excellence in our craft and finding fulfillment in the pursuit itself.

Millennials, don’t be hard on yourself if you feel like your progression is stalled.

You have a craft. Improve your craft and witness the progress you’ll make.

More reads on mastery and work

ShuHaRi | Martin Fowler

ShuHaRi is the most simple way of thinking about learning a technique. Here’s the idea:

  • Shu = follow the teaching

  • Ha = branch from the teaching

  • Ri = innovate the teaching

Simple and applicable.

The Strategist’s maturity matrix | Clay Parker Jones

I decided to re-read Clay’s piece after starting my new job at Sanctuary. It’s a great take on what the progression of a Strategist looks like. I’m sure I’ll be revisiting this when we think more deeply about the kind of development we hope to see from Product Strategists at our company.

Product Management Skills self-assessment | Whitmaan

More skills matrices, yay! As statistician George Box would say, “All models are false, but some are useful.” If you’re a fellow product person, hold back your instinct to poke holes in this framework and try this yourself. I found it helpful.

Spidey-sense | Rands in Repose

“Spidey-sense is a feeling. You might be hesitant to heed it because you can’t tell where it came from. You might attempt to ignore it because the difference between a feeling inspired by hard-earned wisdom and one inspired by an irrational emotion feel the same. They aren’t, but the only way you’re going to learn the difference is by first listening then acting.”

The Working Pair | Rachel Yaeger

Six couples. All New Yorkers. All knowledge workers. The Working Pair might be inspiring any of you who a) are in a relationship and/or b) worry that being in a relationship somehow holds you back from pursuing your career. Beautiful site, even more beautiful stories.

In transition with you,


We’ll be wrong about what makes us happy

The Jump #4

Welcome to The Jump, a newsletter for millennials in the midst of a career transition. 

As I was in the midst of my own career switch, the idea of this newsletter started with a question I couldn’t get out of my head:

What’s the relationship between career change and personal growth?

I found out about a book called Working Identity by Herminia Ibarra and read it to help me answer this question. I heard about Working Identity from a Bill Simmons podcast with David Epstein (sidebar: David’s Range is also a book I've been meaning to read).

First off, I do consume content that isn’t career/work/org/psychology/product-related, contrary to what many of you work nerds think. It’s usually NBA analysis though, so I’m not as cultured as I sound. As I indulged in my regular reading of non-work-related stuff (which is only NBA analysis), I stumbled on a gem that ultimately inspired a work-related newsletter. 

My struggle to expand my taste in content beyond work/product/psychology is beside the point.

Ibarra’s thesis is this: 

To bring your ideal next career move into reality, we must test & learn possibilities, rather than predict what might make us happy and execute against that prediction. 

As I was in the midst of my own transition, Working Identity deeply resonated with me for two reasons:

  1. Testing & learning transforms organizations. As someone who’s spent the last three years helping organizations test-and-learn, I’ve seen this approach unlock more meaningful change than creating a 100-page deck that outlines a grand change plan.

  2. Testing & learning defines my career trajectory:

    • I tested the idea of studying computer engineering and learned that I wanted to study how people can thrive. After nearly failing my Java class in the summer of 2013, I wanted to try something different. I always enjoyed reading about how to build better habits and was curious about what that would look like professionally. So I switched my major to psychology.

    • I tested the idea of grad school and learned that I wanted to be a practitioner. My plan was to pursue a PhD in Org Psychology, so I led a research lab and published an academic paper (PhD programs love applicants who’ve published). At the same time, I was freelance writing for a consultancy and wondered the possibilities of working full-time for them. With a lot of luck, I started working for them.

    • I tested the idea of building my people and process skills and learned that I wanted to gain more skills in product. I loved the opportunity to work on process- and people-related problems. And, I found out myself itching to work on product-related problems. Thus, my recent endeavor as a Product Strategist at Sanctuary Computer began two weeks ago.

I lied. Ibarra’s book resonated with me for two reasons and three longwinded sub-reasons.

It’s worth noting that Working Identity is written for the mid-career-changer. Think the 38-year-old financial services leader who’s curious about cryptocurrency, but doesn’t know how to build a career around that. Or the 45-year-old schoolteacher who wants to start their own organizational behavior practice but worries about losing financial stability. I felt Ibarra’s insights applied to me as equally as it did to her target audience.

Hence, the genesis of The Jump.

Needless to say, I want to acknowledge how much harder it must be to go through a career change later than earlier in our career. The Jump readers are in a much more fortunate position than Working Identity readers.

But again, the insights from this book also apply to the early career millennial.

Here’s five.

“There are two types of people. Some are always jumping. Some never jump—they settle down too easily and get stuck.” (1/5)

True. Settling down is comfy, tho. And the more settled down you are, the harder it is to make The Jump. This is why we need explicit strategies to help us do so. 

“Almost no one gets change right on the first try. Forget about moving in a straight line.” (2/5)

Amen. Building a meaningful career is less a linear process than it was before. We’re overdue to outgrow this mental model.

“Becoming our own person, breaking free from our ‘ought selves’—the identity molded by important people in our lives—is at the heart of the transition process.” (3/5)

This. So much this. Two things I want to unpack here.

  1. Change is letting go of what we ought to be in service of becoming who we want to become. As I’m new to the product/tech world, I’ve been slowly letting go of my “ought” org design self in service of being a better product strategist.

  2. This “ought self” is likely influenced by people important to us: our spouse, family, and friends. Maybe your parents wanted you to be an engineer, so 18-year-old you decided it as your destiny. When you feel stuck and ask your parents for advice, they’ll likely say, “Well, your experience is in mechanical engineering, so look for mechanical engineering positions.”

Which is a good segue:

“Reason and consistency—what Susan Fontaine, the M.B.A. who jumped from one corporate job to another, called the ‘relentless logic of a post-M.B.A. CV’—keep people from thinking outside the box.” (4/5)

Being “completely logical” rarely serves The Jump. Logic tells us to work in a role or at a company that would impress our parents’ friends. In addition to your reasoning, your instincts are also a source of information. Remain attentive to your instincts.

“We learn who we are—in practice, not in theory—by testing reality, not by looking inside. We discover the true possibilities by doing—trying out new activities, reaching out to new groups, finding new role models, and reworking our story as we tell it to those around us.” (5/5)

If there’s any quote that you take away from this slightly strange edition of The Jump, it’s this one.

Introspecting our way into our dream career won’t work because we’re terrible at predicting what makes us happy. Psychologist Dan Gilbert talks about this idea of affective forecasting: we predict how we feel once we reach a future state, and we’re often wrong about our predictions. Anyone who says “I want to be a lawyer/doctor/engineer when I grow up” is making an affective forecast.

Don’t get it twisted, I’m all for hypothesizing a career we think would make us happy. What I’m not for is treating this hypothesis as an absolute truth and/or a static plan.

It’s best to assume we’ll be wrong about what will make us happy. To truly make The Jump, we must disprove our views that stem from our “ought self” as quickly as possible.

Work with people in spaces you think you’re interested in and see if you want to keep working in that space. Start coaching others for free and see if you want to keep coaching. Build software and see if you want to keep developing.

Let’s stop assuming our career plans are 100% infallible. Let’s test what we assume may be a career move that makes us more fulfilled.

If we do this, we’ll be much happier.

At least, according to Ibarra, my working identity assumes so.

Your next big break will happen through luck, not hard work.

Why network effects matter more than you think

As an NYC resident of over three years, I’ve learned that NYC is simultaneously a big and small world.

It’s a big world because there are so many goddamn people. All trying to be happy, all having a purpose, all giving and receiving help. The sheer population can feel overwhelming. On top of this, you have tons of buildings, restaurants, streets, avenues, pigeons, retro Jordan variants, dogs, and dog poop. 

New York is also, almost eerily, a small world. Having graduated from a UC college (UC Irvine to be specific—zot zot), many of my friends also went to a UC. Folks at the company I just accepted an offer at have been following the thought leadership of my previous company. Even the bboys (breakdancers) I meet in NYC know the California bboys I know (I used to bboy competitively in California). Every time they see me, they chant “West Coast!”

Everyone seems to know each other. It’s fucking weird.

But for our purposes, it’s helpful.

On Fast Flow

I like this piece on luck and paid opportunities by Jocelyn K. Glei. She cites a book written in the ’70s by Max Guntherm called How to Get Lucky. I’ve yet to read it, but there were two snippets she mentioned that stuck with me.

The first snippet was about Lauren Bacall, an award-winning female actress who debuted her first film in 1944. The second snippet is about luck and dating.

Here’s the first snippet:

The commandment of the Second Technique is: Go where events flow fastest. Surround yourself with a churning mass of people and things happening.

[Bacall’s] first couple of years in New York were attended by almost continuous bad luck, according to her autobiography, “By Myself.” She got bit parts in plays that promptly folded, landed modeling jobs that turned out badly for random reasons. [But] she did not permit her string of bad luck to discourage her. Instead of becoming depressed and inactive – which bad luck can do to people when they believe it is caused by their own flaws – she kept herself oriented to the fast flow. [Bacall] got busily, almost frantically involved in war-effort work such as the Stage Door Canteen; in part-time jobs such as ushering at theaters; in social events, dates, parties, and picnics. She made herself the center of a howling whirlwind of people.

As you’re a reader of The Jump, Lauren Bacall’s “always forward, never backward” mentality should sound familiar to you.

Gunther continues:

She could not know which of those people would be the conduit through which her break would flow. As it turned out, that destiny-marked person was an obscure English writer named Timothy Brooke... One night they went to a nightclub named Tony’s. While there, Brooke introduced her to a casual acquaintance of his, a man named Nicolas de Gunzburg. She did not know it at the time, but this was the first link of a long chain of circumstances leading to her big break.

De Gunzburg was an editor of Harper’s Bazaar. Through him, the lucky young actress got to know Diana Vreeland, the magazine’s fashion editor. Vreeland gave her some modeling assignments. One arresting full-page shot caught the attention of a Hollywood producer, Howard Hawks. Lauren Bacall’s movie career was launched.

She was a woman of great grace, beauty, and talent. Those attributes played a necessary part in her climb. She had to have them so that she could take advantage of the big break when it came. But she also had to have the break itself. If she had not gone out of her way to find the fast flow, and if she had not met that obscure British writer as a result, the name Lauren Bacall would mean nothing to us today.

Lauren Bacall didn’t sulk in rejection. She kept moving. She optimized for the number of meaningful interactions she’d have until she met the right person that led to her big break.

If I were to reflect on who that person was for me, it’s my friend Sam Spurlin. During my time at UC Irvine, I grew very interested in building a career in making work better. As I read articles about this problem space, I stumbled on an article of his on 99u. I read the author bio and realized Sam was doing work I wanted to be doing in my own career (consulting, coaching, writing) in a problem space I wanted to focus on (making work better). I emailed Sam to chat and he graciously accepted. Fast forward a year or so when The Ready started, he offered me a gig to write for The Ready. My first two articles seemed to resonate with The Ready’s readers. Psyched about this traction, I asked Aaron (the founder) about full-time opportunities. To my fortune, he gave me a shot, and I moved to New York in June of 2016 to start my dream job. 

It’s also worth mentioning that this job opportunity also enabled me to live in the same city as my partner—she moved to NY from California before I did. To this day, we live together in (still) NYC.

That reminds me. Speaking of dating, here’s the second snippet I liked that Jocelyn cited:

Let’s suppose you are bored, lonesome, stagnating and in need of a life-changing love affair to get your engine tuned up again. You have a weak link with a man named A, a fellow member of a local political action group. One night A’s friend B, whom you don’t know gives a party. A, discovering that you are at loose ends that night, asks B if it’s all right to bring you along. B says sure, as long as you contribute a bottle. Another guest is B’s friend C, known to neither you nor A. This C, a tertiary link in your network, is the life-changing person you have been waiting for.

That is how luck happens.

Of course, this book was written before dating apps existed, but you get my point.

There is no such thing as a self-made person

kobe bryant basketball GIF

When I was younger and more naive, I thought that the secret to success was hard work. My belief was largely influenced by three things: 

  1. Kobe Bryant’s obsession with working hard (I grew up a Lakers fan).

  2. My wonderful, hardworking parents’ immigrant mentality of hard work being key to success.

  3. My education—I grew very comfortable doing homework and studying alone.

I’ve since learned that hard work is just part of the equation. What matters more is what you work on and who you work with.

I’ve fallen prey to thinking my successes are largely due to my grit, skills, and perseverance. I’d guess you’ve done this too. It’s easiest to observe how we made an outcome happen rather than how others (and/or the broader context) made it happen. And, it feels good to give ourselves the credit for the result.

I hate to break it to you, but successes don’t happen because of you (or me). We are a small piece in the success equation. 

Successes happen because of a million different factors. The introduction your friend offered. The chance your previous employer took on you. The coaching your colleagues and friends offered you. The compassion your romantic partner gives you after a stressful day. The client context. How well your future employer is doing financially. Needs that exist. And of course, the person attached to your next big break.

Jocelyn began her piece with this quote from Ben Casnocha:

“Every opportunity is attached to a person. Opportunities do not float like clouds in the sky. They’re attached to people. If you’re looking for an opportunity — including one that has a financial payoff — you’re really looking for a person.”

If you’re looking for an opportunity—including one that has a financial payoff—you’re looking for a person.

Not a posting of the perfect job. Not validation from others. Not the world rewarding you for all the hard work you’ve put into your job search.

A person.

So stop thinking you can do this alone. And start putting yourself in fast flow.

I started The Jump with the intent to share something with you weekly. So far, it’s been biweekly. I’m bummed I haven’t been able to meet my initial goal of publishing weekly as I’ve chosen to prioritize client work and time with friends and loved ones.

Because I start my new full-time job with Sanctuary Computer on 8/12 (which I’m stoked about), I imagine I won’t be able to ramp up the cadence to weekly. Thus, I’m going to adjust our cadence from weekly to biweekly. This means that you’ll receive a new post every other Wednesday morning. I want to be real with how much time and focus I need to give you something that’s (hopefully) valuable, fresh, and authentic. 

Thank you for understanding. I appreciate your support of The Jump thus far!

Authenticity will land your dream job

If you can’t be your authentic self, it’s not a fit

I’m going to tell you about a time I was rejected from a job I didn’t actually want.

A connection of mine DM’d me on LinkedIn. She asked me if I was interested in an org development role at a large multinational food service conglomerate. To be honest, I wasn’t super stoked about the company, but I figured it wouldn’t hurt to interview. 

I responded to her generous DM:

“I’d love to learn more about the role. Thank you for reaching out!”

My first interview was an initial call with a recruiter. It went well—they decided to move me forward in the process. Two weeks later, I had a call with the hiring manager (let’s call him Shawn). This also went well, and I was moving onto the next stage: the onsite interview. “I’ll have a coordinator email you dates and times that work for us.”

After two weeks of silence, I followed up with them. They finally scheduled me for an onsite. I’d be talking to five people in back-to-back interviews.

My first interviewer was with Shawn, again. He was smart but rambled a ton about their org’s problems. He asked a total of three questions, using most of our time opining on the “Galbriath Star Model,” the role itself, and the company’s culture. I’m all for interviewers being informal and conversational, but our conversation lasted for ninety minutes: forty-five minutes longer than it should’ve. Hello, meeting domino effect.

It turns out interviews starting forty five minutes late wasn’t a bother to my second interviewer. She opened our interview with, “So, did Shawn go on one of his long-winded rants?” Followed up with, “Why would you leave a super exciting space to work in a traditional company?” Yikes. I remember asking what they enjoyed most about working there because this person didn’t mention anything positive at all about the company.

The third interviewer opened up about how the company is a bureaucratic nightmare and how a lot of their younger employees have left the company. He even pulled the ultimate statement any interviewer pulls out to stroke a candidate’s ego:

“We could use help from someone with your background.”

I grew more hesitant about this opportunity, but I remained enthusiastic and still put my best foot forward. Why not see where it might lead?

After five intense back-to-back interviews, I reflected on how I felt about it all. I felt good about how I represented myself, but wasn’t sold on the opportunity at all.

Regardless, I sent all five interviewers a follow-up email the day after thanking them for their time. I didn’t hear back for two weeks, so I sent an email to the recruiter and hiring manager to follow up. A week later, the recruiter left me a voicemail:

“We decided to move forward with another candidate. We wish you the best of luck with your search.”

I asked for feedback. Never heard back.

I had two choices here: 

  1. Sulk in the sting of rejection.

  2. Not feel bad, because I was content with how I represented myself to them.

I chose the latter.

Authenticity is a filter

If you’re early in your career like me, you might be familiar with this piece of career advice:

“Tailor yourself to the job you’re applying for.”

While I found this advice helpful in the beginning, I learned it’s shortsighted. I realized it’s less about tailoring yourself to the job and more about highlighting aspects of your authentic self that would show up in the role:

If there isn’t any commonality between your authentic self and the individual they want, it’s simply not a fit. For both you and them. In our earlier example, I believe I put forth my authentic self and still found it wasn’t a fit.

Despite it ending up in a rejection, I considered the experience a win: I know now that I don’t want to work at that company. And I had a low-stakes opportunity to practice an onsite day, which prepared me for future onsites I had.

Lastly, putting out an inauthentic self is not just fair for the employer—it’s not fair to you too.

If I signed an offer with them, I’d likely find the job unsatisfying. And they’ll likely find that they hired someone they didn’t want.

Authenticity escapes you from competition

I’ve been obsessed with a podcast that Naval puts out called, well, Naval. You know you’ve made it when the name of your podcast is your name.

There’s a great bit in Escape Competition Through Authenticity that relates to this situation:

“Sometimes you just get trapped in the wrong game because you’re competing. Competition is not just stressful and nerve-racking, but it often drives you to the wrong answer.

The best way to escape competition is just to be authentic to yourself.

If you are fundamentally building and marketing something that is just an extension of who you are, no one can compete with you on that. If you are competing with Joe Rogan or Scott Adams, it’s impossible.”

Though Naval is talking about entrepreneurship, I think this principle applies to job searching too. If you’re authentic, you eventually escape competing with others, and the right opportunity finds its way to you.

Find (or create) work where you can be your authentic self

The goal isn’t just to find a job.

The goal is to find a job where you feel like your guard won’t be up.

If your guard is up, you’ll be exhausted protecting your image for half of your waking life. From Robert Kegan and Lisa Lahey’s An Everyone Culture:

“In an ordinary organization, most people are doing a second job no one is paying them for... Most people are spending time and energy covering up their weaknesses, managing other people’s impressions of them, showing themselves to their best advantage, playing politics, hiding their inadequacies, hiding their uncertainties, hiding their limitations.”

The goal is to find a job where you can truly be your authentic self.

A job where who you are is aligned with what you do, knowing that your authentic self is constantly changing, growing, and evolving.

I’m beyond thrilled that you’re one of the 400 subscribers reading this. Thank you to the folks at Creative Mornings for sharing my introductory article in their weekly newsletter. If you haven’t checked out Creative Mornings, you totally should.

Thank you to Ariana Bautista for your editing suggestions on this piece!

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