In the summer of 2005, when I was 20 years old, I sat down and wrote one of my first personal goals:
“Hold a position in the Associated Student Government of Saddleback College at start of Fall semester (August 22, 2005).”
I had just dropped out of college on the East Coast after burning through all my college savings in one year. I’d moved back in with my parents in shame and enrolled in a local community college to try and get my life back on track. Writing down this goal was my first tentative attempt at regaining a sense of control and agency.
I can remember it like it was yesterday – how daunting it felt to commit to this goal, despite the fact that the position was uncontested and there were no real barriers to my winning it in the upcoming student government elections!
Even such a small, easy commitment required me to confront limiting beliefs: that I wasn’t good with numbers or with money. Even entertaining such a small amount of ambition meant I had to shift my identity, since I didn’t remotely see myself as a leader.
I’m happy to say that I persevered through those fears, took on the position successfully, and it ended up being a very rewarding part of my college career. More importantly, it was the inception of my relationship with goals.
Reveling in this first small victory, I soon after decided to write down a series of other goals I had for myself – for the GPA I would attain, for the girlfriend I wanted, and for the 4-year college I wanted to transfer to.
I discovered SMART goals around that time, and decided to attach a target completion date to each of them. Looking back at that list, the furthest date I assigned to my most ambitious goal was in 2025, when I would turn 40 years old. At the fresh-faced age of 20, I couldn’t fathom being any older than that. It was the farthest my imagination could reach.
Now that I’ve arrived at that seemingly distant horizon, I want to revisit not only that first batch of goals, but all the goals I’ve formulated for myself in the 20 years since. I’m less interested in which ones I accomplished or didn’t, and more interested in what I discovered and who I became by aiming for them in the first place.
Let me take you on a retrospective journey through 20 years of goal-setting to find out what I learned.
Building the foundation of adulthood
Looking at the list of outcomes I said I wanted in the earliest days, I can see that I was struggling and striving to build the foundation of my adult life.
Some goals had to do with seemingly small projects, such as creating a website to promote my first business, fixing people’s home computers:
“Build a professional, full-featured website for Forte Computer Solutions by beginning of Spring semester (January 14, 2006).”
I remember I didn’t succeed because there were no user-friendly website builders at the time, and I didn’t have enough motivation to learn HTML. But it was my first personal experience with the challenge of building things with technology, a subject I’m still grappling with today.
Some goals had to do with deep mindset shifts I underwent, such as diving into the world of Robert Kiyosaki’s book Rich Dad, Poor Dad:
“Complete Rich Dad’s curriculum: read and take notes on all Rich Dad books, master Cashflow 101 and 202, and read all books recommended by Robert Kiyosaki by end of Spring semester (May 20, 2007).”
I’d been raised by artists, and as useful as that was for my creative integrity, it didn’t give me any of the financial or business skills I needed. I spent over a year completely immersed, reading all Kiyosaki’s books, and many others he recommended, and even purchasing his financial education board game and playing it with my friends and family.
Looking back, I can see how fundamental that experience was for giving me an abundance mentality toward money – that it could be reliably earned, leveraged, multiplied, and compounded, and in a creative and values-aligned way.
Other goals seemed quite random and incidental at the time, such as getting my first English teaching job in Curitiba, Brazil, where I was studying abroad:
“Get a job teaching English at an established school in Curitiba by end of March 2008.”
Yet I now realize that experience opened up the door to my entire career in education. I see repeated evidence that some of the biggest endeavors in my life started so small.
Other projects were clearly massive from the start, and I have no idea what I was thinking taking on something so ambitious:
“Write Beyond the Orange Curtain and have it published by New Year (January 1, 2011).”
That was my first book, and I took every conceivable shortcut I could find to make it real. The chapters of the book were just unedited posts from my travel blog. I used a service called Blurb to design the front and back covers on my computer, and uploaded it to Kindle Direct Publishing. I remember I couldn’t bring myself to charge anyone for it, so instead I made it a fundraiser and donated all the proceeds to charity.
Fast-forwarding a couple of years to the start of my career, my goals started involving higher stakes. I began making real decisions about where my life would lead, with irreversible tradeoffs.
Kicking off my professional career
I returned to the U.S. from my service in the Peace Corps in December 2011, and immediately dedicated myself to finding a job in San Francisco:
“Get a job in the technology or non-profit sector and move to San Francisco by April 30, 2012.”
A few months later, I found myself in that city interviewing for the two jobs I’d received offers for: a junior analyst job at a French consulting firm called Fabernovel, and a role on the fundraising team at the Wikimedia Foundation (which manages Wikipedia, among other projects).
These paths couldn’t have been more different: the former represented a sharp turn into the world of business and technology, while the latter would have continued my current trajectory deeper into the world of non-profits. But I was already wary of the non-profit world. I’d spent much of my 20s in it, and seen a lot of dysfunction, politics, and waste. I decided I wanted to try something new and accepted the consulting job.
At that point, I notice a gap in my running list of goals, and I think it was because for the 18 months I worked at the consulting firm, I wasn’t responsible for choosing my own goals. They were assigned to me, in line with the broader goals of the company. That was useful, to see what it felt like for my personal goals to be subsumed into a wider mission.
I see my own agency emerge again in early 2013, as I started thinking about leaving consulting. I wanted to work on technology more directly, and started planning how I would apply to a tech company like Google, Coursera, Evernote, Udemy, Autodesk, Uber, IDEO, or Tesla.
I had no real technical skills, however, and knew I would need a stellar resume to have any chance. I signed up for a Squarespace account and built my own website, with a portfolio showcasing my credentials and accomplishments:
“Publish an online professional portfolio with documented evidence of my accomplishments, in a beautifully designed format by July 1, 2013.”
That ended up not being nearly enough, and I failed to secure even one interview for any of the roles I applied for at those companies.
A few months later, in June 2013, after yet another long night at the office banging my head on the keyboard and getting nowhere, I decided to call it quits. I was working too hard, for too little pay, and with too little control of my destiny. I would rather take my chances on my own.
Embarking on the journey of self-employment
As soon as my two weeks’ notice was up, I turned my portfolio website into a business website and threw myself into trying to make money any way I could think of.
I worked at random events, helped my friends with their projects as a subcontractor, and made my first online course on the GTD productivity method. That course ended up being an unexpected hit, and paid the bills for a while:
“Launch GSD.LAB on Skillshare and get 1,000 paying students signed up by Jan. 1, 2014.”
With a bit of financial breathing room, I had some freedom to experiment, and experiment I did. Looking back, I can see that many of the seeds of my future endeavors were planted around this time as seemingly low-stakes experiments.
I volunteered to give a talk at a local Quantified Self meetup, which introduced me to the subculture of people using technology for personal development in a systematic way:
“Create and deliver an inspiring, moving, cutting edge talk on my QS experiments for the QS SV Meetup on Nov. 18, 2013.”
The Quantified Self community ended up being my gateway to an adjacent field – personal knowledge management – that would become my main focus in the ensuing years. That talk actually took place at the Evernote headquarters in Redwood City, foreshadowing my relationship with the platform that would be my tool of choice for building my “second brain.”
After the lucky success of my first online course, I found it very difficult to continue making that income stream work sustainably. It was too hard to build the following I knew I needed, while also creating more courses and other products, while also doing everything else involved in running a business. I saw the potential of that career path, but wasn’t ready for it, so I turned to corporate training at the invitation of a mentor:
“Sign a major corporate training contract for productivity/workflow design by Apr. 1, 2014.”
Those workshops were well paid, and gave me a financial lifeline for a couple of years. More importantly, they happened infrequently, giving me lots of free time to learn new skills and pursue new interests.
Setting goals for my personal development
The life of a freelancer was quite uncertain and stressful, and I turned to meditation around this time as a basic survival measure after seeing an introductory book on it mentioned on an online forum one night:
“Establish a daily mindfulness meditation practice by May 31, 2014.”
That would eventually lead me to join a 10-day silent meditation retreat:
“Attend a 10-day meditation retreat by August 31, 2014.”
That experience was so profound that I felt compelled to write about it, which became my first blog post on a fledgling site called Medium. The meditation retreat was free, requiring only 10 days of my time. And yet it was a seismic shock to my psychology, kicking off two of the most significant themes that continue to define my life to this day: writing in public and my further explorations of personal growth experiences.
My next such exploration was to join a weekend seminar called the Landmark Forum, which I’d heard several friends talk about:
“Attend a Landmark Forum program by Dec. 31, 2016.”
I can still remember how daunting it felt to spend $700 of my own money on a seminar. And yet again, the return-on-investment was incalculable. I spent two years immersing myself in the world of Landmark as a result, taking a series of their other courses and seminars, culminating in their 7-month leadership program along with my then-girlfriend Lauren.
I see so many examples of how saying “yes” to something that seemed inconsequential at the time opened up entire new worlds for me. As another example, I agreed to write a series of 5 guest articles for an obscure blog I followed called Ribbonfarm. That experience was my training for writing long-form thought pieces, which would deepen my writing and thinking, attract my first consistent following, and give me exposure to a vibrant community that was the perfect testing ground for my own emerging ideas about productivity:
“Write a 5-post guest series on Ribbonfarm, laying out my vision for productivity and recruiting a smart audience by Jan. 31, 2017.”
And sometimes personal growth was less about reaching some mountain peak of experience, but about taking the time to engage in non-goal-oriented activities. I’m certain, for example, that the time I spent sailing was really important for my mental health:
“Receive Junior Skipper certification from Cal Sailing Club by August 31, 2015.”
I turned to sailing in 2015 when I needed an outlet that had nothing to do with my work, gave me exercise and exposure to nature, and helped me make new friends. The Cal Sailing Club operating out of the Berkeley Marina was my lifeline in all those respects, and I’m so grateful I set aside the time from my professional pursuits to learn to sail there.
The rise of Building a Second Brain
As I saw my ideas start to gain traction, an earlier vision returned: of creating an independent career of reading, researching, writing, and teaching, like a freelance professor.
I remember vividly in the fall of 2016 when a new goal emerged along these lines, which was intimidating, but also the perfect synthesis of everything I’d learned over the previous few years:
“Create a new online course on digital organization and creative execution, and deliver it to 50 people at premium prices, by Feb. 28, 2017”
As I reentered the online course space, I wanted to approach it differently from the “self-paced” course model that hadn’t worked for me previously. It’s agonizing to see evidence of how long it took me to arrive at that new approach!
Like watching the main character in a movie stumble around and miss all the obvious clues, it’s all so clear with my 20/20 hindsight vision. I wrote vaguely about creating some kind of “bootcamp,” which would eventually give rise to the cohort-based course model and a whole new category of virtual education.
Around that time, I switched from single-sentence SMART goals to more narrative-style visualization that contained more detail and specificity:
“I run a regular virtual bootcamp, enrolling my most engaged followers in a high-quality, engaging, accountable learning experience using the latest ideas and tools. I have a system for updating and delivering these bootcamps with minimal recurring effort, dedicating most of my time to providing coaching, feedback, and support for their projects and businesses. This bootcamp helps me test and refine the key components of my new vision for productivity, generating testimonials, case studies, and examples for a book.”
My first small beta group ended up being only 15 people, mostly friends or acquaintances who agreed to be part of it for free, in exchange for providing their feedback. We met once a week for 4 weeks, and I recall creating the slides for each call immediately before it took place, based on the feedback from the previous one.
That feedback, thankfully, was excellent, and I went on to deliver a series of cohorts to slowly growing numbers of people, at slowly increasing prices. I can remember reaching the following goal, which finally confirmed that this was a sustainable model for me:
“Deliver BASB v3 to 80 people, generating $48k in revenue, by August 31, 2018.”
It’s astonishing to me to look back on this fledgling start and see what Building a Second Brain has become. In the 7 years since, it’s served hundreds of thousands of people via an ecosystem of books, courses, a membership, and a sea of content, created both by me and countless others. Yet it all began with a goal written down on paper.
It’s also amazing to look back on issues that once occupied a lot of bandwidth and stress, such as putting aside money for taxes and making estimated tax payments, which are now completely automated, and I don’t spend one second thinking about. Other concerns that once seemed unbelievably far in the future, such as saving for retirement, now feel much more relevant since reducing our tax burden has thankfully become our main problem!
What I learned from unfulfilled or delayed goals
I’ve recounted a succession of the goals that worked out and led to something greater, but I can also see many, many others that fizzled out, were off the mark to begin with, or would take far longer to come to fruition than I imagined.
In early 2017, I felt a desire to connect with other creators and entrepreneurs, since that lifestyle could be so solitary so much of the time. I had no idea what that could look like concretely, however, and you can see that lack of clarity in how I worded it:
“Establish a group of like-minded, ambitious, engaged people for mutual learning, accountability, community, and growth by June 30, 2017.”
That desire would persist and only grow over the years, before finally manifesting as the Wholesome Mastermind I would start 6 years later, in 2023. In retrospect, I can see that I wasn’t ready to host an event like that one until I’d reached a certain level of financial stability and gained enough of a reputation that other entrepreneurs would be willing to join.
Other goals seemed to take shape quickly, but would involve many iterations before I figured them out. In 2017, I decided to hire someone for the first time, as the BASB cohorts took off and I needed a course manager to handle the logistics:
“Establish a solid working relationship with a collaborator, significantly boosting my productivity and profitability by Dec. 31, 2017.”
I can still remember how scary that was, what an immense responsibility it felt like, and how hesitant and unclear my expectations were. I hired the first person who offered to work with me, without any semblance of a wider search. Eight years later, and after hiring probably 20 people in the interim, I’m finally starting to feel like I’ve achieved a balance of autonomy and accountability with my team.
The narrative style of goal-setting that I adopted around this time led to an unexpected side effect: it revealed a lot more detail about my mistaken assumptions around what would bring me happiness and fulfillment. The results are often insightful or funny.
In early 2014, I wrote:
“I wake up after a restful night of sleep, which was tracked by QS devices for later analysis. I record my health metrics using a smart scale, activity tracker wristband, and other QS devices.”
LOL! At this time, I was neck-deep in the Quantified Self movement and related ideas, and believed that self-optimization was the path to self-fulfillment. If only I could achieve a high enough sleep score, fitness score, productivity score, etc., then surely I’d be happy!
That optimization mindset extended to my surroundings and the products I bought:
“My chair was chosen after in-depth research and perfectly supports my spine. I’ve also studied and practiced the best sitting techniques and ergonomic positioning, and use them.”
Thankfully, not long after this period, I would realize what a dead-end self-optimization becomes after a certain point. I learned to satisfice instead: to allow most parts of life to be relaxed and somewhat “mediocre” at any given time, so I could focus my energies on a few things that truly matter.
In 2014, I invested a lot of time and money launching my second online course, on habits, which would end up being a tremendous flop:
“I am teaching an online course on behavior design, teaching newcomers how to make a plan for designing and sustaining new habits, and how to execute the plan using the best ideas, methodologies, and tools out there.”
My choice of topic was spot on, as the meteoric success of Atomic Habits a few years later would demonstrate. But in retrospect, I can see exactly what didn’t work: what I was teaching wasn’t authentic to me. I’ve never been particularly committed to habits or a routine of any kind. I don’t even really believe in them, preferring to flex and adapt my choices to how I feel. That tension, between what I was recommending and how I lived, showed up everywhere and doomed the project from the start.
But even that failure taught me a profound lesson: that I shouldn’t chase the trends or try to do what was popular. I have to follow what is authentic to me, what I’m passionate and inherently curious about, even if it seems to lead somewhere random. I still follow that principle to this day.
Goals as a means to self-knowledge
I notice in my narrative goal-setting that I had a lot of beliefs about what my work “should” look like, many of which turned out to be misconceptions.
For example, I kept returning to the idea of “one-on-one coaching,” since that has always been such a powerful trend in personal development circles in the San Francisco Bay Area. But I would eventually learn that coaching wasn’t a good fit for me, and I was much better suited to monetizing my knowledge through courses that could serve many people at once.
The same is true for public speaking. I wrote:
“I speak regularly at events and conferences around the world, using them as platforms to spread my message and impact people directly.”
And for consulting:
“I consult with the world’s most influential organizations, shaping the development of products and services that manifest human-centered design principles and what I’ve learned about human-centered work.”
I had other misconceptions around what was important in business. I put way too much emphasis on having a slick brand for Forte Labs in the early days, for example, pouring time into logos, business cards, and beautiful slides:
“The Forte Labs brand has been completely redesigned and refreshed, presenting a look and feel equal to the world’s most innovative brands. This brand is reflected in the website, all social media properties, and printed materials, providing a consistent and alluring experience with every interaction.”
With the benefit of hindsight, the brand didn’t matter at all and would only become important and clear when BASB came about.
Many of the goals I set for myself were most useful not because I successfully achieved them, but because I didn’t. They taught me what I truly wanted and didn’t want. That self-knowledge and self-awareness is far more valuable than whatever I would have gained by unquestioningly pursuing those goals to their completion.
I had so many fanciful ideas of what I thought I wanted, such as “having breakfast in a super modern, gorgeous kitchen.” It turns out that acquiring a “super modern” kitchen requires renting a super modern apartment, which is very expensive. I found that I much preferred to live in affordable places that didn’t stress me out when rent was due.
Another example is “frequent business travel,” which felt so luxurious and prestigious for a short period, until I quickly realized I wanted to avoid it at all costs.
The runway is longer than you think, but the plane can soar higher than you imagine
Many goals I set for myself seemed so far out of reach, and were far out of reach! In my 2015 goal-setting, I dared to write:
“I’m generating $200,000 per year in pre-tax income.”
This felt like a totally audacious sum, and it would be 4 years until I achieved it in 2019. A couple of years later, as the pandemic fueled online business growth, our personal income would reach 7 figures, which my 2015 self could scarcely have imagined. I would give anything to travel back in time and see the look on his face as I delivered the news.
This is a case of a common phenomenon I can detect in retrospect: that many goals take longer to accomplish than I first imagined, yet once I do, their potential can greatly exceed my limited imagination. In other words, I tend to underestimate the “runway” needed for the plane to take off, but once it achieves liftoff, it can soar far higher than I can imagine.
Another example of that principle is my book advance. In 2015, I wrote:
“I have a book deal with an upfront advance of at least $50,000.”
You can sense in my language a kind of pleading tone – I really would have been happy with a book deal of any size.
It would, in fact, take me 6 years to receive the first part of that book advance, but when it came, it was $325,000, a sum that exceeded my combined income from my first 5 years of self-employment. Today, a decade after I wrote those words, I’ve made $1.85 million from the book and associated product sales, and project that number should reach $6.8 million in earnings over its lifetime. Astonishing.
It’s amusing to look back on some of my earliest goals, such as to “reach financial freedom,” which I defined as having enough passive income to meet my expenses:
“Become financially secure (passive income = expenses) by age 33 (May 4, 2018).”
I understand now that that goal was based on a misconception that work was something I should try to “escape.” From the vantage point of today, I wouldn’t want to stop working even if I had the choice to, as it’s one of my greatest sources of learning and fulfillment. And I know that the sense of security I was looking for isn’t found in a certain size bank balance, but in a holistic life of rich relationships, including a healthy relationship with risk and uncertainty.
The same is true for personal goals. Almost every year, I wrote down something along these lines:
“I perform some type of exercise every day, and vary my exercises to keep me in shape and support overall health.”
Over time, I tested out a variety of theories about health and fitness, such as Paleo-style diets, CrossFit workouts, high-protein breakfast, etc., that were making the rounds at the time. None of them ever really stuck for long.
Regular exercise has always been my “white whale,” and it is only over a decade later, in 2025, that I can say I’ve (more or less) formed that habit. I find that I’m able to do it now because I’m in a different life stage with different, more aligned motivations: not to get ripped or impress girls, but to avoid aches and pains and be more active with my children.
I see so many examples of just how long it takes many desires and intentions to come to pass. We tend to think in weeks, months, quarters, and, if we are really long-term thinkers, at the scale of a year. But I can’t help but conclude, as I look back at 20 years of goals, that most of my most meaningful pursuits took years to manifest.
Goals for the business
I see many examples in my business-related goals of a variety of theories and hypotheses I was testing at various points.
In 2020, I tried having “no meeting days”:
“Each day has a strong unifying intention, either free of appointments so I can focus on producing something, or open and spontaneous to make myself available to people who need me.”
But I would soon discover that a day was too large a block of time, and it fit my energy cycles much better to reserve all mornings free of meetings, and to spend the afternoons on calls.
I can see I consistently underestimated the impact of the economic and cultural environment on my business growth, thinking it all depended only on me instead of trends in online education and the economy:
“Forte Labs is growing explosively, not because of what I’m doing or pushing through, but because of who I’m being.”
I see other examples of my naivete, such as thinking I could “open source” all my content and still have a profitable business:
“Everything I know is open-sourced and available to help people create more freedom, pleasure, and impact in their work and lives, whether they ever buy from me or not.”
Some goals represented major initiatives that turned out to be completely misguided.
“I oversee an online course incubator, which regularly turns out new courses and other offerings that generate income and value for the people that have developed them. I provide every piece of knowledge, service, and counsel the participants need to develop their idea to fruition, and take a percentage while giving them a worldwide sales and marketing platform.”
We did pursue trying to build a platform and marketplace for multiple courses from other instructors for about a year, but that failed miserably as it wasn’t in line with our values or capabilities.
I laugh at how unclear my articulation of what I do has been:
“Our community is the world’s best source of conversations, curated resources, tutorials, and experiments on the future of work.”
I don’t think it’s that much better even today!
I’m also reminded, looking back at goals I’ve set, of just how diverse and wide-ranging my interests are:
“I oversee a portfolio of experiments pushing forward the boundaries of my field, such as group knowledge management, design thinking, science fiction prototyping, behavior change, self-tracking, art and music, crowdsourced collaboration, full-stack freelancing, online marketing, project management, community building, creativity, emergence, history, self-awareness, online learning, time-tracking, visual thinking, and writing.”
This exercise is a reminder to revisit some of those interests that I didn’t have time to pursue in the past, and perhaps resurrect them in a new form.
What I value today
Surveying the long arc of my goal-setting history, it’s clear that getting married and starting a family was the most consequential shift in my life. It changed every aspect of my life, including goal-setting.
One of the earliest goals I wrote down at 20 years old was this one:
“Get married to a beautiful, loving, intelligent, spiritual, sensitive woman who will make a great mother, in a wonderful gathering of our families that creates a community around us, by December 31, 2020.”
That wedding would take place in April 2019, and I couldn’t even imagine how meaningful, complex, and fulfilling that marriage would be.
I can see Lauren’s influence on my goal-setting earlier, however, such as in 2016, when I wrote:
“I respect the cycles of my body, mind, spirit, family, friends, community, nature, and nation, leaning into each season as an opportunity to bring balance to a new aspect of my life.”
She taught me balance, and nuance, and how to savor life in the present rather than only living for the future. I would never have written the following intention if it weren’t for her:
“I am ambitious but equanimous, driven but tolerant. I don’t go to unnecessary extremes, and accept moderation in most areas of my life at any given time.”
Some of the most meaningful, precious intentions for me these days are not the business milestones, but rather the mundane details of a calm and peaceful life:
“We go to bed early, reading and meditating, and fall asleep with a sense of peace and deep gratitude.”
How I set goals today
Around the birth of our daughter in 2022, I noticed that the list format for my goals that I’d kept for over 15 years at that point no longer resonated with me.
It’s because our lives themselves had become non-linear: it was no longer about the steady march of piling one brick on top of another, or winning each leg of a race. We are now a family of 4, with a lifestyle and business that my younger self couldn’t have imagined. Life has become more about enjoying our days, finding meaning in them, and squeezing the juice out of everything life has to offer.
So I switched to a mindmap format to try and capture the non-linear, exploratory, and serendipitous way I think about goals today. The mindmap has three clear parts, reflecting how clearly I see the three main priorities in my life: Family, Health, and Work.
Here’s the most recent version, as of the end of 2024:
打算把我相对能看得懂的公司商业模式捋一遍，今次讲讲迪士尼。老规矩，内容都是来着我自己这个老股东的理解，从开始建仓到现在，核心仓位拿了很多年了，也是我较大仓位长持的公司中整体回报率最低的一家。我一直奉行只买自己熟悉和（相对能）看得懂的公司这样一个基本原则，因此职业的关系手里大部分持仓都是科技股，像迪士尼这样的公司显得比较另类。