Looking Back 5 Years, Hindsight is 20/20: What I Would Tell Myself At Age 18

By January 14, 2014 Uncategorized No Comments

Looking back, I’m proud of what I’ve been able to accomplish since 2009, but I would have executed differently if I had known what I know now:

The (realistic) order in which to pursue goals. In other words, which goals to focus on now, and which to focus on later.

Lack of clarity in this one area is the problem with the current generation of young adults, the people sitting between Gen Y and Gen Z (ages 18-27).

The people ~10 years older than the current generation (ages 28-37) worked hard, became good at what they did, but may have developed quarter-life crises because they were limited in lifestyle options. They just didn’t know about the options around them, until years into their careers. With the then-recent onset of various factors spurred by the influence of the internet and emerging globalized economy…the ability to do things formerly reserved for high-net-worth individuals became accessible to the middle-class:

– hire PhDs to do your work (now, you could do it from India for $4/hour)
– start a business on the internet (now, you could do it with $100)
– learn coding and other skills (now, you could do it for free on Codecademy)
These opportunities were largely unknown or nonexistent until a few short years ago. People didn’t know about these new opportunities available until the early adopters empowered everyone to realize their dreams, because–news flash to some–there were no “limits” anymore.

Yay, globalization and the internet! Everyone celebrates until they see the state of most young adults now.

In contrast to the last, my generation is coming into young adulthood already saturated with the wealth of opportunities. The problem for us, ironically, is that the landscape of opportunities is too vast to explore in one lifetime–we get overwhelmed by options everywhere. For the first time, a generation is starting young adulthood already knowing they can…

– live and work anywhere in the world
– pursue traditional OR non-traditional education and still end up with a good career
– learn any skill–be it breakdancing, applying makeup, or coding–from 3 clicks on Youtube, Udemy, and Skillshare
– make money selling anything with Ebay, Amazon, or Shopify
– start a blog with WordPress for free, with a chance to get a book deal and become a NYT bestselling author
– and chat with famous people over Twitter


As more options are available, focus becomes increasingly difficult, and increasingly valuable. We are already seeing this with the evangelism of concepts like “Don’t Find Your Passion, Become So Good They Cannot Ignore You” (Cal Newport), obtaining “Mastery” (Robert Greene), and “Finisher’s Formula: Follow through on Everything” (Ramit Sethi).

These are all good resources for dealing with the problem of “option overload” faced by young adults today. If I could speak to my 18 year old self, the one who was about to dive into the real world–halfway through sophomore year in college with nothing but a strong work ethic, ambition and unbridled confidence–I would have recommended the above, and told myself what I’ll share with you now…

Whatever you want to do with your life, there is a framework for handling “option overwhelm”.

Caveat: Of course, this framework wouldn’t apply to most people. Most 18 year olds don’t think to themselves “I’m going to build an amazing, top 1% kind of life and career.” But my guess is…if you’re reading this, you probably also thought about it to yourself at some point.

Without further ado, below is an outline of the rough order I would go about building myself up professionally and personally, even without any ideas for what to do in the long term.



1. Learn ONE valuable skill.

The best skills are cross-functional, or highly technical. Here are some tried-and-true options: sales, writing, marketing, public speaking, design, technology, science.

Technology/science takes 6-12 months to learn enough to get an entry level position (e.g. 700 hours minimum needed for accelerated learning of web development), but 3-5 years before you feel really comfortable doing it.

Non-tech/sci skills take only 3-6 months to show competency for an entry level position, but only if you have a solid foundation in social skills, like if you were in the cool kids crowd in school, or did student government/theatre/debate club. If not, it will take 2-4 years of deliberate practice to be employable.

Only pursue tech/science if your social skills are in need of improvement and you need the money fast. Non-tech/sci skills will help you in virtually any pursuit, so invest in those as soon as your financial situation allows. If you have no preference, learn sales first, because the ability to sell forms the foundation of getting anything done at work, and at home. If sales scares you, and you’re average in social skills spectrum, do marketing. If sales scares you, and you’re below average in social skills,
As for how to obtain the chosen skill, the following options are listed in the order I would pursue them when optimizing for financial cost and time-to-income: job > internship > self-directed projects > vocational school > 4 year college. Obviously, a highly regulated field like medicine or law would have fewer options for qualification, but that’s outside the scope of this article.
Finally, learn how to sell your skill to others by talking in terms of numbers, results, analogies, and stories that stick. Since selling yourself is a necessary part of your skill set, it helps to be in sales or marketing and kill two birds in one shot.

2. Get “life/career” mentors and understand deep ideas.

Read the books on your field, the classics and contemporary books that have been long-time bestsellers, then reach out to the authors with a quick question you have that wasn’t answered by the book, or with a short message on what you applied from their book and what you learned. For the people with whom you really connect personally, give them occasional pieces of value, while updating them on your life. After a while, offer to intern with them, but only if their career and life looks like a rough projection of that which you want in the future. Get a combination of life/career mentors who are 3-5 years ahead (find 2-3 to start) and 10+ years ahead (1 is sufficient) of you.

3. Find work in your skill to cover expenses.

Or, find a well-established mentor to take you in as an intern. Either way, you will have job/financial security, either in having a valuable skill, or in having the skill plus a powerful network through your mentor.

4. Build a routine for productivity at work.

Do so well at your job that you have time on the side to think about other things. Negotiate for raises by setting performance goals with your boss 3-6 months in advance of a negotiation talk, exceeding those goals, then presenting a logical case for a raise. Max out on your job in bottom-line results, not time-in-office. If you get a promotion,  especially a management position, don’t take it. Exceptions:

A. It involves working with a powerful mentor,
B. You absolutely need to gain management skills for your long term goals, or
C. You are really good at navigating politics and holding influence in a group environment, and plan to work yourself up the management ladder of the company to become a powerful COO/”intra-preneur” like Sheryl Sandberg.

In the last case, the remainder of this post may not help you. In most other cases, management will make you too busy to do other, higher leverage things.

GROW [Year 2-4]

5. On the side, do these things in order:

a. Build a foundation of health.

Working on your body cultivates a special type of confidence, energy, and self-awareness that cannot be obtained by any other means, nor purchased with any amount of money. It also increases energy and mental capacity at work within days of implementation, and makes you more attractive within a few months, which is important because many studies have shown that, relative to less attractive people, more attractive people get more opportunities for higher salaries, social engagements, leadership positions, and other benefits.

Be clear about the order of priorities:
– 80% is diet
– 15% is exercise and sleep
– 5% is everything else (supplements, drugs, caffeine, “superfoods”, “health hacks”, and other tactics) <–Many people get stuck focusing here instead of on the other 95%.

Diet in theory: Eat veggies, fruit, and meat/eggs/fats from healthy animals. Don’t eat processed foods, sugar, or grains (flour, pasta, bread, rice, corn). Drink water, tea, as little coffee as possible.
Diet in practice: 100% adherence to rules on Mon-Fri, with no adherence required Sat-Sun. Purge your house of bad foods, promise any housemates that you vow never to eat their food, buy and cook the same meals to reduce “decision fatigue” on weekdays (or get healthy food pre-made and delivered to you for $7-10/meal to eliminate cooking/shopping hassles), then eat out for enjoyment on weekends. Never bring bad food home unless you can consume it before Monday.

Exercise in theory: Workout 3-5x/week, no more than 45 min/workout. Combination of lifting heavy weights and short intense intervals (80%), and low intensity/”long and slow” workouts (20%, optional). Differences between men/women’s fitness training programs are trivial despite their vastly different desires (muscular body vs. nice ass/skinny waist), as they are across different sports (not counting sports-specific technique obviously).
Exercise in practice: Ever wonder why competitive athletes and ex-athletes seem to have no trouble sticking to a workout routine? It’s not willpower. They use an external structure system to ensure they workout consistency. 3 Options: hire and schedule 3x/week coach/personal trainer, use a Crossfit gym 3x/week which has built-in structure made for high adherence, join a local sports team, or agree to pay an athletically-attuned friend $5-50 every time you miss a workout day with them). Your local Crossfit gym, Stronglifts 5×5 with a trainer/friend, or anything in 4 Hour Body with a trainer/friend, is good for starters. Implement exercise-then-diet, even though diet is more important, because that tends to be easier than diet-then-exercise for most people, for some odd reason.

Sleep in theory: 8-10 hours per 24 hour period. Wake/sleep at the same times everyday.
Sleep in practice: Set an alarm for bedtime, not wake time. Test different bedtimes to adjust for desired wake time. Adjust caffeine intake time/dosage to allow for falling asleep within 5-10 minutes upon hitting the pillow. For me, that’s 12 hours before target bedtime, e.g. 9am if I want to fall asleep by 9pm, and no more than 1 cup black tea or 2 cups green tea (~50mg caffeine/day). I never drink coffee, but for reference, coffee is 100mg/cup.

A Note of Caution About Health: Experimenting with unconventional diets and exercise routines to increase ROI is encouraged because potential upsides are high, while downsides are usually short term. However, cutting down on sleep for more than 1 month at a time, per year, even to something as common as 6-7 hours, can result in a huge crash when you least expect it (e.g. when you feel at your “peak”). The potential consequence is being rendered unable to work a full time job for several years, or for life.


This happened to me, at the ripe old age of 19. Thankfully, because of my biology and sports background, I was able to treat myself in 3 years despite seeing 9 doctors who were stumped and left me hanging.

Don’t do this to yourself.

b. Build a social support network and social skills.

Go to self improvement and startup/entrepreneurship  gatherings 1x/week for 2-3 hours, where there will be growth-oriented people who just “get” you after a 5 minute chat better than your old friends from school/work will ever understand you.

If you are introverted, it will take you 1 year to become functional in networking, and a second year to become completely comfortable in socializing/networking, but it will fundamentally change you in an immensely positive way. If you are extrovert, you will pick up all the rules of engagement in 6-12 months.

Meeting 5-10 new people per event is a good metric to go by. If this is hard, remove any barriers to socializing. The most common are:
– not knowing what to wear, thereby being “written off” due to physical appearance
– using suboptimal speech and voice patterns
– inability to read others physically and control one’s own body language
– getting frustrated from wanting everyone to think and feel like you

c. Deepen or broaden your skillset through side projects. Find a 3-5 “tactical” mentors for each skill you build.

In contrast to “life/career” mentors–who should vibe well with you both personally and professionally–“tactical” mentors only have to be experienced in the skill you are learning in the moment. The best tactical mentors are those who are between 6-12 months ahead of you along the path of practicing the particular skill.

d. Keep notes in journal while learning, and share when appropriate.

As soon as you learn enough to help beginners, share it with others through coffee and calls. If it becomes so much that it would save you time by writing or speaking, do that instead and refer people to your talk/book/blog post so they don’t eat up your time. If speaking/helping others becomes too much, start charging money for it.

THRIVE [Year 5-8]

6. Start THE side project.

Keep doing A-D in #5 while doing the full time job until you have enough skills that compel people to pay you for them outside of your current job, in the form of sales, investment, or some other form of financial resources. That’s how you know your skills are good enough. Start a project using those skills after deciding that, yes, you would indeed like to do this for a long time and would rather do this than your job. Have it start as a side project first.

7. Quit your full time job when your side project makes you a professional.

“Professional” means you get paid a substantial amount of financial resources, enough to reliably cover living expenses and a bit of extra  (thank you Derek Sivers for the idea). Consider setting the minimum to $40K/year because that is the minimum amount to be “happy” according to  researchers, and roughly the average income among startup founders.

8. Grow the business using new and existing skills.

You should have 2-4 skills by now. On the side, when not maintaining the business at the current state, you should be deepening or widening your skill set. If doing services, productize your offering by pre-selling with existing customers, and testing with them until they’re happy with the product, then marketing to a wider customer base.

IMPACT [Year 9-10 and beyond]

9. Finish, reflect, and move on from your big business/project.

Your project will end somewhere along the spectrum between “massive success” and “humiliating failure”. Act accordingly:

If it was a “failure”, you learned many lessons. Consider it another form of #5C (building skills). Depending on where you fall, you may have to go back to the beginning of this list to #3 (get a job), skipping the other steps (#1 learning a skill, #2 finding career mentors). Or if you’re lucky, you can land on #7-8 (run a business) as some kind of consultant/freelancer, treat it as your main job while you explore options for #6 (start THE project), and then do the cycle over and over until you break new ground.

If it was somewhere in the middle, neither a success or failure, you didn’t define your objectives clearly enough, and/or didn’t set a time that would act as the “tripwire” at which point you evaluate the progress in the pursuit. More on this in the “WRAP” section below.

If it was a success, you’re ready to tackle bigger things, like solving the problems in the world and creating a new future for the next generation. This could mean anything under the sun: mentoring, speaking, writing a book, starting a company, consulting, getting into Hollywood, politics, mainstream media, or some other industry if that’s your thing, or taking a sabbatical to float around and explore options. Whatever you do, don’t get stuck trying to replicate the success of your last big project. If you do, make a different spin on it, and don’t do anything similar to your first project more than twice…that will make you plateau at being an “expert”…but only within your own industry. It’s kind of like being the guy with 3 PhDs…boring, overspecialized, overkill. Or the guy who ran 50 marathons in 50 states in 50 days, or the stereotypical “serial entrepreneur” who did 3 businesses and has lost sight of things like relationships and health (unless you want to be the absolute best in the world at one thing, and do nothing else, in which case you’re probably not born in the generation to which I’m addressing :)).


Spend as little time as possible delaying on a decision. How? Use WRAP:

[W]iden options. Aim for 3-4 options per decision. Usually we get stuck at, “Should I do X, or not do X?”, which presents only 1 option essentially.
[R]eality test assumptions. Two methods: (a) Consult experts/people who’ve been there, and/or (b) Test-drive each option for a trial period to get first-hand knowledge. (e.g. When hiring freelancers, method (a) doesn’t work–you’ll only know who is good when you make each freelancer do, say, a 1-week paid trial project. A bad freelancer costs more than paying for the trial periods of 3-5 freelancers.)
[A]ttain emotional distance. Ask yourself, “If someone were to replace me in this role, what would they choose?”, and “How would I think about this option in 10 minutes vs. 10 months vs. 10 years?”
[P]repare for the worst, and best. Now, go forward with your chosen option. Set a “tripwire” time to evaluate whether your chosen option was a “success” or “failure. e.g. “3 months from now, this is a success if X and Y.” Have a plan B and second tripwire in case the choice was a failure e.g. “In 3 months, if X and Y are not achieved, I will implement my second best option”, and a success maximization plan in case the choice was a success “I need to have a backup server and lead capture system in case my site gets way more traffic than expected on launch week”.

If consistently failing in some area (health, wealth, relationships), maybe the one holding you back is YOU.

Spend 5-10 minutes every morning conquering inner demons and cultivating a new mindset more fit for your goals (Step 1Step 2Step 3).

Adopt the 90% hyperconservative/10% hyperaggressive barbell strategy.

For massively beneficial yet massively safe risk-taking in money, career, and life.

Ups and downs are okay.

You can actually take advantage of the roller coaster instead of resisting.


And that is my tentative formula for an 18 year old’s future success. I wish I had done things in perfect order, but it looks more like a haphazard jumping between different steps.

What would you have told yourself when you were 18, given what you know now? Do you think there are essential parts missing from this framework?