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To millennials, with love (part 2)

‘It was one of the hardest decisions I have ever made. I haven’t slept in weeks. I spoke to as many people I could before reaching a conclusion… I’m not even sure I took the right path’, she told me as the coffee shop began to crowd up with locals on a sunny Thursday morning. The thrill of change and an evil empire were taking her away from us. No matter how hard I tried, no matter how many long conversations, new responsibilities, exciting plans or heartfelt posts, I had no chance from the start.

Whether you decided to stay in your current job or take the plunge to a new one, do not look back. You can be joining a start-up, a dying bank, a VC, an evil empire, or sticking it out at your good old desk, be ready to take your organization by storm. Starting strong means absorbing as much as you can, working harder than the rest, and engaging the organization as if you were there from its foundation. A strong start will help you gain or enhance your reputation, signal your determination to have more impact and grow fast from the get-go.

You did not take the jump or turn down that great offer to be comfortable. You’re in it to win.

Given you are the first generation to be raised with a digital backyard as your doorstep and playground, you are told that you are special. After all you were born with the Internet and nobody snaps as well as you do. Indeed, the millennial generation feels like a special bunch just as the generation X or babyboomers generation felt in their time. It seems every group is special until it is replaced by the new special. So, by deduction, we must all be special right? Well, no. Nobody can feel special if you are surrounded by billions of special people. However, I must say that among all millennials, you are indeed special… but only potentially. To be truly exceptional you need to fulfill that promise. It requires the humility of knowing how hard and improbable it is, and the unwavering conviction that you will eventually reach your peak.

To get there, I have a roadmap to pass on from my generation to yours about what matters most in the unique journey you are about to create. There are no wrong paths in this plan for every road can get you there and every path brings unexpected gifts. It is still unproven and in progress, but it just might work if you make it yours.

“Again, you can’t connect the dots looking forward; you can only connect them looking backward. So you have to trust that the dots will somehow connect in your future. You have to trust in something — your gut, destiny, life, karma, whatever.” — Steve Jobs

Who you meet

You may be working on a rocket ship full of geniuses, a slow transatlantic or a small wandering group of odd people, but when you chose a company, an industry and a city, you are in fact choosing who you meet: people you cross everyday, the topics of the conversations you have, the dreams you share, the bonds you create. Of the three industries I have worked in, being at a VC beats the beauty and retail industry hands down. It just feels better chatting about the latest innovation and disrupter than the newest fragrance or fashion designer. It’s so motivating to build bonds with founders from all over the world who want to solve problems.

As you evaluate every new opportunity for change, find out about the ‘who’ first. Not only your colleagues but the people you will interact with in a broader sense. Make sure you will share the same values and admire the people that work in the space you choose. Your friends and your mentors will be part of that group. At work, if you are introverted or too into that excel spreadsheet, take a break and go out meet the person next to you. Get to know the arrogant engineer, the insecure CEO or that lonely accountant. Get them to share their journey with you. You’ll be surprised how much you will get back for taking the first step.

What you fail

It is certain you will fail a few times in the future. In fact, if you have not failed enough by now, you may need to change your approach. Even if nobody plans their hits and misses in life, you control what you try. Thinking big is nothing more than choosing the size of your failure. So you must not let yourself screw up the small challenges for if you go big you will fail big: big because it is humiliating to lose; big because you were going against all odds; big because everybody predicted your downfall.

It is very rare that large companies will embrace you swinging for the fences. They are designed to avoid failures. So to fail big, you may need to apply for an internal move that makes no sense or work around what the organization expects. If you are working in a small organization, make sure what they are dreaming big as a group.

What you build

Every day, over the next couple of years, you will wake up early to contribute to building something. What you are building invariably colors your efforts to do the best you possibly can. Even if a higher purpose can always enhance a simple activity, a noble cause or impactful mission will always give you a larger sense of your place in the world. Provided you’re not pushing cigarettes to teens, gambling grannie’s pension funds or corrupting local governments, there is nothing wrong with working for a transportation company, a one-dollar shop or a rubber factory. It’s just way cooler to help families access health, help founders succeed, educated the young or build clean energy infrastructure.

Build stuff that matters. Even if your career is just starting, the world is so interconnected and fluid, you have the opportunity to choose what you build if you are patient enough and focus on what lasts. Brands, prestige and money are just bells and whistles.

What you learn

By now, you know a trick or two that make(s) you look great at work. When it comes to knowledge, most people tend to focus on the safe and feel trapped by the first things they learnt at work or by their university major. Soon, maybe brought in by the next special generation, AI will replace some of your proudest techniques. It’s ok. Let them have them.

What you can learn is much more important than what you know. Instead of the tricks and the information focus on soft unique skills: your intuition, your empathy, your resourcefulness and your creativity. Develop your capacity to motivate and organize complex projects.

At the end of the day, it’s all about being a good student. It has little to do with studying tons, pleasing the professors or spending long hours preparing. Good students are aware of their learning process. They develop a capacity to understand which allows them to move faster and to absorb more. Just like good students, great teachers never stop learning. So, never stop.

What you become

When studying at Stanford, while my Generation X was still popular, I became obsessed with the sometimes overused Robert Frost poem. I was at a crossroads then, and was lucky enough to decide among the many doors of opportunities an MBA opened. I felt I could choose any path, from investment banking to entrepreneurship to a corporate career.

Choosing the ‘road less traveled-by’ seemed like a simple enough plan to me and one that helped me explain the unconventional yet risk-adverse future I seeked. A decade later, I know things are way more complicated. I know for you, it must feel even more confusing.

The Road Not Taken Two roads diverged in a yellow wood, And sorry I could not travel both And be one traveler, long I stood And looked down one as far as I could To where it bent in the undergrowth; Then took the other, as just as fair, And having perhaps the better claim, Because it was grassy and wanted wear; Though as for that the passing there Had worn them really about the same, And both that morning equally lay In leaves no step had trodden black. Oh, I kept the first for another day! Yet knowing how way leads on to way, I doubted if I should ever come back. I shall be telling this with a sigh Somewhere ages and ages hence: Two roads diverged in a wood, and I — I took the one less traveled by, And that has made all the difference. — Robert Frost

Frost’s poem is still as beautiful as it was the first time I read it, just not as insightful as it felt before. Times have changed, I have changed. I’ve learned that it’s not about the roads you take, it’s about the person you become during your journey. The people you meet will influence you profoundly. Your failures will define you more than your successes. Your passion and how you dedicate it will define who you become. What you understand about yourself will matter more than what you know.

As much as failures can be positive, there is only one thing you cannot fail. You cannot allow yourself to fail who you become, even if you are thinking big. You know this and that’s why every choice you make feels hard. Because when you reach your potential and become the special you, you will be as successful as anybody can be. Who knows if that success will be expressed by wealth, power, recognition, redemption or nothing. When you get there, it won’t be important.

What matters most is love… and maybe the stars.

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I write about my work as an investor, a lecturer, and a mentor. In general, musings about Latin American tech, VC and life.

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