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Career Moves

Career Coaching For Myself

I have given career coaching to hundreds of college students. But now as I am in the midst of a career change, I have some hard questions to answer and some tough decisions to make. I have been with the same company for 10 years, and it's been the only company I've worked for after college. I'm out of my comfort zone, and excited for what's next. In this post, I hope to compile some of the best career advice I've come across, in hopes it will help bring me some clarity.

By Far the Single Best Thing On Careers I've Ever Read, and Think Everyone Should Read

Tim Urban writes the blog Wait But Why, and he absolutely NAILS it in this post. What he is known for is taking a seemingly complex topic (like artificial intelligence, Elon Musk, marriage, procrastination) and makes it simpler, relatable, and funny through stick figures and analogies.

His most recent post is called How to Pick a Career (That Actually Fits You). It's a long post, but it's worth every second. Here is a really quick rundown of some of the highlights for me...

To figure out what kind of job or career is right for you, first you have to understand your Yearning Octopus...

Then you have to rank each of the tentacles based on their priority, putting them in a hierarchy. What are the non-negotiables? What is important? What is great to have but not at the expense of the others? What should you resist?

This is a lot harder than it sounds, because actually knowing yourself and your true yearnings requires diving into the subconscious, having a real conversation with yourself, and also requires enough life experience to even know yourself and what's important to you. And life experience is hard to come by, it only comes in the form of "what the hell" moments and existential crisis.

And in the part of the post that pertains most to me, he talks about how to look at the career landscape, tunnels versus dots, and why we shouldn't worry too much about the long term future. I'm just going to direct quote the next part...

Careers used to be kind of like a 40-year tunnel. You picked your tunnel, and once you were in, that was that. You worked in that profession for 40 years or so before the tunnel spit you out on the other side into your retirement.

The truth is, careers have probably never really functioned like 40-year-tunnels, they just seemed that way. At best, traditional careers of the past played out kind of like tunnels.

Today’s careers—especially the less traditional ones—are really really not like tunnels. But crusty old conventional wisdom has a lot of us still viewing things that way, which makes the already hard job of making big career path choices much harder.

When you think of your career as a tunnel, it causes an identity crisis in anyone who doesn’t feel sure of who exactly they are and who they’ll want to be decades from now—which is most sane people. It enhances the delusion that what we do for work is a synonym for who we are, making a question mark on your map seem like an existential disaster.

When you think of your career as a tunnel, the stakes to make the right choice seem so high that it explodes the feeling of tyranny of choice. For perfectionist types especially, this can be utterly paralyzing.

When you think of your career as a tunnel, you lose the courage to make a career switch, even when your soul is begging for it. It makes switching careers feel incredibly risky and embarrassing, and it suggests that someone who does so is a failure. It also makes all kinds of multi-faceted, vibrant, mid-career people feel like they’re too old to make a bold switch or start a whole new path afresh.

But conventional wisdom still tells many of us that careers are tunnels. As the icing on its shit cake—on top of helping us yearn for things we don’t actually want, deny yearnings that we feel deep down, fear things that aren’t dangerous, and believe things about the world and our potential that aren’t accurate—conventional wisdom tells us that careers are a tunnel to help us daunt the shit out of ourselves unnecessarily.

Today’s career landscape isn’t a lineup of tunnels, it’s a massive, impossibly complex, rapidly changing science laboratory. Today’s people aren’t synonymous with what they do—they’re impossibly complex, rapidly changing scientists. And today’s career isn’t a tunnel, or a box, or an identity label—it’s a long series of science experiments.

Steve Jobs compared life to connecting the dots, pointing out that while it’s easy to look at your past and see how the dots connected to lead you to where you are, it’s basically impossible in life to connect the dots forwards.

If you look at the biographies of your heroes, you’ll see that their paths look a lot more like a long series of connected dots than a straight and predictable tunnel. If you look at yourself and your friends, you’ll probably see the same trend—according to data, the median time a young person stays in a given job is only 3 years (older people spend a longer time on each dot, but not that much longer—10.4 years on average).

So seeing your career as a series of dots isn’t a mental trick to help you make decisions—it’s an accurate depiction of what’s actually happening. And seeing your career as a tunnel isn’t just unproductive—it’s delusional.

Likewise, you’re limited to focusing mainly on the next dot on your path—because it’s the only dot you can figure out. You don’t have to worry about dot #4 because you can’t anyway—you’re literally not qualified to do so.

By the time dot #4 rolls around, you will have learned stuff about yourself you don’t know now. You’ll also have changed from who you are now, and your Yearning Octopus will reflect those changes. You’ll know a lot more than you currently do about the career landscape and the specific game boards you’re interested in, and you’ll have become a much better game player. And of course, that landscape—and those game boards—will have themselves evolved.

So my biggest takeaway from his post overall is to really seek to understand my Yearning Octopus, which requires deep self analysis and conversation the truth, and from there understand that I don't need to have the next 40 years planned or committed, because over time, my Yearning Octopus will evolve and the career landscape will change. So there is no need to stress or worry now about step 4, 5, and 8 of my career, I should mainly focus on step 1, the next step, and know that based on that experience I will make a better informed, and presently unpredictable, step 2 and 3.

More Navigation for Career Decisions

This diagram is from Born For This by Chris Guillebeau. The book's tagline is "winning the career lottery - how to find the work you were born to do." In addition to reading the book, I attended a workshop in New York run by Chris where he went into depth on this topic.

The first big concept he talked about was to find work at the intersection of joy, money, and flow. Joy means finding work you enjoy doing. Flow means finding work that you are good at, work that you can get lost in. And money is what sustains you, and obviously we all need money to survive. You hit the career lottery when you can find all 3. Its not enough to only have 2. If you have joy and flow but not money, you're basically a starving artist. If you have joy and money without flow, you have unfulfilled potential, meaning, maybe the work is too easy and you aren't putting your top skills or strengths to work. And if you have flow and money but not joy, you lack purpose, or meaning, and might strive for more significance or more impact. The key is to find the right combination of variables that's right for you.

And it's not just about finding the right work, it's also about the right work conditions. Everyone has different things that are important to them. Flexibility of schedule, reporting and accountability, social environment, sense of contribution, collaboration, deliverables and metrics, security, and intangible benefits should also be take into consideration. So if you have a horrible boss, you will probably be miserable despite how great the work is. You might be willing to sacrifice some money if there are lots of intangible benefits. And working remote versus having to sit in traffic and show up to a 9-5 could also matter a lot.


I like this a lot because no job or career is perfect and hits all of these variables perfectly, its more about understanding what's most important to you, and the trade offs that you are willing to make. It provides a good framework for making a decision about leaving a current job or starting a new career.

Ikigai is a Japanese word that doesn't have a straight English translation, but it basically means - a reason to jump out of bed in the morning. It means a reason for being, and it's where what you love, what you're good at, what you can be paid for, and what the world needs intersect.

I first heard about this when reading about blue zones, which are a few areas of the world where people live significantly longer than the rest of the world's population. This word/idea is said to have originated from the Japanese island of Okinawa, which is also said to have the largest population of centenarians in the world. One of the common things found in all blue zones is this purpose of life and reason for being. It's said to bring fulfillment to life, happiness, and help you live longer.

You can find your ikigai by asking yourself these four questions:

1. What do I love?

2. What am I good at?

3. What can I be paid for?

4 What does the world need?.

Obviously the answers to these questions require lots of self-reflection and self-awareness, and are not easy to come by. But asking the questions is easy, and is a great starting point. is awesome online resource for finding a meaningful career. Their aim is to help as many people as possible lead high-impact careers. The name comes from the number of hours you will likely spend in your career. 80,000 hours is a lot of time, so your choice of career is one of the biggest decisions you’ll ever make.

On their site they review some of the biggest problems in the world. They have problem profiles for biosecurity, climate change, factory farming, global priorities research, health in poor countries, improving institutional decision making, land use reform, nuclear security, positively shaping the development of artificial intelligence, promoting effective altruism, and smoking in the developing world.

In their career guide,, they review 60 studies to narrow down what makes a dream job. Many people think that your salary, or how stressful the job is, are the most important things... but they aren't. They also shed some light on the "follow your passion" myth, with a graph that shows the number of students passionate about sports, music and art compared the the number of occupations in art, culture, recreation and sport, and as you can probably guess, the number of those passionate heavily outweigh the occupations.

The formula above is their "formula for a perfect job." Look for work that you are good at, work that helps others, and supportive conditions like fair pay, great co-workers, and a lack of major negatives. Your personal fit is the multiplier on all these factors, thus the most important, but you usually can’t figure out your personal fit through introspection, you need to gain experience and try out different options with cheap tests. The biggest thing you get from this career site, different than most other career advice, is the importance of the work being high impact, working on a problem that the world needs and that you care about.

So the takeaway from these venn diagrams and formulas are that there are a lot of variables to consider when deciding on a career path or career move. It's not just about enjoying the job, or being good at it, or getting paid well, or the perks, or working with great people, or making an impact, or having freedom... it's about triangulating with all of these things. It's about knowing what YOU want. It's about tradeoffs.

Approach Your Career Like and Entrepreneur

The Start Up of You by Reid Hoffman and Ben Casnocha is the best career book I've read. Reid, as a veteran in Silicon Valley (PayPal, LinkedIn, Greylock), says that to be successful you need to treat your career like an entrepreneur would their start-up. You must invest in yourself, develop competitive advantages, and have plans and back-up plans. Here are some of the main ideas from the book, all such gems.

Permanent Beta Mindset

A permanent beta mindset means you look at yourself as a work-in-progress, and therefore, you must invest in yourself everyday. Beta is a tech term meaning a trial run, a first or early version, with the goal of obtaining feedback to improve upon. So permanent beta implies that there is never a final product, you are always learning and trying to improve yourself.

One way to improve on yourself is upgrading your soft and hard assets and developing a competitive advantage in the market. Soft assets are your skills, knowledge, relationships and connections. Hard assets would be like cash in the bank. Many start-ups prioritize learning early on over profits. Likewise for your career, it's often times better to prioritize learning (soft assets) early in your career over salary (hard assets). The way to prioritize learning is by doing. Start-ups launch beta-versions and minimum viable products (MVPs) so they can learn as they go. Your career is the same, you don't learn from just going to class, reading books, or attending conferences. You learn by doing, running tests, and gaining real experience and feedback.

Plan to Adapt with an ABZ Career Plan

Things usually don't go according to plan, especially in the fast moving world of tech start-ups. It's very common that a company starts off doing one thing, and then after getting customer feedback or changes with competition, they pivot and do something different. A company called Odeo pivoted and became Twitter. A company called Burbn pivoted and became Instagram. Reid Hoffman's company PayPal went from "beaming" payments from Palm Pilots to becoming the preferred payment method of eBay. And all of these pivots were impossible to see in advance or to plan for.

Old career advice says you should figure out where you want to be in 10 years, and then develop a plan to get there. In today's fast changing job market, it's also important to be flexible and to be ready to adapt. The 5 or 10 year career plan is a good plan A, something to work towards if everything goes according to plan. But it's also good to have a plan B and plan Z. An ABZ Plan is a flexible plan. You want to look at a career plan just like how a start-up founder would look at their company: There is a vision, lots experimentation and learning, back-up plans, and gradual improvement of the plan over time.

Plan A: This is the top career option you’d like to pursue, your ideal scenario. This is what you should be working towards right now. And because you also have back-up plans, you can think big and get risky here.

Plan B: These are nearby alternatives and back-up plans. You pivot to B when your plan A isn’t working or when you discover a better way toward your goal. Sometimes Plan B turns out to be better than Plan A. Remember “flexible persistence” so you are persistent towards your goals, but ready to adapt or pivot if needed.

Plan Z: This is your temporary fallback if everything goes wrong. It’s something easy to achieve, like a lifeboat you can jump in if your plan fails and you need to re-load before getting back in the game. Having a Plan Z helps you take bigger risks. Some examples of plan Z: Moving back in with your parents or crashing with a friend, getting an easy uncompetitive job to buy you some time, or maybe it’s selling all your things and traveling to a foreign country to volunteer.

It’s a good strategy to invest in skills that are transferrable, and more broadly useful than just in your specific career plan. Writing skills, general management experience, technical or computer skills, sales experience or learning new languages are good examples of skills with high option value, meaning they might not directly relate to your Plan A but could be transferable to a wide range of Plan B options. For example, you could sign up for a course or conference, or just commit to one hour per week of self learning.

Stir The Pot, Pursue Breakout Opportunities, and Take Intelligent Risks

The trajectories of remarkable careers are not slow and steady and up to the right. Rather, they are marked by breakout opportunities—career turns or experiences that lead to unusual rapid gains. There are a few habits to develop to increase the likelihood of these breakout opportunities. First, be in motion and court selective randomness, meaning, when you do something, you stir the pot and increase the odds that seemingly random ideas, people, and places will collide and form new combinations and opportunities. Second, tap the networks and associations of people, which can be as simple as joining conferences and clubs and meet-ups.

And every possible career move, especially breakout opportunities, contain risk. If you don’t have to seriously think about the risk involved in a career opportunity, it’s probably not the breakout opportunity you’re looking for. So here are a few ways to think about the risk associated with opportunities:

  • Overall, it’s probably not as risky as you think. We’re wired for evolutionary reasons to overestimate risk.

  • If you can tolerate the worst-case outcome, be open to it. If the worst-case outcome means death, homelessness, or being permanently unemployed, avoid it.

  • Can you change or reverse the decision mid-way through? If so, it’s lower risk.

  • Don’t conflate uncertainty with risk. There will always be unknowns. This doesn’t

    mean it’s a risk you should not take.

It's not possible to predict how or when ill-fortune will strike. But it is possible to build up your resilience. Learn how to deal with small risks. Those who regularly deal with small risks will never starve. They will never be engulfed by the big risks.

So in summary, take an entrepreneurial approach to your career. Invest in yourself and your career by focusing on your skills and relationships. Prioritize learning over salary early in your career. Have a career plan, but be flexible, be ready to adapt, and develop broad and universal skills beyond what is useful in your plan A. Pursue breakout opportunities and take intelligent risks that can rapidly advance your career, and always be stirring the pot to create these breakout opportunities.

Some of My Past Career Decisions

In reflection on my early years with CWP, I can see that I made a lot of decisions in line with the advice from The Start Up of You. I am who I am today, and I got to where I did with CWP because I pursued breakout opportunities, I took risks, and I invested in myself and prioritized learning and acquiring soft assets.

  • Doing the CWP internship as a senior in college was an example of pursuing a breakout opportunity and taking an intelligent risk. I read some bad reviews about the company which made me uneasy. I also knew it was going to be difficult and require a ton of hard work, but I decided to do it anyways because I knew that only an experience like this, something big and different, could lead to rapid growth and a change in trajectory. 
  • Deciding to take the promotion as a DM the following year was a perfect example of prioritizing learning over salary early in my career. I had just graduated from UCI, and I probably could have gotten a job at a normal company for $40-50k salary. But I knew I would learn a lot of new skills as a DM, and be pushed as much, if not more than intern year. I also had great mentorship under Brian, Derek and Matt.
  • Moving to Norcal as a DM was another example of pursuing a breakout opportunity and taking an intelligent risk. It was a scary decision because this was my first time moving away from Socal and there was a lot I left behind, and I only had 2 days to decide and make the move. On top of that, we were doing a mid-season restart, and completely flying off the seat of our pants. I slept on the ground and logged a ridiculous amount of miles on my car over the next 9 months, but we made it happen.  I ended up staying in Norcal for 6 years, and those 6 years defined my career with CWP. I learned things and had experiences and built so many amazing relationships that I would have never had if I would have stayed at home in Orange County.
  • And over the years as a DM and VP, I have been in permanent beta mindset and invested constantly in myself and my own learning and knowledge. I've probably read close to 100 books since my rookie DM year. As a rookie DM, Brian assigned us the book Developing the Leader Within You, and that was the first leadership or business book I ever read. Later that year I read What It Takes To Be #1 by Vince Lombardi, and I remember the epiphany I had like it was yesterday and still have the note I wrote myself while reading that book. The next year, Delivering Happiness by Tony Hsieh was big for me, and since then culture has been a focus and priority to me in business. I remember reading the Four Hour Workweek on a train in Europe while doing some solo travel over winter break. The list goes on, but I think it's so important to combine hands-on learning with simultaneous outside learning from books. Also, for me, reading lots of books helps me develop my own perspective, my own philosophies and opinions, and self-assurance and conviction in the way I approach things.

Looking to the Future

Wow, I'm going to miss CWP a lot, the people, the mission and the impact I made, and the lifestyle and freedom it gave me. But it had to end eventually, and I'm excited for the adventure that lies ahead. I'm grateful for the opportunity to continue to work/consult part time for CWP as I figure out my next move, that way I don't have to rush a decision or worry too much about money.

I always imagined that after CWP I'd start and run my own business. That is definitely my plan A. The freedom of being my own boss and working for myself have always been priorities to me, and the thought of a 9-5 job, sitting in traffic and going to an office everyday just never sounded appealing. Plan B would be to get a real job, besides for the downsides I just mentioned, the major upsides would be the consistent and immediate money, the potential learning of being in a new industry or environment, and the relationships and connections I would make. If I pursue plan B, I'd want to make sure I worked for a company where I believe in the mission, I like the people and culture, and I feel like I'd learn a lot.

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