My mom’s death in 2009 was the defining event of my 20s. Turning 30 today, I find myself halfway between the age when that tragedy struck my family and the age she was when she passed.
Not surprisingly, it’s invited a fair amount of reflection.
I’ve spent quite a bit of time looking back over the past 10 years, on the triumphs and failures of my twenties, on all the lessons learned – mostly the hard way. I’ve also spent nearly as much time looking forward, thinking through how I want the next 10 years to look and the lessons I’ll need to apply.
In that spirit, I thought it would be useful to document what I’ve learned, partially as a guide to others, but primarily as a reminder to myself as I begin the not-so-long march to 40.
1. The master formula: Outcomes = Tactics x Energy x Time x Luck
By outcomes, I mean the thing you are aiming to achieve in life across all dimensions – career, financial, relationships, spiritual, the whole enchilada.
I define tactics as what you spend energy on in pursuit of an outcome, energy as a measure of intensity of focus. Time speaks for itself.
By luck, I’m referring to anything external outside your control that contributes to success or failure.
The master formula is so obvious that it almost borders on tautology. Yet, I’ve found it helps to simplify the levers that you can pull to influence achievement.
The sequencing is important. Clarify the outcomes you want to achieve before implementing tactics to get there. Choose the most effective tactics to reach your goals to avoid wasting energy. Don’t worry about investing more time implementing tactics until you’ve figured out how to squeeze as much energy out of every spare minute. Acknowledge luck, but don’t plan for it, optimize for it, or sweat when breaks don’t go your way.
2. If you buy into the master formula, then the most important decision you can make in your life is what outcomes you want to pursue. That, in turn, defines where you spend all your time and energy. Most people live life unintentionally, chasing the careers, hobbies, and romantic partners that their family, friends, or society-at-large deem acceptable.
Maybe that’s the right path for you. At least make it a deliberate choice to consciously pursue, as opposed to walking down an accidental path towards meaningless and mid-life desperation. her than an accidental pa to answer for yourself is what outcomes you want to pursue in life.
3. People who are most satisfied with their work are not those who make the most or have the best perks, but are those who have the greatest impact on the lives of those around them. In my opinion, most people get this wrong and lead unfulfilling lives because they insead make the pursuit of pleasure and the avoidance of pain their two primary goals in life.
I’ve found this phenomenon to be at its most pronounced in the career world. You have people who seek visceral pleasures: fame, sex, money and the luxuries it affords. These are the type of people who will eat shit for decades in grueling jobs like investment banking, not because they enjoy the work, but because it boosts social status and enables a luxurious lifestyle.
You also have people who take the cushiest job possible, who exchange the growth that challenging work provides for free massages, a 35 hour work week, and a stable paycheck.
Last, you have people who chase their passion as a means for self-fulfillment.
Comfort, money, intellectual self-gratification are all nice…but are they worth building a life around?
4. Yet, pleasure feels good; pain feels bad. Even with a clear outcome in mind that transcends these goals, it can be incredibly hard to stay focused on that outcome instead of being distracted by pleasure and pain.
This is where I think spiritual practice – and I use the word “spiritual” very loosely – can be extremely helpful.
For me, Stoicism has provided the most helpful mental frameworks and practices for doing so.
Its most important lessons for me?
First, to always do what is best for the whole, not the self. And second, to intentionally, proactively inoculate myself to pain – practice poverty, as Seneca puts it – to train myself to do the right thing in spite of pain. Intense workouts, cold showers, and long fasts condition my body to deal with discomfort, makes it my friend. In doing so, fear of discomfort loses its hold on my decision making.
(If you’d like to learn more about specific strategies you can implement from Stoicism to reduce stress at work and accelerate your career, check out my free week-long email course on Stoicism in the office).
5. Choose your environment and your associates wisely. The research is clear – your environment determines what you think, how you act, who you become. if you spend time around smokers, you are more likely to become a smoker. If you spend time around people who are overweight, you are more likely to become overweight.
As Goethe once remarked, “Tell me with whom you associate, and I will tell you who you are.”
Sure, you can try and fight peer pressure. And indeed, you should. But it’s much easier to choose the right peers in the first place.
6. Human suffering comes from “values conflict” – the desire to achieve mutually exclusive outcomes. It’s the working mom or dad who wants to put their all into their work while also being there for their kids. It’s the artist who wants to wants to be financially prosperous without feeling like they’ve sold out.
People want more than it’s possible to have. So even when they reach one goal, it’s at the expense of the other. Almost always, the pain of the failed goal outweighs the pleasure from what’s been achieved.
I haven’t figured out a great way to completely solve for this. I think there are two ways around this problem.
7. One way to dissolve values conflict is to accept pain and failure as a part of life, accept the limitations of what can be accomplished, and realize that you will never achieve everything you want to in your short life.
It’s a realization that is in equal parts depressing and liberating.
8. The second way is to reduce the number of things that you want in life in order to feel successful. For me, I’ve given up most of my interests, hobbies, and casual acquaintances in favor of a few things that I find most important – my health, my marriage, close friends, my career, and creative projects – in that order.
This makes the target that I aspire to achieve, the outcome on the left-end of the master formula, much more attainable.
9. The two questions I’ve found most helpful in charting a deliberate direction in life:
- What is the impact you want to have, and how much money do you need to make to have that impact?
- What are the type of people you want to be with?
Over the past 10 years, what I’ve observed is that much of the frustration and angst of my generation stems from a lack of deliberate reflection on these questions.
Without a clear sense of the impact you want to drive or how much money you need to make to live your ideal life, it’s easy to fall into the trap we covered earlier of pursuing comfort or wealth as ends unto themselves, instead of as means to a greater end.
A similar phenomenon occurs in relationships. Without being explicit about the type of people you want in your life, it can be easy to lower the bar and let toxic people into your life as an antidote to loneliness.
10. Once you’ve spent time to understand the outcomes you want to achieve, understand clearly your strengths and weaknesses. This helps you find the right “technique” with which to apply your energy and time in focus of your outcome. I’ve found something as simple as the Clifton Strengthsfinders Assessment, which cost me $20 and an hour of my time, as one of the highest ROI investments of the past ten years.
11. Those of us who work in the corporate world understand the wisdom behind Peter Drucker’s quote that “what gets measured gets managed.”
In addition to applying this at work, I’ve found it equally important to apply it in my personal life. Setting KPIs for my physical performance, amount of sleep, how much time I spend writing, and other key areas where I am looking to invest my time have played a crucial role in helping me achieve my goals.
12. Speaking of the corporate world: when picking an employer, apply the same level of scrutiny that you would if you were a venture capitalist looking to make a multi-million dollar investment.
Because, in fact, you are investing something even more valuable – your time, and your emotional well-being.
Like any good investment, it’s important to look beyond upside and to ensure you are minimizing risk. Has the leadership behind your company been successful in similar roles and previous companies? How about your boss? Does the company have a proven business model, or is it still grasping for product-market fit? How much is the industry the company is in growing or shrinking?
These were the questions that I did not ask when I joined my first start-up. While I learned a lot, I also dealt with a lot of frustration along the way as the company failed to effectively capitalize on its market opportunity. When I left, I declined to exercise my options, believing that even at their paltry strike price that they were worth less than the strike price.
A couple years later, the company was later bought out by a competitor for half of what it was worth when I joined.
The second start-up I joined demonstrated all of the characteristics that were absent from the first – strong and experienced leadership, validated product-market fit, in a rapidly growing industry. A year after I joined, we went public; a year after that, we were acquired for over double the valuation at the IPO. This has led to a much more fun, fulfilling, and rewarding work experience.
Just like there’s no such thing as a risk-free investment, there’s no such thing as a risk-free career change. But by thinking like an investor, you can significantly de-risk any transition you make in your career while minimizing the chance of downside.
13. What I’ve also found is that the most important thing to optimize for when choosing a career is learning. For all of the struggles I faced in that first startup, I still would have opted to work there knowing what I know now.
At that company, I made what I consider to be my most important career move – taking a 30% pay cut to transition from sales to be a founding member of our marketing team. It was an opportunity that may not have been afforded to me at a more established company, which may have been looking to hire somebody externally.
I don’t have an MBA, but I like to think of those first two years I spent as a marketer, making substantially less than in my previous sales role, as a kind of equivalent investment. It helped me establish the foundation that I’ve since been able to build an incredibly fulfilling and rewarding marketing career on top of.
14. When sweating the small stuff, or off-track from my main mission, or simply feeling unmotivated to do what needs to be done, I’ve found no better anecdote than reflecting on my own mortality.
I think Steve Jobs put best why in his 2005 Stanford commencement speech:
“Remembering that I’ll be dead soon is the most important tool I’ve ever encountered to help me make the big choices in life.
Almost everything–all external expectations, all pride, all fear of embarrassment or failure–these things just fall away in the face of death, leaving only what is truly important.
Remembering that you are going to die is the best way I know to avoid the trap of thinking you have something to lose. You are already naked. There is no reason not to follow your heart.”
It’s life’s scarcity that gives it valuable, that makes the tradeoffs meaningful, and makes sacrifices worthwhile.
15. In structuring life and work, optimize for energy instead of time. One hour of intense and dedicated focus can be more powerful than ten hours of tired and distracted thought.
16. For all of the buzz about nootropics (and my own personal predilection for Alpha Brain), I’ve found quality sleep to be the single biggest performance hack. Few and far are the occasions where I’ve found it to be more efficient to get less sleep, no matter how busy I am.
My experience has been that 10 hours of work on 8 hours of sleep will be much more productive than 12 hours of work on 6 hours of sleep, or 14 hours of work on 4 hours of sleep.
Getting less than 8 hours of sleep a night also increases risk of heart disease, cancer, obesity, diabetes, and Alzheimers.
Why anybody wouldn’t make sleep their number one priority is beyond me.
17. Workout hard. After sleep, I’ve found exercise to play the largest role in my clarity of thinking, stress levels, and overall mood. Even 10 minutes of high-intensity exercise first thing the morning makes a massive difference.
18. Habits eat willpower for breakfast.
You only have so much drive you can put towards your goals. Unless you’re a robot, on some days, you’ll be feeling extra motivated, and on others, even getting out of bed in the morning can be a struggle.
The more you can make the important things in your life automatic, the less reliant you become on motivation. When you are feeling that rush of motivation, it’s best to invest that into building failproof systems and habits that will ensure that you follow through on your goals even when you are feeling completely unmotivated to do so.
19. Given that motivation and willpower are so precious, scarce, make a deliberate effort to subtract things in life that tax them.
Improving life doesn’t always have to be an exercise in adding new habits, behaviors, or rituals. In fact, it’s probably better to eliminate the bad than to add good, all things being equal. A pack-a-day smoker will be better off if they quit smoking than if they keep smoking but start an exercise routine to make up for it.
This is why it’s so important to exorcise toxicity from your life in all its forms.
20. To the extent possible, trade money for energy whenever possible. If there are certain things that are draining for you to do, like cleaning, cooking, or doing grocery shopping, paying to outsource those tasks is one of the best investments you can make in your quality of life – especially when you reinvest the time and energy saved back into your work.
21. Push flywheels, avoid doom loops.
By flywheel, I mean an activity or sequence of activities where the impact compounds over time.
Learning a foreign language is a good example of an activity with a strong flywheel effect. When you first start learning, communicating with others in the language can be a difficult process. You have very few words at your disposal, and can’t understand almost anything the other person is saying. But as you continue to study, conversations become easier, more exciting, more fulfilling. This, in turn, provides you with more energy to continue your studies, which leads to more improvement, creating a virtuous cycle.
Pursue work that allows you to establish momentum such that the natural result of that activity gives you more motivation or energy to work harder, learn more, get better.
If you don’t…there’s a chance you could get stuck in the opposite of a flywheel – a doom loop.
Imagine a dead-end job where you aren’t able to drive meaningful impact. Over time, not getting that positive reinforcement leads to lower motivation and energy, which leads to even less impact over time, which leads to further demoralization.
Doom loops are as fatal as flywheels are beneficial. They are death for your career, your relationships, your physical and mental health. Avoid them like hell.
22. Embrace deep work. The best work is done without distraction.
Don’t be afraid to pay the short term cost for disconnecting, in exchange for the long-term pay-off that increased focus on a single, important task brings.
Never be afraid to shut yourself off from the world for hours or days at a time if that’s what’s needed to get a big project over the line.
23. Quit social media. Or at least try going a month without it.
Around a year ago, I phased social media out of my life for the same reason I stopped smoking. It was making me unhappy, and was detrimental to my health.
Like social media, I found smoking to have it’s set of positives. It was a good stress reliever, and provided an easy way to meet new people when going out. I found these short-term benefits outweighed by the long-term cost to my physical health in the case of smoking.
Just because there are good things that come from social media does not mean that these good things are outweighed by the long-term harms.
I never intended to permanently disconnect from social media. But after taking a month off of Facebook, Instagram, and Twitter (I’m neither young enough nor cool enough to use Snapchat), I found the increase in focus and decrease in social anxiety to be well worth what little I had given up in exchange.
24. Fill empty space with mindfulness. When people quit social media, a host of magical moments to think and reflect reveal themselves. The precious early moments each morning that you used to fill checking Instagram. Or waiting for the elevator at work.
What I’ve found is that the more you can tune out your phone and tune into yourself and the world around you, the richer of a life you can experience.
25. In addition to the above, sometimes the most therapeutic thing to do in stressful times is nothing. By nothing, I don’t mean watching Netflix, or putzing around on your phone, but actually doing nothing.
Create the conditions for epiphanies. Because they aren’t going to come while you’re watching the game or scrolling through your newsfeed.
26. If you care about personal growth, take on the hardest challenges you can. Difficulty and adversity build character and capability, just like lifting heavy weights builds muscle.
27. Read as many good books as you can. Books are the single best investment in time and money you can make. A good book enables you to absorb the expertise and experience that somebody built over the course of decades, all for the cost of a San Francisco lunch and a few hours of your time.
In your 20s you will read 100s of books that will change your life in small but meaningful ways.
Here are the books that have had the biggest impact on my thinking:
For learning how to become more skilled in delivering on my purpose – Mastery, by Robert Greene.
For harnessing energy in service of that purpose, The Power of Full Engagement, by Jim Loehr and Tony Schwartz.
For staying grounded and focused on what matters, Why Buddhism is True, by Robert Wright.
(If you’re interested in more book recommendations, I’ve put together free executive summary for 12 of my favorite books. Click here to have it sent straight to your inbox.)
28. Invest in relationships. One of my biggest regrets is that, through simple neglect, I’ve let good friendships die.
It’s a lesson I hope I don’t have to relearn.
29. Do something fun every day. Block off time for yourself, and treat it as sacrosanct as the most important meetings in your calendar. Having time dedicated purely to recreation and pleasure provides an island of solace amidst stress. It gives you something to look forward to. It provides a release valve which makes the “productive” time before and after more useful. And, it just makes life more pleasurable to live.
30. The last lesson and most important lesson: be humble.
When I was 21, I looked back at my ignorant teenage self with pity: “How clueless I was then, how wise I am now.”
I repeated a variation of the same exercise in my mid-twenties, thinking myself so much smarter than I was when I graduated college.
I recognize now that so long as I can keep learning, I’ll keep having this epiphany on a semi-regular basis. And after having it enough times, I’m giving up on the idea that *now* I “get it.”
I’m sure that I’ll look back on the above 5 years from now and laugh at some of the things that I currently find to be true. Perhaps some of you are laughing now.
But though I can be certain that my thoughts on the above truths will evolve, the only way I know they will do so is by testing them in the wild, using what I’ve learned to be a better person in my thirties, and to continue iterating on these truths as I gain more experience in life.