Be in the "Arena": The secret to better decision-making and maximizing your potential
An essay on the importance of being in the Arena to unlock stronger decision-making and creative potential -- and how to actually operationalize this in your day-to-day.
It’s easier to be an ordinary skeptic — to observe from a faraway place of comfort — than to fully commit to something and build a point of view from there. The famous quote below by Roosevelt echoes this sentiment in a powerful way:
“It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows the great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.” — Theodore Roosevelt
I argue that to be in the “Arena” is the greatest source of growth and learning that one can truly obtain. Too many fresh graduates or those in their early careers settle for “superficial understanding”: either analyzing or finding potential flaws or merits in arguments or ideas just based off of things that people tell them, or tidbits of news that they chance upon. But when you’re “in the Arena” — you see things for what they really are. You observe the deepest challenges, but also begin to understand the merits or potential of things. Being in the Arena exposes and exacerbates the flaws of ideas, but it also helps you spot opportunities no one else can.
Take an analogy from my co-worker Ujan, who reflects on his life as a recent father of a current two-year old: “Nothing — no amount of books or training — could have prepared me for the ups and downs of being a dad. It’s just not something that you can convey without the actual experience itself.”
Let’s take this perspective and take it a step further with how it relates to our careers — especially those who are builders, visionaries and entrepreneurs.
eBay, the iconic auction-based marketplace, was founded in 1995 by a visionary named Pierre Omidyar who envisioned — in the early days of the Internet — the ability to create a perfect open marketplace, where the laws of supply and demand of any good could be decided by the hands of its participants through auction-based mechanics.
As evidenced by the picture above depicting eBay (then called AuctionWeb), eBay was not as well-funded as its competitors nor stood out in terms of its technological prowess or user experience. However, what made it “different” was that it built a strong community around its marketplace to establish deep trust and to make people feel like they were truly interacting with other humans — kind of like what you imagine a Roman Bazaar to seem like. eBay users (community members) who interacted on the site’s forum banned together to do things like:
Formed an informal “neighborhood watch” where they banned together to act upon fraud cases (e.g. e-mail sellers who scammed buyers, coming to the aid of those who had received negative feedback unjustly)
Offer “value-added services” / support to other community members (an early member named Pongo assisted others in uploading digital photos for items)
Build stories and socialize together: characters like Uncle Jim or Skippy were iconic figures in the early eBay board days — helping others or just generally being positive social figures and spreading fun
Initial potential funders or even potential recruits were skeptical about community as a true competitive advantage. From the outside, it seemed like total BS. Times Mirror Company — one of the well-known publishers of the day — balked on a $5M investment in eBay (for 12.5% of company, something that would have translated into billions in ultimate outcomes) as it didn’t believe that both (1) online marketplaces would take off, nor that (2) community was a defensible advantage. The fact that the founding team was non-archetypal (with Omidyar being somewhat of a hippie), and infrastructure seeming messy made it less attractive.
You had to be “in the arena” to be able to truly understand that what eBay was creating was special. The founding team realized that its community-first approach was its bedrock as an online auction-based marketplace HAD to be trust-oriented, and continued investing time and effort in building it, and making sure that voices were always heard. Even as early, more outwardly appealing (e.g. more technologically strong) competitors came onto the scene like OnSale and Auction Universe — they could not compete with the seeming intangibles that small, scrappy eBay had. eBay had selective knowledge — knowledge only THEY had — from being in the arena and making moves / bets that no one else thought was valuable.
The example of eBay above highlights a powerful example of how skeptics, analysts, or even potential recruits — with only a superficial understanding and without “being in the arena” — would have missed out (like Times Mirror and others) on a generational investment or career opportunity with early eBay. On the other hand, one could have also taken an opportunity with any of eBay’s early competitors who ended up losing out, but seemed more capable in theory (e.g. more funding, more external resources and capabilities). Of course, you can NEVER truly predict the future — but being in the Arena is the only true way to harness foresight. That’s why entrepreneurs rarely care about what analysts have to say about their business.
It’s the reason why I personally ALWAYS put myself in the arena before making judgment calls on a certain direction in my career or life. Doing so has given me tremendous insight and conviction in my own beliefs and mental models — that help forge my path going forward. Here are a few examples of insights I gained that could have only been gained while being in the Arena:
Example 1: Public sector technology
For those of you who don’t know, I currently work as a Product Manager responsible for founding and executing a new business model for platformized teacher learning at GovTech Edu — with the goal of scaling a new, national curriculum focused on student-centered learning called Kurikulum Merdeka. If we succeed, we will be able to positively empower millions of teachers and thousands of principals to be stronger leaders for our students. When I first moved from Bain to take the job at GovTech, the initial perceptions from those around me was marred with skepticism:
“Won’t the work that you all do in the Ministry be futile after Nadiem finishes his term as Minister of Education in 2024?”
“Isn’t working in government extremely slow and bureaucratic that you won’t actually be able to accomplish or do much to affect change?”
“Won’t the talent, resources and infrastructure around you be so much less than a regular tech company that you won’t grow as much individually?”
I totally understand where people are coming from, but again these are all questions that exemplify “superficial understanding”. It’s easy to look from the outside and make judgment calls even before you’re in the Arena understanding what is truly possible and what is not possible. Taking the step to join GovTech was of course not a risk-free decision, but it wasn’t a “leap of faith” either. Prior to joining the company, I formed a perspective through reading books like Power to the Public and Empowered Educators that it was a worthy career move to attempt, amplified by my prior work in the education & policy field in Teach for America and IDinsight that gave me fundamental knowledge and confidence on the importance of education policy and pedagogy. And if I wanted to be creating deep impact in the education sector, I had to be in the Arena and this was the right time to take it. Since joining GovTech, I’ve learned the following things about public sector technology that have deeply informed my worldview:
Government has a unique, transformational role to play in creating deep, lasting change — but most governmental administrations don’t go deep enough. Since a presidency and thereby a ministry term is capped in time (in Indonesia — these are 5-year terms), there’s a perception that change is only superficial in nature. Even teachers we met feel this, stating a quote that “when a minister changes, a curriculum changes, so why bother?” That is to say — the real agents of change to mobilize are actually the people on the ground who will champion the change even after a term formally ends. It makes me realize that success of government programs actually comes from deep bottoms-up efforts rather than top-down scaled efforts.
While government is bureaucratic in nature, and there are significant poles of influence to watch for, it is (1) completely possible to influence strategic direction, and (2) the people within government are very capable. It’s important to keep these two points in mind, because influence in a government-setting is not as “simple” as a startup where data exhibiting positive user behavior changes and monetization are simple examples of what leadership cares about (of course it can be more complex — but this is just an example). In a government setting, it’s a lot more nuanced than that. If you can understand your stakeholders’ (who are again, quite capable) policy direction or their priority programs — it becomes easier to “align on their language”. You just have to make sure that you’re also equally as rigorous in your strategic thinking and direction — which a lot of people don’t take the time to do (hence forming the too early conclusion that government stakeholders are overly rigid).
Transformational efforts are built upon strong talent. You can’t skimp on this. I’ve seen that these more experimental public sector efforts need the strongest talent to support the build out who are also entrepreneurial in nature. I see this strongly at GovTech where we’re hiring some of the most talented people I’ve met (ex-venture entrepreneurs, ex-startup executives, ex-consultants). Talent is the backbone transformational change, and thus a public sector effort needs to invest the resources (salary, growth, leadership) to attract and retain strong talent, rather than relying purely on superficial things like “mission” or “doing good for the country”. We see Obama also taking this approach.
Being in the Arena of public sector technology has given me and my team the tools to be able to more deeply affect and influence change. When GovTech first started out — the mental models and the foundational infrastructure of how public sector technology could work were pretty much in state zero (e.g. the extent of how governments used to interact with technology were basically through vendor-based relationships and top-down, non-human-centered decision making). It resulted in us making questionable initial product decisions, as we didn’t know what to do.
However, each day we spend in the Arena since, contributes to a body of compounding knowledge that helps us understand how to create deeper, and more meaningful change. We grow up. We now deeply understand that going for “scale first” (what you think of most government programs) doesn’t work because then you don't build strong grassroots-led network effects which is what you ACTUALLY need to sustain irreversible change. We now have developed deeper trust with our counterparts in the Ministry of Education, allowing us to understand their points of view and make educated strategic decisions that have alignment with their policy direction. We now only focus on hiring top-tier talent zoned in on a few important products rather than placing the focus in growing the company and increasing the number of products. And beyond that — we know our users more deeply, and have built relationships on the ground that allow us to gain feedback in continuous ways.
These are all nuanced learnings that you could have only had if you’re in the Arena, doing the work on the ground and embracing failures and successes alike. We all went from superficial understanding (“this could or could not work”) to deep understanding (“this can work — and here’s why and how”). Similar to how eBay saw potential that no one else saw in communities, being in the Arena has given me insight on the key leverage points to make public sector technology successful.
Example 2: Web3 startups
For those who don’t know, I also spent 6 months this year supporting an analytics-focused Web3 startup as their first Product Manager on a part-time basis (before deciding to focus my time more fully on GovTech for personal reasons and given that demands are more intense now that I’m building a new business there).
From some outsiders’ perspective, Web3 / crypto is either a world-changing innovation, or it’s simply just an overhyped technology. Some people believe that it’s all a scam, while others believe it’s the best thing since sliced bread because of the *magic of decentralization*. It’s not that these viewpoints are wrong, it’s that the majority of people pick up these beliefs again very superficially — off of friends or articles they read — instead of “being in the Arena” and making a judgment call for themselves once they gain a deeper, richer, nuanced understanding. I was in the border-zone, leading me to follow my curiosity and put myself in the Arena in order to make my own informed judgments.
By actually being in the Arena, I learned a deeply a few things:
Someone who superficially understands the space will spout out about things like how blockchain primitives enable deep composability or permissionless access. While these are all theoretically true, I also saw how FAR the space was from having the infrastructure to actually achieve these tenets. It’s not as easy to plug into APIs or access no-code templates to build on top of (as builders might have been used to in Web2).
However, deep innovation is truly happening in every corner in the space — lifting up all boats. Data layers, identity, communications, and other foundational protocols are getting better everyday, with smart people building in the open. But there’s no “ definite winners” in any segment yet.
Given that infrastructure and tooling is still being heavily built, founders in Web3 need to be not only resilient but heavily adaptive and even experimental to adopt new mental models, integrations, and workflows. You can’t assume that the de facto way to do things will still exist even a few months forward.
While I’m not working in web3 right now, being in the Arena has given me the insight to be incredibly optimistic about the space but know that it’s still incredibly early, and that 99% of companies and ideas that exist today will not exist in their current forms in the next few years. I’m bullish on founders who have demonstrated incredible adaptivity and resilience throughout their careers to be successful in web3. And I’m especially bullish on those who are highly technical — as the lack of “plug and play” build options in web3 means that those who can build modular components in-house to support their product (even if scrappy) can move faster, and hence learn more than those who cannot do that. Being in the Arena has taught me to evaluate opportunities in web3 in a more rigorous way, and to know what it takes to win and the skillsets to develop (if I go back to the space) instead of listening blindly to the Bankless advice to: “Quit your job and work in crypto”.
Example 3: Entrepreneurship or working in startups (in general)
This is more straightforward than the rest, but as someone who has built and worked for early-stage startups — “being in the Arena” here illuminates how different early-stage entrepreneurship is than what the glorified stories tell you. Yes, getting venture funding is exciting. Yes, building a brand and conceiving a product from 0-1 can be fun. However, you should also know that situations like the following are inevitable:
No matter how “great” in theory your initial idea sounds, building a startup will almost imply having to pivot to new territory. Sometimes, ALL your work in developing for a problem space will have to be discarded when you realize product-market fit is unlikely to happen.
You’ll deal with founder or employee conflicts and hardships — as people will have doubts and leave the company, or you realize that there are certain clashes in belief with other members of the team on important things.
You’ll have fear that you’re not only risking your livelihood but also that of others along the way.
If you’re ready to deal with the above and much more, then you might be prepared to tackle an entrepreneurial journey. If not, then it might be a good idea first to test yourself. Not everyone should be an entrepreneur. Being in the Arena (perhaps through working in an early-stage startup as an employee) gives you the insight to whether or not the journey is suited for your character or not.
I hope through these examples you can start to see the difference between superficial understanding and deep understanding built through real experience. We often evaluate ideas or make big decisions in our life based on superficial or theoretical understanding — causing us to either underestimate opportunities or ideas, or jump into things before we have a strong enough grasp of what they entail. “Being in the Arena” allows you to gain deeper perspectives that help with decision-making.
So if you’re convinced now that the benefits of being in the Arena are worth it…
How do you actually put yourself in the Arena? Let’s say hypothetically you’re a:
Product Designer who’s interested in transitioning into the sustainability or green space. You want to make a “hard transition” — meaning that you don’t want your future role to be purely design related. You don’t really know much about how to get in the space, but you know that it’s impactful & meaningful. However, your career has mostly been in software design while the sustainability/green space seems like it needs other skillsets more.
VC who’s trying to get deeper knowledge into a hot space (let’s say web3); you always hear about how the “smartest people” are getting into the space, and you’re hearing about some big funding rounds, but your understanding is still very superficial (so you risk just agreeing to agree, and even recommending investment decisions because of the wisdom of the crowd)
Entrepreneur or Product Manager thinking through a potential direction in regards to product development. You have intuition that taking a certain direction makes a lot of sense — but there’s still a lot of unknowns.
How do you do this successfully while instilling the principle of being in the Arena so that you’re well-equipped to make the right decisions?
There are 4 steps to take in order to be in the Arena:
Don’t judge something too early, or listen to the opinions of people who are not in the Arena: It’s easy to be a skeptic, or someone who talks about something without actually having skin in the game. Taleb states: “Avoid taking advice from someone who gives advice for a living, unless there is a penalty for their advice”. In anything that you do — before you make a judgment call — ask yourself if you really understand something enough, or if you’re even willing to develop deep understanding. If not, shut your trap. I hear too many people without any skin in the game judge others’ decisions.
Develop as much foundational knowledge as you can in order to have an informed point of view: If you decide that you want to learn about something more deeply — develop as much of a knowledge base as you can without taking any sort of “leap” yet. You’re still at the superficial knowledge stage here, but at least you’re getting further. Taking the scenarios above, you can:
If you’re interested in the Green / Web3 spaces — read as much as you can about these industries. What is the current state of progress? What are the terminologies and industry language people use? What are the biggest challenges and roadblocks today? What are some companies that are working in the industry in my region today? Scour literature, get on the phone with people you find on LinkedIn, take some online courses. Your goal here is to “be informed”. Even before I became a Web3 PM for example — I already was learning and writing articles about Web3 even if those articles were still coming from a more superficial point of view (which is how I actually got the job in the first place, as the founder of the startup chanced upon my article and hit me up).
If you’re looking to potentially take a certain direction as an entrepreneur — try to understand the path as much as possible. Let’s say you’re trying to build a business with a marketplace-based business model (connecting supply and demand). Make an effort to understand the mental models of marketplaces from various angles. What are the most important things to consider? How do you solve the cold start problem? How do you maintain quality? If you can’t even understand how the best marketplace businesses operate (e.g. AirBnB, eBay, Uber) — which are ALL information that you can find literally online — then you haven’t passed this stage.
Test and experiment with the “smallest” endeavors you can that get you in the Arena without having to make a big life decisions too early: Once you have a strong enough foundational base of knowledge to at least be at the more informed side of superficial knowledge — then you should try to experiment with the “smallest things” that get you in the Arena. It’s important to note that in this phase you are actually in the Arena (even if it’s only a small step into the Arena). This is probably the hardest part for most people because they don’t know how to approach this. My advice: be permissionless. Don’t wait for opportunities to knock at your door, and try to ask yourself how to sneak your way into back doors. A lot of people try to use formal methods to do this testing — but it tends to take a long time (e.g. waiting for an MBA before they get their feet into the Arena, or waiting on an externship opportunity in the case of my fellow consultants). Taking the scenarios above:
Product Designer looking to get into the Green space can look for the Green-routes that are most closely aligned to their experience — which are probably more software-based Green startups (vs. ones building hardware like batteries or non-profits). They can scout for the Green startups in their region, and cold message the founders directly with a pitch of how they can contribute (e.g. offering design work, even for free, for an exchange of insight into the inner workings of the Green startup; the genius way some people do it is they redesign something that the startup has built and send it to the founders). The Product Designer can also message VC’s who are always looking for great talent for their portfolio companies to try to find a “way in”. Then the Product Designer can perhaps take up part-time or freelance responsibilities. In this case, how you find your way into the Arena is to ask the question: “How can I leverage my unique skillset in order to contribute to a field I’m interested in and gain insights from there?”
The above was how I actually got into Web3. I took on a part-time job as a Product Manager while I was working at GovTech. Yes, work was crazy and it was difficult to manage multiple jobs — but I made it work, and as a result got deep insight into working in the field that I would not have received otherwise without doing that. With this stage, you have to be deeply scrappy and willing to hustle to get in the Arena. However, if you believe that the benefits are worth it (and that it’ll end up resulting in you not wasting years of your life / time in the future, or leave you in a state of regret pining for an opportunity), I suggest that you hustle.
If you’re an entrepreneur or PM — before you decide fully on a path — take on an MVP mindset and continuously strive to iterate along the way. If you’re building a marketplace for example, instead of focusing on building out something fully-fledged and sexy on Day 1, you should ask yourself whether you can tackle the most risky assumptions through building the smallest, most simplest product with only ONE core value proposition: (1) Can you attract the “hard side” of the network with this? (2) Are users getting value out of it, and are willing to stick with the product? (3) Do you have a strategy to grow the network? If you can’t answer these questions before you go EVEN deeper — then you’re setting yourself up for failure. I see so many products launch with a lot of vigor but then fail to address many of the most basic questions.
When you’re ready, and you’ve assessed the opportunity enough, take the opportunity to be fully in the Arena: At this point — you’ve crossed the chasm from superficial understanding to a deeper level of understanding (although not as deep as possible). Based on your tactical experimentation above, you then decide at this point whether to forge ahead to fight fully in the Arena or to back out (which is totally fair and respectable).
If you realize at this point that being in the Green or Web3 space is not for you, or that the idea that you had for product development doesn’t work (which you were able to assess through actual experimentation) — then backing out means that you potentially just saved months or years of your life working on things that are not suited for you. That’s fantastic!
However, if you realize that through the smallest step of being in the Arena that you want to keep fighting onwards — then you have the opportunity to truly be immersed, and as Roosevelt states “mar yourself with dust, sweat, and blood”. Forging onwards is when you start developing deep, selective knowledge. Just like how eBay saw an opportunity that no else did, fully immersing yourself in the Arena gives you insight to ideation that no one else has — because being in the Arena and understanding deep nuances is what actually unlocks creative potential at its maximum.
With these four steps positioning you deeper and deeper into the Arena — you unlock one of the strongest secrets to decision-making that you can find. You start to move from a land of superficial knowledge to deep knowledge. And you start understanding the value of deep knowledge in being able to unlock creative potential.