The Road To Mastery

via Nathan's Natural on Slideshare
via Nathan’s Natural on Slideshare

Controversial author Robert Greene’s two best books are his two latest works, “Mastery” and “The 50th Law”. Both are excellent and are a much quicker read than his Power, Seduction, and War trilogy which can be a bit dense. Both “50th Law” and “Mastery” are on my top-five book recommendation list for life and career planning.

Reading the two books multiple times over the years has helped me come up with different ideas on how I define myself and my career. It’s taken me nine years since leaving college and working in the real world to learn a lot of these things and these books have been very helpful along the way. Some ideas that I’ve either learned from these two books or that I learned along the way are below.

If You’re Going to Aim, Aim Big

Otherwise known as “Go hard or go home”: I think it’s incredibly important to set an ambitious goal for oneself for 5 or 10 years out. It may be something that today seems very bold and almost unfathomable, but it’ll help keep the mind sharp and focused on achieving that goal. For me, I want to run my own startup and have it make enough money to live comfortably off of that business.

Once the goal is set every step you make in your career and personal life should be towards achieving that goal. Because I want to run a tech startup, I know that I need to spend the time before launching a business improving my skills in both the areas I’m already strong in as well as in the areas I’m weak. I come from a customer background (sales, support, marketing, etc.) and I know I always have room to improve in that area. Where I’m weak is on the technical side: I know I need to learn computer programming in order to reach the goals I’ve set for myself.

I’ve been spending a lot of time over the past year in trying to learn as much about computer programming as possible. I know an entrepreneur needs to know as many different sides of running a business as possible, so this will only improve my ability to work in my field. Of course, there are many examples of non-programmers building successful tech startups, but I cannot assume that those outliers would necessarily be applicable to me. Just because Mark Zuckerberg and Bill Gates dropped out of college and became massively successful doesn’t mean that that’s the best answer for everyone.

Making Career Decisions

Now that I’ve set the ambitious 5-10 year goal that I want to make, every career decision I make is judged based on whether it moves me closer to that goal or not. If I feel like I’m working somewhere that isn’t progressing me towards that goal, then I know it’s okay to move on. There’s nothing wrong with changing jobs multiple times if you either 1) stop learning and progressing in your current job, and/or 2) aren’t quite sure what you want to do with your career. Switching jobs is such a huge jolt to the system it’ll force you to learn rapidly and there’s a strong possibility you’ll learn new things along the way.

I’m on my seventh job in nine years since leaving college (actually it’s more like 7 jobs in the slightly more than 7 years between college graduation and when I started my current job at Streak, but I digress). I know there are some HR managers at stuffy, oxford shirt companies that would see that on my resume and freak out, but they’re not my target audience: I don’t want to work for any place that doesn’t have entrepreneurship and risk-taking built into its core DNA. Plus, what I was actually doing was learning different things about myself and about the work world during that time. It took me to my current job at Streak to really know what I want out of a career (seventh time’s the charm!) and I’m glad I figured it out at thirty-one than at, say, eighty-one… or never learning it at all.

By changing jobs a lot I was eventually able to better define for myself what I want out of a career, an employee, bosses, and co-workers. If I would’ve found my current job right out of school I might’ve either messed it up or likely wouldn’t have realized all of the good things that I have in my current job.

Use The Time During Your Youth to Learn as Much as Possible

The biggest mistake many young people make right out of college is focusing too much on making money and making many of their career decisions solely based on financial reasons. Two companies may be offering you money but to pick one company over solely based on one company offering you, as an example, $5,000 salary more than the other is foolish. Dividing that 5k by 12 months and subtracting taxes means you’ll barely notice a plus or minus of 5k on your annual salary. Hopefully, you have a bunch of other decisions about why you would or wouldn’t work somewhere, in addition to just the total compensation package.

When you’re young and a fresh college grad you likely are still living a spartan college lifestyle and don’t have a lot of material possessions. Because of this frugality (by choice or force), you have a lot more freedom than a fifty-year-old with three kids and a two bedroom house and a $300k mortgage. Your personal burn rate of what you need to live off of is likely very low and it shouldn’t take much money to get you “ramen profitable” in your personal life. Having very few material possessions or needs is great because it means you have a lot of flexibility and the nimbleness to make bold and risky career moves.

If you want to cut a more entrepreneurial career and life path, use your first decade or two after university to take jobs with the primary goal of learning as much as possible to help you achieve your 5-10 goals. An example would be someone who wants to be a successful restauranteur: You can use this time to learn as much as you can about cooking, then after you can learn as much as you can as about the business side of running a restaurant. The experience of learning both skills will be far more valuable in the long run than only focusing on one area of expertise. I can’t imagine what would be worse: A chef trying to run a restaurant who doesn’t understand business basics or a restaurant owner who can’t cook everything on his/her menu in the event of losing their chef.

Ignoring the Golden Handcuffs

Many young people get trapped by very high paying jobs and get way too comfortable in their position in life. Making a lot of money is great but it can also make the mind go soft and one lose their drive and ambition. Also, it’s fairly easy to ramp up one’s spending habits but incredibly hard to turn that spigot off once it’s flowing rapidly.

It’s a bit foolish and naive in today’s economy to assume a current career will still exist in twenty years. Stay focused and hungry and prepare yourself for career instability and job fluctuation to be the new normal. Entire industries that exist today will be wiped out by the time the Millenial generation retires. The reverse is also true: Entire industries will be created that don’t exist today. Opportunities will arise for those who are mentally in a position to take advantage of them.

Find People Who Are Supportive of Your Goals

Life’s too short to work with people who don’t care about you and aren’t supportive of your goals and your life plans. Of course, we all have to take jobs we don’t like from time to time just to pay the bills. I get that. Just be sure to push yourself towards positions where people are 100% supportive of your career plans. I’m very supportive of Streak that I can share my goals with our CEO Aleem and he backs me 100% and tells me to let him know whatever I need.


When you’re young you have the opportunity to learn as much as possible to best position yourself for the future. The lure of getting trapped in high paying jobs is a strong one but the early part of your career should be focused on learning and improving skill sets. Many other people don’t have that luxury and have to work jobs just for a paycheck but keep focused on moving towards working in places that will maximize your ability to learn while you’re young; when you’re older you can then focus on maximizing your ability to earn.