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!

It all starts with one email

The Jump #1

% of applications sent that led to first interviews

This is the number I keep track of regularly.

My old strategy for getting the first interview was to create and send a pre-interview project. Here’s the idea behind a pre-interview project: share a piece of work (a piece, deck, or video) that shows the value I could bring to their team.

Before I started at my first full-time job, I’d use the pre-interview project for all two companies I applied for:

# of pre-interview projects sent = 2
# of interviews scheduled = 2
% of projects that led to interviews = 100

Small sample size notwithstanding, my Asian American self was satisfied with a perfect 100. I was invincible. The strategy worked.

Now, I’m reminded that it doesn’t always work.

Referrals vs. Pre-Interview Projects

I sent about four pre-interview projects during the first three weeks of my current search. Here are the stats:

4 pre-interview projects sent to hiring manager
22.5 hours spent making pre-interview projects
2 interviews scheduled as a result

Not every pre-interview project was leading to an interview. And I spent a gruesome 22.5 hours (!!!) on them. 

However, in tandem with my pre-interview projects, I was getting referred to roles. The results were better:

10 roles referred to  

2 of roles with existing relationship with the decision-maker
11 interviews scheduled from referral/pre-existing relationship 
17 total hours spent generating the referral (coffees, calls, emails)

Referrals generated more first interviews for me than pre-interview projects and took less time. 

Referrals are a win-win-win

Referrals produce three wins:

Win #1: The candidate will have more of a chance of receiving a job offer. This is the most obvious win. We all know how ineffective it is to blast your resume out to every opportunity and hope for a response.

Win #2: The referrer gains more trust and, in some cases, pay. The organization sees this person as someone who could bring in other smart people. My friend at LinkedIn literally receives a referral bonus if I sign an offer there.

Win #3: The organization doesn’t need to spend more time and money to find an exceptional candidate. Its costs money and time for organizations to hire a candidate, sometimes ranging in the thousands.

Everyone wins from a referral.

The downside of referrals

However, referrals don’t increase diversity.

The company gets more people who are just like those already in it. This is a problem. Hiring more of the same inhibits the company from finding people who are culture adds (not culture fits). What’s more, it stagnates the diversity of perspectives, ethnicities, nationalities, and backgrounds of people in the organization.

However, this deserves an entirely different post. And your current need is to get referred, not to help solve this problem (yet).

Three ways to get referred

1. Reach out to the hiring manager for the role you applied for.

This is the most blatant approach. I’ve reached out to plenty of hiring managers just to express interest. Here’s a skeleton of an email I’d send:

Hello [name]!

I’m Tim. I came across your profile as I just discovered [x team/company]. It’s nice to meet you.

I noticed that [company name] is hiring a [role]. I want to express my interest in the opportunity.

To show my interest and value I could bring in the role, I thought I’d share you my [portfolio/pre-interview project]

I’d love to be considered for a first interview for this role.

Thank you for your consideration!

–tim

The cold reach out to the hiring manager can be effective for two reasons:

a) You stand out, for better or for no gain.

b) You increase your chances of a recruiter reaching out to you for a first interview.

Of course, the risk is you wasted your time if they don’t respond.

However, I think reaching out is better than doing nothing. For example, I sent a pre-interview project to Spotify for their Agile Coach role. An agile coach at Spotify I met with mentioned an effective agile coach helps teams be more effective at framing problems. So I made this toolkit. My goal was to share with them a piece of work I’d do as an agile coach. 

When I sent it to the hiring manager, they said they couldn’t use the information to influence the process as they were committed to fairness and objectivity in the process. The I/O Psychology nerd in me completely understood this, this levels the playing field for everyone else applying. I concluded that it was worth a shot.

A month later, I received an email from a recruiter to interview for the role. Though ultimately I didn’t receive an offer (I was second to their first choice), I was fortunate to go through the entire interview process, meet smart people, and get a glimpse into one of my dream companies.

2. Reach out to people who’s work is aligned with what you want to be doing.

Take the time to discover folks on Twitter, Medium, or LinkedIn who’s career seems aligned with what you want your next opportunity to be. This is how I got my previous job at The Ready.

Hi [name],

I’m Tim, an organizational change practitioner based in NYC. I came across your name as I was looking into product people in the Enterprise SaaS based in NYC.

I’m reaching out because I’m currently exploring product management as a potential next chapter in my career. I noticed that you’ve made the transition into product management and would love to understand what helped you when you made the shift.

Would you be willing to grab 25 minutes this week or next so that I could ask you 5 questions about your experience?

All good if you aren't able to offer up the time.

Hope to hear from you!

–tim

My questions varied conversation to conversation, here are five questions I default to:

1) What led you to your current role?

2) What does your day-to-day look like?

3) What did you wish you knew before applying to PM roles and starting your first PM job?

4) If you were me, what would be your next steps in your search?

5) Who else should I talk to?

Don’t be surprised by the amount of no responses you get. And be surprised by those who do respond.

3. Ask your weak ties for help!

If you’re transitioning into a different industry, space, or role, the people close to the opportunity you’re looking for are more likely in the periphery (rather than the center) of your network.

For example: say you were pursuing a career in medicine, but found out you don’t want to go to med school. You find out you enjoy coding, and decide to explore software development. Your anatomy classmates may know tech people, however, your computer science buddies from college or parents’ friends’ daughter who works at LinkedIn are more likely closer to the opportunity you’re hoping for.

Update that LinkedIn headline, look at who you’re following on LinkedIn, Twitter, Medium, and even Instagram, and be surprised by who will reach out. Some will even offer to refer you to a role that’s part of their org or an org of a friend of theirs. Even if you’re just starting out your career, you’ll be surprised by who’s willing to help you.

It only takes one

The tips above aren’t meant to make you a selfish career hopper. They’re tools that you can pull out as you navigate The Jump.

Many recipients of your emails won’t respond. Never take this personally.

Because some will lead to meaningful introductions, reassuring conversations, freelance opportunities, open doors, and a growing support system. Most importantly, your long-term relationships will strengthen, which benefits everyone.

It just starts with one email.

Why I’m starting The Jump

A weekly(ish) newsletter for Millennials in the midst of a career transition

The definition of career success has dramatically changed.

In the old world, our parents stayed in the same job for decades. That job gave them financial security so that they could provide food, shelter, and potentially a college education for you and your siblings. Our parents told us to pick a major in STEM or business so we could land a financially secure job. Once you have a jobby job, you’ve “made it.”

To build a successful career in the old world, we plan-and-execute. First, we need to figure out exactly what we want to do. We figure this out through endless self-reflection, introspection, and arbitrary personality tests. Then, we find a job that matches our knowledge of our personality, quirks, and skills. We make a plan to get that job and execute the plan ruthlessly.

As you figured out, the world has changed. Consider these data points:

  • Companies live shorter. The average lifespan of a company listed in the S&P 500 index of leading US companies has decreased by more than 50 years in the last century, from 67 years in the 1920s to just 15 years today.

  • People switch jobs more often. The average person switches jobs about 12 times in their life. The median amount of time a millennial spends at a job is 3.2 years.

  • Freelancing is more prevalent. 20-30% of the working-age population in the US and EU have done freelance work in some capacity. And one in five full-time freelancers earns >$100k/year.

Ask any millennial about what they want to do long-term and you’ll mostly hear this: 

“I don’t know.”

Test-and-learn

To build a successful career in today’s world, we test-and-learn. We learn about who we are through practice, not theory. We unravel true possibilities by trying new projects, reaching out to people we never thought we’d reach out to, reading about new fields/technologies/trends, and revising our narrative as we tell it to those around us.

Test-and-learn is the backbone of more modern ways of working, such as agile, lean, and design thinking.

Test-and-learn is how organizations succeed in rapidly changing world.

Test-and-learn is how people build fulfilling, wealthy, and joyful careers.

“Sure, you can test and learn. But the foundation of a fulfilling career starts with being clear about the problem you want to solve.”

Here’s the issue: not everyone knows the problem they want to solve. Some do, but most don’t. My friends know me as someone who was clear on what they wanted to do after undergrad (I want to help people harness the new paradigm of work). However, I discovered the problem I wanted to solve through reading, writing, and conversing—all forms of testing and learning.

If you don’t know the problem you want to solve, you identify it by testing out ideas for what you want to solve and learning from your experience.

The Jump

I’m still testing and learning today. 

In June 2016, I packed my bags and moved to NYC to start my dream job at The Ready. After three fulfilling years, I left to explore my next opportunity. I’m currently exploring opportunities from being an internal agile coach, to being a product manager for a company that makes collaboration tools, to being a consultant in the people analytics arm of a multibillion dollar tech company. I’ve taken on four freelance gigs (ranging from editing books about self-managing teams to facilitating a half-day work session for a major consulting firm) and have had more coffee meetups than I can count.

At the onset, I was filled with optimism. I gained a lot of valuable experiences, learned a lot from my colleagues and clients, and was psyched to make The Jump. Now, there are so many things I wish I knew before The Jump. I hear the same thing from my friends when I ask about their journeys: “There’s so much I wish I knew before starting out my career.”

(Side note: arriving at lessons you wish you knew is a sign that you’re testing and learning.)

The purpose of The Jump is to share what I learn with others making The Jump as I navigate my own transition. I’m no expert at career transitions, but I enjoy writing down what I learn and helping people harness the new paradigm of work.

Fair warning, I strongly despise overly simplified advice, so The Jump can veer towards sharing a ton of context and overusing inductive reasoning. Ultimately, I want The Jump to be wide-eyed to the new paradigm of work, yet useful to anyone testing and learning their way toward their next opportunity.

I plan to share a lil something with you every Wednesday morning, right in the middle of your week. And I hope what lands in your inbox is useful, practical, and if anything, thought-provoking.

Are you ready to take The Jump?

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