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Today — June 6 — is my birthday!

I’m 27 years old. Yikes.

I’m officially in my late twenties now… which is both exciting and scary. I feel like my life is quickly passing me by and am suddenly anxious and introspective as to what I’ve learned so far.

I’ve always been so conscious of looking ahead and planning for the future, that I don’t often stop and reflect as much as I should.

A year from now, you’re going to be a year older. What do you want to do?

At the ripe old age of 27, I decided to compile 27 principles that have contributed to my biggest lessons (which include both successes and failures) in my life so far.

It would be interesting to look back on this 5–10 years from now to see if things have changed for the better or the worse.

One of the things I wished “lists” like these did was to include actual examples, not just vague takeaways that border almost meaningless without concrete support and context — because otherwise it’s just another list, right?

So — I promise you my own personal stories and examples with each lesson.

This is essentially my playbook for success and the first time I’m opening up and sharing these insights — some, less obvious than others.

This is part 1 (lessons #1–13), with a part 2 to follow thereafter (lessons #14–27).

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Here’s the complete list below first —

  1. Learn sales and how to sell yourself.
  2. Manage your energy. Do what gives you the most energy.
  3. Take (calculated) risks. Especially when you’re young. Get outside of your comfort zone.
  4. Every experience is a lesson. Nothing is a failure.
  5. Find your unfair advantage.
  6. Create your own opportunities.
  7. Learn and apply 80/20 principle to maximize your time and happiness.
  8. Build systems, not goals.
  9. You are the average of the five people with whom you spend the most time.
  10. Work hard. Work very hard. Work really freaking hard.
  11. Take time to invest in relationships.
  12. Learn how to ask for advice, but more importantly, how to apply it for yourself.
  13. Read every day.
  14. Put exercise and health as your top priority. You are what you eat.
  15. Compare yourself to yesterday, not to others.
  16. Don’t try to multi-task. Focus on a few things and do them extremely well.
  17. Always keep learning. Being good at two things is better than being excellent at one.
  18. Be very self-aware. Know yourself. Be comfortable and secure in yourself. Stop giving a fuck about what others think.
  19. Work with great people.
  20. Schedule everything. Put it on your calendar. Time box it.
  21. Invest in new experiences and new memories. Lengthen “time.”
  22. Find your small joys. Keep a gratitude journal.
  23. Define success for yourself. Don’t let others define it for you.
  24. Stay open-minded and open to serendipity. Get lucky.
  25. Document and take time to reflect. What doesn’t get measured, doesn’t get managed.
  26. Stay humble.
  27. Your mentors don’t necessarily have to be in person. And what got you one place, won’t necessarily get you to the next level.

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1. Learn sales and how to sell yourself.

This is by far the #1 most important life skill you could ever learn in your life. Everything you do is sales — from college applications and job interviews to dating others and raising money.

If you read nothing else (and several of my other lessons on this list spill over from sales), I want you to really internalize the power of sales for success.

Sales not in the sense of a slimy car salesman. Absolutely not.

Sales in the sense of finding the best fit, finding a win-win for both you and the other party.

Sales here in the sense of knowing your “customer” (college, company, potential significant other, etc) and “product” (yourself) and being able to put your best foot forward. Understand their problems and priorities, as well as more importantly, you as the solution and best fit. Even better, if your own needs are aligned with theirs as well. Why you? Why them?

Learn to tell a great story. Learn to be the solution to someone’s problems. Sell yourself.

Sales — and by extension, persuasion — is the most important skill in life to learn. Absolutely no question about it.

Example: I learned cold calling doing an internship with Merrill Lynch (sure, glorious grunt work, but actually the catalyst of my “snowball effect” of success) — literally picking up the phone, speaking a script, and accepting rejection after rejection. Understanding objections and overcoming them. Getting less robotic each time. Getting less scared and more confident picking up the phone each time. Getting better at knowing my customer each time.

Getting better at “selling” each time. Even if it was something as unsexy as low mortgage rates.

I remember one day when I scored a “lead” (a complete stranger I called was indeed interested in learning more about low mortgage rates! They wanted to set up a meeting with my boss! Wow, really? Did I do that?), I was incredibly proud of myself and since most of the other interns had not progressed that far yet beyond many no’s and being hung up on from time to time.

It’s not easy to cold call.

I’m sure this ranks up there with the deathly fear of public speaking.

But I later leveraged this thick skin from cold-calling rejections to pitch my web design skills and talk my way into an internship with a Dallas private equity firm (whose CEO was former chairman of TXU Corp, the very same TXU of the same $44 billion largest leveraged buyout in history — yeah, kinda cool!)… this was after I researched, emailed and cold-called 30+ boutique investment banks in Austin, Houston and Dallas, back when I wanted to get into oil and gas investment banking.

I went through at least 20 “no’s”, four “maybe’s” (bankers love hustlers who cold call, by the way) and finally, one “yes” — this was back in May 2010, when most of my classmates already knew what they were doing that summer.

Ultimately, I picked up the phone and convinced a managing director — a complete stranger — to give me a well paid internship so I could better learn financial analysis and modeling in the oil and gas industry, in exchange for building their website. Actually, I convinced them to create an internship for me — they weren’t hiring for interns. But I pitched them well.

And hey, my website design is still there today since 2010 (though to be fair, it’s nothing super fancy or amazing).

…this isn’t even my best “sales” or “selling yourself” story yet.

Some people may call this “hustling” — and yes, it is hustling. But at the end of the day, what is hustling? Sales plus determination and grit, plain and simple.

But mostly sales.

I’ll talk more about each opportunity I leveraged in the past due to selling myself, but that was the start.

2. Manage your energy. Do what gives you the most energy.

If you haven’t read this book — The Power of Full Engagement: Managing Energy, Not Time, Is the Key to High Performance and Personal Renewal by Jim Loehr and Tony Schwartz — do yourself a favor and go read it.

It is one of my favorite books, especially since it has immediate practical applications.

Basically, manage your energy to maximize your productivity and quality of hours worked, rather than quantity.

To me, it’s understanding myself and how my body works, after years of experimentation and habits.

This took me a long time to internalize and come to terms with myself and my habits and lifestyle — you need to listen to your body and observe what works best for you. For instance, do you work best in the morning, afternoon or night? Don’t try to mold yourself after magazine articles; I only use those success stories as guidelines — for instance, you don’t need to meditate for 10 minutes every day if you find that boring and a complete drag (but nothing against you if you do meditate).

Oh, and all those articles praising early birds? Or those articles praising night owls for their creativity? OK, whatever, honestly. Don’t read too much into those things — less words of reading articles of list after list of things to do, more action in confirming or disproving hypotheses.

There are many data points out there, but you are one unique person.

Just do what works best for you.

Do what gives you the most energy. What have you done in the past that worked for you? Why did it work? What about things you’ve done in the past that didn’t work? Why didn’t it stick?

Managing your energy is by far the most important thing you can do for your productivity.

Example: I am not a morning person in terms of working out. I just am not — though I’m perfectly aware many others work out in the morning and swear by it. I always work out in the early evenings or even at night. There have been times I’ve worked out at 11 pm since my gym at the time was 24/7 and I’d go home at 1 a.m. — I’m not even joking (but I don’t work out that late anymore). I’ve worked out in evenings so much throughout the past six years or so that it almost feels like my body feels absolutely primed for working out at those hours. And you know what? That’s completely okay.

That’s not to say you can’t train your body and build new habits to combat old ones, but it’s just the self-awareness and those moments where you catch yourself and know yourself and what will give you more energy versus what will not.

I encourage you to play around with your habits and challenge your assumptions about your energy. You will also probably go through cycles and phases — I know I definitely have in terms of drinking tea vs. coffee vs. protein shakes (for now, coffee is the only thing that is sticking that I’ve observed has positively affected my productivity).

3. Take (calculated) risks. Especially when you’re young. Get outside of your comfort zone.

People always say this, and I always sort of shrugged it off.

What does “risk” mean? What does it really mean to “get outside of your comfort zone”? It’s different for each person — what may be risky to someone, may completely be a non-issue to another person. Likewise, one’s comfort zone may not be the same as that of another.

But I mention this here in reference to the biggest gamble of my life — working on two startups I cofounded.

You’re going to get more and more risk averse as time passes by, so the time to start thinking about your bucket list and dreams is while you’re still young.

However, don’t rush into things blindly — take calculated risks that play to your strengths with potential upside. Build upon skills you already have, but may not have polished or refined yet.

Don’t do things you haven’t done before, in one way or capacity. Look at your background and connect the dots.

Example: I realize the privileged position I was in to cofound two startups (albeit failed ones) when I was 23–24 years old, and honestly looking back, knowing what I know now, I’m not sure I would’ve taken the plunge then. But I had savings, I was living with family friends with heavily discounted rent, I had a good resume otherwise, I was in a culture and environment where failure was like a “badge of honor” (i.e., Silicon Valley), the market size was huge, I felt we truly were differentiated and unique, and so forth.

So was it really a risk? It was extremely scary looking at my peers in investment banking, consulting and BigCo tech companies making six figures and vacationing in Paris and Zurich while I was slowly but surely burning through my savings with next to nothing to show.

But to tell you the truth, I started an online magazine in high school, a club organization in college that raised thousands of dollars, a fledgling side business in web design… things that ultimately failed or fizzled out, but were “startups” in their own right.

Needless to say… I’ve failed at a lot of things in my life. You wouldn’t even believe.

And again, I’m pretty good at sales and had no issue reaching out to users and customers, recruiting others, pitching sponsors, etc — not to mention the skills and lessons I learned (I’m incredibly grateful I got to build both a B2C and a B2B startup to learn the challenges and nuances of each world) and opportunities I gained (e.g., the chance to talk to commercial general contractors whose clients include Google and Square in San Francisco and an invitation to pitch practice at Greylock Partners).

Leverage your strengths and take (calculated) risks when you’re still young and not as risk-averse. You won’t regret it, I promise.

4. Every experience is a lesson. Nothing is truly a failure.

I’ve failed at so many things in my life. So. Many. Things.

But I never look at it as failures. Everything taught me something that helped me move forward.

Example: Sure, my startups failed, but I gained a tremendously profound understanding of challenges B2B startups face, for instance, in half the time (e.g., domain expertise, customization, long sales cycles, buyer vs. end user, etc). I later spun that as an interest in B2B and enterprise product management and talked to 50+ product managers at B2B and enterprise companies in SF and Silicon Valley. Sure, my online magazine and other ventures failed back in high school and college, but I came out of each “failure” with stronger skills and experience at what didn’t work.

You need to strategically pick your “risks” and experiences in a way that you are constantly learning and growing.

And yeah, you guessed it — this also ties back to sales and selling yourself and telling a good story.

Oh, and — to stop talking about work for just a second — I’ve had many first dates, fewer second dates, even fewer third dates and so forth. But obviously not every date worked out. And not every relationship worked out, either.

Each “failed” first/second/third/fourth etc date was definitely a lesson — in what I like and don’t like in a person, or vice versa. I’ve gotten better and better at gauging whether or not I’d get along with someone based on his priorities, preferences, etc. If something or someone is worth fighting for. What I want in a relationship and my dealbreakers or dealmakers.

It’s very difficult, but you get better at it over time — but it only comes with experience (or as you could also frame it, “failures”). You won’t get better if you don’t try and put yourself out there.

No matter what happens, think of each experience as a lesson, not a failure.

This applies in all aspects of life, not only in your career and relationships.

5. Find your unfair advantage.

This goes along with selling.

What is your unfair advantage? What can you use when you sell yourself? How can you leverage your past experiences?

What do you have that nobody else does?

It’s like a snowball effect.

Example: I’ve done systematic networking and understand the end-to-end process of selling myself and created opportunities for myself. I’ve interned in oil and gas investment banking, done stints at household name companies like Square and Evernote, created both jobs in my life so far at Evernote and Lending Club (more on that later), broke into product management without a CS/engineering and MBA degree (the PM intern at RetailMeNot prior to me was both a Stanford MBA and Stanford CS undergrad), intuit good design and user experiences, understand building B2C vs. B2B products through two startups of my own, and established key relationships in the industry in the process.

Those are my unique selling points, but I think more importantly, I developed unique and “unfair advantage” skills in learning the art of sales and storytelling and selling myself — and thus, leveraging each and every single past experience to get to the next one.

Here’s a great story —

Back when I had my heart set on oil and gas investment banking as a rising junior, and secured an oil and gas private equity internship in my back pocket (remember how I built their website?), there were banks who came on campus at Rice University, my alma mater, and they were mainly there for full-time recruiting.

One of them was BMO Capital Markets, a Canadian investment bank.

The VP on campus wasn’t looking for juniors for summer internships; he was interested in recruiting seniors for full-time jobs. However, I reached out cold and asked him if they were hiring, especially given my past experience in oil and gas private equity — and he asked me to keep in touch in January to see if they had resources and opportunities.

I followed up that January and it turned out they were hiring summer interns. However, since I had reached out to him first, and apparently was the only one from Rice to do so, and leveraged my oil and gas past experience (this was the energy group of BMO, after all), I “sold” him on my unfair advantage — and ended up completely leapfrogging over all of my competition at Rice.

They didn’t even come to Rice to recruit for juniors —they did at UT-Austin, SMU and Texas A&M, though— but I was invited to their superday (whole day onsite interviews) and ultimately given an offer.

Yeah, that happened.

…I think you can probably begin to see a common theme among these life lessons. Sales, sales, sales! But also leverage and story telling.

There are some days where I see my peers getting into Harvard or Stanford medical school to become surgeons and ask myself what have I done with my life? I’m still a disappointment to my Asian parents who still push me to attend graduate school.

But then I think back to what I’ve accomplished so far and I’ve done a great job of pushing my “unfair” advantages.

It’s those intangibles that make for a great story — it’s pretty well-known and documented on how to get into medical school, but not so much using “unfair” advantages, sales and leverage in carving out unconventional paths to success.

6. Create your own opportunities.

Don’t be discouraged.

A lot of people email me for advice, whether it is about getting into product management and networking or interviewing — I’m like a career guru or something.

But why?

Because I go against the grain and use unconventional means for career growth and job opportunities.

Because I have an acute understanding of sales, story telling, leveraging my strengths, systematic networking, and research.

Because I’ve consolidated everything holistically into one repeatable framework and system.

I’ve created both jobs I’ve had in my professional career so far — yes, created — first, as an Associate Product Manager at Evernote (their first one) and second, as an Associate Product Manager at Lending Club (their first one as well) and later promoted to Product Manager at Lending Club.

Both companies weren’t hiring — but I reached out cold to them and successfully sold them and persuaded them to create roles specifically for me. That, coupled with zero competition (did I mention they weren’t explicitly hiring for these roles?), was a formula for success.

Not even talking about the roles themselves and how hard it is to break into product management without a CS/MBA background — more impressively, yes, it was a repeatable process for me.

Quick, what is the first rule of Melissa’s 27 life lessons?

Learn sales and how to sell yourself.

Once you master that, you can create amazing and unique opportunities that no one else can get and everyone will wonder how you did it.

Oh, and being completely immodest here — I made it happen not just once, but twice.

And at household name great companies, not unknown garage band startups.

Example: I’ve singlehandedly managed to create my own opportunities at absolutely every step of my career —

  • Internship at Bluescape Resources — After dozens of rejections from cold-calls, I successfully cold-called my way into creating a well-paid internship with top professionals in the oil/gas world. They weren’t looking to hire, but I convinced them to hire me anyways.
  • Internship at BMO Capital Markets — this was not advertised at all nor did BMO come to Rice to recruit for internships at all. I cold-emailed a VP at BMO that fall, pitched myself and followed up three months later, selling myself with relevant oil and gas experience from Bluescape — they invited me to the final round interview and I bypassed all of my competition at Rice in doing so, and ultimately got the offer.
  • Internship at Square — okay, this was advertised online. But I sent in a 10-page marketing plan and during my first phone interview, my Square interviewer interrupted me and made an offer halfway through. After 15 minutes. Seriously. It was an incredible feeling.
  • Internship at RetailMeNot — okay, this was advertised online (I found out about it on Quora, of all places!). I cold-emailed all the product managers there, drove up to Austin (3 hours from Houston) and had coffee with one of them. While the previous PM intern at RetailMeNot was a Stanford CS undergrad and Stanford MBA, I expressed enthusiasm about RetailMeNot and brought relevant experience from Square — and I got the offer call a week later!
  • Associate product manager at Evernote — I flew to San Francisco on a networking trip, reached out cold to a product manager there, convinced him to meet me for coffee, pitched myself, worked 40+ hours on a final presentation to improve the Evernote iOS product, and got an offer as the first associate product manager at Evernote. I had relevant experience from Square and RetailMeNot, both budding household names and great company brands, and more importantly, had previous product management experience and passion for the product. They weren’t looking to hire, but created a role for me anyways. This was my absolute dream job and I was unbelievably, deliriously happy I made this happen all on my own.
  • My two startups (Cusoy and Aecore)— gained both B2C and B2B experience and appreciated the nuances of both worlds in terms of the different challenges in product development.
  • Associate product manager at Lending Club — I reached out cold to the VP of Product, convinced him to meet me for coffee, and successfully pitched myself. I passed through an onsite interview and they created the first associate product manager position for me at Lending Club (exactly what happened with Evernote!). I sold them on my previous product management experience and what I could bring to the table as well as what I was looking to gain and learn from working at Lending Club.
  • Product manager at Lending Club — after a year at Lending Club, I was promoted to product manager, and where I still am today. I work on medical, tutoring and K-12 tuition loans.

I wanted to outline the above to show you step-by-step how I was able to leverage each role and more importantly, create my own opportunities despite there not being an explicit job posting.

I didn’t let that stop me at all — I had an established process and system in place, something I had started as early as college and something I fine-tuned over time.

This was not something that happened overnight, but something I had also experienced many failures in order to get to my big successes and big wins.

7. Learn and apply 80/20 principle to maximize your time and happiness.

If you haven’t heard of the 80/20 rule before, it essentially means that in your life there are certain activities you do (your 20 percent) that account for the majority (your 80 percent) of your happiness and outputs.

One example in business is that 80% of your revenue may be generated by 20% of your clients, or 80% of your team’s productivity is generated by 20% of your team members.

In terms of personal life, pick an area of your life where you feel there is an imbalance of effects. This won’t be true of all areas, but many situations may be out of balance (money, time, health and possibly even relationships).

Personally, this meant for me to be comfortable with exchanging more money for more time in my life, which was one of the more difficult lessons I learned.

Example: One of my biggest pain points was living outside of San Francisco for a couple years, since I originally was working in the Peninsula and didn’t want to pay absurd rent and also have a ridiculously long commute. But then once I started working in San Francisco, I spent at least two hours every day on the train and it started to wear down on my happiness and energy.

I then decided to move into the city even with its exorbitant rent — now my commute is literally 1/4 of what it was before and I have more time and more energy back in my life for other things than sitting on the train.

I don’t regret this at all. Here, for me, the exchange of a lot of money for a lot of my time was totally worth it.

I completely understand this may not be the case for others. But it was something I learned about myself that would have a huge 80/20 impact on my life.

There are many other things I could have done with that rent money — pay for personal training sessions, take golf lessons, take tennis lessons, learn how to cook, buy more furniture or art, go to music festivals and concerts, etc… but I’ve realized these don’t make me as happy or productive as simply getting back more time in my life by moving into the city.

Focus on activities that produce the best outcomes for you.

Place them first and prioritize them first — and likewise, eliminate those that just aren’t working and don’t give you a good return on your investment.

Your priorities are reflected by how you spend your time and money — if I looked at my calendar and my bank statement, would I be using the 80/20 principle to maximize my time and happiness?

What are some 20% levers that can contribute to 80% of your happiness? What is important to you? What can you do to maximize this?

8. Build systems, not goals.

This is one of the biggest levers in my life and one that changed my life — it drastically increased my happiness while simultaneously decreasing mental load and balancing expectations of myself.

Stop focusing on the goal and milestone that has a make/break mentality, and instead focus on the process.

James Clear said it best in his article: Forget About Setting Goals. Focus on This Instead.

I’ll wait for 10–15 minutes while you do yourself a huge favor and go skim that article.

This is also the biggest takeaway from Scott Adams’ book How to Fail at Almost Everything and Still Win Big, one of my favorite books for how practical it was.

Example: I made a goal for myself to get a PM job after my second startup failed, and because I had built such a robust system of essentially a job seeking funnel optimization, complete with custom tailored copy/pitch, tested tried-and-true subject lines, CRM follow ups, etc — that I just trusted my system and wasn’t really concerned as each day went by when I was unemployed and burning my own money, or when an interview didn’t go so well.

Each day I just followed my own system and removed emotions and willpower from affecting my productivity and morale.

For instance, I knew that if I emailed at least 25 leads a day, followed up with those who opened my email but didn’t respond, followed up with those who didn’t open my email after seven days, etc — essentially, following my systems and processes — I knew an offer would come (assuming improved performance at interviews, honed over time).

And it did.

Especially since I had built this system starting back actually freshman year of college in 2008, I knew my system worked.

It produced interview after interview, call after call, meeting after meeting, and ultimately — offer after offer at excellent companies where I worked with amazing people.

Caveat: I’m not saying don’t create goals, ever, but really focus on building the systems, and accomplishing the goals will come.

Trust the system.

In my experience, most people spend too much time and focus on the goals and not as much time on the systems to do so.

9. You are the average of the five people with whom you spend the most time.

This is pretty self-explanatory.

This is not PC, but life is too short not to be brutally honest about this — but after passing through my early and mid-twenties and learning this the hard way, I firmly believe you should be extremely selfish and discerning with your time. Time is increasingly precious to me and I’ve become extremely protective about my time.

Spend time with those who will lift you up and help you grow as a person.

Not that every interaction or relationship is transactional, but that there is a mutual value between the two parties. That you get a certain positive energy about it. That you learn something new. That it feels good.

That you don’t feel emotionally drained. Or unhappy. Or used.

Not all relationships are equal.

Not all relationships are meant to last forever.

Sometimes, relationships are just meant for a specific time and purpose.

Don’t waste your time trying to revive a relationship just for the sake of it.

If you want to lose weight and get healthier, don’t hang out with people who eat out constantly and eat unhealthy junk food. There’s too much peer pressure that studies have shown you probably should just remove yourself from that situation entirely, than try to overcome it.

If you want to go to the gym more, hang out with friends or people where fitness is a priority in their life.

If you want to be better informed and well-read, spend time with people who follow the news, not those who just talk about the latest celebrity gossip and who are blissfully ignorant about what is going on around the world.

Those are pretty simplistic and straightforward examples — but if you want to take yourself to the next level, hang out with people who are smarter than you, who are more well-read in diverse subjects who can teach you about things you otherwise would not have known about, etc.

Example: I used to think I had to keep in touch with every single person whom I met, either in high school, college, informal coffee meetings, etc… and it was absolutely absurd.

I used to torture myself about older friendships that somehow fizzled out, and did absolutely everything I could and made all the excuses in the world for the other person — before I finally gained some self-respect and realized it wasn’t worth it.

I spent so much energy being worried about losing touch with people (what if something happens in the future that I need them?), especially with people I had pretty much nothing in common with other than superficial things like going to the same college… why? Just because.

I struggled so much trying to fit into social circles composed of people with divergent interests from myself and thus made myself extremely unhappy and miserable.

This was a really big learning experience for me, actually.

Gaining confidence in myself (and my quirks) took me the past several years to really take shape.

It took me a really long time to realize that I actually treasure a smaller group of very close, tight-knit friends with whom I actually had common interests (extremely ambitious, fitness/health is a big priority, learning/growth/self-improvement is a focus, etc) — rather than a large group of superficial acquaintances.

And you know what? It’s perfectly okay.

Also — FYI, for those of you reading who are in your early 20’s or younger, I read that the majority of your life relationships and friendships are created between ages 23–28.

You’re going to make fewer friends as you get older.

You’re going to see fewer friends as you get older.

Make sure they are the ones that count. Don’t waste your time otherwise.

And by extension: you are a reflection and product of your environment.

I am currently paying way too much rent to live in San Francisco, but you could not pay me a million dollars to live in some rural town in the Midwest or South, etc because I know I would be so miserable being away from my friends and around people who I admire and who can help me grow.

To me, people and relationships are the most important thing — not to mention this is the best place for my career — and I am acutely aware that you can quickly become a product of your own environment.

Culture in San Francisco is different than culture in Los Angeles is different than culture in Chicago is different than culture in Denver and so on.

Culture and by extension personality, values, emphases, demographics, etc…

Again, there is no right or wrong answer here. But it is definitely one of the most important things to consider, in my opinion.

When you look at cities, countries, neighborhoods — and the people who live in them — do they match your values? Do they match your lifestyle preferences? Do they match your needs? Would you be happy?

10. Work hard. Work very hard. Work really freaking hard.

Grind it out while you’re still young, have energy as well as the least obligations.

I’d rather focus on my career and work now, build the skills and put in the time, than “coast” in my 20’s and suffer for it in my 30’s.

Now is the time.

There are no shortcuts in life.

My entire life I’ve worked extremely hard (and worked smart) and because of it, gained opportunities I never had dreamed of and opened doors.

Think of this as an investment in yourself.

However — you need to work on the right things, and work smart and strategically, not necessarily just focusing on the absolute number of hours worked.

The phrase “deliberate practice” and that whole concept from Cal Newport comes to mind, but that is a separate lesson in and of itself… for another time.

But you know that feeling how sometimes people make things look so easy and unfathomable how they got certain opportunities or outcomes? Trust me, you don’t see all the blood, sweat and tears and failures that took them to get there.

There’s no such thing as an overnight success.

As Britney would say, “Now get to work, bitch!

Example: I remember for my Evernote APM interview, I spent 40+ hours that week preparing my presentation of how to improve Evernote iOS, rather than time spent studying for finals.

I don’t remember how I did on those finals, but I know I spent my time on the right thing with outsized impact and ROI on my life and my career.

Also, for my first year at Lending Club, I worked long hours and became a domain expert in several areas for my team and business line; pretty quickly, I gained a positive reputation of being very thorough and having a strong work ethic with my colleagues — to the point where they had gushed to my boss (and then even upwards to my boss’ boss!) great things about me, which was a pleasant surprise.

Overall, you really need a strong work ethic to succeed in life — to set you up for even more opportunities given luck and timing.

Just be excellent at what you do — which comes with hard work. Don’t even think about making excuses.

11. Take time to invest in and build relationships.

Relationships run everything — I couldn’t get to where I am today without the help of others. Full stop.

The key thing here is to add value.

Don’t be afraid to reach out and build relationships cold (without any connection) — but also not to be that guy or that girl who only asks people for favors when they need something (e.g., we barely know each other and haven’t spoken in over four years, and you suddenly want me to take time out of my day and do you a big favor? Really?).

Add value to people.

Don’t just “use” them — it’s really obvious and a huge turn-off.

This goes back to sales, pitching and selling yourself.

Ask yourself: why should this busy person, who doesn’t know me at all, even bother to open my email and even spend time to schedule a call or coffee meeting with me? Why don’t they just delete my email and move on with their day? Why should they even bother to open my email, type out a response, commit time on their calendar for me — time that they will never get back?

What’s in it for them?

You have to think about it from this perspective.

I’ve been on the receiving end of people demanding many favors of my connections, my time, my knowledge — you name it.

Hardly anyone comes to me and says hey, I noticed XYZ is important to you and I recently came across this article that I think you’d find interesting.

No, it’s just take, take, take.

This annoys me to no end, now that I’ve been at both sides of the table.

So much, that now I absolutely refuse reaching out to anyone without knowing that I can add value to the conversation first or at least demonstrate I’ve done my homework and research beforehand.

This is table stakes, really.

Obviously, your mileage may vary, and this is not to say that every relationship is like this, but this has always been a guiding principle for me.

Example: After writing my Cusoy postmortem (how my first B2C startup failed), I’d routinely get emails from strangers reading it to ask me for help on their startups without any context or reason why I should give them my time. I want to help others — but these were short, curt “demands” on my time and energy that offered nothing of value in return to me.

Poor sales and poor pitching — why should I spend my limited time to help you (a complete stranger), what exactly makes me uniquely qualified to do so, and what have you actually done so far that you feel I can help? I’m not open to someone randomly “picking” my brain when all of my lessons are already online and public for everyone to read — a lot of lessons are also actually taught by experience, believe it or not.

If you are specific and targeted with your questions, offer something you’ve tried but didn’t work, were in the same market/space as I was, etc — that would be a different story and a far more interesting conversation that I’d gladly take.

Hardly anyone does this — so if you do this, you’ll stand out from 99.9% of everyone else.

Trust me.

Oh, and please remember to use the double opt-in principle when making introductions. Google it if you aren’t sure what double opt-in means.

12. Learn how to ask for advice, but more importantly, how to apply it for yourself.

This is another huge lesson, with the context more towards career and startup advice.

There are so many opinions on the internet and in real life — how do you filter out the signal from the noise? Even from smart people and trusted sources?

It’s not easy.

I learned over the years two critical psychological principles — confirmation bias and survivorship bias. That is, the tendency to interpret new evidence as confirmation of one’s existing beliefs or theories (confirmation bias) and the logical error of concentrating on the people or things that “survived” some process and inadvertently overlooking those that did not because of their lack of visibility (survivorship bias).

What does this mean? Advice on how to grow your business — or how to look for a job or <another question>, you name it — is heavily skewed by whatever works for the person you are asking, which, incidentally, may have been the complete opposite experience for someone else.

Let’s just say that there are many paths to Rome — and you will get biased opinions from someone’s specific circumstances and situation, which may or may not actually be helpful specifically for you.

You need to always dig deeper into someone’s story and situation, to tease out the circumstances and truly understand what happened that lead him or her to make a decision from A to B, etc — like an investigative journalist.

Then you need to make a decision for yourself. Does this apply to me? If so, how?

Regarding survivorship bias — you hear about infamous Harvard college dropouts like Mark Zuckerberg and Bill Gates who are outliers who achieved massive success and became billionaires, but never about all the other failed college dropouts who didn’t do so well.

For every success story that shines in the media spotlight, there are thousands — if not millions — of unwritten failures that nobody will ever hear about or care about.

Does that mean you should drop out of college?

Probably not — but then again, who am I to tell you what to do with your life?

You need to research and gather as many data points as possible, then make a decision for yourself with your own situation and best interests in mind.

Take every single piece of advice with a huge grain of salt, including mine. Everything I write here is 100% based on my own experiences and successes and failures, which may or may not ring true for you.

Example: When I first traveled to San Francisco for my first networking trip back in March 2012, I was debating whether to go into business development or product management. After speaking with 10+ who worked in either function as their current role, I made my own decision to go into product management — then actually had to forge my own path into product management afterwards, even with all the obstacles I faced.

13. Read every day.

Educate yourself. Invest in yourself.

I can’t think of a better way to learn than reading every day — and especially books!

A smart person spent a significant amount of time and effort distilling his or her thoughts about a certain subject into 200 or 300 pages, etc— all of which you can gain with the small amount of $15–25.

Don’t just read what’s in your comfort zone (for me, this is nonfiction) — but also spend some time reading other genres as well (for me, fiction).

I also would advocate following key influencers in your industry to keep up with the latest news and trends, as well as carrying out your civic duty as a well-informed citizen by reading the news.

Example: In another example of leveraging systems over willpower — instead of expecting myself to read 25 books a year (which, given how much of a struggle it was then to get through one book, would have not happened), I now try to just read 25 pages a day, without fail.

Once I started to focus on that, I actually got through several books in a single month and actually made more progress than I had after making that kind of goal for an embarrassingly long time.


Thanks for reading this far — Part 2 is coming soon! Stay tuned.

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